Diane Silberstein, Former Playboy Publisher, To Samir “Mr. Magazine™” Husni: “This Is A Time For Reinvention.”

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The Mr. Magazine™ Interview…

“I am very privileged. I’ve worked with some amazing people in my career, and it’s not over yet. I’ve met some incredible people… I’ve worked with some of the most incredible marketers around, people at agencies and on the client’s side. And my colleagues that have never failed to impress and inspire me. And we just keep going. This is a time of reinvention, that’s for sure.” … Diane Silberstein

Playboy is folding the print component of its iconic brand, citing the Coronavirus as the reason. A victim of the pandemic and its tragic hold on the world as a whole right now? Some may believe that, but as for me personally, I don’t think so. I believe the brand as a whole, and not just the magazine, lost its relevance long before Hefner’s death or the Me Too movement.  But rather than lead with my assumptions, I decided to go to an insider who has been at the helm of Playboy and ask her opinion.

Diane Silberstein is no novice when it comes to the world of magazines. From launching Allure to  being at Elle and The New Yorker, combined with her days at Playboy and Opera News, she is a woman who knows her way around magazines and publishing. And when it comes to Playboy and being the first female publisher at the gentlemen’s magazine, well, she is definitely a groundbreaker.

I spoke with Diane recently about her illustrious career in publishing and all of those wonderful brands she worked on. It was a delightful conversation and one where she agreed that Playboy was Hugh Hefner and Hef was Playboy: “Mr. Hefner was a big part of the brand. I wish that Playboy had continued on building the brand in a way that evolved it for the next generation.” The idea of being a part of a brand that was at one time untouchable in circulation when it came to men’s magazines, makes Diane an inimitable part of magazines and magazine publishing.

So, I hope that you enjoy this informative interview with a woman who has had a magnificent career in the past and has no intention of slowing down when it comes to the future. Once this pandemic has passed, and she firmly believes it will, the time for reinvention is at hand. For magazine brands and their publishing mantras. And now the Mr. Magazine™ interview with Diane Silberstein, former publisher, Playboy.

But first the sound-bites:

On being a former publisher of Playboy and her reaction to the news that the print magazine was closing up shop: My first emotions were very sad, another iconic brand shuttering its doors. I had the same reaction when I heard that Glamour magazine was suspending publication, which is the first place I worked; it was my first job out of college. But here was an iconic brand that meant so much to such a great number of men. The circulation was three million when I was there. I was there in 2003, 2004, and 2005. So, that’s going back a number of years, but with a circulation of three million, the readership was up to almost seven million. We reached a lot of men in America. So it was just heartbreaking to hear that it was going away.

On whether she feels the reason the magazine didn’t make it was because Hefner was no longer there: I think Mr. Hefner was a big part of the brand. I wish that Playboy had continued on building the brand in a way that evolved it for the next generation. During the early 2000s, Playboy was battling against Maxim, which was a huge brand at the time as well for young men. And I don’t think there’s been another brand that has taken over and stepped into the role to really capture the attention of young men today.

On whether she was comfortable showing the photography to the ad community considering she was a female publisher for Playboy: It was very comfortable for me to talk about the magazine and it was very comfortable to be in a presentation, and especially talk to other women who were buying media, about the magazine and explain the mindset of women talking about Playboy, and marketing Playboy, with it being the magazine that was entertainment for men.

On the transition of going from working at Elle and fashion to Playboy and skin: You’re not necessarily working with solely the editorial content, you’re really working as a publisher with an audience, and that’s what you’re marketing. So, at Elle, we were really marketing an audience of women who were interested in fashion and beauty. At Playboy we were marketing an audience of men, red-blooded American men, who were interested not just in women, but who were also interested in cars and electronics and in looking good and grooming. And that was the audience that we were marketing.

On Diane Silberstein the publisher and the difference between working for a nonprofit and a profit publication: My publisher self and my experience in sales and marketing stays with me and continues with me now into my career in real estate. I think the differences between not-for-profit and profit is everything looks at the bottom line for profitability. In my own experience in the nonprofit world, I found change to be slow in spending and very challenging, because the approval process is many layered between management and reporting to a board that has varying points of view. So, it just takes much longer to get things accomplished. And to me that’s the biggest difference.

