No. 22

No. 22

Naval Ravikant, 36
Founder, Chairman, Vast.com
Blog: Startup Boy

No. of Angel Investments: 21
Companies funded (a sampling):
Chatterous, DotSpots, Fluther, Twitter, Vidly

Like a lot of top angels, Naval Ravikant has a long list of companies to his credit. He is founder and chairman of Vast.com, a search platform that optimizes inventory in its partners’ online marketplaces for autos, real estate, and vacation rentals. He founded Epinions.com, a site that offers product reviews and buying guides—and is now owned by comparative pricing service Shopping.com. He co-founded Venture Hacks, a site that shares advice for startups. And he has advised other startups, including Bix, iPivot, and Xfire.

As for his investing philosophy, he says the best companies to have invested in are the ones that have the most entrepreneurial and talented alumni. "A successful investor doesn't just own a piece of a company—he or she owns an early look at all of the spinouts and ventures from there," Ravikant wrote in an e-mail message. If he had the opportunity to travel back in time, "I'd favor investments in Hewlett-Packard, SGI (Silicon Graphics), Netscape, Google, and Facebook—all of which had strong and successful alumni networks—over companies in a different geography (Microsoft) or ones with a smaller history of doing spinouts (Apple)."

Excluding his own portfolio, he says two companies at the angel stage that he thinks have "moon shot" potential are Dropbox, a file sharing service, and "Quora&emdash;an ex-Facebook team that has flawless execution." [Quora is a site that offers user-generated Q&As.]