All Things Digital

BoomTown was all busy trying to think of execs to replace Yahoo CEO Jerry Yang, as pressure mounts on him to right the troubled Internet company.

But now, Yang’s position feels safer than ever and it’s his nemesis–Microsoft– that needs a new leader for its long-stumbling online services business.

Microsoft (MSFT) was already cracking, according to sources, and had a wish list of internal and external candidates that CEO Steve Ballmer is now considering.

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How’s this for a lead-balloon argument to get shareholders to reject activist investor Carl Icahn in his quest to unseat the Yahoo board and senior management that was uttered by its CEO Jerry Yang in today’s Wall Street Journal:

“To trust Mr. Icahn and his board is really a bad choice.”

Oh. Phew. Thanks for warning everyone, Jerry, so that bullet could be dodged!

But, besides the quote begging the question of what makes Yang a good choice, which he must articulate rather than just diss his rivals, it lacks the necessary oomph that Yang needs to make his case more aggressively and definitively.

That’s especially true, if he is to stop Icahn from gaining the momentum he needs to win his proxy fight against Yahoo (YHOO).

As Microsoft (MSFT) should have done in its attempt at the Yahoo takeover, one has to remember to actually hit the target when you shoot.

So here’s a much better one to needle Icahn with, using an famous old ad tag line:

Where’s the beef?

Specifically, who’s going to mind the store if Icahn actually manages to win and makes good on his promise to fire Yang?

Because if there is one thing that is hurting Icahn’s chances, it is the worry among major Yahoo investors that he simply cannot run Yahoo, even for a short time.

So, of course, he is out beating the bushes for a suitable CEO.

“Carl has to have a management team that he announces soon, so people can see that there will stability if he wins,” said one investor source, in a typical sentiment I encountered. “Taking out a whole board and the top managers of a major public company is drastic.”

Indeed, which is why Icahn has been working feverishly, sources said, to attract someone to run Yahoo in the interim, in the event he wins his proxy battle and he seeks to strike a deal of some sort with Microsoft to buy part or all of Yahoo.

As BoomTown previously reported, Icahn is still attempting to entice former AOL (TWX) head Jon Miller, along former Fox (NWS) Interactive Media exec Ross Levinsohn, to take the job on a temporary basis, sources said.

Neither Miller nor Levinsohn, who now co-run an online-focused investment fund called Velocity Interactive, has agreed to do this yet, a risky move that might tarnish anyone who takes it on.

In addition, most suitable candidates for such a job would likely prefer to do it in a friendly fashion, working with Yang to transition him out of the CEO role.

Yang has acknowledged to several people that some investors, angry about the botched Microsoft takeover deal and the declining stock price, are seeking his ouster, as well as that of Yahoo President Sue Decker.

But Yang is definitely not resigning, as some stock-goosing hedge fund vultures were putting out earlier today.

In any case, Icahn, who has lost money in this activist bid, is working overtime to make that happen by convincing shareholders that he is the better choice to strike a more lucrative deal for Yahoo.

In fact, he underscored it earlier this week when both he and Microsoft released almost exact statements that they were talking and could work with each other. Both also noted that Microsoft did not feel it could work with current Yahoo leadership.

Could Ross Levinsohn and Jon Miller reinvent Yahoo (YHOO)? What about OpenTable’s Jeff Jordan? Or various and sundry Google (GOOG) or Microsoft (MSFT) execs?

It could happen.

That specific scenario of putting someone like the two former Internet execs (they ran Fox Interactive Media and AOL, respectively) in charge of the troubled Web giant is one of the many being bandied about, as Yahoo shares tumble and the company heads toward a potentially ugly annual meeting everyone involved desperately wants to avoid.

In fact, Yahoo’s board and major investors are talking today about various options for the company, including Yahoo’s receptivity to a sweetened deal with Microsoft and also other ways to pull the asset-rich company out of its stock doldrums.

It is not likely to be a very chummy meeting, of course, considering Yahoo’s stock (see this depressing chart to the right) has been drifting inexorably downward with nary a lifesaver in sight.

Yahoo shares sunk ever closer to $20 (it closed today at $20.66, down more than three percent)–a worrisome crossing of the digital Rubicon for the company, given that it makes Yahoo more vulnerable to all sorts of Wall Street machinations.

Besides allowing other large companies like News Corp. (NWS) and Comcast (CMCSA) to consider bids for Yahoo–both have been watching the situation very carefully, sources said–it also opens Yahoo up to attacks from more rapacious private equity investors.

