Fearless - Ep 19: "The Lawyer" - Lisa Gersh

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"The Lawyer"

"It takes longer than you think with creative people. They're more emotionally attached to what they're doing than let's say managing and leading a sales force."

Lisa Gersh is a lawyer by training and a leader by instinct. After a career practicing law, she became the co-founder of the Oxygen network, before becoming the CEO of Martha Stewart omni-media and then the CEO of Gwyneth Paltrow’s company, Goop.

Along the way, she has proven over and over again, her willingness to listen, to learn and to lead.

I talked to Lisa about the childhood event that changed her focus, about learning how to nod and about the biggest mistake she ever made.

Three Takeaways

  • A relentless determination to walk into situations, really willing to invest yourself to make things happen positively.

  • An interest and willingness to learn from other people how to be more effective, more inspiring, more and more impactful.

  • An openness about what the future can look like without preconceived notions, combined with a willingness to learn from the past.


Episode 19: Lisa Gersh

Charles:                 “The Lawyer”

Lisa Gersh:          Business is just a series of problems that need to be solved, and so having people who come to you when they have a problem that they can't solve or want your input on it, that means you're being a leader, because they came to you. They're not afraid to come to you. You've shown an openness, a willingness to help them get what they need to get done, and they don't feel like they're being judged every time they ask you.”

Charles:                 One of the themes that’s started to emerge from “Fearless” is the distinction many of my guests make about the difference between being a leader and a manager. And it’s one that I personally agree with very strongly. In fact, I think this is such an important issue that I’ll make it a topic of a theme show in the future.

Actually, I want to say something about future shows. Next week is episode 20 - and it feels to me like this is the beginning of something. If you put all the transcripts together it's almost 200,000 words from people who have built and led and guided some of the most creative businesses in the world.

My personal realization is that it creates not only an opportunity but a responsibility to do something useful with that.

So, I want to mark what I hope will be one of many milestone for Fearless by by creating the first of what will become a regular feature.

There are a number of themes emerging from these conversations about what makes a Fearless Creative Leader. Next week, I’ll explore one of those themes in depth by pulling together pieces of some of the interviews so far and putting context around them. I’ll call these shows, The story so far and I’m going to do one every quarter.

But I digress. Back to the differences between being a leader and a manager.

There are lots of ways to look at these differences. If you’re interested in a rigorous, academic analysis, there’s a great Harvard Business Review article by Abraham Zeleznick that get into specific areas and compares them.

In my personal experience, the biggest distinction, usually comes in terms of emotional commitment. Being a leader means being out in front, carving new pathways and opportunities. Being a manager, means making sure those pathways are sustainable and supported. The former comes with inherently more emotional risk than the other, but also much more impact.

Managing is a crucial component of any successful organization. Without great management, there is no business. Just a lot of ideas, rapidly running out of oxygen.

But leadership is what separates the memorable businesses from the rest. It defines new frontiers and encourages people to join the journey.

I think many businesses would do better if they drew a sharper distinction between leaders and managers. Too often, I see the terms conflated and the lines between them blurred. Leaders need some management ability - there’s no reality today to sitting in a glass corner office and issuing edicts.

For instance, Reed Hastings of Netflix, famously has a floating office, spending his days walking the halls and engaging. It gives him real-time feedback on the mood and sense of the company.

I actually even found this myself. I could walk, into any of our four offices and within ten minutes feel the energy. Any number of times, I felt a shift” in momentum before there was any data to back it up. And what that meant was that we could re-shape the curve of the next phase of our growth.

 So yes, leaders need to be connected to the people that work for them. But when leaders allow themselves, to fall into management-first habits they loose two things. First is the company’s most valuable resource, the ability of the leader to shape the future. And second, the leader’s own passion for the job.

Leaders need to see the difference they are making in terms that are lasting and meaningful to them. If they are only focused on the day to day, eventually the emotional reward that gives us the confidence and the courage to make hard decisions is taken away. Or, put another way… leaders are people too.

So, What future do you want to create for your business, and how much of your time are you willing to spend on that?

Now… this week’s conversation.

Lisa Gersh is a lawyer by training and a leader by instinct. After a career practicing law, she became the co-founder of the Oxygen network, before becoming the CEO of Martha Stewart omni-media and then the CEO of Gwyneth Paltrow’s company, Goop.

Along the way, she has proven over and over again, her willingness to listen, to learn and to lead.

I talked to Lisa about the childhood event that changed her focus, about learning how to nod and about the biggest mistake she ever made.

Charles:                 Lisa, thanks so much for being here. Welcome to the show.

Lisa Gersh:          Thanks for having me. Happy to be here.

Charles:                 People who are listening to the show regularly will know what I'm about to ask you, but I'm going to take the risk that you might not. What's your first memory of creativity or something being creative?

Lisa Gersh:          As a child?

Charles:                 Mm-hmm (affirmative).

Lisa Gersh:          Individually, myself, being creative?

Charles:                 Mm-hmm (affirmative).

Lisa Gersh:          For me it was more play acting with my brother, and sister,   and friends, and just playing pretend, and that was always something I loved to do as a kid. You know, before there was anything on screens, I think kids spent more time doing things like that, but just developing your own characters and pretending to be someone you're not.

Charles:                 You grew up in the Bronx, right?

Lisa Gersh:          Yes.

Charles:                 I read somewhere that that your early years were very formative on you. Talk about the early stage of your life.

Lisa Gersh:          You know, I think when I grew up, I don't think parenting was yet a verb, and I think children grew up differently. You grew up. You had so much more alone time, no screen time. Just go off and be a kid. I mean, I remember literally like you would negotiate for, okay, you got out of school, and then you had play time until you had to do your homework. The play time wasn't a class that you went to. It was like go in the park and find this spot. I remember we had this spot in the park, which was   our house, and we would pretend to be ... That was our house, and it was a castle, and you were different people in the castle. Those are the sort of the things you did.

