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by jfengel 2031 days ago
I screwed up my life pretty badly by sticking with my startup for more than a decade. All that stuff about "Winners never quit..." I should have quit.

I kept it going in part because I had personally backed a large loan, which came due all at once when we finally folded. That was a very, very bad day for me. I managed to salvage it -- part of the reason I was able to last so long was that I'd had some successes during the dotcom boom. I lost all of that.

I failed to fail fast, which is easy to say in retrospect, but I would have been equally tsked at if I'd let it go without trying harder. Beyond a certain point (a few years) it was clearly just inertia and depression, and bad advice I got from people I brought in to be CEO.

We quit for real when our solitary customer dropped us. They never really understood what we were good for -- a story that I never managed to tell really well, despite still believing in it. The world went in exactly the opposite of the direction we aimed at: high quality data with powerful semantic reasoning.

I did everything wrong, and was really bad at it, including knowing when to quit. My life is going great now, and I'm incredibly fortunate, but if I had two pieces of advice it would be "Don't" and "Listen to your friends who tell you you're being stupid."