Clear Channel Entertainment CEO Bob Pittman, speaking today at IAB’s Annual Leadership Meeting in Palm Desert, said that radio has been able to leverage its undiminished strength with digital providing a new channel and new listeners for the medium.

Pittman, a legendary industry figure who was one of the early leaders at MTV and then a leader at Six Flags over America, Century 21, AOL and Time Warner (and a BIA/Kelsey keynoter at ILM 2011), noted that “digital was the obvious way to go” for reinforcing Clear Channel’s value when he took the company’s helm a few years ago. “My entire career since the early 1970s has been about trying to find new ways to connect to the home,” he said. “But now we have reversed it,” with the latest trends — driven by mobile — about doubling or even tripling out-of-home usage.

While digital is a great enabler, it is still not the centerpiece of marketing, Pittman stressed. “You want a product strategy.” With Clear Channel, his team has built out “I Heart Radio” with an annual, in person concert that leverages the company’s relationships with on air talent and musical artists. The concert is now the anchor of the company’s marketing, and has helped raise awareness of the digital channel to 70 percent (along with what Pittman described as millions of dollars worth of on air advertising).

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At opposite corners of the niche universe, you have Thrillist for men and Comcast-owned Daily Candy for women. Both lifestyle products, founded as email newsletters/shopping guides, have jumped aboard the deals bandwagon, working with Group Commerce Inc. as their tech provider. They also have a common association with former AOL Time Warner President (and current Clear Channel Entertainment Chairman) Bob Pittman, who has invested widely in the interactive local media space.

Thrillist has moved in additional directions. A year and a half ago, it bet big on trendy clothing for its core, male demographic. It acquired Jackthreads, a members-only Gilt-like clothing company for guys, which is promoted throughout the site. Jackthreads now represents more than half the company’s $40 million annual revenues. Deals are also major contributors to overall revenues.

Mike Rothman, GM of Thrillist Rewards, told us the combination of the events newsletter, the deals and the clothing site has reinforced and pushed up the five-and-a-half-year-old site’s broad appeal. Now, the core site has grown to more than 3 million subscribers and 2.5 million unique visitors. The Jackthreads site has 1.2 million unique visitors. The Thrillist Rewards deals platform separately has 650,000 subscribers. The Rewards deals are especially curated for the readers, who average 30 years old (think beer).

“The audience was being underserved,” says Rothman. The site had 19 local editions but was mostly being sold to advertisers on a national basis. Now the site is bent on developing local sales — pushing especially hard on deals. It currently has sales teams set up in New York, Los Angeles and San Francisco, and will add “a couple more” markets later this year. The site will get additional volume via syndication of its deals that it has with marketers such as New York Magazine.

Clear Channel’s Bob Pittman and Thrillist’s Mike Rothman are both appearing at BIA//Kelsey’s ILM West Dec. 12-14 in San Francisco.

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