All Things Digital

As BoomTown reported on Tuesday, The Wall Street Journal is now reporting that Microsoft (MSFT) and Yahoo (YHOO) have been chatting away informally, after a week of faux-wrestling.

It’s been like WrestleMania, except without the excitement and anticipation. Also, no cool names or outfits.

As I posted on Tuesday:

While it is true, as we and everyone else have posted, that Yahoo and Microsoft still have not entered into or even scheduled any formal talks, even after the software giant’s threat to launch a hostile bid came and went over the weekend without action, it is also not true that there are no talks going on.

According to sources close to both companies, there are informal discussions now taking place between Yahoo and Microsoft–via bankers, board members, shareholders and others close to both companies–to try to prevent a hostile takeover scenario or the sudden withdrawal of Microsoft’s offer.

Both options are unattractive for a number of reasons to pretty much everyone and, in BoomTown’s opinion, an excellent example of how juvenile this takeover battle has become (or “amateur hour,” as one source close to both companies described it to me).

A hostile bid by Microsoft, for example, is profoundly distracting to both parties and could result in an exodus of Yahoo staff, along with being risky in terms of certain success for Microsoft.”

And from the Journal this afternoon:

The two sides and their advisers have had informal discussions over the past week, but have been stymied by a divide on the price Microsoft should pay to acquire Yahoo, say the people. Microsoft has been weighing whether to drop its bid or go hostile, and has promised to announce its decision this week. As of Thursday night, Microsoft was leaning toward going hostile, but the situation remained fluid, according to people familiar with the matter.

Now, people close to the two sides are attempting to avert that prospect with discussions they hope could lead to a negotiated outcome, say the people. Microsoft has wanted to avoid a hostile takeover battle, which could drag out and result in distraction and the loss of key Yahoo employees.”

In the late 1990s, during the height of the bubble of Web 1.0, there was a poolside charity auction at an Industry Standard conference for a variety of items donated by Web luminaries.

A tie from John Doerr, the right to push eBay CEO Meg Whitman in the pool and also the little black dress that then-CEO Katrina Garnett of CrossWorlds Software had worn and made famous in a Richard Avedon-shot ad for the company.

I am blanking on the person who bought the dress, but what was most interesting about that item was that the same person kept upping his own price, and went several rounds bidding against himself before winning the prize for a lot of money.

It was amusing at the time, a symbol of a very frothy time indeed.

Today is not that time, so I was a bit perplexed at why Microsoft (MSFT) would top its own bid and raise its $31-per-share offer for Yahoo (YHOO) to $34 a share, as suggested by Citigroup (C) analyst Mark Mahaney yesterday.

There seem to be no other rivals and not much has changed since the software giant made its unsolicited offer at the start of February, except for time passing.

Of course, the only reason to do so then is to get the deal done sooner than later and perhaps the number was a public message to Microsoft CEO Steve Ballmer of that fact (as I said before, I am sure there are plenty of private messages too).

And while I am in the camp that Yahoo, well run, is probably worth a whole lot more (see this post I did at the start of this slog) than even $34–although perhaps not the $40 that Yahoo claimed last week–it’s still a matter of actually getting Microsoft to pay it by bidding against itself.

As I saw back in the roaring ’90s, it could happen. The question is: What will it take to get Microsoft to do it?

My guess if it happens: Sheer boredom and the cost of wasted time during which rival Google (GOOG) keeps chugging along and a distracted Microsoft and Yahoo do not.

Please see this disclosure related to me and Google.

Over the last year, as he has sought to revive the flagging fortunes of Yahoo, CEO and Co-Founder Jerry Yang has ferreted himself away from the spotlight and has seldom made himself available to talk to investors or reporters about what he has been up to.

I dubbed it the “cave” strategy, mostly because that’s what many around Yahoo called it. Since Yang really didn’t have anything good to say about the troubled Internet giant, he didn’t say anything at all.

I always thought that a big mistake, since it was very insular and defensive. Like my politicians, I like my Internet execs able and willing to take on all critics (and for all the grief I have been giving Facebook, in stark contrast to Yahoo, its execs are very willing to go a round with anyone who questions their moves).

So you might have thought that the surprising unsolicited bid to grab Yahoo by Microsoft might have brought out the fighting spirit in Yang.

That’s especially true, since it has been widely reported (and entirely true) that he had rebuffed such advances many times and was actually not shocked (despite what has been reported, Yang had to know it was coming given the weak, stock-depressing quarter he turned in on Tuesday) by the $31 per share offer he received on Thursday.

But, no.

“So they are now deeper in their cave than ever,” reports one frustrated person close to the top execs at Yahoo yesterday, echoing a widespread sentiment at Yahoo’s Sunnyvale, Calif., HQ.

Deeper? Is that even possible? If so, Yang must now be living in the Mariana Trench of the Web world.

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