On the one hand, a childhood pal — Russell's mom was reportedly best friends with Levy's mom — can do far worse than guiding one to tens of millions of dollars in wealth. And Pilot Group did more than passively watch its investment grow. From what we hear, Pittman's salesmanship was key to growing Daily Candy's advertising base. Such involvement would be in keeping with Pilot Group's focus on taking a "control position" in its investments. After the investment firm acquired Daily Candy, the newsletter's subscriber count grew tenfold to 2.5 million.

But not everyone buys that version of events. Said the tipster, an AOL veteran who followed Daily Candy closely:

For Pittman to brag that subscribers have increased since he made

the investment is just private equity puffery and delusion. That

would be like my grandmother taking credit for the business success of

the stocks she owns.

Perhaps Russell's help was not so selfless. As our source notes, Russell's advice on the deal would have been "highly conflicted," Russell having worked for Pittman for several months before the Daily Candy investment closed in late 2003.

His line to other potential portfolio

companies and strategic partners is that through his friendship with

Dany, HE was responsible for the early success of Daily Candy as a

startup, so he didn't feel compunction about duping the original

shareholders... Whatever the case, Pittman was not a genius to have his

junior guy abuse a family friendship in a predatory deal.

Let this be a lesson to startup founders who are not yet sufficiently cautions about venture capital investment, or who spend too much time worrying about whether their fameball girlfriends really truly love them for the right reasons: If you're not careful, you might have to settle for a paltry $25 mil when the big payday comes. After taxes, you'll barely be able to afford a decent loft!

Bob Pittman's claims to have founded MTV were overstated, but he was closely associated with the cable music channel's gigantic success in the 1980s. It was said of his wife Sandy, who later attempted to conquer Everest, that she gave a new meaning to the term "social climber." And Pittman himself was equally ambitious on the Manhattan circuit, though he scaled the social and business heights with a good deal of charm and grace.

The one-eyed mogul, now 54 years old, came tumbling down after he took over management of revenue-inflating AOL during the bubble. The online access service cashed in on the funds being invested in late 1990s dotcoms, much of which was spent on advertising partnerships which gave the startup brands a place on AOL pages.

The Dulles-based online service was never going to survive unscathed a downturn and the erosion of the dial-up market, and Pittman's reputation would have suffered anyway. But the infamous 2000 merger between AOL and media giant Time Warner ensured he would not merely be despised by investors who bought into AOL at its revenue-inflated peak; he personified to Time Warner veterans the arrogance and empty rhetoric of the AOL upstarts. Pittman managed to sell $94m in stock in the aftermath of the merger, but the dilution of Time Warner shareholders ensured the hatred of a large part of Manhattan's media establishment.

Pittman's contribution to Daily Candy has been more constructive. His salesmanship transformed Dany Levy's cute little newsletter into a marketing machine for fashion and retail brands. Pittman's reputation as a canny internet investor is made by this transaction, by some measure the best return of his fund. To be sure, the web may eclipse email as the preferred online medium for advertisers, and Comcast may have bought a property that's past its peak. But the cable company's bosses are in Philadelphia, a city that Pittman can easily avoid. In terms of Manhattan media, the former wonderboy is back.

The venture is called the Zynga Game Network and it's the company behind social network apps such as "casual games" Poker, Attack, and Battleship. So far, Zynga makes all its money by promoting other applications, earning 50 cents each time a user installs one on their profile.

Pincus told the New York Times Zynga has already broken even and has not yet tapped into any of its venture capital. Users click on about 50,000 links to application install pages each day.

Let us know when Coca-Cola buys ad space. Until then, the Facebook application platform will remain a viable economic ecosystem like the Hapsburgs were a model of genetic diversity.

An email list might seem too 1999 for geeks more apt to find a new nightspot via Yelp or Twitter. But even though most of Silicon Valley has written off email for good, delivering its content over the ubiquitous technology seems to work for Thrillist. As Lerer notes, because readers have to sign up for Thrillist, "advertisers value impressions we deliver much differently." By differently, he means more.

We like Lerer — so much so that we're going to help him move into the 21st century. Any number of services allow you to convert email subscriptions into RSS feeds. Valleywag has signed up for Thrillist SF at one such website, Mail2RSS.org. The feed is here.

(Photo by kyle simourd)