# Andy Sparks — Full Content > Executive coach for startup founders and CEOs --- ## About ## Hey, I'm Andy I've spent my whole career starting things, screwing things up, and figuring out how to do them better. These days I coach startup founders and CEOs, and I'm building [Management Craft](https://managementcraft.co/) to write down everything I've learned along the way. If you're here to learn about coaching, [that's over here](/coaching). ## How I got here I've been an entrepreneur for about a decade across three companies. Between them, I raised over $20 million in venture capital, which sounds impressive until you learn that raising money is the easy part. What you do with it is what counts. I've spent my whole career outside traditional career paths, preferring to start things with people I respect and admire rather than work for someone else. My first company, LaunchGram, failed fast. I started it with two friends in Ohio after a startup weekend. We got a $50,000 grant from an accelerator, I sold everything that didn't fit in my Ford Focus, and we drove to California for 500 Startups. By the end of the program we realized we'd started the company for the wrong reasons, so we shut it down. I think of it as my starter startup, like a starter home. Before LaunchGram, I'd never really failed at anything. I'd coasted through most things and had a good time. Starting a company and watching it not work was the first time I made real contact with reality, and honestly, it was the best thing that could've happened to me. It made me get serious. It made me grow up. After LaunchGram failed, I decided I wanted to find someone who'd already been successful and apprentice myself to them. That's what I did at Mattermark with my co-founder Danielle Morrill, who'd been the first employee at Twilio. Mattermark was a blast. We helped investors figure out which startups had momentum before anyone else could see it. Think Moneyball for startups. I sold half of the first million in revenue, and we built a daily newsletter with over 100,000 subscribers. Harvard Business School teaches [a case study about Mattermark](https://www.hbs.edu/faculty/Pages/item.aspx?num=50356). It was the most fun and the most stressful thing I'd ever done, and it taught me almost everything I know about building teams. After Mattermark, I co-founded Holloway. We started with a question I'm still obsessed with: how do you help voracious self-learners teach themselves better? We built interactive digital books and I wrote [The Holloway Guide to Raising Venture Capital](https://www.holloway.com/g/venture-capital/about). The company didn't become what we hoped, but I learned a lot about writing there. Three companies in ten years. Each one taught me something different about building, leading, and knowing when to let go. ## Why coaching After ten years and three companies, a friend told me I'd be a good coach. The idea stuck because I knew what it felt like to not have one. When I was running companies, I desperately needed someone I could sit down with every couple of weeks and be really honest about what wasn't working. Not just the technical stuff, like how to hire or how to sell, but the inner stuff: the ego, the anxiety, the anger, all the stuff that was making me a worse leader than I could've been. I'm convinced I would've made a lot better decisions if I'd had that earlier. So now I do that for other people. I work with 15 to 20 startup CEOs at any given time, sometimes CTOs, sometimes the whole founding team. Half of what I do is teaching: the best practices of hiring, performance management, sales, team building. I'm a former operator, so I've been through a lot of this before: the hiring, the feedback conversations, the sales models, the compensation plans. When I was a founder in my twenties, I didn't know any of that stuff, and I wish someone had just shown me a pretty safe way to do it so I could practice. The other half is more like being an unlicensed therapist. You can know all the right things about hiring, but if your ego won't let you hire people smarter than you, that's going to keep being a problem until you figure out what's underneath it. I bring a lot of support, but I also bring a lot of challenge. If you're saying the same thing every two weeks and not doing anything about it, I'm going to call that out. A lot of coaches are all warmth. I'm here to help people become effective leaders, not just sit here and dissect emotions. That's great work, and a therapist can help you with it. Whatever you bring to a session, I'm working to make sure you leave it more effective than you came in. I coach because I'm trying to be the person I needed and didn't have, so that someone else's version doesn't have to be as hard as mine was. ## Management Craft The teaching half of coaching led me to a question: what if I could write down everything I teach and make it available to people I'll never meet? [Management Craft](https://managementcraft.co/) is my answer. It's a library of mental models and frameworks for management: the formal skills, the processes, and the mindset and inner game of being a founder and leader. But if I'm being honest, Management Craft also exists because I missed making things. As a coach, I love the work, but I missed the part of entrepreneurship where you're designing, building, shipping. Writing and design are the two things I've always loved most, and Management Craft is where I get to do both. It's my creative outlet and my way of taking everything I've learned and putting it somewhere it can reach more people than I can coach one-on-one. ## Over beers If you sat down with me for a couple hours, we'd probably talk more about philosophy and ideas than about startups. I love startups, but not for the reasons you might assume. I think they're one of the most amazing creative endeavors a person can take on. Not the spreadsheets and the revenue and the fundraising, though those matter. Startups are also one of the best places for curious, self-motivated people to come in and do real work. If you want to learn, there's no better container for it. What I love is that so many people starting companies are optimistic, kind of naive, but in a really endearing way. They're incredibly earnest. I want those people out there making companies and products for the world, because I think the world is better when they do. And I want to make sure the process doesn't kick their ass so completely that they end up cynical and angry and cruel. Part of what keeps people from going cynical is who they build with. The people you hire, the people you start with, the people you survive the hard years alongside can become your best friends for the rest of your life. There's something about making stuff with people that's hard to explain to anyone who hasn't done it. In college at Ohio State, I helped start a group called the Business Builders Club. We joked it was a drinking club with a business problem. We still text every day. My wife Kate is the Founder and CEO of [Keystone Bio](https://www.keystonebio.co), so this stuff runs through our whole life, not just mine. But sit down with me in person and I'd rather talk about what makes a good life, what we owe each other, and why making stuff with people is basically the whole point of being alive. I'm a humanist. I read a lot of science fiction. I play too many video games. [Get in touch](/contact). ## Interviews & Media You can find past interviews and media appearances [here](/media). If you'd like me on your podcast or at your event, [reach out](/contact). ### Media bio Andy Sparks is an executive coach who works with 15 to 20 startup CEOs at any given time. He spent a decade as a founder, co-founding Mattermark (a B2B analytics company that grew to $5M ARR and over 100,000 newsletter subscribers) and Holloway (a digital book publishing company). He raised over $20 million in venture capital, wrote [The Holloway Guide to Raising Venture Capital](https://www.holloway.com/g/venture-capital/about), and is building [Management Craft](https://managementcraft.co/), a library of mental models and frameworks for management. ## Coaching I do my best work at the inflection point: you've got wiggles of product-market fit, you're building a real executive team for the first time, and the job just changed underneath you. Yesterday you were building the product. Today you're building the organization that builds the product. I work with startup founders, CEOs, and their executive teams. Usually venture-backed, usually B2B software, usually somewhere between ten and a few hundred employees. ## What I bring Most coaches have studied startups. I've been a startup CEO twice (and a COO once). I've hired and mis-hired executives, navigated a co-founder split, and had board meetings that went sideways (and ones that went great). When you describe what you're going through, I'm not guessing what it feels like. That experience doesn't mean I'm here to replay my own playbook. It means I understand the weight of your decisions well enough to help you think more clearly about them, and then actually make them. ## How it works I don't follow a curriculum. I meet with clients over Zoom or phone, usually every two weeks, and sessions are about whatever's most alive. Some weeks it's a hiring decision. Some weeks it's a conflict with your co-founder. Some weeks it's "I don't know what I'm doing and I'm not sure anyone should let me run a company." I've been coaching since 2020. I work with 15-20 clients at a time and have coached over 60 people for more than 1,800 hours. If you'd like to learn more, [get in touch](/contact). For tactical answers, see my [Coaching Logistics page](/executive-coaching/logistics) (Fees, Cadence, etc.). ## How I think about coaching My job is to help you become a better decision maker, a better leader, and ultimately build a more successful business. That's the outcome. Everything else is method. Most coaching has an either/or problem. Pure "ask questions" coaches never give you an answer, even when you're a first-time CEO who's never seen what a good board meeting looks like. Pure advisory coaches give you the playbook, but you never develop the capacity to figure things out yourself. I do both, but the order matters. Every session, I'm running a three-step sequence. First, I **read** what's actually happening (not just the problem you walked in with, but what's underneath it, too). Is this a structural problem (your org design is creating the conflict), an interpersonal problem (you can't give hard feedback), or a personal one (your identity is threatened by hiring someone smarter than you)? Second, I **stay** with what I've found before reaching for a solution. This is the step most coaches skip, and it's where the real work happens. Third, I **offer** the intervention that fits: sometimes a question, sometimes a framework, sometimes direct advice from my own experience. The answer is rarely the bottleneck. Your capacity to use the answer is the bottleneck, and that capacity only develops if someone slows down long enough to help you build it. I'm not going to relieve a symptom and move on. When you bring me a problem, I'm going to help you fix it _and_ understand why it happened, so we're not fixing the same thing six months from now. ## Essays ### Drink the Radioactive Gatorade *Published: 2026-03-07* I posted something on [Twitter](https://x.com/andysparks) last week: "My best description of the current moment is that a small subset of the population just realized they can drink radioactive Gatorade and get superpowers, and everybody else is pretending it's 2019." A couple of friends have quoted it back to me in conversation since, which usually means something landed. But a few people also asked me what I meant. So let me clear that up. There's this moment in superhero origin stories where a regular guy encounters something radioactive: a spider, a vat of glowing chemicals they somehow survive, you know the drill. The point is that afterward, they have superpowers. Right now, there is some survivable radioactive gatorade sitting on the table for the drinking. A few of us have drank the gatorade. We have survived. And it feels like we have superpowers. I've been working in or adjacent to the tech industry for sixteen years. And I've never had more fun in my professional life than I'm having right now. The reason is a specific experience I keep having that I've never had before: I wonder if I can do something, I try it, and it works. I've always loved design but never _been a designer_. My friend Carrie says I can still call myself a designer though. Anyway, I'm probably a six or seven out of ten at it. There are countless people better than me, you know, real professionals. But because I invested enough skill points in design over the years, I have the language to tell a computer what I want it to make. And it makes it. By talking to it. And I don't get why people aren't floored when I tell them that. There's this explosive creative freedom to realizing you can just make stuff on your own when before you had to try to explain it to other people, write PRDs, have meetings, file issues in GitHub, and even argue to get something to show up in a browser just the way you "saw" it in your head. And it's not just designing and coding. I've also been playing around with how I write. When before I'd stare at my cursor as it taunted me with a blank page and a first sentence I'd inevitably hate, delete, and rewrite a million times, I now start by dictating ideas like I'm Churchill in bed minus the cigar and the day drinking. I dictate, I have Claude generate me a first draft. From there, the possibilities are endless. I can ask Mr. Claude to cross reference my draft with notes I've saved over the years, ask for academic research that challenges or supports my theories. I've also taken my five favorite books on how to be a great writer, had Ser Claude create condensed references for each in markdown, and now I ask, "If John McPhee read this draft, what might he say about it?" And then, "If Bill Zinsser now read my draft, what would _he_ say?" And it tells me. And I improve my writing. And most importantly, the whole time I'm just grinning ear to ear because it's so much goddamned fun. All of this runs on a $100-a-month subscription. I get that $100 isn't chump change, but it's also a hell of a lot cheaper than a $10,000 / month developer. Which I know is going to freak some people out, especially developers. I'll get to that in a second. But before that, there was this guy a while back who very few normies know about. This man was Doug Engelbart and he had a name for the radioactive gatorade, and that name was _augmented intelligence_. His vision was a future where we let humans do what humans are great at and let machines do what machines are great at. That's what this moment feels like when you're inside it. The machines are now really, really good at things that used to be expensive, that used to require hiring people, that used to take weeks. And that frees you up to do the parts that only you can do: the taste, the judgment, the weird creative instinct that says "what if I tried this?" So why is everybody else pretending it's 2019? I don't mean that in a judgmental accusatory way. I mean like, why might people not be getting this? People are looking at these tools through one of two lenses. The first: it's not actually that good. The only people saying that are the people who aren't using the best models. The frontier models are very, very good. The second: it's going to be so good that people are wondering where they'll get their income and, more existentially, where they'll find their sense of meaning and purpose. I have real empathy for both. I think about my own work every day. I'm a coach and an advisor to startup founders. How much longer until people would rather talk through their problems with an AI than with me? I use Claude for advice regularly. I understand the existential weight of watching a machine get better at something you've built your identity around. And I promised I'd come back to developers. If you've spent your career writing code, and writing code is a core part of how you think of yourself, I get why this moment feels threatening and disorienting. The shift from coding to coordinating agents and workflows is a big one. But at the core, I think, writing software was a means to make things. And making things is still very, very possible. More possible than ever, really. We can now augment our intelligence with Mr. Claude or Mr. Codex and build things at a speed and of a scope we could not six months ago. There's a classic argument that every major technological shift, from electricity to the internet, destroys some jobs and creates an explosion of new ones. There's a fear this time that this time is different. I think that fear may be well placed. I don't know. Nobody does. Maybe this wave will be like the others and lots of new jobs and wealth and consumption will come out of this. Perhaps Mr. Andreessen will be correct. Seriously, _who knows._ Really. I'm not here to call a verdict on whether we're heading toward something cyberpunk and dystopian or something solarpunk and expansive. But here's what I do know: right now, things are possible that weren't possible three months ago. Tools that six months ago cost tens of thousands of dollars and required you to hire people are now available for the cost of a nice dinner. Whether you want to learn, make, or build, there is pure creative power at your fingertips. You can choose not to drink the gatorade. And I want to be clear: there's nothing wrong with that. In every other technological revolution, we learned to make things with machines that we couldn't make before, and every time, the handmade version became more valued, not less. Nobody's table is handmade anymore, unless you're rich I guess. The people who still make furniture by hand are doing something admirable, and we pay a premium for it. Same with a handmade suit. Choosing to write without AI, to build without AI, to create entirely by your own hand is a legitimate and respectable choice. But if you're not making that choice deliberately, if you're just hesitant or a little spooked, I think you owe it to yourself to lean in and try. You might find you'd rather make things by hand. But I think you're going to discover complementary skills you didn't have before, access to tools that shorten the distance between an idea and a finished thing, and a feeling of creative possibility that is worth the couple of weekends it takes to find your footing. I don't know what the future holds. But anyone who thinks of themselves as creative and isn't leaning in right now is doing themselves and the world a disservice, by leaving beautiful things uncreated. --- ### The Awkward Adolescence of Ambition *Published: 2025-10-07* _Ambition is not willpower, hunger, or hustle. It is awareness, a noticing of something inside us longing to be heard and expressed, and a devotion to shaping it into something the world might, one day, be better off for having._ **I.** Every bakery, book, medicine, or movie started out in somebody's head as a craving to do something with their life that mattered. Creativity begins with an ambition. That craving, whether to open a restaurant, write a novel, or raise confident children, is part of what it means to be human. It's not corrupt to want to build. Nor is there any shame in having tried and gotten stuck. But to have nurtured an ambition, wrestled with it, and turned it over to the world, that is the stuff of satisfaction and a life well lived. But the word _ambition_ confuses us. In his 1828 dictionary, Noah Webster defined ambition as "laudable" but also an "inordinate desire for power." Aristotle taught that every virtue is a "mean" between two extremes: one of excess and one of deficiency. In excess, ambition becomes avarice, the lust for power at any cost, an ego-driven conquest. Too often, we fear the excess and discourage ambition altogether. Just because music _can get too loud_ doesn't mean we should silence it. In deficiency, ambition is replaced by hesitation, envy, and shame. Whether it's the first or the hundredth step, the challenge exhausts us. We decide not to take it. We too often watch others take the steps we haven't, however, and use that as further reason not to take them ourselves. Somewhere, deep down, parts of ourselves argue. _"We could do that,"_ is met with _"If we could, wouldn't we have?"_ There, between excess and deficiency, stands _virtuous ambition_. It begins as a yearning to be useful, to make something we can take pride in. It requires curiosity and patience to learn what our ambition really is. It is awkward and clumsy, like an amateur screeching on a violin, for years, if not decades. And then one day, after its adolescence, if we're lucky and keep at it, it becomes art. To welcome ambition, instead of spurn it, is an act of courage. To have _just enough_ belief in ourselves to wonder what we might create, and to try and do so, but also to summon the strength to resist the temptation of ambition's excess, that is where the virtue lies. But ambition doesn't arrive fully formed. At first, it comes faint, more static than signal, asking us to lean in, listen, and tune in. **II.** Some things in life _speak_ to us, even if they begin as a whisper, staying with us long after the moment has passed. Maybe it's the laughter in a courtyard or the sorrow we felt closing a book. Each fragment seems trivial in isolation, easily dismissed as a casual affection, bundled into a basket with all the other things we like. If we pay attention to what draws us, patterns emerge. Each interest feels like a part of a greater whole, a radio signal drifting in and out. Admiration, I've found, is a terrific guide. The books I've stuffed with post-its and highlights, the lectures I've replayed until my wife teases me, over and over again, I return to a collection of writers, humorists, designers, urbanists, psychologists, and science-fiction authors. All, deep down, are committed craftspeople, philosophers, and communicators. An ambition doesn't arrive overnight, and that should comfort us as we explore and play with what we love. Many times, with time and perspective, we see the things we chased with youthful conviction were not ends but means, not the whole melody, but ingredients. [Bill Watterson](https://twitter.com/calvinn_hobbes/status/1053347230696976384), the creator of the comic Calvin and Hobbes, said, "The truth is, most of us discover where we're heading when we arrive." I have that tattooed on my right arm. Finding your ambition is more remembrance than discovery. It happens slowly, then all at once. You feel as if every fiber of your being might be torn apart if you don't find a way to do this thing. To reject your ambition here is a prison sentence, and you are the warden. To embrace it is a reunion with yourself. Quiet. Seismic. Both overdue and right on time. An ambition is a lover who only you can reject but who cannot reject you. And I've spent my share of time in a cell. Since middle school, I was a writer unwilling to call myself one, spooked by the stereotype of starving for it. Instead, I put writing in service of other projects, misleadingly calling _those_ my real pursuits. For decades I kept turning the dial, toward, away, back again, _knowing_ in my bones that writing was part of who I am. But this tuning in is insufficient. Ambition demands we learn to play _in tune_, to share the thing we've fallen so deeply in love with, so others can hear it too. **III.** The work of developing an ambition is in making it legible: first to ourselves, then to others. Tuning in is private: catching a melody no one else can hear. Playing in tune is public: expressing that song so others can hear and hum it. The good news is if we're hearing the music we've done half the work. The _bad_ news is that we've done half the work. At the beginning, we finally work up the courage to tell our family the plan to make it big in Hollywood. We show them our first homemade film only to be met with blank stares. Silence, not cheers. It's hard to overstate how painful and awkward this part of the creative process is. We can hear the music, but we can't reproduce it. And we know it. We know it's not good enough yet. We make things, books, furniture, whatever, and for a long time they are proofs of our inadequacy. Most people quit here, and who can blame them? Carrying with them a mix of jealousy and respect for anyone who kept going, the chasm between their excitement and others' is just too far. Ambition is little more than a creative hypothesis. The many acts of outward expression, each an experiment, strengthen our inward clarity. We hear. We play. We adjust. Each time we realize we must not have quite heard what we thought we did. Hearing and performance sharpen together, refined by patience. But patience, too, though, needs discernment. Each experiment asks us to choose: press ahead, or change course? **IV.** There are two ways we meet the choice: with a **closed fist** or an **open palm**. The fist squeezes tighter, mistaking force for progress. The palm stays open. It listens, invites, adjusts. In the mindset of the closed fist, we push harder and convince ourselves that full calendars equal forward motion. In the mindset of the open palm, we journal, reflect, and accept intuition as data. The fist resists; the palm welcomes. With the fist, speed blinds. With the palm, we pause long enough to see whether our latest effort sharpens or distorts the melody. I can't recommend the closed fist. A decade ago, I started a company with someone my gut told me wasn't the right partner. I remember the moment I sat in a coffee shop and told him I didn't think we should work together. He made his counterargument, and in a moment of insecurity I ignored myself. I closed my fist. And so we spent four years circling the same unresolved arguments. Scientists run imperfect experiments, misled by their own expectations. The open palm notices the data; the closed fist argues with it. Difficulty, while unavoidable, is not a surefire sign we're on the right path. Some things are hard because that's the nature of craft. Others are hard because they're wrong for us. And the thing about that melody is that as we tune into it, we realize we are its composer. The call is coming from inside the house, and it is not finished being written. **V.** I began this essay frustrated. Favoring the open palm, I thought writing would help me tune into a clearer picture of my place in new urbanism. Instead, what I found was writing itself, the through-line I've kept in service of other ambitions, now asking to stand on its own. My inner critic tells me I'm quitting again, that I can't commit. But my regrets have never come from quitting too soon. They've come from forcing too long. Ambition isn't just a string of experiments. It's a devotion to making something meaningful. To press the wrong ambition is to choke off a part of ourselves, to abandon the search is to rob the world of something beautiful. Better a slow, meandering search than a premature declaration of victory. Ambition is not a destination. It's a way of being, a practice of attunement, of greeting what draws us with an open palm, not a closed fist. Intuition is imperfect, but it is the most reliable guide we're apt to find, if only we'd let it. And maybe that's all ambition ever asks, that we _listen._ --- ### This is the Work *Published: 2025-05-29* _There's no shortage of stories about who you should be. Some are handed to you with love, others not so much. A few you carve for yourself, only to wonder later if they were ever really yours._ _Over the past year, okay,_ **_four years_**, _I've been sorting through those stories. I've outgrown some, avoided others, and buried one so deep that when it finally resurfaced, it both broke the masks I'd been wearing and made me feel whole in a way I didn't know how to explain. Not to friends. Not even to myself._ _This essay came from trying to do just that._ **I.** Once a month, a group of guys in my neighborhood gets together for dinner and drinks. At the end of dinner, a new friend of mine, Matt, asked how my deep dive into education was going. He knew I'd been exploring the possibility of starting a school. I laughed and hesitated. I'd recently picked up a thread I'd buried too many times, but I didn't yet know how to put it into words. I told him I'd update him next time we had martinis. Later that week, my wife and I had dinner with an _old_ friend of mine. He asked the same question, wanting an update. As I began to explain myself, I felt a surprising deep sadness: I'd buried a part of myself so thoroughly, for so long, that even attempting to share it triggered a kind of antiviral response, from someone who I'd have said _knew me well._ **II.** For the last four years, I've been torn between two very different ways of being. The first is the mode of **the map**: where a clear and communicable professional identity reigns supreme. The map is top-down, label-driven, legible. Our identity, our labels, give us a sense of direction. In map-mode, I am an executive coach to startup CEOs, an author, and a former founder. Or: I'm all that _plus_ exploring the possibility of starting a private school. Got it. The second is the mode of **the territory**: where there is no script, only a pull, a hunch, a whisper. The territory is bottom-up, label-last (if ever). You have to _notice_ it. In the territory, I've realized I love coaching. But something's missing. I think of my professional life as 100 points I can assign. Coaching claims a wholehearted 30. I don't want to change that part. The remaining 70 stand in the corner, an elephant wearing a mechanic's coveralls, complete with its embroidered name, wondering if I'll ever put him to work. I've tried on various things for the elephant, writing science fiction, exploring a master's and PhD in clinical psychology, to name a few. But the more I've searched, the harder it's been to explain what I'm doing to others. The poet David Whyte wrote this: > "Ambition is desire frozen... The ease of having an ambition is that it can be explained to others; the very **_disease_** of ambition is that it can be so easily explained by others." When you look at a clock, you know it's a clock. When you look at a person, how do you know if they're a scientist, engineer, bartender, doctor, politician, welder, or painter? Well, they'll tell you, right? But that very norm, that we can _tell others_ who we are, creates pressure to declare it too soon. And that pressure is exactly what makes it harder to wander, listen, and keep exploring the territory until we hone in on what feels intuitively right. **III.** It's October of 2024. My wife and I landed the plane on two momentous projects: getting married in June and moving across the country in August. My quest to fill the remaining 70, temporarily put on pause, could finally be picked back up. I walked downstairs to stare at our bookshelf. Something about Bertrand Russell's _History of Western Philosophy_ felt more "right" than anything else on the shelf. I've always wanted to explore philosophy, so I decided to trust that. Sitting at the counter, I was struck by a theme in early Greek philosophers. They kept getting exiled. They'd then move to Italy and, naturally, started schools. A thought hits me, with even more "rightness" than the book on the shelf: maybe I should start a school. Knowing how little I actually know about education, I decide to trust the instinct, but also shore up my ignorance. I throw myself into a six month journey, complete with ordering piles of books, reading some, pinballing between footnotes, academic papers, and articles. It all pairs nicely with the increasing usefulness of ChatGPT. For the first time in my life, I have something like a digital Aristotle to tutor me. My sojourn through education brings me, fittingly, back to the Greeks. I encounter the source of the whole "first principles" idea I'd been attached to for years. Of course it's Aristotle: > "To know a thing's nature is to know its first causes and principles." I'd tried to read philosophy before, but I always abandoned it, finding it too dense, too opaque. I always felt like I was absorbing 20% of what I read. "Maybe it's because I went to state school," I'd think. But with Chat GPT, I decided to take a page from Feynman: > "I don't know what's the matter with people: they don't learn by understanding, they learn by some other way, by rote or something. Their knowledge is so fragile!" So I stopped myself from moving forward until I _really_ understood what I was reading. I'd ask question after question until I felt that inner sense of clarity, of really _getting it_. And in one of the more meta moments of my learning, I discovered the Greeks had a word for that feeling: **nous**. Even better: I discovered it _while_ learning about _nous_ itself. I had nous about nous. With nous as my new bar for understanding, and Chat as my Socratic guide, I found myself genuinely enjoying rediscovering Greek ideas. A number of them stood out, but one in particular stood out, and serves as a perfect segue to the next part of our story: **mousike**. The Greek's idea of Mousike is, yes, where we get our modern idea of music from. But what we understand as music is a shadow of what the Greeks meant. To them, mousike wasn't just rhythm, song, sound, or melody. It was the cultivation of _taste,_ a critical part of a young philosopher-king's education. It trained you to notice what you like, what you don't like, what feels right, what _pulls your attention._ And just like that, I had another word for what had been quietly guiding my search for the missing seventy. **IV.** When I was a kid, my Dad was generally a _"we don't hire contractors"_ kind of guy. So I ended up tiling floors, pouring concrete, planting trees, running electric, and even once electrocuting the poor guy (only mildly, thankfully). All these projects helped me begin to notice how some spaces _just feel better_ than others. A yard full of trees, flowers, and a fire pit felt richer than a minimalist lawn. A wood-paneled, warmly lit room laden with leather furniture did something to the soul that millennial gray linoleum and sheetrock never could. I didn't realize it then, but I was developing a kind of _mousike_, a cultivated taste, for physical space. That love stuck around. In the ten years I lived in San Francisco building software companies, I found myself always noticing buildings, neighborhoods, and how thoughtful design could transform a place. I'd go on walks and lose my train of thought imagining how a street would look if only there were more brick, more trees, bustling ground-level shops, restaurants, and one of my favorite features: [bioswales](https://en.wikipedia.org/wiki/Bioswale). Over and over again through the years, I'd arrive home from a walk a little let down, disappointed that these ideas lived only in my imagination. Steven Spielberg said: > "The hardest thing to listen to, your instincts, your human personal intuition, always whispers. It never shouts." My intuition always called me to make things in the real world, but it whispered. I let myself get caught up in the shouts of the digital gold rush. I molded the part of me who liked to make things to fit the digital world, occasionally finding time to design this or that, even without any formal training, and often with dull-blade precision. Looking back, a big part of me wishes I'd fed my inner designer more heartily while I was working on startups. I never became world-class, I never designed a production-ready product from start-to-finish, I didn't ever invent anything. Instead, I learned to sell, hire, manage, fundraise, and write. David Whyte, the same poet, also said: > "No matter the self-conceited importance of our labours we are all compost for worlds we cannot yet imagine." There's a few ways to interpret that, but I think the idea that whatever we're doing now is fertilizing soil for unimaginable new things to grow from is beautiful. My flirtation with the physical world continued, but my time in San Francisco was valuable. In many ways, it was an exercise in keeping doors open, collecting practical skills I could re-apply elsewhere down the road. **V.** In 2020 I left my role as CEO of Holloway. We'd hoped to build a product that enabled our users to ask books questions, opening up a new horizon of possibility for the curious. We didn't deliver, but thankfully others did. One of my favorite writing tools now is to upload William Zinsser's _On Writing Well_ to Chat, give it my draft, and ask it what Zinsser would say about how to improve my writing. Failing to deliver on our ambitious goal, combined with a pandemic, left me feeling burnt out. A close friend suggested I take a beat and try my hand at coaching other founders. Colleagues had always told me I was a great listener, something I'd never thought of as a technical skill like design is. As it turns out, listening is definitely a technical skill and a rare one at that. On top of leveraging a strength, building a coaching business presented me with an opportunity to build a business all by myself. At a moment when I'd been rattled, I was left wondering if Holloway's lack of success was _me._ I figured if I were entirely incompetent then I'd crash and burn. Instead, my coaching business thrived. As I settled in to a strange new identity of advisor to startups instead of an operator, I set out to be the best I could. I identified a list of coaches people considered to be "the best," met them or read everything they'd written, and while I didn't always walk away unimpressed, I often did. Somewhere along the way, I came across a wonderful book: _Greatness_ by Dean Keith Simonton. As a coach to CEOs who wanted to be _great_, I figured it would be worth my time to learn what the research had to say on the subject, and Simonton's 500 page review of the scientific literature did the trick. One line stood out to me in particular: > "...we might do better to say that all the motives that can stimulate the energies of the human being all converge on a single activity, a monomaniacal preoccupation." "What am I monomaniacally preoccupied with?" I thought. My work with clients was, and continues to be, a mix of "outer work" (practical how-to advice: e.g., how to build a great hiring process, and so on) and "inner work" (emotional exploration: e.g, if you're afraid of hiring people smarter than you, no hiring process will help). I began to notice which parts of my work stayed with me, which parts left me curious to learn more. After a year or so coaching, I knew I had room to grow in the latter skill. Clients will often ask me, after working together for a while, if we can spend a session talking about some difficulty with their spouse or significant other. I always emphasize that I'm not a therapist, but I'm happy to listen. This happened so often I decided to spend a year learning first about couples therapy and marriage counseling (it turns out a lot applies to executive teams and co-founders) and later psychodynamic psychotherapy. I seriously considered applying for a masters program with the goal of getting a PhD in psychology. For a few years, I repeated a cycle from curiosity to study to application, and working with people began to feel like a real craft. In June of '23, I came across this quote, by Richard Hamming: > "What are the important problems of your field? What important problems are you working on? If what you are doing is not important, and if you don't think it's going to lead to something important, why are you working on it?" I love coaching founders not because I believe it's one of the most important problems in the field of psychology, but because of each of my relationships with the individual founders feeds my soul. It's the relationships, stupid. It's helping people where I didn't have help. It feels like _healing_ to help people avoid some of the mistakes I made, to be there for them when I didn't have someone. These founders are all so earnest, curious, motivated, creative, and want to do some good... maybe not all founders, but the ones I work with are. And helping these people get where they want to go feels great. But the longer I coached, the more I realized it didn't scratch every itch I had. I still wanted to build again. **VI.** In May of 2024, a CEO client asked me to facilitate their off-site. I figured I'd have some downtime to read, so I stared at my bookshelf (again) and waited for someone to raise their hand. Years earlier, my co-worker, Hope recommended I read _A Timeless Way of Building_ by Christopher Alexander. I'd bought it, but I never opened it. For some reason this book stood out. I threw it in my bag. The Urban Cowboy lodge in the Catskills is terrific. It sits on 200 acres of grassy hills and woods complete with fire pits, cabins, and a sauna all wrapped up in a mix of country and Brooklyn hipster. After wrapping up a day of facilitating, I headed to my room to sit in a luxe wooden soaking tup on my cabin's patio, poured an old fashioned, and opened up _A Timeless Way of Building_. At Holloway, our editor and now my dear friend [Rachel Jepsen](https://www.racheljepsen.com/) recommended I watch _The History Boys_, a comedy about a British headmaster's attempts to turn eight rowdy students into university-ready gentlemen. In one scene, the headmaster, played by Richard Griffiths says to a student: > "The best moments in reading are when you come across something, a thought, a feeling, a way of looking at things, which you had thought special and particular to you. Now here it is, set down by someone else, a person you have never met, someone even who is long dead. And it is as if a hand has come out and taken yours." Reading _A Timeless Way of Building_ was exactly like that for me. I texted my wife, "I think I want to build a neighborhood." And it was only while writing this that I remembered I'd told her that once before, in 2021 while sitting at Flour + Water in San Francisco, eating their perfectly square layered lasagna. They took it off the menu soon after, one of the worst acts of value destruction I've ever witnessed in the restaurant business. The quote that stood out to me most from Alexander was: > "The life of a house, or of a town, is not given to it, directly, by the shape of its buildings, or by the ornament and plan, it is given to them by the quality of the events and situations we encounter there." I flew home from New York _knowing_ what I wanted to do. I couldn't precisely articulate what it would look like, but I knew I wanted to play with physical space in a way that enabled the kinds of experiences that make people come alive. And then life called. A few days later, Kate and I packed our bags for Europe for our wedding and honeymoon. The elephant would have to remain unemployed once again. **VII.** Kate and I are sitting in an Irish Pub in San Sebastian. The table is sticky, it's raining outside, and I wanted a beer. We've been in Europe for nearly a month. We both know we want to start a family at the end of the year, and we know we don't want to do it in San Francisco. In part of my wedding speech welcoming our guests, I said: > Because, while a wedding is about two people, it's about making sure we have _enough people_ too. This wedding, this feast, this trip, all the hard work that has gone into this, is not just about Kate and I getting married, it's our way of saying thank you for being there for us. We knew we wanted to surround ourselves with great people wherever we went next. And for whatever reason, we had a group of friends in a hundred year-old village Christopher Alexander might admire. So that's where we went. Originally, we meant to buy a house, and I planned to use it as my laboratory to develop another type of knowledge the Greeks had a word for, **techne**. I'd renovate our house by hand, just as Dad and I had, and in doing so I'd be ready to do it for others. But we didn't find anything we loved enough, so we decided to rent. After we moved, decorated, and settled in, I sat down at my desk. I felt lost. And that's when I went downstairs and picked up Bertrand Russell's _History of Western Philosophy._ One way of looking at my exploration of philosophy and education as a distraction. But more and more, I'm pretty sure it was just more compost. **VIII.