If at First You Don't Succeed, Try, Try Again…

Was it just me or did you also get a bit of déjà vu upon reading a story today by the New York Times’s Laura M. Holson about yet another mash-up of a Hollywood talent agencies with Silicon Valley VCs.

That’s apparently what is happening with a new investment venture that includes the William Morris Agency, Accel Partners, Venrock and–filling out the unlikely foursome–AT&T (T), as a limited partner.

The focus of the investment fund will be to hand out cash–and, presumably, expertise–to digital media start-ups in Southern California.

While the Times drilled in on the presence of a big cellphone carrier–just the kind of company that my partner Walt Mossberg has dubbed one of the “Soviet ministries” for stifling innovation with overly controlling behavior in the mobile space–I am more focused on the rocky road of many such deals that have been struck in the past.

Now, I think all the players involved are very smart, including Accel’s Jim Breyer, Venrock’s David Siminoff and also William Morris CEO Jim Wiatt (as well as Morris’s Paul Bricault).

That said, a lot of sharpies have gotten sucked up in the past into the this-has-to-be-a-marriage-made-in-heaven dreams of the perfect Hollywood-Silicon Valley pairing.

Today, there are a number of interesting efforts, such as Comedy Central’s deal with the creators of “South Park” to create a joint-venture digital studio, as well as the better-known pairing of Sequoia Capital with the Will Ferrell-led Funny or Die comedy site (see my video interview with Sequoia’s Mark Kvamme about the site below).

And, of course, although nothing was actually settled, the recently ended writers’ strike was all about content revenues that might–or, perhaps more accurately, might not–be coming from digital sources in the future.

But if the past is prologue, this new group of investors might have to learn to be a bit patient.

Breyer acknowledges as much in the Times’s article. “There is always a fear, I know, that the bubble is about to burst when a parade of actors and actresses comes through my door,” he said, before noting, “this time the discussions are much more rational.”

I guess that is why the funding is in the tens of millions of dollars, the article noted, rather than the larger sums that have been spent in previous attempts to forge these kind of tech and entertainment alliances.

In fact, Holson herself penned a very good piece in 2002 about the failure of one much-touted experiment in such an integration–LivePlanet–between celebs Ben Affleck and Matt Damon and Redpoint Ventures.

That company was supposed to be a multimedia wunderkind, straddling the tech and media worlds with all sorts of gizmo-content wonders. One of its debut press releases in 2000 was, in fact, titled: “LivePlanet Unveils Integrated Media Concept–Entertainment Experiences that Span Traditional Media, New Media and the Physical World.”

Now, it is a shadow of that. According to a January article in Variety about the shuttering of its film unit, “LivePlanet evolved into a satellite company that [partner Sean] Bailey, Affleck and Damon would return to when not engaged in their own projects.”

In the 2002 piece, after a series of problems, including the bust of the dot-com bubble, Affleck himself got it dead right.

”If we stick around long enough and convince people we can do these things, we will matter in the new economy. I’d like to slip to the last page to see how it ends. But who knows.”

And, even six years later, who knows?

Here is the Kvamme video, in which he discusses Funny or Die: