They say only one out of 1000–2000 startups becomes a unicorn, and that only 1% of humans will ever finish a marathon.

If you had asked my mother, though, she would have told you it was a thousand times more likely I’d build a billion-dollar tech company than finish a marathon. And I would’ve agreed. I was that kid in school with straight As who still almost failed PE. Two laps around the soccer field and I’d be hyperventilating.

On New Year’s Eve last year, my co-founder Jacob slipped on the snow and broke his ankle. A gnarly injury. Fast-forward to March 1st, and he announces to the entire company and our investors that he is going to run the California International Marathon on December 7th. And also, he invited people to join him in his crazy adventure.

I considered it for a split second and literally laughed out loud. This guy will do it, I thought. He’s delusional and stubborn enough to crawl the last 10 miles if necessary. But me? No chance. The longest run of my life was a single 10K, once, years ago. I ran it, and then immediately retired from the sport.

But the idea stayed in the back of my mind. If Jacob crippled, needing surgery, with months of PT, could commit to running a marathon… what excuse did I realistically have? I was healthy. I had a head start. And honestly, after the twins were born, my exercise routine was basically nonexistent. Running was something I could technically do anywhere. My wife, fully aware of how much I hated running and how hard this would be for me, became a supporter.

So I downloaded Runna. And I ran.

I hated it. Deeply. Running felt like the most boring, repetitive, form of suffering ever invented. But something weird happened: I started seeing progress.

collage of running sessions

Three miles stopped feeling like a death sentence. Then I ran 10. Then one random morning before giving a conference talk, I ran a half marathon by myself. And it didn’t even feel that hard. I started waking up earlier and earlier to get my mileage in before the morning meetings. Discipline compounds quietly, until suddenly you’re a different person.

This year I traveled a lot. Yet running turned out to be the easiest habit to keep. I ran more than 900 km in 18 different cities. Running became a new, exciting way to explore a city. A nice way to start the day with a small win before all the startup chaos.

This weekend, we did it. We ended the race in way more pain than we probably should have, but we crossed the finish line. And the biggest lesson I learned, bigger than training plans, pronation, and fueling… is this: You need to be a little crazy and do hard things. And that’s kind of the whole point. Life isn’t about being the best in the world. It’s about being the best version of yourself. Expanding what you thought your limits were. Rewiring your internal narrative from “I could never do that” to “actually, maybe I can.”

I’m insanely proud of Jacob for this comeback story, and grateful (even if involuntarily) that he dragged me into another ridiculous adventure. It was worth it.

And maybe this story nudges you toward something you’ve always dismissed as impossible. After running these 26.2 miles, building a decacorn feels easy. Okay, not easy, but you get the point.

medals

Will I do it again? I don’t know. If I had put this much time into surfing, I would suck a lot less at it and probably enjoy it more 😅. But I’ll keep running. It keeps me fit, clears my mind, and makes me a better version of myself. Which, in turn, helps me be a better founder, partner, and dad.

Special thanks To Runna, genuinely a fantastic training app (and RC user!). To Marina, for the endless support and the childcare coverage while I disappeared for very long runs. To Andrew, Harlan, Bobby, Susannah, Sarah, Nacho, Chris, Mica, Matt, and Olga, for the advice, motivation, and for putting up with my running updates.