** A few weeks ago, I walked on the brick sidewalks in my neighborhood appreciating that someone had the good sense to plant an abundance of lilac bushes. I walked by two houses I've walked by dozens of times, but something stood out I never noticed before. At one point in time, these two houses were identical. Today, much less so. It reminded me of the cover of [_How Buildings Learn_](https://bookshop.org/p/books/how-buildings-learn-what-happens-after-they-re-built-stewart-brand/9683207) by Stewart Brand. One of the two has stood out to me repeatedly, tastefully renovated and added on to, and the owners have taken hobbit-level care of the lush landscaping. My kind of house. The house next door looks like it needs some love. I begin to wonder. Wouldn't it be fun to work on the house next door or one like it? At this point, I've told almost everyone close to me that I think I'm going to start a school. I have a website built for a podcast I'm going to start to learn more about education. I have a whole strategy. But I get home after walking by these houses, and "Are we going to do this or not, man?" The whisper asked. A day or so later I'm walking by the same pair of houses with Kate. I point them out, tell her what I saw. She gets it immediately. I go home, I do some research. This is doable. I send photos of the houses to my friend in California who builds luxury homes (like, $20M homes luxury homes). He's been to German Village. We talk for an hour. I'm fired up. Instead of buying a house, living in it, and doing it all myself, I can leverage all the skills I learned in Silicon Valley: hiring, building a team, running the numbers, and even a mix of the _taste, the mousike,_ I'd cultivated for neighborhoods that feel alive. The idea of "flipping" a house as a passive investor makes me feel sick, but guiding a team, thinking of renovating a home as a "product" to craft feels closer to art and play. Countless times have I had thoughts that I smothered and suppressed. Walking past the architecture building at Ohio State (it's grotesque, by the way), "Maybe I'd like to be an architect." Sitting on a Piazza in Italy or seeing the courtyards in Barcelona: "If we can bring European coffee to America, surely, we can bring _this_ here, too?" And then I'd talk myself out of it. But this time something different happened. I didn't talk myself out of it. I leaned in. I tore up the map I'd been making for myself, embraced the territory. And what I found wasn't surprising. To craft a heartfelt home is a small part of building a community that feels alive. I'm confident the act of building will lay more compost, from which maybe a neighborhood will grow, maybe more houses. Maybe something else, not buried like a secret, but like a seed. **IX.** Knowing yourself begins by listening to yourself. And after four and a half years sharpening my ability to listen to others, I suppose it's no surprise that skill eventually turned inward toward whispers I'd spent years muting. Finding professional _nous_, real clarity, to _you_, about what you want to contribute to the world is an act of exploration. And to explore is to get lost at sea and find your way back, often becoming more you along the way. But once you've found your way back, finally set on a course that feels _right,_ there's a special kind of sadness that comes from having buried a critical part of you so effectively that it comes as a surprise to even the closest of your friends. And just when you finally stop burying that part of yourself, your friends step in with the shovel. David Whyte, again: > "The antidote to exhaustion is not necessarily rest... the antidote to exhaustion is _wholeheartedness... You are so tired through and through because a good half of what you do here in this organization has nothing to do with your true powers... You are only half here, and half here will kill you after a while."_ It takes discipline to even _aspire_ for wholeheartedness. It takes orders of magnitude more to find it and to commit to it. I spent eight months exploring the idea of building a school. I had a strategy. I was ready to begin. And then, just as I reached the starting line, something more wholehearted interrupted. The throughline wasn't surprising. A school, a home, a neighborhood, they're all just excuses to build community. The school: ambitious, exciting, needed, felt good. Building homes and one day neighborhoods: near-perfect occupational nous, impatient with waiting, ready for its moment. **X.** Ever since I can remember, I've loved RPG video games, story-driven adventures where your character grows through a mix of "main quests" that advance the plot and "side quests" that build your skills. In those games, the difference is obvious. The quest log tells you what's important. Real life isn't so kind. There's no blinking arrow above the next right thing. The paths forward exist only in your head, and their meaning lives in your heart. The "side quest" into education led me to the Greeks: mousike taught me to notice, techne to practice, nous to trust the feeling of rightness. It helped me recognize what I'd been silencing, and choose to embrace it. If you learn to listen, to trust the whisper, to follow what pulls at you, you may not know if it's a side quest or a main quest, but you can be sure it's yours. --- ### Exceptional People are Wonderful and I'd Like to Have More of Them *Published: 2025-04-04* Every day I'm grateful for the opportunity to work with, to coach, advise, teach, exceptional people. They are ambitious, bright, hard-working, creative, inspiring, and they love to learn. So here's a question that's chased me like Tom on Jerry: are exceptional people rare flukes we're lucky to stumble across, or are there a lot more of 'em out there, just waiting for a bit of sun? And boy, wouldn't that be something? So indulge me: exceptional people are wonderful, and we'll be better off with more of them. Do people who do really good stuff have flaws? Of course. But I know I'm better off because of the exceptional editor I've had a chance to work with (her name is Rachel). I'm better off for having had an exceptional professor in college (his name is Artie). My city is better off for having had an exceptional ice cream maker (her name is Jeni). Those are a few everyday exceptional people, not to mention the men and women who made the allergy medicine that makes it possible for me to go outside in the spring and fall without sneezing sixteen times in a row or the doctors who saved my life at three and a half when my doctor misdiagnosed my burst appendix as the flu. Exceptional people make the music, the medicine, the restaurants, the poetry, the paintings, and the airplanes. But exceptional people make us _uncomfortable._ They give us the willies. As _exceptions_, we have to admit their capability sometimes exceeds others' (and most importantly, _ours_). Kind of makes you feel insecure, right? They're better than us at some things, but just because a doctor is a great doctor doesn't mean she's a better _person_ than an average mechanic. Last I checked, doctors need mechanics, mechanics need doctors, and both would prefer the other to be exceptional. But man oh man, that does not make it easy to talk about what we do about crankin' up the ol' exceptional person factory to eleven. We often conflate being exceptional with being lucky, born rich, connected, or privileged, but hey, did you know less than 7% of the variation in SAT scores can be explained by family income? Exceptionality does not have to be synonymous with wealth or privilege, and investing in exceptional people need not be a zero-sum game where we're robbing the disadvantaged to invest in excellence. Now I don't know about you, but I'd like to live in a world where two things are true: (1) we don't hold exceptional people back (we encourage the hell out of them) and (2) exceptional people use their gifts, at least to some extent, to make sure quality of life improves not only for them, but for all. How do we do that? Well, that's something I'm thinking a lot about lately. So stay tuned. ## On the Personal Front They smell even better than they look. Lately, I've been thinking about how lucky I am to live in what I feel is an exceptional neighborhood: German Village in Columbus, Ohio. It's on the register of historic places, with mostly brick houses on mostly brick roads and zoning that allows for restaurants and a bar here and there. It's pretty and I knew it was pretty when we moved last fall. But as nature unlocks for spring, I'm feeling particularly grateful for _how well-gardened_ our neighborhood is. Only a couple of weeks into spring, and I'm realizing how stunning our streets really are. They're lined with magnolias, white, light pink, and deep pink verging on purple, and wow, do they smell good. Hyacinths pop up everywhere, alongside bright yellow forsythia bushes, pear trees, and a number of other plants with a penchant for colorful bravado in the spring. ![Magnolias in German Village](/images/essays/magnolias.png) Yes, spring is pretty. But man, it's wonderful to _see_ the culture of a tiny 233-acre neighborhood. We've all decided this is going to be an exceptionally pretty neighborhood, and everyone is on board. Maybe we can have nice things, after all. ## Recommendations - [**The Headmaster**](https://www.amazon.com/Headmaster-Frank-L-Boyden-Deerfield/dp/0374514968): You don't have to have an interest in education to enjoy this wonderful portrait of Frank Boyden, former Headmaster at the legendary American prep school, Deerfield Academy. Oh, and it's written by Pulitzer Prize-winning John McPhee, one of the ol' grandads of narrative non-fiction. It's a beautiful story, and one chapter's end caught me so off guard it had me sobbing in my reading chair. - [**The First Class**](https://www.thefirstclass.org/watch-player?submissionGuid=7301d37f-1795-42be-bed1-338ce5984e67): You won't find this documentary on Netflix. Why? Beats me. The First Class tells the story of, well, the first graduating class of Crosstown High, an alternative education charter school, in Memphis, TN. It's a heartwarming story that shows the benefits (and drama) of enabling high schoolers to take more ownership of their education. - [**Alpha School**](https://www.forbes.com/sites/rayravaglia/2025/02/10/alpha-school-using-ai-to-unleash-students-and-transform-teaching/): Look, I wouldn't put a link to the godforsaken hellscape that is [Forbes.com](http://forbes.com/) unless it was about something really cool. [Alpha School](https://alpha.school/), founded by MacKenzie Price, is a collection of schools built on Price's unique methodology: two-hour learning. Kids learn everything they need to score in the 99th percentile (and do) on state exams in two hours via _an artificial intelligence tutor._ After that, since parents don't want their kids home after two hours, the school focuses on developing life skills, "From public speaking to coding, entrepreneurship, and outdoor education, these experiences build grit, creativity, and adaptability." Anything with AI slapped on it should come with some healthy skepticism, but this stuff seems like... _it works_. - [**Paul Revere (with Gregory Alan Isakov)**](https://open.spotify.com/track/6BTAzOm96NwuGXhfHqWYM4?si=29386f4d005e4db3): I recently discovered Noah Kahan, who apparently was nominated for a Grammy twice. This is a beautiful song for starting up the morning with a nice cup of coffee. --- ### The Compound Interest of Books *Published: 2025-02-06* There's an unexpected upside to my bad habit of buying too many books: when they all sit unread together, they create a kind of natural selection environment where the truly compelling ones emerge over time. What seems like overconsumption actually enables better choices - as the books compete for attention, one will suddenly *jump out* as obviously superior to all the others I thought worth buying. This process of a book demanding to be read reminds me of what psychologists call *salience*, that quality that makes something stand out. But I prefer Noah Webster's 1828 definition: "*leaping; moving by frogs; as frogs; beating; throbbing; as the heart; shooting out or up; springing; daring; as a salient sprout.*" Some books, then, are quite literally (a fun word since we're talking about *books*) *leap from the shelf*, begging to be read. It's quite possible that every time I think of buying a book I could instead put it on a list and then, when I'm ready for a new book, look at the list and order the one that feels the most interesting. But I've tried that, and it doesn't work the same way. Maybe it's the choice of font on the spines of the books, maybe it's the books' width side-by-side, or maybe it's something about being able to pick one or two up and read a page or two (in practice, though, I never do that). What's really happening, I suspect, is a kind of attentional *compound interest*. Each time I pass by a book, plopped on a counter, flaunting its cover on my desk, shoved in a corner, or neatly stacked on my shelf, it catches my eye. Some books slowly fade into the background, but others get more interesting with each glance. A recent book I loved, "Why Greatness Cannot Be Planned," sat in various places in my office for weeks. "*Why can't greatness be planned?"* I found myself thinking as I passed it, turning the lights out for the day. The real challenge has been learning to trust the process, to quiet the utilitarian voice asking, "Why this book? What will it teach me? How will this make me better at my job?" I learned to let those questions go. A book's persistent ability to catch my interest is reason enough to read it, as I've been rewarded time and time again with discoveries even the books' titles hadn't clued me into being in the cards. Interestingness, it turns out, is both destination and journey: it's pleasure enough in itself to find something out, and it also plants seeds that might flower into something else entirely months or years later. Or not. And that's okay too. ## On the Personal Front Flyover country. My wife and I just made a move that might seem counterintuitive: after twelve years in San Francisco, we chose Columbus, Ohio as the place to start our family. No, we don't have family here. No, we didn't move for work, we both run remote businesses. We moved because we found something rare: a chance to design the life we actually want, not the one we're supposed to want. What drew us to Columbus? A group of close friends from my Ohio State days who've created something special here. They all live within a ten-minute walk of each other in a historic neighborhood, where brick houses and streets mix with coffee shops, restaurants, and a Jeni's ice cream parlor that feels built into the community, not dropped into a strip mall. Oh, and they're all starting families too. We considered staying in San Francisco or moving to New York, they both have obvious attractions. But they also come with a financial treadmill we realized we could simply choose not to step on. When I catch myself worrying what people might think about us moving to "flyover country," I remember: anyone who'd judge us for prioritizing friendship, financial freedom, and creating ideal conditions for parenthood can shove it. ## Recommendations - Neal Stephenson Series on Wrongness: First of all, the author of *Snow Crash, Cryptonomicon, Seveneves, Anathem, The Diamond Age,* and others has a substack. I only recently learned that. Second, he's been writing a series on wrongness, and it's fantastic. Just read it. Especially with all the hot opinions going around right now. Start with: [Wrong 1](https://nealstephenson.substack.com/p/wrong-1), and you can find the full series [here](https://nealstephenson.substack.com/archive?sort=new). - [Why Greatness Cannot Be Planned: The Myth of the Objective](https://www.amazon.com/Why-Greatness-Cannot-Planned-Objective/dp/3319155237): It's popular wisdom that goals are Good. But what if they're not? What if everything you know about achieving big audacious goals is wrong? It turns out, everything you think you know *might be wrong*. This was a short, fun read and it challenged how I think about how I spend my time. I think you'll like it. - [Work Zones](https://x.com/0xAneri/status/1863682276564893700): This is a great practical way of thinking about effort at work. With the rise of Andrew Huberman and Peter Attia, it seems like we're all aware of heart rate zones now. Zone two cardio: all the rage! What if we applied the five heart rate zones to work? Some weeks would be zone 0 weeks: vacation! Others might be zone 5: no personal life, working nights and weekends. I've found this helpful for teams to have shared language, and I've also found it helpful with my wife to set expectations for the week ahead. ![Flyover country](/images/essays/flyover-country.png) ## From the Archives In [*Hilarious Mistakes*](/essays/hilarious-mistakes), I wrote about looking back with fondness on the silly things we've done in the past not with shame, but amusement and appreciation for letting them teach us what we've needed to learn. --- ### If You Want People to Remember, Tell a Story *Published: 2024-08-27* In my work as an executive coach to startup CEOs, founders, and executives, I too often see leaders get frustrated and disappointed when their team fails to understand or embody a core value. But when you're at the top, you have to take responsibility. If your team isn't living the values, it's on you. You need to take a different approach. While docs and slides with values are a great starting point, I've found one way to increase the odds that people will "get" your core values is to attach them to stories. So instead of me _telling_ you why a good story is valuable, let me show you. ## [A Message to Garcia](https://en.wikipedia.org/wiki/A_Message_to_Garcia) The year is 1898. Edison is the time's Elon and "startups" build on electricity instead of internet. The telegraph is only a half century old, the lightbulb freshly twenty, and the telephone barely a teenager. It is the installation phase of the third industrial revolution, the "age of steel, electricity, and heavy engineering." The day is April the ninth. President William McKinley will declare war in twelve days, marking the start of the Spanish-American War. In [Elbert Hubbard](https://en.wikipedia.org/wiki/Elbert_Hubbard)'s, A Message to Garcia, the President needs to get a message to General Calixto Garcia, the leader of the Cuban rebels. Someone recommends First Lieutenant Andrew Rowan, "[He] will find Garcia for you, if anyone can." Hubbard paints a heroic portrait of Lt. Rowan. First, and perhaps almost as important as his eventual delivery of the letter, when asked to deliver the letter, Rowan does not ask, "Where is Garcia?" Or any other "idiotic" questions. Instead, the Lieutenant takes the letter and forever the good soldier embarks on his mission. He arrives in Cuba via dinghy, traverses the Cuban jungle, and risks hostile territory full of armed combatants. It would yet be forty years until The Wizard of Oz, but Hubbard's description conjures images of lions, tigers and bears. Rowan delivers the message. He is a man who will "do the thing." The story of Rowan's eager, willing, and capable delivery of a message to Garcia takes up a mere quarter of Hubbard's two page essay, however. In the remainder, Hubbard decries the state of the average American worker. Hubbard dares the reader to ask anyone in your office to write up a brief memo on the life of Correggio, an Italian renaissance painter. Hubbard suggests that, instead of the average worker "doing the thing" and writing up a memo, they'll ask a series of questions they should be answering on their own: > "Who was he? Which encyclopedia? Where is the encyclopedia? Was I hired for that? Don't you mean Bismarck? What's the matter with Charlie doing it? Is he dead? Is there any hurry? Shan't I bring you the book and let you look it up yourself? What do you want to know for?" Hubbard's tribute to the rare reliable man was a hit with numbers likely in the millions. Thomas Edison apparently loved it so much that he adapted the story for a silent film in 1916. It was again adapted for the screen in 1936. The phrase, "to carry a message to Garcia" became common enough as a rallying cry for leaders in search of their Rowan that even President Richard Nixon uses the phrase on the Watergate tapes. "A Message to Garcia" is achievement rhetoric at its finest, something we could use more of. The piece is an homage to the rare reliable man who "does his work when the 'boss' is away... when given a letter for Garcia, quietly takes the missive, without asking any idiotic questions," and does the thing assigned. Hubbard's conclusion to the tribute is rousingly poetic: > "Civilization is one long anxious search for just such individuals. Anything such a man asks will be granted; his kind is so rare that no employer can afford to let him go. He is wanted in every city, town, and village - in every office, shop, store and factory. The world cries out for such; he is needed, and needed badly - the man who can... carry a message to Garcia." Founders are capable of getting a message to Garcia. It's what makes them founders. As Hubbard says, civilization is built on and depends on founders getting metaphorical messages to Garcia. Messages that, when delivered, usher in waves of technological progress. But at some point, founders need to find other men and women to deliver messages to Garcia. They need executives, managers, and individual contributors who, when given a task, complete the task without questions. They do the thing. In the madhouse pressure cooker environment of running a startup, too few CEOs, founders, and executives recognize the power of a story to set expectations. They pop a value like "ownership" up on a slide in an all-hands and expect people to get what it means. Some might. Many won't. Instead, take ten minutes. Tell the story of Garcia. Let it be known that any and all who can carry a message to Garcia on your team will be rewarded, because that is what ownership and reliability look like. After all, the message you're responsible for getting to Garcia is building a team capable of getting their messages to their Garcia. ## On the Personal Front ![Kate and Andy at their wedding](/images/essays/married-ratatat.png) Kate and I celebrate as we walk to the head table to the tune of Ratatat's [Loud Pipes](https://open.spotify.com/track/3qkFIjYRInFasy2jeDZPgm?si=c22777bb349143e7). On June 12th, I married my wife, Kate on the island of Crete in Greece. Eighty of our favorite people, family and friends, joined us to celebrate. Kate and I almost went the low-key city-hall route, but decided to go big instead. And we're so glad we did. One thing that I've gone over and over about in my mind since is the value of making a big deal out of things that are a big deal. Taking the time to write speeches, design the set list, dress like we mean it, hear each others' thoughtful messages to one another, and cry and embrace our parents as they did the same was something I'll never forget. Similarly, my grandfather passed away last year. We didn't hold a funeral for him for nearly a year. Rites of passage exist for a reason, and when we do away with them, delay them, or minimize them, we do ourselves a disservice. So whether it's a wedding, a funeral, a launch party, a celebration for hitting this month's number, or recognizing whoever at the company carried a message to Garcia, get everyone together and mark the occasion. ## From the Archives [Why We're Unprepared for Co-Founder Relationships](/essays/issue-16-why-co-founders-struggle) As an executive coach to startup CEOs, founders, and executives, I see more than my fair share of co-founder conflict. At some point last year, I decided to sit down and write some thoughts on why so many co-founders end up at each other's throats. In this piece, I contrast how we get into relationships with co-founders with how we go about dating and eventually getting married to our life partners. Given that Kate and I just got married, I figured this was an apt time to bring this one out of the archives. ## Recommendations - [The Mercy of Gods](https://www.amazon.com/Mercy-Gods-Captives-War/dp/031652557X) (The Captive's War #1): I am a huge science fiction fan. I've read almost every Hugo and Nebula award winning book. The Mercy of Gods is a true five-star worthy book. It's the first in what will be a trilogy written by James S.A. Corey, the pseudonym adopted by the two authors also behind The Expanse. This book, a space opera on a truly grand scale, left me both haunted and surprisingly grateful in ways that caught me totally off guard. As I de-planed last weekend around the 80% mark in this book, it was like I was seeing the world with new eyes. - [Sparkly People and How to Find Them](https://anson.substack.com/p/recognizing-sparkly-people-without): This short read on qualities the author, [Anson Yu](https://substack.com/@anson), looks for in friends really made me smile. I instantly sent it around to several friends. "This is like what we look for!" I particularly loved criteria like, "Hype Adjacent" and "Relationship with Useful Vices." --- ### Get Beyond Treating Symptoms: Identify Root Causes *Published: 2024-02-13* As an executive coach, I help people get _unstuck_. And after three years and 1,400+ hours with clients, I wanted to take a minute to share a bit about how I do that. With this post, I hope to equip some people to solve their problems. On top of that, I'm also hoping to provide a way of thinking that will help you work more effectively with any caregiver (e.g., couples therapists, physical therapists, executive coaches, etc.). All of us get stuck. We struggle. We thrash with coworkers, parents, spouses, siblings, BMW drivers who don't put their damned blinkers on, and the guy at the bagel shop who always puts red onion on when you ask for your lox without. On top of that, accidents happen, our bodies ache, and we lose people and parts of ourselves. Some of our difficulties lie outside of the realm of solutions. Resurrection is out of the cards, COVID isn't returning to the raccoon dog's underground laboratory, and you can't unsay that dumb thing you said at work. But how we _react_ and _adapt_ to the parts of life we wish we could disappear or undo is often within our grasp. The key lies in differentiating between **symptoms** and **root causes**, and you can work through just about any problem by following the following five steps: 1. **Identify the symptoms** 2. **Relieve the symptoms** 3. **Diagnose the root cause** 4. **Treat the root cause** 5. **Create a Prevention Plan** (i.e., avoiding "re-injury," relapse, or recurrence). This works at work, and it works not at work. It _just works_. But since abstractions are dull and less memorable, let's apply this process to a few examples. Imagine you have a headache. 1. **Symptom Identification**: What are your symptoms? Easy. Your head hurts. 2. **Symptom Relief**: Take two Advil liqui-gels and think to yourself, "For all the shit I give the pharmaceutical industry, Advil _is pretty legit_." Wait 30-60 minutes, and feel better (hopefully). 3. **Diagnose the Root Cause**: If you take Advil for every headache, your stomach will start bleeding. So what's the root cause? You'll need to run some experiments. A quick chat with your sister, the nurse, leads to a hypothesis: "I might not be drinking enough water." 4. **Treat the Root Cause**: You drink a big glass of water twice in the morning and twice in the afternoon. Your headaches go away. 5. **Create a Prevention Plan**: You buy a new water bottle and tape a sticky note to your monitor, "Say No to Headaches, Drink Water." You stick to the plan, listening to the almighty sticky note, and months later, you think, "I can't believe I accepted headaches were a part of daily life for so long." Roll credits, applause. "Okay, Andy, this is a basic example my fifth grader could have walked me through. Help me solve something gnarlier, like the employee on my team who isn't pulling their weight." Okay, let's try that. 1. **Symptom Identification**: Employee X's work is constantly late and of mixed quality, and their attitude is a bit off. The department isn't hitting its goals. All of this makes you feel angry, confused, and sad. You don't like feeling that way, and if the department was hitting its goals, the company would perform better. That board member would stop harassing you, and you might finally be able to take a vacation. 2. **Symptom Relief**: You yell at your dog when she wakes you up to go outside at 5am, you write a sternly worded Slack message to Employee X about their "disappointing performance," you tell Employee X's manager they need to "solve it or else," or you decide to fire Employee X. 3. **Diagnose the Root Cause**: Again, you can't keep doing whatever you choose in Step 2 without ugly consequences. So, you will need to develop a hypothesis around what's _going on_. Maybe Employee X's Mom has cancer. Perhaps you haven't set clear enough written expectations in writing. Maybe you're skipping 1:1s. Maybe Employee X is working really hard but afraid to ask for help. Maybe they're just a lazy sod, and your hiring process doesn't weed out lazy sods. 4. **Treat the Root Cause:** After reading step 3, you realize you aren't doing 1:1s and don't have clear expectations written down, so you decide to implement a more rigorous and structured 1:1 approach like [Dave Kline suggests here](https://twitter.com/dklineii/status/1747612167426257061). It works. After holding four weeks of 1:1s using Dave's method, Employee X turns things around. Unexpectedly, your three other direct reports who adopted the 1:1 method from Dave began to improve as well. Alternatively, it _doesn't work_, and you realize Employee X isn't qualified. So you fire them. 5. **Create a Prevention Plan:** Whether Employee X turned it around or got fired, you need to ensure there isn't a "relapse" or recurrence. If they turned it around, how can you keep holding structured 1:1s (and teach the wider company to do the same!)? On the other hand, if you sacked Employee X, you need to analyze your hiring process for what you missed, update your hiring process, and train any hiring managers on the updates before you can honestly say, "Problem solved." Too often in my work as a coach, I notice problem-solving attempts stop at step two for "Issue A" because CEOs tend to skip (3-5) to work on relieving symptoms for "Issue B" once we resolve symptoms of "Issue A." For example, once a CEO fires Employee X, they move on to an issue with "Board Member A," only to have a performance issue surface with Employee Y that could have been prevented had they successfully identified, treated, and "defended" against the root cause with a good prevention plan. Diagnosing and treating the root cause is more demanding in the **_short term_**. It requires effort, while symptom relief initially feels easy but can have costlier **_long-term_** consequences. Establishing a habit of drinking enough water daily is harder in the **_short term_** than simply taking an Advil for each headache, but stomach bleeding from the pills will be **_harder in the long term_**. Similarly, writing down clear job expectations, training your team to run great 1:1s, and implementing a culture of accountability is much harder in the short term than writing a sternly worded Slack message. Still, the former will make for a more effective and resilient team than the latter. So, how do you begin to apply this in your life? Remember to start small. Problem-solving is a skill that needs to be trained. Don't start with the work or life equivalents of 100 lb dumbbells. Start with something that seems "easy." Maybe you wish your spouse would stop leaving all those cardboard boxes in the garage. _"What do they think? Some magic faerie comes and breaks the cardboard down every Wednesday?"_ Or maybe you keep getting questions about vacation, sick leave, or weather-related work-from-home days. Work through the steps, and don't stop at step two. Good luck! ## On My Mind Lately ### Reading - [The Terra Ignota Series](https://us.macmillan.com/series/terraignota) (Ada Palmer, 2016 - 2022). Humanity has done away with nation-states and the nuclear family. Any two places on Earth are no further than four hours travel away. Planetwide, workers have adopted a 20 hour work week. Happy workaholics are dubbed "vocateurs". War is a thing of the past. Or is it? One line that I've been unable to shake, from book three (aptly titled, [_The Will to Battle_](https://www.amazon.com/Will-Battle-Book-Terra-Ignota/dp/0765378043)): _"Hobbes tells us that war consists not in Battle only, but in that tract of time wherein the Will to Battle is so manifest that, scenting bloodlust in his fellows and himself, Man can no longer trust civilization's pledge to keep the peace. If so, we are at war."_ (p. 13) - [Psychoanalytic Diagnosis](https://www.amazon.com/Psychoanalytic-Diagnosis-Second-Understanding-Personality/dp/1609184947) (2nd Edition) (Nancy McWilliams, 2011). This is the latest of several books I've read on psychoanalysis. Nancy is a psychoanalyst, professor, and author. She's uniquely skilled at taking ideas usually relegated to the arcane language of academic psychology and writing for both a clinical and lay audience. That said, this book probably isn't for you if you're just generally curious about psychology or therapy. If you're a practicing therapist or coach, however, I think you'll find this book fascinating. ### Doing - **Wedding Planning**: It's remarkable how this manages to suck up 5+ hours every week. Special shout out to [Tailor's Keep](https://www.tailorskeep.com/) in San Francisco for helping me with my tuxedo. If you've ever wanted a bespoke suit, these guys rock. - **Learning Greek**: My fiancee's family is Greek and our wedding is in Greece. I've been using Duolingo for the first time, practicing for about 30-60 minutes a day, and this is so much better (and fun) than learning a language in college was! - **Conducting Weekly Reviews**: Khe Hy's [guide to conducting a weekly review](https://www.notion.so/look-blue-dot/How-to-conduct-a-weekly-review-using-Notion-025ec03ec9e84c88ae18e718c4ca3758?pvs=4) (a la David Allen's "Getting Things Done") is terrific. I've tried to do versions of this several times in my life, but I'm now on week six of doing this every Monday morning. Benefits include: avoiding less, focusing on priorities more, missing fewer commitments, processing email faster. --- ### Writing Beyond a Niche *Published: 2023-09-21* Season One of Hoo Boy was the Season of the Hedgehog. Season Two, I'm excited to announce, will be the Season of the Fox. "A fox knows many things, but a hedgehog knows one big thing," quothe ancient Greek poet Archilochus, apparently. Unfortunately, he didn't read _The Artist's Way_ by [Julia Cameron](https://en.wikipedia.org/wiki/Julia_Cameron), so we don't have piles of morning pages explaining the quote. But, in 1953, we got an essay on the idea from the philosopher Isaiah Berlin. In "The Fox and the Hedgehog," Berlin divided writers into two groups: the foxes, who study and write on a variety of themes and subjects, and the hedgehogs hammer on one idea over and over again. Over the last five years, I've noticed an explosion of hedgehogs writing online, and it's easy to see why. It seems like there's a new "The X Guy" every day ("The Writing Guy," "The Public Speaking Guy," and so on). The hedgehog's toolkit, picking a narrow audience and delivering for them, is a good one. It's easier for people to rally around your banner when you're the guys making a podcast about M&A than it is to start a general business podcast. We used this niching formula at Mattermark. We wrote _every day_ for four years on venture capital and startups in _The Mattermark Daily_. We featured up to five articles, each with a brief editorialized summary, by startup investors and another five by "operators" (people working at startups). At peak, over 100,000 people subscribed, and more than half of them opened our newsletter every day. Still, we ended up selling Mattermark in what TechCrunch called a "disappointing outcome," and I've had a chip on my shoulder ever since. Having written "The Daily," as we called it, for part of the newsletter's life, I felt like I _should_ have been able to replicate its success. I found myself repeatedly turning to ye olde niching formula to no avail. After Mattermark, I started Holloway, where we published books on business and technology. We settled on writing a newsletter, _Good Work_, "A hand-curated newsletter devoted to exploring how we choose to spend the 90,000 hours that will make up our careers." I replicated The Daily's format, featuring links to relevant content, but mixed it up by adding an introductory essay, which I'd try to limit to four paragraphs. It turns out brevity, like most things people prefer, is not easy. Or as mathematician, physicist, and philosopher Blaise Pascal put it: > _"I have only made this letter longer because I have not had the time to make it shorter."_ Good Work's audience grew to five or so thousand subscribers, but despite how much I loved writing the newsletter, I couldn't justify how long it took. After Holloway, I began coaching other founders and took two more swings at The Way of the Hedgehog with newsletters about coaching or issues that repeatedly came up with founders I worked with. I briefly collaborated on a newsletter with a much more experienced executive coach, [Jerry Colonna](https://www.reboot.io/team/jerry-colonna/), and eventually launched Season One of Hoo Boy. At first, Hoo Boy was easy. Anyone who has ever coached startup founders will be familiar with the deja vu of hilariously similar-but-different, situations popping up again and again. Not only did these situations provide me with endless material, they fed my curiosity as I'd learn more about each subject as I wrote. But the subjects founders brought up, and the ones I got curious about, while _adjacent to_ or _relevant to_, leadership and best practices for building a business, began to deviate enough that I didn't know how to coherently integrate them into Hoo Boy. In early August, I read _In Over Our Heads_ by [Bob Kegan](https://en.wikipedia.org/wiki/Robert_Kegan) and came across a passage that made things click for me: > _"These expectations [for adulthood] are chronicled, and even shaped, in the growing collection of cultural documents academics call (with no irony) 'literatures': 'the marriage literature,' 'the management literature,' 'the adult education literature,' and the like... for the most part, these literatures do not talk to each other, take no account of each other, have nothing to do with each other. The people who create the leadership literature do not read the parenting literature... there is no place to look to consider what is being asked of the adult as a whole."_ I remember where I was when I read this because I laughed at how much it fit my experience of the last three years (and didn't). At least half, if not closer to three-quarters, of the founders I coach will eventually show up to a session asking if they can use the hour to talk about "something 'not exactly work-related.'" Spoiler: it's about the person they're dating or married to. I emphasize that I'm not a couples therapist, but I'm happy to listen if they think it will help. It doesn't take a rocket scientist to connect the dots that the wisdom that can unblock us with relationships between co-workers might be applicable at home (and vice versa). But I now have a pile of books on couples therapy I've worked my way through, equally out of my curiosity and to be better prepared for the next "not-exactly-work-related" topic in a coaching session. This fascination with marriage and intimacy and "literature" is a perfect example of a subject _adjacent to_ or _relevant to_ leadership but distinct enough that I struggled with how I could write about it publicly. I'm _not_ a couples therapist, and a part of me is afraid that those Big Bad Couples Therapists with their Big Bad Degrees will come after me for being the academic version of a street rat. The fear of being declared a charlatan by psychologists I don't know, have never met, and whose names I don't even know, combined with the chip on my shoulder from Mattermark and the patience to sit with both to understand them, led me to stop writing Hoo Boy in February. I couldn't focus on business tactics and mental models in my writing when my curiosity was pulling me elsewhere. Since then, I've been wrestling with how to coherently give readers an idea of what to expect from my writing without zipping up a poorly sewn hedgehog costume. I thought, "Who else does what I want to do?" and "Whose writing do I _really admire?_" One writer came to mind above all others: [Maria Popova](https://twitter.com/brainpicker) at _[The Marginalian](https://www.themarginalian.org/)_ (formerly _BrainPickings_). Maria's about page reads: > _"a one-woman labor of love, exploring what it means to live a tender, thoughtful life of purpose and gladness, wonder-smitten by reality, governed by the understanding that creativity is a combinatorial force: ideas, insights, knowledge, and inspiration acquired in the course of being alive and awake to the world, composited into things of beauty and substance we call our own."_ Maria has succeeded as a fox in a hedgehog's world, writing about basically whatever she finds interesting, and it turns out lots of other people find that stuff interesting, since she started writing online in 2006, her efforts have been completely run by donations. I want to do something _way more_ like Maria has done than become yet another "The X Guy." And while Maria is no hedgehog, the subjects she explores make sense together: > _"science, art, philosophy, and the various other tendrils of human thought and feeling, a private inquiry shimmering with the ultimate question, the great quickening of wonderment that binds us all:_ **_what is all this?_**" Like Maria's writing, I expect mine going forward will, in a fuzzy sense, "make sense" together. But I can't connect the dots looking forward. I can't tell you exactly what to expect, like the hedgehog can. What I _can_ do is share a few of the questions, other than, "How can I use everything I learn to be a better coach to my clients," I'm interested in exploring and finding ways to talk about in plain language: - **What might I learn by following my curiosity _my way_?** In college, I studied history and a little bit of business, but my first job was designing software. I've long learned what I need to learn outside of formal education, and I'm curious what I can learn about psychology by following my curiosity without a master's or PhD program serving it up for me. - **What are alternate ways of working?** I've been joking with friends for a few years now that I've "found a business model for a life as an academic." I study and read for hours in the morning and then work with clients in the afternoons. It's not for everyone by any means, but I'm interested in finding and learning about people who've figured out non-traditional ways of working. - **Can people be great _and_ happy?** Chef, scientist, athlete, public servant, industrialist, or musician, many of us seek _greatness_. I know I do. Is great vs. happy an _aeterna disputatio_, or is it a failure of ambition that we settle for one or the other? - **What might an almanac of "living well" look like?