Cynthia Cleveland, Being Bold and Courageous as a CEO and Coach (#174)

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Cynthia Cleveland is the CEO/President of five companies, and has learned how being bold and corageous as a CEO and coach can make a dramatic difference. She has a track record of identifying and capitalizing on emerging trends to create new businesses. She has successfully navigated Fortune 500 companies, run a venture backed business, and launched an entrepreneurial digital business.

Being Bold and Courageous as a CEO and Coach

With over 20 years of product development and marketing expertise, Cynthia Cleveland has successfully directly introduced over 1,000 products withover $4 billion in sales volume for well-known companies such as Universal Studios, Carnation Foods, Mattel Toys, Teleflora floralgifts, and Imaginarium toy stores.

Now at CEO Coaching International, she works with the world’s top entrepreneurs, CEOs, and companies to help them scale & grow their business, develop their people, and elevate their overall performance. Data speak for itself, as CEOs and entrepreneurs working with CEO Coaching International for three years or more have experienced an average EBITDACAGR of 59% during their time as a client, more than 5x the national average.

If you’ve always wanted to increase your profitability, develop new strategic relationships, maximize sales performance, and create real value in your business, she’s there to make that happen.

Talking of which, let’s see how’d it happen for Cynthia Cleveland!

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Podcast with Cynthia Cleveland. Being Bold and Courageous as a CEO and Coach.


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Cynthia Cleveland, Mike Malatesta

Mike Malatesta  00:16

CYNTHIA Thank you so much for joining me on the podcast today. See if I have John Corcoran, to thank for introducing Cynthia and I John’s been on the show before he’s been a friend to the show and actually helped me get started with podcasting, way back when, three plus years or so ago he gave me the confidence to actually move forward. And he’s been a good mentor and a good connector for me, as, as well and as as Cynthia since we first talked he’s introduced me to a number of other folks that I’ve had a chance to talk to or will on the podcast and it’s been very exciting including David Friedman who was really a few episodes ago, with his culture wise business and it’s just fascinating backstory as well so CYNTHIA Thank you for that.

Mike Malatesta  01:25

we also have a YPO connection which we’ll probably get into as well. I start every show Cynthia with the same question and that is how did happen for you.

Cynthia Cleveland  01:37

Well, as we were discussing right before we started, there are many points I could begin with, but I think I would like to start with, how did I first become a CEO, because a woman of my age and I was in my early 30s It was quite unusual. But what made it even more unusual was that I was seven and a half months pregnant. So you could imagine that long ago that was kind of a very unusual circumstance. Sure, so I was consulting to accompany I had just left my job I was the vice president, top toys. My husband and I had both left under different circumstances, but we both left, of course immediately I’m pregnant and so I became an unintended consultant, because that’s just what came my way and I was working for a company, and they sent me in one of their second companies, and I was working, and it was the week of Christmas, and the owner or owners it was fairly large company, but they were owners of Christmas, and nobody answered the phone but we consulted. And that led to somebody getting fired, and they’re getting proper advice. First job of running the company, and it was one of those pivotal moments. I had no idea was coming, and it was not like it wasn’t even in my life plan, to be honest with you, and it was really kind of a tough choice about having my first child and being restarted such a big endeavor, but I think what, what I did was something that perhaps your users can learn from to. What helped me make that decision was I looked, five years in the future. And I said it right now this is a very confusing situation I know what I should do. But five years in the future, what would I regret more. What I regret trying it and failing, or what I regret not trying it and not knowing whether I could have done it. I was no fool, I realized those kinds of circumstances don’t come along every day. And for me that suddenly made the decision very clear, I was less afraid of failure than I was of not knowing. And so I left, I left, I left forward and to be honest, I’ve never looked back. It’s, I worked my entire children’s growing up years, and I’ve managed, I don’t know how well I did everything but wherever I was I tried to be fully there, and selling and led to I subsequently have like five different companies so it led to a real good YPO was one of my first endeavors joining that so that was my how it happened.

Mike Malatesta  04:14

So seven months pregnant, you’re consulting because your position or your whatever time at Mattel had had ended, you’re in the office. On Christmas or near Christmas, and not on Christmas, I hope, and no one’s there. Except you, and you’re just working on a project, and you’re just working like on a project, but how did the owners even become, be aware of you outside of the fact that you picked up the phone.