You know, also, I think you did that maybe because we grew up without any money really, and so you sort of that was your life. That's what you played. There was no instructor. You weren't becoming a tennis protege by 11. You never went to a tennis court, or a golf course, or anything like that, so it was pretty formative for me. I think until we were around 12 years old, we were sort of living the sort of normal I would call today what was then the middle class life, but then both my parents lost their jobs, and that really changed. We really had to figure it out, and I sort of made a decision very early on that I was going to figure it out, and I was definitely going to college, even though both of my parents didn't go. You figure it out.

Charles:                 That must have been a really dramatic awakening, a realization   that both parents lose their jobs at the same time and suddenly be confronted by a different reality.

Lisa Gersh:          Yeah. I mean, I remember saying to me ...My brother is two years older than I am, saying to me, "We're not going to college." I looked at him and I said, "Yes. We are," and figuring out how we were going to do this. You couldn't Google financial aid back in 1974, but you would go to a guidance counselor office, and get a pamphlet, and make phone calls, and actually do things like that, and figure it out. You know, I always wonder ...   That was very formative to me. I'm sure that no matter what situation you are, there are events in your life that are formative, and it doesn't have to be something that dramatic, but it has to be something that you know that you want. I wanted to go to college, and I wanted to get ahead and have a successful life. I don't know why I knew I wanted that, but I wanted that.

Charles:                 Where do you think that determination came from?

Lisa Gersh:          I think people are born that way. I'm pretty convinced of it, but I also think, you know, I admired my parents. I think it was an unfortunate situation for both of them that happened, but I admired my mother worked when I was younger. I always expected to work when I was older. I never thought that I wouldn't. I think you're born with it.

Charles:                 And did you want to work?

Lisa Gersh:          Yes. I always wanted to work. I never thought about not working. I never grew up thinking that I would have a family. I thought I would work. It really wasn't until one day that I woke up and said, "Hey. Kids would be a nice idea," and now of course you can't imagine your life without them. Yeah. Always wanted to work and, you know, never thought I would be in the creative arena, which was funny. I kind of went through what can I do? Then I'm going to go to college and make sure I graduate and get a job, so law school was the easiest path for me.

But as a child, I had a very strong affinity for books and television. I read a lot, and I watched a ton of television. I remember after school one day sitting on the couch and my mother coming in and being so annoyed with me, because I was watching television again. She said, "   You know, you're never going to amount to anything if you watch this much TV," which has become a running joke in our family, because I went into the television business, which everyone thought was really funny.

Charles:                 What did you watch? What were you drawn to?

Lisa Gersh:          I mean, remember those after school movies? I mean, any scripted drama is what I watched. I really didn't like game shows, although those were big when I was a kid. I loved scripted drama, and I still do. That hasn't changed.

Charles:                 So you got a law degree, and you started practicing   law.

Lisa Gersh:          Yes. Very happily. Thrilled someone was paying me real money. I was a little intimidated at first, because I went to a large law firm, where everyone had gone to Harvard and Yale, and I had gone to state schools, and I couldn't really figure out why they had hired me. Then I pretty quickly figured out that to practice law you need to have a certain level of intelligence, but that isn't going to make you the best lawyer in the room. The best lawyer in the room is someone who listens really well and reads body language  really well, and that's the best lawyer in the room, because really it's about figuring out what information you can get from other people and how other people are taking in that information. That is the skillset that you really need to develop, and that doesn't really depend on where you went to school, although it helps to be super smart.

Charles:                 Yes. I certainly feel like I should sit up straight or something, or maybe not. I'm trying to be conscious about that. How long were you a lawyer for?

Lisa Gersh:          I practiced law for 13 years.

Charles:                  And did you enjoy it?

Lisa Gersh:          I love it. I never thought I would do anything else. I really loved it. I loved learning other people's businesses, which is essentially what you have to do if you're going to represent someone either in a litigation or in a buying something. You have to figure out what the company does, so that you can really look and analyze the deal. I loved it. Then one day I got asked to represent someone in an employment contract, and that person worked in the media business.   I professed that I knew nothing about employment law, because it was a good friend of mine. I said, "Let me get you someone who really understands employment law." She said, "No. I need someone who's really going to be loyal to me, because you want a lawyer in that situation who doesn't care about the company that they're negotiating against." I only am going to care about my friend's contract.

I ended up representing her in this, and it ended up being sort of a large contract, because she left her existing company and went to a competitor, and it ended up being with   senior executives at big media companies. I really got interested in the media business for the first time, and so during the time which she went off to this other company, we stayed in touch. We were always taking walks and talking about her business, and I really was enthralled with her business and what she was doing. It was so interesting, and also near and dear to my heart, because I love the industry.

Then when she decided to leave the company she had gone to, for which I negotiated her contract, she asked me if   I would join her. I never even gave it a second thought. After practicing law for 13 years and thinking I had the greatest job in the world and really loved what I was doing, I just decided to leave and go start [crosstalk 00:07:41].

Charles:                 I'm interested in the fact that she wanted you to represent her, even though you had stated you had no expertise in the thing she needed help on. What do you think gave her that kind of trust in you? What do you think engenders that kind of trust?

Lisa Gersh:          I mean, we had a friendship, and it was interesting. We had gone   on a trip together, a trip with a group of people, and the trip had some complications, some travel complications. You know, when you're in that situation with a lot of people, traveling can be complicated sometimes. Somehow I ended up leading the unraveling of the complications and getting us back on track, and I think she saw that, and she was like, "Oh. This is a person who can really lead, and really figure out problems, and problem solve. I want to do something with her." Then that's  really what led to her asking me to handle her contract for [crosstalk 00:08:34].

Charles:                 It's interesting, isn't it, how often leadership comes down to the ability to show people you can make a difference for them.

Lisa Gersh:          Yes.

Charles:                 I mean, in as simple a situation as that, as you demonstrated instinctively leadership, I think that ...

Lisa Gersh:          I find it so interesting though. You can be in a situation, and I've been in those situations, and no one steps up, and I'm always the person who steps up. It's weird when I don't, and I find it difficult to be led in that situation sometimes.   If I'm in a situation, and I see someone else stepping up, and I know that they want to, it takes self-control for me not to.

Charles:                 You're suddenly around the media businesses.

Lisa Gersh:          Yes.

Charles:                 And exploring the possibility or looking into what that would look like for you from a professional standpoint. What drew you to it ultimately?

