It's clear from your post and comments that you're a very smart guy. I can tell you think so too, but I'd bet you're even smarter (relatively) than you realize

It's clear from your post and comments that you're a very smart guy. I can tell you think so too, but I'd bet you're even smarter (relatively) than you realize. I agree that if you follow your plan, you're likely to be successful, if you don't give up just a bit too soon and go back to the solid, dependable paychecks. My only two cents concerns your patience. I'll admit, my only experience working for someone else was a year-long internship right after college, but despite it being a sweet gig in a beautiful place, I hated it, and it was all I could do to make it to the end of the year. Since then, it's been only startups for me, and it's so incomparably different and better that I just have to weigh in that your 3 year plan is a little too patient and risk-averse for me. It sounds like you love your job already. That's definitely key. But if you wait another 3 years to go for it, and find out you're fantastic at it and are having the time of your life, won't it seem like you should have given it a go even sooner? For instance, by getting a cofounder willing to pay the company bills for a while as an even trade for your fantastic ideas? Seems worth considering if you'd both rather start sooner than later. Making your own stuff full time is so fun.