Man vs. Machine
August 18, 2007
t’s a sunshiny summer day–Californians just call it “weather”–but Jason Calacanis is air-conditioned cool in his new Santa Monica HQ. He’s hosting his weekly audio podcast, CalacanisCast, which gets upward of 30,000 listeners a week. Addressing call-in guest Brian Provost, a “search-engine optimizer” who gooses Google search results for a living, Calacanis recalls “a seminal blog post. I think it was ‘Jason Calacanis: Charlatan Douche Bag.’”
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Flippant Calacanis strikes a typical pose.
Search Central Mahalo’s headquarters in Santa Monica, California, is currently home to 40 “guides” who build search results by hand.
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“My favorite,” says Provost.
“You also said you were going to knock me out at one point,” Calacanis adds.
“Nah, I said I was going to cut somebody a check if they knocked you out.”
Calacanis smirks. Barely 5-foot-9, the 36-year-old serial Web entrepreneur is a black belt in tae kwon do who grew up in the famously gritty Bay Ridge section of Brooklyn, where violence was as ubiquitous as graffiti. As a kid, he was tossed out of school for fighting and mopped blood off the floor of his father’s bar; his mother, an emergency-room nurse, would stitch up the combatants at a local hospital. It was a real family affair.
He introduces his next guest as the author of “Don’t Trust Jason Calacanis.” Then he welcomes a third search-engine optimizer, or SEO, Andy Beard, who dialed in from Poland. “You’ve written some great ones,” Calacanis tells him. “Like ‘How to Build a Biased Self-Propaganda Machine.’ A classic, classic post …”
It was, Beard says, “probably one of my most favorable posts for you.”
“One of your nicer ones,” Calacanis agrees.
It’s all so convivial, made more remarkable by the fact that they all can’t stand him. But you can’t blame Calacanis’s guests for wanting to stick it to him. He routinely blogs about his plan to put them out of business, calling SEOs “slime buckets” who are nothing more than “snake-oil salesmen” and “low-class idiots” who are “polluting” the Internet with “spam” sites. They are the ones responsible for “index spam,” which, at its worst, tries to trick search-engine Web crawlers so that a page about romantic holidays in Bordeaux ends up redirecting users to a site where they can purchase Viagra. For Calacanis, the junk they push is the equivalent of the penile-enhancement and penny-stock scams that clog your email inbox.
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To take these guys down, Calacanis is betting on his new online search engine, Mahalo (”thank you” in Hawaiian), which recently rolled out with $20 million in venture capital from a bevy of blue-chip investors–Sequoia Capital (original backer of Yahoo and Google); News Corp. (NYSE:NWS); CBS (NYSE:CBS); maverick Mark Cuban; and Elon Musk, the founder of PayPal, SpaceX, and now chairman of Tesla Motors, builder of the $100,000 iPod of electric cars. That high-tech breeding stock notwithstanding, Calacanis’s new venture is pure old school. He’s not unleashing some spicy new algorithm to power Mahalo. He’s using people. The company’s motto: “We’re here to help.”
Of course, hiring humans to do a machine’s work may seem more Web minus 1 than Web 2.0. But people know what other people want in a way a math equation can never intuit, like getting a living, breathing voice instead of an automated call system when you dial tech support. And for SEOs, it’s a lot harder to fool flesh and blood than to snow a machine.
At the end of the radio show, Calacanis wagers his “gray hat” guests they won’t be able to insert a “spammy link” in Mahalo.
No one will take him up on it.
And that’s the thing about Calacanis. Only a sucker would bet against him.
Not everyone hates Jason Calacanis, although for those who follow the latest skirmishes in the blogosphere, it may seem that way. The former publisher of Silicon Alley Reporter (it crashed and burned with the dotcoms) and the man behind Weblogs Inc., the blog syndicate he sold to AOL for a chill $25 million two years ago, welcomes any and all comers to the round-robin slugfest that is his online life. He posts his cell-phone number and email address on his blog, priming the flow of conflict. Not even his bosses are spared: While an executive at AOL, after the Weblogs purchase, Calacanis publicly advised his bloggers to quit if their new corporate parent tried to censor them–and bashed AOL’s own search engine, calling it “bad, very, very bad” from a user’s perspective. And he was right.
Calacanis’s archrival, Gawker Media tycoon Nick Denton, once described him as “brash,” “ballsy,” “publicity-hungry,” and “the Web’s answer to Donald Trump,” all in the same paragraph. Calacanis prefers to think of himself as honest, authentic–and there’s truth to that. He may dish it out, but he’s admirably thick-skinned, a necessity in the Hobbesian world of blogs, with its nasty, brutish, and short commentary. Calacanis is indeed transparent, but not only in the sense that his motives are clear (they are: He wants to get rich enough to buy the New York Knicks), but because he doesn’t hide what he thinks. As perennial pal Douglas Rushkoff, author of Get Back in the Box: Innovation From the Inside Out, puts it: “Jason would never stab you in the back. He might stab you in the face, though.”
The Calacanis saga has been rehashed so often it’s like a Web junkie’s version of E! True Hollywood Story. Calacanis is the working-class kid who started a grimy, 16-page, black-and-white newsletter, The Silicon Alley Reporter, that he’d stuff into newsstand racks when no one was looking. Early on, he realized there might be a healthy business in providing publicity for New York’s burgeoning tech community. And in a dazzling display of catch-22 logic, he knew if these Alley dotcomers became important, he would too–because he would be deciding who was important. His cynicism paid off nicely: Within five years, he was pulling in nearly $12 million in revenue.
With the money pouring in, Calacanis became a schmoozer nonpareil. He rented a loft, threw parties, organized conferences, and published a West Coast version of the magazine. Both Rushkoff and Calacanis held season tickets to Knicks games, Rushkoff sitting a dozen rows in front of his friend. But the ever-restless Calacanis never stayed in his seat long. “He’d start out the first quarter sitting behind me,” Rushkoff recalls, “but he’d invariably see someone he knew–a dotcomer, venture capitalist–and by the second quarter would end up sitting in front of me.”
By January 1999, as the market was about to peak, Calacanis and Rushkoff sat next to each other on a plane. Calacanis had just been offered $20 million for the Reporter and its associated conference business. But he was torn. Not yet 30, he was still a true believer.
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