How I chose to step down as CEO of the startup I co-founded to pursue a happier life

On the Muldrow Glacier, approaching Mt. Denali in Alaska, 2004.

I follow the general premise that life is part purpose-driven planning and part serendipity. We always have control over our deliberate planning and execution, but we also need to be ready to pursue serendipitous opportunities even though we’re not in control of them when they arrive. I’ve written about this as part of my life strategy before.

One of those serendipitous moments came last year when I was asked to take the helm of Odd Networks, a startup I had helped found barely a year earlier. We created a software platform for managing and delivering video content to streaming devices like mobile phones, tablets, smart TVs, Roku, and Apple TV.

When I took the lead as CEO, the plan was to get a couple of big partner deals to fund the company in the short term (which we did) then raise money for higher growth (which we did not do). Along the way, we took on a convertible debt note (a complicated financial fundraising instrument) and even acquired another startup.

A second look

Up until this April, I had been working 60 to 70 hours a week and traveling about once a month to make Odd Networks into the growth company we wanted it to be. Last summer, my wife and I made a pact that I would put everything I had into the company until April. If I didn’t have a deadline, the workaholic behavior could have gone on forever. It was fortunate that we did because when April came around, my mind and body were at the end of the proverbial rope.

After slowing down that month, and by pure coincidence, my co-founders and I began to take a second look at the strategic direction of the company. With time running out to raise venture capital, we had to make some dramatic changes on how we defined success.

In the end, the venture investors we were talking to were right. The space we targeted in the video industry was not primed for the kind of growth that would yield returns. And besides, did we really want to adopt the lifestyle of running a growth company?

If we decided to sell the company instead, it would have to be done within the next 12 months or we would run out of money without venture funding. It would have been a lot of work and dedication, but the payout might be worth it—in theory.

In an essay (you really should read it), Paul Graham explained this idea of working hard to sell a company as compressing decades of your career into a few short years. According to him, we should be prepared for the workload of that compression. And therein lies the catch.

What I couldn’t do as CEO

This is where purpose-driven planning comes into play. Investing all our effort into Odd Networks and selling it carries a risk that began to outweigh the work required for a successful outcome. We also wanted to be able to continue to grow the team under a new parent company here in Saratoga, New York if we were acquired. And this put an extra risk vector on the whole thing. It’s a classic ROI calculation, and the ratio was not working out in favor of selling the company.

At the prompting of my co-founders, this got me thinking, what would make me happy? What do I want my life to look like in six months? 12 months? 18 months? I think we all need to do this more often. It’s easy to get heads down in our daily work and lose sight of where we’re trying to go.

It’s easy to get heads down in our daily work and lose sight of where we’re trying to go.

I decided I wanted Odd Networks to be a part of my future, but not to consume it. I want to be at the center of my kids’ lives (who are five and eight years old). I want to travel with my family. I want to help others learn software programming. I want to get more seriously involved in the political causes I believe in. I want to run for the school board. I want to get fit and climb big mountains again. I’ve done really well trading options on the stock market in the last five years and I should do more of that. I’d like to do some real estate investment too.

I can do all those things, come to work, and do a great job as a software developer at Odd Networks. But I can’t do that as CEO. And frankly, I would do a bad job at all of them if I tried. In fact, I was trying to do some of them simultaneously and was already failing. I realized that at this point in my life, with this company, I couldn’t separate the CEO role from the software developer mindset and my desire to be involved in things I want to work on.

A tapestry of many things