I think more people would regret it if they knew what they were giving up, but most would probably not make that calculation. If he had kept his corporate job and spent the initial $30k a year he could have retired early only 10 years later. Maybe less if he'd be willing to live very frugally. Then he would be free to build as many apps and games as he wanted, giving him many chances at getting a big hit.

I'm in this dilemma myself, as I've always wanted to do something more risky, but I don't want to jeapordize my ability to be financially independent at ~40. Being stuck in a potentially crummy corporate job with potentially terrible management and coworkers for another 25 years (not the case now, but things can change quickly) is the regret I want to minimize beforehand.