All Things Digital

Well, there’s one niggling deal off the desk of Northwest Airlines Chairman Roy Bostock–Delta Air Lines (DAL) and Northwest (NWA) finally agreed to merge after three months of tiresome back-and-forth wrangling.

Sound familiar?

Bostock (pictured here)–apparently, the hardest working man in U.S. corporate board rooms–also happens to be the chairman of Yahoo (YHOO), which is in the midst of a takeover wrangle with Microsoft (MSFT).

So, if he managed to reach some sort of deal–either with AOL (TWX) or Microsoft–that would settle the fate of Yahoo this week, as some are speculating, I think some kind of medal would be in order.

And let’s not leave out the irony of the fact that the former top ad exec is also on the board of Morgan Stanley (MS), which is repping Microsoft!

Roy Bostock=Human pretzel!

Of course, there are still a lot of outstanding issues in the Delta-Northwest deal–including possible employee resistance and regulatory insistence. But getting this far in such a deeply troubled industry as airlines is a good sign that the much easier Yahoo situation can be settled.

Interestingly, under the proposed Delta-Northwest deal, Bostock would become vice chairman of the combined entity, which would use the Delta name.

Also a good sign–a willingness to shed your corporate independence and be OK with it.

So, no surprise, according to multiple sources I talked to yesterday, the roadshow by top Yahoo execs–CEO and Co-Founder Jerry Yang, President Sue Decker and CFO Blake Jorgensen–to tout the new growth plan the company unveiled last week was not such a hit with shareholders.

While the group met with polite audiences, most investors I talked to were unenthusiastic about the plan and dubious that Yahoo’s blue-sky hopes would come through. “I think we wanted to give Jerry a hearing, but mostly to save face,” said one investor, in a sentiment that was typical.

What Yahoo (YHOO) was selling, of course, has been a plea for time from shareholders and a way to signal Microsoft (MSFT)–which made an unsolicited bid for the company in the beginning of February–that a price rise was needed to complete the deal. In addition, so far, no alternative offers have panned out.

Thus, last week, Yahoo released information about its future prognosis, saying there would be no surprises for 2008 off guidance, strong gains in revenue and cash flow for 2009 and 2010 and a resulting share price closer to $40, $9 above the original $31 a share–the cash-and-stock offer is actually now worth about $29.50–offered by Microsoft. (See chart.)

Interesting, Microsoft has been unusually silent on Yahoo’s growth predictions, which to me signals: Unimpressed, not inclined to raise its price and increasingly bored waiting for the inevitable call to negotiate.

But that call, I think, will now have to happen–even though I would bet my precious “Beverly Hills 90210″ pilot episode DVD (seen here!) that Microsoft’s Morgan Stanley (MS) bankers and Yahoo’s Goldman Sachs (GS) bankers have been secretly communicating for a while now.

(Morgan to Goldman: “Ignore what the left hand is doing–it will stop gesticulating wildly soon and we can begin bargaining and collect our big fat fees!”)

So do others: “I now give it 14 days,” said one person who has experience in merger back-and-forth Kabuki dances. “There are no more moves to delay this, although you have to give Yahoo credit for its efforts.”

Extra credit even! But is that all there is?

Some at Yahoo do not agree. One person close to the company noted that Yahoo’s situation is like that of financial software maker Intuit (INTU), which was not bought by the software giant in 1994.

“Remember what happened to their deal with Microsoft?” said the person.

Actually, I do. After a lot of behind-the-scenes pressure from Microsoft, Intuit Founder and CEO Scott Cook struck a deal with Microsoft’s Bill Gates in which the company got a 40% premium, or $1.5 billion in Microsoft stock.

That deal was only scuttled, when the Justice Department stepped in and threatened to file suit to stop the union.

Thus, Yahoo’s only hope is the Justice Department, defanged under the Bush administration and with the existence of a major online rival like Google (GOOG) to point to as competition?

It could happen, I guess. But, I would have to say: Count me dubious.

Please see this disclosure related to me and Google.

RockYou, widget maker, is the latest example of a sane valuation heartbreaker, as it is undertaking efforts to secure an investment from mainstream financing firms that would value the company at between $300 million and $400 million.

First reported by Valleywag last night, the start-up, said one source, “is being squired around Wall Street” by investment behemoth Morgan Stanley (MS), in search of the same kind of deal its rival Slide got in January.

