Some of the worst startup founders I have seen are people who come from being execs or management at very large companies, because they have no frame of referen

Some of the worst startup founders I have seen are people who come from being execs or management at very large companies, because they have no frame of reference for how things should be done when you have 5 people. So I don't think you can generalize on that point. And as far as this goes: > That guarantees at least enough investment to hire a team the size of what you had at Apple. There's also no way this is a guarantee. Sure, it'll be easier to get money than an 18 year-old walking in off the street will, but again, you can't compare the steady job, steady paycheck, "let's build a feature internally" with "let's go start a startup". I will definitely agree that having the experience of a vp of engineering is better than not having it, but that's a far cry from saying that quitting your highly paid job as a VP of engineering for the biggest company in the world to start one of many cloud storage companies is "not a huge risk".