"It was 1987, and my dad didn't pay his taxes," recalled Mahalo.com founder Jason Calacanis at Silicon Alley Insider's Startup 2009 competititon on Wednesday about the Brooklyn bar his father owned. "Federal marshalls came with shotguns and took the business. I was 16, and I curled up in a ball and just cried.
"I watched my dad fail when the market crashed in 1987, and the same thing happened to me in 2001," Calacanis said about the dot-com bubble burst and its affect on his first business, Silicon Alley Reporter, which chronicled the New York tech scene in the '90s.
"I was on top of the world, I was on '60 Minutes,' and then suddenly Silicon Alley Reporter went from $12 million a month to $600,000 a month, and I had to lay off 60 employees and brought it down to 10 employees.
"I thought, 'I'm not going to lose, I'm going to double-down.' Other people went to Thailand and took yoga retreats, and I thought, 'Rock on. But I'm gonna prove all those people wrong who said, Calacanis is a fraud, you got lucky, you're a hack, you can't even spell.' "
Calacanis got his revenge in 2005 when he sold pioneering blog networks Weblogs Inc. to AOL LLC for $25 million.
When asked at the Internet Week New York event by Silicon Alley Insider co-founder Henry Blodget to name three keys to success for entrepreneurs, Calacanis said:
- Resilliency. Viktor Frankl, a Holocaust survivor, writes in "Man's Search for Meaning" about why some people give up and others don't. Be stubborn and fight and fight. Don't think you're the smartest kid in class, but work hard.
- Don't overestimate the downside of risk. If you fail, you can always go back to your day job.
- Have fun with it. "I think of my career as like a video game, he said. "Just put another quarter in and hit the reset key."
We're here at Startup 2009 all day, videotaping interviews with Calacanis and others. - Mary Kathleen Flynn
