Your startup advice is decent, I just don't have the stomach for it anymore. Been there, done that, have 600,000 worthless stock options to prove it. I feel like I have better odds at the poker table.
I understand. I'm just saying I did it and got $1m+/yr out of it. I've done startups before that lead nowhere - so I understand the feeling... It's not like joining startups at seed stage or something - I'd only join one with a $XXXm dollar valuation or greater. (And one that has gotten that valuation very quickly hopefully - not over 10 years) I left because of the horrible environment before I vested everything. I decided if I can find a job at $350-400k/yr with some minor upside and a much better culture then I'd probably be happier in the end. (I have about 8 YOE)
Maybe joining a startup on the hyper growth track would be good financial returns. Only need one of those to do well to buy the house with cash at your likely experience range and the compensation they would be rewarding you.