How a founder went from being worth millions to -$10,000 almost overnight — then rebounded to a $100 million fortune – Anna Mazarakis and Alyson Shontell August 4, 2017


Success How I Did It podcast

Samantha Lee/Business Insider

Jason CalacanisJason Calacanis is an investor and the author of the new book “Angel.” Flickr/Joi Ito

  • 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.”

When Jason Calacanis was just a scrappy kid from Brooklyn in the late 1990s, he built a thriving magazine called Silicon Alley Reporter. At the magazine’s peak, he was offered a $20 million buyout offer. He turned it down, and shortly after, the dotcom bubble burst. Calacanis wound up selling the magazine for next to nothing, and then got fired.

“A year earlier I’m on Charlie Rose, I’m in the New Yorker and I’m getting offered $20 million,” Calacanis said during an interview for Business Insider’s podcast, Success! How I Did It. “All my power and money got taken away from me again. I was really like, “Am I a fraud? Did I just get lucky? Is the Internet a fraud?”

Calacanis went on to start Weblogs and sold it 18 months later to AOL for about $30 million. But he’s made the most money as an angel investor. He was one of the first investors in Uber, which was last valued at about $69 billion.

Here’s how Calacanis, a broke kid from Brooklyn, became rich, blew it, became rich again, and then made a $100 million fortune. You can listen to the full interview with him on “Success! How I Did It,” here:

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