A tale of personal failure

..maybe

My last post for this newsletter was roughly a year and a half ago. It was an honest write up about the challenges of raising a newborn and running a startup. It was optimistic. But not overly so. “Maybe I can handle being a good father while building a company,” I said, “Maybe.”

Long story short—I couldn’t.

2023 was a year of peaks and valleys. The peaks were high. I watched my daughter grow from a 6 pound infant to an opinionated toddler. But I also watched as the growth of my startup plateaued. The lack of sleep that came with being a new parent combined with the pressures and anxiety of a struggling startup was a toxic mix.

I was never officially a founder, but I always felt like one. I joined the company as employee number one. I saw it through a YC batch and a couple of pivots before we hired again. And when the founders left (for frustratingly noble and prescient reasons), I had the hubris to think I could carry the torch without them and grow SharpestMinds into a “real” company.

And maybe I could have. Maybe the timing was wrong. Maybe I had bad luck. Maybe I could have stuck it out a bit longer and got over the parental exhaustion. Maybe I should have pivoted. Maybe I should have raised more money. Maybe this. Maybe that.

The maybes ate at me. They kept me up at night. My heart knew that my current path wasn’t working. But, for too long, my mind couldn’t let go of the maybes.

It’s hard to say what broke the camel’s back. Eventually, with a certain amount of clarity, I decided it was time to get out. The founder’s path was not for me. At least, not here. Not now.

SharpestMinds lives on under new ownership. I think that’s what it needs. And I have gone back to my roots as a software engineer. There’s a lot to unpack in those sentences. Something I may do in future posts. For now I’ll say that, in 2024, I am much happier overall. A proud, attentive father and a humble practitioner, eager to hone my craft.

Of course, I’ll never be 100% sure that I made the right call. I’ll always have the maybes.