So what I'm hearing is that tenacious Steve failed a bunch of times before he finally hit one out of the park. Sounds like an entrepreneur to me.
"Founders today will not have the opportunity to learn the lessons Jobs did because they don’t have the resources and klout that Jobs had." Jobs was a millionaire when he failed a bunch of times and lost all his money. Are you a millionaire?
Work within your means, but reach for things that are out of your means.