And there is a lot of machinating already, of course, as I have found poking around, with more to come.

Like what?

Like Yahoo back in discussions with AOL once again. Sources close to the situation said that the idea of hooking the pair up have been revived, as Yahoo looks to strengthen itself and Time Warner (TWX) searches for any way to spin off a division it has never been able to juice up.

Of course, Microsoft has also been sniffing around the property too–and almost bought AOL several years ago–and would be unlikely to sit still and let Yahoo grab AOL’s most attractive asset, its Platform A online advertising unit.

(Memo to Time Warner CEO Jeff Bewkes: You’re known as a smooth deal-maker, so paste on that million-dollar smile and get dealing!)

And, more interestingly, are the moves to try to find another CEO and top leadership to come in and run the company instead of Yahoo CEO Jerry Yang and President Sue Decker.

(I had previously posted on possible picks for that job here.)

That could come in either a friendly or non-friendly approach, according to several people close to the situation.

Under the friendly scenario, Yang would voluntarily step aside–and even be upped to non-executive chairman status–while a new CEO and team would be put in place.

A less dulcet approach, which would require an aggressive move by Yahoo’s board–who make head-in-the-sand ostriches seem active–against Yang directly is less likely.

Still, many investors, increasing numbers of employees and even some Yahoo board members have lost confidence in Yang and Decker, who have been trying to set a new course for the company.

But does a new course require new leaders?

Levinsohn and Miller (pictured here, left to right), who now run an online-focused investment fund called Velocity Interactive, are two high-profile former Web execs mentioned most frequently by major Yahoo investors as candidates for that idea.

Sources said could either come in as board members or actually run the company for a time period, while searching for a new CEO, like OpenTable’s Jeff Jordan, Google’s Tim Armstrong or even Microsoft’s Kevin Johnson.

Such as plan could include additional investments by new investors and critical buy-in by current investors–including billionaire activist Carl Icahn, who is waging a proxy fight against Yahoo that is set to come to a head at the Aug. 1 annual meeting.

Most important would likely be cooperation from Microsoft too, which could offer to also buy some of Yahoo and also sweeten its search-ad deal.

It would also require a new plan for Yahoo, which will likely include job cuts and a more drastic refocusing of its business that perhaps only outsiders can do.

As its founder, not surprisingly, Yang has been slow to make the kinds of deep changes many think Yahoo requires to reinvent itself, and Decker has been part of the team that has gotten the company mired in its current state.

While this all sounds incredibly complex, all scenarios point in one inevitable direction: Massive change is coming to Yahoo in the next 30 days, one way or another.

Who in the Internet sector hasn’t enjoyed the always amusing stylings of Mr. Ross Levinsohn, the high-profile former head of Fox Interactive Media a.k.a. “The Guy Who Bought MySpace for News Corp.”?

Today, he added another song to his silky smooth repertoire as the “Internet guy who dissed Yahoo.”

In a nice scoop, TechCrunch reported that Levinsohn was going to be a nominee to the board that Microsoft (MSFT) has been forming as part its potential proxy fight to take over Yahoo (YHOO).

That’s true, several sources have told me. Levinsohn, who was recruited by Microsoft’s Yusuf Mehdi, has even filled out paperwork as part of the process.

And once the i’s are dotted and the t’s crossed, that makes him the highest profile Internet figure on the board, which is made up of–let’s just say it, shall we?–pretty unimpressive former execs, none of whom has had any substantial Internet experience.

While many well-known Web figures were approached by Microsoft, few in Silicon Valley have been willing to be part of an effort to snuff out an independent Yahoo, one of its most important and iconic brands.

Not so the entrepreneurially inclined Levinsohn, apparently, who has a maverick nature.

He left FIM in 2006, for example, after deciding he wanted to be more than an overpaid employee of Rupert Murdoch and Peter Chernin.

Now, the Los Angeles-based Levinsohn runs an investment fund called Velocity Interactive Group with former AOL (TWX) head Jon Miller. Armed with $1.5 billion, the investment focus of the new enterprise will be on digital media and communications.

Given possible News Corp. (NWS) involvement as a possible partner in the Microsoft deal (more on that later), including a desire by Murdoch to spin MySpace into Yahoo, it’ll be interesting that Levinsohn might now have some power over his former bosses.

Or not. Most expect the board to be a rubber stamp for Microsoft, although several sources say those asked have been told that they can vote in the way they think is best for Yahoo.

Kind of like superdelegates! Except geekier!

