What I Learned From My Failed Startup
We raised $2.3 million to build a product that seventeen people ever used regularly. Not seventeen thousand. Seventeen. After three years, two pivots, and countless all-nighters, we shut down and returned what was left to our investors. This is what I learned.
The Idea Felt Right Because We Wanted It To
We built collaboration software for architecture firms. My cofounder's father was an architect, and we had watched him struggle with fragmented workflows for years. The problem was real. Our solution, however, was something we invented in a conference room rather than discovered through customer research.
We convinced ourselves that our vision was correct because we wanted to be building something. We had quit good jobs. We had told everyone we knew about our startup. Admitting that our core assumptions might be wrong felt like admitting that we had made a terrible mistake. So we didn't admit it, not for two years.
The most dangerous ideas are the ones that feel obviously correct. They discourage the investigation that would reveal their flaws.
We Optimized for the Wrong Metrics
We tracked signups obsessively. Every time someone created an account, we celebrated. We had thousands of signups. What we didn't track, until far too late, was activation. Of those thousands who signed up, fewer than five percent ever completed a project in our tool. Fewer than one percent came back a second time.
Signups were a vanity metric that made us feel good while hiding the fundamental problem: people tried our product and decided they didn't need it. If we had focused on retention from the beginning, we would have recognized the product-market fit problem much sooner.
Our Investors Couldn't Save Us
We had experienced investors who had backed successful companies before. We assumed their involvement meant our idea was validated. It wasn't. Investors make bets; most of those bets fail. Their decision to invest means they see potential, not that potential will be realized.
More damagingly, we sometimes did things to please our investors rather than our customers. We built features they suggested because they were important people whose opinions we respected. Those features didn't move our metrics because our investors weren't our users.
The Pivot Wasn't a Strategy
When it became clear our original product wasn't working, we pivoted. Then we pivoted again. Each pivot felt like progress—we were adapting, learning, iterating. In retrospect, our pivots were panic responses, not strategic decisions.
A good pivot preserves something valuable from what you've learned while changing what isn't working. Our pivots preserved nothing. We just tried different things because the current thing wasn't working. That's not pivoting. That's flailing.
What I Would Do Differently
I would spend six months doing customer research before writing a line of code. Real research—not surveys, but conversations. Understanding workflows, pain points, existing solutions, willingness to pay. Only after developing genuine insight into the problem would I attempt to solve it.
I would define success metrics before building, and I would make retention the primary metric from day one. Growth without retention is a leaky bucket that no amount of marketing can fill.
I would be ruthlessly honest with myself about what was working and what wasn't. The comfortable delusions we maintained extended our failure by at least a year.
Most importantly, I would remember that the goal is to build something people want, not to be a founder. The identity of "entrepreneur" seduced us into continuing when we should have stopped. The company became about us rather than about solving a problem. That inversion made failure inevitable.
I'm building again now, more carefully. The lessons were expensive, but perhaps they were worth the price.