** Even before adulthood, society asks us to make consequential decisions with vanishingly little guidance. For example, juniors in high school aren't allowed to use the bathroom without permission, but at the same time we ask them to commit to hundreds of thousands of dollars in debt for college. What might an almanac or sorts with guidance on many of life's big choices (education, career, romance) and recurring themes (starting over, quitting, failure, loss, celebration, and so on) look like? Where Season One felt like a carefully prepared lecture to an audience with meticulous attention to detail and design, I'm hoping Season Two will feel more like popping into a friend's garage with a beer or two and saying, "Hey!" I hope you'll enjoy it, and if you do, I hope to hear from you. ## On My Mind Lately ### Reading - [The Person and the Situation](https://www.amazon.com/Person-Situation-Perspectives-Social-Psychology/dp/1905177445) (Lee Ross, Richard Nisbett, 1991) - [Helping](https://www.amazon.com/Helping-Offer-Give-Receive-Help/dp/1605098566) (Edgar Schein, 2009) - [Marooned in Realtime](https://www.amazon.com/Marooned-Realtime-Peace-Vernor-Vinge/dp/0765308843) (Verner Vinge, 1986) - [Light Bringer](https://www.amazon.com/Light-Bringer-Red-Rising-Novel/dp/0425285979) (Red Rising #6, Pierce Brown, 2023) ### Doing - Clearing out our guest bedroom and turning it into a home gym. - Wedding planning. - Heading to Boston for a week to learn more about how people change from Lisa Lahey and Bob Kegan. - Playing way too much [Baldur's Gate 3](https://baldursgate3.game/) ### Anticipating - I still haven't seen _Oppenheimer._ _Thanks to [Rachel Jepsen](https://open.substack.com/users/15170507-rachel-jepsen?utm_source=mentions) and [Nathan Baschez](https://open.substack.com/users/5636840-nathan-baschez?utm_source=mentions) for reading and editing drafts of this post._ --- ### Running Great One-on-Ones *Published: 2023-03-26* # Running Great One-on-Ones Many coaching conversations begin with clients identifying perceived performance issues with employees. However, the real problem frequently stems from absent or ineffective one-on-one meetings. "1:1 meetings, when done well, are to a great working relationship as diet and exercise are to long-term health." This article provides comprehensive guidance for conducting effective one-on-ones, including a detailed FAQ and slide deck for team training. ### A Question > "Is everyone on my team focused and productive? If not, is there something I could be doing differently?" Erika Andersen, [*Learning to Learn*](https://hbr.org/2016/03/learning-to-learn) ### A Quote > "Those who make the most of meetings frequently spend substantially more time preparing for the meeting than in the meeting itself." Jim Collins, [*The Effective Executive*](https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials-ebook/dp/B01F1WZGNC) ## Teach Your Team to Run Great 1:1s The presentation is available [on SlideShare](https://www.slideshare.net/AndySparks13/how-to-run-11s-that-will-blow-your-managers-mind-v10-256819083). Most people either skip one-on-ones entirely or conduct them inefficiently. Well-executed one-on-ones offer substantial value: they allow employees to manage upward, receive feedback, learn, and remove obstacles. Sparks has trained countless founders on this skill and created resources to help them teach their teams. ### What is a 1:1? - A recurring meeting between subordinate and manager - Typically weekly, though monthly intervals are possible ### Goals of a 1:1 - Establish dedicated, regular communication space - Managers collect and share information - Subordinates collect and share information - Reduce reactive work; promote proactive engagement ### Why 1:1s Matter - Information flows freely within effective organizations - Subordinates must "manage up" actively; one-on-ones provide the ideal venue - High leverage for managers: 60-90 minutes of time can enhance performance for weeks - Scheduled meetings reduce interruptions via Slack and other channels ### Frequency - Begin with weekly meetings - Andy Grove recommends assessing "task-relevant maturity" (TRM): experience with specific work and prior performance - If time is constrained, maintain the schedule but reduce scope (e.g., 30 minutes instead of 60) ### Duration - Minimum 60 minutes recommended - Grove suggests "enough time to broach and get into thorny issues" - Shorter meetings (15-45 minutes) prove insufficient; substantive discussion typically begins after 30 minutes - Longer, less frequent one-on-ones beat frequent, brief ones ### Agenda Ownership Subordinates should own the meeting agenda. Rationale: a manager with eight direct reports faces 12 hours of one-on-one time plus preparation. A subordinate invests only 1.5 hours, making them the logical agenda owner. ### Preparation Subordinates should maintain a "running agenda document" (spreadsheet, Google Doc, Notion, etc.) shared with their manager. Between meetings, both parties add discussion items. This prevents forgetting important topics and eliminates interrupting managers with non-urgent matters. ### Meeting Content ![1-on-1 meetings template](/images/essays/1-on-1s.png) **Brief Status Report** - Present progress on goals, KPIs, and action items in consistent format - Limit to 5-10 minutes - Ask managers what information they want reported **Issues** - Discuss potential problems and obstacles - Highlight any KPIs or goals at risk - Include project difficulties and interpersonal challenges **Beware Gossip** - Gossip involves "any statement about another made by negative intent" or "any statement the speaker wouldn't share if that person were present" - Both speaker and listener enable gossip - "Many people choose to listen to gossip to avoid discomfort of establishing a boundary" (*The 15 Commitments of Conscious Leadership*) **Questions** - Ask how work aligns with company objectives - Inquire about advancement requirements - Clarify performance evaluation criteria **Performance Feedback** - Solicit feedback on your performance - Ask managers to rate you on a 1-5 scale (1=poor, 3=meets expectations, 5=exceptional) - Request specific improvement areas - Advanced approach: create a performance rubric for monthly discussions **Mutual Feedback** - Both parties should exchange feedback weekly - Each person identifies one behavior to continue and one to improve - Builds feedback muscle and maintains information flow ### Manager's Role - Listen, learn, and collect information - Coach subordinates through raised issues - Train direct reports on effective one-on-ones - Grove summarized it: "Facilitate subordinate's expression of what's going on and what's bothering him" - Monitor performance against goals - Clearly communicate desired status report information ## Reads & Resources ### Articles **[The Difficulty of Empathizing Up](https://www.edbatista.com/2017/03/the-difficulty-of-empathizing-up.html)** Ed Batista explores "managing up" through an empathy lens. He notes that "the expression of empathy involves not only comprehending another person's perspective and emotions, but also suspending our own judgments." Whether managing up or down, cultivating "a more empathetic response in general" benefits all parties. ### From Twitter **[Freeman Dyson on Tool-Driven Scientific Revolutions](https://twitter.com/stevesi/status/1557848673366601728)** In 1993, Dyson observed: "Scientific revolutions are more often driven by new tools than concepts." We're entering a tool-driven revolution in artificial intelligence. Bill Gates [declared](https://www.wsj.com/articles/bill-gates-says-artificial-intelligence-is-the-most-revolutionary-technology-in-decades-75fb8562) AI "the most revolutionary technology in decades," comparing it to "the microprocessor, the personal computer, the Internet, and the mobile phone." ### Audio **[The Complete History & Strategy of Nintendo](https://www.acquired.fm/episodes/nintendo)** Nintendo was founded in 1889, 92 years before Donkey Kong, making handmade playing cards. In a 3.5-hour episode, hosts Ben and David cover Nintendo's complete history. Perfect for those who grew up with Nintendo, appreciate transformative business stories, or enjoy compelling narratives. ### Books ![Scaling People](/images/essays/scaling-people.png) **[Scaling People](https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212)** Claire Hughes Johnson, former Stripe COO and current board member at HubSpot and The Atlantic, wrote this 400+ page guide on "tactics for management and company building." The book blends practical advice with helpful stories. A standout feature: Stripe used QR code footnotes, a clever touch from the former publisher. ### Dice Roll **[The Fair Play Deck](https://www.amazon.com/Fair-Play-Deck-Conversation-Prioritizing/dp/059323166X)** This card deck accompanies *Fair Play*, a book helping couples divide household tasks. The concept sparked an idea: a similar deck for co-founders and management teams, with cards representing major ownership areas (engineering, sales, marketing, design, finance, etc.). Each card designates a single owner. A valuable concept awaiting a creator. ## Further Reading 1. Grove, Andy. [*High Output Management*](https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884) 2. Scott, Kim. [*Radical Candor*](https://www.radicalcandor.com/) 3. Mochary, Matt. [*The Great CEO Within*](https://www.amazon.com/Great-CEO-Within-Tactical-Building-ebook/dp/B07ZLGQZYC) 4. Meyer, Faith. [Job Responsibilities Rubric](https://docs.google.com/document/d/1dMxcNgm3pQe_dR9_UjwucbxtSG1k7Wj8RFdQag5FQ-U/edit) 5. Kline, Dave. [Expectations Template](https://docs.google.com/spreadsheets/d/16JX80AJ79_efuXEOFgnCva5BVZodawEgaZUkq_r2Jc8/copy) 6. Batista, Ed. [Group Dynamics: A Leader's Toolkit](https://www.edbatista.com/2022/09/group-dynamics-the-leaders-toolkit.html) 7. Dethmer, Jim; Chapman, Diana; Klemp, Kaley. [*The 15 Commitments of Conscious Leadership*](https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE) 8. Evanish, Jason. [150+ One on One Meeting Questions Great Managers Ask](https://getlighthouse.com/blog/one-on-one-meeting-questions-great-managers-ask/) --- ### Why We're Unprepared for Co-Founder Relationships *Published: 2023-03-12* # Why We're Unprepared for Co-Founder Relationships When I first sat down to write this piece, I wrote it in the voice of McSweeny's. Humor speaks delightful truths, and while I laughed at my writing, I couldn't help but feel like it would leave readers with shame. It was funny, but it was, frankly, kind of mean. I rewrote it. So what can you expect in this week's issue? We're talkin' about co-founder conflict. I noticed a lot of people I know (and my circle is weirdly indexed on being a startup founder) are, admirably, intent on being a great partner to their girlfriend/boyfriend/wife/husband/partner, but they're also struggling learn what they want from and how to be a great partner to...their other partner, their business partner/co-founder. So this week's issue is about WHY we struggle with our business partners. And let me tell you, while this issue is long, it's dense with insights that I hope become the subject of some good conversations over the next couple of weeks. And in my next issue, I'll write about HOW we can be better partners to our business partners (and encourage them to do the same). ### A Question > "What's your own responsibility for what's been happening? Put another way: what did you do to help create this situation?" ### A Quote > _"A spirit of candor and frankness, when wholly unaccompanied with coarseness, he admired in others, but he could not acquire it himself."_ Anne Bronte, [*The Tenant of Wildfell Hall*](https://www.amazon.com/Tenant-Wildfell-Hall-Penguin-Classics/dp/0140434747/) p. 22 ## A Tale of Two Partners: Life Partnership vs. Business Partnership Being better at being married, compared to our parents, is one of the most universal ambitions I run across in millennials. We believe we have the tools, therapy, endless books, a culture beginning to value emotional intelligence, to be better partners to our partners and parents for our kids. I certainly have a privileged reference frame where my circle went to college (even if it was at a state school in the midwest) and are business owners or well-paid knowledge workers. Still, I take pride in what feels like a generational commitment to level up. Marriage is a relationship, and for most, it is _the_ relationship, but for founders and business owners, there's another relationship that ranks right up there: the co-founder or business partner. And so, it's striking how much I see people who are committed to being great at one kind of relationship, their marriage or partnership, struggle to keep their head above water in another, their business partnership. ## Why We Struggle with Our Co-Founders So what gives? What makes business partnerships so much more likely to overwhelm us when compared to life partnerships? Let me give you a metaphor. Imagine you gained 200 pounds in six months. Your life has now changed dramatically. You went from fit and healthy to having your doctor, friends, and family remind you of how high the stakes are to be overweight in what feels like a single night. Starting a business is a bit like that for at least four reasons: start conditions differ, it's easier to blame someone else for their part than take responsibility for our part, we want to protect ourselves and our partners, and finally, it's easier to say we're serious about being a good partner than to actually do the work to be one. A quick sidebar, though, first. I love a good statistical misattribution or mistranslation like in the elementary game telephone. People love to cite Noam Wasserman with a statistic on how most companies fail due to co-founder conflict. I even almost cited it here before I decided to check the facts. Take this one from [Entrepreneur.com](http://entrepreneur.com/), for example, "In his book, The Founder Dilemma, best-selling author and Harvard Business School professor Noam Wasserman claims that 65% of high-potential startups fail due to conflict among co-founders." First of all, the book is called The Founder's Dilemmas (plural). And in it, Noam cites a 1989 study of 96 portfolio companies across 49 venture capital firms in which he surveyed V.C.s "cited problems within the management team as a top-three contributing factor, making it the most important contributing factor for 61 of those companies." Nowhere does he mention the word, Co-Founder. That said, most of what you'll read here applies to "executives on the executive team" as much as it does "co-founders" or "business partners." ### Start Conditions Marriage and a business partnership are both binding legal commitments that tie two people's futures together, and the paths that two people take that lead to these two different commitments differ in at least four distinct ways: 1. The "dating" period is much shorter for business partners vs. life partners. 2. The stakes increase much faster for business partners vs. life partners. 3. A business partnership necessitates close collaboration on complicated and complex challenges much sooner than a life partnership. 4. There is far less cultural preparation for a business partnership's difficulties than for a marriage. ### Dating Period - **People take their time getting married.** In 2021, The Knot surveyed 5,000 people who got engaged that year and found that most couples dated for more than two years before getting engaged, and a separate study found the average length of an engagement is fifteen months. - **People do not take their time getting into business together.** I couldn't find data on the average length of time co-founders spent preparing to start a company together. Still, based on my experience with my own business and the 40+ companies I've worked with as a coach, I would be shocked if it averaged over three to six months. The closest comparable I could find was from Noam Wasserman, his book, The Founder's Dilemmas, summarized his findings from data on 10,000 founders, who found that "40% of founding teams included at least one set of co-founders who had a prior social relationship without having shared a prior professional relationship," indicating that some teams at least knew each other before getting into business together. Interestingly, he found these preexisting relationships did not increase the odds of success but rather increased the likelihood of a co-founder's departure by 28.6%. ### Financial Stakes - **When we're dating somebody, we gradually step into shared financial risks.** Only when we marry someone, which happens after years, do we enter into a binding legal contract that ties our financial futures together. Signing a lease, moving in together, is another way we do this, and most people don't move in together for a while. - **In a business, the financial stakes get high quickly.** Your financial futures are bound when you incorporate and split equity. This often involves individual goals like paying off debt, saving for an engagement ring and wedding, a house, college, and retirement. And when those goals depend on how someone else behaves in a business relationship, any slip-up or mistake from one party can feel like a threat to others. ### Collaborative Requirements - **In year one of dating, the collaborative requirements are simple.** The most complex thing most people are likely to need to collaborate on is either travel plans, cooking a meal, or throwing a party together. And if any of those things goes poorly, most people will end the relationship and look for a better-suited partner. - **People need to collaborate on many complicated and complex business problems in year one.** In the first year of business, two people need to research a market together, build a product, determine a business model, incorporate a company and split equity (tying their financial futures together in a binding legal agreement), hire and fire people, raise money from investors, and more. If any of these things go poorly, you need to involve a lawyer to split up. ### Cultural Preparation - **We treat marriage like the default path.** 53% of American adults are married. Even if our parents aren't together on day one, we're immediately exposed to marriage. Our friends' parents' are married. Our parents thought about it and decided not to get married, marry, or they got divorced. We're steeped in the idea that one day, we'll look for a life partner from very early on. Our parents, friends, and extended family are like Pez dispensers but for marriage advice. And not to mention the deluge of dating shows, rom-coms, marriage plots, and subplots you can only avoid by never turning a screen on. Then, when or if we do get engaged, many cultures and religions have pre-marital counseling traditions to further prepare us for the inevitable challenges two people will face when building a life, and for many, a family, together. - **We don't treat starting a business like the default path.** There are 31M small businesses in the U.S. (accounting for 99% of companies), only six million of which have employees. Fascinatingly, 55% of American adults will start a business in their life, but most will not make it past their sixth year. For most of us, the default path is "get a job," not "start your own business." We're not steeped in "how to start a business" and "how to choose a great business partner (and be a great partner to them)" in the same way we are our life partners. And while resources like First Round Review's "[Founder Dating Playbook](https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder)" are a significant step in the preparation department, they're new and, in my opinion, insufficient, ineffective, and give people a false sense of security. ## Taking Responsibility Both people are responsible in every conflict, struggle, challenge, or whatever you want to call it. There's a part of the struggle and resolution you need to take responsibility for, and there is a part the other party needs to take responsibility for. The thing is, it's way easier to see someone else shirking their responsibility and get righteous than it is to look at our half of the equation. The wonderful team at Conscious Leadership Group makes "taking radical responsibility" the foundation of their methodology, encouraging every individual to commit to "taking full responsibility for the circumstances of their life and for their physical, emotional, mental, and spiritual well-being" instead of "blaming others and myself for what is wrong in the world." Peter Drucker shared an excellent example of what taking responsibility for something instead of blaming looks like in this 1967 book, _The Effective Executive_, by citing an even older example from 1938: > "We all know, thanks to Chester Bernard's 1938 classic, _The Functions of the Executive_, that organizations are held together by information rather than ownership or command. Still, far too many executives behave as if information and its flow were the job of the information specialist, for example, the accountant. As a result, they get an enormous amount of information they do not need. The best way around this problem is for each executive to identify the information he needs, ask for it, and keep pushing until he gets it." > > The Effective Executive p. xxiv For good measure, let me illustrate with a modern example of a pattern I see over and over again. The COO doesn't want to give the CEO feedback because they're afraid the CEO will react with an unpleasant emotion like anger, put another way, "The CEO doesn't take feedback well." This is an expert way to shirk responsibility, so let's break this down. In this example: - It is the CEO's responsibility to take feedback well. Otherwise, they will cut themselves off from the flow of information. - It's the COO's responsibility to deliver feedback to their CEO, so the CEO has the information they need to make good decisions. - It's the COO's responsibility to consider whether the feedback they want to deliver is 1) in service of resolving a conflict or improving a situation or 2) because it would feel good to release their anger or frustration. 1 is a good reason, and 2 is not. - It is the COO's responsibility to support the CEO or quit. - It's the COO's responsibility to determine whether the CEO's inability to handle feedback well is something they can tolerate or not and, if it is not something they can tolerate, to quit. For what it's worth, the COO in question was me. I was the COO who didn't give feedback because I didn't think my co-founder took feedback well. It was easy to blame someone else instead of taking responsibility for figuring out how to either a) deliver the feedback in a way it was easier to digest, b) accept that my C.E.O. wasn't going to change, or c) quit. And by not doing any of those three, I undermined her. It's a great example because so many of us see so clearly what the other person could be doing better in the partnership. Still, we miss the things we take responsibility for, the things we can control, and miss what could otherwise be beautiful opportunities to 1) grow ourselves, 2) help our partners grow, and 3) build more effective and successful organizations. ## Fear, Defensiveness, and Protection Defensiveness gets a bad rap. People defend or protect things they care about. So if someone's being defensive, it's because they give a shit, which can often feel in remarkably short supply. That said, hold your ground too firmly, that is to say, _inflexibly_, your business will never move forward. There are many things people can get defensive about, all of which are because they're afraid something bad will happen and always because they're scared of something bad happening to either 1) themselves, 2) others or 3) both. Let's break that down. We protect ourselves because we want to avoid discomfort and pain. Makes sense. And a lot of what we're protecting ourselves from is other people. We don't want to get yelled at, we don't want to take any emotional abuse, and we don't want to learn hard truths that threaten our identities or egos. But we have to take the long view. When I think about figuring out how to have a conversation with a co-founder about how they don't take feedback well, that conversation feels painful. I'd love to not have it. But if I take the long view, I know that if our C.E.O. doesn't get better at taking feedback, the company probably won't succeed because people will stop giving them the information we need. Which pain is greater? An uncomfortable conversation, or taking an L on four years of hard work? We protect others because we don't want others to experience discomfort or pain. Also makes sense. Our co-founder said they'd do something and then they didn't. Now I'm avoiding the pain of an uncomfortable conversation, but also, since I care about my co-founder, I don't want to hurt them. But I know I'm No Good at giving critical feedback (I always end up yelling at people!) So I protect them, freeze up, and zero feedback doth I give. But again, we have to take the long view. You may be protecting yourself and your partner from some short-term discomfort, but the long-term damage of a hundred unresolved conflicts ne'er spoken of might poison you slower than Cersei Lannister, but poison you, all the same, it will. ## Serious People Chris Power is the founder and C.E.O. of [Hadrian](https://www.hadrian.co/), a very rad American manufacturing company working on rescuing our aerospace industry from a looming manufacturing crisis. In [episode 281 of Invest Like the Best](https://podcasts.apple.com/us/podcast/invest-like-the-best-with-patrick-oshaughnessy/id1154105909?i=1000566345132), Chris talks about serious people vs. unserious people, and I want you to consider whether you're serious. Huh? Imagine we are all running a town together. Each of us has a role, and a serious person has to perform their function or else society degrades. An unserious person passes responsibility. Many co-founders are not serious about being great partners to their business partners/co-founders, similar to how many people are not serious about their health. We know that getting enough sleep, eating a healthy diet, and getting 7+ hours of exercise each week are baseline requirements of physical health, and while most of us want to be healthy, we aren't serious about putting in the work. So when it comes to our co-founders, if we want to be great partners (and great partners build great companies together), we need to be serious about putting in the work, and while putting in the work won't be easy, we do understand quite a bit about what that involves. So stay tuned for issue 17, where I'll dive into that. Hoo boy, indeed. ## Reads & Resources ### Articles **[Startup Decoupling & Reckoning](https://blog.eladgil.com/p/startup-decoupling-and-reckoning)** If you plan on fundraising in the next 12 months, you need to read this piece by [Elad Gil](https://twitter.com/eladgil). The piece is a good overview of "how we got to now" regarding the recent public market tech stock price collapses and the current private market fundraising environment. Elad also argues that "No matter, the valuation reset coming for private tech is so stark (50X to 100X ARR in 2021 to 10X) that a recession or drop in spend will only matter on the margin." Given this bleak picture, he offers practical advice that, while it may feel like an icy splash of water, founders are likely getting used to that. ### From [Twitter](https://x.com/andysparks) **[Dr. Emily Anhalt on Relationships](https://twitter.com/dremilyanhalt/status/1595085337864597505?s=20)** I've followed Dr. Emily Anhalt on Twitter for quite some time. She is a clinical psychologist, TED speaker, Co-Founder, and Chief Clinical Officer at Coa, "your gym for mental health." So she kind of knows her shit. So I will let her tweet speak for itself: _"Psst... any relationship that can be ruined by a thoughtful conversation about how you feel and what you need doesn't have long-term stability or potential anyway."_ ### Audio **[Tim Ferriss #607: Duolingo CEO, Luis von Ahn](https://tim.blog/2022/07/12/luis-von-ahn/)** Tech CEOs aren't exactly enjoying a moment of public popularity, what with Elon Unchained being the tech sideshow of early 2023 and all. So, listening to Luis von Ahn, Co-Founder, and CEO of Duolingo, speak with Tim was a breath of fresh air. Luis was surprisingly down-to-earth for the CEO of a public technology company, and the story of Duolingo is wholesome in so many ways. Tim and Luis talk for the second time in this episode (in their [first recording](https://tim.blog/2016/01/26/luis-von-ahn/), Duolingo was 60 people; it's now 600), so the contrast between the two episodes is a rare view into the mind of an early CEO and a public company CEO. ### Books ![Consolations by David Whyte](/images/essays/consolations.png) **[Consolations](https://www.amazon.com/Consolations-Nourishment-Underlying-Meaning-Everyday/dp/1786897636/ref=pd_lpo_2?pd_rd_w=4Yqvu&content-id=amzn1.sym.116f529c-aa4d-4763-b2b6-4d614ec7dc00&pf_rd_p=116f529c-aa4d-4763-b2b6-4d614ec7dc00&pf_rd_r=1DX9X87DQ8D33H24DVBG&pd_rd_wg=eoEYs&pd_rd_r=fc761995-121f-450d-8059-56629769b696&pd_rd_i=1786897636&psc=1)** Every time I quote David Whyte, I cringe a bit. I joke with clients that the moment you first discover David Whyte, it's only a matter of time before you become a coach. David is a former marine biologist turned full-time poet. Much of his poetry is about our relationship with our work and what it takes to be creative, so entrepreneurs find his work resonates more than a fair bit. His book, Consolations, is a book of poetry that I think most people who've never read a book of poetry would love. Each poem is a poem on one word. My favorite? _Close_. Here's an excerpt: "_Human beings do not find their essence through fulfillment or eventual arrival but by staying close to the way they like to travel..._" ### Dice Roll **[S.P.A.D.E.](https://coda.io/@gokulrajaram/gokuls-spade-toolkit)** One of the common patterns I see causing **_drama_** at startups is when one person proposes the team makes a hard decision in a casual manner, usually giving the team little context, time to prepare and think about the hard decision, and an expectation that the team makes the decision in the meeting or quickly over Slack. People freeze up, lash out, or react otherwise emotionally, and the team is sent into a tizzy. Gokul Rajaram developed a framework to solve this problem, and I love it. It's called S.P.A.D.E.: Setting, People, Alternatives, Decide, Explain. You don't use it for every decision, only hard ones. But if you train your team to follow this framework when proposing a solution to a gnarly problem, I guarantee the level of irritation and drama around decisions will decrease. ## Footnotes 1. [The Founder's Dilemmas](https://www.amazon.com/Founders-Dilemmas-Anticipating-Foundation-Entrepreneurship/dp/0691158304), p. 100; 424 (Noam Wasserman, 2012) 2. [The Knot 2021 Jewelry & Engagement Study](https://www.theknotww.com/press-releases/2021jewelryandengagementstudy/) 3. [The Knot Real Weddings Study](https://www.wedinsights.com/report/the-knot-real-weddings) 4. [Rising Share of U.S. Adults Are Living Without a Spouse or Partner](https://www.pewresearch.org/social-trends/2021/10/05/rising-share-of-u-s-adults-are-living-without-a-spouse-or-partner/) (Pew Research, 2021) 5. [Small Business Administration FAQ 2020](https://cdn.advocacy.sba.gov/wp-content/uploads/2020/11/05122043/Small-Business-FAQ-2020.pdf) 6. [Millions Are Entrepreneurs in the United States](https://entrepreneurship.babson.edu/millions-are-entrepreneurs-in-the-united-states/?_ga=2.142318130.1055354827.1678220260-1606080639.1678220260) (Michael Chmura, 2019) 7. [Entrepreneurship and the U.S. Economy](https://www.bls.gov/bdm/entrepreneurship/bdm_chart3.htm) (BLS, 2016) 8. [The 15 Commitments of Conscious Leadership](https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE) (Jim Dethmer, Diana Chapman, Kaley Klemp, 2015) --- ### Conducting a Time Audit *Published: 2023-02-26* # Conducting a Time Audit ### A Question > "What can you learn about managing yourself from how the most effective people you know manage themselves?" ### A Quote > "Executives who do not manage themselves for effectiveness cannot possibly expect to manage their associates and subordinates." Peter Drucker, *The Effective Executive* ## Conducting a Time Audit Dee Hock's philosophy holds that great managers should allocate their time as follows: 50% managing themselves, 25% managing up, 20% managing across, and only 5% managing down. Most actual managers reverse these proportions, spending excessive time on downward management. To manage yourself effectively, begin by examining how you spend your time. ### The Three-Step Framework: Get It; Know It; Use It ![Time audit output](/images/essays/time-audit-output.png) **Get It**: Track and classify how you're spending your time over 3-4 weeks (ideally twice yearly). **Know It**: Review your data to determine whether your time allocation aligns with your priorities. **Use It**: Make decisions about eliminating, delegating, reassigning, or modifying activities. ### Tracking and Classifying Your Time ![Notion screenshot for time tracking](/images/essays/notion-screenshot.png) Record your activities with specificity rather than broad categories. Instead of logging "marketing," note "reviewed product marketing messaging draft." Use spreadsheets, Slack channels, or calendar reviews to document your work. Key recommendations: - Record activities immediately after completing them - Ensure your calendar reflects reality - Set weekly goals for time allocation at the week's start - Ask direct reports: "What do I do that wastes your time?" ### Four Decision Questions for Each Activity 1. **"What would happen if this were not done at all?"** If nothing, **stop** this activity. 2. **"Could this be done by somebody else just as well, if not better?"** If yes, **delegate**. 3. **"Does this activity need more work from someone else before it's ready for my review?"** If yes, **reassign**. 4. **"Could this activity be modified to be shorter or better use my time?"** If yes, **modify**. Activities passing these filters should be **kept** if they feel essential. ![Time audit breakdown](/images/essays/time-audit-breakdown.png) ### The Compounding Effect A CEO using her time even 10% more effectively can cascade that efficiency throughout the organization. The real power emerges when leaders model this practice and encourage their teams to conduct their own time audits. ## Reads & Resources ### Articles **[How to Use Gmail More Effectively](https://klinger.io/posts/how-to-use-gmail-more-efficiently)** Andreas Klinger applies David Allen's "Getting Things Done" methodology to email management, offering practical systems for processing inbox overload. ### From [Twitter](https://x.com/andysparks) **The Best of Lenny's Newsletter in 2022** [Lenny Rachitsky](https://twitter.com/lennysan) explores product management fundamentals and how great product teams create market-fit solutions. ### Audio **[Solving the Cold Start Problem](https://podcasts.apple.com/us/podcast/solving-the-cold-start-problem-w-andrew-chen/id1187402810?i=1000543715525)** [Andrew Chen](https://twitter.com/andrewchen), a16z partner and former Uber growth leader, discusses why startups sometimes fail to gain traction despite effort. ### Books ![The Effective Executive](/images/essays/effective-executive.png) **[The Effective Executive](https://www.amazon.com/Effective-Executive-Definitive-Getting-Things/dp/0062574345/)** Peter Drucker's essential text addresses self-management as foundational to leadership effectiveness, often overlooked by emerging leaders. ### Dice Roll **[The Cognitive Distortions of Founders](https://www.harrisonmetal.com/library/the-cognitive-distortions-of-founders)** [Michael Dearing](https://twitter.com/mcgd) at Harrison Metal identifies five common founder thinking patterns, each containing both superpowers and potential pitfalls. ## Three Key Takeaways 1. A focused CEO managing her time well is fundamentally a good CEO. 2. A CEO modeling time audits and encouraging organizational adoption builds a more focused company. 3. A CEO completing a time audit AND soliciting team feedback becomes both effective and appreciated. --- ### Avoiding the Startup Graveyard *Published: 2023-02-05* # Avoiding the Startup Graveyard The fundamental difference between small and large companies: small companies focus on creating customer value (which accidentally creates shareholder value), while large companies focus on shareholder value (which accidentally destroys customer value). ### A Question > What is the price threshold at which your company could no longer afford to field a sales team? ### A Quote > "The single most important decision in evaluating a business is pricing power." Warren Buffett ## Big Idea #14: The Startup Graveyard Source: SaaS Startup Strategy, Three SaaS Sales Models (2010), Joel York Two problematic ingredients, low pricing combined with high-touch sales processes, create conditions that can seduce and ultimately destroy founders and their companies. ## Theory ### Why It Matters Every company on the path to $1B in revenue must determine its customer acquisition strategy. The core question: Will the business model involve selling high-priced products to a small customer base or affordable products to many customers? ![Startup graveyard diagram](/images/essays/startup-graveyard.png) This decision determines which of three sales models to implement: **1. Enterprise Sales** - High-touch, multi-meeting sales cycles spanning months or years - Expensive to execute, requiring premium pricing to justify sales costs **2. Transactional Sales** - Sales completed in 30 minutes to two meetings - Straightforward, scriptable processes with minimal training - Viable if sales yield exceeds 2 ([fully loaded cost per rep](https://www.marketsource.com/blog/real-cost-b2b-salesperson/) divided by revenue generated) **3. Self-Service** - Required when price point becomes too low to support a sales team - For example: a $1,000/year product would require a sales rep to close 150 deals monthly (assuming $150K fully-loaded cost) to achieve a sales yield of 2 - Success depends on clear website messaging and minimal human interaction ### The Graveyard Trap Companies often end up in the graveyard because founders conflate discovery with sales: - During discovery, founders talk with potential customers about problems, gather feedback, and learn about willingness to pay - This process resembles sales but has different objectives - When founders discover they *can* sell at a low price point, they often ignore whether revenue covers costs, especially with venture capital funding - Revenue grows initially, then plateaus when the company seeks additional funding - Too late, founders realize their customer acquisition cost is unsustainable, they cannot raise capital, and lack resources to pivot toward self-service ## Practice The author shares Mattermark's experience as a cautionary tale: Early subscriptions sold for $500/month or $4,799/year, with a fully-loaded sales cost of $200-300K per rep. Breaking even required closing 3.5-5.2 deals monthly; achieving traction required double that volume. The CEO and author closed $1M+ in the first year, signaling readiness to scale the sales team. However, once hired salespeople were added, reps rarely closed more than five deals monthly. The problem: Early-adopter sales had low complexity, but crossing the chasm increased deal complexity, causing sales yield to decline. Instead of recognizing this as a warning signal, the company blamed poor sales performance. Recovery options, simplifying the sale, building self-service, raising prices, or adding features, came too late. ## Recommendation Avoid the graveyard by: - Printing the 2x2 pricing/sales model matrix - Posting it prominently in project management systems - Reviewing it daily - Committing to which viable quadrant the business will occupy ## Reads & Resources ### Articles **Leslie's Compass: A Framework For Go-To-Market Strategy** Mark Leslie's complementary framework examining the relationship between sales intensity and marketing intensity, with practical questions for evaluating product-market fit and go-to-market strategy. ### From [Twitter](https://x.com/andysparks) **It's a CEO or Co-Founder Job to Find PMF** Gokul Rajaram observed that Series B and C companies sometimes hire Chief Product Officers hoping they'll discover product-market fit, a misalignment of responsibility. A notable comment: "Any CPO capable of finding PMF for a series C company is better off starting their own company." ### Audio **[Acquired S12E1: The NFL](https://www.acquired.fm/episodes/the-nfl)** This episode explores pricing and value capture through the NFL's history. The hosts conclude the NFL may be among the few organizations that captures all, or exceeds, the value it creates. ### Books ![Don't Call It That](/images/essays/dont-call-it-that.png) **Don't Call it That** Eli Altman's workbook guides naming processes for new ventures and products. Altman's firm, [A Hundred Monkeys](https://www.ahundredmonkeys.com/), has created names including Dolby Atmos and Standard Deviant Brewing. ### Dice Roll **[MacroFactor](https://macrofactorapp.com/)** A health-focused recommendation: This macronutrient tracking app offers intuitive design and helpful feedback for managing dietary goals and overall wellness. --- ### Why Every Startup Hires the Wrong Sales Leader First *Published: 2023-01-22* # Why Every Startup Hires the Wrong Sales Leader First ### Opening Question > "How many of the voices in my head belong to others around me, and do I like that or not?" Jennifer Garvey Berger, [The Knowledge Project #43](https://podcasts.apple.com/us/podcast/the-knowledge-project-with-shane-parrish/id990149481?i=1000421932549) ### Featured Quote Leadership requires mastery in two domains: operational efficiency and capital deployment strategy. Most executives emphasize operations management, yet the most successful leaders focus equally on how they allocate generated resources across five deployment options and three funding mechanisms. William Thorndike, [The Outsiders](https://www.amazon.com/Outsiders-Unconventional-Radically-Rational-Blueprint/dp/1422162672) ## The Sales Learning Curve The core premise references Mark Leslie and Charles Holloway's 2006 Harvard Business Review paper, [The Sales Learning Curve](https://hbr.org/2006/07/the-sales-learning-curve), on sales strategy. This framework is essential reading for startup founders planning sales organization growth. ![The Sales Learning Curve](/images/essays/sales-learning-curve.png) ### Key Concept: Three Phases of Sales Development The framework identifies three distinct phases requiring different sales rep profiles: **Phase I: Initiation** - Rep type: "Renaissance Rep" - Characteristics: Creates own sales materials, comfortable with ambiguity, handles basic sales operations, deeply interested in company technology, identifies customer value opportunities - Recommendation: Hire 3-4 reps maximum - Also called "[Magical Sales Reps](https://www.saastr.com/that-first-magical-sales-rep/)" by Jason Lemkin **Phase II: Transition** - Rep type: "Enlightened Rep" - Characteristics: Learns established processes, executes against clear targets, requires more structure than Renaissance reps, expects marketing leads and formal training **Phase III: Execution** - Rep type: "Coin-Operated Rep" - Characteristics: Follows scripts and talking points, hits assigned quotas, lower compensation, easier to recruit ### Critical Metric: Sales Yield **Definition:** Revenue generated per rep divided by fully-loaded cost **Fully-Loaded Cost Components:** - Salary and commission - Taxes and benefits - Recruiting and training expenses - Software tools - Organizational overhead **Phase Boundaries:** - Break-even: Sales Yield = 1 - Traction threshold: Sales Yield >= 2 ### Common Hiring Mistake Founders frequently hire execution-phase reps for initiation-phase roles, particularly when recruiting experienced salespeople from larger, established companies. This approach fails unless the candidate has demonstrated success launching new products in early-stage environments. ## Reads & Resources ### Articles **"[Merciful Exits (On Under-Performing Executives)](https://www.edbatista.com/2021/03/merciful-exits-on-under-performing-executives.html)"** by Ed Batista explores the decision-making process for removing underperforming executives, clarifying what founders owe departing leaders versus what they don't. ### From [Twitter](https://x.com/andysparks) Martin Casado emphasizes founder-led selling as foundational; a cautionary note warns against situations where only founders can successfully sell the product, creating non-scalable revenue. ### Audio **"[#533 (Armchair Expert): Phil Stutz](https://open.spotify.com/episode/7y3gJ4A7BsMmzxfg7Nn9pm?si=5c91e7f73f574d9a)"** - Licensed therapist Phil Stutz discusses psychology and personal development; content relevant to leadership mindset and resilience. ### Books ![Who: A Method for Hiring](/images/essays/who-method-for-hiring.png) **"[Who: The A Method for Hiring](https://www.amazon.com/Who-Method-Hiring-Geoff-Smart-ebook/dp/B001EL6RWY)"** by Geoff Smart and Randy Street - Comprehensive hiring framework rated as reliable and practical methodology for building strong teams. ### Dice Roll - [Job Responsibilities Rubric](https://docs.google.com/document/d/1dMxcNgm3pQe_dR9_UjwucbxtSG1k7Wj8RFdQag5FQ-U/edit) - [Job Expectations Templates](https://docs.google.com/spreadsheets/d/16JX80AJ79_efuXEOFgnCva5BVZodawEgaZUkq_r2Jc8/copy) These templates align managers and direct reports on performance metrics and expectations, reducing miscommunication and team attrition. --- ### The Should Factory *Published: 2023-01-08* # The Should Factory Your inner jerk telling you what you "should" have done. In *The Lord of the Rings: