How I spend money as a bootstrapped founder. Bootstrapping means one thing most people don’t talk about: You don’t get to outsource thinking. Every week, you decide what’s worth paying for — and what isn’t. And there’s data behind why this matters. CB Insights shows that 38% of startups fail because they run out of cash. Not because they lacked vision — but because spending didn’t translate into progress. Here’s my rule as a bootstrapped founder: If I already know how to do it, I do it. If I can