Health Is the Most Asymmetric Bet You’ll Ever Make

Last year I bought one of our founders a WHOOP. I joked, at the time, it was for me to track him 😉

This week we caught up and ended up spending an hour talking about various things including our health regimens. I’m on my last day of a Prolon fast yay! (highly recommend), so it’s top of mind.

The discussion turned to optimization of health and that you can do everything right and still get unlucky. Eat well, sleep eight hours, workout, wear the tracker. We both *try* to eat well, get all the scans, and stay on top of the latest trends. And yet randomness still finds you. The healthy guy I knew got cancer, and others we know lived ages while taking a shot of vodka before bed (maybe that’s the answer?!).

I can’t help relate it to my day job.

In venture we talk endlessly about asymmetric bets. Small input, massive potential return. Hard to know whether the inputs will yield the right outputs.

The inputs to health – sleep, exercise, fasting, stress management – are relatively modest. The output is a materially better decade of function, energy, and clarity. What the longevity crowd calls healthspan, not just lifespan.

It’s oddly so similar. The small inputs have a LONG feedback loop (hopefully) and there are times where you think they don’t matter. And its hard work – and sometimes you look on social media and everyone makes it look like they won the venture (or health) lottery.

But that’s also true of everything. You can back the right founder, right market, right timing – and still get killed by a macro event or a competitor who got there first. Randomness is real in both places.

The answer in startups isn’t to stop investing. It’s to make enough bets, with enough care for every one of them, to let the odds work in your favor over time.

I’ve spent 13 years helping founders make asymmetric bets on their companies. I’m now applying the same logic to the one thing I can’t recapitalize.