Q&A with Scott Flanders, the Hoosier CEO of Playboy

Given the Hoosier reputation for modesty, you’re an unusual candidate for CEO of Playboy. What was your upbringing like?

My parents were members of the Chapel Rock Christian Church on the west side, which is about as close to Southern Baptist as you can get. Extremely conservative. I’m quite confident my parents never voted for a Democrat. Of course, that made it inevitable that I would end up as CEO of Playboy. [Laughs.] Actually, it was an environment not that different than the one Hef grew up in a generation earlier in Chicago.

The coming rebranding of Playboy comes after decades of declining subscriptions. At what point did the magazine lose its way?

Hef has been the editor-in-chief of the magazine since the beginning. And it’s my belief that over time, he became less connected with the young urban male, which is our target demographic. That’s inevitable with age and changing preferences for how young people spend their time.

After taking the job, how quickly did you realize that the magazine needed a reboot?

I took the job in 2009, and I quickly saw the company needed a cultural reboot. But getting rid of nudity was not initially a strategy. At the time, I believed it was part of the DNA of the brand. We took the company private in 2011, and did a lot of research. We launched our social media around that time, and saw exponential growth on Facebook, Instagram, and Twitter. We’re now at 30 million social media followers. That led us to believe our brand could participate on platforms that don’t allow nudity. I’m not claiming to be a visionary. The best leaders follow their customers. Our audience was demonstrating that they were attracted to our non-nude lifestyle content. So we went to the board in the fall of 2013, and said we should relaunch Playboy.com as a safe-for-work, mainstream website. Our advertisers want to reach that young, male audience, which is hard to find—they play so many video games and they don’t watch a lot of linear television. When we relaunched the website in 2014, we were seeing about 1 million visitors a month. We’re now at 12 million. By January 2015, the enormous success of the website had me thinking we should align the brand entirely around this non-nude strategy.

What was Hugh Hefner’s reaction when you approached him with this suggestion? I imagine he wasn’t crazy about it.

I expected some resistance from Hef. So I had the consultants deliver the findings to him and the board, and I stayed home in a bomb shelter. I waited for the call. They showed him imagery of what the magazine could look like, and he deferred. He said “If this is what the millennial audience prefers, that’s what we should deliver.” I was shocked. I knew Hef would get there eventually because he’s smart, but I didn’t think he’d get there in one meeting.

What will the new magazine look like?

It’s still going to be sexy and provocative. But it’s now targeted to millennial males. We’re comfortable with the fact that we’ll lose some of our older subscribers. I’m no longer the audience, but I still aspire to be connected to that demographic. No one wants to go to a restaurant full of 60 year olds—even 60 year olds. The key things will be retained: the playmates, the interview. We’re going to add an artist in residence. One of my favorite new features is called My Way. It will be a profile of a person who has decided to exit the scene. This is the big fantasy of millenials—to give the middle finger to the Man. We’re going to profile that moment when someone is driving to work on I-465 and decides to drive home and make surf boards for a living. That’s who Hef was as a young man.

What’s something I don’t know about Hef?

When he lived in Chicago, he was offered a job at Esquire. He asked for $5 more a week than they were offering, and they wouldn’t give it to him. So he decided to go it alone and launch Playboy. A few years later, the editor of Esquire sent him a $5 bill and said it was the biggest mistake he ever made.

Will Esquire be one of your primary competitors now that Playboy is non-nude?

No, if you look at our social media audience compared with Esquire’s, we’re so many times bigger. Esquire is written for an older man. This is going to be decidedly younger. Our competition is Vice, Buzzfeed, Vox Media—these sites that reach tons of millennial males. The next step for us is taking on those. Disney just invested another $200 million in Vice and they have a $4 billion valuation.

How often do you get back to Indy and what’s your impression of it today?

When I was growing up in the 1970s, we always considered Indianapolis a suburb of Chicago. But it has definitely become its own city today. My wife and I get back at least once a year for a Colts game. The restaurant scene is astounding. It feels like L.A. We love the Meridian—major metro quality food. And then our friends take us to the newer places like Tinker Street. The state had a setback with the RFRA. That had to be the biggest bone-headed move in the history of Indiana PR. But setting that aside, the place has a pretty good reputation for being business friendly.

You mentioned your wife. What did she think about you taking a job that involves spending so much time with beautiful women in scant clothing?

Actually, my wife was the decisive influence in getting me to take this job. There are times I wonder if she had an ulterior motive. Was she trying to outsource me to someone else? [Laughs.] I was CEO of a newspaper and TV company at the time, and she didn’t find it all that interesting. When I was offered the Playboy job, we went to dinner, and she said I should take it. She thought it would be fun. I thought to myself, If you have a wife who wants you to go be CEO of Playboy, you should probably do it.