Rise of the Tech Bandits: Jason Calacanis, the Shapeshifter

Editor's note: In the Summer 2012 issue of SAY Magazine, Dan Frommer chronicles the history of tech blogging. For the rest of this week, Richard MacManus, who founded ReadWriteWeb in 2003, will be looking back on the early days.

Blog network Weblogs, Inc. sold to AOL in October 2005, for a reported $25 million. I was in San Francisco when it happened, at the Web 2.0 Conference. The morning the deal went public, I remember founder Jason Calacanis arriving at the conference with a smile as wide as the Cheshire Cat himself. He positively glowed, while basking in the congratulations and praise from fellow entrepreneurs at the event. Come to think of it, I've rarely seen Jason Calacanis without a smile on his face. It's usually a mischievous one too, because he likes to be the center of attention.

An excerpt from Dan Frommer's Rise of the Tech Bandits:

"After the crash, the Web 2.0 boom in the mid-2000s gave birth to a new batch of media startups running cheap publishing software and network ads. Free of expenses like copy editors, design staffs or Midtown offices, they told Silicon Valley’s inside story, started breaking big news and quickly caught on.
The most famous, of course, is TechCrunch, the site founded in 2005 by former attorney Mike Arrington and operated for years out of his house in Silicon Valley. (AOL bought TechCrunch in 2010 for more than $25 million.) Mashable also launched in 2005, the creation of 19-year-old Scottish kid Pete Cashmore, now drawing more readers than TechCrunch and, reportedly, with acquisition interest from CNN.[...]
The Web was finally covering itself better than its print counterparts — and independently."

The Weblogs, Inc. sale was the first high profile acquisition of a blogging business, setting the scene for future blog acquisitions like The Huffington Post, Ars Technica, TechCrunch and PaidContent. Calacanis wasn't even a pro blogger. Rather, he was the CEO of a wide-ranging network of blogs that began in September 2003. The most high profile blog under his stewardship was Engadget.

I've met Jason several times over the years and two of those times stand out. Both show aspects of Jason that I believe contributed greatly to his success as an entrepreneur.

The first instance was at a Web 2.0 Conference a few years ago. I don't recall the exact year, but it was during the time Calacanis was running his post-AOL venture Mahalo. I was at an official conference dinner, along with Sean Ammirati (before he became COO of ReadWriteWeb). The table Sean and I were seated at had about 10-12 people. Everyone picked at their starch-heavy plates of food, while engaging in the usual conference chit-chat. Which meant asking or answering these two questions: "And what do you do?", closely followed by "What's been the highlight of the conference for you so far?". This typical, rather placid, conference dinner scene was playing out, when out of nowhere a grinning Jason Calacanis approached the table. He immediately began to regale Sean and I with several funny stories, delivered rapid fire one after the other in his broad Brooklyn accent. It was highly entertaining, but it wasn't a conversation as such... more of a comedy routine. Before either Sean or I had a chance to get a word in, Jason had moved down the table to entertain another group of people. Soon he gravitated to the next table - and all we heard then was appreciative laughter from his new audience.

That's an uncommon skill, to be able to get and hold the attention of multiple groups of people at a social event.

The second story of Jason I have is when he spoke at ReadWriteWeb's 2WAY Summit in New York City, in June last year. Jason had been scheduled to have a debate with his long-standing rival, Gawker CEO Nick Denton. It was a mouth watering prospect, because both men are opinionated and successful media entrepreneurs. Unfortunately, Denton pulled out at the last minute. Jason not only turned up, but turned his one-man interview with our Managing Editor Abraham Hyatt into a highlight of the event. It was entertaining, opinionated and highly quotable ("There are a lot of stupid people out there ... and stupid people shouldn't write.").

The Internet industry often takes itself too seriously. It feels good to have someone brighten up your dinner table every now and then.

SAY Media is ReadWriteWeb's parent company.