See my comment above - not the person in question (to my knowledge), but also no degree and hit 2001 with 2 years experience. I'm not "hacker news material" - i.e. no Big Tech or Startup experience. Just slowly, steadily worked my way up in salary mostly at small-ish (6-100 employees) software / marketing agencies or doing similar work.

I don't recall what path his friend took.

As for my advice, I don't regret it at all. But the one thing that might have made a difference was that I could afford to put our sons through college (public school, UIUC) so neither graduated with debt.