Why I Broke All the Startup Rules—and Why It Worked Better Than Following Them

Key Takeaways

Bootstrapping my solo AI startup showed me that the common “best practices” aren’t always what they seem.

I discovered that sometimes, breaking the rules is exactly what you need to do when you’re flying solo.

When you’re bootstrapping a solo AI startup, everyone has an opinion.

Freemium. Waitlists. Subscriptions. Build in public. Raise capital.

These so-called “best practices” get repeated like gospel. But here’s what I’ve learned the hard way: most of them aren’t rules — they’re just suggestions that worked once for someone else.

Some advice is useful. Most of it is conditional. And a lot of it? Just noise.

I don’t ignore all of it. But I’ve learned when to break the rules — and why it can actually work better when you do.

1. I skipped freemium. Here’s why I don