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

Summary: <span style="font-size: 11pt; font-family: Arial; color: rgb(0, 0, 0); background-color: transparent;">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 <span style="font-size: 14.6667px; font-family: Arial; color: rgb(0, 0, 0);">Business Insider’s US Editor-in-Chief Alyson Shontell<span style="font-size: 11pt; font-family: Arial; color: rgb(0, 0, 0); background-color: transparent;"> about that experience and more for this episode of “Success! How I Did It.” </span></span></span>