When you think of Playboy, a middle aged woman in a well tailored suit might not be the first thing that comes to mind, but for me personally the allure of Playboy has always extended beyond the romanticized lifestyle portrayed on the publications pages and into the multimedia empire’s boardroom. For more than two decades Christie Hefner, Hugh Hefner’s daughter, sat at the helm of Playboy as President and eventually CEO. Ms. Hefner wasn’t running the company in silk pajamas from a mansion in Los Angeles, that seems to be her father’s lot in life. Rather, Christie Hefner presided over the legendary magazine and its subsidiaries from a highrise in Chicago, bringing the publication into the digital age with, in retrospect, what was probably some of the best foresight in the industry.
After moving on from Playboy in 2009, these days Christie Hefner finds herself creating yet another lifestyle brand, albeit quite different from Playboy, as the Executive Chairman of Canyon Ranch, a popular resort company focusing on spa amenities as well as health and wellness. I had the pleasure of meeting Ms. Hefner in her Michigan Avenue office and was instantly in awe of her kindness, composure, and brilliance.
What did you want to be when you were growing up?
I wanted to go to Law School. Specifically, I wanted to go to Yale’s School of Law and Public Policy and I hoped to end up either in the Senate or on the Supreme Court.
What are your earliest memories of Playboy?
My mother was a reader of the magazine, so I grew up reading it along with Time, and The New Yorker, and a number of other magazines. I was a fan of the quality of the magazine from the Playboy interview to the fiction and the journalism. Then of course I visited my father at the original Playboy mansion, here in Chicago. He has always been a lover of games, and the mansion had a game room with pinball machines and some of the early video game machines, none of which required a quarter, so from a kids perspective that was about as cool as it got!
What were your initial feelings toward going to work for Playboy?
I was 22, and I intended to just be there for a short period of time. My father suggested that I come back to Chicago from Boston where I had been living and working as a journalist just to learn a bit about the company, and I think from his point of view it was an opportunity to spend some time together. My parents divorced when I was very young, so I didn’t grow up with my father. I hadn’t yet applied to graduate school, so it seemed like the equivalent of a junior year abroad. Also, I think I was interested because my interests in college had been law and journalism and from a journalist’s perspective there were a lot of great editors and writers who worked for the magazine, and from a law perspective it was a very political, very liberal culture. The Playboy foundation was active in a lot of interesting political issues and businesses that were intellectually interesting. So, I liked the people, and I liked the variety of businesses and business issues more than I ever thought I would.
Have you had a significant mentor in your career?
No. However, there was one executive at playboy who had come in before me to run Human Resources and had an organizational developmental background, and he was certainly helpful to me especially early on in suggesting different programs for me to go to and learn about marketing, policy and finance. Also, I got to know Katharine Graham, and was a great admirer of hers. I considered her a friend, but we were never close enough to characterize her as a mentor.
What do you think were the biggest misconceptions people had about a woman running Playboy?
Oh, I have no idea. I think people were fascinated and are fascinated by a woman running Playboy, and that was something I could use to my advantage to get meetings for things such as potential partnerships or speaking engagements to help the company. I think that the fact that I was young, and a woman, and second generation when I took over the company created general curiosity about me, but that mostly manifested itself as people being intrigued rather than having preconceived conceptions.
Are there any common mistakes you continuously see young women making in the workplace today?
Well I would say that in general you don’t get in life what you deserve you get what you can negotiate for, so it’s really important to be comfortable negotiating in whatever field you go into, not just if you’re in sales or law. I think the research shows that women are less apt to ask for raises, and more likely to wait to apply for promotions until they have experience in all aspects of the job, versus men, who if they match 60% of the job description feel that they can learn the rest. So the willingness to ask for a raise or a promotion is really important, for everybody, but statistically women appear less apt to. I also think it’s important for women to realize from the company or organization’s perspective that their objective is not to make you happy, their objective is to run a successful business. So the successful way to have those conversations about raises and promotions is to highlight the work you’ve done that will make your boss, division, and company more successful. This means understanding what is their metric for success, and how that changes over time. The conversation needs to be around what you can do for the organization, not why you deserve something.
What do you consider to have been your biggest accomplishment at Playboy?
I think the fact that virtually before any other media company, including much larger companies, we had an idea where the future of the industry was going and redesigned the business to be a multimedia content company rather than just a publishing company. We were the first to launch a brand of television networks, we were the first magazine to go up on the web, we were the first magazine to create mobile content, and we were really the first to, in a significant way, define ourselves as content and a brand that lived beyond our pages. We built a billion dollar licensing business around the world, and the fact that we accomplished that with far fewer resources than much bigger companies is something that all of us who worked on it are very proud of. The other thing I’m also very proud of is the team I built, and the culture that I created. I’m a big believer in the importance of creating an environment where the best people want to come and where they can do their best work.
What is the difference between Playboy and pornography?
Pornography is a word used to describe what you’re not comfortable with, so there’s no clear definition. What somebody likes is erotica and what someone is uncomfortable with is pornography. By any objective standard, given that it was a romanticized view of sexuality that was about as far from what was available in print let along video and television as explicit, I think it’s difficult to call it that unless your view is that anything that’s “sexy” is pornography which is a.) a very narrow view, and b.) not a very helpful view, since at the end of the day there’s a reason why cultures who suppress sexual imagery don’t tend to have women’s rights. Either one has a point of view that’s a humanistic point of view about human sexuality and human freedom, or you tend to be at the other end of the spectrum.
