The Way Startups Die: Pivot Hell and the Not Shipping Trap
I see a lot of startups die. But the most painful deaths aren’t the sudden crashes; they are the slow, agonizing spirals into Pivot Hell.
Pivot Hell is that Limbo where a team hasn’t found an idea they actually have conviction in. They are moving, but they aren’t going anywhere. The primary reason they stay stuck? They stop shipping.
If you’re currently spinning your wheels, here is how you find your way out.
The Brutal Math of Ideas
Let’s be real: 99% of ideas are bad. Most things simply will not work. Only about 0.01% of ideas have the potential to become massive, era-defining companies. To hit that scale, you need the trifecta:
A Good Idea
A Good Market
A Good Team
If you have the team, the question becomes: how do you actually land on the idea? Standard startup advice tells you to pick something you’re interested in—Founder-Market Fit. That’s fine for identifying useful problems, but it carries a massive risk: Founders fall in love with their first idea and double down on a loser.
Why Pivot Hell is (Actually) a Gift
Believe it or not, Pivot Hell is a necessary phase for most startups. It’s where your team forms its intuition.
It’s the period where you realize what doesn’t work, which is just as important as finding what does. But there’s a trick to getting out of it. To exit Pivot Hell, you need conviction—the kind of conviction that makes you comfortable spending the next ten years of your life on a single problem.
That is a incredibly high bar. You can’t reach it by thinking; you can only reach it by doing.
The Only Way Out is Shipping
The most common mistake I see teams make in Pivot Hell is that they stop shipping. They spend quarters—sometimes years—theorizing, researching, and “pivoting” on paper.
If you want conviction, you need a product live. Period.
You need to see customers use it. You need to feel their response.
If it’s “kind of nice”: That’s not the pain you want to solve.
If it’s a “burning desire”: They will slap together the most half-assed version of your product just to make it work for them.
That “slap-test” is your signal. If a customer is willing to use a broken, ugly, incomplete tool to solve their problem, you’ve found it. That’s where conviction is born.
Set Your Criteria
Don’t let Pivot Hell become your permanent residence. Founders give up here because they don’t have a “success” metric.
Define “Working”: Set a hard criteria for what traction looks like.
Get Uncomfortable: Get out of your comfort zone and hand customers those “half-assed” products.
Listen to the Friction: If they aren’t fighting to use it, move on to the next experiment.
Stop trying to find the perfect idea in your head. Build something, ship it, and let the market tell you if you’re right.