Ted Leonsis regrets one deal he was involved in and shared his vulnerabilities with Alex Rodriguez and Jason Kelly on the pair’s new Bloomberg show, The Deal. In the latest episode of the web series, Leonsis says he was never involved in a signature deal but was certainly involved in what he considers the worst—the AOL/Time Warner merger.
“I was a participant in the world’s worst big deal,” Leonsis said. “AOL bought Time Warner and it was the largest acquisition in history. AOL was the first Internet company to go public, the dot-com bomb happened, and basically it destroyed value and Internet 1.0.” Rodriguez then asks Leonsis what he learned about the deal and Leonsis answers quickly.
“It’s better to be about Main Street than Wall Street. I’m at the point in my life where I just focus on — is the product great? Is the service great? Do they love what we do? Everything will flow from that.”
After some discussion, Leonsis admits selling his startup to AOL was a great move in hindsight because it gave him so much AOL stock. “Well, I sold my little start-up to American Online and I got ten percent of AOL, $40 million of stock.”
Leonsis is now the founder of Monumental Sports and Entertainment, a sports and venue management company that owns the Washington Capitals, Wizards, and Mystics, among other teams and properties. It also owns the Monumental Sports Network, a regional sports network that serves the Washington, D.C. metro area and broadcasts the teams’ games.
Barrett Media produces daily content on the music, news, and sports media industries. To stay updated, sign up for our newsletters and get the latest information delivered straight to your inbox.
