Ted Leonsis on AOL, Microsoft, the NHL

I interviewed Ted Leonsis, a top AOL executive during the company's heyday and owner of the Washington Capitals hockey team, in front of a lunch crowd of 120 or so people on Wednesday. The conversation ranged widely, and he had some interesting things to say.

On being a pro sports owner: It's very different from business, Leonsis said -- especially because of two factors. 1. Few businesses have zero-sum winners. In sports, you either win the championship, or you don't. 2. There are a lot of weird vagaries introduced into the sports business that don't exist in regular business. He gave the example of health. "In all my years in business, no one has ever come into

my office and said, 'Are you sitting down? Our HTML coder has tendinitis,'" Leonsis said, getting a big laugh. In sports, of course, an injury to a star player is a big deal.

On using the Web to win a bigger audience for the NHL: He quoted Gretzky's saying that he skates to where the puck is going, not where it is. "The puck today is television," Leonsis said. The Web is where the puck is going. In a roundabout way, Leonsis basically said the NHL would be better off abandoning its fairly low-budget local TV contracts, packaging all its games on the Web, and spreading NHL games virally through things like widgets. The league, he said, has been open to those kinds of ideas -- but Leonsis gave no indication that the NHL was likely to do anything like this soon.

On Web advertising just passing cable TV advertising in revenue: "The Web isn't new media anymore. It's THE media," Leonsis said.

On why AOL, once as dominant on the Web as Google is today, lost its position: In the late-1990s, as the Web slowly started to shift to free services, Leonsis said he argued to break AIM out of AOL's paid subscriber business and make it free to anyone. AOL did that and AIM became a huge hit. Then Leonsis argued AOL should do the same with email, and the company balked. "I argued, but I wasn't persuasive enough," he said, shouldering that blame. If AOL had gone free with email then, Hotmail and Yahoo mail wouldn't have gotten such traction, and AOL would've held onto customers and page views. He seemed to think that was the turning point for AOL. If the company had acted differently toward free services at that point, it might still be dominant today, he suggested. He added, referring to the AOL-Time Warner deal and getting a laugh: "And of course the merger wasn't helpful."

On Microsoft pursuing Yahoo: "Name one big merger that is a best practice to emulate," Leonsis said. No hands went up. As Leonsis said, there basically are no big mergers that have truly succeeded, and he clearly thought Microsoft could be making a big mistake -- this coming from a guy who saw the AOL-Time Warner train wreck up close.

All in all, Leonsis was charming and funny. He's involved in so many projects it must make his head spin, but he talked most about two (other than the Capitals): ClearSpring, a Web widget company he's invested in, and his venture into movie-making, particularly Nanking and Kicking It. You can find out more on Ted's blog, Ted's Take.

 (Credit: Manuel Balce Ceneta/AP Photo)