Cynthia Cleveland | Leadership Lessons From a Five-Time CEO/President with Over $4 Billion in Revenues

John Corcoran  9:16  

Right, right. How has it been working with CEOs and getting them to realize that they have to make a decision quickly, especially if they’ve been in a particular industry for many, many years? You know, you know, just in my experience with founders and entrepreneurs, a lot of times it’s it’s a mindset thing, like, yes, it could get them to bite the bullet, you know, they built this business for 10 years up to the point that it’s at and then it comes crashing down. And sometimes it’s hard for them to make such major decisions in a short period of time. So how is it been trying to convince CEOs to make that shift

Cynthia Cleveland  10:01  

That’s a really good question. And that’s why I say I mean, maybe I’m lucky in that the people that we’re working with have decided to have a coach, Coach, so they know they don’t have all the answers. And then I would say another part of one of the things that we do is we break down our goals, we’re very goal oriented. And we always look for what’s measurable and help our clients get to where they want to be by coming up with like 90 day plans, which at this point, that’s even a 90 day plan is a challenge. But part of our process helps that and that we sit down and look at what’s working, what’s not, and then set out three to five things that we’re going to do in the next 90 days as a team. And so part of that process, really, then, even if the individual leader isn’t quite there, when you sit down in a room and look at what’s working, what’s not, and go through your opportunities. Over the course of a day to two days, these sessions are usually about that time, although we’ve been doing a lot by zoom now, too. And sometimes we make those a little bit shorter. It helps everybody come along in the process. And then you’re all on the same page. Because I think one of the fallacies that are maybe the things people don’t recognize, is you need more communication than ever during this time. So if you don’t have like a daily huddle with your key staff, and seeing where you are, and what the immediate, being very immediate, and also being the leader who people want to follow. I think being a good leader and people who I’m proud to say that I deal with, they care about them. They know that top athletes have coaches, and so they have a coach because they have a mindset that they want to continue to grow. So maybe I’m a little bit lucky in that I have people who are predisposed, although it takes everybody a different amount of time to get there. So maybe they get there by themselves. Maybe they get there with their team. Maybe they get there with a little one on one coaching as well. Mm hmm. Two of your early roles as president were Teleflora, which provided gifts and services to a worldwide network of florists and then the other one was Imaginarium a specialty retail retail chain, which sold high end educational toys, gifts, books for young children,

John Corcoran  12:17  

both areas. You know, imagine there were a lot of changes in those industries in that time period that was late 80s to mid 90s, that you were in those roles. What do you bring from those two experiences specifically to the work that you’re doing today and, and to companies pivoting in, in the light of the pandemic?

Cynthia Cleveland  12:37  

That’s a good question. I’ve always taken something from the past. Like I remember when I first started at Teleflora, I bought our first licensing deals in and we weren’t even paying for licensing in those days, but I had done some of the first licensing for Barbie at Mattel and started realizing the power of taking another brand out what we did Oscar de la Renta and had and then started licensing Barbie is licensed and found that was a whole new revenue stream. So both licensing and licensing out so I kind of combined I remember one of my fun. One of my fun projects that I came up with was for Valentine’s Day. They’re one of the top products to sell along with flowers as a piece of plush stuffed animal. So I took my licensing ideas and we made the container for the flowers as a little dog house and we had Snoopy on top with his goggles on his aviator goggles. And so we did lovestruck Snoopy. And so it was a combination of things that I knew worked in other industries. I got Gloria Vanderbilt to give us those little perfume samples that they give away in department stores. And we did a swan which was her symbol at the time. And so instead of it just being our competition was FTD. And they were run by the floor. So that was kind of a big competitor. And yet, we found that by having something that already had some recognition branding, we were able to quickly get the consumers attention. And then when I took from that floor, one of the things we did as we looked at how expensive it was to sell our clients to sell the florist, we were selling to 20,000 florists, and it cost a certain amount to send a salesperson in the door. And we were sending them in the door to buy products. Were really, that wasn’t financially the smartest way to do it. So even now I was looking at, well, how could we sell so we started selling mailers. And we started selling to the phone, we figured out the lowest cost way to sell and we realized that our best sale would be opening up a new source because then you got a year’s worth of fees. So we totally revamped our sales force and went from them selling ongoing products to selling new stores. And we doubled the sales force, actually that less qualified people right out of school and dumped the coverage. And so now as I look at some of the situations that my clients today are facing, I think that’s exactly the right thing to do again, okay, during this world is the kind of sales force that you have the kind of sales force that you need. Can’t you know, some of these positions, they all you can’t do over the phone? Well, guess what, try it with some new people, try it with some of your more flexible people and start to prove that you can, or figure out at least if you can make up part of it. And you know, for financially, our advice is always in the beginning, it was cut once and cut deep. And then do the best, you can’t keep the best people that you have. And that always that just continues to remain the same, I would say, and Imaginarium. Again, I think I learned the power of brand. There, we were able to develop three or four different sub markets, we had a market of people who collected high end educational toys. One was breo. And they were little train sets that were wooden, and came with a big table. And the people who bought those just bought hundreds and maybe thousands of dollars worth. So we started marketing, I guess I was a little bit before my time, but I didn’t think everybody wanted everything. So we started collecting lists. I had half a million customers. But I started sub segmenting it into who was collecting the breo trains versus who was collecting Madame Alexander dolls. So we didn’t hit the same people up all the time. So that kind of focused marketing. It’s the kind of thing now that everybody’s looking at in terms of how many emails Do you want to get that have nothing to do with what you’re interested in? So now you do it digitally. But it’s the same kind of thinking it’s really finding what somebody wants and, and giving it to them or talking to them.

John Corcoran  16:50  

Right, right. Now, over the years, you’ve been very involved in YPO, and other women’s groups. As a female CEO in the late 80s and 90s. There weren’t as many women leaders back then what role did participate in these groups help? Or were there other relationships? Were there other women? Were there other mentors or coaches that helped you along and guided you in these roles and responsibilities as you took on more responsibility?

Cynthia Cleveland  17:24  

Well, that was it. It was an interesting time, I can remember when I was with Mattel in the 80s. I didn’t even go to Japan, because they did not want to, they would not deal with a woman there. And it took until almost 10 years later, when I was at Imaginarium that I actually got invited to speak, that I started to see that things were changing. When I went to Mattel, one of the reasons I went was because the highest ranking person I interviewed with was a woman and at carnation where I was before then I was the highest ranking woman as a manager. So you know, you look at a situation and you say, okay, you know, do I really want to spend and I was told I could be the first to the next level. But it was five years, and I just looked at that. And that oh my goodness, I don’t really want to have to prove myself that way. So I would say while there hasn’t been one particular person, I’ve had good mentors on both sides. So it’s been more of a, I haven’t tried to totally break it. I haven’t been the one to try to crash through. I’ve been the one to look for the easier path when possible. So the kinds of industries that I looked at, they were a little more welcoming, it was still strange. When I was running Teleflora, I was pregnant with my first child. And there were not a lot of women in there, you know, young 30s running a company and being pregnant. So that was I’ve always I just guess I got comfortable with not always being comfortable with. I was just me and I just decided I was just going to continue and whether there was a lot of a lot of other women around but then when I joined YPO, I found there was a women’s group within YPO it still only about 10% women 90% men, but when I found those women I found like I found my long lost sisters because they were also similarly motivated. They were all running businesses, many of them had families, and it was different than my girlfriend’s. It was great to have somebody who understood being driven and still wanting to have a whole life. So it’s been camaraderie. For me, I would say as much as anything. It’s a great organization. Any ladies, he listened to this podcast, and is interested in YPO please contact me directly. I’d love to get a few more ladies involved

John Corcoran  19:43  

Tell me I imagine you coach some women who are CEOs or presidents or executives or CEOs now. If you know the me tube movement happened right before the pandemic happened and it kind of took some focus and attention off of that. But I do want to acknowledge how that’s changed things. So how do you how do you view the world now for women leaders,