Cynthia Cleveland  04:49

I started working on they own another company, and they were collector dolls I’ve certainly worked on dolls with Mattel Collector No project and this was the second company, and they had problems with their products and I love products, so I went in and was looking at how to, you know, reconfigure their assortment and figure out what was, what would be good products going forward. And I guess the way my brain works. I ultimately ended up doing more, because I looked at, well, you can’t figure out the products that are going to sell unless you understand the consumers, and then we were selling from Florida so that I had understood floral network, and set the margins, and so I ultimately probably over delivered in that, to answer the question, where they hired me to I had to really understand the business. And so I was giving broader business advice versus just what I had been hired for. So, I was there where I didn’t, I wasn’t there because somebody was going to check on the others that are working and I guess, probably a combination of being there plus the work that I had done made them believe that I could do it.

Mike Malatesta  05:53

And I imagine there was some dissatisfaction with the current. Oh, Yeah,

Cynthia Cleveland  06:00

I found out that people knew he was going to retire, they just didn’t know when. And so a lot of other people were thought they were considered being considered for the job so it was, it was a rocky start for me.

Mike Malatesta  06:14

Okay, well I’m glad you went there because I wanted to go there as well after I asked you. You mentioned the failure you know you look five years ahead and, you know, made this sort of took this leap, like if I failed it would be okay. At least I tried right but I wonder it also, were you thinking you were ready, which is maybe different than a fear of failure I was just curious.

Cynthia Cleveland  06:37

You know, I think that’s a funny thing about me is I guess I don’t look at things that way. Person business job I had none of the qualifications, they really didn’t have the qualifications that they were looking for but it was what I decided to do. I remember my boss, several years later I only realized that he shouldn’t have hired me based on my credentials. Why on earth, he should hire me. And he looked at me and he said, I said why did you think I could do this job, I didn’t have any of the qualifications. He said, Because you thought he could. So I think there’s a part of me that I never, I don’t think it’s a cockiness, it’s just I always figure I’ll figure it out. What I don’t know I’ll figure out. Sure. I have some level of. I know I don’t know everything, but I will figure it out, figure it out. And so, I think I’ve been bold, my entire life and making changes from industries and so forth, because I’ve just decided what I don’t know I’ll figure out, and so is that more than anything. Yeah, okay, myself as a CEO, but, but I figured I would figure it just the way every project that I dealt with everything that I’ve done I’ve always figured things out. So, that’s just, I guess part of me.

Mike Malatesta  07:55

Yeah, so like a, maybe like a humble confidence so you’re not cocky, just confident and.

Cynthia Cleveland  08:03

And you and I think part of that is, I’ve never thought I could do it all myself. Okay.

Cynthia Cleveland  08:13

Knowing what I’m good at and knowing what I’m good at, and surrounding myself with people that are better than me. I’m not at all intimidated, in fact I’m inspired by people who are better at what they do. And so I knew I wouldn’t be doing it alone. And I love to work in a team. And so by working in a team. You’re better because you can strengthen those parts that are naturally. Sure.

Mike Malatesta  08:37

So let’s talk about this rocky sort of start I mean you’re, you’re an outsider, you’re a woman. You’re, you’re about to give birth, never been a CEO before. And, you know, you get selected by the ownership. And a lot of people get passed over feel like they’ve perhaps been passed over. And so, take us through that experience, how did you manage it. How did you how did you deal with it. How did you navigate through it, what were the hurdles that you ran into. Besides, besides giving birth. Soon after, soon after

