Phil Hendrie has been the de facto “Sybil” of radio for well over a decade, having concocted a bevy of characters to debate — as well as enrage — unknowing passerby listeners on the issues of the day. He has tailored his syndicated show since then; now he solely debates his characters in the studio as well as on the phone. Yet what makes Hendrie a Power Player of sorts is that he has segued his craft into the digital world where, for example, he has concocted his own professional football league … and one of his characters, the suburban housewife-from-Hell-in-vain, Bobbie Dooley, has her own celebrity interview podcast. Here’s how Hendrie is exploiting his talent in the digital world to his optimal gain.

You were one of the “early adaptors,” of sorts, of air personalities who really took advantage of using your website and other digital avenues to generate revenue. Exactly when did you realize digital’s potential?

The website was an adjunct of my radio show as early as 1999; it was a subscription site from ’99 on. I got ownership of the site in the fall of 2006; it continues today as a subscription site basically because that was immediate revenue generated by my radio show. After I left Clear Channel, we controlled the material so it was obviously something we could build on.

We started to think about creativity in a new medium. The other thing is you start talking to other people in similar businesses to find out what they’re doing and vice versa. We added a videocast, started streaming exclusive content to subscribers and so forth.

But I don’t think I ever thought of myself as an early proponent of the digital arena. I just saw myself as a guy who needed to keep an income stream going at the same time I did my on-air show, to continue to generate money regardless of whether the show was live on a network.

Were you disgruntled with the way your corporate radio employers looked at the digital world, which prompted you to go out on your own?

I wouldn’t call it “disgruntled.” It was more a desire, on my part, to take a more active hand in promoting my show — not just in creating it and performing, but in producing it and getting it out to some areas that weren’t being exploited 100%. I don’t think it’s any secret that radio has been a little slow in coming to terms with the potential of digital and the Internet – for a lot of reasons. We, on the performing and producing side, saw it as a new entrepreneurial outlet for our efforts.

Did you change your on-air show to better accommodate your website and digital efforts?

The radio show is pretty much the same; any changes have come from what we had outside of the radio show. We now do videocasts, a 45-minute pre-show … and sometimes we create whole new podcasts. We “cover” a fictitious football team, The Milwaukee Lions – literally an entire team that competes in its own league. It’s all a satire, but we play it like it’s real. The Phil Hendrie Show becomes its own reality. Sometimes we create exclusive broadcasts, such as one weekend, we did a videocast of me doing shots of tequila. That helps us create and build an audience that goes beyond our radio show.

We’re also excited about making our media available to iPhone and iPad, using an iOS stream that takes our videocasts and our audio global — literally live and mobile – through iPhones, Androids and iPads. Whether we do the show live or something on-demand, having that content available on those devices expands our ability to reach a bigger audience.

Many radio air personalities had to tailor what they did on-air to suit a medium that was now monitored by the PPM instead of a diary. (i.e.: less talk or more succinct bits) Did you feel any inclination to change the way you did your show because of the new ratings monitoring system?

Well, to be honest, the only actual income stream I have is from my efforts in the digital world — subscriptions to my website, acting, voiceover and things like that. The radio show’s sales support has generated no income and hasn’t for years. So, at present, there’s simply no incentive to learn anything about PPM. Why? My time is better spent interacting with the guys at Launchpad Media or LEG who are involved in ad sales on the digital side and strategizing with them.

Recently you announced that you’re launching a podcast series of celebrity interviews conducted by Bobbie Dooley, who is one of your regular “characters.” Exactly how will this work?

It’s a live interview segment of me in the character of Bobbie Dooley, who’ll be talking to a variety of celebrities. Bobbie is your typical sociopath housewife who’s a homeowners association president, 39 years old going on 19 … she has three sons she dotes on, but doesn’t realize they’re into the Aryan Brotherhood … her husband, who also dotes on her, is sexually promiscuous … she’s a clueless, emotion-less person who’ll be interviewing the likes of Patricia Arquette, Joel McHale, Sugar Ray Leonard, Kevin Pollack and Jay Mohr. They’re all great performers and actors themselves, and they’ll do a great job at improvising with Bobbie.

But why Bobbie? Why not Ted Bell, Margaret Gray, R.C. Collins or even David G. Hall?

I thought long and hard about this, and I did consider Ted and Margaret, but I think Bobbie is the most fully realized character I do. For the purpose of this podcast, she’s perfect. As a stay-at-home mother and wife, she spends more time consuming the entertainment pages of tabloids, websites like TMZ and TV shows. On top of that, even though she’s fascinated with the notion of celebrity, she sees herself as the centerpiece of it. As depressed and as emotionless as she may be, she still sees herself as the star in the room – and that’s where this show will get its power. The guests could be Richard Burton and Elizabeth Taylor, yet Bobbie would think she was the most interesting person there.

If I did a poll right now of my audience on who my most popular character is, say I held this poll on Facebook, I’m sure Bobbie would win. Even now, she has the most Twitter followers. We felt that, right after we did our second podcast, we wanted go with her for her own interview series. We even had great artwork that perfectly visualizes her look — very California, extremely current, a 21st century unicorn … seemingly interested in the world but in fact extremely narcissistic

Before starting this podcast, you did change the show, dropping real-life callers to take it “in-house,” with Margaret Grey, Bud Dickman and Robert Leonard acting as co-hosts Why the change?

