The Rise and Fall and Rise of Jason Calacanis: In His Own Words



“Millennial parents told you, you can be anything. You can be President of the United States! Statistically, no you can’t. You can’t be President. Most Presidents have two terms. That’s eight years, which means that’s just a few people who are going to be President in your lifetime. So no, you’re not going to be President. People have these unrealistic ideas that they’ll be popping bottles (meaning champagne), but (it’s not going to just come to you). You need skills. If you’re hard working, you’ll figure it out.”

Jason Calacanis doesn’t mince words. Never has. No doubt ever will.

Calacanis is not your typical angel investor (Blippy, Gowalla, ChallengePost, Chartbeat, SmartyPants, Uber). Or entrepreneur (Silicon Alley Reporter – sold to Dow Jones; Weblogs Inc,  – sold to AOL; barely got into, then out of Fordham University). Or guest speaker, for that matter. A master showman, conference organizer (LAUNCH) and interviewer/host (TWIST), Calacanis pretty much interviews himself. Which is exactly what he did when he took to the podium with The Phat Startup in New York City.

This is his story and he’s sticking to it.

LA based, Calacanis is New York City born and bred (“Bay Ridge; I took the N & R train into the city. The Never and the Rarely”). His dad was a bartender, his mother a nurse, and Jason was a less than spectacular student. Graduating from high school with a 70-odd average, he begged his way into Fordham, then struggled for five years to finish.

The fact that his father’s business took a turn for the worse, and the marshalls “came with shotguns and took everything” – including Calacanis’ tuition money – just as he was about to start college, didn’t help.

“I worked as a waiter and a bar back, but I knew how to fix computers.”

Which he did, earning minimum wage, until he was caught partitioning hard drives, so he was fired.

“I was running scams on the side,” he shrugged nonchalantly. “Selling Word Perfect for $20.”

As luck would have it, he happened to be in the school cafeteria one day, sitting next to the guy who ran the business center – who’d heard about Calacanis’ being fired. Knowing that he knew something about computers, he hired him to do support for the business school.

“He offered me $6.50 an hour, but I acted like I had other offers. So he offered me $7.50 an hour,” thus doubling the salary he’d recently lost.

He ended up at Sony, just when the Internet was starting to hit, which was basically a later iteration of Arpanet, which he was familiar with from school. So he’d set up Sony executives’ computers to access the Internet.

“The computers didn’t even have Ethernet cards in them.”

A a self-described nobody at the time (see his LinkedIn profile, and a nobody, by his definition, is someone who’s riding the D train at night to commute back to his apartment in not-Manhattan), he happened to get onto an elevator with then Sony chief Tommy Mottola and his bodyguard (big no-no), and had his first brush with real power and decided that that was for him. Now he just had to figure out how to get there.

It didn’t happen when he was out in California on business with Sony and was invited to fly back to New York with then Sony chief Mickey Schulhof on the private company jet. He happened to be carrying a copy of Nicholas Negroponte’s then recently published, “Being Digital.”

“What do you think of the book?” Schulhof asked.

Calacanis found it interesting, but a bit simplistic.

“I’ll tell my friend Nicholas that you called his book simple,” said Schulhof.

Yeah, that’s a ‘do not pass go.’

Schulhof did ask him his advice about that Internet thing, and Calacanis suggested that Sony buy either Yahoo! or Lycos, which of course fell on deaf ears but at least he got a free ride back on the Sony Pony.

His first real break came when he met Fred Wilson and Jerry Colonna, investors with a fund called Acme Ventures, who were also curious about the Internet.  They’d pay him $1k a month to read business plans. Done!

“I didn’t know how to read business plans,” said Calacanis. “But they didn’t know the Internet, either. When no one knows what the fuck they’re doing, you fake it.”

Which is when he struck upon his own million-dollar idea: Silicon Alley Reporter.

He wrote articles, learned PageMaker and printed the copies himself, courtesy of his first two investors: his Amex and Visa cards.

“I was too stupid to be embarrassed about spelling errors. There was something going on in the world that I knew about and people wanted my knowledge,” he said.