Lisa Gersh:          First of all, I'm always fascinated by the subject area. I'd been practicing law for 13 years, and I really had never dreamed of doing anything else.   I had two kids. I didn't have to travel. My life was kind of set up. I'd get to work, go home. I had it all set up, but I really trusted my partner in the business, and I thought, "Wow. This would be a great opportunity to really change, and expand my mind, and really figure something else out." It wasn't that I had figured everything else in the law, because I don't think you ever do. I think when people say they practice law, they really mean it, because you practice for your whole life, and you never get perfect, because every situation is different.

But it felt like just the right opportunity to do something just kind of out of the box, and I almost felt like I'd put in my time. You know, I'd gone to law school, and I'd put in my time, and I'd worked really hard, and I was in a position where maybe I could take this slight risk. The only really challenging part was I had a one-year-old at the time. I was really thinking, "Is this really the time to make a change in your life, when you have a one-year-old?" But I did it anyway.

The interesting part is when my partner asked me to do this, I again reiterated that I knew nothing about the media space, and I was definitely the wrong person for her to ask to come and do the partner, but what she really wanted was someone who was going to think differently about the media business, because this was 1999, and the world was having a change. When I think about the changes that are going on today, compared to then, it's nothing, but at that time   it was 1998. People were starting to really use the internet, both to communicate and as a media, and my partner really wanted someone who wasn't beholden to the way things had been in the past.

This was still like ... It's not quite early, early cable, but I'd say cable 1.0, so cable networks were still launching. The internet was coming into being, and we were going to launch the first ever convergence media property, which meant simply that we were going to launch on two platforms, the internet and television, which at the time was a very novel idea that no one had thought of.

Charles:                 Who was your partner?

Lisa Gersh:          Gerry Laybourne, and no one had thought of it.

Charles:                 You said you trusted her. What was is about her you trusted specifically?

Lisa Gersh:          Well, I had worked with her through the contract, so I saw the ability of someone to have trust   and give me a very long leash to go and do things and to say, "This is what I want to accomplish. This is my goal. You get there," and to iterate on that. For me that's a very comfortable way to work. It's harder when someone gives you an assignment or gives you a goal and then every step wants to know where you are, because I don't think you usually get there the way you think you're going to get there. The objective is to meet the goal, not necessarily to complete   all the steps. Completing all the steps for me is not that much fun, because it's fun to zig and zag when you're trying to do things.

I had a lot of confidence, but you know, I also wasn't even thinking at the time that I was ultimately going to be her partner in running it. I was just going to be there, and then it was we were partners doing this together, which was spectacular, and she's an amazing mentor and an amazing teacher, and we shared an office for 18 months.

Charles:                 Physically shared an office?

Lisa Gersh:          Physically shared an office.

Charles:                  How'd that go?

Lisa Gersh:          It was great. Well, first of all, we had to, at first, physically share an office, because we only had tiny, little space when we started the business. We were actually had some offices that Disney, ABC gave us at the time. We were actually in ABC's old offices, so we had to, but then when we had the opportunity to move, it was so helpful for me to learn the business by just being able to sit and listen, and you never had to spend time sending an email or communicating, so it just worked out really well,   and that was great. Then we ultimately moved into our space. We had like a glass panel between our offices, so we didn't have to walk back and forth. We could just open the little window.

Charles:                 Yeah. It's interesting, that shared office space dynamic. When Chris and I started our film editing company, we had this vision that we would just make every decision together, and we built a single office for the two of us with a big partner desk. About a week after the company opened we had the contractors come back in and put a partition between the desks. Then about a month later we had them come back in and extend the partition. Then about a month later I moved into a separate office. Husband and wife dynamics I think are [crosstalk 00:14:10].

Lisa Gersh:          Maybe would be different.

Charles:                 Can be different. Yes.

Lisa Gersh:          But it is interesting, and I do think that office spaces have evolved so much from then it was so unusual. Office spaces have really evolved, and so everyone is used to working in sort of an open space, and then when you take them out of that open space, it's actually they don't even know how to work. I think people who have never worked in an open space environment, it's sort of hard to get used to in the beginning, but once you get used to it, there is that dynamic of really collaboration that develops from it. I do think it has an impact.

Charles:                 Yeah. I agree with that totally. How did you define your partnership? Did you figure out you do this, and I'll take care of this, or are we going to do everything together? What was the dynamic in your partnership?

Lisa Gersh:          You know, I think at the start there were a few things that we just divided completely. If it was just a straight up creative programming and marketing, Gerry really was handling those decisions, although most of the time, and I'll tell you a funny story about this, she allowed me in the room. We were also raising money. We were hiring. We were doing distribution contracts to get distribution for the cable network. That sort of fell in my bucket, and then there was always that report in, and you're always listening to what's going   on, so you could chime in on other parts of the business that you really weren't working on.

Ultimately, as you got bigger, I always say like we'd hire people, and we would give off tasks. After about a year we hired a general council, so I gave off most of the legal tasks. Then we hired a CFO, gave off the finance tasks, HR, distribution, sales and marketing. You start giving them off, so that is in a sense what happens as you build a business. You do everything at first, and then you end up managing a bunch   of things and really have people who are individually focused on it.

Charles:                 We should say [inaudible 00:16:05] you're talking about Oxygen, right?

Lisa Gersh:          This was Oxygen. Yeah.

Charles:                 I'm curious from a personal standpoint. You were giving off tasks and giving off specifically to [inaudible 00:16:14] general accounts. Was that hard for you to do? Because a lot of people struggle with if I give this away, then who am I? What do I bring? Did you find that difficult, to give that away?

Lisa Gersh:          No. Gerry was really ... One of the things that's really hard when you go from   being a lawyer to a business person is management, because as a lawyer, you don't manage anyone, so learning how to manage people, learning how to do all that was something I was really focused on from the get-go. How do I do that? Where do I need to input on? And hiring people who you know where to input on. We had a great ... Oxygen had an amazing team of people, and just learning how to work back and forth ... The legal stuff was ... The stuff you know better is actually easier to give off. The stuff you don't know as well, it's hard to give off, because it's harder to manage something you've never done.

For instance, sales and marketing fell into my bucket ultimately. I had never run a sales team, managed a sales team, didn't really know what a CPM was. I mean, this was complicated, so I hired a really great consultant, who had been a head of sales, to really teach me the business, so that I  could manage the business, but the stuff you know is sort of easy to manage and know when you have to weigh in.

Charles:                 You said you were going to tell us a story.

Lisa Gersh:          Gerry was great about having me in every single meeting, and at some point I sort of noticed that I was never invited to a programming meeting, when someone was pitching programming. This was our bread and butter. This is what was really going to make or break us, our ratings on air. One day I just said to her, I said, "You know, I noticed that you never include me on any of the programming meetings." She said, "Well, it's because of the way you sit in programming meetings." I said, "What do you mean the way you sit in programming meetings?"

She said, "Well, you sit with your hands across your chest, and you can't do that in a programming meeting. It's not a business deal. You have to lean in when someone's pitching you a creative idea. You must lean in." By lean in she meant physically lean in. "And when they're talking to you, nod, like as if you understand. Just nod, do the nod, just so that they keep going and they give you their   best ideas, and they'll be their most excited, because they think that you're excited too. Whether you're excited or you're not excited, you have to nod." I said, "Okay. I got it. I can nod during it. I'll put my hands to my side, and I can nod." After that I got invited to one or two programming meetings, because I learned the nod, but that was her gift.

I think this is where people are great managers or not great manager. If you can make someone come in and give you their best work,   and take every idea, and always make it better, but make it feel like the person's idea. Gerry had this thing that we all had to do, stand up comedy courses, where you don't really know. It's totally unscripted.

Charles:                 Oh. Improvisation.

Lisa Gersh:          Yeah. We would do an improv class, because she used to say to everyone, "It's so easy to kill an idea. It's so hard to get an idea to flourish,   because smart people can kill any idea. If you just learn to say yes and not say no and keep going, even if you don't end up doing it, you'll see whether you want the idea or not," which she also applied to children. She told me when I had my first child that I had to learn how to say yes and not say no.

Charles:                 It's really powerful actually. IN my own life I tend to be one of those people who throw ideas out on the wall, and the people I value most from that perspective are the ones who let that stuff stick in the wall and slide around and [inaudible 00:19:59]. Oh. That's kind of interesting.  Because you're right. I mean, some people just can kill an idea in about eight seconds. It's incredible. How long when you started getting into programming meetings, how long before you felt comfortable enough to start offering your own insights and perspectives or thoughts?

Lisa Gersh:          A long time. I mean, I'm sitting with programming geniuses. Our head of programming was fantastic, and Gerry was so smart, so a lot of times I just sat and listened, which was really all I needed to do in   a lot of ways. Part of my role in those meetings was making sure the programming ideas had a business path that worked for the company, and so I used that part of my platform to make sure that we were in the right direction.

I mean, the only idea I ever really killed, which is kind of funny, is Keeping Up With The Kardashians. Really had that one right. Like who's going to care about the Kardashians? Which   maybe wasn't my best move ever, but that was the way I worked into the programming conversations, because everyone, as much as we love the programming part of it, it is show business, and it has to have a business path. Using my expertise on the business side was a better way in for me and also a more credible way.

Charles:                 There's a debate in some areas whether there's a difference   between leading and managing. Do you see a difference?

Lisa Gersh:          Oh yeah. For sure. I mean, leading is something I think you earn. Managing is something you're given, and so people will follow you, whether you're their manager, whether you're their colleague, whoever you are, if you earn it. If you're a manager, that's a different part of ... That's a part of leadership, but its not all of leadership. When you're managing someone, you're   giving them your goals. You're holding them accountable. You're doing all that. If you're really leading, you're giving them something else. You're giving them a vision. You're giving them a path. You're giving them encouragement. You're working with them to get them to where they need to be.

Charles:                 How do you see yourself?

Lisa Gersh:          I like to think of myself as a leader. I do manage, but I like to think of myself more as a leader than a manager. But, you know, in today's business, getting into the weeds and managing is pretty important,   and it's expected. You used to think of the CEO in the corner office. Your CEO is better off in the middle of the office and working with a team than sitting in a corner office, and setting out goals, and not being a participants, but I think everybody also has aspirations, You're a young persona the work. You're aspiring to be something in the future, and so setting out, showing that path and that vision to people is so important.

Charles:                 But you have to balance that   with and this is how we're going to make it happen.

Lisa Gersh:          This is how we're going to make it happen, and having a great team, you know, a team who knows ... I always think a great teammate for me is someone who knows when to bring me in and say, "Oops. Here's a problem. Here's where I was going. Here's what happened. I need your help." To me those are the best people to work with, because then you never worry they're not going to tell you, like when they get stuck on something. You know, mistakes happen. I mean, mistakes are great. You need to make   mistakes. If you're not making mistakes, something's wrong. It's like skiing. If you never fall down, you haven't skied a hard enough slope, as far as I'm concerned.

Charles:                 [crosstalk 00:23:40]

Lisa Gersh:          You need to fall. But, you know, business is just a series of problems that need to be solved, and so having people who come to you when they have a problem that they can't solve or want your input on it, that means you're being a leader, because they came to you. They're not afraid to come to you. You've shown an openness, a willingness to help   them get what they need to get done, and they don't feel like they're being judged every time they ask you.

Charles:                 Yeah. One of the very best people I ever worked for, maybe the best person I've ever worked for, was the head of production at DDB in Chicago, Grant Hill, who was really amazing at his ability to just be there underneath the surface for you when you needed, but he would give you plenty of room, sometimes to screw it up. He would never turn around and say, you know, "Now we've really got a problem." He just, when you needed him, he'd step in and he'd help you figure out how you could fix it. Yeah. It was very empowering and built   a lot of confidence in the whole department actually. It's rare, isn't it? I think it's a pretty rare treat to see that.

