IAC's Barry Diller: Not Dead Yet

Duff McDonald has a piece on Barry Diller in the June issue of Portfolio. I asked him what he thought of the mogul, after following him through a long and painful trial with John Malone. It seems there might yet be life in the old dog yet:

FS: Barry Diller might have won the court battle with John Malone, but he's also conceded defeat on a big-picture level: He's breaking up his company, IAC, into five pieces, of which he will control only one. Is this the end of Barry Diller, new-media mogul?

DM: Not yet. If he gets his way, he's actually shaking off all the non-new-media assets, such as HSN, Interval, and Ticketmaster, as well as the albatross LendingTree. What's left? All new media. So it's not the end. But it's pretty much his last shot at new media glory. If this one doesn't take, then he will go down with a new media track record like many others: smart enough to catch the first wave and at a serious loss for good ideas since. Even the guys from Pets.com could say something like that.

FS: Diller's already decided to reinvent Ask.com as a niche site targeted at middle-aged women, and his new-media future seems wan. What has happened to the aggressive and charismatic dealmaker of old? Why is he giving up valuable properties which he might otherwise be able to sell as part of an attempt to catch the next wave? After reading your article, it certainly seems as though Diller is on his back foot -- and that's without a possible appeal from John Malone (L) of the legal decision which presently sits in Diller's favor. Also, Diller's 66 years old, and has made more money than he'll ever be able to spend. Does he still have the fire or the hunger to go on the offensive and fight to build something great again?

DM: They talked about people calling Ask a niche site, and pointed to the $$ it brings in. I'm not sure conceding defeat to Google (GOOG) is an indication of failure. It is an indication that you are everyone who isn't Google. And he's not "giving up" the other properties. He's loading them with debt and spinning them off, keeping the cash with so-called "new IAC." So he's milking them one last time, capitalizing them like their peers, and stocking new IAC's war chest with coin. And then he's going to try and be a content provider of Web 2.0 and beyond. You're right, there's no clear path here, and no reason to think he'll succeed, save for the fact that he has done so before. Would I buy the stock? Probably not. Would I short it? Definitely not. So while I think there are better ways to take a bet on the web, I certainly wouldn't bet against him. Perhaps that's the point of the piece. Despite all odds, he's still here. And doesn't seem to be slowing down. (Seriously. He doesn't.)