Dylan Smith co-founded Box, a storage company that's poised to be Silicon Valley's newest public company. Smith will make tens of millions of dollars (at least!)—perhaps enough money to erase his cringe-attack reality show moment from the internet.

In 2010, baby-faced Smith, originally created in the same laboratory as Mark Zuckerberg, was looking for love. Tinder hadn't yet been invented, so he of course turned to Bravo for a slot on Millionaire Matchmaker, a popular TV morality play wherein awful people are arranged to proposition each other for sex. At least he gets a kiss in the end.

This will either remain a lifelong embarrassment for Smith, or Bravo stardom will be considered the next prerequisite for startup success after being white, young, male, and uncomfortable around others.