Lisa Gersh:          It's hard, because people get nervous. You know, manager, leaders can get nervous. "If my team makes a mistake, then how is that going to reflect on me?", as opposed to knowing, "Here's the direction I'm going. I'm going to get this team there, and I'm going to get the company there," and having that confidence is so important. I think also it's hard. You know, you have all these, I always think about this, all these young entrepreneurs, who are in   these big positions, who maybe have never made a real mistake and gotten out of it before. That's a very empowering experience, to know that you can make a mistake and move on. You know, I always think it's much better just to make a decision than not make a decision at all. For me that's a big mistake. I'd rather make a decision at the end of the day and wake up with it the next day that a decision's been made.

Charles:                 So as you look back on your time at Oxygen, what were your big takeaways from there? What did you learn about   yourself or the business?

Lisa Gersh:          I learned a lot about myself, and I certainly learned a lot. I learned the media business, which I didn't know before I really started, so that was a big learning. You know, I sometimes would go out and pull out the original Oxygen business plan that we wrote like right in the beginning when we were raising money, and all of it is wrong. All of it was wrong, except for two things, which was we said we would be profitable after five years, which we   were, and that we would be in 50 million homes after five years, which we were. It was necessary to be in 50 million homes really to be profitable as a cable television network at the time.

But if you look at everything else in that business plan, there's not a single number that's even directionally correct, and so what you learn about that is you set out with a plan and a vision, and there are somethings that you have to get to, but there are other things where you're just going to have to keep changing the direction   of the ship. We launched a cable network in a large internet site at the time, and I say that because you would never launch it that way anymore, but that's what it was, and we had basically had to close our entire web business in 2001. That was not part of the plan.

The plan called for half of our cashflow to come from the internet side of the business, and that clearly wasn't going to happen, so righting a ship that's going one direction,   where you have 250 employees working on the internet side of your business, and you're going to have to quickly change that if you're ever going to get to that one goal of being profitable after five years, which you need to, because you really can't raise anymore money, because now it's 2002 and the bubble has burst, so how do you do that? That's an interesting experience to go through, and we went through it.

Part of the reason we went through it was, well, Gerry and I would sometimes look at each other and   go through all the money we wasted, and we'd actually write it down, because we had wasted a lot of money in our minds, because we made mistakes. We ultimately got there, and we didn't point fingers at each other and say, "Oh. If you hadn't spent the money on that, we would be okay." We didn't do that. We just wrote it down on a piece of paper. Here is all the money we think we wasted. Now let's move on and figure out how to get this company profitable in five years.

Charles:                 Did you gain insights from creating that list?

Lisa Gersh:          No. Nothing. The list was   just I need to think about this again.

Charles:                 So a piece of self-flagellation.

Lisa Gersh:          Just a little bit. Just make the list and put it aside, because you keep thinking about it in your mind, so let's just make the list. Put it aside. Look. The world changed. Everyone was investing millions and millions of dollars into web businesses that had no real path to profitability. That was 2000, and everyone wanted to be in that business. Everyone. We were no different, and we were putting   lots of ...

We launched 19 different websites, all of sort of category headings that we thought would be interesting business, like ... and great names. Our sports site for women was called We Sweat. Our finance site for women was called Ka-Ching. Those were great names, but we had all those different URLs, and instead of just putting it all under Oxygen.com, which would have made so much more sense, we launched 19 different businesses. That made no sense, but who knew at the time? It seemed like a good idea.

Charles:                 Do you think this   was an idea ahead of its time in many ways?

Lisa Gersh:          Oh. For sure. It was ahead of its time.

Charles:                 It would work now. Right?

Lisa Gersh:          It would have worked a lot better. I mean, one of the big problems was we were going to create ... The idea was to create content that lived on both platforms, which is pretty much how it works in the world today. The problem was in 1999, there were dial up modems, and the phone would ring when you tried to log onto a website. Do you remember this? The phone would ring.

Charles:                 You've got mail.

Lisa Gersh:          Right. Exactly. The phone rang, and so you couldn't ... There was no video   content on the web in 1999, so the video content we were creating obviously didn't work on the web. You had to create different kind of content, so you were creating so much content with a model that really couldn't be supported, because there really was no real advertising on the web, but it was the phrase digital dollars for dimes or pennies at the time, and that's basically what it was, so it wasn't working. Really the only thing that advertisers wanted was what they still want today, which is what we now call super   native content, and they didn't want banners. Even then, no one wanted banners. It was ahead of its time. It would have worked better in 2005, when there was broadband penetration.

Charles:                 One of the stories about Netflix that I'm always absorbed by is ... Maybe this is apocryphal, but their ability to recognize the business they wanted to build and the calculation ... I think somebody told me that they ran a Moore's Law projection on the   growth of the internet and when the internet would be able to broadband and said, "Okay. We've got an eight year wait, so what are we going to do until we get to that point? Oh. I know. We'll send out DVDs by the UPS. [inaudible 00:30:42] by the Postal Service, because that's the most reliable delivery until the internet can be the most reliable delivery." That kind of forethought I think is extraordinary. As I said, the story may be apocryphal, but I like to think it's not, because who wouldn't want to build a business that is that strategic?

Lisa Gersh:          We had a lot of those ideas, I mean, early on, and you just couldn't do   them. We had a site called ... which is basically Etsy today called Women's Hands, where we had female merchants from small businesses all over the world. We took inventory. We literally took inventory, tried to create an eCommerce site in 2000 from small businesses around the world. Interesting.

Charles:                 Your description about multiple sites feels a lot like Refinery29 in many respects. Right? We're getting a billion page views, so clearly an idea before its time.   What made you decide to leave, and what was the next step for you?

Lisa Gersh:          We didn't actually ... I mean, I guess we left, because we decided to sell the business. Our investors had been in for nine years, and ...

Charles:                 Pretty long run.

Lisa Gersh:          Long run. Cable distribution was getting tighter and tighter, so cable operators really didn't want to launch any more networks. We had gotten to close to 80 million homes, which was almost full distribution at the time, but the renewals were coming up.   It was clearly going to be harder to get cable operators to renew and continue paying, which was really important, and there were very few independent cable networks left at this point in time. It was really hard from an ad sales point of view to be out there. Most of the cable ad inventory got sold through the large cable groups, like NBC and Viacom at the time, or Turner, and being that little guy at the end trying to get a few ad dollars was difficult. Even though the advertisers wanted us, it   was difficult, and so you could kind of see maybe we had gotten the business as far as we could get the business.

One of the disappointing parts about selling the business at the time was even though we had been in the business for nine years, the brand wasn't as fully developed as you would want it to have been when you're selling it, so that once you sold it, the brand would stay the brand Oxygen, and it would have a life beyond wherever it went. It did for some time, but recently NBC announced that they were changing   the Oxygen brand to a crime network for women, because the most successful show on Oxygen, which was launched 17 years ago, which is really hard to believe that it was 17 years ago, was a show called Snapped, which is about women who snap, originally women who snapped and killed their husbands. I think it was expanded beyond that, because I don't know that there are that many, but it was this docudrama that we made. It was really successful. It was great, and it's still on the air. It was the most popular show. Now it's a crime network   for women, which is disappointing.

So we sold the network to NBC, and I stayed at NBC for a couple years as the president of strategic initiatives, not running Oxygen, but working on a bunch of other projects, one of which ended up including buying and then, for some short period of time, running the weather channel companies, which was a very interesting opportunity, but it was in Atlanta. I got tired of literally my   friends would call me for forecasts. I'm like, "Seriously? We put the real forecast on the website. There's no secret forecast out there." We just don't want to tell you that it's going to rain, so we don't tell you. It was a really interesting time to be there, because at that point it was The Weather Channel, which is still in existence, because Weather on the 8s was something in 2010 that people still used, and Weather.com, which was then a   gigantic site, because it may be the best URL in the history of the world, Weather.com.

There was a small mobile business, because mobile was just getting going on smartphones, and iPads came out, so the business exploded in 2010. It moved from Weather on the 8s to mobile, and that pace of change was so extraordinary to watch and sort of be there at the time. Ultimately, the   Weather Channel companies, part of it was sold. The mobile part of the business and the dot com part of the business was sold to IBM, and NBC and the private equity guys still own the network.

Charles:                 Oh. Interesting. That's still true today.

Lisa Gersh:          Its still true today, Yeah.

Charles:                 That's an interesting marriage. From there you went to where?

Lisa Gersh:          From there I left when NBC was sold to Comcast, and I went to run Martha Stewart, which was also something I'd never done before. I'd   never run print, and I had never run anything to do with merchandising before. Half of the business was merchandising. They had huge licensing agreements with Macy's, Home Depot, PetSmart, and Michael's stores in the craft space, and four magazines, a radio show, a television show, so big media, big merchandising.

Charles:                 So the definition of a creative business.

Lisa Gersh:          And one of the more creative people in the world   is Martha Stewart.

Charles:                 Yeah. Talk to us about the challenge of getting or helping somebody who is intensely creative. Martha is obviously a businesswoman as well, but a completely original thinker, a remarkable original thinker. How do you manage both sides of that equation, from a leadership standpoint? When you walked in the door, what did you recognize the challenges were?

Lisa Gersh:          You know, it was an odd time for the company, because Martha was still not really fully   back at the company when I walked in the door, although she was coming back.

Charles:                 From being in prison?

Lisa Gersh:          Not from being in prison. She was in prison, and then she was on probation, so she couldn't be running her company. The creation of the Martha Stewart brand is pretty spectacular. I mean, it really is all Martha and all of her aesthetic. She has one of the finest aesthetics I've ever seen, both in home products and all the products   that she's created, as well as her ability and one of the most amazing palettes I've ever seen. She can look at food and tell you what's not in it. I've literally seen her do it, which was incredible. She's amazing to be around.

But when you have a brand, I think one of the things that's really challenging when people are building a brand that is themselves, because it's called Martha Stewart, it's really difficult to separate what is you and what is the brand, and to let that brand grow beyond yourself I think is one   of the most challenging things when there's a single creator. Now, most creative companies have a creative director, so that exists, but when it's your name on the door, there's a very different relationship between you and the brand.

Charles:                 What do you think has to happen for that to take place? I mean, you look at big fashion brands are obvious examples. Right?

Lisa Gersh:          Yes.

Charles:                 Like Calvin Klein's a good example of founders not involved, moved beyond. Most of them are actually. Many, not most, but many of them are. What do you think it takes to get   a business past the involvement of its founder?

Lisa Gersh:          That's a great question. I think if I could answer that, I'd be a genius, but I would say one thing is very true. I think that creator has to find a business partner they trust. It's a lot about trust, and are you going to let my creative vision evolve, and how do you work with that person to create that trust level I think is the most important thing, because basically, and especially when it's their name,   they feel like they're handing off part of their soul to you, because it's their name, and so it's so important to have that trust and for the creative to know that the business person really respects and values their judgment. That's to me the most important relationship you can build.

Charles:                 Do they need to want to build a legacy that outlives them? I mean, do you think that has to be fundamental to the shift?

Lisa Gersh:           That's an interesting question. I think most creative people i've worked with in that sense, like Martha, do want to build a legacy, do want that to happen, but if you think of the old examples of the father and son business, and the father's going to give the business to the son when the son grows up and is ready. It's always such a hard transition, because it's never ready. Business is never good enough. It's never perfect enough. It's never ready, so getting the creative person   to realize when that business is ready to go beyond them I think is really difficult, no different than any founder. It's like when is that business ready that I can trust somebody to take it to the next level? It's something that runs very deep with them and that they've started with such an early period of time, it's really difficult.

Charles:                 Yeah. I think it's a fascinating area of investigation actually, because as I look at creative businesses across the entire spectrum, it's   very hard. You see it in advertising agencies, the big ones. You see it in some fashion brands, but it's very difficult to find many examples of creative businesses that were built by founders who have not just outlived their founders, but actually thrived beyond that. Production companies typically don't. It's very hard to find examples of production companies that are more than 30 years old.

As I said, big, traditional agencies have done it, but the modern ones haven't yet demonstrated they can do it. Some   of the fashion brands are still struggling to figure it out. I think it'd be interesting to do some investigation actually into what are the characteristics, and how do you make that transition, if you are a truly original thinker and you are running a business that is built around you?

Lisa Gersh:          Why do you think you see it more in fashion brands than media brands?

