All Things Digital

Billionaire activist investor Carl Icahn has asked for it, although he has gone all kittenish now, after realizing his scheme to get Microsoft (MSFT) to buy Yahoo (YHOO) was over, once Yahoo signed on with Google (GOOG) to outsource some of its search-ad business.

And then the New York Times’s Joe Nocera called for it in an eviscerating column this past weekend that articulated what an increasing number of people in Silicon Valley and Wall Street and, more importantly, within Yahoo have been thinking of late.

And that it is: Whether Yahoo CEO Jerry Yang (pictured here at D6) should step down in favor of another top executive to lead the troubled Internet company into the next era.

It’s the obvious question, of course, to ask whether the co-founder of Yahoo has what it takes to manage the company through what will doubtlessly be a very difficult year.

(Speaking of that, see this disturbing hiring freeze post by Peter Kafka of Silicon Alley Insider, which might spell trouble ahead at Yahoo.)

BoomTown asked Yang specifically why he was the right leader for Yahoo going forward at our sixth D: All Things Digital conference recently and–guess what?–he did not really have an answer to the question.

Let me for him, then: The main reason he is the right leader is due to his history, his obvious love for Yahoo and its employees and that his heart, as Yang said in his one and only passionate moment onstage, does bleed Yahoo purple.

Unfortunately, as important and touching as those things are, it’s probably not enough for the rough road ahead for Yahoo.

As Yahoo continues to be in limbo, pressure is sure to mount heavily on Yang, and it is not a stretch to imagine he will not remain in the top job at the troubled company for the long term.

So who would be good to replace him?

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It’s clear that some Yahoos and its CEO and Co-Founder Jerry Yang have got to be a little more than miffed that billionaire entrepreneur Mark Cuban is on billionaire investor Carl Icahn’s board, as he begins a proxy fight for control of the troubled Internet company.

As BoomTown noted in a post yesterday, there is no love lost at Yahoo (YHOO) for Cuban (pictured here).

He sold the Web 1.0 star, Broadcast.com, for $5.7 billion in cash to Yahoo at the peak of the bubble in 1999, skedaddled quickly and then made bank by hedging his Yahoo shares and enjoying the proceeds extravagantly.

As one longtime Yahoo, who has left the company recently, emailed me in a typical sentiment: “You don’t even know how much they hate Cuban over there.”

Oh, I do.

But, while I get the emotional part, it is actually quite unfair realistically, given it was Yahoo that did precious little with Broadcast.com’s assets after paying so much for the company.

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Of the amazingly Internet-experience-free board that billionaire investor Carl Icahn has proposed to replace Yahoo’s current directors in this proxy fight, there is one name who does have a lot of Web-related experience, especially with regards to Yahoo (YHOO).

Specifically, in how to make bank from Yahoo’s desperation.

That would be entrepreneur and all-around bon vivant Mark Cuban (he is pictured here at our first D: All Things Digital conference in 2003), who sold Broadcast.com to Yahoo in the heady days of 1999 for $5.7 billion in Yahoo stock.

It was a huge deal at the time, with Yahoo engaged in an arms war with other Internet companies like Excite (remember them?), AOL (TWX) and others.

In an acquisitions frenzy, it grabbed Broadcast.com, which was started in 1992 as AudioNet, with Cuban and others in charge.

Broadcast.com was one of the nascent efforts to broadcast online, focusing on radio-like content on the Web, largely using sports and other live events.

It had one of those typical Web 1.0 faux-blockbuster IPOs in 1998 and then, as the stock began to decline, sold quickly to Yahoo a year later.

Right before, as it turned out, the whole bubble burst.

But Cuban and his cohorts made their scratch and were soon gone from Yahoo.

Cuban, sensing the end was nigh, also dumped his Yahoo shares before the decline. And, armed with a fortune, he began his fun foray into a range of businesses, from sports teams to movie theaters to his HDNet, a high-definition cable network.

And, of course, the private jets and entertaining courtside antics and working at the Dairy Queen!

And, also of course, most of Broadcast.com’s assets are useless to Yahoo today.

Now, Cuban is back knocking at Yahoo’s door as an invader, the only major Internet figure apparently willing to turn on the iconic Yahoo CEO and Co-Founder Jerry Yang.

Calling Benedict Arnold!

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Oh how very delicious comes the news that once obstreperous Internet entrepreneur and now obstreperous Mavericks owner Mark Cuban might appear as a contestant on the guilty-pleasure television show “Dancing With the Stars.”

According to Sports Illustrated, Cuban might join–I have truly died and gone to heaven–singer Wayne Newton and “Beverly Hills, 90210″ star Jennie Garth in the reality show phenomenon, which is actually a pretty tough challenge once you get beyond all that glittery spandex tight pants flaunting and focus on the difficulty of learning how to dance that well in front of huge audiences.

Of course, the Internet chattering class has been more riveted by Cuban’s recent “fight” with VC Fred Wilson and really the whole of the digerati, after he basically said the Internet was “dead and boring” in a post on his Blog Maverick site. (Cuban is pictured above almost perfectly.)

He actually only used those terms to get people all pissed off–a typical Cuban tactic–in this post, but was actually making a great point about the Net becoming a utility and how that is a good thing.

I would agree. Just because I did not ooh and ahh over the fact that my blow dryer was powered by the electrical grid this morning does not make it any less amazing.

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