At Ask.com, Barry Diller fires another entrepreneur

Bloody Diller. IAC's Ask.com has a new CEO, Jim Safka, who was swiftly installed in the place of Jim Lanzone. Lanzone was fired by Barry Diller, according to sources. And so yet another talented entrepreneurial type makes way for a Diller yes-man. The cover story is that Lanzone left to accept a position as entrepreneur-in-residence at Redpoint Ventures — a cozy, face-saving sort of holding tank for CEOs in between jobs.

Why did Lanzone get the boot? Diller's recent comments about Ask.com's failure to take market share away from Google are revealing. Of course, one wonders if that was Lanzone's fault. Lanzone is thought of in the search community as a features guy. But Ask.com never marketed its features effectively — most notably in a laughably cryptic marketing campaign, championed by Diller, about "the algorithm."

Could Lanzone have thrived under different management? That's the key question. Diller leaves behind him a long trail of entrepreneurs he's driven away: Jon Miller, who joined AOL after a stint at IAC; Steve Berkowitz, Jim Lanzone's predecessor at Ask.com; Rich Barton and Erik Blachford at Expedia; Jakob Lodwick at Vimeo; and now, most recently, Doug Lebda of LendingTree.

So Diller is a difficult boss. This would be acceptable if he were a good creative type, as he seems to fancy himself. But one would be hard-pressed to point to a good idea he's had since he pioneered the American TV miniseries decades ago. (Even that wasn't really his idea, since he imported it from Britain.)

He is, perhaps, a good judge of value. Buying properties on the cheap worked well with Expedia. But on the Internet, where power tends to concentrate with the top player — witness eBay in auctions and Google in search — Diller's instincts have betrayed him. Buying second-raters have left him with a third-rate company, which he is now disassembling.

Lanzone's beheading should be a cautionary tale to any entrepreneurs considering selling out to IAC. (One hopes Jay Adelson and Kevin Rose of Digg are reading this closely.) Are you willing to work for a tempestuous boss whose accomplishments are ones of financial engineering and Wall Street salesmanship, not creativity? Barry Diller's money is green enough. So, too, is his career as an innovator.