Business

Things you bet on.

Startups that died. Side projects that rotted on a hard drive. The customer who never came. The pitch that nobody answered.

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For every founder on a magazine cover there are a thousand who shut down quietly, paid off the credit cards, and went back to a normal job. Their stories don't get retweeted. They get whispered, if they get told at all.

This page collects them. The pivot that didn't pivot, the co-founder breakup, the 18 months of runway that turned into 6, the great idea that turned out to be a feature.

Failing in business isn't a moral failing. It's the default outcome of trying. Survivorship bias just makes it feel rare.

A question for you

"What did you bet on that didn't work — and what did you learn about yourself when it didn't?"

Answer it →

Latest in Business

6 total

We pivoted six months too late

We had data showing the original product was not working in month four. We pivoted in month fourteen. By then half the team had quit, the board had stopped returning emails, and the new direction needed money we no longe…

We ran out of runway with no warning signs

We had what we thought was twelve months of runway. The CFO had been hiding a payroll miscalculation for two quarters. Real number was three months. We told the team on a Thursday. By Monday, half had already lined up in…

Complete failure

Everything I do, remains unfinished. ALL THE TIME.

Launch day was completely silent

Two years of building. Press kit, launch video, beta list of four thousand people. Tuesday morning the post went up. By Friday we had done three hundred dollars in revenue and eleven signups. I refreshed analytics for a …

Sued by the competitor we were trying to beat

We were small. They were huge. We launched a feature that competed with one of theirs. Their lawyers sent forty pages. Our lawyers said we would probably win, but it would cost more than we had. We took the feature down,…

My co-founder breakup killed the company

We met in grad school and built the thing over five years. Then we disagreed about a fundraise. Then a hire. Then everything. Lawyers got involved. The company kept running for six months, but it was already dead. I lost…

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