Diller Offers Mea Cupla On Ask, Will Resign As Live Nation Chair

Barry Diller isn’t cut from the cloth of a typical Internet entrepreneur.

First of all, the chief executive of IAC/Interactive Corp. was born in 1942, during the early years of World War II. So at 68, he is something of a dinosaur walking among the 20- and 30-something Web entrepreneurs designing social networking sites and low-cost cloud hosting platforms.

Seems he also misjudged the search market. In the past several months, he has apologized for his stewardship of Ask.com. He expanded on his mea culpa Wednesday at the TechCrunch Disrupt conference, adding he doesn’t think Ask can gain share against industry behemoth Google.

I hate to say this so bluntly, but it was obvious from the start. Toppling a giant requires dramatic innovative change, not changes around the edges.

In any event, Diller said this morning that five years ago he believed innovation could improve Ask’s competitive postion and allow it to gain ground. “We did all of that,” he said, but the share gains didn’t come. Now, “I don’t think we’re going to gain share,” he said.

Seems that the fair amount of money IAC invested to revamp the site is largely wasted.

Diller acknowledged another set back. He confirmed his decision to resign as chairman of Live Nation Entertainment, the company formed by the merger of concert promoter Live Nation and ticket seller Ticketmaster. Diller said that at a board meeting Tuesday he suggested directors appoint a new chairman by the end of the year.

The Associated Press reports that Diller is leaving Live Nation after a power struggle with Liberty Media’s John Malone, also a board member.

Live Nation has faced a difficult business environment this year and its stock is down sharply.