50. Brian Wiegand
Founder and CEO
Launched: October 2012
What We Like: New word: crossvesting. Six years after selling Jellyfish to Microsoft for a reported $50 million, he and co-founder Mark McGuire are investing in each other’s latest ventures. Wiegand’s angel investing in other young companies as well. Also cool: Two former Jellyfishers, Mark Wilson and Aaron Everson, launched their own, TermSync and Shoutlet, respectively. “Once you have a couple successes it really spawns more successes,” says Wiegand.
Bragging Rights: His fourth venture, Alice.com, isn’t one of them, having shuttered in August. But here’s the thing: On average, only one out of ten startups succeed, so statistically speaking four out of five says, yeah, he struck out at his last at-bat, but he’ll likely still land in the Startup Hall of Fame.