What was the most challenging thing about being in business with your father?
Well I think I was helped a lot both in that regard and in the way that people perceived me in that I didn’t come into the business expecting to stay and run it. I was not the heir apparent, which I think is a much more difficult role to fill for both women and men. My journey was much more organic in terms of that I found the work interesting, and then the company getting in trouble and my feeling that I could help, forming the office of the President, and then becoming President. So that path made things easier. Additionally, in terms of my father it was easier because he never really wanted to be the CEO of a publicly traded company, what he wanted was to have was a really great magazine that was sufficiently successful to the point he didn’t have to get another job. Even when he was the CEO he functioned more like a Chief Creative Officer than a traditional CEO. That gave us complimentary interests and spheres of influence that made it helpful. He wasn’t particularly interested in management, or operations, or hiring, or building a base of institutional investors. Lastly, candidly, I think the fact that I lived in Chicago and he lived and worked in LA gave us space.
What do you admire most about your father?
Well I’m a great admirer of just how brilliant he is as an editor and a visionary, but I admire very much his morals and his ethics. He’s loyal. He’s honorable. He once said that “you can tell the kind of person someone is when they have enough money to be an asshole”, and it’s true. Once you have that much money people will tolerate that, and yet he’s the same person and has the same friends he did when he was starting the magazine, which I rather admire.
There’s a lot of loyalty that I’ve discovered comes with having Chicago roots!
Yes, and I think that Chicago has an anti-costal, anti-cynical sensibility about it that was actually very helpful to the magazine’s early success. I think it would have been more difficult for Playboy, given it’s more upbeat, life affirming philosophy, not jaded view of the world to have prevailed on either coast.
That’s so true! Now bring us up to date- You’re currently the Executive Chairman of Canyon Ranch Enterprises, a well-known and very well respected spa and resort company. What drew you to Canyon Ranch after decades at Playboy?
Well I’ve been on their board for about a dozen years, so I got to known the founders and the company really well during those years. I developed a lot of respect for how mission driven they are. They would define their mission as giving people the tools and inspiration to lead healthier lives. and they do it in what I think is an extremely effective way in bringing together the best thinking of traditional western medicine, Doctors, and executive health programs with a real appreciation for how much of health is about lifestyle and that’s how you exercise, what you eat, and how you manage stress. Then they’re also excellent at being open to what are sometimes called eastern or nontraditional therapies, such as meditation to reduce stress or acupuncture. So I feel especially in a world where we’re trying desperately to move from what we have which is a sick-care system to what we should have which is a health care system, their ability to help companies think differently and act differently is really important. So when I left Playboy and their CEO asked me to help them work on how to take their knowledge and brand beyond the properties they manage, where people go for lengths of time, I thought it was somewhat similar to the work I’d done at Playboy because it was about media distribution and brand extension, in what I think is a very important space, which is the healthy living space, with a company that I like, and people I like, and I felt I could help them and yet it wouldn’t be so similar to what I’d done before that I’d feel like I’d seen that movie before.
I’ve read before that Obama being elected was a catalyst behind you leaving Playboy, how so?
It helped trigger what I’d been thinking about doing for some years which was leaving after a very long run at Playboy. One of the interests I had, going back to your earlier question, was politics and public policy, and while I had previously worked with candidates, including Barack, over decades, starting Emily’s List, and being a delegate to the National Democratic Convention twice, I really wanted to be more deeply involved in that, especially at a time when, knowing the incoming President, I knew that he was going to tackle the big issues. So that pushed me to say- if I don’t leave now, when? So what I’ve done is align myself with the leading progressive policy think tank which is called the Center For American Progress it’s based in DC and was started by John Podesta when he left the Clinton administration, and I’ve worked with them for the last 5 years in ways that I find very satisfying around public policy issues.
Where do you see yourself 10 years from now?
I don’t make 10 year plans, and I discourage people from doing it! I think you have no idea what’s going to happen over the next 10 years, in my opinion it’s a waste of time, and frequently causes people to do things in the meanwhile that they’re not happy doing because they think it’s getting them somewhere that it’s just not possible to know if you can get to. If you look at the Bureau of Labor Statistics a significant percentage of jobs today are jobs that didn’t even exist 10 years before. So that’s just not how I think. It’s important to be doing work that is inspiring to you, that makes you feel fully engaged. It’s important to me that I’m giving back and engaged with nonprofit organizations. It’s important to me to have time with family and friends. It’s important for me to have time to travel and pursue hobbies that I have, and to have all those things in balance, and that’s how I look at and judge whether the chapter I’m in is working for me.
What do you like to do in your free time?
I like to travel! I leave tonight for 10 days in Argentina. I try to take an interesting big trip every year. Last year I went with my brother, mother, and her husband to the Galápagos. Next year I plan on going to Myanmar. I like theater and film. I like cooking and dinner parties. I like reading. I like spending time with friends. I like sports.
Read more about Christie Hefner’s favorite things here.
[Photos By Hallie Duesenberg]