The distribution model: he packed the black and white first edition into a luggage cart and put it wherever he saw the Village Voice and Time Out being distributed.

“Bill Rudin bought the back cover,” he said. For the second edition, he went to color, and it wasn’t long before he was getting $20K in advertising and charging $100/year for a subscription.

“I was taking in a thousand, two thousand a day,” he exclaimed.

He wasn’t on the D train anymore. Next plan: figure out how to be the most influential guy in Silicon Alley. Which is why he struck upon the idea for the Silicon Alley 100 – the 100 most influential people working in and around the Internet in NYC.

“We got to 50, then called them to see who they’d recommend, then added those people, too.”

#1 was Esther Dyson, followed by the DoubleClick guys.

“We decided everyone gets a number and every year we’d see how many spots they went up or down.”

All of which was at Calacanis whim and discretion, but then, he was not one to shrink from controversy: in fact, he openly courted it.

Having seen his father fail, he told himself he’d never fail and things were good. In fact he was one of five tech visionaries tapped to be profiled in a book on the subject.

Then the dot com bubble burst and 9/11 hit.  Calacanis pretty much lost everything.

“I was a nobody again,” he said. A year before, Alan Meckler had offered him $20 million for SAR (he turned it down). Now he sold it to Dow Jones for the bargain price of two years’ salary and $100k.

He was back on the D train. That book did come out and he was profiled – as one of the five people who had caused the dot com crash.

“Having made the lists, knew it was all bullshit,” he noted. “The Top 30 Under 30? They’re just making it up, just trying to tweak people. I knew I could do it again,” he said, meaning, being on top.
“People who worked for me started blogging in 2001, 2002. Rafat Ali was doing Paid Content. I told him he was wasting his time. I was high on my own supply.”

But he saw something in the bloggers: they were the people who were unmanageable, who liked their raw voice more than they did traditional journalism.

“It was like the birth of punk,” he observed, and decided that this “blogging was going to be the shit. They just needed editors, like me.”

Eighteen months later, he had four employees and 500 bloggers on his Weblogs platform, and was taking in about $30k a month when Ted Leonsis from AOL called, desperate to buy the company.

It wasn’t quite the halcyon days of Internet 1.0, when rank startups with hefty price tags were being snapped up as if there was a fire sale. Only Flickr and del.icio.us had been the only recent acquisitions.

Friend and longtime advisor Mark Cuban had once coached Calacanis on negotiating, telling him to open with, ‘You guys have a number in mind. You guys should put a number out there.’ Calacanis tried that approach, but AOL didn’t blink.

Neither did Calacanis.

“’Mark said he wants to put in another million, and we’re talking to Jeff Bezos,’” Calacanis bluffed. “I’m thinking $40 million.”

“We were thinking more like $30 million,” Leonsis responded.

Calacanis had gone from living month to month, to realizing that his mom never had to work again.

“It’s never about the money,” the entrepreneur cautioned. “It’s about fulfilling your dreams. I realized I never had to work again and now I was really going to be dangerous.”

The day after the deal closed, he was The Man again.

“People who communicate well – they have a lot of power. Write one hour a day and respond two hours a day,” he advised. “You get 100 followers, no one cares. You get 1000, you get their attention. You get 10,000 and they’ll kiss your ass.”

His current focus is on the real world: what’s going on off screen – the Ubers and the Airbnbs of the world. He’s interested in people looking at every aspect of our lives and making it not suck.

“People are still underestimating mobile,” he continued, “and wearables still have a ways to go. It’s still nascent and Google Glass is still a bit of a disaster. VR is still not ready for prime time. People want to be in reality.

“It’s about how simple can you make it, and how easy is it to use. You get a reset,” he noted. “Everything’s up for grabs again. It’s all up to you. Everyone’s product is shitty at first. Keep iterating. You’ll get lucky, but you make your own luck.

“Mahalo failed. Then I picked Uber,” he continued. “I’m no smarter than anyone else. I had a 70s average in high school – but Fordham and Harvard ask me to keynote! You just keep hustling. Keep working. Keep trying. That’s the difference between who’s successful and who’s not.”

About the author: AlleyWatch

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