The Two Towers*, Gandalf & Co. show up at the doors of Rohan only to find Theoden King, a frail and pale shadow of the King they expected. Sitting beside Theoden is [Grima Wormtongue](https://www.youtube.com/watch?v=iQExgALv9wI), the embodiment of the word **_scumbag_**. Wormtongue has been poisoning and paralyzing the mind of the King. Contrast [Theoden King with Wormtongue](https://www.youtube.com/watch?v=iQExgALv9wI) with the same man in *The Return of the King* screaming, "Spears shall be shaken...Ride now! Ride for ruin and the world's ending!" Each of us has our own Wormtongue taking up residence, at least part-time, in our minds. And this inner SOB does its damndest to keep us small, scared, ashamed, and weak, keeping us from becoming versions of ourselves so strong even we're surprised. Every single coaching program I've come across makes this distinction. Conscious Leadership Group calls it "Above the Line" (Theoden King calling the shots) and "Below the Line" (Wormtongue/Saruman). Reboot calls it "Right Side of the Street" vs. "Left Side of the Street." I've heard "Learner vs. Judge," "Curious vs. Furious," "Scientist vs. Litigator," and ye olde "Angel vs. Devil." And one of the easiest ways I've found to find out you're letting your inner SOB drive the car is when we use the word "**should**." **Should** is a word we use to shame ourselves and others. I always chuckle at the phrase, "Don't should yourself." I spent hours writing and rewriting the preamble and big idea for this week's Hoo Boy. I couldn't get them "right." The ideas are rich and useful, and I wanted to give them a couple more weeks to ripen. Like clockwork, my inner SOB was spinning up its propaganda machine, The Should Factory. "I should have set aside more time," "I should not have committed to writing two essays for each newsletter," "I should have known the first week back in January was a bad week to write and edit," "I should have set a different schedule," "I should have spent my evenings writing this week instead of going to the gym." Sometimes The Should Factory shares some truth. Maybe I am playing with fire, trying to write two essays every other week. But **should** comes with a hidden message of cruelty. If I weren't somehow broken, stupid, lazy, or weak, I wouldn't be scrambling to write a last-minute essay thirty minutes before my newsletter is supposed to go out. But I am, and having gotten to the end of a last-minute preamble, I'm pretty happy with what I managed to put together in an hour. I know The Should Factory is a House of Lies. If the only thing you take away from this week's issue is to pay more attention to when you and others use the word **should**, that will be enough. Should is a sign we're letting our inner SOB drive the car, and that SOB is like our personal Grima Wormtongue, whispering Saruman's black magic in our ears, blocking us from unleashing our true inner strength (Ride Now!). ## Reads & Resources ### Articles **[3 Time Management Tips That Actually Work](https://jamesclear.com/time-management-tips)** Tip no. 3 in this piece by James Clear, author of *Atomic Habits*, is "Reduce scope, stick to the schedule." And that's exactly what I did this week. I spent hours writing two different essays than the one you read above. I wanted to throw in the towel, spend next week honing the essays I drafted, and play the UNO "skip card," but instead, I reduced this week's scope, and stuck to the schedule, thereby making sure to keep the habit. ### From [Twitter](https://x.com/andysparks) **[Measuring an Engineering Organization](https://twitter.com/Lethain/status/1609924238886203397?s=20&t=UmsyatjtCF8DSJVZxwdmNQ)** Sales and marketing are easy to measure, but engineering? Whenever a team plans out a month, quarter, or year, questions invariably come up about how to measure an engineering organization (especially if the team is trying to do OKRs). This tweet screenshots part of a blog post by [Will Larson](https://twitter.com/Lethain), CTO at Calm, and I think it will be helpful to any engineer, engineering leader, executive, or CEO. ### Audio **[Work Focus 2023](https://open.spotify.com/playlist/1uQCIJ6e4hLVsAedSpi11l?si=a0f4334701b44c88)** This playlist won't be for everyone, but it's the playlist I've been using to get shit done for the last month or two, and I'll be adding to it over 2023. It's big, upbeat, loud, and intense. ### Books ![Stop Co-Founder Conflict](/images/essays/stop-co-founder-conflict.png) **[Stop Co-Founder Conflict](https://stopcofounderconflict.com/)** There's a phrase that's borderline cliche now that most startups don't die of external wounds but self-inflicted ones. In my experience, that's all too familiar. Thankfully, Dr. Matthew Jones has identified ten core causes of ineffective partnerships and laid out strategies for fixing or addressing them in his book. ### Dice Roll **[Sequoia May 2022 Founder All Hands Deck](https://www.sequoiacap.com/wp-content/uploads/sites/6/2022/06/Adapting-to-Endure_Sequoia-Capital-2022.pdf)** In May of last year, Sequoia Capital published a 52-page deck to all of their portfolio founders full of reflection on past downturns and strategies for approaching the next 12-24 months. I liked one part in particular: "Prepare your mind. Prepare your team. Prepare your company." If you're a founder or CEO, I recommend setting 20-30 minutes aside to scroll through and take notes. --- ### Startup States: Jungle, Dirt Road, Highway *Published: 2022-12-18* # Startup States: Jungle, Dirt Road, Highway ## Hard Work vs. Overwork Andy Sparks opens by distinguishing between genuine hard work and overwork. He compares startup founders to Olympic athletes, arguing that sleep, exercise, and diet should be viewed as performance requirements rather than luxuries. Neglecting health can manifest in physical stress symptoms, decreased decision-making ability, and eventual burnout. ## Three Startup Phases Based on Jeff Bussgang's framework from [*Mastering the VC Game*](https://www.amazon.com/Mastering-VC-Game-Venture-Start-up/dp/1591844444), Sparks explores three distinct phases of startup maturity: ### The Jungle - Uncertain direction; no product-market fit yet - Experimental phase exploring potential opportunities - May require pivoting or changing direction ### Dirt Roads - Product-market fit achieved; early revenue stage - Focus on expanding market presence and revenue growth - Challenges include hiring sales teams, developing managers, and maintaining customer focus ### Highway - Mature company phase (500-8,000+ employees) - Shift from revenue growth to profitability and cash flow - Companies preparing for or at IPO stage ## Critical Mistakes and Best Practices Sparks identifies common CEO errors when operating in the jungle phase: **Working Hours:** Jungle startups demand extended hours. Team members uncomfortable with this intensity belong at later-stage companies. **Leadership & Ownership:** Leaders must go first, set tone, and ensure clear ownership of specific responsibilities across the team. **"Whatever It Takes" Mentality:** Role rigidity kills jungle-stage companies. Everyone must focus on escaping the jungle rather than title protection. **Beware of Premature Structure:** Building "dirt roads" while still in the jungle wastes energy. People anxious about ambiguity sometimes create unnecessary processes instead of pushing forward. ## Key Quote Patrick Collison, Stripe CEO: "people's disposition with regard to the company is actually a function of what they feel like they signed up for." ## Reads & Resources ### Articles - "[The 3 Financial Plans You Need for The Year](https://www.saastr.com/the-3-financial-plans-you-need-for-next-year-c-90-c-60-and-c-10/)" - Jason Lemkin discusses C-90, C-60, and C-10 confidence intervals for planning ### From [Twitter](https://x.com/andysparks) - Michael Girdley's thread on customer profitability analysis warns against investing heavily in low-revenue customers ### Audio - Hugh Jackman's Tim Ferriss interview praised for groundedness and family-first decision making ### Books ![The Tools by Phil Stutz](/images/essays/the-tools-phil-stutz.png) - [*The Tools*](https://www.amazon.com/Tools-Courage-Creativity-Willpower-Inspire/dp/0812983041) by Phil Stutz - addresses self-expression, confidence, and emotional regulation ### Resources - Faith Meyer's Job Responsibilities Rubric - practical performance management templates --- ### 1800's Wisdom: Three Components of a Business *Published: 2022-12-04* # 1800's Wisdom: Three Components of a Business American business has become a story of small heroes and scaled-up villains. ## The Backstory Two weeks ago, Pew Research published [a study](https://www.pewresearch.org/fact-tank/2022/11/17/anti-corporate-sentiment-in-u-s-is-now-widespread-in-both-parties/) on public sentiment toward business in the United States. - 80% of Americans said small businesses "have a positive effect on the way things are going in the country these days." - When applied to technology companies, that number shrunk to 49%. - For big business, the ratings were scathing: 71% of Americans felt "large corporations had a _negative_ effect on the way things are going." ## Why it Matters As founders of startups, you may hope your business becomes a large corporation, but most likely you're not interested in 71% of Americans thinking your creation harms society. The critical question is: what makes large corporations so problematic that small businesses avoid, and how can startups prevent transforming from hero into villain? ## Andrew Ure's Three Systems of a Factory When defining management or business simply, it communicates easily but loses inherent system complexity nuance. ### Theory Andrew Ure lived in Glasgow, Scotland, in the early 1800s. After earning degrees in chemistry and natural philosophy, Ure took a position at Anderson's Institution, a school founded to educate factory workers and managers. He taught and trained many owners and managers of major UK factories during the first half of the century. A widespread early 1800s issue involved workers skipping work or stopping entirely, leaving proprietors with chaos. To address this, Ure argued factories needed three harmonious systems, compared to "the muscular, the nervous, and the sanguiferous systems of an animal": ![Andrew Ure's three systems](/images/essays/andrew-ures-3-systems.png) 1. **The Moral System**: "The condition of personnel." 2. **The Mechanical System**: "The techniques and processes of production." 3. **The Commercial System**: "Sustaining the organization through selling and financing." ### Practice Founders need to zoom in and out on their business, seeing both forest and weeds without getting lost. Models like Ure's help counter the human tendency toward unnecessary complexity. Startups excel at assigning fancy titles and scheduling meetings more than solving the core issue. For example, pre-product-market-fit companies often have a CEO, VP of Product, Head of Engineering, Head of Sales, Head of Marketing, and numerous other positions without any actual strategy for reaching PMF. Ure's system asks: (1) Does someone ensure we have the right people and they're satisfied? (2) Does someone own knowing what to build and how? (3) Does someone own selling and maintaining sufficient cash reserves? The simplicity is compelling, though objections will arise about facilities, administration, marketing, analytics, and other unlisted functions. The counterargument: if individuals own each of Ure's systems, all other functions emerge naturally to achieve those goals. In [a 2017 piece](https://feld.com/archives/2017/01/the-three-machines/), Brad Feld broke business into three "machines": (1) the product machine, (2) the customer machine, and (3) the company machine. Feld notes that sub-scale leadership teams (roughly 3 founders and 4 employees) allow a CEO to own one machine, but not more. Beyond roughly 20 employees, ideally one person owns each. ## Reads & Resources ### Articles **[How We Get Hooked and Unhooked](https://www.lionsroar.com/how-we-get-hooked-shenpa-and-how-we-get-unhooked/)** Irritation, frustration, anger, anxiety, and fear are universal experiences. This piece explores _Shenpa_, a Tibetan concept describing the mental state triggered by unpleasant feelings that tempts us toward amplifying actions, like scratching a mosquito bite applied to life. The article provides practical tools for avoiding such patterns. ### From [Twitter](https://x.com/andysparks) **[Regina Gerbeaux on Engineering Structures That Help Startups Move Insanely Fast](https://twitter.com/_rpgbx/status/1594750681675870208?s=20&t=s6f0CcdtNYt9JdzHPxAC-w)** Regina, former COO at Mochary Method (led by Matt Mochary, author of _The Great CEO Within_), publishes practical guides as an executive coach to high-growth companies. Anyone would benefit from following her work, particularly Chiefs of Staff. ### Audio **[Dr. Wendy Suzuki on Boosting Attention & Memory](https://podcastnotes.org/huberman-lab/episode-73-dr-wendy-suzuki-boost-attention-memory-with-science-based-tools-huberman-lab/)** This Huberman Lab episode features Dr. Suzuki, a prominent memory researcher. A standout section covers four factors making information memorable: (1) novelty, (2) repetition, (3) association, and (4) emotional resonance. ### Books ![How to Castrate a Bull](/images/essays/how-to-castrate-a-bull.png) **[How to Castrate a Bull](https://www.amazon.com/How-Castrate-Bull-Unexpected-Business/dp/0470345233)** By Dave Hitz, co-founder and Founder Emeritus at NetApp (Fortune 500 for nearly a decade), this underrated business book particularly serves scaling founders. It shares practical, humorous stories about shifting roles as co-founder, building the business, handling challenges, and observing co-founder and CEO development. ### Dice Roll **[The Ultimate Annual Review](https://www.schlaf.co/lightwaves010/?ref=schlaf-conscious-compassionate-change-newsletter)** This isn't a performance review, it's year-end reflection practice. Steve Schlafman's template helps slow down, consider what happened, and envision next year. For mental clarity heading into 2023, download the template and complete his exercises during winter break. --- ### The Roots of Your Obsession *Published: 2022-11-13* # The Roots of Your Obsession What do you find **so interesting** that it out-competes Netflix for your attention? People are astoundingly unique thanks to not only our genetics but all the stuff that happened to us, and because of us, that shaped who we are. And I'm convinced that when someone's bored or stuck or feeling trapped or any other flavor of **_unmotivated_**, it's because we're not putting that peculiar combination of experience to good use. The things we're **_interested in_** are the clues to becoming more aware of what makes us so damned unique. For example, it took me a while to realize that my interests, learning and listening to other people, writing, making stuff look pretty, and wondering how to make work prosperous for employers **_and_** employees, could be combined into not only a real career but one with more freedom and lightness than anything I'd ever done before. So how do you unlock an insight like that? That's where my question, **what do you find so interesting that it could beat Netflix in a competition for your attention**, comes in. Maybe your answer is **_nothing_**. But if you think for a second about what **_might happen,_** most of us can find some clues. Whatever this thing is, we have a lot of words for it. _Obsession_ is the most common. Brie Wolfson calls it [**person-problem fit**](https://manual.withcompound.com/chapters/finding-person-problem-fit). Robert Greene calls it [**_your life's task_**](https://www.amazon.com/Mastery-Robert-Greene/dp/014312417X). It's been called a **_calling_**. Tim Urban calls it the [_non-negotiable bowl at the top of your yearning hierarchy_](https://waitbutwhy.com/2018/04/picking-career.html). But my favorite is _a monomaniacal preoccupation._ ## Why Does it Matter? People who find something to be monomaniacally preoccupied with, something that would out-compete whatever their Netflix-equivalent attention siphon is, are **_unusually motivated_** and have a history of producing great work regardless of their field. - Historian Dean Keith Simonton, who may have studied [the nature of genius and greatness](https://www.amazon.com/Greatness-Who-Makes-History-Why/dp/0898622018) more than anyone else, believes that almost all human motivation boils down to "a single activity, a monomaniacal preoccupation." - Similarly, the poet David Whyte says, "the antidote to exhaustion is not rest; it is **wholeheartedness**." ## The Bottom Line [Gallup](https://www.gallup.com/workplace/388481/employee-engagement-drops-first-year-decade.aspx) reports only 34% of U.S. employees feel engaged at work, and I can't help but wonder if some of that has to do with heaps of monomaniacal preoccupations awaiting claiming. This week I'm going to skip over how one _finds_ an obsession and skip straight to what to do with one once you've found one. ## Big Idea #9: The Obsession Tree ### Theory Every obsession has a legacy, and we can choose to ignore it or embrace it and save ourselves years of painstaking rediscovery and reinvention. Imagine a family tree, but on this tree, the people aren't connected by birth and heredity. Their obsessions connect them. Unfortunately, we aren't born with our hard drives pre-loaded with all the stuff our obsession ancestors figured out before we showed up on the scene. If you feel like you get it, skip to the practice section. But if I've learned anything from non-fiction authors, you have to say what you're trying to say in ten or twelve different ways to get a book deal, so here's another way to think about it. In a lot of video games, your character's level and power increase as you complete missions. You start at zero, and there's usually a max level of 20-100. But in life, it's like the person who discovered the wheel went from level 0 to level 1 in their life, but you can go from level 0 to level 2,356 by studying what all the other wheel-obsessed folks did before you showed up. Another way is to think of the generational transfer of obsessions as a baton, an Obsession Baton. Obsession Batons aren't some magical objects we can pick up, but they're choices imbued with incredible power. As we pick up our batons, we can look back and learn from those who handed them to us. Or we can take the sicko-route and ignore history and risk letting our branch of the tree wither and crumble. And if that wasn't enough, here's another way to put it (I can nearly hear Penguin's agents scrambling, can you?): I've sometimes heard tracing the lineage of your intellectual heritage as "going to the source." As in following a river upstream to find the source of the water. The further upstream you go, the further ahead you'll be able to see (because elevation, you know). ### Practice Anyone can, at any moment, begin to map both the _lineage_ of who's held the obsession baton before you and your other **living intellectual relatives**. Einstein needed to study Newton and Galileo, Faraday and Maxwell. Still, in Hendrik Lorentz's 1905 paper, a man only twenty-six years his senior, he discovered equations he needed to develop his Theory of Relativity. As a CEO, your obsession may be a customer problem. So who was obsessed with it before you? Who is obsessed now? As a designer preoccupied with typography, you're sure to realize that [Matthew Butterick](https://practicaltypography.com/) is carrying a baton for typography, and so are Kris Sowersby and the team at [Klim Type Foundry](https://klim.co.nz/). It gets really cool when you're carrying two batons from different fields, and you get to mash them up in a sort of industrial version of combining two cuisines in delicious fusion. The point is simple: when you find something that beats Netflix in a battle for your attention, two places you can look to further your knowledge are to the past, who's been obsessed before, and to the community of others who share your obsession. ## Reads & Resources ### Articles **[Homebrew Ventures' Guide to Executive Coaching](https://coda.io/@homebrew/executive-coaching)** For years, [Beth Scheer](https://twitter.com/homebrewbeth) at Homebrew has been writing helpful long-form guides for startup founders on topics like [diversity](https://quip.com/7GSaAovqAPEh), [immigration](https://quip.com/Y0rRAWZrVReG), [benefits](https://quip.com/BGenAiTcbxGo), [onboarding](https://quip.com/h3efABIaaG4y), [compensation](https://quip.com/HEB3Ah9dYD6o), [sourcing talent](https://quip.com/wuTHAU3kmiKh), and [performance management](https://quip.com/MwcgA10sGgFC). Each one is **_awesome_**. This one on executive coaching is so good that I recommend any potential client I speak with read it before we talk, and it's a great place to point people out if they have questions about coaching. ### From [Twitter](https://x.com/andysparks) **["The Biggest Cost Reduction That Took Me Too Long to Learn"](https://twitter.com/AlexHormozi/status/1587593900541505536?s=20&t=DMXxfcoGnKY4NZxS08iQLg)** Alex Hormozi, the founder of [Acquisition.com](http://acquisition.com/), tweeted, "Biggest cost reduction that took me too long to learn: Pay A-players 1.5x market rate to get 5x the output of a B-player." This is wisdom that goes way back. Frederick Winslow Taylor, an early management theorist in the late 1800s and early 1900s, called this the "paradox of high wages and low costs." Many incorrectly think of high wages as a cost, reducing overall profits. Still, the idea is that when great people are incentivized right, the interests of the employee and employer are aligned, leading to a general increase of the pie being split. ### Audio **[Lenny's Podcast: Matt Mochary](https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/)** I read and listen to just about anything Matt puts out these days. Before I was a coach, I'd refresh the Google Doc for **The Great CEO Within**, waiting for a new chapter to drop. Today, I regularly refer to Matt's methodology and tactics for building companies with my clients. He shares his ideas generously, and I love how sincerely he cares about building great companies that work for the employers **_and_** the employees. My favorite part of this episode comes early when he talks about how he makes a bet with CEOs he coaches that ends up helping them become aware of just how often fear is driving them to misjudge situations. ### Books ![WTF?: What's the Future and Why It's Up to Us](/images/essays/wtf-whats-the-future.png) **[WTF? What's the Future and Why it's Up to Us](https://www.notion.so/WTF-What-s-the-Future-and-Why-it-s-Up-to-Us-05810ceb8eac4dd4899a4e48feff9571)** This is one of my most heavily highlighted books of all time. The book's author is Tim O'Reilly, who created one of the first e-commerce marketplaces on the web, coined the term "open source," and founded O'Reilly Media, the publishing company behind the technical books with the animals on the covers. It's one part of history, arriving at some conclusions about "how we got ourselves here," and then another part, "what to do about it." My favorite part is where he describes "the market" as humanity's first AI, one few of us are conscious of spending our lives feeding. ### Dice Roll **[SparkToro's 2021 Food & Drink Gift Guide](https://sparktoro.com/blog/the-best-damn-food-drink-gift-guide-2021/)** Last year I bought almost every gift I gave friends and family off this list. The list is full of delicious items I didn't even know existed, and the gifts were all hits. I tweeted [Rand](https://twitter.com/randfish) and [Amanda](https://twitter.com/amandanat) to ask if they'd be doing a 2022 version, and they confirmed they would. But for those of you who want to get started earlier, this is the ticket. --- ### If Someone Quits, Who Will Replace Them? *Published: 2022-10-30* # If Someone Quits, Who Will Replace Them? Welcome to Issue #8! Management fundamentally centers on listening, to oneself, one's team, and customers. ## Newsletter Goals In April and May 2022, Sparks established three objectives: - Identify a topic engaging enough to sustain a year of newsletter content - Write about subjects he genuinely finds interesting, inspired by [Morgan Housel](https://twitter.com/morganhousel)'s approach - Grow the audience sufficiently to market future services through the newsletter alone ## Growth Metrics The *Hoo Boy* newsletter has grown from 132 initial subscribers (late July) to 323 subscribers. The publication maintains a 59% open rate and 14% click rate. ## Big Idea #8: Bench Building **Core Concept:** Exceptional managers cultivate relationships with talented professionals well before job openings materialize. ### Why This Matters Bench building addresses the gap between important and urgent tasks. Without proactive relationship-building: - Organizations must start recruitment from scratch when positions unexpectedly open - Talented professionals are typically employed and unmotivated to change jobs without established connections - The compressed hiring timeline creates unnecessary pressure ### Strategic Application Leaders responsible for product, design, or engineering teams should continuously network with potential candidates across these disciplines. This preparation ensures readiness when departures occur due to circumstances beyond the organization's control (relocations, family changes, etc.). ### Bottom Line Planning and anticipation constitute core managerial responsibilities. Managers without cultivated candidate relationships fail this fundamental duty. Those who recognize this gap gain opportunity for professional development. ## Reads & Resources ### Articles **Elad Gil's "[Hiring Executives](https://growth.eladgil.com/book/chapter-4-building-the-executive-team/hiring-executives/)"** from [*The High Growth Handbook*](https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100) recommends defining roles before identifying candidates, essentially advocating bench-building methodology. ### From [Twitter](https://x.com/andysparks) **[Simon Sinek](https://twitter.com/simonsinek) on Experience Premium:** Sinek explains why experienced hires command higher compensation: "I pay them more for a skillset I hope we never have to use." ### Audio **Jennifer Garvey Berger's "The Mental Habits of Effective Leaders"** explores the Constructive Development Framework for leadership growth. Notable insight: "A great leader makes you feel bigger when you're in the room with them." ### Books ![Hell Yeah or No by Derek Sivers](/images/essays/hell-yeah-or-no.png) **[Derek Sivers](https://twitter.com/sivers)' "[Hell Yeah or No](https://sive.rs/n)"** presents decision-making frameworks considering happiness, long-term benefit, and usefulness to others. ### Dice Roll **[Tom Killion's Woodcut Prints](https://tomkillion.com/):** Japanese-style handmade woodcuts depicting California landscapes. --- ### The Story Behind My Latest Project, Hoo Boy. *Published: 2022-10-23* Welcome to Issue #11! **Captain's Log:** October 23, 2022, San Francisco, CA, written entirely by a human. The star of this issue is my latest project: Hoo Boy. It's a newsletter I send every other week where I write for founders navigating how to manage (1) themselves, (2) their team, and (3) their company. If that sounds fun, sign up here or read an issue [here](/essays/issue-5-non-obvious-management-responsibility). Two newsletters from one person might be confusing, but I'm keeping Captain's Log and Hoo Boy separate. Captain's Log is personal (and sent ~2-4x / year), and Hoo Boy is about my work (and sent 2x / month). Sometimes there will be overlap, but I figured folks would prefer to opt-in to something sent more frequently. One of the main reasons I write Captain's Log is that I think people dig reading an honest perspective from someone trying to figure out their life and career. So, below, you can read about where Hoo Boy came from and why it's something you can count on to stick. ## Where Hoo Boy Came From I began coaching founders in the summer of 2020. I immediately found that I loved it and was pretty good at it. But I've felt like something is missing in the two years since. It was like nachos without tortilla chips, Oreos without the cream filling, a Rick without his Morty. These things are all good, but they're incomplete. I've been trying (and failing) to fill that void with creative stuff ever since, so when I felt stuck again in April, I slowed down, zoomed out, and took everything I've learned about helping clients and applied it to myself. And it turns out the stuff works. My biggest insight was that I needed to find a topic that I found so interesting that it could readily compete with just about anything else for my attention and win. When studying the research on human motivation, Dean Keith Simonton ([Greatness](https://www.amazon.com/Greatness-Who-Makes-History-Why/dp/0898622018), p. 141) wrote: "...we might do better to say that all the motives that can stimulate the energies of the human being all converge on a single activity, a monomaniacal preoccupation." The normal-person language version of this is probably "obsession," but obsession calls to mind the lady in the Starbucks line talking too loud on her phone, "Oh my god, I am obsessed with oat milk." To be monomaniacally preoccupied hits different. If there's a spectrum from 0 - 100 of how monomaniacally preoccupied you are, at 100, you'd always choose to spend time on that thing over your family, friends, Netflix, exercise, or anything else. I think my optimal level of preoccupation is north of 50 and under 100--the thing would be able to compete (and win) most of the time, but I wouldn't be a slave to it. After some digging, I found that almost all the work I've loved doing the most has to do with understanding how people effectively organize to solve problems for other people in a way that doesn't suck for the people involved. Some people might call this "management," but it's probably "management that doesn't suck." I keep coming back to this topic for at least two reasons: one from watching my Dad work as I grew up and one from my own experience starting and building companies. First, I grew up watching my Dad come home from work in a foul mood that made it clear "work" must essentially be Mordor, and I'd later listen to him advise me to choose work I'd enjoy. To some extent, I want to save all the parents and kids from stress, dark moods, ensuing arguments, and so on. To call it easing suffering feels dramatic, but that's what it is. Second, I've started three companies and coached more than 30 founders. [Quit](https://www.penguinrandomhouse.com/books/692752/quit-by-annie-duke/)ting your job, coming up with an idea, and getting product-market-fit ("PMF") is hard enough. But after a founder gets PMF, they have to become reasonably competent in an uncanny number of new areas and skills in a short period or face the market's gallows. They have to understand the essential functional components of a business: sales, marketing, finance, engineering, product, operations, and more. But wait, there's more: learning about performance management, hiring, firing, handling gossip, interpersonal conflict, time management, planning and retrospectives, and structuring meetings is a lot. Now, management that doesn't suck is something many of people could get interested in, but if I've learned one thing from my experience founding companies and coaching others, it's that a broad audience may as well be no audience. So instead of starting with an ambition to create a grand unified theory of management for all millennial managers, I'm starting with the folks who've taken the leap to start their own business and have self-selected into being willing to try their best to learn whatever they need to for their business to succeed. Hoo Boy is where I'll be writing about that journey, and while I have other aligned project ideas, I'm going to let those marinate for a bit longer before sharing anything about them publicly. ## Why You Can Count on Hoo Boy Not to Disappear To learn from past experiences, I did two things differently with Hoo Boy. First, I slowed myself down after feeling "ready," making myself wait two months before getting started to make sure my whole heart was in Hoo Boy. Second, I made sure I was committing not just to start the newsletter, I was committing to publishing for at least a full year. I've quit a lot of stuff, and I wanted this newsletter to be different. All three companies I started, I quit. The first, I quit after a year. The second and third, after four years each. And since the third, I've started and stopped several projects after only a few months. When I looked for patterns, I discovered that when I find myself in-between projects, the anxiety of doing nothing leads me to rush into something my whole heart isn't in. Months (or years) later, I inevitably decide to be honest with myself, and then I quit. The most interesting part is I always knew the thing wasn't right for me really fast after committing, but then I couldn't get over the sunk costs and summon the courage to call it quits. So this time, I put myself on pause when I felt "ready" to get started on Hoo Boy, redesign my website, announce the thing, and write the first issue. I committed to waiting two months before writing my first issue. If I were still excited on July 15th, I'd have passed the period where I'd usually have realized I'd committed to something halfheartedly, and it was safe it proceed. The other insight I had was that it's really easy to start something if you think of it as an experiment, and that's a good thing. But this time, I didn't want an experiment, I wanted something I could commit to and others could rely on. So instead of committing to start writing a newsletter, I committed to publishing it for an entire year. So that's a long-winded way of saying this thing ain't going anywhere, at least for the year. But so far, I've been loving writing it in a big way, so I anticipate it will go on much longer. The first issue went out July 24th, and issue eight goes out next Sunday. Sign up here. ## Major Events - **Summer Vacation**: In July, I took two concurrent weeks off for summer vacation for the first time since grade school (and even then, I worked 40+ hours most of the last few summers). For the first week, I flew out to Columbus, Ohio, a full week before one of my best college friend's wedding. I caught up with a ton of old college friends who I hadn't seen since before the pandemic. After that, Kate and I visited her family in New England. But the best choice of all, I think, was to come back home on a Thursday, so I still had a three-day weekend ahead to settle back in. ## Projects - **Hoo Boy**: I already told you about this in the preamble. So sign up! - **Continuing Education**: I came across the word philomath a few years back. It means "lover of learning," and it continues to resonate. There are three big areas I've spent the last six or so months learning more about: design (I do all my graphics & website), writing, and management. Some books I've been making my way through: Greatness, [Grid Systems in Graphic Design](https://www.amazon.com/Grid-systems-graphic-design-communication/dp/3721201450), Quit, [The Ancient City](https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048), [The History of Management Thought](https://www.amazon.com/Evolution-Management-Thought-Daniel-Wren/dp/0470128976), [The Managerial Grid](https://www.amazon.com/MANAGERIAL-GRID-LEADERSHIP-ACHIEVING-PRODUCTION/dp/B000H7GSHK), and [A Game Free Life](https://www.amazon.com/Game-Free-Life-definitive-Compassion/dp/0990586707). - **Being a Better Boyfriend**: Kate and I crossed our three-year anniversary this July, and we're both big believers in actively investing in learning how to be better partners. We recently found it helpful to learn more about attachment theory through Dr. Sue Johnson's [Hold Me Tight](https://www.amazon.com/Hold-Me-Tight-Conversations-Lifetime/dp/1491513810). I also continue to find Ester Perel's belief that when couples argue, it's almost always about one of three things: (1) power and control, (2) closeness and care, or (3) respect and recognition. - **[Blue Dot](https://www.lookbluedot.com/)**: In 2021, I announced a new brand for my coaching work, Blue Dot. I went all in on becoming "the climate coach." I was hot off of seeing the sky turn Blade Runner orange in San Francisco, reading apocalyptic climate fiction, and I was really enjoying working with a couple of clients addressing climate change in some way. In retrospect, I went all in too soon. It's not that I suddenly don't care about Climate Change (I do). I continue to work with several climate-focused founders, but folks continue to introduce me to great founders outside of climate, and it feels strange to say no if I feel like there's a fit. On top of that, while I enjoy my work with climate founders, I'm drawn to learning and teaching about management more than I am to do the same for climate. So I've decided to sunset the Blue Dot brand and keep all of my work on andysparks.co. ## Top 5 Recommendations 1. **[The Realm of the Elderlings Series by Robin Hobb](https://www.amazon.com/Assassins-Apprentice-Farseer-Trilogy-Book-ebook/dp/B000FBFMG6/)**: I've spent the last year reading all twelve books in this series. Twelve books are enough to make most people say, "Aw hell naw." But Robin's broken the series up into four trilogies, each of which I turned through faster than a ten-year-old powering through a new Harry Potter release the day it came out. I genuinely spent an entire hour-long bus ride crying as one of the trilogies wrapped up. The series follows Fitz from boyhood to old age in a world with mysterious magic, realistic politics, wonderful friendships, and characters you won't forget. This is now my favorite fantasy series of all time. 2. **Lex--AI Powered Writing Assistant**: Last week, my friend [Nathan](https://twitter.com/nbashaw) DM'd about a "thing he was coding" to get some feedback. Turns out, that thing turned out to be a basic but cleaner version of Google Docs with a GPT-3 integration to help you get unstuck when you're writing or brainstorming title ideas--check out the demo here. Nathan's went from launch to having his logo on Sequoia Capital's Generative AI Market Map in under 24 hours, so needless to say, the hype is real with this one. But having given it a shot, it's one of those things that, after you use it, you say, "Of course this was going to exist." And I look forward to seeing it get better. 3. **[Grapefruit + Mangosteen Candle](https://www.basikcandle.com/collections/candles/products/grapefruit-mangosteen-candle?variant=39546730217637)**: I've no idea what mangosteen is, but what I can tell you is that this candle smells incredible. Our downstairs neighbor had been burning it last month, I asked about it and immediately bought one from the shop down the street. 4. **[Smart Brevity](https://www.amazon.com/Smart-Brevity-Power-Saying-More/dp/1523516976)**: If you've ever read a newsletter by Axios, you've seen Smart Brevity in action, as it's their methodology for writing in a way that captures people's attention. I decided to pick the book up and give the style a whirl in my [last issue](/essays/issue-7-are-you-living-in-the-land-of-broken-promises) of Hoo Boy, and I found it was a helpful way to keep myself honest about whether I was filling my writing with fluff or not. At a minimum, it's a helpful companion for anyone interested in becoming a more succinct and clear communicator. 5. **[A Travel Bag for All Your Cables](https://www.apple.com/shop/product/HMW92ZM/A/incase-nylon-accessory-organizer?fnode=966e97c2db449d2253fc47530e6dc3611e4b886e2b9093c8bb145e344a42b199fb0b535fbf4767c21f36cb1adf2987c2e201a44b7e6db91e5a87ae241bff3c61af28ec1874e1b2bcf8b9c44f713a775d2d6239f6e4299e9b4cf752011381380a)**: When I travel, I bring my phone (and cable), my Kindle (and charger), my battery pack (for my phone that doesn't hold a charge), my AirPods, my watch (and charging cord), and so on. My backpack used to be a mess of cords, usually some missing. I saw a buddy had this bag for his cables on a trip in May and decided to get one for myself and pre-stock it with all the cords I need for travel so I'd never have dead batteries again. Top 5 summer purchase. ## Asks - **New Coaching Slot**: A client of mine recently "graduated," and I have a new slot opening up in November. If you know any founders who are at or near product-market fit, looking for a coach, and loves the learning process, I'd love to speak with them. You (or anyone else) can learn about my coaching [here](https://www.notion.so/Coaching-with-Andy-b463d69cb7f44db8bf171875c3f3834a). That's all for this week. I'm looking forward to what's next! Andy. --- ### The False Cultural Promises of a CEO *Published: 2022-10-16* # The False Cultural Promises of a CEO Welcome to Issue #7! Last week I promised to share my bite-sized definition of management. So [here](https://growth.eladgil.com/book/chapter-5-organizational-structure-and-hypergrowth/you-cant-delegate-culture-an-interview-with-patrick-collison/) goes. **Management** is how we organize people and things to solve problems for other people. ## Why it Matters It's hard to fix something if we can't describe it. Understanding management decisions and tradeoffs, ranging from dysfunction to excellence, is crucial for a brighter future where people benefit from productivity. ## The Backstory Management shapes our lives through its impact on markets, moods, salaries, and more. Despite industrial progress, management underperforms: - [50% of Americans have left a job](https://www.gallup.com/services/182138/state-american-manager.aspx) to escape their manager - Only [36% of employees report feeling engaged at work](https://www.gallup.com/workplace/352949/employee-engagement-holds-steady-first-half-2021.aspx) - Even doubling engagement would still yield substandard results ## The Bottom Line Before improving management, we must develop shared language about what it is, what it should accomplish, and where it fails. ## Big Idea #7: The Land of Broken Promises [The Managerial Grid](https://www.amazon.com/MANAGERIAL-GRID-LEADERSHIP-ACHIEVING-PRODUCTION/dp/B000H7GSHK) framework (based on Robert Blake & Jane Mouton's 1964 model) visualizes management styles across two dimensions: concern for people and concern for production. ### Theory Managers often operate in what I call "the land of broken promises," claiming high concern for both people and production while delivering neither. As [Patrick Collison](https://twitter.com/patrickc) noted, "people's disposition with regard to the company is actually a function of what they feel like they signed up for." Startups particularly struggle with this gap, promising fast-paced, people-friendly cultures that fail to materialize. ### Practice **How to Use It:** 1. Plot where you believe your management style falls on the grid 2. Ask your team where they perceive your style 3. Compare self-perception with team feedback 4. If desired, set goals for shifting your style 5. Communicate changes to your team and request ongoing feedback ![Broken promises in practice](/images/essays/broken-promises-in-practice.png) **Example:** A manager believing they excel at both dimensions discovers their team sees them as production-focused but dismissive of people concerns. After adjusting to prioritize production, they swing too far and neglect people. **The Bottom Line:** Self-awareness enables accurate expectations and behavioral goals that improve both employee experience and organizational performance. ## Reads & Resources ### Articles **[Madman, Architect, Carpenter, Judge: Roles and the Writing Process](http://www.ut-ie.com/b/b_flowers.html)** This piece addresses internal criticism that blocks writing productivity by distinguishing roles in the creative process. ### From [Twitter](https://x.com/andysparks) **[What do 500 people in tech want to see from their employer?](https://twitter.com/briannekimmel/status/1580303623073910785?s=20&t=eDe3-CGY6c4--hVVmXF2mQ)** Bri Kimmel surveyed 500 tech workers. The top request was straightforward: *paid holidays*. ### Audio **[Invest Like the Best #204: Sam Hinkie](https://podcasts.apple.com/us/podcast/invest-like-the-best-with-patrick-oshaughnessy/id1154105909?i=1000502455395)** [Sam Hinkie](https://twitter.com/samhinkie), founder of [87capital](https://www.87capital.com/) and former Philadelphia 76ers GM, discusses building meaningful relationships in a thoughtful podcast conversation. ### Books ![Quit by Annie Duke](/images/essays/quit.png) **[Quit: The Power of Knowing When to Walk Away](https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996)** [Annie Duke](https://twitter.com/AnnieDuke)'s new book explores strategic withdrawal. A CEO friend noted: "I took more actionable stuff away from listening to her speak for 45 min than most speakers combined." ## Dice Roll **[Confirm](https://www.confirm.com/)** This startup reimagines performance evaluation by incorporating feedback from employees' networks, recognizing that "the network around an employee often has a different opinion than their manager." --- ### We Don't Have a Word for a Great Business Culture *Published: 2022-10-02* # We Don't Have a Word for a Great Business Culture The wonderful citizens of the Internet decided to name The Feynman Technique after [Richard Feynman](https://en.wikipedia.org/wiki/Richard_Feynman), one of my heroes. While endless bloggers all seem to know the technique, it's not clear he ever described it as we now know it. The gist is that if you can't explain something to a child, you don't understand it. The child's age in question ranges from six to a [freshman in college](https://www.notion.so/6253f46ff28c45b69b298e50d387d79f). Wherever it came from, it's a helpful exercise to make sure I'm not on Mount Stupid when I think I'm sun-tanning on the Plateau of Actually-Knowing-What-You're-Talking About (see: [Dunning-Kruger Effect](https://commons.wikimedia.org/wiki/File:Dunning%E2%80%93Kruger_Effect_01.svg)). So. Hoo Boy is about upgrading how you manage yourself, your team, and your business. So what _is_ **management**? Can we explain it to a six-year-old? A ten-year-old? A college freshman? If I were to tell my ten-year-old nephew that his uncle is a _firefighter_, he'd get it. And most firefighters would agree on what it is that a firefighter does. If I were to tell him his uncle is a _manager_, though, I don't think he'd grok the gist of it. And I'm confident that most managers, unlike the firefighters, would give wildly different answers. **I'll give you my working definition in the next issue.** But here's a challenge for you: write down _your definition_ of what a manager does in simple enough terms that a ten-year-old would get it, and reply to this email with your best shot! ## The Blake-Mouton Managerial Grid The Mouton-Blake Managerial Grid, from [*Breakthrough in Organization Development*](https://hbr.org/1964/11/breakthrough-in-organization-development) (1964) ## Theory Back in 1964, Robert Blake and Jane Mouton published an article in Harvard Business Review titled, *Breakthrough in Organization Development* based on research from 1962-1963 with a large plant with about 4,000 employees. In the piece, **they introduced two key ideas**: 1. **A Graphical 2-by-2 Grid**: This legitimately _may have been_ the first use of a visual 2x2 grid. That sounds insane to me, but the way Mouton & Blake talk about the grid, "New to most executives in concept and design," threw a flag for me to do some light googlin', and it turns out someone else already did and couldn't find one! (thanks to Noah Brier for [doing the research](https://whyisthisinteresting.substack.com/p/why-is-this-interesting-the-2x2-edition)). 2. **Management as a Function of Concerns for People & Production**: The Grid, literally referred to with a capital G because they thought it was so cool, encouraged managers to think about how different management styles arise when managers have different degrees of concern for **people** and **production**. The pinnacle of management, according to Mouton & Blake, is an organization where members trust and respect one another _and_ achieve the business's production goals. **Why this was a big deal**: the study proved better management, in terms of increased production and happier people, was something you can teach. - The study led to a 31% savings, "amounting to several million dollars," from "improved operating procedures and higher productivity per man-hour," _and_ 49% of workers reported an overall improvement in "the way they work together with their boss." **My favorite part**: the workers and managers in the plant began referring to certain types of behavior as "9,1 behavior" and "9,9 behavior." Here's a paraphrased version of a quote, "If this problem came up a year ago, we would have used a 9,1 on it, told the complainer to go back to work." **Nuances to take note of:** - I digitized Mouton & Blake's graphic with as much fidelity possible. The five boxes call out four extremes and a middle-point management style, but that doesn't mean they're _the only configurations_. The DMV, for example, _may_ be run via 1,1 management, but I bet it's closer to 2,3 or something like that. - Mouton & Blake emphasize that "**the term 'concern for' refers to the degree of concern, not the actual results**." Call me crazy, but I believe a management team can operate with a 9 out of 9 concern for people and still make mistakes that call for layoffs. ## Practice The application of a 2x2 always yields one thing regardless of the axes: the knee-jerk desire to call out how reality isn't reducible to two variables. And it's not, but that's not the point. The point is to _play with the ideas_. ![Mouton-Blake Managerial Grid simplified](/images/essays/mouton-blake-managerial-grid-simple.png) I set out to give each box a name, inspired by Ed Batista (in [this piece](https://www.edbatista.com/2019/04/accountability-and-empathy.html)), but I couldn't come up with _one word_ that fits in the 9,9 management box. So I DM'd, texted, and tweeted, asking for help. I knew I was onto something when people responded with skepticism and cynicism about whether 9,9 management is even possible. **And I righteously call bold bullshit on that**. 9,9 management may be _temporary_ or unsustainable. Maybe the best we can hope for is 7,7 or 8,8 management most of the time, but I _have_ to believe it's something teams can achieve, even if only briefly. The fact that we don't have an easy label to _talk about_ 9,9 management is a disappointing commentary on our _collective failure to believe in ourselves_. I mean, we can shoot rockets into space and put people on a giant rock orbiting our planet, but build a company where people trust and respect each other while achieving their goals? _That's too far!_ When the U.S. Hockey Team beat the Soviets in 1980, that was a 9,9 organization. I've never worked in a Michelin three-star restaurant's kitchen, but I _have to believe_ many teams trust and respect each other while putting out a terrific product. Regardless of whether you believe a team can embody 9,9 management, I'm confident it's at least something to aspire to in our behavior. Next time you're thinking of rolling your eyes in a meeting (total 3,3, behavior, sheesh) or dropping a Slack bomb on your direct report for not sending you a status update on that project, ask yourself, "What would the 9,9 management version of this look like?" ## Reads & Resources ### Articles [How to Hire the Best People You've Ever Worked With](http://web.archive.org/web/20080229065247/http://blog.pmarca.com/2007/06/how_to_hire_the.html) An old gem from the archives of Marc Andreessen's blog, this is the most concise and helpful piece on how to hire great people I've ever found. Marc splits the article into criteria and process. His criteria? Threefold: drive, curiosity, and ethics. Driven people are self-motivated, curious people who love their field and have informed opinions on the choices you'll need them to make. My favorite quote? "Priests, rabbis, and ministers should give people a second chance on ethics, not hiring managers at startups." ### From [Twitter](https://x.com/andysparks) [Jaleh Rezaei on Establishing an Operating Rhythm for Remote](https://twitter.com/jalehr/status/1574738177985695745?s=20&t=2ijQPrekpcGYYrdrrFRcVg) Jaleh does a fantastic job combining well-organized thoughts with graphics that make her ideas easy to digest in this thread on building an engaged team and successful company while remote. She starts with a bold statement about how she used to think the in-person was The Way but is now "100% remote and can't imagine ever going back." Her big insight I love is that "office culture has a daily rhythm," and remote companies need to design a daily rhythm to replace that's as good if not better than the one we get in an office. ### Audio [Andy Rachleff on "How to Know if You've Got Product-Market Fit"](https://greatness.floodgate.com/episodes/andy-rachleff-on-how-to-know-if-youve-got-product-market-fit-XxGvX8DH/transcript) Did you know Andy coined the term "Product-Market Fit," (aka "PMF"), but he attributes the idea to Don Valentine? In the podcast with Mike Maples at Floodgate, Andy shares two _tangible_ heuristics for knowing if you have PMF for consumer companies _and_ two for enterprise businesses. My favorite part is a story about how "Every great marketer I know is a revisionist," where Andy shares how Google had a _hard time_ selling ads initially. ### Books ![Learning in Relationship](/images/essays/learning-in-relationship.png) [Learning in Relationship](https://www.amazon.com/Learning-Relationship-Foundation-Personal-Professional/dp/1887259015) When I studied at The Hudson Institute for Coaching, this was one of the most helpful (and short) books I read. Ron Short structures the book around three levels of inquiry to learn what's working and what's not in a relationship: systems inquiry, mutual inquiry, and self-inquiry. ## Dice Roll [Yo-Yo Ma Plays Ennio Morricone](https://open.spotify.com/album/1ZReq7RYxh0d0IqLONfBHk?si=CKdpBZX1TLKNE2sHcK0Mxw) Hat tip to my old friend [Kevin Morrill](https://twitter.com/MisterMorrill) for introducing me to this album many years ago. For those unfamiliar, the late Ennio Morricone was an Italian composer most famous for composing soundtracks for movies like The Good, The Bad, and The Ugly. This album features Yo-Yo Ma, the world-class cellist playing some of Morricone's most famous works. This is my go-to album when I need something relaxing to read or write. --- ### Great Managers Manage Themselves First *Published: 2022-09-18* # Great Managers Manage Themselves First The etymology of "manager" traces back to early modern French *manege*, meaning to handle or train a horse. While amusing, this linguistic origin reveals an outdated paradigm: that management inherently involves controlling subordinates rather than developing mutual respect. Dee Hock, Visa's founder, challenged conventional management wisdom by asking leaders about their primary responsibility. Most answered with downward-focused perspectives, which Hock considered fundamentally flawed. He advocated that managers should dedicate approximately **half their time to self-management**, including integrity, character, ethics, and temperament. Remarkably, Hock believed exceptional managers spend only 5% of their time directly managing subordinates. ## Self-Observation in Six Steps The framework draws from Martin Heidegger's concepts of *transparency* (habitual autopilot behavior) and *breakdowns* (unexpected disruptions). The process involves: 1. **Notice breakdowns** when expectations shatter 2. **Identify emotional response** (pleasant, neutral, or unpleasant) 3. **Recognize interpretations** and stories created about events 4. **Acknowledge emotional reactions** to those narratives 5. **Choose conscious actions** rather than habitual responses 6. **Observe behavioral impact** on yourself and others The six-step model demonstrates how extended chains of perception, emotion, and behavior create consequences. Self-awareness enables leaders to interrupt destructive patterns before they damage relationships or outcomes. ## Reads & Resources **Articles:** - [*What I Learned About People Who Scale*](https://building.brex.com/what-i-learned-about-people-that-scale-1c1901d48a41) - Pedro Franceschi discusses how high-growth environments demand constant personal evolution alongside organizational change. **Audio:** - [*Lex Fridman #294 - Tony Fadell*](https://lexfridman.com/tony-fadell/) - Explores product management philosophy and the collective responsibility for understanding customer value before development begins. **Books:** ![The Art of Possibility](/images/essays/art-of-possibility.png) - [*The Art of Possibility*](https://www.amazon.com/The-Art-of-Possibility-audiobook/dp/B004HY9254/) - Co-authored by Rosamund Stone Zander and Benjamin Zander, featuring practical approaches to bold thinking. - [*Wake Up to Your Life*](https://www.amazon.com/Wake-Your-Life-Discovering-Attention/dp/0062516817) - Ken McLeod's framework on self-observation **Resources:** - [*Practical Typography*](https://practicaltypography.com/) - Matthew Butterick's guide to typography fundamentals for designers and founders --- ### A Model for Cutting Down on Gossip and Drama at Work *Published: 2022-09-04* # A Model for Cutting Down on Gossip and Drama at Work Andy Sparks explores the Drama Triangle, a psychological framework developed by Dr. Stephen Karpman in 1972 that explains how interpersonal conflicts emerge when people unconsciously adopt one of three dramatic roles: Victim, Rescuer, or Prosecutor. ## The Drama Triangle Framework ### The Three Roles **Rescuers** focus on fixing others' problems while avoiding their own unpleasant feelings. Sparks notes that founders frequently adopt this role, though their "help" often backfires through micromanagement. **Prosecutors** assign blame and find fault in others, motivated by feelings of superiority or diverting attention from their own shortcomings. **Victims** complain and feel disempowered, acting as though something was done *to* them rather than taking responsibility. ### Key Insight These roles are situational and fluid. People shift between them depending on context rather than being fixed in one role permanently. ## Real-World Examples - A CEO acts as Prosecutor toward engineers, then switches to Rescuer by completing work independently - Managers claim "nobody wants to work anymore" (Victim mentality) - Sales blames Marketing for poor leads while Marketing blames Sales for weak conversion (mutual Prosecution) ## Moving Beyond Drama The solution involves recognizing these patterns and shifting toward alternative behaviors: coaching instead of rescuing, challenging instead of prosecuting, and creating solutions rather than playing victim. David Emerald's *The Power of TED* offers this alternative framework for healthier workplace dynamics. --- ### The Stories in Our Heads (Fact vs. Meaning) *Published: 2022-08-21* # The Stories in Our Heads (Fact vs. Meaning) Andy Sparks explores how we construct narratives around observed events, distinguishing between facts and the meanings we assign to them. ## The Mountain Climbing Metaphor Sparks uses the comparison of a startup CEO to a mountain expedition guide. Both provide maps or visions that outline objectives, milestones, and anticipated obstacles. However, neither the literal map nor the business plan survives contact with reality unchanged. Teams must adapt through both top-down vision and bottom-up adjustment when unforeseen circumstances arise. ## Core Concept: Facts vs. Meaning The central thesis distinguishes between two categories: **Facts** are observable events everyone can verify. Sparks illustrates this with a water balloon example: the fact is that someone got hit; the meaning depends on interpretation. **Meanings** are interpretations we create about facts, especially when information is missing. "People are especially prone to making up stories when there are missing facts." ### Three Practical Steps When recognizing you're operating in "Meaning Land": 1. Create a T-Chart separating facts from meanings 2. Identify what information could clarify the situation 3. Reflect on relationship dynamics that influenced your interpretation ## Reads & Resources **Articles** - [Michael Dearing's Heavybit talk on pricing strategy](https://www.heavybit.com/library/video/harrison-metals-michael-dearing-on-pricing/) **Twitter** - Paul Graham on hiring only when lack of that person limits growth **Audio** - "The Unicorn Launcher #3" podcast featuring accountability and transparency in coaching **Books** ![Inspired by Marty Cagan](/images/essays/inspired.png) - [*Inspired: How to Create Tech Products Customers Love*](https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507) by Marty Cagan **Dice Roll** - Dee Hock's management time allocation framework (5% subordinates, 20% peers, 25% up, 50% self) --- ### Does Your Calendar Reflect Your Priorities? *Published: 2022-08-07* # Does Your Calendar Reflect Your Priorities? This week Andy Sparks caught up with Paul Millerd, author of *The Pathless Path* and *Boundless*, to discuss "infovores," people who have an insatiable appetite for reading and learning. Sparks identifies as an infovore himself, regularly pulling books from shelves during calls and clearing desk piles weekly. For founders scaling businesses, the challenge becomes different: there's too much to learn and not enough time. Rather than trying to consume everything personally, successful founders should leverage others' learning through coaches, newsletters, curated Twitter feeds, and peer CEO groups. ## The Core Principle: Your Calendar Should Reflect Your Priorities Years ago, Keith Rabois shared a principle that stuck with Sparks: **your calendar should reflect your priorities**. Most founder frustrations, slow hiring, misaligned team initiatives, stem from misaligned time management rather than strategy issues. ## Theory vs. Practice **Theory:** When founders struggle, Sparks asks them to identify their top three business priorities for the next 3-6 months. Their calendars typically reveal the disconnect: hiring might be listed as priority one but only receives minimal calendar time. **Practice:** The application requires four steps: 1. Identify your top three priorities and allocate rough percentages (e.g., 30% for hiring) 2. Block meaningful time chunks for each priority 3. Defend your calendar against distractions and meeting requests unaligned with priorities 4. Audit weekly: track whether your actual time matches your stated allocation "If your calendar regularly reflects your priorities (and *the right priorities*), you'll be happy with the results." ## Reads & Resources **Articles** - *"Standups Won't Save You"* by Andy Johns offers alternatives to standard standups, focusing on action items and decisions **From Twitter** - Progress is non-linear; accepting ups and downs helps you ride momentum rather than fight it **Audio** - Seth Godin discusses finding your "smallest viable audience" when launching a business **Books** - [*On Being Nice*](https://www.theschooloflife.com/shop/tsol-press-on-being-nice/) from The School of Life explores balancing kindness with candor, offering: "A fundamental path to remaining calm and kind around people...is distinguishing between what someone does and what they meant to do" **Research** - Ethan Mollick's research shows meetings starting late are less productive and creative --- ### On New Chapters (and My New Chapter) *Published: 2022-07-24* # On New Chapters (and My New Chapter) Andy Sparks announces the launch of **Hoo Boy**, a new newsletter focused on business building and workplace culture. The publication replaces previous iterations called "Andy's Newsletter" and "Coach Class." ## About Hoo Boy The newsletter targets "people who are building a company and care deeply about making that company a place people love to work at." It covers insights and resources for entrepreneurs of all scales, from solo operators to large organizations. Publishing twice monthly, the name reflects Sparks' personal exclamation when stepping back from his desk at day's end. Sparks emphasizes his commitment stems from extensive preparation: two months of reflection before public announcement, alignment work on his broader mission, and a one-year publishing guarantee. ## The Cycle of Renewal This week's featured concept comes from Frederic Hudson's [*The Adult Years*](https://www.amazon.com/Adult-Years-Mastering-Art-Self-Renewal/dp/0787948012) (1991). The framework contrasts linear life progression (school, career, marriage, retirement) with cyclical patterns of renewal. **Four Stages:** 1. **"Go for it"** - Initial excitement with new endeavors 2. **"The doldrums"** - Stagnation requiring decision-making 3. **"Cocooning"** - Reflective transition period for major changes 4. **"Getting ready"** - Exploration and experimentation phase "People _hate_ being here, because they're in-between an end and a beginning. Most people rush through it and that's why they end up with a less-than-ideal new thing." ## Reads & Resources **Articles:** Regina Gerbeaux's Notion document on [running efficient meetings](https://chiefs-of-staff.notion.site/Run-efficient-meetings-that-don-t-suck-68e6580f20ff42de8a2d8974679ead7c) **Twitter:** [Brad Stulberg's thread on peak performance habits](https://twitter.com/BStulberg/status/1545765424289169409), emphasizing "Do the Work before Talking About the Work" **Audio:** [Huberman Lab episode on workspace optimization for productivity](https://podcastnotes.org/huberman-lab/episode-57-optimizing-workspace-for-productivity-focus-creativity-huberman-lab/) **Books:** ![Therapy Journal](/images/essays/therapy-journal.png) [*Therapy Journal*](https://shop.therapynotebooks.com/products/therapy-journal) for founders processing organizational dynamics **Report:** [Carta's H1 2022 State of Startup Compensation Report](https://carta.com/blog/compensation-report-h1-2022/) covering hiring data and salary trends --- ### Captain's Log: May, 2022 *Published: 2022-05-31* My last letter was in October of 2021. Since then, I've written and re-written this letter at least three times. Maybe I should just send the damn thing when I do that. But I don't want this newsletter to be a content factory. With all the weekly, daily, and monthly newsletters, I like that this is a place I can push send "when it feels right." Before I get to what's been going on in my life, I want to share a bit about the above quote from Dean Keith Simonton's *Greatness*. Since leaving Holloway, I've made a few commitments a bit too soon. I committed to writing an newsletter with Jerry Colonna (which we stopped after only a few editions), I committed to starting a podcast about relationships between leaders and their teams (which I stopped before I ever recorded a single episode), and I've tried--twice since October--to start up a weekly newsletter for clients and other CEOs. These things haven't stuck. So what's with that? It would be easy to see this and call it "shiny object syndrome." But the truth of the experience for me is that they've been only partially thought out attempts to solve for a set of things I want but haven't had words for. I want to create (write, podcast, etc.), but for some reason I wasn't motivated by the things I chose to write about or talk about. So a few weeks ago, I noticed I was procrastinating on all the things. So I stopped and decided to spend the remainder of the quarter getting to the bottom of my motivation stall (instead of doing all the things I had planned out). It's almost the inverse of what Simonton and Skinner were referring to. Instead of dropping everything because of something I was interested in, I dropped everything because I noticed I was blocked. And after two weeks, I'm the most unblocked I've been in two years. Everything fits into a cohesive picture. But I know I've been psyched about projects before and soured on them after a bit. So instead of rushing off to make an announcement, I'm going to sit on it through June and make sure the projects have staying power. ## Major Events **Back Pain**: My decision to sit on my ideas for a month and a half turned out to be a fortunate one in an unfortunate way. I've been struggling with lower back pain on-and-off for six years. Until 2021, I only had one incident that was bad enough to take me out of action. But since 2021, I've had at least three weeks where I've been unable to do anything other than lay on my back. For all but the most recent, I could point to a thing I did. "Oh, I lifted those boards wrong, I'll just stop lifting boards and be more careful lifting things." But two weeks ago, I was on my ass after... walking a lot one day. So, other than my regular coaching schedule, my full-time job is now recovering my mobility and getting rid of this pain. In a lot of ways, I think this is a real opportunity. It's obviously a bummer to be in so much pain, but it's a wake-up call that I'm not invincible. I'm glad I'm going through this now, as it's definitely a catalyst to get my butt to stop ignoring acute pain, get to physical therapy, change my diet, and get into great shape again. **We Live in San Francisco Now (again)**: It was only in May of 2021 that Kate and I moved to Denver. But in December of 2021, Andreessen Horowitz offered Kate a job on their biotech team. She loved the team, loved the shape of the job. And to be honest, we never fell in love with Denver. So, we moved back to San Francisco in January. And I have to eat crow here. After 8 years in San Francisco, I left with a bad taste in my mouth and I took the city for granted. Coming back, I see everything in a new light. The year-round flowers, the never-too-hot and never-too-cold is pretty damned nice. And the food. Every city has its issues, but San Francisco is a beautiful place full of wonderful people. ## Projects **Letters to Captain's Log**: You may have noticed the newsletter changed names (again). I'm sorry for all the back-and-forth, and I can imagine it feels uncomfortable with all the jostling. I imagine my readers saying, "Lawd, this guy sure is flaky about his naming." But once I get past the self-criticism, I can see that I didn't have a great name and "Letters" was always a placeholder until I came up with something that fit. Captain's Log feels right for public updates on my life, projects, and more. **Brand New Website**: With all my newfound clarity, I just shipped a total refresh of my personal website. If all the fun new stuff I'm cooking up passes the test of time (am I still pumped about it in six weeks?), then I'll be updating it even further soon. ## Top 5 Recommendations 1. **[Greatness](https://sptr.eomail4.com/f/a/iqbFwK7E8m0fh9yVM-j3yg~~/AAAHUQA~/RgRkeelVP0UgOWQwZDQ1ZDViNjJmMTg3MDRhOGQ0NzZhNGQ1ZmY0YmZEmmh0dHBzOi8vd3d3LmFtYXpvbi5jb20vR3JlYXRuZXNzLVdoby1NYWtlcy1IaXN0b3J5LVdoeS9kcC8wODk4NjIyMDE4P3V0bV9zb3VyY2U9ZW1haWxvY3RvcHVzJnV0bV9tZWRpdW09ZW1haWwmdXRtX2NhbXBhaWduPSUyMzEwJUUyJTgwJTk0Q2FwdGFpbiUyN3MlMjBMb2dXBXNwY2V1Qgpii1Vkl2LVrcZ9UhRuYXRhbGllQGJhYnlsaXN0LmNvbVgEAAAwFg~~)**: I came across this book in an obscure set of Twitter replies where Marc Andreessen said something along the lines of this being the best thing ever published on the nature of "great" people. I haven't read enough on the subject to say definitively whether it's the best or not, but it is a rigorous summary of such a wide and extensive set of research that I feel like to read this book is to ingest thousands of hours of knowledge in a much smaller timeframe. Greatness addresses questions of upbringing, motivation, hard work, personality, the significance of psychopathology, and more as they relate to how and why geniuses became geniuses. 2. **[The Kool-Aid Factory](https://sptr.eomail4.com/f/a/7h11U61lMOwXn3P03gL9Aw~~/AAAHUQA~/RgRkeelVP0UgN2JlOWZjMjRjNGMyZjU2N2FhN2I3YTEyYjViNTc4N2VEcWh0dHBzOi8va29vbGFpZGZhY3RvcnkuY29tLz91dG1fc291cmNlPWVtYWlsb2N0b3B1cyZ1dG1fbWVkaXVtPWVtYWlsJnV0bV9jYW1wYWlnbj0lMjMxMCVFMiU4MCU5NENhcHRhaW4lMjdzJTIwTG9nVwVzcGNldUIKYotVZJdi1a3GfVIUbmF0YWxpZUBiYWJ5bGlzdC5jb21YBAAAMBY~)**: "A set of zines about the ways organizations coordinate," brought to you by [Brie Wolfson](https://sptr.eomail4.com/f/a/dM_Lwsua7s6ck4_zCtp0iA~~/AAAHUQA~/RgRkeelVP0UgMDhiOGJhZjZlMTc1ZjJkZGU2ODA4NDA0YTgyNGI3NTVEcWh0dHBzOi8vdHdpdHRlci5jb20vemVicmllej91dG1fc291cmNlPWVtYWlsb2N0b3B1cyZ1dG1fbWVkaXVtPWVtYWlsJnV0bV9jYW1wYWlnbj0lMjMxMCVFMiU4MCU5NENhcHRhaW4lMjdzJTIwTG9nVwVzcGNldUIKYotVZJdi1a3GfVIUbmF0YWxpZUBiYWJ5bGlzdC5jb21YBAAAMBY~) (formerly of Stripe Press and Figma). Each "zine" like "[The Constitutional Documents Issue](https://sptr.eomail4.com/f/a/UynXE6Jfgk5efxnA_5921Q~~/AAAHUQA~/RgRkeelVP0UgMDhlMDMzMWIzZTFiZGViNDE2ZDcwZDg3NDA2MTc0ZGZEmmh0dHBzOi8va29vbGFpZGZhY3RvcnkuY29tL3ppbmVzL3RoZS1jb25zdGl0dXRpb25hbC1kb2N1bWVudHMtaXNzdWUvP3V0bV9zb3VyY2U9ZW1haWxvY3RvcHVzJnV0bV9tZWRpdW09ZW1haWwmdXRtX2NhbXBhaWduPSUyMzEwJUUyJTgwJTk0Q2FwdGFpbiUyN3MlMjBMb2dXBXNwY2V1Qgpii1Vkl2LVrcZ9UhRuYXRhbGllQGJhYnlsaXN0LmNvbVgEAAAwFg~~)" is full of context, practical to-dos, and examples. Brie has done a terrific job on creating a beautiful, well-researched, and immediately practical set of resources essential to any founder or startup operator. 3. **[The Mochary Method Curriculum](https://sptr.eomail4.com/f/a/GK7XR06Z9MaU8AwLKM-BXg~~/AAAHUQA~/RgRkeelVP0UgZGQ2M2Y5NWM3MmI4YjZhMWU2YTk0MzlkYzc1ZGJmOGZEqmh0dHBzOi8vZG9jcy5nb29nbGUuY29tL2RvY3VtZW50L2QvMThGaUpiWW41M2ZUdFBtcGhmZENLVDJUTVdILThZMkwtTUxxRGstTUZWNHMvZWRpdD91dG1fc291cmNlPWVtYWlsb2N0b3B1cyZ1dG1fbWVkaXVtPWVtYWlsJnV0bV9jYW1wYWlnbj0lMjMxMCVFMiU4MCU5NENhcHRhaW4lMjdzJTIwTG9nVwVzcGNldUIKYotVZJdi1a3GfVIUbmF0YWxpZUBiYWJ5bGlzdC5jb21YBAAAMBY~)**: Matt Mochary is the CEO coach behind [*The Great CEO Within*](https://sptr.eomail4.com/f/a/MuPnEZeFcVy6eFbz3dUPnw~~/AAAHUQA~/RgRkeelVP0UgOGFkN2Y1MDc2OTZkMTBhMTFmODM0ZDY2ZmE3NjRmMGFEo2h0dHBzOi8vd3d3LmFtYXpvbi5jb20vR3JlYXQtQ0VPLVdpdGhpbi1UYWN0aWNhbC1CdWlsZGluZy1lYm9vay9kcC9CMDdaTEdRWllDP3V0bV9zb3VyY2U9ZW1haWxvY3RvcHVzJnV0bV9tZWRpdW09ZW1haWwmdXRtX2NhbXBhaWduPSUyMzEwJUUyJTgwJTk0Q2FwdGFpbiUyN3MlMjBMb2dXBXNwY2V1Qgpii1Vkl2LVrcZ9UhRuYXRhbGllQGJhYnlsaXN0LmNvbVgEAAAwFg~~), a favorite book amongst most CEOs I know (and coach). Matt has made public an extensive series of tactical Google Docs to help founders build their companies. It's a go-to now for me, as even when I'm working with a CEO through something I know well (like... *onboarding),* I'll check Matt's curriculum to see if there's anything new to learn or recommend. 4. **[A Boring Set of Plastic Bottles](https://sptr.eomail4.com/f/a/iBTxMOx0ilnvEUQp3wOojQ~~/AAAHUQA~/RgRkeelVP0UgOGU5ZTJhODhmNzQyMzU5NDYxOGVjMjZlYzgwM2E5NDVEemh0dHBzOi8vd3d3LmFtYXpvbi5jb20vZHAvQjA3NlBUM0JEOT91dG1fc291cmNlPWVtYWlsb2N0b3B1cyZ1dG1fbWVkaXVtPWVtYWlsJnV0bV9jYW1wYWlnbj0lMjMxMCVFMiU4MCU5NENhcHRhaW4lMjdzJTIwTG9nVwVzcGNldUIKYotVZJdi1a3GfVIUbmF0YWxpZUBiYWJ5bGlzdC5jb21YBAAAMBY~)**: About a year ago, I was at my friend Brett's house. Next to his stove was a set of these OXO plastic squeeze bottles, one labeled "Olive Oil," and the other "Avocado Oil." The tapered nozzle allows for more control over where the oil goes in your pan (instead of just pouring a blob of oil in). If you're a cook, you'll love these (and they're like $11). 5. **[Night Rider Playlist Radio](https://sptr.eomail4.com/f/a/xJrAAF75KYuG_QRVdcrzpA~~/AAAHUQA~/RgRkeelVP0UgMDlmM2E4ZTdhYTM5ZDFjZTAxZWI5ZjAyZjQxZjY5ZTREomh0dHBzOi8vb3Blbi5zcG90aWZ5LmNvbS9wbGF5bGlzdC8zN2k5ZFFaRjFEWDZHSlhpdVpSaXNyP3NpPWE4NTkzOWQ2ODEyZDRhYWMmdXRtX3NvdXJjZT1lbWFpbG9jdG9wdXMmdXRtX21lZGl1bT1lbWFpbCZ1dG1fY2FtcGFpZ249JTIzMTAlRTIlODAlOTRDYXB0YWluJTI3cyUyMExvZ1cFc3BjZXVCCmKLVWSXYtWtxn1SFG5hdGFsaWVAYmFieWxpc3QuY29tWAQAADAW)**: When I need to focus, nothing helps more than upbeat, dark, moody house music. The Night Rider playlist is a public playlist by Spotify, but a few months ago I put the playlist on the "radio" feature in Spotify, and it delivered hit after hit. If you're looking for some new concentration music, give this a shot! Thanks for reading--I'm looking forward to what's next. Andy. --- ### Captain's Log: October 2021 *Published: 2021-10-27* > "One of the most reliable signs that you need a holiday is the conviction that you cannot spare the time to make one." -- Bryan Magee You might be confused. Doesn't this email usually come from MailChimp? Yes, yes, it does. But I was sick of paying $50 / mo. for something I can get for free [here](https://andysparks.substack.com/p/fundraising-ceo-role-evolution). So, from now on, I'll be sending *Letters* out via Substack. Mom & Dad came to Denver to visit Kate and me a few weeks ago. Since I moved out of their house, I've lived in apartments, so it was such a treat to have them over to *our house* for the first time. Dad and I bonded over building a picnic table and grilling steaks. ## Short Updates - **Andy's Newsletter**: What? Isn't this Andy's Newsletter? I know it's confusing, but I'm not perfect. For the last few weeks, I've been sending out a *private* newsletter to my coaching clients with links and resources for startup CEOs and founders looking to both perform at a higher level *and* stay sane while doing so. I'm also doing that on Substack. But while *Letters* will go out ~4-5x / year, I'll send *Andy's Newsletter* about once a week. I'm keeping them separate since this one is way more personal, and I don't want to subject y'all to an email full of startup founder shite if you're not interested in it. Read the first edition and sign up to get it in your inbox if you're interested. - **I'm Writing a Novel**: I've been running an experiment for the last year: limit my coaching work to about 30 hours a week and see what happens with all the spare time. It's been a struggle not to habitually fill it with more "work." But about three weeks ago, I got a migraine. And when I get migraines, I hop in the shower because the hot water helps with the headache. It's such a cliche, but as I stood there for a half-hour with no screen or distraction but running water, I began to get an idea for a novel. I've been working on it since, and I can't wait to share more with you. - **Captain's Log, [Commonplace](https://github.com/AndySparks/captains-log/tree/master/commonplace), and [Readings Lists](https://github.com/AndySparks/captains-log/tree/master/resources/reading-lists)**: For those of you new-ish folks, I keep and continually update a bunch of resources on GitHub. I call it my "Captain's Log." I recently updated my [2021 Commonplace](https://github.com/AndySparks/captains-log/blob/master/commonplace/2021.md) to reflect my year thus far. I've also updated my "[On Writing](https://github.com/AndySparks/captains-log/blob/master/resources/reading-lists/on-writing.md)" reading list with lots of resources I've been using to learn how to write fiction. ## Cool Stuff - **More Housing**: I try to stay away from politics in *Letters.* But the one issue I'll keep beating the drum on is that we *need to build WAY more housing all over the U.S.* [This is a great article on why](https://www.worksinprogress.co/issue/the-housing-theory-of-everything/). One stat to blow your mind: if NYC, San Jose, and San Francisco loosened rules on dense housing, U.S. GDP would be 8.9% higher. Imagine if we did that in cities across the U.S. - **[Bioswales](https://twitter.com/zachklein/status/1451625042270322688?s=20)**: I'd never heard this term before, but thanks to Zach Klein now I know it. Bioswales are a beautiful way to collect rainwater in cities, and I hope they become a major feature of cities going forward. - **Brandon Sanderson Teaches How to Write Science Fiction and Fantasy**: For those of you who don't know Brandon Sanderson, he's one of the greatest living fantasy writers. I've read almost all of his 20+ books and loved every single one of them. And it turns out he teaches a class at BYU on how to write sci-fi and fantasy, and there are recordings of 14+ of his lectures on YouTube for FREE. I love the internet. If you're even *generally* interested in how to tell a great story, I recommend giving these a watch. - **Robert McKee's Books on Screenwriting**: Kate has begun working on a few screenplays. Not only do I think that's *awesome*, it's part of what gave me the courage to start working on a novel. I've also been feeding off of her learning experience, following her reading. If you're interested in writing a novel, screenplay, or again if you're just *generally* interested in learning how to tell a good story, these books are a big recommend from me. There are three: [Story](https://www.amazon.com/Story-Structure-Substance-Principles-Screenwriting-ebook/dp/B0042FZVOY), [Dialogue](https://www.amazon.com/Dialogue-Verbal-Action-Stage-Screen-ebook/dp/B017RQP30Q/ref=tmm_kin_swatch_0?_encoding=UTF8&qid=&sr=), and [Character](https://www.amazon.com/Character-Role-Design-Stage-Screen/dp/1455591955). - **LoFi Fruits Music**: I've been jamming to this LoFi artist when I need something instrumental to help me get my focus on. Hoping you'll dig it as much as I do! ## How You Can Help - No asks this month! If you have a minute to spare, reply to this email with a bit about what you've been up to! Thanks for reading--I'm looking forward to what's next. Andy. --- ### Captain's Log: September 2021 *Published: 2021-09-09* > "Sometimes it takes darkness and the sweet confinement of your aloneness to learn anything or anyone that does not bring you alive is too small for you." -- From "Sweet Darkness," in Essentials by David Whyte (2020) A lot has happened since I sent Edition 7 of letters in April. Most importantly, I'm excited to share about my new climate-focused coaching company, [Blue Dot](https://www.lookbluedot.com/). If you want to learn more, you can read the announcement post [here](https://www.lookbluedot.com/post/world-meet-blue-dot) and I'll leave it at that. But for today's edition of Letters, I wanted to share a bit about the poem I put above the photos. To start, quoting poetry is a new thing to me, and I'm a bit self-conscious of how it's one of those defining behaviors of coaches. It's like the day you become a coach, suddenly poetry becomes a part of your life, and that's always rubbed me the wrong way. But David Whyte is an author I've read a lot of this year, and it turns out he's a poet and his words have brought me to tears a few times. Now on to the point. It's no surprise that David wrote this poem in 2020 when so many of us were feeling so very alone. I know I was. And a big part of that journey for me was seeing how I'd surrounded myself with some things and some people that did not "bring me alive." Coaching--the career I switched into as a result--does bring me alive, and part of what I love is helping clients find the things that bring them alive and bring more of that aliveness to the world. So I guess my message for today is that you deserve to feel big, and I hope one bright part of the mess of the last year can be some perspective that gives you the courage to find the things and people that are the right size (or even big enough to be scary). ## Short Updates **We live in Denver now!** Our movers came on April 29th and were supposed to show up in Denver on June 2nd. They showed up on June 22nd. That was a nice lesson in patience. This is the first time living in my own whole house. We live within walking distance to Rino in Denver, but we have enough peace and quiet to have a fun little backyard. Needless to say, I've been enjoying transforming into a childless semi-suburban Dad. If you know anyone rad in Denver I should meet, please let me know! **Between**: Right after I left Holloway, I declared I was going to start a podcast about relationships between co-founders and leaders. A friend of mine created the artwork for it, I built the website, and I even had guests who were ready to come on the show. But something just didn't feel right about it. And that lack of rightness has led me to decide to pull the plug on Between. In retrospect, I think I rushed my decisions after Holloway out of a need to be "doing something creative" as I sat with the discomfort of being in the middle of a career transition. So, I'm sorry to folks who were looking forward to it, but I learned a valuable lesson about not rushing into announcements about things and how valuable it is to listen to my gut. **Shenpa**: Shenpa is an ineffable (i.e. something that can't easily be put into words) Tibetan concept I discovered in May. If you struggle with anger, imposter syndrome, a noisy inner critic, or any kind of general stress or anxiety, this is genuinely the single most helpful tool I've found for working with that stuff personally AND with my clients. You can read about the idea [here](https://www.lionsroar.com/how-we-get-hooked-shenpa-and-how-we-get-unhooked/), and listen to Tibetan nun Pema Chodron talk about it [here](https://www.amazon.com/Fully-Alive-Retreat-Beautifully-Uncertainty/dp/1611800315) and [here](https://www.amazon.com/Dont-Bite-Hook-Resentment-Destructive/dp/1590304349). **Climate Change**: Okay climate change clearly is not awesome, but learning about it is. One year ago today, San Francisco's entire sky was the same color orange as Blade Runner 2040, and that kicked off a personal awakening and research phase. Climate is an area that can easily devolve into an unhelpful "purity vs. impurity" debate full of shaming and silly crap. A friend put it simply to me last week: "addressing climate change is about how we make the world a safer place for people." If you're interested in learning more about what to do about climate change, check out the following: Susan Su's [Want to Work on Climate? Start Here.](https://susanfsu.medium.com/want-to-work-on-climate-start-here-14afbf3ccd74) and Ryan Orbuch's [Negative Emissions Reading List](https://www.orbuch.com/nets-reading-list/). **The Wheel of Time**: In 2019, I read all 14 books in Robert Jordan's The Wheel of Time series. It was a huge investment in time, and it was worth every minute. I feel like I learned valuable lessons about the internal struggle of leadership (and felt very very seen) by the character development in the series. So what? Well, Amazon is plowing a pile of money into a TV series adaptation, and the trailer just dropped last week here. I am beyond excited for this to begin! **[Attack on Titan](https://en.wikipedia.org/wiki/Attack_on_Titan)**: I've never really gotten into Anime. To be honest, I held a silly immature view for a long time that it was for "those kids." And then I met Kate, who is more into anime than anyone I've ever met. So, we've been watching a lot of it. And I've been loving it. But Attack on Titan (S1 on Netflix, the rest on Hulu) was absolutely awesome. I mean it was so good. Like, I'm not even going to tell you what it's about or anything else. Just watch it. And know that it's weird, but it's so original and I was completely hooked. **How my Coaching Works**: I've been meaning to post an FAQ of sorts explaining how my coaching works for a long time, and I finally got around to it this week. If you're curious, you can read about it [here](/essays/how-my-coaching-works). ## How You Can Help Help spread the word about Blue Dot! You can write your own tweet and link to the announcement here or retweet/quote tweet my tweet here. If you're in a private Slack group with founders or climate folks, I'd also appreciate it if you'd be up for sharing the post there. How was this email? What did you like? What should I keep doing? What should I stop doing? Looking forward to what's next, Andy. --- ### How My Coaching Works *Published: 2021-09-08* > "Life seemed to be an educator's practical joke in which you spend the first half learning and the second half learning that everything you learned in the first half was wrong." > > Russel Baker The field of coaching has a ton of variability. Some folks woke up one day and decided to be a coach, others have a Ph.D. in psychology, others are academics, and so on. So when I meet someone interested in working together, they inevitably have a lot of questions. Below, you'll find a bit of context on me and how I got here followed by a set of the most frequently asked questions and my answers. ## A bit on me I'll start with a bit on my career *before* I became an executive coach to startup founders and follow that with a bit on how I went from entrepreneur to coach. Since 2009, I've started four companies. The first one makes me laugh because it was an elaborate homebrewing operation I started at 19 that has evolved to become known as "the brewery" amongst friends and family. The second was a sort of proto-ProductHunt. The third was Mattermark, a business analytics and database company where we grew from $0 - $5M in ARR in 3.5 years. And the fourth was Holloway, a digital book publishing company. I've been the CEO and the COO. Across my companies, we raised more than $20M in VC money (not necessarily a good thing). And finally, I wrote a book, [*The Holloway Guide to Raising Venture Capital*](https://www.holloway.com/g/venture-capital/about). In 2020, I left Holloway to become a coach. Whenever I asked colleagues what my "superpower" was, they'd say, "listening." I never thought that could be a career, but as I contemplated what to do in the next chapter of my career, friends and colleagues suggested I explore becoming a coach. Since then, I have studied to become a coach at [The Hudson Institute of Coaching](https://hudsoninstitute.com/) through a 9-month training program. Together, my experience as an entrepreneur *and* a coach allows me to both coach and advise. My goal as a coach is to help you become more self-aware and use your agency to contribute to the world in a way that aligns with your values. I believe that if you do that, you have a pretty damn good shot at being a successful entrepreneur. If this and my answers below leave you feeling interested in working together, you can contact me [here](/coaching). ## Who is your ideal client? I love working with early-stage founders whose companies are growing quickly. This doesn't necessarily mean they've taken venture funding, but in many cases, the founders I coach have raised a seed or series A round of funding. I prefer to work with founders once they've found at least *some* product-market fit. Almost all of my clients are CEOs. If you're a non-CEO founder, I will not work with you unless your CEO co-founder is either working with a coach now or has worked with a coach for a significant period of time. I also do not work with co-CEOs or CEO/President or any other co-founder arrangement where there is not a clear CEO. ## How many clients do you work with? My maximum is 15 clients at a time, and most of the time I have about ~10 clients. ## How long does a coaching engagement last? I don't coach with a fixed timeline in mind. I have some clients I've worked with for more than a year and others who I've only worked with for three months. Most clients, however, work with me for 6 months or more. ## How are your engagements structured? I also don't coach with a fixed structure. I recommend thinking of our coaching engagement in three-month sprints where we will meet every other week (~6 sessions). In the first 1-2 sessions, we'll set some goals for what you'd like to get out of our work together and then spend the following 4-5 sessions working on those goals. In a 7th session, we'll do a retrospective, look back on the goals, and see if there's anything you'd like to change about your goals or how we work together. At this point you should be able to unquestionably see progress. ## Do you have a system? I do not have a fixed system. Each founder brings unique challenges, relationships, and history and I adapt how I work to each client. In my work, I draw upon research and frameworks on how people change, transitions, interpersonal relationships, conflict management, recruiting, management, and much much more. One good metaphor for how to think about our work together is that coaching is a bit like Google Maps. Huh? Like in Google Maps, you have to understand where you are, where your blue dot is, how you got there, what you like about it and what you don't. Then, you have to pick a destination. Once we're clear on the here and the there, we can begin to work on picking a route. This metaphor applies to three-month sprints and inside of individual sessions. If you're looking for a system for how to become a great CEO, read Matt Mochary's [*The Great CEO Within*](https://docs.google.com/document/d/1ZJZbv4J6FZ8Dnb0JuMhJxTnwl-dwqx5xl0s65DE3wO8/preview). ## How do we begin? If both of us feel like there's a great fit, a few things will happen: 1. I'll send a contract that includes a confidentiality clause. 