The first thing Mahalo CEO Jason Calacanis did when approached by a reporter at the TechCrunch50 conference last week was issue an invitation to an impromptu poker match. “Do you want to come and be a cocktail waitress?” he asked.

No thank you, no sale — which was a rare failure for a man who has made a career of selling anything.

From the roller-coaster Silicon Alley Reporter, which rose up and crashed in the first dotcom bubble, to the sale to AOL of Weblogs Inc., to his newest venture, Mahalo, and side gigs like being master of ceremonies and co-founder of the annual TechCrunch conferences in San Francisco, Calacanis has muscled his way to success. As his waitress crack exemplifies, he’s also known for being brash.

Calacanis is the most influential Internet entrepreneur in Los Angeles. From his Twitter feed, you would also know that his dogs are named Fondue and Taurus, that he made duck confit for dinner last Wednesday, that he attended a party at Paris Hilton’s mansion and that he drives a $109,000 Tesla roadster. That’s the way Calacanis rolls — transparentlike — and with enthusiasm that teeters precariously between ridiculous and genius.

His newest start-up, Mahalo, officially launched in 2007. Many people would describe it as an alternative search engine, but Mahalo is actually an outgrowth of the fourth “curatorial” stage of the Internet — a venue for editorial content, which boasts more than 277,000 results pages. It is not so much a Google as an ad-driven Wikipedia. Calacanis says he is “not worried about what people call it,” he just hopes it’s “superhelpful.”

Mahalo is a community where “membership is a privilege, not a right,” he adds. The site has more than 10 million unique users, according to It features the melding of three technologies: a search engine, an ad-driven encyclopedia and a moderated community answers portal, called Mahalo Answers, which Calacanis has dubbed “the killer app.” Mahalo users now can e-mail questions via their phones to, and receive an answer in 20 to 40 minutes.

Immediacy and transparency are crucial parts of the Mahalo culture. Calacanis even ranks his editors by assigning them virtual karate belts: white, yellow, green, purple, brown and black, which is of note, given that Calacanis has a black belt in Taekwondo.

His ceaseless self-promotion has made him one of the most polarizing figures in tech. But it’s hard not to respect or even like him, because his artless outsider persona belies an extremely sharp entrepreneurial mind, inspiring to those who recognize the power of passion and perseverance.

Calacanis was born in Bay Ridge, Brooklyn, and started his career in Silicon Alley, NYC, but this firebrand/visionary/iconoclast seems perfectly suited for the anything-goes atmosphere of sunny L.A.

As founder Kevin Rose said, “Jason is not BSing.” It’s hard not to bet on Calacanis winning his hand, which investors, including the prestigious Sequoia Capital of Google and YouTube fame, did to the tune of more than $20 million.

He’s played executive through the rise and fall of Weblogs Inc., Netscape and AOL. Not bad for someone who started his career as a journalist. “Sometimes I dream about being a writer again,” he says. He compares his position as CEO to that of a director telling a good story: Both must focus primarily on making “a product people love.”

Calacanis currently has a supporting role in Ondi Timoner’s documentary We Live in Public, about fellow Internet vanguard Josh Harris; it won the Sundance Grand Jury prize and opens at the Nuart Theater on Friday.

Calacanis describes Los Angeles as a “great place to be an entrepreneur.” Mahalo is currently one of the city’s fastest-growing tech companies, providing regular employment to aspiring actors, models and writers, who ensure that links function relevantly and that the results pages remain free of spam and inappropriateness.

Wrangling the static and spam of search content into something more or less useful is a formidable and unoriginal task, which pushes him into the ranks of the true American entrepreneur, much like Ted Turner or even Bob Dylan, whom Calacanis often references.

But it is perhaps a Web 2.0 revamp of the Kenny Rogers song “The Gambler” that most exemplifies the Jason Calacanis school of business: “You got to show when to hold ’em, show when to fold ’em. .”

All we can do is wait, and follow his tweets as he plays the game.

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