When you meet enough founders you notice something sad. Most of them have never defined what “success” means. They grow for the sake of growth. They grind because they’re told to. They don’t stop because they never thought to.
I’ve seen this play out dozens of times. Smart people. Solid businesses. Chasing someone else’s scoreboard and don’t even realize it.
Borrowed Scoreboards
Building a startup is like playing a board game where there are no rules, you don’t know the pieces, and you define your own scoreboard.
Except most founders don’t. They borrow one.
Do you ACTUALLY care about raising money? Do you ACTUALLY want 1,000 employees? Do you ACTUALLY desire a $1B valuation? Or did someone else put those numbers in your head?
The thing to know about the default startup scoreboard: it was designed by people whose incentives don’t match yours. VCs need power laws. They need you to swing for the fences because their model requires 1 out of 10 to return the fund. That’s their game. It doesn’t have to be yours.
I watched this happen from the inside. In 2021, I was profitable and VCs asked me why. “Do you not care about growth?” Now those same VCs preach profitability — after they pushed their own portfolio companies into the ground chasing growth at all costs.
We were globally remote before it was cool. We seedstrapped before it was a term. We were profitable while everyone spent. VCs told us we were wrong at every step.
The advice changes with the market. The incentives never do.
A higher valuation? That’s a liability. Higher risk of a down round. Higher bar for acquisition. Projections you’ll never hit. If you can’t make it with $500k, you won’t make it with $500m. Cash doesn’t solve problems. It accelerates what’s working or buys you time to figure it out.
Most founders I know who borrowed the VC scoreboard ended up in the same place: profitable but trapped. Making money but unable to touch it. Stuck between a cap table that demands $1B and a business that’s worth $30M.
First step: question whether the game you’re playing is actually your game.
The Income/Stress/Control Matrix
I keep coming back to three variables: income, stress, and control.
Income vs. stress is the ratio that matters. Maximize income. Minimize stress. Skew too far in one direction and you’re in trouble.
The wealthiest founders I’ve met are not the happiest. They optimized for income and sacrificed everything else. But stress-free isn’t great either. No challenge. No edge. Honestly boring.
Success measured on income alone is not success.
Control is the variable most founders ignore. Your startup is nothing without you. That means you have control — over the business, the model, how you spend your time. But only if you exercise it. Most founders hand that control away the moment they take money, hire the wrong people, or chase someone else’s version of scale.
The founders I know who seem genuinely satisfied have found balance across all three. Enough income to not worry. Enough stress to stay sharp. Enough control to live on their terms.
My friends often ask me why I put up with this lifestyle. Incredible stress, low stability, few vacations, can never turn off. Meanwhile they make great money with none of the headache. The honest answer: the stress-to-income ratio is only part of it. The control — building what I want, how I want, when I want — is worth more than the salary gap.
If you want to be rich, don’t join a startup. Salaries are low, stress is high, odds are terrible. You’ve got to enjoy this life to keep living it.
Designing the Business Around the Life
It surprises me how few founders actually design their life. They keep going and wake up with one they don’t like. Then do nothing about it.
I know too many founders who hate their businesses. Too many employees who hate their jobs. The fix is not always “start a company.” Screw it, rent out your time. There’s no shame in getting a paycheck and checking out.
But if you are going to build — build something that fits the life you want.
For me, building is the game. It’s less about the industry or vertical than it is about the business, model, and strategy. That’s what energizes me. So I designed around it: a profitable YC company, investments in cashflowing SMBs, golf clubs, spin-offs. Diversified, profitable, and — this part matters — interesting.
I didn’t stumble into that portfolio. I chose it.
9 out of 10 startups fail. If you’re doing what everyone else is doing, you’ll fail with them.
The real question isn’t “what industry should I pick?” It’s “what kind of day-to-day do I want, and what business model supports it?”
Being a founder has turned out worse than I imagined. Harder, more stressful, unrelenting. But more rewarding than I ever thought possible. There’s no job I’d trade it for. That’s alignment. The hard parts are worth it because the shape of the work matches what you actually care about.
Recalibrating Before You Break
I locked in for 5 years. No weekends. No breaks. Just worked.
Does that sound impressive? It sounds incredibly stupid to me.
Only idiots and scam artists preach constant hustle. I’ve never met a truly successful person who preaches that bullshit. Don’t grind so hard you have no life. You’ll end up on a yacht with no friends at your wedding.
You’re playing a long game. Trying to sprint the whole thing is not only dumb — it’s irresponsible.
The feelings you have now don’t go away. The problems only get harder. The stress only gets worse. Success changes your bank account. It won’t change the rest.
I didn’t learn this from a book. I learned it from 5 years of grinding without stopping and realizing I’d burned through relationships, health, and energy I couldn’t get back. After 3 full weeks of travel, meetings, dinners — I need rest. Skip it and it’s a fast track to burnout.
The founders I know who last are the ones who check in with themselves. Not on some schedule. Just honestly asking: is this still the game I want to play? Is the ratio still working? Am I grinding because it matters, or because I forgot how to stop?
Don’t grind so hard you lose your friends. You’ll wake up successful and lonely.
Pick Your Game
Most founders never define success. They grow because they’re supposed to. They raise because everyone else is raising. They work 80-hour weeks because that’s what founders do.
Question the borrowed scoreboards. Know your numbers — not just ARR and runway, but income, stress, and control. Design a business that fits the life you want, not a life around whatever business you stumbled into.
And be honest with yourself along the way. Check in. Recalibrate. Admit when the game you’re playing isn’t yours anymore.
I’m not saying avoid the hard game. I raised $3m in 14 days. But it’s my game. I chose it. That’s the difference.
Based on years of watching founders — including myself — figure out what they actually want, usually after years chasing what they thought they were supposed to want. The income/stress thread I posted got a surprising response. Turns out a lot of founders are quietly doing the same math.