On some of the highlights of her career: When I look back on the whole of my career, one of the highlights that stands out in my mind is launching Allure magazine, because rarely do you have the privilege of working for a man like S.I. Newhouse. And being able to launch a magazine where you have incredible resources at your disposal and the top talent that’s in the business, and the ability to create something from the ground up. And probably the most interesting as a highlight was certainly working at Playboy, because it was so varied and it was the first time I had ever worked for a public company, so it involved quarterly reporting; it was a different set of skills that were needed and I was able to work with so many different areas.

On whether visiting the Playboy mansion was ever part of an advertising coup: (Laughs) Every client wanted to go to the mansion, but no, that wasn’t a prerequisite for signing, not at all. But a lot of clients did use the mansion for events and programs, and we certainly allowed that. But no, that was not a carrot for clients. Not at all.

 On what Hefner was like as a boss: Well, I reported to Christie Hefner who was CEO of the company, I did not report to Hef. I think to get more in depth knowledge that probably came from Jim Kaminsky, who was editorial director during my term there. But Mr. Hefner, from my observations, did make the final call on everything.

On the advice she would give someone today (after the tragic pandemic is behind us) who wanted to launch a new magazine in this digital age: I think you have to be really honed in on a niche topic. And you have to build your audience really from the ground up. It has to happen organically and it’s a tough thing to do today. I wouldn’t advise anyone to do it, especially if they’re investing their own capital in it. It’s a very difficult time for all media brands and everybody is struggling for support. And when I say support, I mean marketing and advertising support.

On her vision of the future of the printed magazine: I think it’s obvious that the migration to online and how we consume media is in a digital world going forward.

On how she proposes people can make money from digital media: With digital media, you’re either charging the consumer for exclusive content or you’re very specifically charging for your audience that you can target and micro-target.

On whether anyone today can replicate her own footsteps in the marketplace or advertising world or those were the good old days: I hate to discourage anyone from going into the business today, because obviously we need journalists and people to report on what’s happening today in the industry. So, I would say if your passion is writing, definitely do it. But there is a new way in which we do business. My friends who are still in the industry on the business side, they are all stretched so thin because they’re not doing single titles anymore, they’re working on multiple titles, everything has been condensed. We do talk about the fun that it used to be. It was such a great business, both from the client side and our side as media sellers. It was fun and it was great, money was free flowing because advertisers only had the choice of print media or television to get their eyeballs. That was it. Business wasn’t as fractured.

On any other career highlights she’d like to mention: Other highlights that were very challenging for me; my time at Ziff Davis Media, Yahoo! Internet Life magazine, which was back in 2001 and 2002, I was there as publisher at 9/11 and right after 9/11, Ziff Davis Media closed its entire consumer magazine division and that included Expedia Travels, Yahoo! Internet Life, and a small magazine called Family Internet Life. And there was no advertising. Certainly nothing in the travel industry, because no one was traveling after 9/11.

On being the first female publisher of Playboy magazine: It was an amazing time to be there. It really was. And Christie (Hefner) was my role model because I was on the fence about working there, but she was so smart, she pointed out to me that many of the writers who wrote for The New Yorker also wrote for Playboy. I took home two years’ worth of the magazine and read them. My whole background had been basically marketing to women and here was my opportunity to market to men on a very grand scale. And it just made sense. And to be able to work for a public company, which was a big draw.

On the biggest misconception she thinks people have about her: I think the biggest misconception people have about me is that I don’t eat junk food, (Laughs) I’ve always been pretty much the same size. But I have a wicked sweet tooth and a weakness for ice cream. And I’ll never turn down pizza.

On what keeps her up at night: What really keeps me up is what will happen to this country should Trump be reelected. And I’m very worried about the Coronavirus, but I feel that this too shall pass if everyone will stay in and stay home. But I’m worried about longer-term when it comes to what’s going to happen in this country.

