I don't have a comfy US tech job, and never have, but I would love to. Closest I got was doing PM work for a startup in which I had significant equity (but ended up failing). Funny enough, YC doesn't even let me attend their job webinars!

Truth is though - if I could ever achieve a payout of a few million or more, I'd call it a day, right on the fucking spot. Invest in long stocks and dividend stocks, and go live in a small home near a cold weather city. I grew up around billionaires, and they scare the shit out of me...no intention of becoming one.