Cynthia Cleveland  20:11  

or leaders are probably not as bad as it actually is. for middle management. My concern today is for the middle management females in middle management, you know, there’ve been several articles about the supposition that it could set women back quite some time because of the dilemma that as mothers and working women we’re faced with when we’re having to homeschool our kids. And, you know, it’s just a difficult thing. And it’s very challenging for pretty much everybody. But I think in particular, women have the brunt of that up more. So when you look at one of the interesting things, I think some of us have noticed that countries that had female leadership have actually fared better during the pandemic. And there are a variety of theories around the fact that, you know, women do have a different leadership style, and they tend to listen to people more, and they just have they are probably a little higher, caring and concerned about the welfare of others, that’s a traditional female thing. The way we make our decisions, is slightly different, and maybe for the better. But I think it’s not an accident that those countries have had female leaders. So I’m now trying to help us all think about, well, what are those good qualities? And are we leveraging them enough in our leadership as women do we own who we are? And do we use it in the best of ways because I think we tend to underestimate ourselves because we’ve all had to work so hard to get wherever we’ve gotten to the things that are better about female leadership style. When I started you just tried to be like a man you just know, try to have them ignore that you were a woman. I mean, that’s that. That’s what I recall in the beginning. It’s just blended in as much as you could. Yeah.

John Corcoran  22:07  

anymore. Even the attire the woman suits with the guy, yes.

Dude, but on a woman basically,

Cynthia Cleveland  22:21  

in the shoulder pads, and not good luck.

John Corcoran  22:25  

The shoulder pain, I mean, like you could play a game of football on the shoulder pads, I think. I want to ask, you know, you, you referenced it earlier, but you have this diverse array of different industries, you’ve been involved in, you know, wineries, ebooks, you were co abroad lit with an online romance hub, featuring ebooks and digital games, all kinds of different areas. Are there any other tips that you have for entrepreneurs who are listening to this about what has led you to be successful in all these different industries?

Cynthia Cleveland  23:00  

I guess I’m always looking for the next thing. You know, I’m always looking for at heart, I’m a consumer products person. And I’m always looking at trends. I’d love trends. I love trying, it’s almost like a detective game. I like trying to figure out what’s going to happen next. And so for example, that the ebooks in the romance D includes was a client, and he’s a big suspense writer, and very good and very, very well known. He wanted to get more female readers, because females are the biggest pool of readers. So I just really started studying what was going on in that world. and saw that there, the romance market is just gigantic. And then you had that combined with the ebooks, and people reading on their phones on their Kindles, you name it. And so I had the opportunity, something came across my desk that was a library of old romance, True Romance several different magazines. Well, the magazine business was not talking about a pivot, this was exactly a pivot, the magazine business, nobody would want to be in. And this had a lot of debt. And it had a lot of issues. But I looked at it and I said, No, but that content, that’s a library. So I did an asset only purchase and bought all of the content of the library, and we repurposed it into ebooks To begin, and we’re actually out pitching everybody from Netflix to all of the different players, you would imagine what series around it because it goes through almost 100 years, and you would be surprised how much romance kind of remains the same there were certain that was gonna be my area

John Corcoran  24:37  

is gonna be my question. So you know, your question that I was gonna ask, I mean, like the romance literature from 8090 years ago, it seems it seemed up to date like it doesn’t seem

Cynthia Cleveland  24:50  

you would be shocked. I mean, there was this one series. I mean, some of it you want to play on the time period, and you can do that. Okay. Oh, man. That was what was one And these were supposedly true stories, which I’m not so sure. But there was one where she had to tell her fiance that she was hooked on. I don’t know, whatever the cough syrup or wherever was at the time and the 20s. So some of it was some of the, you know, forever romances forever romance and some of the issues that you think might just be now we’re more eternal than you might believe. But it’s a lot of fun. So to me, the game is seeing something that nobody else does, perhaps, or seeing things in a different way, or always looking at whatever past experience you’ve had. And how can you tell me that a success in one area generally translates to success in another area, there’s something about that that made it a success. And so if you can figure that out, and I had just been at Universal Studios too, and I had seen what had happened in music when music went digital. And so I saw it coming with the publishing in the same way. And so I figured, well, instead of being behind it, what have you got in front of it? And had it work with you? So I remind,

John Corcoran  26:08  

what was that like being so you’re at Vivendi, universal, mid 90s to 2002. That time period, actually, I worked on the universal lot for a period of time there, like around nine or so. So I was wrong. We could have crossed, we could have crossed fast. Exactly. Right. I was working at DreamWorks during that time. So Oh, really? Yeah. Which was a function. It was a fun company to work for at the time, because it was kind of like the Tesla of its day, it was a real hot company at the time. But tell me about, you know, you mentioned music and all the changes that are happening. That was your time in the late 90s. It was a period of Napster came along and digital music was before the iPod came along. A lot of times, people didn’t think that it’d be possible to sell music, because so many people were trading it illegally right here at a time there. You know, it was kind of like a big dam that had burst. But somehow, you know, Apple really managed to shift that. So what was that like working at Universal with that overseeing that shift in music? And how did you guys adapt?

