When Jason Calacanis declared last week that he was taking a break from blogging — shock! — it prompted an outpouring of blogging fatigue. Even Robert Scoble, the most prolix of web writers, wondered whether he'd lost his mojo. But there's a simpler explanation for the disappearance of Calacanis. The brash web entrepreneur is trying to secure a huge round of funding even before Mahalo, his new venture, is even launched, according to several sources.
We'd heard that Calacanis had ambitious plans for his video wikipedia, but had no idea he'd be this aggressive in funding Mahalo. From the various numbers floating around, our guess is that Calacanis is seeking up to $20m, at a valuation of up to $100m. The round would make Mahalo one of the most lavishly backed pre-launch sites since, um, Boo.com during the last bubble. (That didn't end well.)
One would expect that Calacanis' existing backers — which include Sequoia and individual investors such as Mark Cuban, the entrepreneur, and Fred Wilson, the New York venture capitalist — will contribute to the new round. Others lined up include Hubert Burda, one of Europe's more dynamic media moguls, and CBS, which has become one of the most active dealmakers since appointing Quincy Smith to run the network's internet division. The final line-up is still up in the air because some investors, understandably, are balking at the valuation.
In the 1990s, Jason Calacanis, then a magazine publisher, had a reputation for being sparing with salaries and equity grants — cheap, in other words — winning him the respect of investors, even as he alienated some colleagues. And, for all his bullishness about internet advertising, Calacanis can be conservative. He sold Weblogs Inc to AOL in 2005, before the weblog publishing group really began to fulfill its potential for ad revenue.
So, what changed? One possibility is that Calacanis, realizing he sold Weblogs Inc too soon, for too little, is trying to compensate by squeezing two ventures into one boom cycle. Another that he's bought into the flattering web coverage of his success with Weblogs Inc; that he's determined to dream on the scale of the mogul he's destined to become.
[Valleywag made no attempt to contact Jason Calacanis before publication. Any of the misinformation he's so relished disseminating can go in the comments below.]


















