Yesterday, after Disney named two longtime Internet execs–Playdom’s John Pleasants and Jimmy Pitaro of Yahoo–as co-presidents of its Internet unit, BoomTown did a longer interview with CEO Robert Iger about the entertainment giant’s next Web moves.

I always enjoy talking digital with Iger–who is pictured above in an interview I did with him in 2006 at the fourth D: All Things Digital conference–since he has been one of the old media moguls who seems unafraid of the challenges of new media.

While appropriately wary, Iger acted early and often in exploring digital initiatives at Disney (DIS) that others in Hollywood’s and New York’s media worlds were loathe to consider.

“I have tried to keep two obvious philosophies,” Iger said in a phone interview yesterday. “First, that our current business not get in the way of adopting new technologies, and, second, that our business belongs on these new platforms.”

Easy to say, of course, but it’s still nice to hear, given the longtime, incessant and ultimately wearying push-and-pull between those who make bucks making content and those who make bucks making technology.

“My premise is that technology is about an opportunity for us,” said Iger. “And we cannot will it away and should not…because you can’t stop these things from happening.”

That’s presumably the impetus behind the hiring of Pleasants and Pitaro (picture here, left to right).

With an assist by recent Disney board member and Facebook COO Sheryl Sandberg, Pitaro came to his attention earlier this year, Iger said.

Pitaro left his job as SVP of Media at Yahoo (YHOO) last week.

And Pleasants was CEO of Playdom, the online social gaming company that Disney acquired for $763 million in late July.

The pair, who will report directly to Iger as co-chiefs of the Disney Interactive Media Group, replace outgoing head Steve Wadsworth.

The shift is a big move by the entertainment giant and yet another attempt to clarify and bolster its Web strategy, which has had a long and often rocky history.

Under the previous regime of former CEO Michael Eisner, for example, Disney bought search engine Infoseek and tried to create a portal called Go.com.

That failed, and was one of many efforts to define the media company’s Web goals.

More recently, in 2008, Disney gathered most of its Internet properties within DIMG, under Wadsworth.

Still, money-making not been part of the mix. In its most recent quarter, DIMG lost $65 million on revenue of $197 million.

In the interview about the new structure, Iger said: “I think we’ve built a framework of assets, and now is the time to create a structure in a more focused way. In splitting the divisions, we can focus more on them better and in a way they deserve.”

He outlined the new set-up, which will have Pleasants focus on the online gaming and mobile landscape and Pitaro on the Web arena.

Iger said he felt Pleasants and Pitaro brought different backgrounds to the task, as well as longtime experience in the Internet arena.

He said that upon considering a fresh approach, he felt that Wadsworth was “spread too thin,” given all the various online arenas for Disney.

In fact, today, Disney owns a number of big Internet properties, including Disney.com, Family.com and Club Penguin, although there does not seem to be a particularly cohesive strategy among them.

Of course, that’s not surprise, given it is all part of a multifaceted media company with a variety of businesses.

Due to its powerful content assets, said Iger, it might be a perfect time for a more cogent plan. With the explosion of devices, such as the Apple (AAPL) iPad and others, the importance of cooperation between content and technology is more critical than ever.

“I think a lot of technology companies are really finally ready to handle more premium content in a way that is beneficial to all of us,” said Iger.

And, he added, it was time for Disney to get more involved in technology, which was the reason for the purchase of Playdom. The move has made it more a publisher than a licensor.

“If we wanted to get significant in size, we need the investment to be greater,” Iger said about the big payout to get into the fast-growing social gaming arena.

And that has meant less emphasis on console games, on which he said Disney had focused too much in the past.

No longer–now Iger said has planted Playdom, as well as its purchase of the Tapulous music app start-up, in a spanking new facility in Palo Alto, Calif., right in the heart of Silicon Valley.

“We need to be part of the culture and world there in a significant way,” said Iger. “And I believe I have convinced the senior team within Disney that Playdom is a huge opportunity for them.”

That includes online gaming related to units such as sports at ESPN, as well as other Disney brands, such as the theme parks or Marvel, into Playdom games.

While Pleasants will run his part of the show from Silicon Valley, Iger said, Pitaro will work out of Los Angeles on Web initiatives and in upgrading the Disney online experience.

