All Things Digital

Oh, there had to be much, much gnashing of teeth in the corporate offices of the Time Warner Center in New York yesterday with news of the sale of DailyCandy to Comcast for $125 million.

Why?

Maybe because that tasty payment is going right into the hands of Bob Pittman’s Pilot Group Ventures, which bought the fashion and shopping newsletter business for $3 million in 2003.

Longtime media exec Pittman was the former star AOLer, whose nickname was Bob “Pitchman” for his smooth-as-silk selling and even more marked spinning skills.

But the Web 1.0 supernova fell quickly to earth, after the online service merged with Time Warner (TWX) in early 2001, in what is now considered one of the more significant world-class corporate disasters.

After being tossed out of AOL Time Warner in mid-2002, Pittman (pictured here), along with AOL head Steve Case, was blamed for the stock decline and other woes at the media giant by the Time Warner side, whose deep bitterness toward him has never really faded away.

Now, with Time Warner trying to make a deal to sell the AOL unit for up to $10 billion to Yahoo or Microsoft–despite it being valued at $20 billion only a few years ago–Pittman’s small but impressive score has got to grate.

“I have been associated with the start-up, turnaround or acceleration of many companies and major brands, and rarely have I seen the kind of creativity, commitment and passion I’ve seen day in and day out at DailyCandy,” said Pittman in a letter to DailyCandy staff yesterday about the sale. “And the results speak for themselves: Since we made our investment in 2003, subscriptions have grown from just over 200,000 to over 2.5 million.”

In the letter, Pittman said the company’s EBITDA was over $10 million this year on revenues of $25 million.

This is certainly different from the situation almost exactly six years ago when Pittman was driven out of the then-named AOL Time Warner on the proverbial rail.

If you want a taste of those once-grim times for Pittman, here is an excerpt from my book, “There Must Be a Pony in Here Somewhere: The AOL Time Warner Debacle and the Quest for a Digital Future,” which was published in 2003.

The section comes from Chapter Six, “Way, Way After the Goldrush,” as the deal imploded:

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As BoomTown argued yesterday in a piece on the landscape of Yahoo if Microsoft completes its purchase of the Internet portal, Yahoo (YHOO) certainly knows how to make online content.

As we wrote: “For all its history, right down to today, even with all these dumb widgets competing for users’ attention, Yahoo continues to natively understand how to to entertain, inform and serve up their own and others content to consumers.”

Case in point, an attractive new site it launched today called Shine, which is aimed at women from their mid-20s to their mid-50s.

As you can see from the image below, it is a very well-done site, incorporating a lot of the good stuff in the same genre from around the Web.

Does it look a bit like the sassy properties of Sugar Inc.? Is it light and frothy like Glam Media? Does it feel a bit like DailyCandy, in its focus on the shopping as a sport? And, is it as helpful as iVillage (and does it even “borrow” a wiggly “i”)?

Yes indeedy to all!

Imitation is a form of flattery, I suppose, although Yahoo’s site feels fresher than any out there and it has an aspirational and hip feel that women will like, I think.

I’d call it an Eat-Pray-Love mood, with a lot of Oprah mixed in.

More importantly, it is clearly a good market for Yahoo’s advertisers, who all aim to reach this high-spending but underserved demographic online.

Yahoo is trying to reinvigorate its lackluster efforts here, as well as making plans to further drill down into related topics like parenting, sex, food and wellness that are present on the Shine site now.

While it looks a lot like a blog plus, Shine obviously has social written all over it and a wide range of communications tools will be easy to layer over the service.

It also is smart in its partnering with lots of media companies like Hearst and in pointing across the Web to give users a more comprehensive offering.

But can Yahoo compete in a very crowded field with such a late entrant? Probably. It recently put up a celebrity site called OMG, which has grabbed significant traffic quickly.

And while we honestly could care less if men look bad in skinny jeans (um, yes!), there is probably something on the very-full page of interest to everyone.

The Shine site has Brandon Holley as its editor-in-chief, but the effort in the arena is being helmed by Amy Iorio, who is the VP/GM of Yahoo’s Lifestyles unit. It all rolls up under Yahoo Media SVP Scott Moore.

While Yahoo PR will probably blah-blah too much about “starting points,” which is the latest buzz word from top brass, related to Shine, it should just hush up and realize Yahoo’s many owned-and-operated media conglomerations just need decent support and promotion to stay as strong as they are and to keep them as one of the bright spots at the company.

Here’s a screen shot of the site (click on the image once to make it appear on another page and then again to make it larger):