There's a folkloric belief that ESR got very wealthy, because he wrote a blog post about how wealthy he believed he had gotten on VA Linux, but I don't think that really panned out. If you paid attention to his blog, while he was writing it, the last couple of years the narrative was instead that he was on the edge of not being able to do open source stuff anymore because he had no income; some of his friends/fans even wrote comments complaining about him asking for money, when everyone else just solves this problem by getting a job.
I don't know any more than anybody else who reads blog posts about this stuff, but I strongly suspect that he did not in fact blow a giant fortune, but rather, like a lot of people who briefly had a lot of paper wealth at that time, it never really materialized. It's an embarrassing blog post to write, "I thought it was rich, turns out I'm not", so there isn't the matching post.
I don't know any more than anybody else who reads blog posts about this stuff, but I strongly suspect that he did not in fact blow a giant fortune, but rather, like a lot of people who briefly had a lot of paper wealth at that time, it never really materialized. It's an embarrassing blog post to write, "I thought it was rich, turns out I'm not", so there isn't the matching post.