Cynthia Cleveland  09:21

reading to go out on my maternity leave, I discovered that the head of sales was doing something, not illegal, but bordering on immoral, you know, again in signing up, doing something to achieve a bonus that wasn’t really warranted in the way that it was being done. So, by first moral dilemma was do I share this with the owner, or do I let it slide because you certainly don’t want to be without a salesperson in your head of sales, while I’m about ready to be out for a bit. And I guess that was another one of those decisions where it’s like okay well who are you, and I realized I couldn’t not share that information. And much do I really, because I was worried why I made a mistake in this whole thing and you know you’re gone, I need to find somebody who’s there. Or he could just say well if that’s okay with me, and your judgment has been wrong. But the first thing that he asked me said what do you want to do. I said well to be honest, I don’t want this person around that we can trust. I don’t want somebody around why can’t. Why can’t trust who’s, you know, looking out for the best of us of the company. And he said, You’re totally right, I agree with you fire. So that was the talk about a rocket road that was my first big rock that I encountered. Gradually I learned that there were probably four or five other people who were all hoping to have this position, and it was actually at a YPO event and this is, this is a funny story that will come back again. We had somebody from Myers Briggs came in and did reports on ourselves and our spouses, so I learned about Myers Briggs, assessments, and it was really helpful, even for my husband, myself, we’ve been married maybe two to three years at that point. And I learned that that the individual also came into companies and did team analysis. So I immediately turned around and hired numbers, and it came in and I will tell you that helped me get clarity on. Who were the, who were the keepers who were the people who were just so resistant to change, and not only the working together and just hated me and we’re not going to get over it, it became pretty apparent in a way that I think it would have taken me. I don’t know, six months to a year to figure out individually by just having that to process and seeing things through somebody else’s eyes, so that I, You know once I learned something, I tried to apply it again and again so every company I’ve been with since then, that is one of my first steps is to get a team assessment because again I just believe. I’m okay. As an individual, but I’m a better leader because I have great people so I want to build your head into this day with my coaching, that’s one of the first things I do with a client that I’m coaching we look at tracking, because people will get you to where you are today, sometimes aren’t the people who are going to get you to where you want to go.

Mike Malatesta  12:18

So we’re going through kind of something like that in our business now and it’s happened before and I’m, I guess what I’m wondering is, when you go through say Myers Briggs let’s just stick to that although there are other tools out there but let’s stick with that. And you realize that you’ve got bad fits or not the right fits maybe that’s a better way to say it, how, how do you go about taking the action Cynthia because it’s, it’s one thing to get the information but then you know it’s kind of can be kind of hard to say hey, for no other reason except this your, you know you’re not a good, good fit, or do you wait for other reasons to come up or how do you how do you how do you make it actionable I guess is my real question.


Well, I think, an assessment alone isn’t going to give you that answer really hard, you know it’s setting deliverables, and are they meeting the deliverables are they constantly, not referrals, are they not able to change that with all business especially in this past year, we’ve learned nothing else, you have to keep looking at your business book I recently read, it’s called a beginner’s mindset. So it’s very hard once you’ve been in a business for a while but, but it is what it is you have to just keep looking at it through fresh eyes again and again. And so first I look for is to be a good person is a person who we still want to accompany it is it like maybe part of the job that they’re doing that’s really well or is it the right person in the wrong seat, and sometimes that actually is the case, right. That’s the ideal scenario is where it’s a good person. But, you know, I’ve seen some profiles recently now I use just as well, but where do you have somebody with the sales personality in the financial job, and you’ll learn. It wasn’t too big of a surprise them to learn that the person wasn’t very good at financial analytics and all that, because at heart, they were more of a salesperson so they were too optimistic, they weren’t analytical enough. So sometime in a couple of cases I’ve seen where we’ve been able to move people so that we can help people, you can’t really change people in my experience, so it’s better to understand who you are starting with yourself, and then the people that you’re dealing with are, and then find the right fit for them if you can, and if you can’t. The thing that surprised me and I unfortunately have had the necessity to hire more people than I would like in the course of my career. And I agonized over it although my husband says, the minute you like hiring people, that’s probably the underboss you know that’s true, fantastic training, I would enjoy that our world. When sometimes people are happy, Sometimes people are just, they’re unhappy, and they’re unwilling to admit it, or, you know, sometimes we think if we fire somebody to the end of their life, and I find that people will either. Interestingly remain friends with and have gone on to bigger and better things because sometimes it’s just the wrong things I think we have assumptions about what’s good and what’s bad and what’s right and I think it’s way more situational than that, there isn’t an easy, like an answer and I would never fire somebody based on a profile, but it’s about performance, and then the other thing to look at is if somebody is really struggling to keep up with where you are right now that you have, you have to succeed, you know, it’s, it’s looking at the good of the company versus the individual. As far as the choices. Well, if they’re letting everybody else down. I would have to look at okay well there are hundreds of people or 1000s of people who are responsible for I can’t allow one person to in their inability to cause us to fail.

