Jason Calacanis: “I Plan On Buying $250,000 Worth Of AOL Stock”

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As the founder of Weblogs Inc., Jason Calacanis is, in many ways, the cofounder of the new AOL, which will be built around the company’s network of 80 blogs and content sites.

So when we asked the Mahalo CEO for his take on AOL’s future, we thought he’d toss a helpful quote our way. We got much more.

Dig in:

1. I’m obviously flattered that AOL’s IPO strategy is the one we pioneered at Weblogs, Inc. It’s ironic that people made fun of Jim Bankoff, Jon Miller and Ted Leonsis for doing the deal at the time, saying that AOL way overpaid for 18 month old company. Of course, now folks are saying we sold too cheap! Perhaps that’s the definition of a good deal: the sellers getting overpaid in the short term and the buyers underpaying in the long term.

2. I think that AOL has difficult challenges, as Business Insider has pointed out, with the subscription revenue. However, expectations of AOL are very low [and this] means they can over perform. This will be very profitable for the management teams stock options which should be priced very, very low. I’m guessing Tim Armstrong will make a Terry Semel-like return on AOL in five years.

3. Right now I plan on buying $250,000 worth of AOL stock after it goes public. I believe Tim Armstrong is a great executive who understands the new publishing model, and he is a consumate sales person from what I understand.

4. The biggest challenge for AOL is getting direct traffic, which is to say “traffic that you earn,” as opposed to traffic from their homepage. They are well aware of this. The way you get direct traffic is to have a visionary–and at times unreasonable–editorial leader like Nick Denton, Rupert Murdoch, Jann Wenner or Si Newhouse. Right now AOL has great editorial talent, but clearly they don’t have that person.

If AOL asked me to be on their board, my advice and mission would be to get Tim a visionary editorial/product person to collaborate with. The best companies, in my opinion, pair product and business visionaries: 1. Larry/Sergey + Eric, 2. Steve Ballmer + Bill Gates/Ray Ozzie and 3. Steve Jobs + Steve Jobs.