And now the lightly edited Mr. Magazine™ interview with Diane Silberstein, former publisher, Playboy.

Samir Husni: Amidst the horrible reports of Covid-19 all over the world came the news that Playboy has decided to stop its print edition. As a former publisher of Playboy magazine, were you surprised by that decision? What were your first emotions when you heard the news?

Diane Silberstein: My first emotions were very sad, another iconic brand shuttering its doors. I had the same reaction when I heard that Glamour magazine was suspending publication, which is the first place I worked; it was my first job out of college. But here was an iconic brand that meant so much to such a great number of men. The circulation was three million when I was there. I was there in 2003, 2004, and 2005. So, that’s going back a number of years, but with a circulation of three million, the readership was up to almost seven million. We reached a lot of men in America. So it was just heartbreaking to hear that it was going away.

Samir Husni: Did you ever have the feeling that without Hefner being there the magazine wouldn’t make it, as though he and the brand were one in the same?

Diane Silberstein: I think Mr. Hefner was a big part of the brand. I wish that Playboy had continued on building the brand in a way that evolved it for the next generation. During the early 2000s, Playboy was battling against Maxim, which was a huge brand at the time as well for young men. And I don’t think there’s been another brand that has taken over and stepped into the role to really capture the attention of young men today.

What are young men looking at? I feel like I have almost a focus group here between my own sons and their friends. What do they look at and what do they read? They’re not really consuming media, lest it’s a complete vertical. They’re not consuming general interest media, unless it’s online. And I think addressing young men, you really had to morph brands online much quicker and include much more content. They all talk about Thrillist, they all look at Thrillest. And then they go vertical; they go into the sports; they follow food; they listen to podcasts; they all follow their entertainment online, but there’s not a general interest option. And Playboy was general interest, but Playboy was a little bit too risqué for general interest tastes. It didn’t follow the times; it needed to adjust itself and take the nudity out of the magazine to be much more politically correct. Certainly in today’s times with everything that we’re going through with the “Me Too” movement.

Samir Husni: Steve Cohn said to me that you once told him that being a female publisher at Playboy was to your advantage because you were more comfortable showing the pictures, the photography, to the ad community than your male sales people were.

Diane Silberstein: Yes, that’s true. It was very comfortable for me to talk about the magazine and it was very comfortable to be in a presentation, and especially talk to other women who were buying media, about the magazine and explain the mindset of women talking about Playboy, and marketing Playboy, with it being the magazine that was entertainment for men.

Samir Husni: You’ve been at Elle, The New Yorker; you’ve worked with Tom Florio and Tina Brown, you’ve been there. How was the transition going from working with Elle and fashion, to Playboy and skin?

Diane Silberstein: You’re not necessarily working with solely the editorial content, you’re really working as a publisher with an audience, and that’s what you’re marketing. So, at Elle, we were really marketing an audience of women who were interested in fashion and beauty. At Playboy we were marketing an audience of men, red-blooded American men, who were interested not just in women, but who were also interested in cars and electronics and in looking good and grooming. And that was the audience that we were marketing.

Samir Husni: The last time you and I talked, you were the publisher of Opera News and I asked you if there was a difference between being a publisher for a not-for-profit and for a profit publication. And you told me that once a publisher, always a publisher. Tell me more about Diane, the publisher. I know you’re in real estate now, but you were in publishing for years. Tell me about that time.

Diane Silberstein: My publisher self and my experience in sales and marketing stays with me and continues with me now into my career in real estate. I think the differences between not-for-profit and profit is everything looks at the bottom line for profitability. In my own experience in the nonprofit world, I found change to be slow in spending and very challenging, because the approval process is many layered between management and reporting to a board that has varying points of view. So, it just takes much longer to get things accomplished. And to me that’s the biggest difference.

And wearing a publisher hat is really the managerial and executive skills that I take now into my own business; I’m my own boss now. And how I run my business are the same marketing skills and the same bottom line skills, I’m running a P & L for my business. And the same people skills that I use now in meeting people every single day. Each person is a new client and it’s a new adventure. It’s wonderful.

