Not every business is as free-form as ones where you luck into a $100k/month business when you're just two college kids. In that scenario of course you can throw as much spaghetti against the wall as you want with total creative freedom. But most startups do not happen to be at exactly the right place at the right time like this, and it's a multi-year slog to creak into profitability, and then several more years of intense focus to actually achieve real success. If you want to cash out early to buy yourself the freedom to work on whatever you want, and you end up getting paid more than 99.999% of the world for your months of hard work, I don't see any way you can call that a failure. Even assuming no element of luck and that Jake is just one of the most naturally talented entrepreneurs alive, I still think expectations need to be re-calibrated here.