“We want to make Disney sites more of a community and entertainment center than a marketing hub,” said Iger. “Where is gets complicated is the levels of exclusivity and the other places we want to distribute our content.”

That includes being part of the premium Hulu online video site, as well as perhaps even creating a Disney-branded pay service, but also being open to working more with Netflix (NFLX).

And that means a multifaceted approach to all kinds of payment models for Disney online, from subscription to advertising-supported to pay-per-view.

“In certain areas, we will be very aggressive with our content and in others less aggressive, to the extent that each offers us revenues,” said Iger. “Obviously, where there is potential cannibalization, we will be a little more careful…but we are going to push forward.”

When asked about the most obvious management issue–the possibility of clashing with two head of one division (MySpace, anyone?), Iger said that while there was overlap, he thought the jobs Pitaro and Pleasants had to do were also wide-ranging and different enough.

Plus, added Iger, “They both report directly to me and I am there to see to it that it works.”

In other words, as Disney continues to move forward into the digital future, the content and technology buck stops, as it should, at Iger.

Former VP and full-time envirogod Al Gore, who appeared at the fourth D: All Things Digital in May 2006, turned out to be a very funny guy onstage.

And he’s funny on television too, as you can see from his hysterical appearance this past weekend on “Saturday Night Live.”

In the bit, Gore talks about getting his crazy on to get folks to not forget about global warming.

Enjoy the video:

For many years now, one of our regular attendees at the D: All Things Digital conference has been award-winning movie and television director, producer and writer Barry Sonnenfeld, who is–as it turns out–a not-so-closeted geek in his spare time.

(He also appeared onstage in 2006 at D4 in an interview with Walt Mossberg, which you can see here.)

In fact, the man behind movies like “Men in Black” and TV shows like “Pushing Daisies” (and who likes to sport a Stetson and cowboy boots 24/7) does a gadget review column for Esquire magazine called “The Digital Man.”

Now he is branching out to a vlog about his geek passions on Crackle, which will appear every two weeks from wherever he is–either from his homes in East Hampton, N.Y. or Telluride, Colo., or from movie or TV sets.

And, compared to the cinéma vérité style of BoomTown (translation: shaky filming and bad sound), Sonnenfeld’s vlogs are pretty high quality, although they are not too overdone as those from Hollywood types always are, and it’s hard not to admire the editorial use of a martini.

Here’s his intro video vlog below, as well as one about a cross-country trip Sonnenfeld and his “analog” dog, named Lucky, took in a 2010 Ford Taurus SHO (super high output) and another about his experience helping his wife, Sweetie, cook for some film industry friends using the Traeger Professional Wood Pellet Grill.

Next week: A chain saw, although I hope Sonnenfeld will go light on the martinis for that demo.

From Crackle: The Esquire Digital Man Preview:

From Crackle: Ford Taurus SHO:

From Crackle: Traeger Professional Wood Pellet Grill:

Bob Iger, CEO of the Walt Disney Company (DIS), was the kickoff interview onstage at Fortune magazine’s Brainstorm Tech conference, which is taking place over the next three days in Pasadena, Calif.

The event is packed full of Web and media luminaries.

So, BoomTown will be sitting in the front row and liveblogging some of the sessions here, including this one, titled, “Digital Kingdom: New Business Models for a Media Giant.”

Translation: When you Twitter upon a star, makes a–big–difference what you earn.

Which, right now, is not a whole lot, as Iger and others in the media business know all too well.

But let’s set the scene: Iger looks like a very typical old-media mogul you might order from an online catalog–handsome, suave and sophisticated, a perfect mix of Hollywood and New York.

Thank goodness, then, that he never seems to have acquired that other irksome characteristic of some of his peers–a full-bored panic over the Internet.

In fact, Iger–whom I also interviewed onstage at the fourth D: All Things Digital conference in 2006–has been unusually fast-forward among many of the big media companies in facing the digital music and dancing.

Fortune writer Richard Siklos asked him about a mishmash of subjects, from subscription services to authentication to cable providers, all of which center around a basic question:

How the heck is Disney going to be paid for its wares–because someday those agelessly lucrative “kids” from “High School Musical” are not going to agree to yet another reunion?

