Bootstrapping a side project into a profitable seven-figure business

I love how these stories always start with “I just wanted to scratch my own itch” and end with “...and now I’m running a company with a payroll bigger than my old day job.” It’s inspiring, but also a little bit intimidating. Makes you wonder how many potential seven-figure ideas are just sitting in people’s “maybe someday” folders. The real lesson here? Ship something, even if it’s ugly. You can’t optimize what doesn’t exist.

For me the lesson is: ship the thing that makes you feel like you are playing Golf doing it (assuming someone who plays Golf enjoys it alot).

The golfer won't regret their day on the course. And if you fail on the passion project it won't feel like a fail.

I have another idea too. It's the win anyway system. Pick something that if you fail you use those skills at work and get ahead. E.g. the side project is also the training for the gap in your career.