Samir Husni: If you were going to tell me three highlights of your career so far, what would they be?

Diane Silberstein: It’s very hard to edit it down to three highlights, but when I look back on the whole of my career, one of the highlights that stands out in my mind is launching Allure magazine, because rarely do you have the privilege of working for a man like S.I. Newhouse. And being able to launch a magazine where you have incredible resources at your disposal and the top talent that’s in the business, and the ability to create something from the ground up.

The idea of launching Allure was very controversial at the time because the industry said who needs another magazine about beauty, but it was a different approach and it was the new face of beauty, but there were a lot of naysayers. It was a very tenacious group of people and staff that we hired to get it off the ground. It was so much fun; it was hard work, but it was so much fun and we were all in it together.

When you hire a staff and you pick people and you put them together, it’s such a cohesive bunch when you’re working together on a launch, there’s really nothing like it when you’re creating something from the ground up. So, I would have to say that’s one of the highlights of my career.

Certainly, working at Elle magazine was another highlight, because being publisher at Elle, at the time Elle was in the third place position after Vogue and Harper’s Bazaar, and we were able to rebuild Elle into the number two position behind Vogue. That took a lot of hard work, and again it was the team there and they were amazing.

And probably the most interesting as a highlight was certainly working at Playboy, because it was so varied and it was the first time I had ever worked for a public company, so it involved quarterly reporting; it was a different set of skills that were needed and I was able to work with so many different areas. I worked with the group that did international licensing, I worked with product licensing; I was able to work with our dotcom team, somewhat with the entertainment division. The brand had so many different legs that it just made the job so much more interesting.

 Samir Husni: One of your colleagues said that the reason advertising flourished at Playboy during some stages of the magazine’s lifespan was that before some signed the deal they wanted a visit to the mansion. Did you get a lot of requests to visit the mansion before you closed a deal with clients?

Diane Silberstein: (Laughs) Every client wanted to go to the mansion, but no, that wasn’t a prerequisite for signing, not at all. But a lot of clients did use the mansion for events and programs, and we certainly allowed that. But no, that was not a carrot for clients. Not at all.

Samir Husni: What was your experience with Hefner? I had heard he was somewhat of a control freak, but in your view what was he like as a boss?

Diane Silberstein: Well, I reported to Christie Hefner who was CEO of the company, I did not report to Hef. I think to get more in depth knowledge that probably came from Jim Kaminsky, who was editorial director during my term there. But Mr. Hefner, from my observations, did make the final call on everything.

Samir Husni: Was he involved with the advertising at all, as he was with the editorial?

Diane Silberstein: No, he wasn’t involved in the advertising.

Samir Husni: What advice would you give someone today, after this tragic pandemic is behind us, on launching a new magazine in today’s digital age?

Diane Silberstein: I think you have to be really honed in on a niche topic. And you have to build your audience really from the ground up. It has to happen organically and it’s a tough thing to do today. I wouldn’t advise anyone to do it, especially if they’re investing their own capital in it. It’s a very difficult time for all media brands and everybody is struggling for support. And when I say support, I mean marketing and advertising support.

Samir Husni: Can you envision a future without print magazines and being only online? What is your vision of the future of the industry?

Diane Silberstein: I think it’s obvious that the migration to online and how we consume media is in a digital world going forward.

Samir Husni: And how do you propose people can make money from digital media?

Diane Silberstein: With digital media, you’re either charging the consumer for exclusive content or you’re very specifically charging for your audience that you can target and micro-target.

Samir Husni: Can anyone replicate your steps in today’s marketplace or those were the days?

Diane Silberstein: I hate to discourage anyone from going into the business today, because obviously we need journalists and people to report on what’s happening today in the industry. So, I would say if your passion is writing, definitely do it. But there is a new way in which we do business.