“This is the beginning of the beginning,” said Iger, who noted that it would be folly to guess what’s coming next in the digital arena.

A most excellent point that he made several times, adding that it was important for companies like Disney to keep trying out all sorts of things digitally, until they got it right.

“This notion of protecting the present is something that I talk a lot about [with employees],” said Iger, who wants them not to do that so much.

He noted that running a modern media company meant you had to have “one hand in the present and one hand in the future.”

Iger forgot about the hand that you might need to protect yourself from partners of the present–like big-box retailers, television affiliates, cable networks–who are going to come at you with a cudgel for giving the stuff you sell them away free on, say, Hulu.

Hulu, of course, is the popular, tiny-money-making premium online video service, which is a joint partnership of News Corp. (NWS), GE’s (GE) NBC Universal and now Disney.

“We believe in Hulu,” said Iger, who thinks its business model–currently just online advertising–might evolve over time.

But, he added, he was “somewhat skeptical” of any one answer to what is ahead.

As in: Iger just does not know, which is probably the best thing a media mogul can say right now.

Except for one thing he said is always mindful of–to follow, “where the consumer is going.”

Consumers are going online, of course, which is certainly going to require all-hands-on-deck at Disney in the years ahead.

[Update: It seems Disney was keeping its hand in the present for today, as it apparently had YouTube take down a trailer for its new "Alice in Wonderland" movie, which was set to debut at Comic-Con International in San Diego tomorrow.]

Oh, Scooby-Don’t…

You could not be more wrong in your post last week–titled, “Why Kara Swisher and Walt Mossberg are wrong about naming Web 3.0 ‘Web 3.0′”–about Walt and I being wrong about naming Web 3.0 “Web 3.0″ in an essay we posted at the start of our D: All Things Digital conference, which took place last week.

I know writing “Kara Swisher,” “Walt Mossberg” and “Wrong” is well-nigh irresistible, but your solution of calling the digital era we are in the “2010 Web” is equally confusing and incorrect.

So, since you know I love to do translations, let me try to take apart your entire piece paragraph by paragraph:

What Scooby-Don’t wrote: Can we just head this trend off at the pass? It seems that Kara Swisher and Walt Mossberg, at their “All Things D” conference announced the beginning of the Web 3.0 era.

And I’m not the only one to think so.

BoomTown response: Walt and I simply wrote an essay in which we said we thought mobile and smart phones were super important as the next platform and represented what we thought Web 3.0 innovations, such as social networking (which we also think is important, by the way) would pivot around.

We didn’t “announce” anything, although that does sound awfully grand.

But so what if we did, because it happens quite a lot?

Dan Gillmor, for goodness sake, declared it Web 3.0 in 2005. His take was different:

“The emerging web is one in which the machines talk as much to each other as humans talk to machines or other humans. As the net is the rough equivalent of a computer operating system, we’re learning how to program the web itself.”

And in 2007, Tim O’Reilly weighed in on it, responding to Web 3.0 theses by Jason Calacanis and Nova Spivack, and also noting Stowe Boyd’s thoughts on the subject.

You get my point, Bobby? Lots of folks have opinions about what is Web 3.0, much as they will when we start arguing over what Web 4.0 is.

At Web 5.0, of course, a self-aware Google (GOOG) will have begun its inevitable war with the human race, sending back a cyborg to terminate you before you wrote that post, thereby making this rebuttal moot.

But, I digress!

Scooby-Don’t wrote: Short aside: It’s interesting that neither Kara nor Walt show up very often on friendfeed, which is the best example of the 2010 Web right now. Kara Swisher has made a total of five comments there. Walt is even worse, doesn’t bring any items in there, and only has six comments. How can you know what the 2010 Web is, if you don’t use it and don’t participate in it?

BoomTown response: The fact of the matter is that neither Walt nor I like to use FriendFeed as much as you do. I daresay that no one likes to use FriendFeed as much as you do.

Thus, hinging a larger point to this, just because we don’t play in a particular sandbox you like to play in, feels a little too much in the digital weeds to me.

Just because you have chosen to be the unofficial spokesmodel for the very laudable service–about which I have done a very lovely reported post on complete with video–I am not clear why you need to accuse Walt Mossberg and I of not being social because we don’t use it as much.

We both just happen to prefer Twitter and blogging as our social outlets.

