Reflections on stepping back from being Keeper's CEO

Life choices, venture capital, and the next adventure

This morning, I announced my transition to President & Board Member of Keeper. After an wild ride — 7 years, $15M+ raised, leading the business to ~8-digit ARR & profitability — I’m handing the baton to my incredible co-founder David.

Is the AI likeness issue a legal thing? It never quite looks like me.

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Personal reflections

Today, on the day of the public announcement, I’ll take a few moments to jot down my reflections (in no particular order):

Humility and gratitude

When David and I founded Keeper in 2018, I was fueled largely by ego and ignorance. I wanted to make the world a better place — truly — but I also wanted to do it my way. The chip on my shoulder, coupled with a lack of genuine understanding of the path ahead, let me to strap into an incredible rollercoaster. 7 years later, the car has stopped and the bar is raised, and I’m left feeling so deeply grateful for the experience, the people who stepped up to help, and the business we were able to build. Keeper is a solid business and I believe it’ll outlive me. It has a solid moat, it’s recession-proof, and don’t think there’s any better person in the world than David to lead it through this next chapter.

The role of CEO

Before founding Keeper, I was a tricky employee. I rarely gave c-suite benefit of the doubt and was quick complain about org structure issues / misaligned incentives / lack of strategic clarity.

After doing the job these past 7 years, I think it’ll be a lot softer on leadership — there’s just so much going on all the time, and only a fraction can be shared with employees. It’s a hard job precisely because doing a good job means people won’t like you.

I was fortunate that Keeper never over-capitalized or over-hired, but I don’t blame CEOs that do and I can’t help but applaud unpopular decisions. When things aren’t going well, driving urgency is an all-consuming job.

Demon mode & personal limits

By most accounts I was a pragmatic and reasonable CEO (perhaps too much so), but demon mode was never far from the surface. Anger is a powerful fuel — and to be totally frank, I don’t really know how to be a great CEO without constant feeling it.

At any given time, somebody isn’t pulling their weight and letting your best performers down. For me, powering through the “bad news comes in waves” phases of the business requires tapping into anger.

Over time, I’ve come to realize that this intuitive anger is typically correct. It’s just that constantly acting on it requires intense personal sacrifice. I’ve decided where to draw my line, and it probably makes me a non-ideal CEO. As a founder friend of mine put it: “I figured something was wrong when I started pooping blood”.

Venture capital is awesome, in every meaning of the word

We are so lucky to work in a world that can support venture capital. The fact that we were given $15M in cash to go build Keeper is fantastic. And it worked! Keeper is worth far more than if the cash had been dumped into equity markets.

I’m so grateful to my board and the investors that chose to bet on us — thank you. It’s no secret that selling tax software directly to consumers is a Bermuda’s Triangle even for the strongest founders. You believed Keeper was different, and I applaud you for that. That’s what American dynamism is all about.

But of course VC is also “awesome” in the frightening sense. At Series A, it’s a bet that there’s a 5% chance that the business will be worth $1B in 5 years. Doing anything with a 5% chance of success can feel frightening — especially when your ego is wrapped up in it. If I ever do it again, I’ll know exactly what I’m signing up for.

What’s next

For Keeper

I’m grateful to have led the business through Chapter 1 — getting initial traction, figuring out how to make money, setting up a strong team. The business is now on a solid foundation, both financially and from a product standpoint.

Chapter 2 is about scaling off of that platform. I have complete conviction that the team will execute and win in the long-run, and that David is the best leader for the business in this new phase.

I will remain an active board member and help out where I can. I love the business, and I couldn’t be more proud of the team.

For me

I'll take a few months off, catch up with my SF community, and do some writing. Product management has always been my strong-suit, so I could see myself going back to those roots but I'm open to other paths as well.