May 19, 2008 7:58PM

It’s Like Dating, but More Annoying

By Cheryl Casone

We had Jill Schlessinger on the show today. She is too funny, and smart, and well, feisty. We were talking about Yahoo and Microsoft. When will this dance end? She compared it to dating on and off. Have you ever done that? You can’t make up your mind, and you can go back and forth.

She has a good point. What these two are doing is dancing, and while I certainly respect they are both trying to protect their single life (I am single, I understand) it is the market and shareholders who have to sit and watch. Reminds me of “The Bachelor” on ABC. The guy sits there, and goes back and forth: “so many women, I just don’t know, I love them all!”

Except Microsoft doesn’t want to settle down, they NEED to settle down. Their internet strategy is shot. I almost believe they will ditch MSN and just go with the Yahoo brand. Or, maybe MSN Yahoo actually rolls off the tongue? Carl Icahn is no fool, and he usually gets his way. Steve Ballmer might at the end of the day be no match for Jerry Yang. How long do you turn the guy/girl down before you just give in? You realize they are the right one.

While I certainly respect that Jerry Yang created and built Yahoo into the brand it is, sometimes the inventor isn’t the best manager. Does that makes sense? If I owned Yahoo, and I don’t, I would honestly ask myself if I felt enough trust in Jerry Yang right now to do the best thing for my shares. Not that Microsoft is this bastion of good will and charmed enterprise, they are still fighting antitrust issues in Europe, still!

Microsoft is most likely in your portfolio in some way. But is Yahoo? Think about potentially putting your retirement money in Jerry Yang’s hands? Ready to settle down yet?