A decade of startups: what the lows teach you
I have been a founder for over a decade now, which in startup years is roughly nine hundred. People ask about the highs — the raise, the launch, the good month — and those are lovely and last about a weekend. The lows last longer, and, annoyingly, they’re where all the learning is. Nobody frames it that way at the conferences, so let me, from the quiet end of the info booth.
In the daylight layer I’m a cofounder of Wistkey, and before this there were other rooms, other builds, some that shipped and some that quietly got deprecated. Here’s what the low points actually taught me — the stuff I’d tell a newer founder over a coffee, not from a stage.
The highs are loud; the lows are where you learn
A high — closing a round, a big customer, a good launch — feels like proof you’ve made it. It isn’t. It’s a checkpoint, and the game keeps running. The lows are different: a quiet month, a deal that evaporates, a hire that doesn’t work, the stretch where nothing is obviously wrong and nothing is obviously working. That’s the part that teaches you who you are and what the company actually is.
The highs are checkpoints, not endings. The lows are where you find out what the company is actually made of.
What the lows actually teach
- Cash is just time in disguise. Fundraising isn’t a trophy; it’s buying more turns. Once you feel that in your stomach, you spend very differently — and you stop confusing a raise with success.
- Morale is a resource you can run down. You can push a team through one hard sprint on adrenaline. Do it for six months and you’re spending something that doesn’t refill on a Friday. Protect it like runway.
- Watch what you reward, not what you say. In a bad stretch it’s tempting to praise heroics and all-nighters. Do that and you’ll get a team optimized for firefighting — the scoreboard problem, aimed at yourself.
- You find out who’s actually with you. The lows quietly sort the people who signed up for the mission from the ones who signed up for the momentum. Both are fine — but now you know, and knowing is worth a lot.
How I survive them now
- Shorten the feedback loop. When the big picture is grim, find the small true thing you can ship this week. Momentum is manufactured, not found.
- Separate the fear from the facts. Write down what’s actually true versus what 3am says is true. They are rarely the same document.
- Keep one honest person outside the building. A mentor, another founder — someone who isn’t in your cap table or your head. Which is really just asking for help, the thing I never shut up about.
- Zoom out to the runway, not the day. The day feels terminal. The runway usually says you have more turns than the panic claims.
On the “is it worth it” question
People considering the founder path want to know if the lows are worth the highs. Honest answer: only if you’d find the work meaningful even on the flat, unglamorous middle days — because that’s most of them. If the mission only makes sense when you’re winning, the lows will feel like punishment. If it makes sense anyway, they feel like tuition. Expensive, but you keep what you learn.
A decade in, the highs still feel great and still last about a weekend. But I’ve stopped waiting for the next one to feel okay. The company is what it is on the ordinary days, and so, it turns out, am I. That’s the real thing the lows teach — and it’s worth more than the highlight reel that never shows them.
