What looks better on a millionaire:

* The poor guy that invested every cent he had and kept slaving away for years every day at the brink of certain failure.

* The rich kid that got several hundred thousand from his parents for his first company and knew exactly that failure just meant asking his parents for another go or having to switch to a management position that has probably been waiting for him since he was five?

Of course the first one looks better, you can also bet that any millionaire telling it is a habitual liar that paid a good sum to have some PR guy find ways to navigate around his actual rich kid background without looking too obvious about it.