Mike Malatesta  16:22

Yeah, I guess, I guess, as you were talking I was thinking, you know, obviously you can’t make someone change I know we’ve, we’ve tried that as human beings, forever and it just is very very difficult. And it’s also it’s also okay if someone doesn’t want to change it just, I mean, that, that doesn’t mean that what they’re doing is bad, just means it’s not right for us, is that what that’s kind of what you’re saying right so that. Yeah. So I think we’re where so many people run into problems with this and this is where it takes courage as a leader, I think I want to see what you think, but it’s when you made that determination that the person isn’t willing to, you’re not is not willing or does doesn’t believe. Yeah, whatever. And we still go, Ah, I just give it more time and I think I’ll be able to change them over time or, or they’re just so valuable, like maybe the head of sales but they’re just so valuable production wise that I can’t not have them. I know that. Yeah, we start we start rationalizing things right because sitting down and saying I’m sorry, and then whatever comes after that is this maybe harder, it’s certainly harder in the moment than keeping them but long term it’s, it’s a lot of pain to keep a person like that for both of you. Yeah, give it away.


We have all these CEOs and ask people, whoever feels like they have fired somebody too soon.

Mike Malatesta  17:55

Right. No. Yeah.


It just


doesn’t happen. You know, most times we wait too long. But I always do believe, you give people a chance I mean, it’s also sometimes we’ll be at fault can we set expectations. So I will always examine myself and say well do they know what we need them to do. And, you know, are we setting goals and they understand exactly what’s expected, and then it’s up to them if they can’t or won’t that I start to feel a little bit better about the decision that we’re more comfortable with the decision. I always will I get people probably too many chances. I guess I’d rather give me too many chances but not enough, but I probably still err on the side of waiting too long, like most people do because it’s, it’s a human being. Yeah and you worry that it affects their family and their lives and, you know, especially during COVID times I think that’s probably one of the hardest things for all of my clients is, we had to make cuts, just to stay alive, and that impacted a lot of people that have very difficult time and yet if we hadn’t, we might not have a job for them to come back to simple, it was a Sophie’s Choice kind of situation I think for

Mike Malatesta  19:08

many of us, yeah sure you got to, you have to put the company first in those situations, even though it doesn’t feel like that’s maybe the right thing to do, you know, um, but I’m also complicating things in, in the pandemic or, you know, even if the company’s doing okay people’s lives personally changed a lot, their kids or it’s, you know, homeschooled and maybe their spouses in his home as well you know trying to, they’re all trying to, like adapt to this new thing with a lot of responsibilities that other people would take, generally speaking, right, and so you’re trying to do your job and do all these things so it’s difficult, you, you mentioned when you were talking about the dilemma of your head of sales that you’re kind of asking yourself the question, like who am I, who are you, you know, and I wondered how many times you’ve had to ask yourself that question as a leader when there’s been a decision to be made. That may or may not be about a person but you know it’s a, it’s a, you know there’s a gray area that you could probably, you know, walk your way into for example that may or may not feel like it’s exactly right but it doesn’t feel exactly wrong either you know that kind of thing.


Yeah, I’ve definitely had several where I had to go back to that going forward what I feel good and how would I feel about the decision one way or another, even if nobody, but we do. Yeah. You know I I’ve had three times where I knew I could get fired from the decision that I made, but it had to be it was the right decision for me, that might not be true you never regretted those decisions. I think you just at the end of the day, have to live with yourself. And the one thing that we have our entire lives is our reputation. And, you know. Am I perfect No.




do I try to do things so that I could have I’ve always done things in a way that I feel good about myself. To myself. That’s sort of my, my composite is, is that something I would be proud of. Is it or is it something that would be ashamed. And even at the end I kind of curious when Windows 10 I can get fired for this but this is what I think I have to do and he’s, he’s been very supportive so I think having a support system around you that that you’re where your values are the same is really an important part to any relationship, having the people around you that you trust. So I think there’s a lot to be said for having a team that you trust, and having the whole support that you trust as well,

Mike Malatesta  21:50

which if so would you be willing to talk about one of those three examples to give us a flavor for whatever.


Well, one of them was, I was told to pyres of money. And if there was, there was a bit of a business, there was a business reason for it, it was a cosmetic thing. So, it wasn’t performance related, but we had an office of another company now, an office in Canada and we will cost cutting, but closed down in the office. So the guy had just had a brand new baby and the baby had a congenital heart defect. And it was going to be the kind of thing that was going to require all kinds of surgery and all kinds of difficulty. And so I just losing your job and losing the insurance was just a radical impact, and it, he was, it wasn’t anything about performance. So I came up with a way to save the money doing something different. First time is recording can can just my hair, my boss,


really tough individual Okay.


