All Things Digital

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!

I don’t blame Cuban, actually, although Yang surely will be angry over his presence on the Icahn board.

There was always a level of rancor within Yahoo about Cuban, because he sold Broadcast.com at the top, traded out of Yahoo shares at the top and then simply sat back and watched it all as a billionaire gadfly.

BoomTown used to even tease Yang about how Cuban was richer than he was and got to have all the fun. It would always get a glare out of him.

So too could Cuban, as in this post from his smart Blog Maverick (of course, it is named that!) blog, right after Microsoft’s (MSFT) unsolicited bid for Yahoo,.

In it, Cuban urged Yang to sell to the Internet giant, largely due to the pressure of competing with Google (GOOG).

Cuban wrote:

Building a world class Yahoo to be the best company it possibly can be using the management skills that Jerry and company have is a far different challenge than optimizing the stock price. Particularly when Google is your stock comp…

Which is exactly why Jerry and David should sell to MSFT…

So the question isn’t whether Yahoo should sell. It should. The only question is what the structure of the deal should look like so that Jerry and David can achieve many of the goals they set out to accomplish on the net under the MSFT umbrella. Jerry definitely is about customers first. This is his chance to show it…

So Yahoo should say yes. It’s less about the money than about finally achieving the corporate goals set out more than a decade ago. One time Jerry told me that Yahoo stood for You Always Have Other Options. This time Yahoo doesn’t, but their customers options could improve exponentially if Yahoo says yes.”

Given the Yahoo acquisition of Broadcast.com gave the clever Cuban the billions he has used so entertainingly, it’s all kind of ironic, no?