Here is a video interview I did with Levinsohn in December of 2007, where he talks about the future of digital media on the Web, as the tech and entertainment industries and its many players seek to figure out how to make the painful digital shift and find new monetization plans that will replace crumbling old-media businesses.

At the end, months before Microsoft’s unsolicited bid for Yahoo was launched, after I asked him what will be coming, the psychic Levinsohn eerily predicted: “Something happening with Yahoo, I think, this year.”

Something indeed.

Here is the video:

On our recent trip to sunny Southern California, we had a lively lunch in Brentwood with the ever-sassy Ross Levinsohn.

In the dullish panoply of Internet moguls, Levinsohn stands out as one of the more colorful characters, no small thing since he comes from a big company, News Corp. (owner of this site), where he played a big part in its on-the-cheap MySpace acquisition in 2005.

But big company no longer for Levinsohn!

Just before the holidays and four months after launching their digital media roll-up firm Velocity Investment Group with private equity firm General Atlantic, the former Fox Interactive Media president and his partner, former AOL head Jon Miller, announced a new and improved deal.

This time, it was a merger with ComVentures with its $1.5 billion in assets (with more fund raising to come) and a new name, Velocity Interactive Group. The investment focus of the new enterprise will be on digital media and communications.

Here’s Levinsohn talking about all that and more (excuse the noisy ladies about three minutes in):

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So, I am back in Los Angeles today, part of my ongoing quest to make sense of the wrenching changes facing the entertainment industry in the face of the continuing pummeling by the digital tidal wave.

I just had a bracing lunch with Ross Levinsohn, former Fox Interactive Media head and newly minted investor, where we talked about his recent efforts to invest in digital media and communications with his partner, former AOL head Jon Miller.

More on that chat next week, including a video with the voluble Levinsohn about his new venture, in which he is seeking to bridge the gap between the Silicon Valley and Hollywood (good luck with figuring out that old Gordian Knot).

But–all mythical legends aside–someone has to, and anyone interested in the tech business in the years ahead has to understand the stakes and challenges ahead for Hollywood.

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I will be traveling south to Los Angeles Sunday afternoon to do a few days reporting there.

That will include visits to the offices of JibJab, Userplane, Disney’s Internet Group, as well as some catching up with newly minted investor Ross Levinsohn and Joost CEO Mike Volpi.

We’ll be headed that way again a week later to go to Rafat Ali’s “iPhone & Beyond” one-day conference, and to see the new studios of TMZ, the execs at Move.com, Veoh and perhaps visit MySpace, Yahoo in Santa Monica, Helio and also meet the new head of Hulu.

Also on the agenda, DEMOfall and a lunch with blogger Paul Kedrosky in San Diego.

As you can see, a wide range of companies and people, which is why if you’re going to be a tech reporter going forward, you must school yourself quickly on what is happening in the digital arena in Southern California.

I have an even longer list of people and companies I want to meet there, so I expect to get there more often over the next year, rather than just sticking to the 101/280 corridor here in Northern California.

In fact, I have been wading deeply especially into the entertainment industry for a long time now, because the intersection of that industry and tech is one of the more important stories going forward. It’s a canard that Silicon Valley and Hollywood are at odds. While they will be fighting, of course, their fates are now inextricably combined and even aligned.

Case in point: A post I did this past week on the appalling instance of an ingenue singer being “discovered” on YouTube, when it turns out she was being secretly groomed by Hollywood Records to seem like an amateur phenom.

An amazing story, which is all about how marketing, entertainment, content and distribution of information are shifting quickly and with great chaos.

So, I will just say, as Randy Newman sings below (a video someone ripped onto YouTube, of course), I love L.A. Considering the stakes, it would be foolish not to.

I went to a dinner last night hosted by John Battelle and Tim O’Reilly of the Web 2.0 Summit, and it was one of the more schmoozy events I have been to in a while.

The event–this year at Foreign Cinema in the Mission District of San Francisco–is held to elicit feedback from the Internet’s movers and shakers about the new directions the conference, set to take place in San Francisco in mid-October, should head in.

Except Battelle and O’Reilly already came up with a theme: “The Web’s Edge.”

I am not entirely sure what that means. Is it that it is at an edge? Or that we need to look at the edge? Or just that things just feel all pointy lately? Big thoughts all!

In any case, the party was a lot of fun and filled with digital personalities, like Mitch Kapor and Ann Winblad, as well as a few folks I interviewed like ex-AOLer Jon Miller, ex-Fox exec Ross Levinsohn, VC David Sze, Tina Sharkey of BabyCenter and Webby Awards founder Tiffany Shlain.

Here’s the video: