Robin Wolaner is CEO and founder of Tee Bee Dee, an online community for people over 40. She’s had a very successful career in publishing starting with a part-time job at Penthouse magazine and later as founder of Parenting magazine which she sold to Time-Warner. There she launched Vibe and Martha Stewart Living.
In the second of our two-part interview, publishing expert Robin Wolaner discusses her favorite jobs, the common stereotypes of entrepreneurs and the importance of learning from your mistakes.
“Just because somebody doesn’t fit the stereotype of what an entrepreneur looks like, it doesn’t mean they wouldn’t be good at it.”
Read the full interview:
Avocationist: You also wrote a book, Naked in the Boardroom: A CEO Bares Her Secrets So You Can Transform Your Career, in 2005. What was that experience like?
“What I found out about public speaking is that as much as I love it, it is sort of like “Groundhog Day;” you do the same thing over and over and over again.”
Robin: It was great. It’s in six languages and it is in paperback as well as hardcover. I am glad I don’t have to make a living as a writer because I didn’t make very much money. I did consider doing some speaking and consulting because the book gave me a lot of those opportunities, but what I found out about public speaking is that as much as I love it, it is sort of like “Groundhog Day;” you do the same thing over and over and over again. I didn’t really love it, but I am really proud of it. Some days my kids will read it. They are both capable of reading it now, but neither one has any interest. I am really happy I did it.
Avocationist: What made you want to write a book in the first place?
“So I was 43 and I went from being the young Turk at Time Warner to being the seasoned veteran at CNET in only one year.”
Robin: Well, my role at CNET had pretty much been to coach a generation of young people who had never worked before. It was an odd experience because when I left Time Warner, I was 42 and a year later I started at CNET. So I was 43 and I went from being the young Turk at Time Warner to being the seasoned veteran at CNET in only one year. Everybody was about 15 years younger than me at CNET. They were all sort of the same age; they are all in their late 30s now. A lot of my job was telling them what business was like.
“People kept saying, ‘You should write up your stories.’”
People kept saying, “You should write up your stories. You have been through so much and seen so much” and so on. Obviously I have a lot of friends in publishing from all of my years in it, so I talked to a couple of book publishers. They said there had not really been a general business advice book for women, so I geared it to women, even though my CNET experience had been with both genders. It was fun. I should have self-published it because then I could have controlled the marketing and distribution and sold more copies than they were able to, but I wanted to have a big name publisher behind me, so I made that decision.
Avocationist: It seems that the best situations for you were always some kind of company that was just beginning, whether or not you started it.
“I like being around new things. It is more interesting to me.”
Robin: Yes. I did not start my own company until “Parenting.” I joined “Mother Jones” magazine just a few years after it launched and I joined “Runner’s World” for the national launch. The magazine had been out there already but it was local. “Penthouse” had been in the UK and they brought it over to the U.S. and I joined it very soon thereafter. So I like being around new things. It is more interesting to me.
Avocationist: What parts of the start-up kind of companies interest you?
“I know that looking back on this, we are going to remember this as really wonderful.”
Robin: I think start-ups are more fun in retrospect, so I say that to people at Tee Bee Dee all the time. I know that looking back on this, we are going to remember this as really wonderful. We are already nostalgic for our first office. So I think it is more in retrospect. I take tremendous satisfaction out of the fact that “Parenting” created a new kind of magazine and it employed a lot of people over a lot of years and that it took some chances.
Avocationist: Of all of the jobs you have done, which was your favorite?
“The level of satisfaction and the friendships and just the achievement are very lasting to me.”
Robin: “Parenting” for sure, although as I said, it does look better in retrospect. At the time that I launched “Parenting,” I was in an unhappy marriage and my father was diagnosed with cancer and died 16 months later; it was a really, really hard time. That being said, the level of satisfaction and the friendships and just the achievement are very lasting to me, so that was really great. And if Tee Bee Dee is the wild success that I expect it to be, I think this will be right up there.
Avocationist: Were any of the transitions between these different jobs particularly difficult for you?
“So I loved it and I had a great time, but it was quite an adjustment from being the person who ran things, and I had to learn to take orders.”
Robin: CNET was an awkward one for me because I had been a CEO at that point for over a decade, but I did not go into it as a CEO role; I went in to support the founder who was the CEO. I would have been completely incapable of CNET’s CEO. For one thing, I was working part-time, but that was the eye of the storm in terms of the Internet explosion, and my job was sort of to bring management discipline to a very fast-growing, meteoric, crazy environment. So I loved it and I had a great time, but it was quite an adjustment from being the person who ran things, and I had to learn to take orders. One of the first things I did at CNET was such a huge faux pas and looking back on it, I wondered what I was thinking. I was used to making these decisions myself.
Avocationist: What was the faux pas?
“It was part of why they liked being at the company and it was penny wise and pound foolish.”
Robin: It was silly. The company had gone public but was nowhere near profitability and I started working in October. An employee came in and said, “Do you know that we spend $50,000 on our company Christmas party because everybody gets to bring as many people as they want?” So I said, “Wow! I didn’t know we let you bring people to a fully catered dinner; that is ridiculous.” I decided it would be for employees only and it would be an after-work party. That was a totally stupid, boneheaded move because for our employees at CNET, unlike the employees I worked with at Time Inc., it was a huge perk. They wanted to bring their dates. It was part of why they liked being at the company and it was penny wise and pound foolish. So the founders reversed my decision because it proved so unpopular, but I should never have even done it. It was also being in a support role instead of being a decision-maker.