My friends who are still in the industry on the business side, they are all stretched so thin because they’re not doing single titles anymore, they’re working on multiple titles, everything has been condensed. We do talk about the fun that it used to be. It was such a great business, both from the client side and our side as media sellers. It was fun and it was great, money was free flowing because advertisers only had the choice of print media or television to get their eyeballs. That was it. Business wasn’t as fractured.

When digital was introduced, and I was there at the early beginning with Phase 2 Media, it was the wild, wild west in 1999 and 2000, because no one knew what the Internet would become or how to advertise on it; how would they reach people? And no one knew that ecommerce would become such a big part of how we live, especially today. With how we’re living today, thank God for ecommerce because we can sit home and we can order electronics and no one has to go out and shop. You can have anything delivered to your doorstep. It’s wonderful and keeps you from feeling isolated. But no one ever thought that 15 or 20 years ago.

It was just a very different way in which we all lived. The way we entertained clients; the way we went out; the events; the way we had sales meetings. You tell these stories and the young people in the business today scratch their heads. You did what? You took your whole staff to Puerto Rico for a sales meeting? I can’t believe you did that. (Laughs) Those are the days that will probably never repeat themselves, that’s for sure.

Samir Husni: Any other highlights from your career that you’d like to add or mention that we haven’t talked about?

Diane Silberstein: Other highlights that were very challenging for me; my time at Ziff Davis Media, Yahoo! Internet Life magazine, which was back in 2001 and 2002, I was there as publisher at 9/11 and right after 9/11, Ziff Davis Media closed its entire consumer magazine division and that included Expedia Travels, Yahoo! Internet Life, and a small magazine called Family Internet Life. And there was no advertising. Certainly nothing in the travel industry, because no one was traveling after 9/11.

This was in September, so Yahoo! Internet Life was about to close its holiday issue, which was all about electronics and gadgets and gear. No one was advertising so we had no revenue streams coming in, everyone pulled their marketing and media budget. And finally Ziff Davis just said they couldn’t support it; they couldn’t go forward. I think we published two or three more issues and then they pulled the plug. We had to tell the staff that the magazine was closing. We didn’t even own the title of Yahoo! Internet Life; Ziff Davis’s contract said that it was licensed with Yahoo and it said that if they made any changes that Yahoo got the title back, they weren’t even able to retain the Yahoo title.

The hardest thing was facing an entire room of people and thinking my first job now as publisher is to help everybody get a new job. And I did. I called everybody I knew in publishing and everyone had a new job within two and a half weeks. Then I thought, what am I going to do. (Laughs) So, I started talking to people and that’s when I ended up at Playboy.

Samir Husni: I remember that was groundbreaking. You were the first female publisher of Playboy magazine.

Diane Silberstein: It was an amazing time to be there. It really was. And Christie was my role model because I was on the fence about working there, but she was so smart, she pointed out to me that many of the writers who wrote for The New Yorker also wrote for Playboy. I took home two years’ worth of the magazine and read them. My whole background had been basically marketing to women and here was my opportunity to market to men on a very grand scale. And it just made sense. And to be able to work for a public company, which was a big draw.

Samir Husni: What do you think is the biggest misconception people have about you?

Diane Silberstein: I think the biggest misconception people have about me is that I don’t eat junk food, (Laughs) I’ve always been pretty much the same size. But I have a wicked sweet tooth and a weakness for ice cream. And I’ll never turn down pizza.

Samir Husni: My typical last question; what keeps you up at night?

Diane Silberstein: That’s a loaded question. What really keeps me up is what will happen to this country should Trump be reelected. And I’m very worried about the Coronavirus, but I feel that this too shall pass if everyone will stay in and stay home. But I’m worried about longer-term when it comes to what’s going to happen in this country.

But overall, I am very privileged. I’ve worked with some amazing people in my career, and it’s not over yet. I’ve met some incredible people, including yourself and Steve Cohn. I’ve worked with some of the most incredible marketers around, people at agencies and on the client’s side. And my colleagues that have never failed to impress and inspire me. And we just keep going. This is a time of reinvention, that’s for sure.

Samir Husni: Thank you.