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A few things I learned while starting a company

I had just come out of a bathroom when I see a girl with her phone out. It’s got my face on it. Was she a stalker? No, I’m not good looking enough for that. It’s my Tinder profile as we had matched earlier. She’s cute, so I do the sensible thing and ignore her. She comes up to me, anyway, and strikes up a conversation. We hit it off. I wasn’t ready to start working for somebody else yet, so we did the obvious and sane thing: we started a company.


I’m in love. We work in only the best cafes and meet people way more important than we are on the regular. The first paying customer makes us feel like we’re on cloud 9. It’s like crack if I knew what crack was like and we get addicted. A few months later, we had been covered by almost every national media outlet, we’re revenue positive, had a team of 6, things were looking hard but doable. The only detail: we had a competitor valued at 400M USD and personally, I don’t believe in losing. Losing is for losers.


I wake up to the loud roar of public transit busses outside my apartment window. The room is stupidly hot. I feel gross and angry. Who the heck put up the thermostat? With dry, dreary eyes, I look at my laptop. Crap, angry customers, again. Angry partners too. Everybody is angry. Everybody except for Janet (my cofounder and girlfriend). She’s just tired of the grind. For half a year she’s been saying the same 100 words over and over because it’s our sales pitch. My father calls me, my grandmother is sick. How sick can she be? I got no time for that, who is he to tell me what I should do, I have a company to run. Never mind that I’m staying in his apartment. We must hit those metrics, nothing else matters.


One of my teammate's father passes away. I’m still angry. I have to figure out how to align our partners with us and not our competitors. Our competitors have destroyed their partners businesses. We’re the good guys, we’re doing the right thing. Failure just isn’t an option.


My grandmother passes. Wait a second, I only got to see her twice before she passed. My mind starts spinning. I get sick 3 times in a month. I can’t wake up, I hate waking up. What’s the point in all of this? Do I believe in what we’re still doing? Yes, I still do.


I ended up leaving my team (who is still going strong). It’s been about half a year since I left Fitset (our venture). I can safely say that there has never been a period in my life where I’ve experienced such highs and such lows. While I wouldn’t argue that you should fail at a startup just to learn, it did end up being the single most humbling and greatest learning experience in my (not so long) life. Here are a few takeaways that I took with me and will probably have with me forever.


If you’re going to do something hard, answer why first
I’m spoiled because I’m an engineer. It’s a good time to be an engineer. I could go work for Google, or Facebook, or any of the high flying companies out there making good money, getting fed free food, and so on. It’s not because I’m smarter than anybody else (though I’d like to think I am), it’s because engineers are in demand.


That said, by starting a company, I have to rationalize to myself, day in, day out, that I’m willing to forgo that cushy life so I can work for free, with longer hours, putting out fires 24/7, answering to not just 1 boss, but all of our customers. Those customers, unlike bosses, aren’t accountable to anybody. They own you. If you and your products/services don’t make them the happiest people in the world, you have nothing. No money, no time, no product market fit, nothing. Starting companies can be really fun, but they can also be incredibly soul destroying. A 9-5 job, while it can be soul destroying, has nothing on being a startup founder.


To be able to go the distance, you need to have an answer to why. My answer was that I was going to solve a problem that I cared deeply about. A lot of people believe that’s the only “why” that you should really try to answer but I don’t really think that’s true. There are plenty of great entrepreneurs who love entrepreneurship for reasons other than that. That said, they all have an answer to why that is core to who they are.


Managing your psychology is really, really important
Startups have a way with playing with your emotions. You don’t get enough sleep, you have 1,000 existential threats to your business, your relationships suffer, etc. I went to bed every night curled up in a ball. Most (all?) of those things were all in my head and I made poor choices as a result. I neglected my family, I didn’t give myself time to decompress, I became angry all the time. Had I had the ability to mentally distance myself from the situation and consider objectively, what we needed to succeed, what was actually important to my life, etc. I’d probably still be working on Fitset. If you don’t have your mind, you can’t make good decisions, so managing that psychology is incredibly important and difficult.


Nothing is as bad as you think it is
You know what would have happened if Fitset went down? Nothing. I would still have had Janet, a supportive family, my health, a ton of learning, and a world of possibilities. You and I are born in one of the most magical times in the history of mankind. Call me naive, but never before has it possible to change the world with a little bit of effort and $20 to rent an AWS server. Today, I can write this post and have that work read across the world nearly instantaneously. That’s magic. That wasn’t possible a lifetime ago. I’m not dealing with hunger, I don’t have to fight a war, and I’m not sick. It’s hard not to care deeply about a mission and company that you’ve spent blood, sweat, and tears creating from nothing. But at the end of the day, I have absolutely no reason in the world not to be the happiest man in the world because I have a lot. When times are hard, it’s a beautiful thing to remember that.


Good decision making is a practiced skill like anything else
There’s plenty of room to make mistakes, founding a startup. But if you don’t make enough good ones, you don’t get paid, you don’t get to eat, and you get nothing. When the stakes are, in relative terms, high, you tend to want to make good decisions. That pressure has a way of getting you to make incorrect decisions because you stress about all of the things that don’t matter. “How are we going to scale?” “Do we have to take time off to raise funding?” “How can we get the word out?” Startups are horribly counter intuitive and while all of these questions have a time/place, they’re usually asked at the wrong times. You can understand this logically, but to feel the pain of making an incorrect decision is something else entirely. If anything, founding a startup forces you to think deeply about what questions you’re trying to answer because answering the wrong questions hurts. A lot.


Savor the wins
There are always reasons to be unhappy. I had a lot of them. I look back and think of all the things I could have been happy about. I wish I could have relived those moments. Our MVP launch. The feeling of having our first sale. The feeling of introducing a customer to something they can be passionate about and getting that feedback. Having fun with our partners and all the interesting experiments we could be running. Celebrating the launch of a new city. I always had such lofty, unrealistic expectations of myself and where I wanted Fitset to go that I missed out on some of the sweetest reasons to be happy. I still look back fondly. But I do wonder, sometimes, what life would be like if I had given the team, and myself, a bit more room to breathe. In the end, what’s it all for if not to enjoy the ride? You can try to be happy in the future (which may or may not exist) or you can be happy now.


Family first
There are many things you can sacrifice for a company. You can sacrifice your youth, your sanity, your health, your finances, but one thing you can never really get back is your family. Life is short and the time that you have with your family is finite. I had to lose my grandmother to learn that lesson. Nothing should ever come before your family.


It’s been half a year since I’ve left Fitset and I’m still digesting what exactly happened. Time has a way of flying by, especially in the first days of a company. If you’d have asked me if I’d have done it, knowing what I know know, the answer is probably, yes. I can't think of any other way I could have made as many mistakes as I did.

(An aside: Fitset is still going strong and I wish them the very best.)

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