Investor Jason Calacanis: How I was broke, then rich, then broke, and now have $100 million

Jason Calacanis founded Silicon Alley Reporter, Weblogs Inc, Mahalo, and Inside.com. He made an early bet on Uber that paid off, and he’s now an investor and has his own syndicate. But he had a hard time getting there, including a huge fall from grace when the dotcom bubble burst. Back then, he was worth negative $10,000. Now, he's clawed his way back and generated $100 million. Calacanis told Business Insider’s US Editor-in-Chief Alyson Shontell about that experience and more for this episode of “Success! How I Did It.”