When I walked in and said hi, very sorry to hear these, you know, extenuating circumstances and come up with the money that we need to say, but I cannot hire this person and if that means you have to fire me and I’m really sorry but I just feel good about this, and much, my shop was woman, she actually said Oh, like that of course. And still, it changed our relationship forever so we didn’t have it was brand new relationship, and come up with the money of course that’s right. Boy, a big sigh of relief and move forward. Another time I found that there was somebody higher up the maintenance asked me to do something that was bordering on illegal. And so I actually went to our legal counsel, and having legal counsel and I felt very mixed about that because I didn’t know what that was going to do to my longevity, but it’s just, you know, obviously it doesn’t happen every day, thank goodness, and I don’t regret, you know, taking the chance to do the call.

Mike Malatesta  24:05

Sure, where you would have if, if, if you hadn’t, you know, kind of, yeah, you always be thinking about it. So, another thing that we have in common. Before we get to IPO is Portage Indiana to recall. Yeah, so, um, so you, you grew up in Portage, I believe, and I actually, in my first business I had a location in Portage, Indiana. Yes, I did so. So let’s go, let’s talk about Portage Indiana and how Portage Indiana. You know led you ultimately, I mean, you started with when I became a CEO, but there’s a whole thing before that, that’s me very well have started in Portage Indiana so why don’t we talk about that.


Well I, I basically grew up and I can’t wait to hear what your business was, but Portage Indiana as, you know, outside of Chicago about an hour kind of long the lake, but the majority of the industry when I was growing up with, with the steel mills, and that’s where my dad worked as well. And so, it was the high school that I went to I, most of the kids ended up going to the steel mill, and I remember when I graduated, no with my four year degree. My first job was making happen but I would have made if I still know the Secretary or something, but I just knew that was never my path, and in high school I have to went back for my 20 year reunion, and I had had such a different life than most of my friends there. In that you had to say. The biggest thing you’ve done in 20 years and for someone that looks like going to Chicago or learning to knit or. And I just felt like my, I never felt like I really belong there. Yeah, I had, I don’t I didn’t actually do dreams but I just was a bit of an oddball I was smart, and it might be ended up of high school, two of my girlfriends and I ended up running all the clubs in that part of it only went to prom once I wasn’t like a big Gator. One of the boys that my 20 year reunion typically we are kind of intimidated by you.

Mike Malatesta  26:23

Oh is that right


is a skinny little thing. I didn’t feel intimidating but I guess maybe because I was in school, so I didn’t really feel like my life was never going to be to stay there and I didn’t know what my life was going to be but I just, I never saw myself, you know, living there forever, so it was, I haven’t good life. Pretty cold laughs No of course not so great, but I had friends. My friends were kind of the geeks, you know I’ll pretty much all my friends ended up leaving and going someplace else for college, and most of us did not stay in the area. So that was my growing up years, but it was, it was a good place we had, you know, like my friends would come and play their guitars in our garage and my house was the house that everybody would come to my house to train so I’m friends with yet today, but, you know, not, not wasn’t replaced I set stuff up staying forever.

Mike Malatesta  27:22

Sure. And what. So, so we, we had a waste, industrial waste processing facility on old Porter road it’s still there actually old Porter road off of off road. Okay. Yeah, it gets pretty dark down there. Yeah, I suppose. There’s a, I don’t know there’s a, there’s a, like a mobile home park down there I don’t know if that was there at the time but yeah that’s, I imagine. Yeah I imagined back in high school that had to be, yeah. Okay, good to know. Good to know. But, so it, and you probably don’t get that very often having to exit unless you’re going to reunion having a portage Indiana connection so there you go. You stayed in Indiana for college, as I recall. And then, and then you did something really interesting. You. Well, Utah, you You mean, you decided you weren’t going to stay in Indiana, and that led you were


