Investors have applauded Diller's decision to break up IAC, which owns disparate businesses like HSN, Lending Tree, Ask.com, Citysearch and Match.com. That said, IAC's recent stock gains have been nearly erased by the overall retreat in the stock market this week. It remains unclear how Diller and Malone will resolve their interests in the company.

"It's ultimately going to depend on how IAC structures the spin, but it's an opportunity for the company to put their heads together and come up with a solution," says Shelton. "Liberty has this big IAC equity stake and they'd like to tax efficiently monetize that. The way to do that would be some sort of asset swap with IAC and something like that probably happens before the assets get spun off."

For his part, Roge doesn't see upside in Liberty's interactive holdings as a result of the restructuring. He says the home shopping business is a bad investment in the long run because the Internet will provide better ways for consumers to shop from home.

"It's profitable now, and if Malone thinks it'll be profitable in the future and there's global expansion opportunities, then so be it," says Roge. "I just tend to think it will be one of the mistakes in his legacy."