“If consumers love something, we’ll figure out a way to scale and monetize it. If not, it’s a house of cards,” said Pittman, who has invested in successful companies like Thrillist and Zynga.

Pittman says he’s fine with the chaos that seems to be always enveloping media, preferring to regard it as a “byproduct of doing something a different way.” He also offered historic perspective on social media mania, noting that people have always consumed multiple media at once — for instance, by talking on the phone or looking at a magazine while watching MTV.

As for the failure of TV ad dollars to follow consumers online, Pittman said the “media mix is wrong” but that TV isn’t going anywhere soon.

Pittman also used the Ad Week chat, hosted by Medialink CEO Michael Kassan, to plug Clear Channel’s online radio service, iHeartRadio, which he says has reached 50 percent brand awareness.

Clear Channel’s iHeartRadio offers live digital feeds to more than 1,000 radio stations to a monthly audience of about 45 million unique listeners.

According to Yahoo, the relationship with San Antonio-based Clear Channel also involves cross promotion of content across both companies. For example, audio feeds of popular Yahoo video series will show up on Clear Channel radio stations across the U.S.

Also read: Does Yahoo even know how to be a modern media company?

Meanwhile, iHeartRadio content will be promoted on Yahoo platforms like OMG! and Yahoo Movies.

The deal will also include partnering on live events.

For example, Yahoo will become the exclusive web and mobile destination for music fans to stream the 2012 iHeartRadio Music Festival, which takes place Sept. 21-22 at the MGM Grand in Las Vegas.

According to James Heckman, Yahoo’s senior VP of strategy and emerging businesses, Clear Channel — like CNBC, ABC News and other recent Yahoo partners — offers his “horizontal media company” the chance to work with a conglomerate with deep ties into a vertical market (in this case, radio-delivered music).

“It definitely helps the perception of the Yahoo media brand among consumers and advertisers,” he told paidContent.

Also read: Yahoo’s video chief – how to get $3B closer to $50B

Meanwhile, the deal will help Clear Channel, which counts 237 million traditional radio listeners, further ramp up its internet footprint through a digital media giant that serveds 167 million unique users a month, according to comScore.

Heckman would not go into depth about the monetary aspects of the deal. “Both of us are going to have the ability to generate incremental revenue as a result of this partnership,” he said.

It’s Yahoo’s second music deal in as many days; Spotify users now have direct access through Yahoo.

But Pittman, who also invested in Clear Channel, only planned to work part time. It didn’t work out that way.

Effective immediately, Pittman is CEO of CC Media Holdings; Mays remains chairman. Pittman will join the boards of CC Media Holdings and Clear Channel Communications, Inc.; he also will serve on the board of Clear Channel Outdoor Holdings, Inc., as executive chairman. (More details in the release.)

He’ll stay with The Pilot Group, his private investment firm. His investments include The Huffington Post (sold to AOL), DailyCandy (sold to Comcast) and Zynga. Pittman initially invested $5 million in Clear Channel.

The Clear Channel promotion puts him in charge of 850 CC stations in 150 cities with a monthly reach of 159 million; Premier Radio Networks syndication that reaches another 4,000 stations; Clear Channel Digital; media services including the Katz Media Group; and 1 million or so displays in 40 countries including airports and Times Square. The company was taken private by Thomas H. Lee and Bain Capital Partners in 2008 for $17.9 billion.

For the past 11 months, Pittman has focused on working with Clear Channel Radio CEO John Hogan to shift Clear Channel from a radio company with digital to one perceived as a media and entertainment company. They acquired cloud-based music service Thumbplay Music to integrate the technology into IHeartRadion, the digital radio service that lets listeners tune in to Clear Channel stations across the country.

The new version of IHeartRadio, designed to compete with Pandora (NYSE: P) and other music services, launched late last month with a Las Vegas music festival billed as the largest live concert event for radio. (Previous digital head Evan Harrison initiated the IHeartRadio — then known as iheartradio –streaming strategy, including the first apps.)

When I sat down with Pittman in his mid-Manhattan offices for a long chat this summer, he talked about taking one what was supposed to be a part-time job. “I’m so into this I can’t even stand it. A month in, my wife said, ‘you’re not working part time. You’re working harder than you ever did at Time Warmer.’ I said, yeah, but I’m enjoying myself.”

Why Clear Channel? “They’re three times the size of the next largest radio company. They’re bigger than the biggest TV networks. They rival the big internet players in the U.S. for reach…. and they’ve got these big brands.”

