Jason Calacanis' next venture

Jason Calacanis, the publishing entrepreneur who sold a group of weblogs to AOL for $25m, has enjoyed sowing confusion about his plans. We've been fooled ourselves. There was the rumor run by Valleywag that the avid podcaster intended to hire Don Imus, another hint that he was drawn to online video. As an entrepreneur-in-action with Sequoia, whatever that term means, the hyper-active exec said he was wading through business plans submitted to the Silicon Valley venture capital firm. He announced a conference joint venture with Michael Arrington of Techcrunch. But several people, in a position to know of his plans, say these schemes are at most hobbies, or pure disinformation; the next venture is a search engine.

Calacanis, we hear, has already hired about 20 engineers to work on the project. Begun in the poolhouse of his Santa Monica home, it recently moved to an office nearby. Sequoia isn't merely giving him shelter while he comes up with a new idea; Roelof Botha, Calacanis' patron at Sequoia, has already committed the funds. Former associates of Calacanis, such as Mark Cuban and Jonathan Miller, his former boss at AOL, are also backing the venture.

So what's the idea? It's a cross between Wikipedia and Google. Calacanis' new site will create more digestible search results for popular queries such as the names of Hollywood stars, and tech products. The pages will be seeded, initially, with content gathered automatically from the web and other sources. But they will be open to contributions by readers. Sounds like Wikipedia? Yes: except Calacanis will employ paid editors to oversee the pages.

The project makes perfect sense for Calacanis.

1. Money. The bust came before Calacanis could cash out of Silicon Alley Reporter, his first startup. The establishment of Weblogs Inc, and its sale to AOL, restored his entrepreneurial reputation, but didn't make him as rich as poker buddies such as Jeff Dachis, founder of Razorfish. Calacanis wants to make serious money out of his next venture; he has told people his next venture will be the biggest thing he's done. He's too savvy to bet on podcasting, for which there's no significant advertising; he's long been fascinated by search marketing; of course he would address a big opportunity, and there is none bigger on the web.

2. Paid editorial. In building a blog group, and in the work he did for Netscape, Calacanis has always believed in paid editors. Remember, he comes from a traditional publishing background. It's a pattern: take a concept which relies on volunteer labor; copy; and professionalize. When running Weblogs Inc, the weblog group he sold to AOL, Calacanis, like Gawker Media, typically hired bloggers who had previously written for fun, and for free. In copying Digg's voting system on news headlines, when at Netscape, Calacanis hired away some of the top unpaid contributors to the social news site. He's already criticized Wikipedia, the collaborative encyclopedia, for its reliance on uncredentialed editors; it would be entirely consistent with his fast follower's strategy to copy Wikipedia, poach its top editors, and pay them.

3. Blogging. Calacanis is bound, I believe, still by the terms of a non-compete with AOL, so he can't simply replicate the blog network he sold to the Time Warner internet company. But the pages of his new search engine, if frequently updated with news, reader comments, and editorial write-ups, could end up looking much like topic-specific blogs. It's a good way for Calacanis to apply what he knows about lightweight publishing, without obviously retracing his steps.

So, the big question: will it work? One person who's seen a prototype describes it as labor-intensive — "very web 1.0." And even one of the former blog mogul's fans says: "It is extremely ambitious, and it will probably fail." The field is crowded, with companies such as Wikia, a new venture from the founder of Wikipedia; specialist search engines such as Spock; and established "human" search engines such as About.com, owned by the New York Times. Above all, Google itself is gradually enriching its main search results with content such as news headlines and images — and purging other search engines which sneak into its results.

But I wouldn't count out Calacanis. For a start, as we experienced at Gawker Media, he's a ferocious competitor. He loves the smell of battle. Second, there's a limit to the potential of user-generated content. The pool of volunteers is limited. A web 1.0 approach, hiring a team of editors to manage user-generated and aggregated content, sounds sensible, rather than backward. And is it foolhardy to go up against Google in search? Of course the field is crowded, and competitive. But that's because it's so profitable. Search marketing draws the ambitious entrepreneur, such as Calacanis, much as banks do robbers: that's where the money is.

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