The Real Price of a Big Number
Business Insider profiles it as “monk mode.” Founders are starting to treat it as table stakes. But looking at the actual odds, going “all in” optimizes you to lose the only bet that matters.
Twice, my body has forced me to stop going all in.
The first time: bloodwork so alarming that my doctor put me on a three-month “reset.” The second time: an emergency tooth removal and a blast of antibiotics for the exact same problem surfacing a bit differently.
I made the same bet, both times. Trade health, relationships, and sanity for a slightly better shot at a very big result.
The First Time: The Billable Hour Trap
A year into practicing law, after transitioning to my dream practice area of startups and venture capital, I decided to go all-in on work. Learn everything. Bill more than anyone in the building.
Relationships got cut first. Then health, followed by whatever was left of my mental well-being. An idle ten minutes wasn’t rest; it was an opportunity. Bill, baby, bill.
I had the billable hours. I had nothing else. Then bloodwork came back and told me just that. I got the doctor-ordered reset. I got better.
Then, I did it again.
The Second Time: The Ambition Trap
This round wasn’t about billing the most. It was about building faster than anyone. I was focused on growing my practice, and with it, the Cincinnati and Midwest venture scene I’ve made my professional bet. It was the exact same all-in instinct, just coming in the form of ambition instead of hours.
If you noticed my social media presence go quiet recently, going “all in” again is why. My body sounded another alarm. This time, it was much more urgent than bloodwork. A dental infection bad enough to require antibiotics (with the caveat that I “might need to go to the hospital”) and rapid tooth extraction.
It was during that recovery that I read a story that made me stop and actually think about what I was doing.
What the Culture Gets Wrong About “Monk Mode”
Business Insider, with a companion piece from AOL, recently profiled founders going “monk mode” — cutting out literally everything but the company.
One 30-year-old founder called dating “not economically sensible” given his startup’s burn rate.
Another grew impatient with his girlfriend for needing time to process a disagreement, treating her the way you’d want a software bug fixed on a deadline.
A third had his laptop open at a wedding in India while his girlfriend scouted out Wi-Fi and snacks.
The culture isn’t entirely wrong. Less distraction and more intentionality beats the hammock-dwelling version of your competition every time. But here’s the flaw in the logic: if you’re focused enough to seriously consider monk mode, you were probably going to beat that competition anyway — without giving up everything else.💡
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Calculating the Actual Odds
A venture-backed startup has roughly a 1.28% chance of reaching unicorn status. Betting big when the math — expected value, the payoff weighted by the odds of getting it — justifies it is rational. Startups are one of the few places where the upside is genuinely that lopsided.
But the exit is not the only bet you’re making. The real trade is this:
Give up the things that reliably produce a good life — relationships, a working body — for a small shot at a life with a few more zeros in the bank account.
Most of the time, you lose that bet. That’s not pessimism. That’s the Vegas line.
If the company folds, what are you left holding? No company. Little to no money. Missing relationships — or, in my case, some missing teeth — because you optimized them away a long time ago.
The exit isn’t coming to save you and make everything better once it happens. The people you’d call to celebrate a billion-dollar sale might not still be there to pick up the phone.
Protecting the Payload
Tim Ferriss spent twenty years as self-help’s chief optimizer. I’ve consumed nearly all of his stuff. Twenty years in, he has landed here: relationships and well-being are the payload. Everything else — the systems, the habits, the grind — is just ancillary.
Founders who protect that payload don’t just live better. They decide better, precisely when decisions matter most — the term sheet, resolving the co-founder fight, nailing the key hire. Depleted people make worse calls. Getting rest and protecting relationships and well-being isn’t soft. It’s the actual competitive edge.
The Edge: Wear Out vs. Rust Out
None of this means doing nothing. My own mantra has always been wear out, not rust out — choose action over inertia, every time. Regular readers know I quite literally have this tattooed on my arm.
But wearing out and working yourself into a hospital bed aren’t the same thing. One is about showing up. The other is about disappearing into the job until there’s nothing left to show up as.
This isn’t a hobby argument for me. It’s the bet I’ve made professionally.
As a partner at The BOLD Fund, our entire premise is built on this: the lonely, grind-yourself-down model of venture isn’t just hard on founders — it’s actively bad for the companies they’re building. Founders who are cared for, mentally and physically, make better decisions. Better decisions build companies that last.
Founder wellness isn’t a side concern. It’s the ultimate competitive edge. Bet on that rather than the big exit.
Really excellent observation. Whether you are a founder or someone climbing the corporate ladder, we have all had times where professional ambition and accomplishment has outweighed balance in our lives. It can be done for a short time, but it is ultimately not sustainable.
I liken it to rushing to build your house and then overloading the foundation. It may look like a beautiful structure going up, but will eventually crumble under a weight it cannot carry.