I have done 3,255 updates on Twitter since I started last year, for example, which is certainly not as much as your 21,224. But–and I think we can all agree–as blabby as I am, I am simply not as blabby as you.

So, let’s try to make this as clear as possible.

We. Don’t. Use. FriendFeed. Regularly.

As I said, we use Twitter, we use Facebook, we use SMS, we use blogging and we use a whole lot more. In fact, between us, we try out pretty much everything.

While I appreciate that FriendFeed seems to be your home planet of the moment, it is not the only place to realize your term, 2010 Web, and it feels very Web 1.0 to say so.

Scooby-Don’t wrote: The Web does NOT have version numbers. Naming what was going on in the last eight years “Web 2.0″ did us all a large disservice (Tim O’Reilly did that, mostly to get people to see that there was something different about the Web that was being built in 2000-2003 than what had come before).

But by naming it a number, I believe it caused a lot of people and businesses to avoid what was going on and “poo poo” it as the rantings of the new MySpace generation (which was just getting hot back then).

BoomTown response: Let me see if I can get this straight. You can call it 2010 Web, but we cannot use version numbers, such as Web 3.0?

Hey, we’ll call it Britney Spears if we want!

Actually, I like naming the next era of the Web after the always volatile entertainer. She’s mobile, ever-changing, ubiquitous and always entertaining! Also, there are several eras of Britney: Sweet, Timberlake Lady, Federline Lady, Young Mom, Nuts, Nuttier, Nuttiest, Hospitalized, Medicated.

My main point remains: Who died and made you Boss of Pointless Internet Catchphrases?

Scooby-Don’t wrote: See, the Web changes EVERY DAY and a version number just doesn’t do it justice. Think about today, we saw Microsoft (MSFT) announce a major new update to its search engine, named “Bing,” that turns on next week and is already getting TONS of kudos. Seriously, in the rental car shuttle today a guy I met said the demo he saw at Kara and Walt’s conference was “awesome.”

Also today was Google’s Wave, which caught everyone by surprise and which sucked the oxygen out of Microsoft’s search announcements. Check out all the reports that I liked from around the world this morning.

BoomTown response: The Web changes EVERY DAY? You’re kidding! We had no idea! Thanks for that critical morsel of info!

Earth to Robert: Walt has spent a large part of his life writing about the panoply of new devices that have come out in an unceasing flow and I have written at least 10,000 news stories and two books about the Web since the early 1990s.

Pretty much all we write about is how the Web changes every day. Actually, every second.

Scooby-Don’t wrote: But, back to the theme of this post. There IS something going on here. I covered it a few weeks ago.

7. Hybrid infrastructure. At the Twitter Conference this week lots of people were talking about how they were using both traditional servers along with cloud-based approaches from Amazon (AMZN) and Rackspace (RAX) to store, study, and process the sizeable datasets that are coming through Twitter, Facebook, and friendfeed.

BoomTown Response: We had folks on stage at our D7 conference discussing all this last week. In fact, we covered a whole lot more than that, which you can read about if you click on through.

While I think all yours are also interesting ideas, I am still not clear why you need to get your knickers in a knot, since we happened to think mobile platforms and smart phones are more important trends at this juncture.

Also, could please explain how Google “caught that wave big time Wednesday when it handed Android phones to everyone at its IO conference.” Google is innovative because they give free swag to folks?

We gave free swag to folks this week at D7, so I guess that makes Walt and I 2010-Web-worthy!

Scooby-Don’t wrote: So, why doesn’t a version number work for these changes? Because they don’t come at us all at once. A lot of these things have been cooking for years. The Internet makes iteration possible. Tomorrow will be better on the Internet than today. In the old world of software you’d have to wait for the compilers, then you’d need to distribute tons of CDs or disks. That no longer needs to be done.

Same with the Web. Calling it the “2010 Web” puts an urgency into what’s happening. If your business isn’t considering the latest stuff it risks looking lame or, worse, leaving money on the table. Just like driving a 1994 car risks looking lame or, worse, breaking down a lot more often than a newer car.

BoomTown response: Actually, I would have to say that your year numbering system is deeply confusing and I am not sure we can treat Internet development like some auto or, even, say, fine wine.