2. I'll send an intake form. Expect to spend 30-60 minutes on this. 3. We'll schedule our first session. ## What's an intake form? The intake form serves a dual purpose. First, it helps me get to know you better and learn more about what you want to get out of coaching. Second, it helps you learn more about yourself. **The key is to not rush this**. Plan on setting aside *at least* an hour to think through your responses. The kind of things you can expect to reflect on are what's going well, what's not going well, your values, strengths, areas for growth, and your family and work history. Once you complete this form, you'll be able to review your answers in Notion. We'll also review this periodically to make sure you're growing. ## How often do we meet? I meet with most of my clients every other week. Some clients, when going through particularly turbulent moments will meet more often, but it's totally up to you. You can text or email me anytime as well, and I try to respond within 24 hours. ## Where do we meet? Right now, due to the pandemic, all of my sessions are virtual. I prefer Zoom or some other format that includes video, as it allows me to pick up on non-verbal cues much better. I'm happy to also hold our sessions over the phone if you have a strong preference to do so. I do ask that you don't spend *the majority* of your sessions walking. Call quality tends to be poor and I find that clients are less focused on our work together. If you need to take a walk every once in a while, that's fine, but please don't make it the majority of our sessions. On the same thread, I ask that clients find a relaxing, private, quiet space with reliable internet for our sessions so we can focus on the work instead of a noisy environment or anything like that. ## How long is a session? Most sessions last 60 minutes. If we're consistently hitting the 55-minute mark and feeling like there is more work to be done, we may extend it to 90 minutes or more. ## When are you available for coaching? I coach Monday - Thursday from 10 am - 4 pm PT. I've found I feel burnt out if I do more than three sessions a day, so that limits how many I can do. Under special circumstances (e.g. a layoff or something like that), I can meet outside my regular hours. ## How do we schedule our sessions? I prefer to book each client in a recurring (every other week) slot. Once we begin, I'll introduce you to my assistant, who will coordinate if you need to change your slot or make changes. Most of the time, I'm flexible if you need to move a session around, but if it becomes a regular habit you can expect us to discuss it. ## How does a typical session work? Most sessions follow the following structure: 1. **The Update:** Usually there's some progress since the last session that's worth sharing. It can include anything you've learned, any changes in priorities or goals, new challenges, or anything like that. 2. **The Work:** Pretty soon, you'll begin to hear my voice asking, "What would you like to get out of today's session?" After the update, in every session, we'll declare a clear intention for what you'd like to work on. Sometimes this may be exploring a feeling of discomfort and other times you may want to walk away with concrete steps, but it's up to you. 3. **The Wrap Up:** When about 5 minutes are remaining, I'll ask you some form of a question to help you synthesize your insights from our session and come up with a concrete way to apply what you've learned. We'll also periodically set aside time for you to give me feedback at the end of a session. ## How should I prepare for a session? I notice a meaningful difference between the clients who prepare for a session vs. those who show up having just dropped off of another call. I recommend blocking off 15 minutes before each session to reflect on what's worth updating me on and to pick 1-3 items you'd like to dig into in our sessions. Ask yourself, "What do I want to walk away with at the end of my session with Andy?" That will help focus the work we do together. ## How long does it take to see results? You should see noticeable growth within the first 1-3 months. Most clients walk away from the first couple of sessions with an intuitive sense of something "working." At the bare minimum, when we do our first retrospective after 3 months, you should see clear results on your personal work and on your business results. ## How can I provide feedback? I love feedback. If you have something you'd like to discuss, there are several great outlets for it. First, at the beginning of a session, you can ask to set aside 5-10 minutes for feedback. Second, we'll regularly look back on our relationship every three months. Third, you can always send me thoughts and feedback in writing via email. Fourth, if it's something big you can always ask me to hop on the phone to talk something over. ## How much do you charge? I work on a sliding scale based on a number of factors including stage, revenue, and company size starting at $1,250/mo. and moving up toward $5,000/mo. I don't do per session fees. For the monthly fee, we'll meet every other week (some months that's 2 sessions; others it's 3). If you're really excited about working together and money is getting in the way of working together, let's talk about it because I can usually work something out for a great fit. I don't do multi-month contracts or anything like that, as I feel you should be able to opt out at any time. --- ### Captain's Log: April 2021 *Published: 2021-04-14* > "The muse may have more than one job for us over our lifetime." > > Steven Pressfield, *The War of Art*, (p. 95) Last week, we announced that paperback and hardcover copies of my book, *The Holloway Guide to Raising Venture Capital*, are available on [Amazon](https://www.amazon.com/Holloway-Guide-Raising-Venture-Capital/dp/1952120098/). It was an exciting day for all the obvious reasons. Holding a physical copy of something I worked on for years, the thing *looks* and *feels* beautiful, and the beaming pride from Mom and Dad didn't hurt. But it was also a strange, confusing day. We set out to write this book for two reasons: 1. We were starting a book publishing company, and we wanted to learn what it took to write, edit, and publish a book. 2. We felt like all the other "how to raise VC" books were written by VCs, and I wanted to take everything I learned outside of books and put it in a book. I think we accomplished both of those goals. But we published the digital version almost a year and a half ago. And since then, I've kind of ... moved on. I'm no longer the CEO at Holloway. On top of that, through *writing* the book, I came to the conclusion that *the allure of venture capital and all the trimmings of "startups,"* lure (intentionally or unintentionally, it's probably a mix) bright-eyed founders into a model for business building that puts people on a treadmill toward unlikely success. When people ask me today how to raise venture capital, I respond, "Are you sure you need to?" In the end, yesterday was strange because I can't shake the feeling that *I wrote a book on something I'm not that interested in being an expert on anymore*. What a sales pitch, right? I'm still very proud of the book. Thanks to [Rachel Jepsen's](https://twitter.com/DidYouWriteThat) nudging, we addressed the issue of whether to raise venture capital or not in a chapter of the book. I think the book will continue to be very helpful to a ton of entrepreneurs. ## Short Update - **Moving to Denver**: On April 29th, movers will come and pack Kate and I up. We're moving to Denver. It's a fun homecoming of sorts. I was born in Denver and lived there until I was eleven. My family has moved on, but I'm excited to begin a new chapter with Kate there. If you know good people, good restaurants, bars, things to do, please reply and share! - **Leaving San Francisco**: Leaving during a pandemic is strange. If you know me well, you know that I love to throw a good party. Over the years in San Francisco, I've hosted Ocean Beach bonfires that got so big the police had to break them up, monthly backyard BBQs with the Rahmans, and many glorious days in Dolores Park. But this year: no parties. I feel a bit like I'm sneaking out the back door. My best friends know I'm leaving, but I haven't been able to bear telling the owners of my local pub, Shotwell's. For some reason, I don't want to admit I'm leaving. - **David Whyte**: Thanks to [Jonny Miller](https://twitter.com/jonnym1ller), I found myself 20 minutes before a coaching session with a client crying in my office listening to [David Whyte talking with Sam Harris about friendship](https://dynamic.wakingup.com/course/C1134C). I chalk it up to leaving San Francisco and reflecting on the amazing friendships I've gained and maintained here, particularly Samiur Rahman and the wonderful Carrie Phillips (who moved here with me almost nine years ago to start a company!). After that, I finally finished [Crossing the Unknown Sea: Work as a Pilgrimage of Identity](https://www.amazon.com/Crossing-Sea-Work-Pilgrimage-Identity/dp/1573229148), in which my favorite line was something along the lines of *"Don't fuck with the poet!"* You can be sure I'll be reading more David Whyte in the coming months. - **Between**: For the new folks, Between is a podcast I'm working on where I'll be interviewing people about the relationships behind companies and products we love. The wonderful Hamish Smyth recently shared his first cut at the art direction (see [here](https://drive.google.com/file/d/180V-iBX4BMKU4cPY4-jxfzgQkfeOCsIY/view)), and I'm working on a "trailer" of sorts (see [here](https://drive.google.com/file/d/1K80jnUWxRTUYzD8zQYkC6fryErqSewcQ/view)). I'm hoping to have first episodes out this summer. - **Reading**: You can always follow along with my reading [here](https://github.com/AndySparks/captains-log/blob/master/commonplace/2021.md) (under the books heading). This year, my reading skews heavily toward books on coaching, as I train as a coach. But these books are fascinating, and every time I open one of these books I know I'm going to be a different person at the end. I now read for about 1-2 hours every morning, and the feeling of being a student *because I want to be* not because *I'm supposed to be* is extraordinarily liberating. - **Ask Jerry**: A month or two ago, I decided to move on from writing Ask Jerry. After some reflection, I realized I wasn't really *writing* as much as I was editing Jerry. And that's not what I wanted to do. I also had to reflect on my own desire to be associated with someone I admired as I made a career switch. I'm glad I worked on it while I did, but some things just need to be experiments. - **Editing**: [Rachel Jepsen](https://twitter.com/DidYouWriteThat) edits almost everything I write. Except she didn't edit this. Because she's working on editing a big piece on coaching I'm working on, and I wanted to get this sucker out there. So if there are typos, it's on me. ## How You Can Help - If you or anyone you know are interested in working with me as a coach. Reply to this email and let me know so we can set up some time! - Buy a copy of my book [here](https://www.amazon.com/Holloway-Guide-Raising-Venture-Capital/dp/1952120098/)! - How was this email? What did you like? What should I keep doing? What should I stop doing? Looking forward to what's next, Andy. --- ### Captain's Log: December 2020 *Published: 2020-12-28* > "The hardest thing to attend to is that which is closest to ourselves, that which is most constant and familiar. And this closest something is, ourselves, our own habits and ways of doing things." > > John Dewey Each of us needs our own village of people, and 2020 has made that particularly hard. Even before COVID, I would often cite a quote from Kurt Vonnegut: *"You are not enough people!"* For the last six weeks, Kate and I have been staying with Danielle and Kevin Morrill at their house in Denver. It's been refreshing to have someone other than Kate to talk to on a regular basis. COVID has left us putting an awful lot of pressure on our significant others. But we couldn't shake the desire to be home, to have a quiet breakfast in our sun-filled breakfast nook, and ironically ready to have fewer people. When I wrote the first edition of Letters nearly a year ago, I wanted to use the format to build new friendships and help water relationships I'd neglected. I wanted to find more people. I modeled my newsletter after Tobias Van Schneider's newsletter, which is a blend of personal and professional. Now, more than 2,000 people are subscribed and I'm not really sure what for. It feels self-indulgent to write to 2,000 people just telling them what I've been up to and what I've been thinking about. But this self-indulgence has led to beautiful new friendships, coaching clients, and encouraging responses that I'm plain addicted to now. So I guess I'll keep doing this for a while. As I sat down to write, wiggling my fingers to loosen 'em up, I realized the last six weeks have been some of the most exciting and productive of my life. Not only have I made a lot of progress, I've learned enough to transform my thinking on more than one subject. ## Short Updates - **Coaching**: Over the last six weeks, I went from having ~8 coaching clients to having 17. I'm almost at my max. A huge thank you goes out to [Kevin Lee](https://twitter.com/kevinleeme), who graciously referred a boatload of people to me after his [thread](https://twitter.com/kevinleeme/status/1317519904468201472?s=12) on the value of coaching. I did not expect to grow this brand new business so quickly. It's incredibly cool that learning to be a coach teaches you so much about yourself, and it's useful at home, too. The school I'm starting in January, [The Hudson Institute](https://hudsoninstitute.com/), has a saying (even the title of a book), [Self as Coach, Self as Leader](https://bookshop.org/books/self-as-coach-self-as-leader-developing-the-best-in-you-to-develop-the-best-in-others/9781119562559). It starts with you. How you show up. And every time I open a coaching book or start a session, I now know I'm about to learn something about myself. I feel like I've gotten 5 years of personal reflection and growth packed into three months. - **Incorporating**: I incorporated an LLC to handle the business, Sparks Industries, LLC (hat tip to Marvel there). I'm grateful I was able to use my experience as a COO & CEO to get things spun up, otherwise this would have been daunting. - **Wealth (for the romantics)**: Over the last 10 years, I've lived in San Francisco. As a startup founder, I went through periods where I earned a more than healthy salary, and other periods where I had no income for entire quarters at a time. I didn't save much money, and I'm conflicted on how to feel about that. On the one hand, I wish I had a nest egg to go buy a house and begin, well, nesting. On the other hand, in my twenties I used this Robert Greene quote as my own personal mantra: "All that should concern you in the early stages of your career is acquiring practical knowledge in the most efficient manner possible." I focused on new skills, knowledge, deepening friendships and building new ones with creators I respected. In those domains, the domains of knowledge and relationships, I feel wealthy. - **Wealth (for the econ-geeks)**: I've been reflecting on how compounding applies to other forms of capital beyond financial capital (as in a 401k). Social capital is "the durable network of social and professional relationships through which founders can identify and access resources" (Wasserman, loc. 770) and "human capital is human capability based on knowledge, education, training, skills, habits, etc." (Goodwin, 2003). While I haven't saved much money to compound, transitioning to a career as a coach has shown me that I've certainly compounded social and human capital. - **Independence**: Depending if you count the "brewery" from college, this is my fourth or fifth company I've started. But this one is different: no partners, just me. This is a deliberate experiment to own all the success (and the failures). So far, I'm enjoying the freedom to set my own schedule and do things "my way." - **Studying**: There's an ancient Chinese expression, "Theory without practice is foolish; practice without theory is dangerous." While I'm doing about ~20 hours of coaching per week now, I'm churning through the curriculum books for Hudson and others that pique my interest like main and side quests in an RPG. At past companies, I would read a book on marketing here, a book on CEO-ing there, but studying was never as formal of a part of my work as it is now. Reading felt like it was something I'd do "when the real work was done," but I have a strong hunch that was pretty backwards. - **Rhythm vs. Schedule**: In November, I completed a prerequisite for my coaching certification program with The Hudson Institute called "LifeForward." It's a program to help expose aspiring coaches to their method in practice, but it's also like getting a concentrated shot of coaching in 5 days. One coach, Deb, introduced me to the idea of a rhythm vs. a schedule. As a CEO, my days were scheduled to the minute. As I began coaching, I fell into that old habit. But Deb helped me realize the need for rhythm, which includes the flexibility of jazz. So I blocked off Wednesdays for "play days," where I wake up and decide what I want to do without anything scheduled. - **Resentment & Anxiety**: As I've been studying coaching methodologies, I've been learning about "moods" or "prolonged emotional states." I've learned that I've routinely found myself in two ugly and unproductive moods: resentment and anxiety. The first has to do with not accepting facts, things that have already happened. The second has to do with not accepting uncertainty. Once I realized I was thrashing around fighting things entirely out of my control, I was able to find a well of peace. - **Updating My Captain's Log**: In 2017, I began recording various things in GitHub in what I call my "Captain's Log." I keep public [reading lists](https://github.com/AndySparks/captains-log/tree/master/resources/reading-lists) and annual [commonplace](https://github.com/AndySparks/captains-log/blob/master/commonplace/wtf-is-a-commonplace.md) logs. I just updated 2020 in case you're interested in browsing. - **Annual Review**: I've done an annual review for four out of the last five years. I skipped last year and wish I hadn't. This year, I'm drawing inspiration from Jonny Miller's [Reflecting Forwards](https://reflectingforwards.com/) (paying for his template goes toward supporting his wedding, Jonny is a delightful person, btw) and Steve Schlafman's [The Ultimate Annual Review](https://www.annualreview.life/) (Steve is also a delight, and a fellow traveler on the coach path). ![Before the move](/images/essays/life-update-dec-2020-before.png) ![Screenshot of morning pages](/images/essays/life-update-dec-2020-screenshot.png) - **Upgrading My Camera Setup**: As a coach, I'm now spending a lot of time on Zoom calls. Each session is deeply personal, but I felt like my camera left a lot to be desired in terms of creating an experience closer to sitting in a room together. Each session is "the product," and I wanted to make sure clients got the best experience possible. So I invested in a new DSLR camera, and it makes a big difference. I created a post with my equipment [here.](/essays/using-a-dslr-as-a-webcam-for-zoom-calls) ## Ask Jerry In the last edition (October 28th), I announced Ask Jerry and shared a few excerpts of the first edition. We've now published four editions: - [Jerry Colonna on Co-Founder Resentment](https://askjerry.substack.com/p/jerry-colonna-on-co-founder-resentment) - [Jerry Colonna on Exploring Purpose and Motivation](https://askjerry.substack.com/p/jerry-colonna-on-exploring-purpose) - [Why Ask Jerry](https://askjerry.substack.com/p/why-ask-jerry) - [Follow Your Curiosity. Read Your Ass Off.](https://askjerry.substack.com/p/follow-your-curiosity-read-your-ass) After edition three, we decided we needed to let the "Jerry Colonna on" headline format die and write better headlines. This paid off big time, with Edition four getting 12K reads vs. the next highest clocking in at 2.1K. Total subscribers are a little over 3K after 6 weeks, which speaks to the power of the bundle the team at [Everything](https://everything.substack.com/) is putting together. For reference, it took almost a year for Holloway's Good Work to reach ~5K subscribers. ## What I've Been Reading *Fiction* - [*Rhythm of War*](https://www.amazon.com/Rhythm-Stormlight-Archive-Brandon-Sanderson/dp/0765326388) (Brandon Sanderson): I was giddy when the fourth installment of Sanderson's fantasy epic-novel series, The Stormlight Archive, came out this November. I've been waiting for this one for more than a year. *Non-Fiction* - *[Coaching to the Human Soul: Ontological Coaching and Deep Change](http://www.newfieldinstitute.com.au/html/books_chsI.html), Volumes I and II* (Alan Sieler): Recommended to me by Reboot co-founder Khalid Halim, this series emphasizes three domains necessary for a coach to facilitate deep change: language, emotions, and physiology. One quote stuck out to me: > "Anxiety is evident in excessive time spent on tasks, micromanagement, short-term focus." ## What I've Been Listening To - Podcast: [Lisa Feldman Barrett: Balancing the Brain Budget [The Knowledge Project Ep. #92]](https://fs.blog/knowledge-project/lisa-feldman-barrett/) - Podcast: [Jennifer Garvey Berger: The Mental Habits of Effective Leaders [The Knowledge Project Ep. #43]](https://podcasts.apple.com/us/podcast/the-knowledge-project-with-shane-parrish/id990149481?i=1000421932549) - Audiobook: [The Neurobiology of "We": How Relationships, the Mind, and the Brain Interact to Shape Who We Are](https://www.amazon.com/Neurobiology-We-Relationships-Interact-Learning/dp/159179949X) - Podcast: [The Price of Distraction [Sam Harris #226]](https://samharris.org/podcasts/226-price-distraction/) ## Things You Can Use - **[Flow](https://flowapp.info/)**: A lightweight work timer and website / app blocker to help you focus. You have to buy Pro to get the URL blocker, but it's $0.99/mo. or $19.99 for lifetime access. - **[Forest](https://www.forestapp.cc/)**: Kate and I started using Forest together. Similar to Flow, it's purpose is to help you focus. The difference with Forest is that it's not really a work focus app. Instead, it incentivizes you to put your phone down. Kate and I love that we can put a timer on together while we're having dinner or watching a show together. - **[Fantastical](https://flexibits.com/fantastical)**: I now have clients in four time zones, and keeping track of all four is a challenge. Fantastical makes it easy to switch between multiple time zones, whereas Google Calendar only allows you to display two time zones at a time. I also love the visual display for Fantastical, and I recommend it for anyone looking for a calendar upgrade. - **[The Chef'n Citrus Orange Squeezer](https://www.amazon.com/gp/product/B006LMVLKO/)**: If you make cocktails or bake with citrus, this is a must-have for the kitchen. No lie. No affiliate code. Just buy this for yourself or your loved ones. This is legitimately one of my favorite purchases of 2020. - **[The Holloway Guide to Raising Venture Capital](https://www.holloway.com/g/venture-capital/about?ref=andysparks1t&vip_code=HLWY30)**: Use this link to get 30% off. Disclosure: this is an affiliate code, but because I'm the guinea pig for Holloway, not because I'm trying to make a buck off you! ## Between In Edition 4 (October 20th), I teased some information about a new podcast I was working on. In-between then and now, I named the podcast. It's called Between, and episodes will live at [between.fm](https://www.between.fm/). The idea behind the show is that it will be a new podcast about relationships between leaders. My favorite way to pitch it is, "It's kind of like Guy Raz's How I Built This, but about the people and relationships behind the businesses and products." ## How You Can Help - If you or anyone you know are interested in working with me as a coach. Reply to this email and let me know so we can set up some time! - If you, or anyone you know, would be interested in reflecting on your startup experience with an emphasis on the people instead of the idea for the podcast, reply or send folks my way! - How was this email? I know it was veeeeeery long. What did you like? What should I keep doing? What should I stop doing? Looking forward to what's next, Andy. --- ### Using a DSLR as a Webcam for Zoom Calls *Published: 2020-12-21* ## My Camera - **Camera:** I have the [Sony Alpha a6400](https://www.amazon.com/gp/product/B07MV3P7M8/ref=ppx_yo_dt_b_asin_title_o06_s00?ie=UTF8&psc=1). - **Lens:** I use the [Tamron 28-75mm F/2.8](https://www.amazon.com/gp/product/B07CSLM1X8/ref=ppx_yo_dt_b_asin_title_o06_s01?ie=UTF8&psc=1). You'll want the 28mm setting so you aren't ultra-zoomed in on, and the lens is versatile for uses other than Zoom calls. - **[Elgato Cam Link 4k](https://www.amazon.com/gp/product/B07K3FN5MR/ref=ppx_yo_dt_b_asin_title_o00_s00?ie=UTF8&psc=1):** You'll need this for hooking the camera up to your computer. - **Other Accessories Needed:** You'll need a [power adapter](https://www.amazon.com/gp/product/B0744JGWQR/ref=ppx_yo_dt_b_asin_title_o06_s01?ie=UTF8&psc=1), [Micro HDMI to HDMI](https://www.amazon.com/gp/product/B0060AU5MW/ref=ppx_yo_dt_b_asin_title_o06_s01?ie=UTF8&psc=1), [SD Card](https://www.amazon.com/gp/product/B07H9DVLBB/ref=ppx_yo_dt_b_asin_title_o06_s00?ie=UTF8&psc=1) (camera won't work without it even though you aren't saving zoom calls to it), and a [USB C Hub](https://www.amazon.com/gp/product/B079GSMZ7G/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1). ## My Desk Setup - **[Grovemade](https://grovemade.com/):** This is a Portland based company that makes incredible desk products. I have a lot of their stuff on my desk for organization and their aesthetics. - **Monitor 1:** [LG UltraFine 4K](https://www.apple.com/shop/product/HMUA2VC/A/lg-ultrafine-4k-display). - **Monitor 2:** I have this tiny little Insignia TV that is like 15 inches that I sit below the camera that I put the Zoom calls on so I can make eye contact. My LG monitor is to the right so I can roll a bit over there and not crane my neck down all the time. - **[Book Stand](https://www.amazon.com/gp/product/B001J9SFXK/):** A basic cookbook stand I use for referencing paper books (I like to read at my desk so I can take notes on my computer as I go). --- ### Captain's Log: October 2020; Letting the Longing Do the Work *Published: 2020-10-20* > "Let the longing do the work" > > Jim Marsden, via Dan Putt Six weeks ago, I wrapped up my last week as CEO of Holloway to pursue a vague new career made up of a mixture of research, writing, and coaching. I used [Rise Sleep](https://www.risescience.com/) to optimize my day for my energy cycles. I made sure not to book meetings before 11am to use my mornings to wake up, meditate, and study. I'd take a meeting or two between 11-12, take my time with lunch in the noon hour, and then a few more meetings before three as my energy dipped. From 3-5, I'd work on a creative project, and I had big plans for creative projects. Thrilled by the excitement of starting a new chapter, I bit off more than I could chew. I realized I was cramming a book, a newsletter, a podcast, coaching, setting up the back office for the business, and learning how to do all of the above in two hours a few days a week. It was clear to me that I'd need to readjust my expectations for this new life. After the last edition of Letters, Dan Putt emailed me with a quote from Reboot coach Jim Marsden. He said Jim tells folks who are in transition to "let the longing do the work." Into a few weeks of this new beginning, I find myself loving coaching more than I expected to. I've shifted my focus to projects that support becoming a coach, and while writing a book and creating a podcast and all that are still things I'm working on, there's only so much time. ## Updates I've been throwing myself into books on the subject of coaching, and I want to keep studying. Many coaches have been generous with their time and shared their experiences over the phone or Zoom or long DM threads on Twitter. I'm loving this period of learning and am grateful for all the time folks have been giving. One friend asked if I'd coach them and their co-founder, giving me my first "practice clients." Today I have eight clients. I thought I'd be pouring all of my creative energy into a new book and accompanying podcast, but a "too good to be true" opportunity to combine my love of writing with my new career as a coach materialized after a phone call with a friend. It's a newsletter in collaboration with a highly sought after coach. The first edition comes out next Wednesday. As for the book, I think it will still happen, but the coaching and the writing will help me get there a bit more informally. As for the podcast, it's still happening in the background. My vision is that it will be like How I Built This, but about the people instead of the ideas. I've been riffing on the concept of structuring conversations as one part "post-game analysis" and one part "dungeons-and-dragons." We'll pull in founders to talk about how they formed a team (Level 7 engineer and a Level 2 marketer?), we'll talk about significant peaks and valleys in the relationship, and debrief how the founders feel with the benefit of hindsight. An incredibly talented composer friend is working on the theme music, and I think I know the designer I'll rope in for the art. I have a few founders who have agreed to come on the show. I'd like to book 10 episodes for early 2021, so if you know any founders who would be willing to do a "post-game analysis" of their experience, I'd love to chat with them. Finally, I've been giving myself time and space to think. For the last couple of weeks, I've been spending mornings with coffee sitting on the benches at the top of Dolores Park. I've felt guilty about this time because it hasn't felt "productive." I almost stopped going until a friend convinced me to keep it up. The next morning, inspiration struck, and I power-walked home where I totally redesigned and shipped an update to my personal site that I am absolutely loving. Check it out here, and please send feedback! Looking forward to what's next, Andy. **P.S.** Thank you to all 80+ people who replied to the last email with offers to help. The internet is such a cool place. ## How You Can Help If you, or anyone you know are interested in working with me as a coach. Send me a note at hi@andysparks.co. If you, or anyone you know, would be interested in reflecting on your startup experience with an emphasis on the people instead of the idea for the podcast, send me a note at hi@andysparks.co. Check out my new website and send feedback to hi@andysparks.co. --- ### The Next Chapter of My Career *Published: 2020-09-03* > "There are neither beginnings nor endings to the turning of the Wheel of Time. But it was a beginning." > > -- Robert Jordan, *The Wheel of Time* This week, I handed Holloway's CEO reins over to my co-founder, [Josh Levy](https://twitter.com/ojoshe). As we built [Holloway](https://www.holloway.com/) over the last four years, I got the chance to explore the depths of my love for research, writing, and sharing stories. My belief in the purpose and mission of this company hasn't wavered, but over the last six months I found myself wishing I could be a full-time independent creator. And at the end of July Josh and I came up with a way for me to do that. As a company, we're in a powerful position, and I continue to be enthusiastic about Holloway's future. This summer, we published two new books, signed eight additional authors, created our first print editions, and built publishing infrastructure that streamlines our print and digital production processes. We're on track to build an alternative to the Amazon Kindle monolith by empowering authors to publish and market their books on the web. Josh is the right person to lead Holloway. Over the last four years, he's driven the development of the Holloway Reader and sculpted each Holloway Guide. He's been instrumental in closing deals with authors and he's pushed the frontier of what it means to be a digital publisher. As for me, I'll remain on the board and continue to be involved with several projects in a significant way at Holloway. ## How We Got Here A combination of factors led me to decide it was time to hand the reins over to Josh. The first was an intense period of taking stock on life, work, the universe, and everything, thanks to the many events of 2020. The second was a slow burn of watching friends have the courage to begin new career chapters as independent creators. And the third involved getting an idea that kept drawing me in despite doing my best to ignore it. In 2019, we published my first book, and I wrote a weekly newsletter. I loved it. For the first time in my life, I felt like the writer I had hoped I'd become since I was a teenager. I remember walking up 5th Avenue with our Senior Editor, [Rachel Jepsen](https://twitter.com/DidYouWriteThat), when she, responding to something I said, told me "You're such a writer." That meant the world to me. As COVID hit, I felt overwhelmed. I dealt with a bout of depression for the first time since 2017. I tried to journal my way out of the crisis, and one thing I realized was that without a book or a newsletter to write, I felt like I'd lost a big part of myself. In April and May, I watched my friend [Nathan Baschez](https://twitter.com/nbashaw) pursue a new career as an independent writer with his newsletter, [Divinations](https://divinations.substack.com/). I envied Nathan. During the same time, I listened to friends struggle with personal and professional relationships, and I realized how the fact that people chose to come to me in these moments was something I should pay attention to. I enjoy listening and doing my best to help. I started four companies with different people each time--relationships between co-founders are something I think about a lot, and something I've had a lot of experience getting wrong and getting right and learning why. In a rare bright moment in 2020, I got on my feet and began to gain new perspective after my girlfriend, Kate, and I decided to get an apartment in San Francisco after being on opposite sides of the country for a year. I turned to Kate one night and told her that I loved Holloway and our team, but I was feeling drawn to explore something--something I needed my experience at Holloway to discover. What if I spent the next few years researching, writing, and helping co-founders learn how to form and nurture healthy relationships? I started to write another book. After a while, I felt like I was cheating on Holloway, sneaking off at night to outline and draft. I didn't want to wait until 2025 to pursue the project, and after everything that had happened this year, and someone I trusted to turn to, I realized I didn't have to. So I told Josh what I was thinking, and as he and I were planning for the next phase of Holloway in the summer, we decided we'd restructure the company with him at the helm, enabling me to pursue this new project. It was anything but easy, but I'm proud that he and I were able to work this out. As for the scope of my new venture, it's a work in progress, but one of the principles I've laid out is to work in public. My number one objective is to get to the heart of what separates co-founders with healthy relationships (with each other, at home, and with their team) from co-founders with toxic ones. I hope it'll be considered a sequel to [Noam Wasserman's](https://twitter.com/noamwass) [*The Founder's Dilemmas*](https://www.amazon.com/Founders-Dilemmas-Anticipating-Foundation-Entrepreneurship/dp/0691158304). I plan on publishing a portion of my writing for free and making another portion paid, and I'm creating a podcast to share interviews when folks feel comfortable going on the record. A big part of why I'm doing this is because of what I've learned about publishing from working on Holloway. I think the breakout authors of the next decade will be those who write in public on Twitter, Medium, Substack, and any other platforms that give writers the tools to build a supportive audience as they learn and share. I hope to publish my book on co-founder relationships on Holloway one day, and I encourage others to think about Holloway as a place to roll your newsletters and blogs up into beautiful digital and print books. In addition to creating, I'm committing myself to learning and working hands-on to help other founders. My first step was to enroll in [The Hudson Institute's](https://hudsoninstitute.com/) coach certification program. If you've considered hiring a coach, I begin my certification in January, but I'd love to start getting my sea legs this fall. If this excites you, please sign up for my mailing list in the green box below. If you have ideas you'd like to share, or you're interested in speaking with me about coaching, please shoot me an email at [hi@andysparks.co](mailto:hi@andysparks.co). Working on Holloway has been one of the greatest joys in my life. I'd like to thank [Josh Levy](https://twitter.com/ojoshe), [Rachel Jepsen](https://twitter.com/DidYouWriteThat), [Dmitriy Kharchenko](https://twitter.com/dmitriy_js), [Hope Hackett](https://twitter.com/Hopeopolis), [Courtney Nash](https://twitter.com/courtneynash), and [Vahe Hovhannisyan](https://twitter.com/vhpoet), and to our investors, my friends, and my family. I'm grateful for the team's support in this decision, and I'm extra grateful to Josh Levy for stepping up and taking on the responsibility of leading the company. Looking forward to what's next, Andy. ## How You Can Help - If you know any co-founders (or groups of co-founders) who would be willing to speak with me (on the record is a plus, but not required), I'd love an introduction. - If you know anyone with experience working with a coach, I'd love to speak with them to learn how I can offer the most value. - If you're interested in learning more about Holloway, as an author, investor, etc. You can still reach out to me, or you're welcome to speak directly with Josh, too, at [josh@holloway.com](mailto:josh@holloway.com). --- ### Failure is a Process *Published: 2019-12-22* > "The longer you live, the more you fail. Failure is the mark of a life well lived." > > Brandon Sanderson, [*Oathbringer*](https://www.amazon.com/Oathbringer-Book-Three-Stormlight-Archive/dp/076532637X), p. 789 A few weeks ago, a Good Work reader asked if I'd write about recovering from failure. At Holloway, we have a policy of keeping Good Work to four paragraphs and a set of links. But I felt like this subject was worth making an exception for. I was grateful to have been given the opportunity to think about this one. In my twenties, I started two companies. One never grew past three people and a bank balance of $50K. For the other, we raised $17M, hired over 70 people, and had product-market fit. Both companies ultimately failed, and each failure taught me something different. When we talk about failure, we're usually talking about it like it's an event. Post mortems have become de rigueur. "I'm sitting in my office, we just sold all the chairs, it's over." But the event of something ending is rarely the worst part of the affair. Failure is actually a process, the downward ridge into despair, a spiraling slide with neon reminders of how far you are from ever getting back on top of things. At 22, I got fired when I told my boss I was flying from Ohio to California for an interview with Y Combinator. I'd been working on a side project with a couple of friends, and we were going to see if we could turn it into a real company. I can't speak to why my co-founders (still two of my best friends) wanted to build a startup, but my reasons were all the wrong ones. Less than a year later, the whole operation turned out the way things do when a kid straps on wooden wings and jumps off a barn. Except that I was an adult, and this failure didn't end with a broken arm but with me standing on a train platform wondering whether jumping would be better than whatever was coming next. Looking back, I can't help but be ashamed of what I see as the juvenile reaction of a kid from the suburbs experiencing something truly hard for the first time. But it's exactly this kind of negative self-talk that leads us to spiral when we're already tumbling. Whether I was justified in how I felt didn't matter. I felt how I felt, and you can't deal with those feelings if you're ashamed of them. Sometime around then, I met up with my friend Danielle Morrill. She noticed something was off, asked me if I was broke, and offered to cook me dinner. She poured some confidence in my cup, and I used to it call my parents. It turns out my Dad had socked away half of my allowance each year as a kid and put it in some stocks. "It's your money," he said. It was about two months of cash. I used it to stay out of Mom and Dad's basement, email everyone I could, begin interviewing, and teach myself the easy half of front-end development. This part is important, because