Confessions of a 20-Something Startup CTO

bencoe:

Looking back through the commit history of attachments.me, I see that my first commit was made almost exactly two years ago. In this time, my co-founder Jesse and I have:

  • raised 2.5 million dollars.
  • convinced several awesome co-workers and advisors to join us on the journey.
  • built a product that we take pride in.

It’s been an emotional roller-coaster-ride:

The Highs are High

I recall the day we closed funding. Jesse and I hiked up into the hills surrounding San Francisco’s Mission District. We looked out over the city, ecstatic, these were literally our teenage dreams coming true.

The Lows are Low

I also recall walking down Valencia Street, tired as hell, running out of money, arguing viciously with Jesse (one of my closest friends) about a product vision that I’d completely lost sight of.

I’ve grown a lot as a person in the past two years. I’d like to share some of the struggles that I’ve gone through, and the ways I’ve learned to deal with them:

1. On Egos and MIT Syndrome

I’ve always struggled with confidence issues. As a way of compensating for this, I leaned on my programming licks; here was at least one thing that I was awesome at.

When I got into the startup world, something shocking happened. I started to meet people who were my equals, or even worse, better than me! This caused an existential crisis.

My confidence was built on a shaky (egocentric) foundation.

I try to approach software development more like rock-climbing now (my other passion) 

  • developers who are better than me give me something to aspire to.
  • developers at close to the same skill-level help push me.
  • I try to avoid taking pride in being better than someone. I’d rather help them get better (in climbing we call this giving beta).

2. On Stress

Bootstrapping a startup is stressful as hell:

  • Your product vision will change.
  • You’ll screw a lot of things up on the first try (hiring, pricing, marketing, design).
  • You’ll have a nagging feeling that you’re not moving quite fast enough.

I’m a somewhat stressed out (Woody Allenesque) character to begin with. Taking steps to deal with my stress has been hugely important:

  • I found a hobby I’m passionate passionate about. I try to always make time for it, even when work is hectic.
  • Every Sunday I take time to reflect: climbing, writing, thinking, and relaxing. Making an asserted effort to do this positively affects my whole work week.
  • I’ve forced myself to take occasional vacations. This can be hard when the company is young, but it’s necessary (your brain needs time to reboot).

3. On Social Life, and Balance.

All you can think about is your damn company! This can make it hard to be social; You’ll go out with friends, and all you’ll end up talking about is the current product features you’re working on.

Neglecting your social life is unhealthy for yourself and the business; I began getting depressed about the lack of a life I had outside of work. I’d bring this bad mood to work with me, in turn making it a worse place to be.

I’ve since made an asserted effort to dedicate time to my social life: going on trips with friends; going on dates; and, most importantly, getting work completely off my mind occasionally.

It’s definitely possible to go too far in the other direction, allowing your social-life to interfere with your work-life. But I think it’s possible, and necessary, to balance the two (lest you turn into a robot).

Building a company with close friends, and peers I respect, has been the best experience of my life. It’s well worth the struggles, but I need to constantly keep them in check.

I’d love to here other people’s startup experiences, I’m curious how typical mine are.

— Ben (@benjamincoe)

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