Ah, that 1995 Web was saucy with a smooth Netscape IPO finish, while 2001 had a disappointing popped-bubble tone, due to the excessive tannins of Pets.com. Now, the 2009 is still very young, but it has a frothy Twittery taste, which goes surprisingly well with brie.

Scooby-Don’t wrote: Is the year metaphor perfect? No, I’m sure there are a few things wrong with it. For one, if you want to host a conference based on the “trend” you’ll have to change your conference name every year. That costs money, which is why conference companies like to have more stable trends that they can exploit for a few years, at least.

BoomTown response: D1, D2, D3, D4, D5, D6, D7. So far, changing the number has worked out well for us that we’re going to go for D8!

Scooby-Don’t wrote: Also, there are some clear “eras” in the Web, so I could see wanting to suggest that we’re in the third era of the Web, but I’ve been studying this for the past eight years and calling the second era “Web 2′ actually held us back because mainstream users didn’t think anything was happening in the past few years and Web 2.0 became a useless phrase anyway.

BoomTown response: You must know that mainstream users don’t pay one bit of attention to any and all of the dumb terms Silicon Valley comes up with.

And, with all the obviously massive change that has happened in the past few years in tech and the Internet (iPhone, Kindle, Facebook, Twitter to name a few), it seems odd to say that anything has been held back.

Frankly, it would be nice if tech innovation took a breather once in a while.

Scooby Don’t wrote: Anyway, can we use year numbers to describe the Web now? It’ll make it easier to evangelize the modern world to businesses. We’re entering the 2010 Web, that’s what I’m exploring. Calling the Web a version number is for people who don’t really understand, or participate in, what’s going on here. Kara and Walt, you gotta do better here.

BoomTown wrote: What’s in a name?

Well, it’s dang easy to attack, of course, instead of actually discussing the actual premise that we were outlining in our essay, titled “Welcome to Web 3.0.”

As we wrote:

“So what’s the seminal development that’s ushering in the era of Web 3.0? It’s the real arrival, after years of false predictions, of the thin client, running clean, simple software, against cloud-based data and services. The poster children for this new era have been the Apple (AAPL) iPhone and iPod Touch, which have sold 37 million units in less than two years and attracted 35,000 apps and one billion app downloads in just nine months.”

So, if you want to just focus on the name, then you gotta do better here.

Until then, you say 2010 Web, we say Web 3.0 and let’s call the whole thing off.

One of our favorite D: All Things Digital speakers, and now a regular attendee, has been Hollywood director, producer, writer and big-cowboy-hat-about-town, Barry Sonnenfeld (pictured here at D6).

So, BoomTown extends belated but Texas-sized congratulations to Sonnenfeld for winning an Emmy earlier this week for directing the pilot of “Pushing Daisies” on ABC.

A gadget freak, as well as an entertainment mogul, Sonnenfeld was very entertaining and insightful about Hollywood’s uncomfortable relationship with technology in his interview with Walt Mossberg in 2006 at D4 (and which you can find here in photos and video).

Backstage at the Emmy Award show, which annually fetes the television industry, Sonnenfeld–who always tries to get Walt and me to ask outrageous questions of speakers at the conference in exchange for walk-ons on his shows and movies (so far, we have not bitten, although he has gotten off some good ones as an audience member in the Q&A part of the interviews)–gave a typically saucy interview to the press about his win.

And, no surprise, Sonnenfeld did manage to deliver one perfect geeky quip, as the music cue started to cut off his speech on Sunday night, which I doubt the glam crowd there got, but was not lost on me:

“Love TV and fear the Internet.”

So far that we put all those bendy-straws-in-the-wind television pundits to shame!

Case in point: At D4, we invited former Vice President Al Gore to come just before everyone decided he was the best thing since organic whole-wheat sliced bread.

And at D5, held last May, we invited Sen. John McCain of Arizona to talk about things like tech policy and Iraq, during a time when most had written him off in his bid for the Republican presidential nomination.

Not so, it seems, after Comeback Jack’s big win in New Hampshire last night.

Given our powerful psychic political skills, we are keeping our next political selection sealed in a mayo jar in the back of ATD HQ.

But to see what McCain is all about, here’s an hour-plus interview with McCain by Walt Mossberg and me: