Published: February 24 2013

1. Where were you in 2012?

Fourteen months ago, in my last semester of college, I began working on a start-up idea with a few folks I had met through school. The company we started is off to a good start.

As it turned out, (as it surprisingly often does) it’s not always a great idea to start companies with people you know only by reputation. We spent quite a bit of time over the second half of 2012 looking for ways to work together productively, and then separately came to the same conclusion: I had to go.

2. What’s it like?

It sucks. Leaving a cause that you spent the last 12 months of your life enveloped in, is a painful experience even when the departure is as amicable and unanimous as ours. Nothing really compares to the satisfaction gained from throwing all of your available energy, every day, to a cause you believe in on a fundamental level.

Still, there are upsides. More time with the girlfriend, more catching up with old friends and fascinating acquaintances, a chance to get in better shape, write, maybe travel. I’ve had a chance to step off the high school to college to job conveyer belt before, and was better off as a result. The important thing (I hope) is to take note of lessons learned and keep my eyes open.

3. Lessons Learned

  • I’m not sriracha. I don’t go well with absolutely everything. Some teams and environments make me dramatically more happy and productive than others. In the future, I’ll be a lot more picky and careful about who I work with, both for their sake and for mine.

  • Date before Marriage. I was very hesitant to join my 2012 team, since we hadn’t worked much before. In retrospect, the apprehensions were correct, and ignoring a wealth of advice about having worked together before was wrong.

From now on, if (and when) I start a new venture, it’ll be with folks I’ve worked with before successfully, or at least after a non-trivial trial period.

4. What now? [Update: April 2013]

I’m currently spending 3 days a week working freelance for Baydin, the creators of the Boomerang Gmail plug-in. I’m working on Boomerang Calendar, trying to make the ping-pong that is meeting scheduling over email a little bit less painful. Baydin are an awesome bunch of folks (who deserve their own blog post), and I’ve been thinking about scheduling as a problem before, so the gig has been pretty fantastic.

  • If you’ve got feedback or ideas for Boomerang Calendar (or want to try it out), let me know!.
  • If you’re in need of a freelancer and want a full-stack generalist who loves product and has some experience with hackathons: that, also, is me.