Charles:                 That's a really good question. I'm not sure. I wonder whether it's because fashion designers tend to get recognized younger   in their lives and establish themselves more quickly and therefore get tired of it sooner and want to go and figure out what else they're capable of. I think that's true in some cases. It's clearly not true in every case, but I think it's true in some cases. I do think there's a big ... Well, there's clearly a big, emotional aspect to there, isn't there, which is he fear of sort of a leader to [inaudible 00:41:22], but the fear of will I be relevant if I step out of the way and allow other people to demonstrate that they could do this too.   What does that say about me if other people could do it.

I often wondered if the, I don't know, it's not fair to call it the demise of Apple, but what you might describe as the mild retrenchment of Apple since Steve left ... It's certainly not the innovative company was. It's certainly not as dynamic. It's not as exciting.

Lisa Gersh:          It's interesting to me that creative founders like that don't see more of their, quote, legacy in developing   10 people who have parts of their vision and go on to do great things and want to be the parent of that like look what I created. Bringing Gerry Laybourne back up, one of the things that I think she was so brilliant about was she viewed her role as a head of the company as to create the next generation of CEOs. That was her role. That's what she wanted to do. It's always interesting to me when   you have a creative person where they don't say, "I want to create 10 people who can come on, and take over, and create, and go on to build great brands, like I've built." Why don't they often think that way? That's not often the thought process.

Charles:                 No. It's not. I think it's different too when you are the artist itself. When Chris and I built our creative business, we were not film editors in our case, and so we had a very clear understanding of what we were trying to build and why. We developed a saying   for ourselves very early on that we use to this day actually when we're advising owners of creative businesses. We work very hard to make ourselves irrelevant. We said, "Success will be this business not needing us anymore." Right? If we build it around that simple premise, is what were doing today making us more important or less important to this company?

If we make ourselves less important, then we can leave, and it can continue to grow, and we will get economic benefit. We'll get insider understanding, and education,   and self-awareness out of all of that, and the company can go on being even more successful. I think if you can bring that mentality, which is hard, but if you can bring that mentality to it, you create all kinds of possibilities. I love the notion of my job is to create the future CEOs of the world.

Lisa Gersh:          Right. And or create the 10 new creative businesses that get launched off of this platform that go deeper into an area. You know, if you're covering a bunch of different areas, wouldn't that be amazing?   That would be the goal, but that's very hard to accomplish, and that's not often ... It can often be threatening to a creative founder when a young or an internal creative person rises up and gets recognized. That can be really threatening.

Charles:                 Really threatening. Yes. Absolutely. What did you learn about your own creativity at Martha?

Lisa Gersh:          Well, I learned that I was not crafty.

Charles:                 You were comparing yourselves to the world's standards though.

Lisa Gersh:          Yeah. I was comparing myself to ... Even   though as a child one of my jobs was working in my parents store, where they sold ... And I taught needlepoint. I was not crafty. I learned that I could not have cupcakes brought to every single meeting, because I would definitely gain weight for the first time, which would not be good, so I banned cupcakes from my meeting. Look. I just love the whole process and diligence with which Martha and the company pursued their   exploration of creativity, whether it was in the kitchen, I mean, testing recipes five times, making sure that they were right when you used them, really exploring the world outside of the office in terms of what was going on creatively I though was just incredible The openness and the love of the aesthetic was really wonderful to watch.

Charles:                 So from Martha you went to Goop. I know it wasn't immediate.

Lisa Gersh:          No. I didn't go right away. After   we sold oxygen, my plan had been to take a year off, and then I ended up staying at NBC. Then I got involved with The Weather Channel. I ended up staying and doing this education thing for a while, so I didn't take a year off. Then I was going to leave NBC and take a year off and ended up going to work with Martha. Then I decided I really didn't need to take that year off. I had never taken any time off. I'd worked since I was a kid. It was time.

I really   wanted to explore for profit education, so I spent year exploring for profit education and really fascinated by the space. I'm still fascinated by the space, but I think it was one of those spaces where I thought, "Okay. Is this Oxygen in 1999. Maybe the idea is a little early, and it's better to wait and sit it out for a while." I was exploring that, and doing that, and sort of really happy taking a year off, although I didn't really feel I was taking a year off, because I was   working with the University of Phoenix actually on the for profit idea, so I actually had a consulting thing, so I wasn't completely off, but it was close enough.

I was really getting close to deciding, "Should I really launch this venture or not?" Someone introduced me to [Gwyneth 00:46:50], and I said, "No." She was actually looking for ... She was very involved with Tracy Anderson at the time. She had an exercise fitness   program, and they were looking for a CEO for that company, and someone asked if I would meet with Gwyneth. It's sort of a meeting you're going to take, no matter what the business is, just because I had heard such nice things about her.

 I met with her. I did not want to run Tracy Anderson, the fitness business, but I did start to get involved with her and Goop, and then ultimately she was moving business from the Uk to the US, so I decided ... Well, one of the things that really fascinated me at Martha   was you have this content business, and you have this merchandising business, and so much of the merchandising business is inspired by the content. How do you pout those together more, which is hard to do at Martha, because it was a licensing business. All the product was licensed. You didn't actually own the product.

But Gwyneth really was writing content, recommending product, really wanted to go deeper into product. It was like, "Wow. This is a way to put content and commerce together." I've always wanted to do that. A fascinating idea. That's why I decided to do that.

Charles:                 What do you think is the future   of business? Interesting listening to those different lenses. As you look at it now, if you were advising somebody on how to start the ideal modern media business, what would that look like?

Lisa Gersh:          Oh. That's interesting. I think the ideal modern media business, and I would call it sort of the third wave ... If you think about video, I think the third wave ... We had broadcast. Then we had cable. Now we have digital. It's all digital. It's going to get inspired   on YB, because that's where everyone is watching. It's going to get inspired on YouTube. Those brands are going to develop into long form, and they can get licensed out to different platforms, whether it's Netflix, Verizon, Hulu. They'll get licensed out, and then hopefully if the brand gets big enough, it'll be part of an over the top package. I think that's 100% the direction of video today, and I think that the current cable networks are going to be really challenged by this.

Charles:                 Because?

