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Losing a Battle, and Focusing on Winning the War — Part IV: Recovery
Once I realized the jig was up, it was time to tell my team, pick up the pieces, and figure out what else I was going to do with my life now that LaunchGram was over.
Telling my team was no small task. In fact, I think it was the scariest part of the whole thing. I was afraid I’d lose my friends. Not only did I want to prevent that from happening, I wanted to make sure create the best outcome possible for everybody. It was my responsibility to make the transition out as smooth as possible.
Closing down a company is a lot like a breakup. Sometimes the circumstances dictate that you can be friends, other times they don’t. I remember getting lunch with my mentor, Christian, a month or so ago when I was in the thick of this decision. He told me, “When the nights get hard, double down on the people in your life.” So that’s what I did. I doubled down and focused on turning my co-founders back into friends.
I wanted to wait until after New Years’ Eve so everybody could enjoy their holiday, but after who knows how many glasses of champagne, vodka and whatevers, and a few PBRs, the emotional side of me came out and spilled some of my conclusion with my co-founders. I could have handled that better.
I took each of them on a walk the next day to talk about next steps. Everybody knew it was coming to a degree, and there was an odd sense of peace mixed with turbulence in the air that’s hard to describe. We were simultaneously afraid, but confident we’d figure things out.
Throughout the whole process, I had a number of off-the-charts incredible mentors, advisors, and friends who helped me through the process. Despite feeling awfully alone at times, I was tremendously lucky to be surrounded by support. Each individual had a [very] different opinion on what to do, but at the end of the day it was up to me to make the call (see: Feedback Fatigue).
After the decision was final and I slowly filled each of these people in, a couple even offered temporary employment as a bridge to help us figure out what sort of future we intended to build. To those of you - you know who you are - thank you.
When a dam breaks, the village below does not simply stand up and rebuild. It takes time, and the village is really never the same afterward; some things are broken. Similarly, when you lose a battle, you come out on the other side changed. There’s a tendency to come out with a higher aversion towards risk and there’s a high likelihood you’ll feel lost. I sure did. But I also came out stronger and smarter - able to read the battlefield and see things coming before they hit.
That said, I questioned what my role in the business world was: was I a product guy, a marketing guy, a sales guy, or something else? For so long, I had identified with being a founder who wore many hats, some of which fit better than others.
Then I remembered the beauty of The Avett Brothers’ line, “Decide what to be and go be it.”
The beauty is that you don’t get to decide what to be just once. You have to repeatedly revisit the act of deciding what to be over and over again. If you’re really going to do what you love, you have to be vigilant in making sure you know what you love doing each day.
I saw a TEDx talk in Washington D.C. a few years back that talked about this idea. The speaker called it, “prototyping your life,” as a way of figuring out what you’d like to be so you can get on with being that.
In his recent NYT bestseller, The Social Animal (which I HIGHLY recommend), David Brooks said,
“the truth is life is about producing failure. We only progress through a series of regulated errors. Every move is a partial failure to be corrected by the next one.”
Losing the battle with LaunchGram was a “regulated error.” I’ve emerged battle-hardened, entirely more mature and significantly humbled, but not knocked down.
What I really learned is that life isn’t about fighting one battle. It isn’t about throwing one big hail mary pass. It’s about a series of focused and purposeful battles. It’s about knowing each battle is part of a larger war to achieve whatever it is you want to achieve.
“Deciding what to be,” “doing what you love and doing it more often,” and “enjoying your work,” are all things worth fighting for, but fighting is hard. It’s emotionally draining, and it’s even painful at times.
But it’s possible. You just have to fight. And people only win battles when they’re fighting for what they love.
So fight the battles, because the war is waging, and it’s one worth fighting for. It’s a war for a better future and after all, the future is ours.
Losing a Battle, and Focusing on Winning the War — Part III: Panic
Around Thanksgiving I panicked, and I don’t panic often.
I decided to spill my guts to my Dad, who I’m lucky enough to be able to count as both a mentor and a friend. He helped me realize I had two options: close it down, or double down and give it another shot. I convinced myself afterwards that I was just hallucinating, I would go back and set some goals for numbers, and we’d figure this thing out.
