December 2023, St. Pete Pitch Night. I got up there with Fedscribe, an AI proposal writer I had built mostly so I would stop hating my own Tuesdays. It won five thousand dollars.
And then, standing there holding a novelty check that is genuinely , I realized I had pitched the wrong thing.
The tool wasn't the prize. The prize was noticing that the AI work now paying real bills had been sitting inside a side project the whole time, and I had very nearly filed it under "cute."
Nothing about it was visionary. It fixed one bad afternoon I personally had, every week, on schedule.
The check was big in both senses. The lesson was bigger.
Build the tool that fixes your own Tuesday. That's the one with a market.
If you won't use it on a bad week, nobody is going to use it on a good one.