I didn't lift myself out of failure all on my own. I had help, and I know not everyone does. Two months later, I had a job offer to move to New York. I told Danielle. To my surprise, she told me she was going to take the cash remaining in her startup's bank account and start something new. Would I join her? I told the other company no and yes to Danielle. Two months after that, we named the company Mattermark. Able to pay rent, I was, in many ways, out of the woods. But whatever confidence I had at 22 when I moved to California was gone. Someone once said not to compare others' outsides to your insides. I did a lot of this at that point in my life. And I projected a stable outside as often as I could, too. My Facebook feed was full of fundraising announcements and photos of our team having a good time. The reality was that I drank too much, smoked too much, and exercised only because it made me feel something. After things go pear shaped, we struggle just to grasp what's going on, it's next to impossible to figure out how to get our footing. Up until 2015, I had flirted with writing a few times. When my first company failed, I wrote a series on what went wrong to process the lessons. I journaled here and there, but in 2015 I set out to start writing 750 words a day as often as I could. In 2014, I journaled seventeen times. In 2015, that number rose to sixty-eight, and in 2016 I hit seventy-five. Writing became the place I could go to have an honest conversation. My audience, me, knew all my secrets. I didn't have to hide anything or contextualize how I felt, but I could pull on some threads and patterns to figure out why I was so unhappy. Building Mattermark wasn't center-stage for me. This was. Meanwhile, Mattermark was on its way down. We'd started a business. Despite being in a market too small for our venture capital britches, we had product-market fit. We built a terrific team. We formed and deepened friendships. We raised a truckload of capital. But we were poor managers, reactionary to markets and conversations. We wavered in our decision making, and we ultimately tried to scale prematurely inside a market we didn't fully understand. It was a more spectacular failure than my first business, but this one didn't hit me like the first one did. Partially because I left before we hit the bottom, not jumping ship out of fear but because I saw what this company was doing to me. In many ways, Danielle saved me. But as I clawed my way up from the bottom while the company grew, I regained my agency and ultimately I saw that, in order to get back to the top, I needed to build my own path, not someone else's. So I left. We sold the company, the story was not favorable, and I often wonder if it was my fault for failing to stay to try and right the ship's course. In the weeks after my last day at Mattermark, even though the thing itself was a failure, I felt like I had finally crawled out of the crater I'd descended into from 22 to 27. But two years later, I was [still struggling](/essays/confidence) for confidence. Only now, in the last three months or so, do I feel like I've traveled far beyond my origin of failure, into new territory. Recovering from failure took me seven years. And I'm sure there's some shadow lurking around a corner that will make me laugh at that sentence in a few years. Maybe we're always in recovery. If we want to stay vigilant, we should think of it that way. What I learned from writing is that our body is profoundly good at setting off biological klaxons, screaming at us to head for the exits. The impulse to drink, smoke, turn our brains off, check out, or criticise others, and emotional reactions like short fuses, inability to sleep, grinding our teeth, all of these things are how our body tells us something is wrong. I learned to listen to those messages, to hear them, by seeking help from a lot of different people, from friends and coaches, but most importantly through writing. I started to really reflect on what had happened to me in the past, on things I had done, and how they were still affecting me. In turn, I began to think about how things could be different and what could happen next. In many ways, failure is the most incredible, beautiful thing. Had I not failed so early, who knows if I ever would have found my love of writing, written a book, or founded a company to give authors a better way to publish books online. My experience of failure helped me empathize with those who didn't have anywhere near the head start I had. It showed me that depression isn't a mood you get, it's a disease you can catch. It taught me to feel my fear, listen to it, follow it, and face it. But most importantly, it taught me that I could survive it the next time it came around. --- ### Knocking on Doors *Published: 2019-12-15* > "The best journeys answer questions that, in the beginning, you didn't even think to ask." > > Unknown Over the last year, I've spent a lot of time thinking about how we get the word out about Holloway. I've read more than I ever thought I would about the field of marketing, but the thing that surprised me the most is how important it is to understand, and master, what I call "having a good ground game." In politics this means knocking on doors, canvassing neighborhoods, and talking to people face-to-face. When we were starting Mattermark, we emailed every single investor we could with a screenshot of data about their firm in our product, offer a demo, and see if they would respond. At Holloway, I keep a list of people and when we publish something I think they'd like, I shoot them a DM on [Twitter](https://x.com/andysparks) or a quick email. Often, they volunteer to share it without me even needing to ask. Sharing your work and asking for help spreading the word is intimidating. Nobody wants to be a spammer, and we're often afraid of asking for too much. And some people do ask for too much. The key to keeping out of shady spam territory and in the land of a sincere effort to grow something you love is to remember that it's not about you. If you send someone an article you wrote and they genuinely love the thing, then you did them a favor. --- ### Hilarious Mistakes *Published: 2019-12-08* > "Out of danger and restless insecurity comes the force that pushes mankind to newer and loftier conquests." > > Isaac Asimov, *The End of Eternity* I loved video games in middle school. So when the Xbox came out, I made an appeal to my parents to purchase this glorious machine. My dad, forever the teacher, told me I could have one if I figured out a way to pay for it. I came up with a scheme to use all the assorted machinery in the garage, lawnmower, leaf blower, that kind of thing, to see if I could sell my services to the neighbors. Never imagining I'd take it where I would, my parents set me off on what would become my first formal campaign to acquire clients. At eleven or twelve years old, I wasn't very imaginative when it comes to naming, and I was unfortunately (or fortunately, depending how you look at it) hopelessly naive. We had red white and blue bordered stationery I could use to advertise my business, so I figured the prefix would be simple: an all American operation offering lawn mowing and leaf blowing. A few hours later, my Mom burst in the front door barely able to breathe, tears running down her face. Apparently, "All American Mow and Blow" hadn't been a good choice for my inaugural enterprise, and you can imagine how embarrassed I was, even though I didn't really get the problem with the name at the time. The family jokes about how I offered the entire neighborhood a $30 combo mow and blow will never stop. When we screw up, put our foot in our mouth, and feel the heat of embarrassment rush to the face, it doesn't feel like good work. Looking silly, making mistakes, no matter how mortifying, these things are critical to learning how to improve. I don't know what exactly I learned from my childhood entrepreneurship fail, but because I survived it, it makes all the important failures later on, the ones that have a lot to teach me, more manageable. Those events and the stories we tell about them make me human. And they're damn funny to look back on as our friends clutch their sides in laughter as they gasp and squeeze out, "I can't believe you did that." --- ### Keepers *Published: 2019-11-24* > "Rockefeller loved Flagler's dictum that a friendship founded on business was superior to a business founded on friendship, and for several decades they worked together in an almost seamless fashion." > > Ron Chernow, *Titan* Work, as we often think about it, is a place to get things done, to put food on the table, to make that bread. But for me, work has also been the place I've met my closest friends. Kurt Vonnegut wrote that when couples tend to fight, "what they're really saying is, 'you're not enough people.'" We are biologically suited to thrive in groups of ~150, where everyone has a purpose and that purpose is always related to supporting the health of the group. But we don't live in groups of 150. We're connected to billions of people around the world, but we're often alone. As we go about our lives, occasionally we meet people who we'd really like to pair up with, either as friends, romantic partners, bandmates, business partners, drinking buddies, D&D teammates, or whatever. I call these people fellow travelers; my friend Carrie calls them "keepers." Churches, schools, and book clubs allow us to scale down the global village to include people with similar goals, priorities, and values. But we don't all attend churches, play music, go to school, or have the time for a weekly book club. Just about all of us go to work. Rarely, when considering a new job opportunity, do we consider the likelihood of whether someone on the team will be a keeper. However important our work is and feels, when the work is done, it's the friendships, the keepers, we'll value above all else. --- ### Applying Science Terminology to Business *Published: 2019-11-17* At Mattermark, the company I helped start before Holloway, we were in the business of collecting data on private companies so investors could determine which ones might make good investment targets. To measure this and convey it to our customers, we began thinking about companies in terms of physics equations. For example, we built a "momentum score" (momentum = mass * velocity) that took into account how big the company was and how fast it was either growing or shrinking. Another physics concept I love to apply to a business is entropy. I'm convinced that the key to teamwork lies in how one manages the cycle of order to chaos, chaos back to order. Like those scenes in the movies where the general walks down the silent and still ranks of his men before battle to deliver a rallying speech, annual planning, a process many of us are undoubtedly part of right now, exists to bring the team up to a local maximum of order. Tim O'Reilly uses another term, not from physics but evolutionary biology, to describe business: [fitness landscapes](https://www.slideshare.net/timoreilly/the-real-work-of-the-21st-century/5-Technology_has_a_fitness_landscapeIn). The idea is simple. Picture a two-dimensional space with peaks and valleys. The peaks are the local maxima, the valleys the local minima. To navigate from one peak to a taller one, you have to climb down into a valley and then begin a new climb. In reality, the landscape is not two-dimensional, nor is it stable. The market is a constantly evolving three-dimensional landscape where one change from one company can make one peak rise and others fall. The leader must always be collecting information to both level up the team's ability to summit peaks and decide when a peak is worth leaving. So what is Good Work? Good Work is fifty years of getting good at climbing. --- ### Benchmark Your Knowledge With the Urban Scale *Published: 2019-11-10* Have you ever noticed that learning to swim feels a lot like drowning? At least at first. How can we tell when all that flailing around is actually exactly what we're supposed to do on our way to mastery? Founders have to start from scratch a lot. When you're hiring someone new to lead a function, for instance, you have to master enough of the material to assess someone else's ability to actually take action in that domain. Design, marketing, or engineering--how do you know when you've learned enough? If you've worked at a startup, whether as a founder or employee, you're definitely familiar with the joys and challenges of learning on the job. In my twenties, I co-founded three companies. At my first two companies, I had to learn everything from operations (accounting, compliance, legal), sales (how to sell a thing, how to hire salespeople, how to hire sales leadership, how to be a sales leader, sales strategy), customer success, recruiting, hiring, firing, layoffs, and much more. The only way I could manage this was to remind myself that if it felt like drowning, swimming was around the corner. Just over three years ago, I decided to leave the second company, Mattermark. A week or so after I had left, unemployed for the first time since college, I stood at a bar with one of my former colleagues, now my best friend. As someone who knew me better than anyone else, I asked him what I should work on getting better at as I began exploring what I would do next. He told me I got in over my head too easily, assuming I had learned more than I had, trying to plow forward too soon. Poor results and poorer credibility were all I was going to get by not giving enough respect to what I didn't know. That's really what it's all about. If you're learning to swim, and you don't respect the water, you actually are going to drown. If you're learning to swim, talk to the best swimmers you can find. But also talk to people who just learned to swim themselves, and even other people who are learning, too. These days, I use Tim Urban's "1-10 scale of knowledge" (I call it, brilliantly, "the Urban Scale") to accurately judge how far along I am in mastering something new--or at least becoming as familiar with it as I need to be to not massively fuck things up. I try to make sure that I know enough to be able to tell if someone else is struggling in that domain, if they're "[not waving but drowning](https://www.poetryfoundation.org/poems/46479/not-waving-but-drowning)." I might not be able to bring them back to shore by myself, but I'll know the signs, and be able to call the right people for help. --- ### Procrastination is a Useful Signal *Published: 2019-10-20* > "And indeed, that IS the question: whether to float with the tide, or to swim for a goal. It is a choice we must all make consciously or unconsciously at one time in our lives. So few people understand this!" > > -- Hunter S. Thompson, [*Letters of Note*](https://www.amazon.com/gp/product/1452134251/) Yoda said, "Do or do not," but do I did not. This week's Good Work is one week late and about procrastination. Procrastination starts when a task is added to one of our many plates, and we don't decide and communicate that it isn't urgent, that we can't consume that much right now. Sometimes we record the task in a to-do list. In other moments we tell ourselves a cute story, "I'll remember it in the morning." Out of no malice, we neglect the task. We come up with amazing excuses why the thing isn't worth getting to at all. But sometimes, it needed getting to, and gotten to it did not get, leaving us to feel like someone's taken a vacuum cleaner to our integrity, and in this moment, we have a choice. Do we face the mistake, or do we defer further? We defer further because we are embarrassed. We feel guilty for letting someone down--sometimes ourselves. Having not been honest, we may have bruised someone's trust, and now we don't know what balm we can provide. And so it compounds, dragging us down into a Great Period of Putting Things Off. We feel like a whale stuck with a thousand harpoons made of tasks, emails, text messages, and asks. We become masterful tragic storytellers. What great promethean burdens we carry, what great-bellied calamities our lives become, and what great comforters of self-pity we wrap around ourselves. In the short run, it's easier to delay than it is to pen a postponement atonement and far less challenging than coming clean with yourself that you aren't very good at staying on top of the ball always and forever. Sometimes we just avoid doing hard things. But more often than not, we procrastinate because something else drew our attention. What's necessary is learning to notice what we're valuing as important. When something doesn't fit in the important bucket, it helps to learn to say, "No. I'm sorry, but I don't have time for this right now," or, "I'm sorry, but I'm overcommitted right now. If I take this on, I won't get to X." It's about honesty, with yourself *and* those around you. Instead of punting, face the task, the mistake, the conflict, and either decide to do it, schedule it, or make sure you and everyone involved knows it ain't gonna happen. --- ### Polishing Hinges *Published: 2019-10-06* In my century-old house, the hinges on every door are covered in layers of paint. For a hundred years, the people painting this house refused to find a screwdriver or to tape around the hinges, dooming me to stare at this mess. On Holloway's Work-From-Home Wednesday this week, around 5 o'clock PM, some part of me snapped. I had to go nuclear on those suckers, strip them down to the brass I knew lay below the strata of practical beiges, "Careful Whisper" blues, and a hundred other bad decisions and attempts to mask them. On the way to the hardware store with plans to strip every hinge in the house, and sand a quarter inch off the bottom of a door that kept catching on the carpet, my brain confronted me. "Is there a better use of your evening? How 'bout taking something off the top of your to-do list, brother? Something urgent and important or, hell, leave urgent out of the equation and go with something plain old important." As if sitting across the table from a colleague, I thought back to myself, "Great point, but [how about no?](https://www.youtube.com/watch?v=lITBGjNEp08)" The rest of the night, as I sanded and boiled off the latex and lord knows what they used to paint in the 1920's (yeah, I know, freaking lead), I kept asking myself, "What on Earth are you doing this for?" Some call this [Yak Shaving](https://www.hanselman.com/blog/YakShavingDefinedIllGetThatDoneAsSoonAsIShaveThisYak.aspx), portrayed with brilliance in *Malcolm in the Middle* with [Hal fixing a light bulb](https://www.youtube.com/watch?v=AbSehcT19u0). See, my *actual work*, you know, the stuff I spend fifty or sixty hours a week doing and getting paid for, consists of jumping between product design, writing-to-think, writing-to-publish, internal and external meetings, spreadsheets for finance, spreadsheets for marketing, and no shortage of staring out the window while waiting for my thoughts to fall into place like [Teewees and Orange Rickies](https://www.joe.co.uk/gaming/tetris-block-names-221127) onto the cool blue infinite of my entire life. Rarely does my work afford me the twin pleasures of starting something and finishing it in a day, and *oh my god it's a real thing I can touch, point to, or use, something done.* In the end, I got down to brass. As I cleaned the sawdust out of every cavity of my home, muscles aching from handling and sanding the beast of the old door, I realized how important it is to me to have that tactile achievement, every once in a while, to have something to point to and say, "I did that." I had only improved minute details I doubt others will ever notice. Certainly, no one's saying thank you. But what is Good Work at any level, from building a company to raising a skyscraper, if not work done with patience and dedication? A conscientious commitment to steady, incremental progress, week after week, for years at a time? If infinite regress is "turtles all the way down," maybe progress is just polishing hinges. > "There's nothing intrinsic about the manual trades when it comes to generating this particular source of meaning. Any pursuit--be it physical or cognitive--that supports high levels of skill can also generate a sense of sacredness." > > -- Cal Newport, *[Deep Work](https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692)*, p. 89 --- ### The Three Tenets of Trust *Published: 2019-09-29* > "Watching Tom manage, it seemed to me that he applied a simple three-step algorithm to every problem: 1. Who owns the problem? 2. Do I trust them? 3. How do I find an owner I trust? If you can't find an owner, that's the problem right there. Skip to step 3." > > -- Dave Hitz, *How to Castrate a Bull*, p. 108 When I sat down to write this week's Good Work, I stumbled on a note I'd taken of something executive coach [Khalid Halim](https://twitter.com/khalidhalim) told me in July of 2016: "**Trust** is made up of three things: sincerity, reliability, and competence. And trust crumbles at anything less than having all three." Over the next year, as we founded Holloway, Josh and I spoke about these three tenets of trust at length. They became the foundation for how we think about Holloway's brand. It's not enough to be competent explainers of gnarly professional challenges. Our readers need to be able to depend on what we produce and share, and they need to be able to *feel* the sincerity of our commitment to helping the internet grow up into a place that isn't just word hucksters shilling for clicks. When we feel like the people we work with are driving us nuts, cracked and crumbling trust tends to be the culprit. Whether we're blaming others, blaming ourselves (yes, mistrust works that way, too), or plain frustrated because we don't understand what we're frustrated at, it can help to step back and ask ourselves whether we're dealing with a sincerity, reliability, or competence issue. The last thing I'll add is that trust should not be treated as a binary undertaking. If you force yourself to choose between 100% trust and 0% trust, you're likely to find yourself living in a terrifying interpersonal [dark forest](http://blogs.discovermagazine.com/lovesick-cyborg/2015/10/31/chinas-dark-forest-answer-to-star-wars-optimism/#.XY1PuZNKhR4). A much more pleasant approach to trust is Shopify CEO Tobi Lutke's "[trust battery](https://www.nytimes.com/2016/04/24/business/tobi-lutke-of-shopify-powering-a-team-with-a-trust-battery.html)," allowing you to to think of trust as a spectrum of charge and discharge. --- ### Complaints Are Gifts *Published: 2019-09-21* In the first few years I was managing people it felt like everyone had something to complain about. The grievances poured into a sad swimming pool of injustice. I did my best to address the issues, but it doesn't take many complaints at once to overwhelm even the most well-intentioned managers. I quickly came to dread complaints, becoming fast friends with phrases like, "Here we go again." Struggling, my co-founder suggested I work with an executive coach. The coach I found, Christina, encouraged me to think of complaints as gifts. Because when someone on the team complains, what's really happening is that they're standing up for something. They're saying, "Something's going on here and I am not okay with it." Complaints are rarely delivered in crisp and clear language. The aggrieved might not call direct attention to systemic issues, but they're like canaries calling out symptoms of what those deep issues might be. The actual words of a complaint may appear to be about one surface-level thing, but a good manager can tell when they're a sign that there's a much larger issue. As a manager, it's critical to listen to the gripes, even when they seem small. When we don't know how to solve something, we can revert to our child-selves--turn up the volume, say the same thing over and over again, hoping we'll be heard. Don't fall prey to the mistake of interpreting this behavior as whining or a desire to shirk responsibility. Instead, look at each complaint as an expression of pain, someone asking that you listen and help them solve a problem, together. Finally, remember that each complaint is someone doing their best to improve the team. If you trust that they are in this with you, you need to listen. --- ### Work Worth Doing *Published: 2019-09-07* > "Good work finds the way between pride and despair. / It graces with health. It heals with grace. It preserves the given so that it remains a gift. / By it, we lose loneliness: / we clasp the hands of those who go before us, and the hands of those who come after us; / we enter the little circle of each other's arms, / and the larger circle of all creatures, passing in and out of life, who move also in a dance, to a music so subtle and vast that no ear hears it except in fragments." > > -- Wendell Berry, *What Are People For?* When work is a choice, why the hell do some people choose to do it? Why would someone with $2M, $50M, or $800M in the bank choose to do the kinds of daily tasks most people think of as chores, or necessary evils? Only when work becomes a choice do we realize the thing about work that *is worth choosing*. Too late, we realize it was available to us the entire time. It's been like Navi in Zelda: "[Hey, LISTEN!](https://www.youtube.com/watch?v=seKaU-qQuts)" But we weren't. This isn't to say everyone should be passionate about what they do for a living. And this isn't to say that you'll find the joy of good work at your job. It's about discovering the moments in your life when you feel a sense of relief at *facing* a problem, sitting down at the keyboard, or otherwise setting sail. It requires work, real effort, to figure out what, if you had the choice to work, you would choose to work *for*. To discover whether there's anything you do--whether you get paid for it or not--that gives you a sense of relief. I think a lot of us would find similarities among the things we choose. At least, I imagine that work worth doing gives us the chance to experiment and play. I think it's done in the hope of bringing something to others in collaboration or gesture, or else it's built on the work of others, and so it's an antidote to loneliness, even when you're alone. What kind of work is worth doing? What do you--or what would you--choose to work for? --- ### Reading Fiction Will Help Your Career *Published: 2019-06-15* > "A book is proof that humans are capable of working magic." > > -- Carl Sagan, *Cosmos*, Ep. 11 It's hard to make the case that studying someone who mastered a craft by reading their biography would be a waste of time. Likewise, reading popular non-fiction that aims to explain how some part of the world works can hardly be spun as a *waste* of time. But it's a hell of a lot less clear how *fiction* fits into the picture of self-directed professional growth. After all, how could something *made up* be related to a career? But isn't that exactly what a career is--something made up? Careers and companies are made up of and made up *by* people every day--both start as ideas in someone's head, and through sweat and collaboration and a lot of luck the idea just might manifest. Fiction can be like a [magic school bus](https://www.youtube.com/watch?v=v53mhRXXT2g) we can hop on to explore endless possible worlds, which isn't so different from how a founder thinks about their company's mission. The folks behind fiction open up windows to the lives and minds of those quite unlike us, who are somehow also us. By showing us what we could be, they reveal what we are. Fiction can motivate us and steady us, inspire us and humble us. Every time I find myself frustrated with someone in a professional context, I remember a line from John Steinbeck's [*East of Eden*](https://www.amazon.com/East-Eden-Penguin-Orange-Collection/dp/0143129481): "I am certain that underneath their topmost layers of frailty men want to be good and want to be loved. Indeed, most of their vices are attempted short cuts to love." And every time I find myself in a fit of excitement over a new idea, I think of Frank Herbert's words in [*Dune*](https://www.amazon.com/Dune-Frank-Herbert/dp/0441172717): "Hope clouds observation." If you want to better understand your customers, coworkers, and investors, turn to fiction to help you gain some empathy and perspective and see into the minds of others. And don't forget that the best fiction is created to help you understand something about yourself that you didn't before; any founder or investor will tell you that the most important quality of a good leader is self-awareness. Consider fiction a master course in psychology, and a mirror to who we really are. You won't get lost here. It's a place you go to be found. --- ### Books: The Perfect Career Companions *Published: 2019-06-08* > "Reading is the work of the alert mind, is demanding, and under ideal conditions produces finally a sort of ecstasy." -- E.B. White When I was nineteen, a friend and I started brewing beer. I headed to Barnes & Noble and asked the gentleman at the counter if there were any books about brewing beer. Without a worry over being complicit in an underage brewing ring, he ultimately helped me find [*Brewing Up a Business*](https://www.amazon.com/Brewing-Up-Business-Adventures-Founder/dp/0470942312) by Dogfish Head Brewing Company founder Sam Calagione. So began my career as an entrepreneur. Since then I've bought books on how to write, sell, market a product, manage people, lead a team, understand design, build a product, and more. Sometimes I sit around wondering what the world would be like if macaroni came in even more shapes (what's your favorite?). Sometimes I wonder what the world would be like if we taught young students the methods and joys of lifelong learning. If a class existed called "Your Responsibility to Educate Yourself," I'd be racing to write the curriculum for what would doubtless be the very first lesson: "How to Use Books to Learn How to Do the Thing You Want to Learn How to Do for the Very Low Price of $9.99." Only 57% of U.S. adults in 2016 said they are "likely to read for work or school" and in 2018, 24% haven't read a book "in whole or in part" in the last year. Degree or no degree, the chances are you're stuck on something in your career. Whether you're yearning to move from customer support to product management, you wanna learn how to code, or you're distraught over your failure to scratch your itch to write, I'd be willing to bet a fair amount of cheddar that there's a book out there that would take you several steps toward getting that thing you want. Someone has struggled with the same shit before. I've had $10 books that have changed my life more materially than an entire four years of college was able to do. Think of spending money on books not as a cost, but as an investment. If you're cost- or environmentally conscious (or hell, you just like books), [find a library](https://theculturetrip.com/north-america/usa/california/articles/the-best-libraries-in-san-francisco/) or a [library app](https://www.onlinecollege.org/2012/03/06/top-25-library-apps-for-the-ipad/). As for time, you don't have to have two free hours every day to make this work. I read over breakfast or lunch at least three times a week (it's on my schedule!). That adds up to over 100 hours of reading time a year. Compare that to the time you'd waste if you had to invent the wheel every time you wanted to drive. --- ### Putting People in Play *Published: 2019-06-01* > "For small creatures such as we the vastness is bearable only through love." > > -- Carl Sagan, *Contact*, p. 430 [Julian Weisser](https://twitter.com/julianweisser) introduced me to a phrase I fell in love with this week: "putting people in play." Over my career, I've repeatedly felt like a threadbare piece of discount clothing, not much good in the first place, stretched thin, and useful to nobody. Growing up, it felt like so many of the adults I knew had sold their souls for rafts of stability. Being an optimist, believing there's big, bold, and beautiful opportunities in life, turned me into this angry sort of Holden Caulfield who just thought everyone else kind of sucked. It's hard to look back on the person I was, clawing for an opportunity to find some depth to life. And then one day I met a fellow named [Luke Barbara](https://twitter.com/LukeBarbara). Over a couple years, Luke was my Yoda. I'm not sure what he saw, but somehow he managed to pull the positivity out. When the first business I tried to start went under, he got me my first internship at a technology company. Luke put me in play. As I've gotten older, I've begun to prefer working with people with a lot of experience, but my conversation with Julian this week made me see how preference is causing me to miss out on the opportunity to work with incredible people who just need someone to put them into play. If you feel like you just need someone to see you or put you into play, email me (I'm [andy@holloway.com](mailto:andy@holloway.com)). And if you've met someone recently who has that undefinable but obvious spark, consider putting them in play. It will mean the world to them--and to you. --- ### You Exist Outside of Work *Published: 2019-05-25* > "Weekends don't count unless you spend them doing something completely pointless." -- [Bill Watterson](https://twitter.com/calvinn_hobbes/status/1053347230696976384) There's this perverted idea that taking time to rest is an indulgence, like catching our breath over the weekend is the equivalent of eating a swimming pool of Ben & Jerry's Cherry Garcia. For many of us, our work takes on the personality of a jealous and territorial lover. One day you wake up, hungover from a fight with work the night before, power cords flung around the room, fingers stained with the dregs of coffee we sucked through the filters in the trash, realizing you've missed any depth of life outside your codependent relationship with work. I say all of this as someone who loves their work. Each Friday, I head out to meet my best friend in the world for a few too many beers and talk about... what else? My relationship. Work. But this weekend is a long weekend. It's Memorial Day Weekend in The United States. If you're anything like me, you're thinking about working on Monday. You see a clear schedule and a backlog a mile wide or twenty thousand leagues deep. There's so much to do. There are people depending on us. There's a career that needs to be nurtured. And all of that is true. But this weekend, I hope you won't work on Monday. I hope you step back, call a friend who you've lost touch with, sit in that park you always walk past, read that book that's sat on your shelf, tell your partner that thing you've been thinking about, or book that trip you've been dreaming of. Whether you love your work or you look at email like a ball and chain, just remember that you exist outside of this relationship, and it's never too late to learn more about who you are beyond and before your work. I hope you take your plans for working on Monday and do what the writers of Game of Thrones should have done with this last season's script: crumple 'em up and say, "Not today." --- ### It's Your Ship to Steer *Published: 2019-05-04* > "Journey before destination. There are always several ways to achieve a goal. Failure is preferable to winning through unjust means." > > Brandon Sanderson, *The Way of Kings*, p. 925 There's this Jim Beam commercial I love. It's called [Bold Choices](https://www.youtube.com/watch?v=wYXFLX2vB-Q). It's the best commercial I've ever seen. Yes, it's a commercial advertising an alcoholic beverage, but it's also a beautiful reminder that our lives are not on a strict path from birth, and the bigger the risks you take, the farther you could end up from where you started. No matter how many people we talk with, no matter how many alternatives we consider, our decisions are ultimately ours. We have to live with how we made them and who else they affected. Figuring out why we make the choices we do can be the hardest work of all. Twice in my career have I faced decisions where, when I consulted a web of usually reliable parents, friends, and mentors, I was left feeling morally dehydrated at the prospect of taking their advice. Everyone was *telling* me to do one thing, to act in my interest, to be strong, to be decisive. But something didn't *feel* right. In these moments, I asked myself whether I was suffering from [confirmation bias](https://en.wikipedia.org/wiki/Confirmation_bias) or falling prey to [sunk costs](https://en.wikipedia.org/wiki/Sunk_cost). After writing about it, thinking about it, the best I could do was feel pretty sure I was thinking clearly. But all these people who had been in tricky situations were telling me to look out for *myself only*. What did they know that I didn't and how much would I regret not listening? In both of these moments, I was out to find proof that there's a more effective way of doing things that doesn't involve stepping on others or solely looking out for myself. Because so many of our choices involve the systems we move through, advice from others, and what we're exposed to, I don't believe that a few decisions define who you are. But we are defined by the way we reflect on our choices and whether, moving forward, we can connect the *how* to our *why*. This week, when reading Brandon Sanderson's [*The Way of Kings*](https://www.amazon.com/Way-Kings-Brandon-Sanderson/dp/0765365278), I realize that's the journey I'm on. No matter what you do for a living, I hope you take a few minutes this week to remember his words: > "Journey before destination. There are always several ways to achieve a goal." --- ### Why You Should Take Notes on Everything *Published: 2019-04-13* > "...the secret of hunch cultivation is simple: write everything down." > > -- Steven Johnson, [*Where Good Ideas Come From*](https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380), p. 83 In [*Where Good Ideas Come From*](https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380), Steven Johnson writes about what he calls "the slow hunch." Charles Darwin didn't wake up one day with the entire theory of natural selection worked out, for instance. It took him *months* to work out what his findings in the Galapagos meant, but first he had to write them down. The American sociologist [C. Wright Mills](https://en.wikipedia.org/wiki/C._Wright_Mills) wrote an appendix to his 1959 book on society and the self, [*The Sociological Imagination*](https://en.wikipedia.org/wiki/The_Sociological_Imagination), entitled "On Intellectual Craftsmanship" (scanned portion available [here](https://archivingthecity.files.wordpress.com/2011/01/mills_on_intellctual_craftmanship.pdf)). So perfectly does Mills describes the value of keeping a "file" of one's thoughts, ideas, and other intellectual ephemera, that I feel the only justice I can give it is to tell you to just read the damned thing and share two of my favorite highlights: - "You will have often noticed how carefully accomplished thinkers treat their own minds, how closely they observe their development and organize their experience. The reason they treasure their smallest experiences is that, in the course of a lifetime, modern man has so very little personal experience and yet experience is so important as a source of original intellectual work. To be able to trust yet to be skeptical of your own experience, I have come to believe, is one mark of the mature workman." (p. 196, 197) - "...after a few years of independent work, rather than read entire books, you will very often read parts of many books from the point of view of some particular theme or topic in which you are interested and concerning which you have plans in your file. Therefore, you will take notes which do not fairly represent the books you read. You are using this particular idea, this particular fact, for the realization of your own projects." (p. 199) Whether your work requires you to learn how to lead a team, invent a new product, or write something that moves people, many of your best ideas are likely to come to you over time. Thomas Jefferson kept ivory tablets and charcoal on his belt for taking notes during the day that he would transfer in the evenings to his [commonplace book](https://en.wikipedia.org/wiki/Commonplace_book). Emily Dickinson scrawled lines and ideas on [salvaged scraps of paper](https://www.newyorker.com/magazine/2016/12/05/emily-dickinsons-singular-scrap-poetry). Whether you're a Moleskine person, or you talk into a digital recorder, or you embrace one of the many great [note-taking apps](https://zapier.com/blog/best-note-taking-apps/) out there, we now have more tools at our disposal than ever before for keeping our own file--and keeping track of the thoughts and events whose value is yet to be known. My friend [Zack](https://twitter.com/ZackShapiro) always says, "the best things in life almost don't happen," and our Senior Editor [Rachel](https://twitter.com/DidYouWriteThat) says, "You can't predict which small thing is going to change the course of your life." So when a thought comes to you while you walk to lunch, when you discover a quote that wholly captures the way you see things, when something makes you tilt your head up and to the left and say, "Huh," **write it down**. --- ### Creating a Filter for Friendships and Collaborators *Published: 2019-03-30* > "I feel and think much as you do, care about many of the things you care about, although most people don't care about them. You are not alone." > > -- Kurt Vonnegut, *Timequake*, p. 221 A few weeks back, a friend of mine asked me a question over text. "Now that you are where you are in your career, fairly established, how do you think about building your network and furthering those relationships? Or is it mostly a byproduct of what Holloway needs?" What a lovely question to ask and what a delightful one to answer. But it begins with some immediate bristling. See, I could do without the word *network*. The way we might hear a [Midtown Uniform](https://www.instagram.com/midtownuniform) say, "Totally, bro, I'ma batcall my network," it's a flippant way to describe real people with real lives and real goals and real feelings as commodities we can go shopping for in some theoretical Target that carries people and favors instead of orange juice and [premium mediocre](https://www.ribbonfarm.com/2017/08/17/the-premium-mediocre-life-of-maya-millennial/) blankets. Over the years, I've developed this idea of what I call *fellow travelers*, not a network, not relationships I've built, not my "tribe." Sure, there's all the people in various places on my [Life Mountain](https://waitbutwhy.com/2014/12/10-types-odd-friendships-youre-probably-part.html), but I believe what people are really asking about when they ask about networks is how they find more people to fall in love with. We meet fellow travelers at dysfunctional work functions and places of play. They're the people who share our values. The ones we feel at ease with. The ones we call when we somehow have an open night and want to be real with someone who's real. How do you find fellow travelers and keep them traveling with you? When I was twenty-fiveish, I wrote out my values. The first cut was decent. I valued risk-taking, mastery, and curiosity. Over the years, "People who don't take themselves too goddamned seriously!" has risen to be the quality I value most in friends or colleagues. When you take yourself too seriously, you can't take a joke, you can't take feedback, your ego drives you, and I just don't want to spend my life ride seated next to folks who've wound themselves up so tight that they can't appreciate the absolute and utter absurdity of the experience of being alive. People I met who didn't take themselves too seriously made my traveling feel less alone. Listing out what you value most in yourself and want to see shared by others, or qualities you're struggling to attain or ways of being you simply appreciate can be helpful when looking for fellow travelers. Here are a few more of mine: - Believe in giving assholes a run for their money - Are interested in leaving the planet better than we found it - Love learning, reading, absorbing knowledge - Are willing to abandon certitude in the face of new evidence - Demonstrate character and respect - Are willing to take risks Building your filter helps you recognize these people when you meet them. But finding them is hard enough, so when you do, don't miss the opportunity to reach out. Follow them on Twitter? Interact! See someone's work on YouTube you admire? Find their email and tell them (this is how I met *the* [Michael Marantz](http://michaelmarantz.com/)). Go to conferences. Make it your goal to meet *one* person