But as I said in my last post, doubt is the disease of the determined, and now it had infiltrated my confidence on too deep of a level. I expressed my concern to a mentor, and was advised to bury it, put it back behind the dam, or at least to make sure my co-founders didn’t smell my fear. Keep it to yourself lest the disease shall spread, I was advised, at least until I was sure.
Loneliness doesn’t begin to describe what I was feeling. My two best friends, the people I needed the most, were the ones I couldn’t talk to.
It was somewhere around this time that a good friend from my past sent me a message saying that he had quit his job that he hated, found one he loved, and finally felt confident to talk to me again. I was completely perplexed. This was a guy I’d pick up the phone for at 4am, despite having not seen in a couple years, and he was telling me that “since I was doing what I loved, he felt embarrassed.”
It was life’s ultimate ironic sucker punch because I was going through mental and physical agony. Sleep was basically a cruel joke I taunted myself with by telling myself I was in control of it. I kept up appearances and told everyone I was fine. If men don’t cry, CEOs definitely don’t. At one point, I would even go into my room and turn off the lights after a certain point in the night just to convince my co-founders I wasn’t an insomniac who was about to break down.
One day before Christmas, I decided to take a step back from the whole picture. I asked myself, “If you could be doing anything, regardless of money or time, would it be this?” I had asked myself this question before, but then the answer was no on both counts, and I really panicked.
All of a sudden, every single doubt, every single tiny inclination towards this being the wrong battle to be in just rushed in. It felt like I was getting waterboarded by negativity, fear, and self-doubt. The dam just utterly collapsed.
I wanted to cry, but out of some stupid BS macho ego mindset, I just couldn’t. I felt empty, exhausted, and isolated.
I tried to make sense of it all. I tried to pick up the pieces and see if I could salvage the company, the product, and the team. Not only did all doubt permeate my every thought, all the people I would let down rushed crippled me from making decisions and having important conversations. Previously this fear of letting down my peers, parents, mentors, advisors, investors, and friends were hidden behind the dam under the pretense that I was going to succeed and damn anybody who said otherwise.
I realized that I had investors. I had co-founders who were best friends who I’d be letting down. I had put my life-savings into this company. That was supposed to be a down payment on a house. My friends moved across the country for this. I sacrificed some really great relationships for this. My Mom and Dad told their friends and my Grandparents I was successful - some “whiz-kid” in Silicon Valley - and somehow managed to become independent despite a generation plagued with a lack of direction. But really, I just felt like a fraud.
“What to do if you think your company is failing or going to fail,” is not a class Ohio State offered in their Entrepreneurship minor, so I sucked it up. I woke up the next morning, made coffee, and tried to hold it together.
Part IV: Recovery will be published tomorrow.
Losing a Battle, and Focusing on Winning the War — Part II: Distraction
Distraction is the enemy of progress and ambition. It happens when we take our eyes off the prize and start letting other people’s goals dictate our own. Distraction happens too often and it happens because we let it.
When I look back at LaunchGram and why I failed my team, my investors, and myself, I see a story with distraction at its source.
The honest truth is that I started LaunchGram not because I cared about movies, tv shows and video games coming out in the near future, but because a mentor threw out some statistics that lead me to believe that it could be a lucrative opportunity. I looked into the data on what was then a Facebook ad arbitrage system and it looked like we could print money.
Our Facebook ad arbitrage system got “Zucker-punched” when Facebook’s ad price increased. We should have seen this coming, but the fact is that we didn’t. It happened right when I had convinced my team to pack their bags and move from Ohio to Silicon Valley. We were in too deep to quit, so we had to find a way forward.
We hunkered down on building an alerts mechanism for video games, movies, and tv shows that aren’t out yet. We encountered competition. We hustled down relationships with phenomenal advisors, mentors, and now friends. We got our first investor with 500 Startups.
I started and built LaunchGram because I thought it was a lucrative opportunity - not because I deeply cared about the problem - and that started to become a problem.
When you’re an entrepreneur, you hear a massive amount of “no,” “that’s stupid,” “that will never work,” “you’re out of your mind,” “you’ll fail,” and other warnings reeking of risk-aversion. As a self-defence mechanism, you start to build a dam. You put all the things that make you afraid behind this dam because there is no other way to keep your enthusiasm.
