Live from SES Chicago: Calacanis Signs with Sequoia

Posted on by Chief Marketer Staff

Jason Calacanis, who departed a post as general manager of AOL’s Netscape division in mid-November, told an audience at Search Engine Strategies Chicago 2006 that he will join the venture capital firm of Sequoia Capital as “Entrepreneur in Action”.

Calacanis came to the AOL division of Time Warner when he sold his blog network start-up Weblogs Inc. to the company late last year for a reported $25 million. Calacanis served both as head of the Netscape unit at AOL and editorial director for the Weblogs product. But when AOL chairman and CEO Jonathan Miller was let go last month, Calacanis told the SES Chicago crowd, “I said, ‘This was my guy, he was really good to me, life’s too short, and I’m going to move on to the next thing.’”

“I didn’t have to stay at AOL at all,” he says. “When you hire a blogger, it’s a bad idea to upset them by making them stay for three years or whatever. It’s a bad combination: big company, angry blogger.”

While heading up Netscape for AOL, Calacanis caused a stir by offering to hire away some of the most prominent users of social bookmarking site Digg.com and pay them to create a similar bookmarking community on Netscape. He was accused of subverting the social bookmarking trend by adding salaries.

But Calacanis says he was simply trying to draw those committed Digg users who were working long hours on the site without pay, discovering content they thought was worth bringing forward for others to see and bookmark.

“We said, ‘Gosh these people really have some knowledge about the space. Why don’t we pay them $1000 a month to submit 150 stories, but they can pick whatever stories they want? We exerted no editorial control, with one exception: They couldn’t be getting paid to put the stuff up there.”

Calacanis says that while the initiative may have been a PR setback, it has been an operational success at Netscape. He said the Diggers who’ve come over have made substantial suggestions that make the site easier to use and have also helped with one of Digg’s biggest problems: consolidating duplicate submissions, with multiple users submitting the same story from different media outlets.

The new post with Sequoia “basically means I’m going to build another company with Sequoia Capital,” Calacanis said. “Now I just have to figure out what to build.” Sequoia was an early investor in Apple Computer, Cisco Systems, Google, Yahoo!, YouTube and a number of other prominent Internet firms back in their start-up days.

He said recent blog posts that reported he was thinking about an MP3 player that could detect Wi-Fi networks and download podcasts automatically were only partially correct.

“I was blogging late one night about things I might do next, and I started writing random things: play professional poker, start a podcasting business or a blogging business or a wiki media business,” he said. “And I added a throwaway one: ‘Create a DRM-free MP3 player designed for podcasting.’” The post got picked up by fellow bloggers as a viable idea, and now Calacanis says he’s getting e-mail from Chinese manufacturers volunteering to tool up and build the units.

“It was actually a less serious idea than becoming a professional poker player,” Calacanis says. “And I’m not a good poker player.”

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