Jason Calacanis founded Silicon Alley Reporter, Weblogs Inc, Mahalo, and Inside.com.
He turned down a $20 million offer for Silicon Alley Reporter. Then the dotcom bubble burst, and he wound up with a net worth of negative $10,000. Calacanis bounced back and founded Weblogs, which he sold to AOL after 18 months for $30 million.

But most of Jason's money has been made by angel investing. He placed an early bet on Uber that paid off, and he’s now a professional investor with his own syndicate. Calacanis' new book is called, "Angel: How to invest in technology startups —Timeless advice from an Angel Investor who turned $100,000 into $100,000,000."