You’ve got to evolve whatever you’re doing – especially if it’s an entertainment product. You really can’t keep the show the same and rely on it to continually deliver. You always have to evolve your craft – at least in my world, you do. In this case, I felt the show lacked a more dimensional Phil Hendrie. I needed to be in the show more; I needed to have more of my personality and feelings expressed, instead of having the characters do it. So I thought I’d bring some of the characters into the studio as co-hosts — which, ironically, was what I originally envisioned doing – as a sort of a morning zoo, only where I would serve as my co-hosts, so I could better control what they do with me. This way, when I think it would be cool for a co-host to say this, I wouldn’t have to ask anyone to do that – I’d do it as them.

I’ve got to be honest with you; it’s still a work in progress. But I used to be afraid to listen to airchecks of my show because while some bits were great and some shows were fantastic, there were some nights that I know didn’t work out right, and I didn’t want to listen to them. But the show I’m doing now, I have no problem listening to it every single solitary night. You know how everybody judges their success as to how consistently they enjoy their job? In that light, my show is at its most successful point today than it has been in years.

Are there any plans on switching character co-hosts?

It depends on how well it continues to work out. There are technical things that have to be worked out in terms of how well the character plays when you put a studio mic on his or her voice. The studio doesn’t have the same ambience as when that character is talking over a phone. Can you maintain the illusion of there being separate people in studio? Can you differentiate this voice over that voice? For instance, Margaret is relatively easy for me to do, as is Bud and Robert. RC is very distinctive, too, but Ted Bell sounds essentially like me, only he’s talking through an overbite and he speaks in a more pronounced way. I think it would be difficult to make him as distinctive in the studio as I can through a telephone, where the voice is filtered.

Back when you did take outside callers, were you ever concerned that you’d enrage one over the edge? I refer to Ted Bell’s Diorama bit, where as curator for a child’s museum, Ted wanted to have deceased children used as props in historical Dioramas. An elderly woman called in and said one of her grandkids died at a young age, and a nonplussed Ted asked if the kid was disfigured or had facial scars, because if he didn’t, Ted could use him as the baby Jesus in a Nativity scene. The way the woman moaned, “No! No!” … I swore she was going to have a stroke. Were you ever concerned about taking it too far?

No, because when you’re talking about a call-in show, you’re talking about people who literally and willingly picked up the phone and called … and in this case shared extremely sensitive and traumatic information — all by her own volition. She was not forced at gunpoint to talk about her dead grandson. She mentioned that voluntarily. I’ll go even one step further. Not only do people like her call up and share that kind of information, they’re doing it for a reason – to manipulate the radio show.

Let’s put this in context: Talk show callers are a very small percentage of the listening audience. They call in for two reasons: 1) to get approval of the host, usually through the force of debate; or 2) they want to control the content. In this case, one of the best ways to control content is to talk about your dead grandkid as if it’s a dead dog or something. We see those people coming.

It’s not that this elderly woman is doing this maliciously, but by sharing this information, it can do one of two things: 1) make the host retreat and say, “I’m really sorry … I would never think that would be funny on the radio” – after which I might as well go back to a job as a garbage man, or 2) I could stay in character and ask if the kid’s disfigured, and as the host, I could defend the caller and make Ted look like more than an asshole than he already is.

When you added videocasts of your performance, were you at all worried about losing the “theatre of the mind’ component of your show?

I stopped worrying about “theater of the mind” years ago, back when radio stations put glass in the studio, so anyone who walked by could see what the DJ was doing. The radio industry doesn’t do all that much to protect that illusion anymore. By now, I think it can be fascinating work on radio today; people love to see the curtain pulled back to see how it works – and my show can be extremely interesting. You’re watching a borderline madman going in and out of character. The videocast enables listeners to see me behind the scenes, during not just my good days but my bad days, when I’m frustrated with how the particular show is going. Want to maintain that theatre of the mind? Don’t watch the videocast, and or just look away.

The videocast aspect almost turns your show into a reality show of sorts…

You can’t look at us on video and compare us with reality shows on TV today, because TV reality shows are simply non-professional actors improvising scenes they are given by a director, based upon their lives. It’s just bad improvisation. People pick up on that and sense that they’re not looking really at reality – but it doesn’t matter that it’s not. In my videocasts, you see literally what a radio personality goes through to create a radio show. It may be that I’m not having a very good day, or a very good marriage, or I could I walk in there and vent about the industry itself. The days that I am pissed are as genuine as the days I am happy or sad. Whatever comes through, the most I can offer my audience is a completely honest day.

You mention that you’re pretty content with the way the show is running right now. Considering that, do you feel obligated to still push the envelope, or can you be content with the good times as they are?

You always want to push it and try new things – and I always want to do that. I guess what I meant say earlier is that I’m happy now in that I’m consistently putting out a good show; I can listen to my podcasts and laugh and be proud of them. Will they and the show change? Yes, they’ll eventually have to – and I’m going to welcome it. There will be a time when I get bored doing the show this way, so I’ll do it another way. I’m just hoping that through it all, the audience comes with me, because no matter the change, I’ll always be the same Phil Hendrie.

At this moment, you have a syndicated radio show, a website that produces original content as well as show archives; you do voice work for characters in TV shows, and as This Is 40 illustrates, you branched out into film acting. That’s a lot of plates spinning simultaneously. How do you plan to keep spinning so many in the future?

It is a lot of stuff. Fortunately for me, the more you do, the more people you have to support you. I have Amir Forester, a great publicist; my son Alex works with me; I have a great digital partner in LEG Entertainment, who are also helping me produce other projects for the future – and I’ve got a good day planner.

I’ve also lost 90 pounds, so I’m keeping myself more physically fit. I started that almost a year ago, and losing all that weight is enough to inject an extra 50% of energy in me. I’m really fortunate that I’ve got really cool people to help and support me … and with them behind me, I’m able to do lot of things that I can keep doing for a very long time.