I’m inspired by obsidian.md as a business – I think it would be great for the world if more companies could be small businesses with highly aligned values and a stronger decoupling from capitalism.

What makes bootstrapped businesses work?

My (working) hypotheses:

Product / Market Fit

You have to find something that is intentionally small so that you can’t be out-competed by scaling. This means finding an intentionally niche customer segment that can’t sustain a $1B business. VC funded companies will bounce off in search of bigger markets.

Positioning / Dividing Lines / Values

Sometimes you can segment a larger market by having clear values that segment the market. This means that you can focus on one half and build a superior product than one that tried to cater to both.

If you want to build a bootstrapped business, you need to be opinionated and exercise taste.