Silicon Alley Dreaming: Ex-Blog Mogul Jason Calacanis Wants to Make You an Offer

Mr. Calacanis. (Photo:

Three months ago, the Transom broke some news to Jason Calacanis, former publisher of the New York-based dot-com bust chronicle Silicon Alley Reporter. Mr. Calacanis was sitting in the corner of a South By Southwest party, contemplating whether he could use the edge of a table to open a Heineken, when we told him his former employee Josh Topolsky had just quit as editor of the popular AOL-owned tech blog Engadget. “What?!” Mr. Calacanis said, lunging for his BlackBerry: “Hey @joshuatopolsky,” he tweeted. “I have a blank check here with your name on it. Let me know where to send it.” He sat back and took a smug swig; a server had opened the bottle. “I love making public offers,” he said. “It’s win-win. If they take it, I win. If they don’t take it, I win because it’s baller.”

Mr. Topolsky didn’t bite. Instead he and at least five Engadget bloggers signed on to a new venture backed by Jim Bankoff, who while at AOL coordinated the purchase of Engadget and its associated blog network, from Mr. Calacanis.

Mr. Calacanis was in town for a tech conference last week (not the Webbys—“I can’t believe that’s still going on”) and we met him again in a corner, this one at the W in Midtown, where his beverage, coffee, presented a different challenge, a fly. “I was like, oh my God, do not worry about it. Do you know how many flies are in this bagel? I don’t care,” he told the Transom, stirring.

“It really is a major red flag for AOL that you can’t keep a group of five or six bloggers happy,” he said. “Like velociraptors, the most dangerous dinosaur that ripped people up in Jurassic Park? If you have like a pack of those that work for you, you don’t have to tell them, go kill that. All of a sudden they’re just like, ‘What? There’s something there?’ They pounce. They just go kill it. You just have to keep them fed, that’s it. If you don’t fuck with it, they’ll do an amazing job… Of course they left because of meddling. They wouldn’t say it publicly but they told me AOL was meddling too much.”

We asked if there were any bloggers he wanted to offer a job via the Transom.

“I’m actually keen on landing Erick or MG from TechCrunch,” Mr. Calacanis said, citing another tech blog which recently sold to AOL. “I’m fairly certain they owned less than two and one percent respectively of TechCrunch when it sold. I’d offer them much more than that and get them their big pay day.”

Blogging is “largely dead” though, he said.

The Wall Street Journal had a story recently that said texting was dead, we noted. Mr. Calacanis agreed.

Is anything else dead? we asked.

He cocked his head, thinking. “Mm, not sure,” he said. Silicon Alley Dreaming: Ex-Blog Mogul Jason Calacanis Wants to Make You an Offer