Cynthia Cleveland  27:12  

Well, I was less involved in the music part, although I tried to see but we didn’t have the rights. I tried to see if we could do merchandise around some of our different music acts. But you know, at the end of the day, being able to capitalize on intellectual property is rights oriented. And as it turned out, all of the music deals, you know, a lot of times that would be brother in law, or somebody who had the mercs rights. And so I wasn’t able to get the rights that I would have liked to have had to be able, because I could have capitalized on big time. And as you know, over time, and during my time there, it was interesting, we went from our consumer products. In some cases, we would have to greenlight what the numbers would be for all the sales that we would make to get a movie made or to get a TV series made, because the numbers just started getting so much bigger. And during my time, I also took over video games, and video games that were like the heyday of the first generation of PlayStation. And we had a character called nuts, we have Spyro. And we had Crash Bandicoot. And Crash Bandicoot was one of the first games on PlayStation one. And we did a deal with Sony, where it was only on PlayStation one. And for that, we ended up selling 15 million games in one year. And it was just automatically on the unit. And that was just incredible. And we started seeing the cost per game going up to the point of being like a small movie 510 million dollars for a game. So we started during my time there and our own studio. And we started doing another game Spyro the Dragon had nothing to do with any of the entertainment. But then we started looking for ways to develop the games in conjunction with the movies, because the time to develop the game is almost the same as a movie. So if you waited until to start it for an A level kind of a game. You were always late. So it became a really interesting process to get involved in developing it. And I love games. I think games are just they’re still great fun. So my kids are big gamers and I still like it myself today. So it’s always just kind of looking at what’s in even the definition then of what’s entertainment games are entertainment in the same way to people as films are to others. So just looking at what it’s back to the same thing, what consumers want, and need and like and where’s it going?

John Corcoran  29:51  

Yeah, yeah. Well, you mentioned licensing music acts. I’m having trouble picturing he gave me an example of what that was. like or what you were envisioning?

Cynthia Cleveland  30:02  

Oh, I mean, even just trying to think of some of the big names, we had so many big names, but the big names that you had, you could do everything from just their merchandise on tour and make it nicer. You know, because a lot of the stuff that you see on tour is just kind of, and what we would do, let’s say, for example, with the Jurassic Park movie, we would not just slap the logo on a shirt, we would, we’d come up with all kinds of things. Okay, well, this is a shirt that’s going to appeal to our market for Jurassic Park, let’s say the number one market is little boys. But then there was also, you could if you did a whole different kind of a product that would appeal to teenagers. So we did everything from like, we came up with combining sports teams, and the different dinosaurs, and made it so that it was more than just the logo so that the like, for girls, we did little short t tops, and that a teenager would wear anyway that look like something that that your teenage daughter might go and buy. So it’s combining fashion and function. So for music, you could do the same, I mean, you could have so much better looks to things. And maybe they even come with some free downloads, you know, you could do different kinds of things. That would be way more than just the T-shirt, that could be your experience. So you could do ebooks, of the whole experience of the tour, because a lot of math now, especially Mo, not so much anymore. music artists shifted to having to make their money on tour. So you had to look for what to look for every last dollar that you could make. You don’t want to leave any of that money on the table.

John Corcoran  31:45  

Yeah, yeah, that was a major shift for the industry for certain. We’re running a little short on time. But I just want to ask you about, you know, what gets you excited, you know, in spite of, you know, some of the negative headlines and some of the pain that’s happening in, you know, across the economy and families obviously suffering and stuff like that. But beyond that, you know, there are opportunities there, there’s going to be great businesses that are built in this time period. What are you looking at? Where are the growth industries, or, you know, what gets you excited? And, you know, when you look at business today?

