We hosted the website on the spare computer in my bedroom and within a few months had our first pay customer and we continued to grow it from there.

However despite working on countless startups since then none of them replicated that success, despite me since becoming an accomplished software engineer and knowing far more about business.

The truth is any idiot could launch a successful startup from their bedroom with a bit of effort in the early 2000s. When me and my friend worked on our startup we were like 1 of maybe 2-3 companies doing what we were doing. Today I suspect that number would be closer to 1,000, if not more.

Those old bootstrapping stories don't exist anymore. The low hang fruit is gone. There's a huge amount of competition even in the most niche markets. And if you have competition they'll probably have an ad budget many times your total bootstrapping budget.

I'm not saying that it's impossible to bootstrap a startup, but statistically it's insanely difficult these days. There was an article on Indie Hackers a while back where someone looked at the stats for successful Indie Hacker projects it the guy found that only something like 1 in 200 projects posted on Indie Hackers even go on to make profit if I recall correctly.

You're an idiot if you're a dreamer today. You're almost certainly better off just getting a second job.