Doubt is the disease of the determined, so you dam it up. That dam only works if you care about the problem you’re solving and believe you’re going to solve it.
Right around Thanksgiving, three investors told me that they liked me, but they just couldn’t invest in this idea. That was when I realized it was because I wasn’t emotionally invested in the idea. I was not fully engaged. I was distracted and they could see right through my manufactured confidence.
So the dam started to break.
Part III: Panic will be published tomorrow.
Losing a Battle, and Focusing on Winning the War — Part I
Ever since I was in the fourth grade I’ve been waging war. This war is about not settling for working in a coffee shop or a cubicle when you know you’re capable of more.
In Mrs. McKenzie’s fourth grade class, she asked us all to go home and ask our Dads what they would be if they could go back in time and do it again. It was an exercise for Father’s Day. I remember my Dad somberly admitted without hesitation that he’d go back and become a baseball pitcher. Instead, he did ops for a dot com.
That was the first time I can remember feeling incredible sympathy towards my Dad. If I had the words I have now, I think I would have said to him, “Damn. That is some real shit, Dad. Why didn’t you, then?” Right then and there, I was determined to have my answer to my son be, “I wouldn’t change a thing. Not a damned thing.”
Looking back, that poignant conversation with my Dad and the realization that I might live my whole life doing the wrong thing, has been motivating me to fight this war for the last fourteen years.
It turns out I’m not alone. This war is about a call to action like The Avett Brothers’ “Decide what to be and go be it,” and it’s about Holstee’s manifesto proclamation, “This is your life. Do what you love and do it often.” It’s about what a Reddit thread called, The New American Dream: “Doing what you love and trying to find a way to get paid doing it.”
It’s about not settling for working in a coffee shop or a cubicle when you know you’re capable of more.
Our war isn’t just a naive “no regrets,” battle-cry. Rather it is a generational and cultural shift away from realistic retirement plans and stable careers towards an environment rife with chaos. Flexibility is compulsory, manic economic conditions appear to be the rule rather than the exception, and education is not something that happens to you, it’s something you’re responsible for individually.
In war, the eventual victor doesn’t necessarily win all of the battles.
I fought two battles since graduating college and lost them both pretty miserably. The first of which was working for a mobile software startup in Columbus, Ohio (I went to Ohio State) while believing I could run the place. The second battle I lost was technically my second incorporated company (my first was a microbrewery at 19 and you can guess how that fared). I lost the second battle this month.
Not only did I lose it, I retreated. I surveyed the battlefield, considered my odds, and decided to live to fight another day. Writing that makes it sound like there was some kind of glory in it. There wasn’t. It’s a metaphor that not only makes me feel better about doing something hard and failing at it, it helps me understand this failure in the larger context of the war.
In October, we managed to hustle LaunchGram into 500 Startups. I started a weekly blog series to cover what the experience was like but I ended up stopping the series. It was a time suck and transparency is easy when things are going well, but doesn’t always make sense when things aren’t.
Somewhere in that series, I got a few tweets and emails asking for stories about the hard times and the worst times, because a lot of blog posts are about the good times and the best times. So, with that, I’ve decided to write a series while my latest failure is fresh.
I’ll publish three more posts in this series to cover (1) why it happened, (2) how it felt while it was happening, and (3) how I picked up the pieces and came out stronger.
It’s a story I haven’t taken lightly. When I set out to write it, I was doing it to share the experience with other founders & aspiring founders. After finishing it though, it has been deeply important in helping me understand the role of failure. So with that, this story is a bit self-serving, but I also truly believe it has the potential to be helpful to others.
Part II: Distraction will be published tomorrow.
Closing Down LaunchGram
There are certain things in life you absolutely dread doing, but the longer you put them off the more painful they get. This is one of those things.
Right after the first of the year, the team at LaunchGram made the final decision to close up shop. It was the hardest decision I’ve ever made.
For the short-term, the website will stay up, and we’ll be sure to let all of you know if that changes.
This post is decidedly and purposefully brief. On Monday, I’ll publish the first post in a four-part series, concluding on Thursday, explaining what happened, why we came to this decision, and how it felt going through it.
I didn’t sit down to write the series because I think anybody cares about what I have to say, but rather because I needed to work through the experience in words and because I hope that others can learn from what we’ve gone through.