Cynthia Cleveland  32:23  

Well, the same thing always gets me excited about metric growth. You know, and I love seeing people succeed, I love seeing and helping entrepreneurs succeed. So it’s looking for what are the areas of growth and so you know, everybody knows, certainly the internet and things that you can sell in a different way and things that you can sell that are customized, I think people want things more customized to themselves. People don’t want the stuff quite so much as maybe they did at one point. So it’s what’s going to give their life meaning I think categories that I’m excited about our health and wellness, I think there’s never been a time that health and wellness has been more important. And people are paying attention in a new way. I think if you look at trends, look at home, I think anything to do with the home has good potential. Actually, I think things are going to really rebound. Now when it comes to making your home a more comfortable place. outdoor environments, there’s been a big boom, and that is people sit around at home, they look and they’re like, you know, I, they see all the things that are wrong or things that they want to make better, I think we realized that we might not need so much stuff. But we do need certain things, I think entertainment is going to take a whole different angle and that there’s more at home energy bars, big time, people are all drinking, drinking at home, they’re not drinking in a bar in the same way. But the way, then you get that people are starting to talk about their pods. And I know, I’m starting to do that in my own life where Okay, you’re not going to see 100 people. But you have a small group of people that you see. I have some friends who I have dinner with once a week and we go back and forth between our homes and eat in the backyard. And that’s starting to grow now. So I think the whole way that we entertain and spend time together, food has never been a better category, cooking, learning about that. And I think people are interested in just being together, games I think are gigantic. A lot of the online games that you can play are a fun way to connect with, with friends and family. So just think of all the things that you would want to do if you are in person. And if you can figure out a way to do it in a new way, whether it’s zoom or some other way to do it, or ways to still be able to connect. I think there are so many opportunities. I just see the opportunities and when I can help somebody be more successful at this point in my life. That’s what gives me pleasure.

John Corcoran  34:49  

That’s great. I love that. I want to wrap things up with a question I was asked which is let’s pretend we’re at an awards banquet, much like the Oscars or the Emmys and us Cynthia receiving an award for lifetime achievement for everything. You’ve done up until this point. And what we all want to know is, who do you think were the mentors were the friends were the peers, other executives, who are the people that you would acknowledge in your remarks?

Cynthia Cleveland  35:11  

You know, for me, it’s not one person, but it’s been so many people. And I would say, if there’s one thing that’s been impactful, to me, it’s been my YPO. Friends, I have some friends there, we get together in a small group, it’s called a forum, you know, eight to 12 people. And one group I’ve been with for 15 years. And if I even haven’t spoken to them, and maybe six months, I could just pick up the phone and call any one of them. And they would be there for me, and I would be there for them. So it’s all of those people who are my close circle of friends, and I don’t have hundreds, but I probably have 20 to 30. And it’s interesting, because now they’re around the world. So it’s the people who I’ve gotten to know really deeply. And I think in life, we have our family and I have a wonderful family. So I would certainly thank them. But it’s almost more cherished, what I call your chosen family. So the people in your life who are your chosen family who are just for you and encourage you. And hopefully you do that mutually. So I would have so many people to thank it would take too long. But I would say it’s all the people who’ve been there for me. And I like to think I’ve been that kind of friend and returned to a lot of people who I mentor.

John Corcoran  36:19  

Yeah, and by the way, I will. Anyone who’s listening to this, who hasn’t lived hasn’t been listening for too long. Go check out my episode with Sean Magennis, who recently left YPO. But he was CEO and President at the time, and talked a lot about YPO, the organization and many of my other guests have been YPO members. So they also rave about it. But this has been great. Cynthia, where can people go to connect with you? Or to learn more about you and the work that you do?

Cynthia Cleveland  36:44  

Yeah, go to And you’ll see Cynthia Cleveland there and connect with me there and I’d love to hear from you. All right, great. Thanks so much, Cynthia. Thank you, John. Take care.

Outro  36:56  

Thank you for listening to the Smart Business Revolution podcast with John Corcoran. Find out more at And while you’re there, sign up for our email list and join the Revolution. And be listening for the next episode of the Smart Business Revolution podcast.