at the entire conference whom you think you could be friends with for more than ten years. I've been doing this for almost a decade. It's been the single most valuable tool I've sussed for finding fellow travelers. Finally, this is a newsletter about work, *Good Work*. Find your fellow travelers, but don't stop at falling in love with them. Start *making things* with them. Make a short film. Throw a monthly dinner. Buy a canvas, some paint, some firecrackers, and a six pack and see where Sunday takes you. Ask your fellow travelers for help. Show them your writing. Share your goals about doing that thing you'd do if only you *had the time*. Do business with these people. And when they share *their* goals, do your best to make them *your* goals. Hell, that's what they'd do for you, right? --- ### Coaches Should Accelerate Your Growth *Published: 2019-03-24* Tyler Lyman, a new Good Work subscriber, wrote us on Monday asking if we had plans any time soon to explore the relationship between startup founder and executive coach. I hadn't decided what to write about for this week's Good Work yet and thought tackling the subject would be a breeze--my co-founder, Josh, and I happened to be headed in to see our coach the next day. Inspired, I dashed off my thoughts on how working with our amazing coach, Christina Harbridge, has been one of the most valuable professional experiences in my life, when Josh pointed out that most people--even those who can afford it--don't ever get a therapist, let alone a professional executive coach. "Are coaches like having a butler or a gardener--things certain rich people have but only because they have a mansion or a big estate?" he asked. While not quite like having a butler or a gardener, Josh was of course right in pointing out that access to executive coaching is a privilege. In that moment, he also acted as a great coach to me, showing me a blindspot but not making me feel ashamed of it. The best coaches, whether they're a paid executive coach, a parent, or just a friend who listens earnestly over a few pints, perform the same function. Put one way, "A [coach is](https://en.wikipedia.org/wiki/John_Wooden) someone who can give correction without causing resentment." They're there to help you be successful, and to do this they tactfully help you become aware of behavior that's impeding your goals. While coaches can be valuable regardless of your position in a company, they can be immensely valuable to CEOs, as the nature of their role leaves them without a manager to mentor them. If you're calling the shots on whether you or someone on your team gets a coach, think about it as an investment, not a one-time cost. Growth necessitates a trail of trials--you must always be starting over, learning new things, and true mastery requires the wisdom of knowing that nothing can ever be truly mastered. In addition to acting as a mirror for you to see who you are and the path to becoming the person you need to grow into, coaches can help soften and shorten the cycles of repeatedly being bad at things. --- ### Renovate Your Inner Self Through Journaling *Published: 2019-03-09* > "Become who you are by learning who you are." -- Pindar In editions [four](https://www.holloway.com/s/good-work-edition-004) and [five](https://www.holloway.com/s/good-work-edition-005) of Good Work, I wrote about the importance of asking ourselves what we're optimizing for. It's painfully easy to stumble around in life without pausing to reflect on whether we're pointed in the right direction, and there's endless pressure to point ourselves off The Cliffs of Workaholism and The Pits of "Oh My God This is *Not* Where I Thought I'd Be By Now." Tools for figuring out what we're optimizing for and whether that's what we want are about as abundant as tools for physical fitness, but this week I'd like to explore one close to my heart: journaling. Journaling is my favorite tool for self-discovery. Journaling has helped me realize I need to get out of a toxic relationship and recognize the negative impact of poor life decisions like drinking too much or failing to exercise. Journaling is the reason why I've been able to repair relationship mistakes, both at work and away from the office. It's what led me to leave my last company, Mattermark, and start Holloway. To a lot of folks, journaling *sounds* great, but they give up quickly because well, it's a lot of work. Instead of thinking of journaling as something you'll do a few times and see the benefit, think of journaling like *exercise*. You're going to have to do this for a while before you start seeing gains, and you're going to have to do it regularly. You're going to feel uncomfortable, and you're going to feel like everyone else has it figured out. Remember, you're new to this, and there are tools out there for making journaling easier ([Day One](https://itunes.apple.com/us/app/day-one-journal/id1044867788?), [750 Words](https://750words.com/), [200 words a day](https://200wordsaday.com/), and [Jour](https://itunes.apple.com/us/app/jour-guided-journaling/id1439590239) are a few). Beyond these tools, I recommend everyone buy Julia Cameron's [*The Artist's Way*](https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252). You can take my word for it, or you can take the word of [*The New York Times*](https://www.nytimes.com/2019/02/02/style/julia-cameron-the-artists-way.html): "Julia Cameron invented the way people renovate the creative soul." Cameron prescribes several exercises in her book, but one of them is "morning pages," which involves writing three pages, stream of consciousness, every single morning. Stream of consciousness means you don't think about whether the writing is any good, you just open up your brain and put it on paper. I've done morning pages off and on for ten years now, and the first sentence is almost always silly. Here are a few real examples from my journal: > "I don't need to be writing for anyone else. How are you doing, man? I know you're struggling. You're happy, but you're struggling and that's hard to reconcile. It's been good to get back to work in San Francisco vs. running all over New York City and struggling to find internet." > "Calling this morning perfect is too much of an undeserved platitude. It's downright cruel, in fact. My dear friend, Gary, is my hangover. On time and deserved, Gary reminded me the finer nuance of how Saturday mornings are indeed for sleeping in, but they are most certainly not for sleeping through." > "I've got my goddam writing hat on tonight. There's this hilarious aside to that statement and no one else is in on the joke but me, so I'll do my best to cut you in on it." Morning pages don't necessarily have to be done in the morning, but you'll find they're great for cleaning out your mental pipes so you can get to the office with a clear head. After you write Morning Pages for a month or two, you begin to notice patterns in your writing. You write about the same people, the same insecurities, the same dreams. I found the exercise immensely more valuable when I restarted Morning Pages when I moved to Silicon Valley at twenty-two. The more I wrote, I began to pick up tricks. By twenty-six, I began Morning Pages with the prompt, "What are you avoiding writing about?" Another trick: "What's everything making you anxious right now?" Once you see your thoughts on a screen or on paper, something strange happens. Your thoughts are no longer swimming with each other in your head, they're somewhere else, somewhere for you to *deal with them*. I left my last company, Mattermark, after continuously asking myself, "Why does something feel *off* about work?" It took me months of journaling to get to the bottom of this, but get to the bottom of it I did. I asked myself, "What do I want?" And then I wrote down *everything* I wanted. With it there on the screen, I could see that I wasn't on the path to getting what I wanted. So I took a new path, one that journaling helped me find. --- ### A Non-Dystopian View of Work *Published: 2019-03-02* Last week, we wrote about the importance of looking within to answer the question, "What are you optimizing for?" In a delightful turn--and reason #2,573 why I love the internet--Medium featured a piece on its homepage this week, "We're Optimizing Ourselves to Death" by Zander Nethercutt. Here's what I love about Nethercutt's piece. When read alongside Neil Postman's [*Amusing Ourselves to Death*](https://www.amazon.com/Amusing-Ourselves-Death-Discourse-Business/dp/014303653X) (cartoon version by [Stuart McMillen here](https://twitter.com/stuart_mcmillen)), a new theory takes shape that neither George Orwell nor Aldous Huxley predicted. We don't live in Orwell's dystopia of banned books and thought crimes. And we don't live in Huxley's world where everybody is so addicted to Netflix and Fortnite that nobody bothers to work or participate in society. When we get home from work in Nethercutt's world, the real world, we're all so exhausted it's like we're living with perpetually strained brains. So we turn our brains off by watching Netflix, and in this way, our world rhymes with Huxley's. But where does the distinction between numbing ourselves with entertainment and putting our feet up after a hard day's work lie? [Robert Greene](https://twitter.com/RobertGreene), one of my favorite writers, did a podcast, "[Alive Time vs. Dead Time](https://fs.blog/robert-greene/)" in which he spoke plainly when asked about his schedule. He writes for three to four hours a day, then his brain is tired, and he enjoys "mindless tv." What I love about Greene here is that he doesn't posture or [virtue signal](https://en.wikipedia.org/wiki/Virtue_signalling) about the necessity of working ourselves to death. He works a relatively short day--does Good Work--and rests. While we're all busy living in Nethercutt's world, Greene's found a different way to live. I don't know Greene, but I have a hunch that he's proud of his work. In Huxley's world, I imagine we wouldn't be so proud of our work--entertainment would be less about rest and more about escape. Which leads me to two questions to end this week's newsletter. First, are you proud of the work you do at the end of the day? Second, is the time you spend after work--whether it's family, friends, Fortnite, whatever--worth the work? If the answers to both are yes, then you live in a world not of Orwell, Huxley, or Nethercutt. The one thing the worlds of Orwell, Huxley, and Nethercutt have in common is that I don't want to live in those worlds. I want to live in the fourth world. Next week, we'll talk about where to look within and share a few tools for figuring out who you are and what you want. Only when you've done that can you get down to business doing Good Work that's either worth hanging your brain up for or Good Work so good it turns your brain on when you get home. --- ### Looking Within *Published: 2019-02-24* > "True self-awareness remains in short supply. When I mentor on career, the first question I ask is what are you optimizing for?" > > Sachin Rekhi, [Twitter](https://twitter.com/sachinrekhi/status/1099432766242865152) Answers to what we're optimizing for can be troublesome. They're often not even the real answers. "I want to move to New York City" can really mean, "I want to work with people who challenge me to think in new ways." "I want to start a company" can really mean, "I don't want to work for my boss anymore." In their book, [*Designing Your Life*](https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321), Bill Burnett and Dave Evans talk about the importance of finding your "north star." The phrase is a bit too Disney for me, but I like the distinction that a north star is something you optimize for over decades whereas goals are stepping stones towards your north star. We're never optimizing for one thing, and these layers of wants, goals, and north stars interact with each other. Knowing what we're optimizing for can be the real challenge, and the most rewarding one to figure out. It might feel like a lot of work to look within, to ask uncomfortable questions, to find habits that keep you tuned in to what's important to you, but if we don't look within, we're likely to find ourselves bouncing around the world like a pinball hoping not to fall into the gutter. Whether you're starting a team, joining a team, or hiring onto a team, knowing what you're optimizing for will help you determine whether an opportunity is a fit or not, possibly saving you months or even years of time spent working on the wrong thing. So how do you figure any of this out? In the next two editions of Good Work, we'll share thoughts, ideas, and frameworks. Stay tuned. --- ### Ten Year Careers *Published: 2019-02-16* > "I love people who harness themselves, an ox to a heavy cart, who pull like water buffalo, with massive patience, who strain in the mud and the muck to move things forward, who do what has to be done, again and again." > > -- Marge Piercy, [To Be of Use](https://www.poetryfoundation.org/poems/57673/to-be-of-use) My favorite people are irrationally passionate. They're the ones who get to work getting things done and forego the temptation to stick to talk. These people don't spectate, they participate. Whether they're writers on fire about writing, dancers stoked about dancing, chefs who can't stop cooking, teachers teaching even when they aren't teaching, whatevers whatevering so strong you stop talking about the weather--these are my people. Getting good at something--strike that--getting *great* at something looks a lot more fun in the theaters than it is in practice. Naval Ravikant, CEO of AngelList, said, "It takes ten years to build a career in anything."[**\***](https://twitter.com/angellist/status/904917659828895744). Thankfully, universities and public education systems and parents teach this, and there is rich discussion and so many helpful examples of how a ten-year career develops. Except they don't, and no there aren't. But what if? Having only one ten-year career under my belt, I'm no expert, but that shouldn't keep someone from trying. As far as I can see, here's how it works. In years one through three of a career in a given field, plus or minus a few months on either side, everyone is navigating what Chris Dixon calls "[The Idea Maze](http://cdixon.org/2013/08/04/the-idea-maze/)." Dixon's framing is specific to entrepreneurs, but I think the metaphor works generally. Before you can be successful in a space, be it acting, dancing, entrepreneuring, or whatevering, you have to know what's been done before--what's worked, what hasn't, what's been tried, what hasn't? In years three through seven, you've gotten to know the territory. You know the people's names who are people whose names need to be known, and you're trying things that have never been done. The thing about this phase is that things that haven't been done have a habit of being things that don't work. We love calling these things failures or, if you're a millennial like me, "learning experiences." In his book [*Mastery*](https://www.amazon.com/Mastery-Robert-Greene/dp/014312417X/), Robert Greene writes of the greatest dangers to achieving mastery in our careers: "feelings of boredom, impatience, fear, and confusion." A lot of people quit a career here. The last third of a ten year career is where things get fun. You don't just have context, you have experience. Your subconscious is trained and you get more comfortable with your intuition. You've fostered relationships for years, and they starting to pay off in ways you could never have expected. Progress plainly demands patience. But ten years is the minimum investment required for a career. After ten years, you can keep going, or even switch tracks. Take Bob Metcalfe, for example, the man who invented Ethernet--he's on his [fifth](http://www.weareaustintech.com/bob-metcalfe/) ten-year career. --- ### On Confidence *Published: 2019-01-02* I doubt myself a lot. "[Everyone is totally just winging it, all the time](https://www.theguardian.com/news/oliver-burkeman-s-blog/2014/may/21/everyone-is-totally-just-winging-it)" is one of my favorite articles ever. It makes me feel far less alone with my fears. Will my company be successful? Am I nuts? Are all my friends avoiding the trouble of telling me I'm working on bullshit? What if we're wrong about everything and this thing fails? Am I smart enough, good-looking enough, good whatever enough to find the kind of person I think I want to share my life with? Is it okay to end sentences with prepositions? I struggle to trust myself when making decisions at work. In different scenarios, I can be quick to jump to a conclusion, trust my gut, and end up taking on unnecessary risk. I also overthink a lot of decisions. My investors have characterized me as "academic." I know there's a [Goldilocks' Zone](https://en.wikipedia.org/wiki/Circumstellar_habitable_zone) in the middle, but I struggle to find it over and over again. I want to trust my gut, but I don't want to make a poor decision. I want to make decisions quickly, but I want to make *the right* ones. The fact that I both over-think and jump to conclusions in different scenarios makes this even more complicated, as there isn't a single solution. This year, I've learned that my gut is a great early warning system that I then need to verify to make sure I'm not just indulging in confirmation casserole. I like to think that I think for myself. I'm pretty sure I barely think for myself. If anything, I know I'm good at taking in a bunch of ideas and blending them up into something different from its constituent parts. But way too often, I find myself thinking about what other people will think if I do this or that. At the beginning of the year, I discovered the ["know yourself" cards](https://www.theschooloflife.com/shop/us/know-yourself-prompt-cards/) from The School of Life. One asked, "what are you trying to say through your clothes?" I spent a lot of my 20's trying to be someone I wasn't. I'd wear button-down oxfords because I was nervous about other people thinking I was too young. In reality, *I thought I was too young*. The "grown-up" clothes were for me, not for anyone else. They were a band-aid on a much larger self-confidence issue. In the late summer and early fall, I read [The Courage to Be Disliked](https://amzn.to/2oXHz1G). I struggle with some of the ideas in the book, like Adler's wholesale rejection of trauma, but this book helped me realize how often I and others around me live their lives on others terms. So often, we do what we think will please others. Whether it's because we desperately want to be accepted by a social group, break into a new social class, or something else, we spend *a lot* of time thinking about what others think of us. When we let others' views of us dictate the choices we make, we relinquish the agency we so convincingly pretend to cherish. I graduated from Ohio State. It's a state school known mostly for football, parties, and the immense size of the student body (40K+). I graduated with something close to a 3.14. I was especially proud of that. When I got to Silicon Valley, someone who will remain nameless was a total prick to me and said he was shocked anyone was considering hiring me considering I didn't graduate from an ivy league school. I've always hated that bastard. A few years later, Harvard Business School did a case study on Mattermark and gave us a mug as a souvenir. That's my favorite mug. I have a complicated relationship with that mug. At once, I'm proud of it, but I also hate that I get satisfaction from the external validation. It feels dirty. The combination of enough temporal distance from Mattermark and all the juicy goodness I've been learning building Holloway left me feeling a sense of shame late in the year. How could we have been so ignorant? Maybe I'm not exceptional. Maybe I'm destined to work in middle management somewhere. Maybe I'm destined for the misery I see painted on so many other people's faces. Maybe their misery is really my misery and it's unfair as hell for me to go painting without permission. I felt ashamed we hadn't been able to make Mattermark work. We had the bull by the horns, and we just let it trample us. That's what it felt like. Instead of valuing all that I had learned from founding Mattermark at 23, I let it eat at me. I let it eat at me because I looked at others who started companies in the same period who succeeded and I envied them, poor little me, starting over again. Toward the end of the year, I began to look at my experience building Mattermark like a series of mistakes I now think I know how to avoid. But then there's the specter of my self-confidence again: do I really know how to avoid those mistakes? Here's what I do know. I want to build a business that does some goddam good in the world. I want that more than anything in the world. I want to prove that people can organize to Get Something Done That Matters. What capital M Matters? Giving people tools to turn their brains on instead of off. That's something I love. I know I'm not alone in doubting myself. I know it's a journey. I know I am my harshest critic. That's a trope, but I can be a real asshole when it comes to treating myself how I'd like to be treated. So that's what this whole end-of-2018, Happy 2019, by the way, reflection is about. I've been diving into the lake of my self. Knowing my instincts are a good early warning system, I'm asking myself what's holding me back. What am I ashamed of that I need to get over. Why don't I believe in myself? How do I lead myself the way I'd like to see a leader lead, instead of harshness. A friend told me this year, "You have the ability to radiate light on someone when you're with them, but you haven't figured out how to focus it yet." What a compliment. But this year, maybe I need to learn how to focus that light on treating myself well. Maybe that's where I'll find the strength to be more [confident, farseeing, capable, and prudent](https://vimeo.com/2822787). --- ### Failure, Depression, and Yoda *Published: 2016-09-20* Isaac Asimov wrote a book called *The End of Eternity*. It's a great science fiction novel about a world where time travel is constantly used to change history in order to eliminate catastrophes. The society Asimov created, called "Eternity," essentially rooted out failures. I think this passage is particularly relevant to failure, pain, and depression: > "In ironing out the disasters of Reality, Eternity rules out the triumphs as well. It is in meeting the great tests that mankind can most successfully rise to great heights. Out of danger and restless insecurity comes the force that pushes mankind to newer and loftier conquests. > > Can you understand that? Can you understand that in averting the pitfalls and miseries that beset man, Eternity prevents men from finding their own bitter and better solutions, the real solutions that come from conquering difficulty, not avoiding it?" In December of 2011, I was living in the Short North in Columbus, Ohio. I graduated from Ohio State about seven months earlier and was working for a company called Duet Health. I spent my college career avoiding classes in favor of side projects like home brewing beer, designing iPhone apps, and learning about what it took to start a company. After less than a year in the workforce I was antsy to start my own thing again. After a Startup Weekend, a mentor of mine threw an idea out to me. He had been arbitraging Facebook ads, it was working, but he didn't have time to work on it anymore. He suggested I run with the idea. It was fairly straightforward: build landing pages for hotly anticipated consumer goods that have yet to be released (the next Call of Duty for example), target that product's Facebook Page, run ads, and then have links to pre-order the products on each page. We would take an affiliate fee. We would eventually call it LaunchGram. I convinced a couple friends of mine to join up with me on the side. We got into an accelerator in Columbus that didn't take any equity at the time, and we started spending a lot more time on the thing. We eventually decided to pack our bags and move the operation to the Bay Area, startup Mecca. It wasn't long after we arrived in Mountain View that we realized Facebook ads had gotten more expensive. Our advertising arbitrage opportunity was gone. So here we were in Mountain View without a distribution plan. We came up with a couple ideas, and one was good enough to get us into 500 Startups right when we were running on fumes. We celebrated getting into 500 Startups in the Fall of 2012, but after two months in the accelerator I knew we were dead. Not having any money wasn't as much of a sign of failure to me as it should have been. I spent the better part of the year with a couple hundred dollars in my bank account and several thousand more racked up on credit cards. Up until late November 2012 though, I had found a way to scrape together a bit more cash each month to keep going. I was pitching a lot of investors on LaunchGram, and I started to find myself agreeing with their conclusions that this business wasn't either very big or very viable. I had a sick feeling in my stomach every time someone asked me what I did. *I started to lie to people at bars or on the train when they asked me what I did. I didn't want to talk about my startup, because I knew it didn't make a ton of sense.* Over Thanksgiving I did a lot of soul searching. Not only was this business not working for a usage standpoint, I didn't care about the problem. Did the world *really* need a better infrastructure for product promotion leading up to a launch? Was that something that would *actually* make the world better? Was it something I *actually* wanted to be spending my time on? No. Looking back, I was lying to myself about being interested in LaunchGram. I came back from Thanksgiving and told my co-founders that we were out of money and the show was over. We had poured our hearts and souls into this thing, and it was done now. I held my feelings of failure close to my chest leading up to the conversation, and it came as more of a surprise to Zach and Carrie than it should have. I was pretty lost after this. I didn't think I was good at *anything*, and I didn't know *what* I wanted to do. I had done some design, I had done some sales, I had done some product management, but I didn't have enough experience in any of these to land a good job. I wasn't even trying to find a job for a little while. There was this vacuum in my life; I had nothing to fill the vacuum LaunchGram's failure had created. I couldn't come to terms with the idea of not running my own thing anymore. Worst of all, I didn't have any friends I could relate to with all of this. Carrie, Zach, and I remained friends, but things sucked for a while. I blamed myself for letting them down, and to a degree I still do. Along my journey of building LaunchGram, I periodically sent out update emails to people who had helped me out along the way. It was a list of family, friends, investors, and people whose input I valued. When I decided to shut down LaunchGram, I sent an email out to this list. The email reached one of my co-founder's family members before they had a chance to tell them what had happened. Another screw up. I didn't even know how to fail. Several great things came from that email though. About fifteen minutes after I sent that email, an acquaintance named Joel, someone I had only ever met twice, called me. I didn't even have his phone number. The first thing he said to me was, "Are you okay?" I was both appreciative of the call and confused. My failure was still fresh... but I was still in denial of how hard the next few months would be. I thanked him for the call and assured him I was okay. I wasn't okay. When I saw my friends, I told them things were great, I was finding the next thing! That, of course, was a big ol' pinocchio lie. I stayed home, played video games, half-heartedly searched for a job, and was trying to teach myself CSS. I needed do build something. There were days I sat in front of my text-editor all day, making progress, feeling strong. The next day I would interview, fail to find anything compelling, and feel hollow. A mentor mine named Christian Long also responded to my email. He still lives here in Columbus. He said: > "As Yoda reminds: '[Do or do not. There is no try.](https://www.youtube.com/watch?v=BQ4yd2W50No)' But, just as importantly, he only tells Luke, a Jedi in training. That's the key. > BE humble now. > > As you are. > > Be passionate. > > As you've elected to be. > > Be willing to trust the way forward. > > Again, as you are." "Do or do not. There is no try." This email meant so much to me. I wasn't looking for sympathy, and this was not that. It was support; it was encouragement. It helped me realize that *failure is something that happens when you set out on adventures*. I pictured Luke on Dagobah with Yoda. I knew the path ahead of me wouldn't be easy, but Christian helped me see that there *was* a path ahead. One night in January of 2013, I had less than $20 to my name. An entrepreneur named Dan Martell had invited me to a dinner with 10+ other founders, and I deluded myself into thinking I belonged there. It was my last hurrah before I packed my shit up and asked my Mom and Dad if I could come back home. I spent $7 on the Caltrain to get to San Francisco from Mountain View. My friend Danielle Morrill happened to be at this dinner. Everyone at dinner was ordering ~$30 dinners (standard fare), but I didn't have $30. I ordered *a beer* and manufactured some self-confidence. After dinner, Danielle approached me and asked me if I was all right. I told her that I was great, but she noticed I only ordered a single beer and didn't eat at an event where people were feasting and having a blast. That's usually my queue to have more than a single beer. Danielle called me out, *"You're broke aren't you?"* I'm not sure how you respond to that, but I'm pretty sure I just eloquently said, *"ugghghghhghg blarghhhhhhhh yeaaaaaaah I'm broke."* I was legitimately planning my quiet escape plan from California. That night, Danielle and Kevin cooked me one of the most meaningful meals of my life: grilled cheese, tomato soup, and a couple cold beers. At the time, I wasn't even comfortable telling my co-founders, Zach and Carrie, how terrified and depressed I was. Danielle and Kevin didn't offer me a job that night, but they did loan me some confidence to get back on my feet. Danielle did something pretty great that night. Instead of assuming I'd go get a job at a startup or move home, Danielle asked me what I was going to start next. I thought I was a failure as a founder, but Danielle believed I'd just start something else. Before this dinner, I thought I would be calling my Dad the next morning to explain to him how I needed to move back in with them for the first time in five years because I failed and was broke. Instead, I called my Dad the next day and asked him to stake me for two more months in the Bay Area. I told him that I believed that I could figure something out in two months, starting something new, getting a job a startup, *anything*. My Dad staked me. In twenty four hours, two people I looked up to for mentorship on this crazy ride as a founder chose to take a bet on me. About a week later, I was depressed again. Before this time in my life, I used the word "depressed" pretty lightly. Now I think I understand what it means to actually be depressed. I let my friends down, I wasn't good at anything, I was down on everything. I started crying at silly things. I knew something was wrong and that I needed to get back on my horse, but I didn't know how. I was taking the Caltrain into San Francisco from Mountain View a lot, and for those of you who don't know, somebody jumps in front of the train at least once a month. I was on the train three months in a row when this happened. The train stops and you're stuck for an extra thirty minutes to an hour. One time, after the train started to pull away, I was looking out the window and saw the aftermath. I saw the body bag...only a few yards from the Palo Alto Caltrain station. I already wasn't having a good day, but I started to wonder who these people were. I wondered if I would be one of those people in a few months if I didn't get my life figured out. I never got past that point. I never *seriously* considered physically destroying myself, but just thinking about it terrified me. I had to get control over my life. See, running my own company, whether it's going well or not, was like a *really good drug*, and I was going through withdrawal. There was a void in my life that I just couldn't fill no matter how hard I tried. It was like someone important in my life had died and I couldn't bear their absence. Except in this case, the person was part of me. I was nearing the end of my two months, and moving to suburban Philadelphia was looking more and more real every day. I started to understand why Joel called me and asked me if I was okay. Over the next month and a half, I got a couple great opportunities, but nothing really *spoke* to me. I felt like I'd be making the same mistake I made when I started a company and didn't care about the problem. One thing was for sure, being on Dagobah sucked. Then one morning, Danielle texted me saying she'd like to "buy my company." I didn't know what that really meant, but I drove up to San Francisco immediately to get coffee with her. We talked about how LaunchGram and Referly could be a good fit together, but I knew that Danielle was losing faith in Referly. We talked about other startup ideas, and she offered me a sum of money to come join her and Kevin. What I would do wasn't clear, but I knew that I respected these people, and working with them could not be bad. I took the deal. Two weeks later, Danielle and Kevin decided to let everyone go at Referly, but they asked me to stay to help create the next thing. Danielle had raised $1.2M for Referly, and we had about half of that left... to do basically whatever we wanted. While Danielle wasn't "closing the company down," she was giving up a product she had worked tirelessly on for more than a year. I saw her going through the same things I had gone through, just on a four-month delayed schedule. We didn't know what we were doing for a while, and figuring out what to do is a different story. Through the early days of what would become [Mattermark](https://medium.com/u/40233f4ee393?source=post_page-----2116ce56234e--------------------------------), I still felt like shit. Sometimes I wondered whether I was a washed up entrepreneur screwing around with two other washed up entrepreneurs. Maybe that was true, but as we settled on something interesting to work on, I started to feel a whole lot better. Getting above "pre-LaunchGram parity," though took me almost two years, but I did get back on my feet. I got more than back on my feet. Whether I "beat depression" or just plain got back on my horse, I ended up humbled and unafraid. Tim Ferriss said, "If we let the storms pass and choose to reflect, we come out better than ever." It echoes Asimov's, "Out of danger and restless insecurity comes the force that pushes mankind to newer and loftier conquests." People will tell you that failure is a risk you take when you set out on an adventure, but what they don't tell you is that failure can be a gift. It is a rewarding experience despite how painful it can be. About a year later, when I got an email from a founder that looked a lot like the one I sent when I closed my company down, I understood. I gave him a call just like Joel had called me. I got his voicemail, so instead I opted to send him an email. I said, *"As Yoda reminds: 'Do or do not. There is no try.' But, just as importantly, he only tells Luke, a Jedi in training. That's the key."* --- ### What Does a Startup COO Actually Do? *Published: 2015-07-15* Titles shouldn't matter, but unfortunately everyone has to have one -- including me. Today, I am the COO at [Mattermark](https://medium.com/u/40233f4ee393?source=post_page-----bbeb0f8648ee----------------------). The only consensus on what a COO does is that there is no consensus, especially at startups (see articles at the bottom). The role varies from company to company, some don't have the role, and the jury is out on whether startups need one. I believe the job of a founding COO is to do the most important things the company hasn't hired for yet, hire or delegate to someone in your place, and move on. Founding COOs need to be zero-to-one people who are good at and comfortable with firing themselves. ![The founding COO role: the intersection of things the company needs done and things you can take from 0 to 1](/images/essays/coo-diagram-1.png) ## How my role as COO evolved I wasn't always the COO. Mattermark is the same legal entity as Referly, but as Danielle says, "[Mattermark wasn't a pivot](https://medium.com/@DanielleMorrill/mattermark-wasnt-a-pivot-883efd58d65)." I was not a co-founder of Referly. [Danielle](https://medium.com/u/27d13727d627?source=post_page-----bbeb0f8648ee----------------------) and Kevin actually hired me after I [shut down my startup](http://andysparks.co/Losing-a-Battle-and-Focusing-on-Winning-the-War), LaunchGram. I was an individual contributor hired when Referly was gasping for air, and my job description was essentially, "go on missions for Danielle." I remember the lunch where Danielle told me she and Kevin had decided to shut down Referly, and I wasn't totally sure I had a place in their post-Referly company. Danielle explained to me that they had no idea what they would do next, but that I was welcome to join them and continue going on missions. So that's what I did, and it's not that different from what I do now. When we started Mattermark, Danielle blogged a ton and talked to potential investors, I hand-gathered a boatload of data, and Kevin helped me turn my process into software. We were a blogger, a guy [doing things that don't scale](http://paulgraham.com/ds.html), and a software engineer. When we were on the eve of launching Mattermark, I had a bit of an epiphany. I asked Danielle and Kevin, "Am I a co-founder of this new thing? Because I feel like one." They reassured me I was. Going forward, Danielle was our CEO, Kevin was our CTO, and I didn't really feel a need to have a title more defined than "Co-Founder." ## Mission #1: Start our data team In the early days we got our data by hand. We had an advantage over incumbents and later up-and-comers because we were willing to do work that didn't scale to deliver value for our customers. So the first team we built at Mattermark was a team of data analysts who filled a forest of spreadsheets with data on companies in VC firm portfolios. I led this team in my first functional owner role, and we decided to change my title to "Head of Research & Data." ![Mattermark research spreadsheet tracking company data](/images/essays/coo-diagram-2.png) As we built repeatable processes to get certain data points -- we call it the "human algorithm" -- we realized I had taken the team from 0-1. It was time to hire a much more qualified Head of Data. ## Mission #2: Figure out sales In January 2014, we had just tried to raise our Series A, and got feedback that we needed to prove out some other customer segments. Our sales were entirely inbound at the time, and we were getting a lot of non-VC customers signing up from investment bankers to salespeople to real estate brokers. I set out to (1) increase revenue and (2) determine whether we were actually ready to sell to any of these other segments. I was good at this mission, but I didn't want to do eight demos a day and carry a quota forever. This was hard both for me and the company. By firing myself from sales, I was essentially firing one of our most productive sales reps. ***Takeaway:*** *As a founding COO, you will have to pinch hit and do things you don't like. Eventually you have to find someone else to do those things though, or you'll burn out.* Early on in my second mission, at one of our company all-hands meetings, I remember when one of our engineers asked, "Andy, I know you're working really hard, but what is it that you do?" We all laughed, and I explained the things I had been working on. ![What would you say you do here?](/images/essays/coo-diagram-3.gif) I felt like an [imposter](https://en.wikipedia.org/wiki/Impostor_syndrome) though, because my latest mission was as an individual contributor. Co-founders are supposed to manage teams and run the business, right? I believed I had to directly manage people to be a leader. I was asking myself what I was going to lead. Ultimately, I knew an opportunity would present itself and that as long as I focused on driving value for our customers and our business, I was in the right place. ***Takeaway:*** *Changing roles often is hard enough for the person doing it, but it can be confusing to the rest of the team. Make sure to clearly articulate your new responsibilities.* ## Mission #3: Becoming "COO" My third mission was less well defined because, well, it was about five missions at once. This fall, we needed to get a new office, figure out recruiting, start a customer support & success team, and turn our startup into a professionally managed company (see legal, accounting, HR, and all the fun stuff). ![Juggling too many things at once](/images/essays/coo-diagram-4.png) At this time, I had the choice to go with "VP of Facilities, Recruiting, Customer Support & Success, Finance, & HR," or something more catch-all like COO. One of our investors offered a third option, "VP of Shit." I decided to go with COO. ## The Future In 2015, we hired an outstanding Customer Success Manager, Manali Karmarkar. That team is running like greased lightning now. We moved away from a centralized recruiting function with internal recruiters to a model that distributes the load amongst hiring managers. Finally, we hired a VP of Finance, Emad Khan, to take over finance, HR, and facilities. Keith Rabois says "you're constantly fixing things," which you are. You are also constantly solving problems you haven't solved before. Problem solving in an ambiguous environment should be a founding COO's core skill. **Going forward, my job will be the same as it's always been: find the most important things the company hasn't hired for yet, hire or delegate to someone in my place, and move on.** ## Further Reading on COOs 1. ["The 'other' company founder"](http://finance.fortune.cnn.com/2013/09/10/the-other-company-founder/) by Jeff Bussgang of Flybridge Capital Partners 2. ["Keith Rabois on the Role of a COO, How to Hire and Why Transparency Matters"](http://firstround.com/review/Keith-Rabois-on-the-role-of-a-COO-how-to-hire-and-why-transparency-matters/) on First Round Review 3. ["I Don't Believe in COOs"](http://www.feld.com/archives/2008/03/i-dont-believe-in-coos.html) by Brad Feld of Foundry Group (this one is particularly funny because Brad is on our board) 4. ["How my co-founder and I structure ourselves as CEO and COO"](http://joel.is/post/81224573728/how-my-co-founder-and-i-structure-ourselves-as-ceo-and) by Joel Gascoigne of Buffer 5. ["Should You Hire a COO"](http://blog.eladgil.com/2013/02/should-you-hire-coo.html) by Elad Gil 6. ["Second in Command: The Misunderstood Role of the Chief Operating Officer"](https://hbr.org/2006/05/second-in-command-the-misunderstood-role-of-the-chief-operating-officer/ar/1) by Nathan Bennet and Stephen A. Miles at Harvard Business Review 7. ["Why Your Startup Doesn't Need a COO"](http://www.bothsidesofthetable.com/2011/09/12/why-your-startup-doesnt-need-a-coo/) by Mark Suster of Upfront Ventures 8. ["Even startups need a COO"](http://venturebeat.com/2011/05/26/even-start-ups-need-a-coo/) by Firas Raouf of OpenView Ventures 9. [What are the characteristics of a good COO (chief operating officer)?](https://www.quora.com/Leadership/What-are-the-characteristics-of-a-good-COO-chief-operating-officer) on Quora 10. ["Do startups need a COO?"](https://www.quora.com/Do-startups-need-a-COO) on Quora 11. ["What makes a great COO"](https://www.quora.com/Startups/What-makes-a-great-COO) on Quora 12. ["What is the difference between CEO and COO?"](https://www.quora.com/What-is-the-difference-between-CEO-and-COO) on Quora 13. ["The Scale-up COO"](http://norrisnode.com/the-scale-up-coo/) by David Norris of Forward Partners --- ## Links - Homepage: https://andysparks.co - Coaching: https://andysparks.co/coaching - About: https://andysparks.co/about - Essays: https://andysparks.co/essays - Contact: https://andysparks.co/contact - Management Craft: https://managementcraft.co - LinkedIn: https://www.linkedin.com/in/andyjsparks/ - X/Twitter: https://x.com/andysparks