Pittman is all about matching brand and convenience. “I’ve always said I can only be in a consumer-facing business ’cause my only real skill is reading consumers. It’s amazing when you think about the consumer that’s actually the same human being whether I’m trying to sell them a house, trying to get them to subscribe to AOL, getting them to listen to MTV, getting them to listen to radio — whatever it was, it’s always the same human being.”

Those same human beings fall in love with brands. “The only time they’ll consider other brands is when their brand isn’t there.”

He added, “The second thing consumers do is they’ll always go for convenience. If you can figure out a more convenient product, you’ll win, a better product doesn’t necessarily win. That’s one of the arguments I always have with developers. ‘Is it one less click?’ ‘No, it’s one more but it’s better.’ We’re not going to do that.”

He has been CEO of MTV Networks; AOL Networks; Six Flags Theme Parks; and Century 21 Real Estate, among others, and COO of America Online and AOL Time Warner.

“Every business I’ve been in it’s all about that. That guides me and drives me, and it’s the prism I use. Knock on wood, it has not failed me yet.”

In the combo biz dev and marketing role designed for him, Harrison will be responsible for spearheading “creative marketing approaches” across Van Wagner’s businesses, from premium billboards in Times Square and other top markets to sports and aerial. He’ll also be looking for potential expansion into other area. He’ll report to CEO Richard Schaps.

Harrison told paidContent he spoke with a number of large companies and looked at some VC-backed opportunities — “all the typical jobs you might imagine me taking” — but was struck by the potential of working for an established but nimble private company interested in growth. “I have never seen myself as digital only or music only,” Harrison said. He looks at billboards today with new technology and the possibilities of interactivity via QR codes or other means and sees something that compares to radio when he joined Clear Channel (OTCBB: CCMO).

During six-plus years at Clear Channel, Harrison took the radio chain into online streaming with iheartradio and then into cross-platform apps downloaded more than 25 million times.

That expertise combined with Van Wagner’s current interests, which include in-stadium deals across the NBA, NCAA and MLB, and kiosks, could be particularly interesting.

Pittman is investing in Clear Channel (OTCBB: CCMO) — and joining it as Chairman of Media and Entertainment Platforms. The investment is personal, not through his Pilot Group; he will continue to invest on other ventures through the PE firm.

But the real investment here is something Pittman has avoided since AOL: himself. He’s advised companies and mentored startups since leaving AOL Time Warner. At Clear Channel, though, he will take a hands-on role. It’s also a layered one, the kind that has led to trouble in other organizations and will have to be finely tuned to work here. Clear Channel Radio President and CEO John Hogan will report to a new Operating Committee of the Board “through Pittman.”

The press release from Clear Channel says this reflects the “long term strategic importance of the core radio business to the Company, and the Company’s focus on further development and execution of opportunities in the digital arena.” You would think that would be clear enough without needing Pittman or another layer but Clear Channel clearly wants to send a signal internally and externally that it’s not business as usual.

This follows the August announcement that longtime digital head Evan Harrison is leaving at the end of the year. At the time, Hogan stressed the importance of digital to Clear Channel’s growth strategy. Now the board is stressing it to him.

Update: As a reader reminded me, I should mentioned earlier that Mays also has said he is leaving at year’s end and that no successor has been announced. Bringing in Pittman covers the bases for radio at the very least, and should help keep it from transition-itis. It may also be a precursor for more changes, including Hogan’s role.

During his six years at Clear Channel Radio, Harrison was credited with building up the company’s position in online streaming, particularly with its iheartradio site; he had also talked to us this summer about the success of the company’s iheartradio mobile apps, which he said had been downloaded more than eight million times and were making money for the company.

Radio Ink cites an internal memo sent out by Clear Channel Radio CEO John Hogan, which says that Harrison “has shared his desire to pursue new challenges” and that the company is searching for a new online head.

From the memo: “Digital continues to be an essential part of our growth strategy. It is important that we continue our charge to make sure that our content, delivery modalities, technology innovations, and the monetization of digital continue to move forward as a critical priority.”

Users will download the free FLYsmart application under the guise of it offering information on nearby services in airport terminals. Geodelic’s expertise, which includes the Sherpa location-based app distributed by T-Mobile USA, will supply maps to find newsstands, gift shops, restaurants, terminal information and more. The application also includes live feeds about arrival and departure information, and extends beyond the airport to get information about nearby hotels.

A Clear Channel spokeswoman said the company wasn’t prepared to say what advertisers were participating in the app, but in a release, Ron Cooper, Clear Channel Outdoor’s CEO, said: “We

Evan Harrison, *Clear Channel* Radio