Lisa Gersh:           Because no one's watching linear television. It's funny. If you look back at the history of this, everyone thought linear television was going to be over when the remote control was invents, because when you and I were kids, there was no remote control. You literally had to get up and change the channel, which was literally like a dial. Remote control didn't end linear television. Everybody thought that DVRs would end. It didn't not. It's really streaming that's ended it.   I do think that linear ... I don't know anyone who watches linear television, which is unfortunate, but I don't know anyone who watches linear television.

I think those brands, you know, in media today flat is the new up, and they're not even flat anymore, so they're really scrambling on trying what to do. I think in the meantime the companies without legacies that are beholden to cable operators or other platforms and haven't invested all their money in that are going to rise, and they're going to become the new brands.   Kids don't care about those brands, just like they never really cared about networks. I used to ask my kids, "Are you watching cable or network," and hey didn't know. They didn't know what a broadcast network was. It's okay, but they're not ...

In fact, my daughter, [Maddy's 00:50:18] going back to school tomorrow, and she said to me, "You know, I'm thinking that maybe you should just send my ..." She's going out to California. "Would you send my desktop computer   out to school? Could you shop for me? Because I'm not going to get a television. I'm not getting cable." She had it in her last appointment. She's like, "I'm not going to get cable. I only watch Apple TV." She's not going to get it, and no one that age gets it.

Charles:                 Yeah. Nowadays.

Lisa Gersh:          I think that's the future. I think there's some really exciting brands out there, and I do think that's going to be the future of media. On the commerce side, which I think is really interesting also, because all the retailers are struggling,   new brands are popping up in different ways. I was with my daughter and we were in Soho the other day, and there was this brand called Sunday, and they launch a new product every single week.

Charles:                 Every week?

Lisa Gersh:          Every week they launch a new product. It's an apparel company. They launched a new product. They launched on Instagram, and that's their business. It's completely different model, so those models are really going to evolve, and you really have to figure out, if you're   thinking about commerce, how you're not going to just get eaten alive by Amazon. That's going to be something that requires higher touch, something that's unique, that you can't get elsewhere. I think those exist. I think they're still out there. You're also going to see I think brands just going direct to consumer, because they can, and figuring out high touch points of service, which differentiates them from the other side.

Charles:                 Experience is going to become more, and more, and more important. Isn't it?

Lisa Gersh:          Yeah. I think so too. I was out in a store the other day, and I noticed   that they created this whole feeling of a market, instead of sort of being in a store. They were clearly trying to move towards experience, but then I was watching something the other day. Someone had a fitness class. Now, if I'm shopping, I don't want to go work out, but giving people a reason to go. You know, out in California, in Malibu and in Brentwood, there's Country Marts. Have you ever been to the Brentwood Country Mart?

Charles:                 Mm-mm (negative).

Lisa Gersh:          It's interesting. They're like outdoor shipping malls. They're cute,   so they don't look like a strip mall, but they have great places to eat, and they have a toy store and a barber shop. You're giving people a reason that they would go there, other than to shop. Maybe when they're there they'll shop. I think those kinds of things, things that you have to go do, like a barber shop, or a salon, or ... Are you going to change those realities? I don't think retail's going to go away, because I think that's part of an experience that people love.

Charles:                 Yeah. I think that's true. I agree with that. The last couple of questions. As you look back at   your career so far, what have you learned about-

Lisa Gersh:          Thanks for the so far.

Charles:                 Yeah. So far. I have no doubt you'll go into even more astounding things. As you look at the moment, what have you learned about leading creativity and unlocking creativity in a business environment.

Lisa Gersh:          It takes longer than you think with creative people. They're more emotionally attached to what they're doing than let's say managing and leading   a sales force. Sales team has just a goal. They're driven. Their goals are clear, but for the creative community it's much more emotional and much more before about revealing themselves and letting them feel comfortable to reveal themselves. At the same time, moving towards a goal is really important. I love that process, and I love and admire ... If you love and admire creative work than being   part of that process can be so exciting.

Charles:                 My last question for you. What are you afraid of?

Lisa Gersh:          That's a really interesting question. I don't know that I ever thought of anything that I'm really afraid of. I think, like everyone, I'm afraid of failure. I don't like or ever want to fail at something I try to do, so you're trying to pick something where you don't think you're going to fail. How you define   failure is the totally open question, but the ultimate failure. I don't mind the mistake part. I just don't want to fail at an enterprise where I thought I could do something.

Charles:                 So interesting. I like to wrap every episode with what I describe as three themes that I've heard. I'll throw these at you, and you can tell me that I haven't heard anything you've said exactly.

Lisa Gersh:          That I doubt.

Charles:                 But my listening skills ...

Lisa Gersh:          That I doubt that.

Charles:                 The first one obviously, to me anyway, is this   relentless determination you have ... I mean, you talk about it from a very early age, but it seems that you walk into situations really willing to invest yourself and throw yourself into trying to make stuff happen positively. Second is your interest and willingness to learn from other people. You're very open to that and clearly don't walk in thinking you're the smartest person in the room and I don't think want to be. You're interested in what else can somebody teach me that would make me more effective,   more inspiring, more, more impactful.

Then I think third is you have an openness I think about what the future can look like that I think is incredibly important. I don't think you walk around with preconceived notions. You combine that I think with looking back and saying, "Now, what have we learned that didn't work, and what could we learn from that in the past?" There are a lot leaders I think who   tend to get precious about, defensive about, "Well, we tried it this way, and so therefore we have to hang onto that. I don't see much of an answer of writing down all the ways that you wasted money and then just saying, "Okay. Fine. Fine." [inaudible 00:56:13] and no Move forward is something very healthy about that. Do those three resonate with you?

Lisa Gersh:          Yes. Very much so.

Charles:                 Lisa, thank you so much for being here tody. I've loved this conversation.

Lisa Gersh:          So fun. Yes. Me too.

Charles:                 Great. Thank you.

Charles:                 You've been listening to Fearless: The Art of Creative Leadership. If you like what you've heard, please rate us on iTunes. It helps a lot. If you want more information on this episode or any of the others, go to fearlesscreativeleadership.com. Thanks for listening.