This will be redundant, but I’d like to thank everybody from family, to friends, to advisors, to mentors, and to those of you that transcend those classifications for your support and advice throughout the process.
One thing I am sure of moving forward, is that whatever happens next is going to be one hell of a lot more exciting than what happened before.
So with that, I say I’d like to say a bittersweet farewell to LaunchGram, and welcome a new chapter of incredible possibilities and adventures.
Week 9: Opening Up to “More Open, Smart, and Honest Criticism”
I just read Semil Shah’s blog post on how the startup community needs “More Open, Smart, and Honest Criticism.” It really resonated with me.
We get a lot of this at 500 Startups from mentors, advisors, friends, and just about anybody, but I also know there’s a lot we don’t get. Just the other day I had a friend tell me that he wasn’t sure why he’d ever use LaunchGram. We’ve known each other for a few months, and it kind of bummed me out that he hadn’t felt comfortable enough to tell me this before, but I was grateful he had decided to come forward.
So I’d like to take this opportunity to open up LaunchGram to respectful, but open, smart, and honest criticism. Conversations between friends happen behind our backs (I’m 100% fine with this) and this is a great opportunity for people to let it loose.
CAVEAT: It’s easy to say, “That’s a dumb useless app,” but it’s hard to say, “here’s why, here’s where I think the team could drive value if they moved in a slightly different direction, and here’s how I’d be willing to help them if they did ___.”
Please either leave your criticism and feedback in the comments below, on Hacker News, or shoot me an email at firstname.lastname@example.org. I’m looking forward to it.
Week 5: Always Be Opening
This post is the fifth in a series titled “The Chronicles of 500: Weekly Essays on What I Learned from 500 Startups.” Andy is currently the CEO at LaunchGram.
In the 1992 film, Glengarry Glen Ross, Alec Baldwin delivered an absolutely epic sales speech. The speech leaves viewers unable to forget Baldwin’s point: “Always be closing!” But it isn’t just about closing. In order to close, you first have to open.
Good salespeople know that they always have to keep their ‘pipeline’ or ‘funnel’ full. A pipeline works by filling the top with as many people as possible, and then filtering them down to buyers. Adding people to the top is called ‘opening,’ and getting sales is called ‘closing.’
This isn’t just about sales though. When you’re starting a company, you need all kinds of funnels.
You need funnels of potential co-founders, investors, customers, and hires. They don’t all come at once, so you have to grind. This is what it means to build a network. As a CEO, “non-technical” founder, or businessperson, your technical skill is knowing a boatload of people.
A lot of the skills you need for each funnel overlap, but I’ve added a few notes and comments I think are important for each type below:
This is the earliest place entrepreneurs fail. They either don’t have developers, designers, and business development people in their back pocket to call on, or they have the wrong ones and things go all kinds of terrible.
Something I think business people forget a lot is that developers and designers make great friends, and great friends can turn into great co-founders, too.
The mistake I see the most with first time entrepreneurs, and one I’ve personally made, is waiting until they’re strapped for cash to start talking to investors. Mark Suster talks about how he invests in lines, not dots. The TL;DR (too long, didn’t read) is that investors don’t like to write a check after one meeting. They like to get to know you and see how you perform over time. That gives them the ability to make a more informed decision on how you’ll perform in the future.
In a recent book called, The Defining Decade: Why Your Twenties Matter, author Meg Jay calls this building “Identity Capital.” She describes it as, “the currency we use to metaphorically purchase jobs and relationships and other things we want.” In this case, every entrepreneur needs to be building “Identity Capital” with investors they’d like to get checks from well before they ask for them.
Customers are a lot like investors. You need to talk to as many of them as possible, as early as possible. Even if you aren’t ready to sell them something, get to know decision makers in your industry, gain their trust, and drink a beer with them. It’s the least you can do.
Another great point from Jay’s book is about what she calls “weak ties.” The gist is: “as we look for jobs or relationships or opportunities of any kind, it is the people we know the least well who will be the most transformative.”
It might not be immediately apparent to you why you should know advertising executives in New York City, the CTO of a large medical software company, or a CMO you ran into at a conference. Some time down the road, however, you might look back and wish you knew someone in some space. Avoid this; minimize your risk by building an extensive network early.