to Los Angeles, all people who leave me know my brother was out here and I only came up to visit him when I had like 40 days of my carving stuck in snow and so I came out to come to this weather, and I decided that I was going to move to California, in that moment, and I started, I was working on my MBA at night, and I started in somebody serendipitously told me at a wedding. I said well how do I, you know, what should I do and how to avoid duties at all, don’t pay for your own MBA. She said big companies will do that. So I went this way pre internet I went to the library that scattered and force and started looking for big companies in Los Angeles, and cold call and said I’m looking for your director of management training, and literally that’s how I ended up finding my first job at carnation, I got in touch with a fellow who was the head of management training, and so I knew they had a program, and one thing led to another first he didn’t want to talk to me I kind of talked him into to see me for 15 minutes, and then I came out again to visit my brother on a spring break and in the course of the week I landed a job with them, and moved here, and never looked back. I finished my degree at USC at night while I worked, they paid for it. So she was right. And it was, it was, that was another turning point that’s why I said in the beginning it’s hard to know where the turning points. So moving here and you know going into business and starting out, was it was like starting a whole new life which I’ve never left so I guess I like it pretty much.

Mike Malatesta  30:19

And so, I love this story I mean you just go out there and you start picking up the phone, I mean at that time it was probably difficult. So, that was like 19, but 90 this before Lockton, yes. So in a sense, yeah so it wasn’t like you could, you know find contacts, easily or phone numbers easily you had to go through somebody I suppose right when you’re like a gatekeeper of some sort of


reception desk and ask them who their head of management training was and then somehow get connected to there so I guess I was a little resourceful. Yeah, okay. Sometimes I look at it and I was I just stupid just naive to think that this could work.

Mike Malatesta  31:07

Sounds like you weren’t. Sounds like now. So yeah, that’s what matters. So when you got into carnation in a management training because it does that, so that’s how I started in a management training program but the company that I started with. It was kind of new, they didn’t really have a management training program actually built out they had an idea that they wanted to have a management training program. What was your experience like and where did that lead.


It was just the opposite. Okay. Management Training Program was superior. In fact I was getting my MBA at USC, and then like every Friday we met our management training classes that would bring in in those days, this is no longer done but the class of like 15 to 16 people, and I mean literally enough to have a class, and our management training was so good. We had just, you know, every kind of every aspect that you could imagine. And I learned as much in that management training I also think I learned a lot, because when you’re working and doing a degree, It’s very different, because, you know somebody is telling you something in a classroom and then you’re going to work the next day, and you’re seeing sort of, well, that might sound good in theory but that doesn’t really work that way. So I think it was just the combination of all of it I don’t know how I have the time to do it. I can remember, you know, getting up at 430 in the morning to study and studying during my lunch breaks and then it was, when I look back I was on a softball team. I was having a social life, and I don’t know, I don’t know how I managed to do it but I think it was another one of those periods where I was just so happy. It was, I loved. I LOVE MY LIFE and I was very very happy and fulfilled, and I’ve been lucky enough, I have to say I have not liked anything that I’ve done. I’ve always found something. And I think that’s for your listeners, I think probably one of the more important things is to be able to, If you can connect with what you’re doing and feel good about it, and whatever that means. I mean, you could feel good about your business and the way it’s helping people have better lives. I mean it doesn’t have to be a sexy business, I mean I was working on dogs in the day. It was just all the learning that was going on in the pure dome and the people that I was learning from it was just a really high growth period for me.

Mike Malatesta  33:26

And you mentioned earlier that you love products and I made a note of that because as an you just sort of alluded to it but it’s so it doesn’t have to be a sexy product or whatever but I guess I want to get into your mindset, a little bit about, you know you’ve been, you mentioned Mattel carnation Teleflora I think is the company you might have been talking about at the beginning, Universal Studios Vivendi you so you’ve been in, and who knows maybe others all of these different industries, with different products, and I’m wondering where your love of products, came from, and what it actually, like, how do you, how does it apply over all of these different these different businesses, like how do you keep is something you just have an ongoing passion for and for lots of products or why I’m just curious how that goes.


Pride of Creation.




As crazy as this sounds when I walk through a grocery store, still sometimes walk past products, like oh my god feeder products and although they’ve added this they’ve added that. For years I’ve stopped now. Thank God, but I would actually face the CANS properly.

Mike Malatesta  34:45

You’d arrange it.


But it’s true, always want to make sure it looks good, for nobody to me. It’s a little craziness, but it’s almost like it’s not motherhood, but the Pride of Creation, and when you actually see something that you’ve worked on how much, there’s, there’s,


there’s a pride in that.


