NEW YORK — Even the usually glib Barry Diller struggles to describe InterActiveCorp, the crazy quilt of electronic commerce that he has stitched together during the past decade.

The multimedia magnate sputters through a tortured analogy likening IAC to a "concept beast of conglomeration" before finally acknowledging his New York-based company consists of so many disparate parts that it seems more like a jumbled puzzle.

"When you are beginning something, the early steps — at least in my case — can be quite messy," Diller said.

Diller, IAC's chief executive and controlling shareholder, hopes his strategy becomes clearer after he wraps ups a $1.9 billion takeover of online search engine maker Ask Jeeves Inc. and then spins off one of his biggest attractions, Expedia.com, into a separate company.

Both transactions are expected to be completed later this month.

It represents another roll of the dice for Diller, whose convoluted twists and turns at IAC have caused many investors to wonder whether the billionaire has lost his golden touch after decades of success as a top television and movie executive for ABC, Paramount Pictures and Fox.

The doubts have caused IAC's stock to plunge by more than 40 percent during the past two years, wiping out about $5 billion in shareholder wealth. Since 2002, Diller has spent more than $10 billion building IAC into an Internet powerhouse, but its stock has shriveled from a high of $42.74 to a close of $24.27 on Friday.

"There's a lot riding on this acquisition," Piper Jaffray analyst Safa Rashtchy said. "All eyes are on Barry now, waiting to see what he can do with Ask Jeeves."

Although Ask Jeeves has been perennially overshadowed by better-known search engines, Diller is convinced the Oakland, Calif.-based company is the missing ingredient in his Internet stew.

If it pans out the way Diller envisions, Ask.com and several affiliated search engines, including Excite.com and iWon.com, will become the mortar binding all of his other Web sites — a so-far dysfunctional family delving into travel, lending, ticketing and matchmaking.

For example, a lonely heart looking for a date on Match.com could use the Ask.com to plan a night on the town — a journey that might ultimately lead to Hotels.com, one of the sites to be included in the Expedia spinoff.

Diller ultimately wants to transform Ask.com from a second-tier search engine to a serious threat to Google. He is mulling the possibility of breaking away from Google's highly profitable online advertising network after Ask Jeeves' current contract expires in 2007 to launch a rival marketing system, building upon his years of media experience.

The commissions Ask Jeeves collected from Google helped lift the company to a $52.2 million profit on revenue of $261 million last year.

By 2008, advertisers will spend about $9 billion annually to have their Web links posted alongside search results and other relevant content, up from $5.4 billion this year, estimates Forrester Research.

Rashtchy doubts Diller will be able to create another advertising network, but he believes the executive's media savvy and IAC's deep pockets will give Ask Jeeves a legitimate shot at chipping away at the market share of Google and Yahoo Inc., which runs the Internet's second-most-popular search engine.