If you’re lucky enough to find yourself looking to hire additional employees, you’re going to need a large pool of talent to draw from. If you’re starting a web-based business, how many developers do you know that code in the language your product is built in? How many A-level sales guys in from your industry do you know? How many graphic and interaction designers do you source feedback on your product from?
Creating a company can be all-consuming, and it’s easy to find yourself buried and not socializing. Getting out and meeting people from different backgrounds and varied skill sets is vital to your ability to grow your team. Build out a diverse network of talented people, so when you need to hire, you can.
The ability to close is essential to professional growth; there’s no arguing that. But you need to make sure the co-founders you bring on, the investors you get into bed with, the customers you tie yourself to, and the employees you bring on to build with you are worth the effort. The only way to do that is to meet and get to know scores of people from a wide variety of backgrounds.
The only way to do that is to always be opening.
My buddy, Jason Evanish, recently wrote a blog post on “The Defining Decade: Why Your Twenties Matter” that took off on Hacker News. Read it here.
As for hiring, Mark Suster has several great posts I highly recommend here.
Week 4: Fear of Failure Prevents Minimal, but Necessary Time Off
This post is the fourth in a series titled “The Chronicles of 500: Weekly Essays on What I Learned from 500 Startups.” Andy is currently the CEO at LaunchGram.
When I sit down to write a blog post, I usually write down five or ten titles and then run with what strikes me. Today, I ended up with two conflicting titles: “Personal Life, What’s That?” and “Why Weekends are Important.” Contradictory titles? Yes. Accurate? Also yes.
How is that possible? Well, there’s an unspoken tension in early-stage startup land I’d like to talk about.
The first half of this tension comes from the fact that we’re all terrified that if we don’t work hard enough, our companies will die. I actually just saw a tweet from Chris Dumler today agreeing with something Sarah Lacy from PandoDaily recently said: “I wake up excited and terrified every day.”
The other half of the tension comes from our very real and human need to turn off and relax. I’m not talking “go on a three week vacation” kind of relaxing, though. I’m talking about the “take a weekend for yourself” kind of relaxing.
But we’re afraid to take a weekend for ourselves. I know I personally feel guilty on Sunday nights after I spent my Saturday with friends and my Sunday with a good book.
We’re afraid because if we fail, it will be because we weren’t working on that weekend and we’ll blame ourselves forever. So we end up working a good amount of weekends.
What if the opposite is true, though?
Relaxing is valuable. People come up with ideas in the shower because our brains need to turn off to process life. What if our unwillingness to take time to reflect, relax a bit, and take a step back from our company leads us to failure?
This is a back and forth issue. Some people think entrepreneurs don’t work hard enough, some people think they work too hard. Should we sacrifice our personal lives, and if so, for how long?
Finding a balance is obviously up to each entrepreneur. I’d love to hear from others, from all stages, in the comments section below.
Discuss below using the DISQUS comments, or comment on Hacker News here.
Also relative to this article: People Claiming to Work More Than 70 Hours a Week Are Totally Lying, Probably
Week 3: Feedback Fatigue
This post is the third in a series titled “The Chronicles of 500: Weekly Essays on What I Learned from 500 Startups.” Andy is currently the CEO at LaunchGram.
I ask all of our users and everybody I meet for feedback.
Having started 500 Startups three weeks ago, I’ve been talking to brilliant past and present founders about our product.
I’ve been getting a lot of feedback.
Design feedback, UX feedback, business model feedback, marketing strategy feedback, you name it, I’ve been getting it lately.
A lot of it has been from really smart people that I look up to. A lot of it has been insightful, well thought out feedback. A lot of it has been really terrible feedback that is uninformed.
As CEO, it is my job to swallow my pride and defer to users and experts’ insights, but it is also to trust my gut, defy the experts, and press on.
This can lead to feedback fatigue, which is when you feel that feedback stops being useful and becomes a distraction.
But feedback fatigue is good; it means you’re getting a healthy amount of feedback.
The key is that while you don’t have to take everybody’s advice, you do need to listen to as much of it as possible.
This will be exhausting and it will be obnoxious, but it will also be one of the most beneficial things you do for the growth of your product and business.
Discuss below using the DISQUS comments, or comment on Hacker News here.