That people for me. It’s not I just don’t want to see it there I want to see that it’s successful and be like it and I’m meeting some sort of a need. And I’ve actually grown where it’s not even just products anymore now I think services. I think it’s, it’s the creation of a creator like there’s some people who were meant to be looked at The Wolf of Wall Street are some of the people who were really really good at ripping things apart and taking every last penny out of it. That is just not me. I am a creator, I love to help. I love it when I love working with growth stage companies and people who are trying to be more than they are today. And the entrepreneur, entrepreneurs, and I love seeing their businesses grow. I love seeing them, companies employ more people I’m a real, I am a real capitalist and I believe that you can do good through business, and I, I, I’ve expanded my love of. I’m certainly started with products and any product I can likely find less success, but now I find, I’ve been helping people. Some of my clients market products businesses, and I’m finding, maybe my new or evolved as I grow older, secret sauce is growth. Growth whether it’s up their team’s growth of their businesses, if I can see that what I’m how I’m helping them is leading to their growth. That’s kind of my, that’s my new element that makes me the most happy.

Mike Malatesta  36:37

Okay. I like that that’s a nice evolution. And you don’t have to straighten those cans either during your during your products career is there a favorite, that you had that you’re willing to talk about.


That’s a very good question. And a lot of great products of Mattel I get some of the early Barbies that were sort of female empowerment Barbies because Barbie certainly wasn’t something that I loved. I liked the first Dr Barbie and the first Barbie and those kinds of things. So setting enrollment, little girls, this morning when I fell in line with, and I did a line, it didn’t last long, but I did a line called Angel Bunny, where we had pediatricians and we had, you know, some science behind the products. It’s fun to see just some of the silly products like rainbow grime and things that were just popular culture products. When I was in Imaginarium. I ran a retailer, which we haven’t discussed yet. Interested another chapter in my life. And we get high end educational toys, and there we came up with 200 private label products, and I was a mom, three to five year old kids buy them. And it was the kind of products I wanted to buy so it was a craft kit and had absolutely everything you needed because, you know, I’d start things with my kids and then halfway through Oh, we don’t have this little thing and you couldn’t finish. So, I loved doing the products that I felt like what products I would like I would like to buy for my own kids, and had more than many of our mental products didn’t have the educational value. So I liked working on products that I felt were, had more of a redeeming value so I loved all of those that was, that was a lot of fun and a lot of girls, and the universal, it was, it was happening that that was kind of a different kind of fun. The products there obviously we were working with film and then translating that into products and it was taking things like the classic property like Curious George, and turning that into. I don’t know how many different products, even before we had our film where Jurassic Park was interesting because that was all such a huge you know $500 million products alone, a billion dollars with the products and looking at how you could take somebody different manufacturers and create a story so that it looked like everything came from the same place. So that was just, it was is a different I guess what keeps me going is new challenges. So each one of these were kind of different and new challenges. So, it’s hard to have one child that you like better than the others, but those are a few.

Mike Malatesta  39:18

Okay, fair enough. Imaginarium so we didn’t talk about that. So, first of all I want to make sure I understand 200 private label products so you had stores that you were making your own products for, is that right, okay,


right in, we have the architects did a great job they had a regular adult door within this little envelope with everything from things I think by now. We sold everything from, we did some of the first we had computer software for kids we had computer stations set up in the stores themselves. We had a whole book area. We had real trading tables and you know whenever we literally had a lot of try and buy kinds of things so it was kind of like an it was, It was experiential shopping before that word existed. Excellent. I will say customer service. We trained all of our sales associates and a lot of them or teachers and people, students, we train them to be able to answer the question if somebody came in and said okay I have a three year old I don’t know anything about three year olds I’m on my way to my niece’s birthday party what’s appropriate, so we would, we actually taught our sales people to know the answers to that gift wrapped and did a lot of special service. That just made we tried to make it easy, again, based on a little bit some of the things I needed, which were you know you’re on the way to the birthday party on a Saturday, you got to get something you got to get it quick and you want it to look messy.

Mike Malatesta  40:59

And what was the, the challenge or the difference moving from, you know some of your other roles to that retail environment as you said, because I’m imagining now retail gets is. Maybe it was, I don’t know what what the timeframe was on that but obviously retail has been, you know, a lot of retail has been really hit significantly by the pandemic. But what was it like for you, I mean retail is a tough every business is tough but you hear retail is tough, all the time, like a supermarket, really tough business. Yeah.


