"Jimmy Wales started his search company a year ago, and he was on the cover of Fast Company saying he's going to kill Google, and then he gave up after 11 or 12 months," says provocative serial entrepreneur Jason Calacanis, referring to the co-founder of Wikipedia in this episode of The Deal's Behind the Money video show. "That's not being an entrepreneur. That's being a poser." "I think you have to fight the fight for years and not give up; so I don't have a lot of respect for people who give up," Calacanis (pictured) tells The Deal. "I have a tremendous amount of respect for people who fight and fight and fight and then fail." Calacanis is no stranger to failure. As a teenager, he watched federal marshals show up with shotguns and close his family's bar in Brooklyn after his father failed to pay taxes. "I was 16, and I curled up in a ball and just cried," Calacanis told Silicon Alley Insider co-founder Henry Blodget at Startup 2009 on Wednesday, a few minutes before we interviewed Calacanis. When his media company Silicon Alley Reporter crumbled in 2001 along with the New York dot-coms it chronicled, he watched other founders go on yoga retreats, but he kept his nose to the grindstone. His efforts paid off in 2005 when he sold his pioneering blog network Weblogs Inc. to AOL LLC for $25 million. These days, Calacanis lives in Los Angeles and focuses on his search startup Mahalo.com. He demonstrated a new version of it at the NY Tech Meetup showcase for Internet Week New York on Tuesday evening. "I'm bullish on Silicon Alley, more than ever," he told The Deal, pointing to the mix of seasoned Internet entrepreneurs and talented 20-somethings here, including Kevin Ryan, co-founder of AlleyCorp, and John Borthwick, co-founder of Betaworks, in the first category and David Karp, founder of Tumblr Inc., and Charles Forman, founder of OMGPOP (previously known as Iminlikewithyou) in the second. Watch the video below or download it on iTunes. - Mary Kathleen Flynn