BoomTown broke the news of that deal, which nabbed Slide $50 million and a $550 million valuation with investments from blue-chip investors T. Rowe Price (TROW) and Fidelity.

Thus, RockYou’s motto: Anything Slide can do, we can do slightly smaller!

And, indeed, not to be SuperPoked by Slide CEO and Founder Max Levchin, sources said RockYou Co-Founders Jai Shen (also CTO) and Lance Tokuda (CEO) were quickly on the march for their own payday.

It is, in fact, a quest that a lot of Web 2.0 companies seem to be on, since the sector’s fearless leader–Facebook–got its $240 million and $15 billion valuation from Microsoft (MSFT) last year.

All of this frantic funding activity is, of course, this bubble’s version of going public–grab big cash investments from investment firms and hedge funds, desperate for a good bet on the sector, without the pain of public scrutiny of questionable business prospects that did in Web 1.0 shooting stars.

It’s that or get bought for an ungodly sum by equally desperate Web 1.0 companies (See: AOL+Bebo).

Sources close to RockYou, which has had acquisition feelers put out to it from larger companies in the past, said the company has had several strong offers of funding, but it is trying to select the right partners for the latest round of funding.

“We want our investors to be strategic and helpful to the company,” said one person close to RockYou.

RockYou has so far been funded by Sequoia Capital, Lightspeed Venture Partners and Partech International.

(Interestingly, Sequoia backs another instant messaging and chat widget maker, Meebo, which is reportedly seeking a $250 million valuation, which I posted about here yesterday).

To be fair, makers of highly distributed third-party apps like RockYou are garnering immense traffic and their widgets are syndicated everywhere. RockYou’s Super Wall, which lets you turbocharge your digital wall, for example, is one of the most popular on Facebook.

Other RockYou apps include: X Me, a communications tool that allows you to “Hug Her, Slap Him, Tickle Them!”; and Likeness, where you can “compare yourself with friends and movie stars like Angelina Jolie, Jessica Alba, Keira Knightley and many more.”

The company has been trying to monetize all this traffic and popularity and distribution, as well as knowledge of user behavior, by offering advertisers new forms of engagement.

But the jury is still out on these interesting but unproven efforts by all the social-networking players.

In any case, the money is apparently still flowing into these start-ups, taking a chance on them being the next big media play.

Here are two videos I made when I visited RockYou’s offices in San Mateo, Calif., last October, after I had called the widget market juvenile and faddish.

The first is my tour of the office, where I was playfully accosted by an infant–oops, a RockYou engineer–in a suit. The second is my interview with Shen and Tokuda.

One of the more unusual situations in the current stand-off between Yahoo and Microsoft is the stress it has likely put on the longtime professional relationship and personal friendship between Yahoo President Sue Decker (pictured here) and Blackstone Group’s Jill Greenthal.

That’s because Greenthal (pictured here) is advising Microsoft on this deal, along with Chuck Cory and Paul Taubman of Morgan Stanley (who was actually Time Warner’s banker in its disastrous AOL deal).

Yahoo is being repped by Goldman Sachs, Lehman Brothers and Moelis & Company, an advisory boutique. All the firms on both sides stand to reap hundreds of millions in fees, if the deal is consummated.

Greenthal is a good pick for Microsoft to get the job done. She has a long-time knowledge of Yahoo, having worked with the company when she was at the Credit Suisse Group on the $1.45 billion purchase of Overture, one of Yahoo’s smarter purchases.

And her ties to Decker go back even further, when Greenthal was a banker at Donaldson, Lufkin & Jenrette. The pair worked together frequently at DLJ, where Decker was an analyst and research director before heading to Yahoo.

Back in 2003, in a BusinessWeek profile of Decker, Greenthal noted about Decker’s tenure at DLJ: “[Executives] didn’t always like her opinions of their company or industry, but they respected her.”

A source in Silicon Valley who knows both Decker and Greenthal said that the two have avoided speaking since the unsolicited Microsoft bid was launched by Microsoft CEO Steve Ballmer in an evening phone call to Yahoo CEO and Co-Founder Jerry Yang two weeks ago.

But one might also imagine their bond could also become a critical bridge in bringing the companies to finally make a deal, as many big shareholders are urging and Yahoo has been resisting.