1-on-1 with Jason Calacanis: $10K

Asked whether his new venture will take on Blogads.com, Jason Calacanis responded, “That’s like Michael Jordan going after a 12-year old in a game of 1-on-1.”

I laughed when I first read that. Typical Jason.

But, having thought about it, I think there’s an interesting game to be played.

Does Jason think he’s the Michael Jordan of blog businesses? If he really believes that mallarky, I’ve got $10K that says he’s wrong.

For those of you who don’t know Jason, he’s the hyperarticulate entrepreneur who made his fame by poaching pioneer tech blogger Pete Rojas from Nick Denton, duct-taping Rojas to Brian Alvey‘s smart software and Google Adsense, calling it “WeblogsInc” (WIN!), then talking AOL into buying “the future of blogging” for what some say was $25 million and others say was $6 million with an earn-out.

Jason, of course, views this feat as proof he’s the Michael Jordan of building blog businesses. If you measure business as a) talking very fast and sometimes brilliantly, b) embracing Pete Rojas, and c) putting the most money in his own hands, Jason is Michael Jordan.

Fact is, on all the key metrics, Blogads.com creamed Jason.

Foresight: Blogads.com was registered in March of ’02, WeblogsInc was registered in June of ’03.

ROI: While Blogads.com bootstrapped with less than $20,000 in cash in the bank, Weblogsinc reportedly relied on millions invested by Jason’s buddy Mark Cuban of Broadband.com fame.

Customers: While WIN had zero happy customers — at least judging from an archive of WIN’s pre-AOL website — we’ve got miles of uniquely thrilled customers.

Innovation: While WIN was peddling web 1.0 ad units, Blogads has pioneered genres of ad units designed for social media — long before the concept of “social media” existed. More on the way, too. (WIN’s “comments on ads” came 18 months after our experiment; like us, WIN discovered that mutating ad creative (at least from smart advertisers) fast obsoletes each comment.)

Staffing: While WIN had a handful of full-time staff (5 or 10?), we’ve got 22 brilliant staff (and dog Taco!) in Europe and the US with new office space to grow…

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Why is Jason so cocky? Personality aside, Jason is inebriated on the big city/old media parochialism of NY/LA/SF. Nothing significant happens in places like Carrboro, North Carolina ’cause rednecks don’t read the internets, right? Jason and his cronies want to forget that the blogosphere transforms the outside into the new inside.

Now Jason has departed AOL and is entrepreneur in residence at Sequoia Capital. Should I be wary of Jason? Absolutely. He’s had five years to study our business and has a excellent track record of “borrowing” good ideas/people, whether from Gawker or Digg. He’s sitting in the offices of a VC who backed Yahoo, Apple and Youtube. Even a midget can jam the ball if he has a ten-foot ladder. So I won’t make predictions about the future.

But let’s talk about the key performance metric. Does Jason want to put his big money where his bigger mouth is? I’ll wager $10,000 that in 2006 Blogads earned more for bloggers than did WIN. After all, blogger earnings is the true measure of a blog business, right?

What kind of odds would Michael Jordan give a twelve-year-old in a game of 1-on-1? A million to 1? Maybe 10,000 to 1… with the MJ blindfolded and his shoes tied together?

Well, this twelve-year-old would be happy with 10 to 1 odds, Jason’s $100K to my $10K. If those odds make Jason queazy, I’d be happy to discuss something gentler.

Jason apparently got $25 million from AOL and is the Michael Jordan of blog businesses, so he’s got the cash to toss on the table. Does he have the guts?

Details: the arbiter will be a mutually agreed independent accounting firm (in Vegas?) with an NDA to all parties, comparing both companies’ 2006 totals for net blogger earnings.

Let’s play 1-on-1 Jason.