Jason McCabe Calacanis = Bubble 2.0

Does the fact that Jason Calacanis — of Weblogs Inc. — is successful again mean that we’re in another Web bubble? For many people in Silicon Valley in the late 1980s, Jason was a dot-com poster boy, as a profile in Wired points out. He built a photocopied and hand-delivered gossip sheet into an industry-leading magazine, and also had a reputation for throwing lavish parties. (Wikipedia has the abbreviated version of his bio).

Now, Jason works for AOL, which paid an estimated $25-million for his network of about 80 blogs. While that seems like a large enterprise, only a dozen or so of those blogs — such as Engadget.com and Joystiq.com — appear to get much traffic, and according to the Wired article the company had about $1-million in advertising revenue when AOL bought it. As the piece notes, “it’s not clear that $25 million is a sane amount for 10 disconnected employees and a network of bloggers who could jump ship at any moment.” That’s putting it mildly.

In typical Calacanis fashion, he isn’t content to bask in the glory of a bubble-style takeover of his company — he’s convinced that he could become chief executive of AOL if he wanted to (an idea that, sadly, might not be as much of a stretch as it should be). Paul Kedrosky gives Jason props for bouncing back from his first popped bubble, but others will likely see his return as evidence that the bubble mentality is back with a vengeance.

Don’t buy blogs — partner with them

It hasn’t been that long since America Online bought Jason Calacanis’s Weblogs Inc. stable for a reported $25-million (U.S.) — and now comes another deal that is the polar opposite. From whom? None other than Jason’s old nemesis and polar opposite himself, Nick Denton of Gawker.com and Gizmodo.com and so many other great blogs. When Jason sold his company and became part of AOL, Mr. Denton made it clear that he thought that was a mistake, and many seemed to agree — and so instead of selling, Nick has partnered with Yahoo to distribute his blog postings from a number of blogs through various Yahoo hubs (the news comes via buzzmachine.com and before that via paidcontent.org).

As the ever-astute Jeff Jarvis of buzzmachine.com points out in a post on the topic, Nick’s choice seems to be the smarter of the two. Yes, the Weblogs Inc. team cashed in for a big payout, but for a blog network it seems to make much more sense to piggy-back on the distribution and marketing of a giant such as Yahoo or AOL, not get swallowed up by it. As Scott Moore of Yahoo tells Rafat Ali at paidcontent.org, the move is part of a strategy to become “more blog aware and blogcentric,” and it is not an exclusive deal, meaning Gawker Media can do similar deals with others. For what it’s worth, I would vote with Nick on this one. Susan Mernit seems to like it too.

Update: Jason Calacanis has posted his thoughts on the Gawker/Yahoo deal, and he says it’s great news for the medium. He also notes that his deal with AOL allows him to do distribution deals with whoever he wants — which may be true, but ownership is still different than partnering.