I doubt you'll find a consensus on this question. My opinion, for what it's worth, is that this also follows the dictum of "asking if you should fire someone m

I doubt you'll find a consensus on this question. My opinion, for what it's worth, is that this also follows the dictum of "asking if you should fire someone means you've already made your decision", and prevaricating only prolongs the pain. I made a similar decision with much less of a financial cushion (and without moving away from the west coast) and it worked out OK. I'm happy now and don't regret giving up the millions. YMMV, of course. One tip: make it your goal to get to ramen profitability ASAP, not in 2-3 years -- it has a wonderful way of focusing your work. Good luck whatever you choose, and keep in mind that either decision will remain reversible for at least a few years. If you go out on your own, I don't think having "I tried to run my own startup, failed, and learned a lot" will be a negative when seeking another tech job, and you can always move back.