Avocationist: Yes, because you don’t set the culture. Were there any people that were especially helpful to you in your different jobs or at key turning points?
“He was a huge mentor to me, and he is the person I could not have started “Parenting” without.”
Robin: I have a particular fondness for my very first investor, Arthur Dubow. He is dead now, but he was my first angel investor who wrote a check when I had absolutely never demonstrated that I could start a company. He was a huge mentor to me, and he is the person I could not have started “Parenting” without.
The other person who made “Parenting” a success is Carol Smith, who was the founding publisher, and now she is the publisher of “Elle” magazine. She was my complete partner in launching the magazine.
Avocationist: Based on what you have learned and experienced so far, what advice would you give to people who are trying to figure out what to do next?
“Just because somebody doesn’t fit the stereotype of what an entrepreneur looks like, it doesn’t mean they wouldn’t be good at it.”
Robin: I think entrepreneurship is very stereotyped. Stereotypes are different in different eras, but right now there is a stereotype of what the entrepreneur looks like, and I have never fit that. Not just because of gender and now because of age, but I find that entrepreneurs are a much more diverse group than we are given credit for. So we have different motivations. I personally am not motivated by things that a lot of entrepreneurs are motivated by. So just because somebody doesn’t fit the stereotype of what an entrepreneur looks like, it doesn’t mean they wouldn’t be good at it.
“There are a lot of parts of entrepreneurship that would be incompatible with happiness for many people.”
Also, there are a lot of parts of entrepreneurship that would be incompatible with happiness for many people. The lack of certainty and the lack of benchmarks; you have to make your own benchmarks eventually, and you don’t get a lot of positive reinforcement. I remember one of my investors with great fondness from “Parenting.” He never gave me one piece of advice that was useful, but at the end of every conversation he would say, “Keep up the good work.” I would say, “Wow! Somebody thinks that I am doing a good job!” Because you have to be so self-directed and in the marketplace, it takes awhile to get anything in the marketplace that is positive. So I think busting those stereotypes is a good thing.
Avocationist: You said that people have different motivations; what would you say are yours for being an entrepreneur?
It was a very incremental thing -- I tend to set incremental challenges, so it wasn’t about starting a company and selling it for millions of dollars.
Robin: Well, they are different for different times in my life. Motivation for “Parenting” was very much that I had been teaching a start-up course as a way of supplementing my income because I worked at a non-profit and didn’t make very much money. The students would come up with new magazine ideas, and my job was to help them figure out if they were good or bad ideas. So when I came up with the idea for “Parenting,” it was more like, “Whoa! I think this is a good idea. Let me just test it.” It wasn’t even to start a company. It was a very incremental thing -- I tend to set incremental challenges, so it wasn’t about starting a company and selling it for millions of dollars. It was more like, “Let me see if this is a good idea. Let me see if it tests well. Let me see if I can raise the money.”
“I would have missed the best thing I ever did in my life.”
Tee Bee Dee is sort of similar. I decided to commit to working hard until 2007, because I worked full-time and didn’t draw a salary and my kids are still pretty young. I said to my kids, “By the end of 2007, we will have succeeded so much that I will be able to hire somebody to replace myself or we will be dead.” The fact is, it is never that short a commitment. Now I don’t even lie to them at 2008; I say 2009. But it is a longer, harder road -- it always is. So for me, I sort of lie to myself in a way and say, “Oh, it will be a year.” Then, “It will be two years.” And then I get through that and I keep going. Other people, they see a whole five-year commitment and they sign up for that in the beginning. I think if I saw the length of the road that it was on “Parenting,” I wouldn’t have done it. I would have missed the best thing I ever did in my life. I sort of sell myself in by little bits and pieces.
Avocationist: So for you, it is sort of like taking the next step; what is the next thing I have to do to figure this out?
“I had a very clear moment because of the drama of my father’s diagnosis.”
Robin: You could have gotten me to stop early on at “Parenting” if somebody offered me a job that I was interested in. I was not that committed, but as I kept going through it and gathering people who wanted to work on it and learning more about the market for “Parenting,” I had one of the moments when my father got diagnosed where I thought, “Huh. If this had happened a month ago, I would have just given up on the magazine and been more with my family.” But I didn’t have that option anymore. I had committed and a bunch of people had given up jobs to work for me. So I knew I had to make it work.” It is rare that you get that kind of clarity. I had a very clear moment because of the drama of my father’s diagnosis.
“My father died knowing that the family was going to be secure financially because “Parenting” was a big success. It all worked out.”
At the time, I really was hopeful he would survive it. It wasn’t like, “He is definitely going to die and I can’t spend enough time with him.” But looking back on it, it all worked out for the best. My presence or absence didn’t make a difference. My father died knowing that the family was going to be secure financially because “Parenting” was a big success. It all worked out.
Avocationist: Do you have any regrets?
“I try not to have regrets. I try to learn from mistakes.”
Robin: I am one of those people who is always filled with regret, and I try not to do it to myself to much, because when you are an entrepreneur, it is a constant process of realizing what you did wrong and fixing it. So if you have a moment where you think, “Shit! Why did I spend money on that?” -- the money is gone already, so you have learned and you have to move on. So I try not to have regrets. I try to learn from mistakes.
Avocationist: What do you think you will do next, after 2009?
“I do not do future planning.”
Robin: Oh, that is a long time off. I do not do future planning. I can promise you that I am not writing another book. One was enough for me.
Avocationist: Robin, I really appreciate you talking to me. Thanks.