When is the toughest of all, because it’s 365 days a year. These days, and it’s for that business in particular weekend and majority of our business, six weeks out of the year. Now, but you know Christmas and Christmas, and that’s where the majority of the buying is done and when I became an avid watcher of the Weather Channel because of that storm


could hurt.


That was devastating. So I think I underestimated the challenges of how hard retail is going to be. I also underestimated the challenges, working with veterans with venture capital back. So that was another challenge, and I was, I was very naive in locking into that one. And, ultimately, to make a long story short we sold Toys R Us, but it was not it was not a happy ending. In my mind,


okay, because they


could never have the kind of service that we had, they could never do some of the things that made him special basically had to go away. And that broke my heart.

Mike Malatesta  42:43

I see. Right, so, yeah, yeah, yeah right, yeah to fit into a model that was way different, right to an order


of you’re kind of heartbreaks. It was like what was right in the business. And unfortunately that was right for the business but it was, it was a very sad. Sad decision. So, I wish I could have, I wish I could have fixed that, in ways that were not possible.

Mike Malatesta  43:13

So when you joined was the companies to sort of basically still a startup you mentioned that it was venture capital own so I’m wondering what the trajectory was


during my time there, okay. So, it was we got some in Chicago, we had some big monitor and diagnose my

Mike Malatesta  43:35

field, is that what it’s called. Yeah,


there we were pregnant, started out in San Francisco so we were primarily west coast, but we could go back as far as we used to have Bruce Springsteen came in, and shopped in our store in New Jersey for is

Mike Malatesta  43:52

that right.


Yeah, so we have two East Coast stores. Mid Atlantic, never in the south but it was a great concept and you know now all of that kind of stuff has gone online, you know that he kind of most of that niche business is more online now even Toys R Us hasn’t made it so it’s really changed retail is really the Internet has really


opened especially with COVID I


think it’s going to have to go more experiential, the ones that are going to come back. It’s going to be required that it’s more than just buying something, because it’s so much easier not to go someplace to buy something.

Mike Malatesta  44:34

Yeah, there’s got to be a part of the purchase that you can’t buy somewhere else.


Right. Yeah,


maybe some apparel it’s just easier to be able to try it on and return things but other than that, it’s just so much easier, anybody who wasn’t a, an online shopper now is.

Mike Malatesta  44:52

Yeah, well, sure, yeah. So when you, when you decided to step away from being a CEO, did you have, what was your game plan, but


no I started up I had a strategy agency for about 12 years, and I really liked that. And through that I started doing coaching my whole life was an unintentional plan. So I kind of evolved in the consulting is nice with a couple of my projects that were like, You know what I really like this relationship and you’re really helping me in more ways than one. And can we just continue and so, like, I was a consultant of the first place by not intention. I started doing a culture, and one thing led to another and through YPO, I was at an event, and other wipr Chris Larkins came up to me and we were just talking about our backgrounds and I told him, he said oh my god you have the perfect background and I said what he said, Well, I’m part of this group called CEO coaching with all those fair amount of those coaches I think probably 20 or 30% are YPO leaders, and




perfect, because you’ve got so many of the, you know you have. It’s a requirement that you run a company that you’ve had a successful exit, And that that’s like the, the table stakes. And I said well I really like doing the coaching, so that sounds interesting. So one thing led to another and I found I really, I love you know we’ve got like 40 coaches now so I’m a people person, so I love having the camaraderie of other people who are doing the same thing. I’m a lifelong learner, so we are constantly pushing ourselves to learn and do better. There’s almost a six month apprentice period where you, even though we’ve all been CEOs, we shadow each other because there’s an art to coaching, that’s different than consulting, And there’s a part of it that it’s like other consulting, where you’re sharing experiences sort of sharing the answers, the coaching is really helping people it’s like a forum where we ask each other questions and don’t give the answers. So you ask questions to help people come to their own answers. And that’s really the, that’s the long term value for tables they give themselves as they learn. And then the third bit is a little bit of almost therapy where you get to know people’s personal lives, and their issues and their other things that, you know, impact what they’re doing in their business life. But we look at our coaching as we coach the whole business so many times. In addition to the CEO will coach CEO or sale, whatever, wherever, wherever it’s needed, and I couldn’t be happier. It’s like, I have a lot of it you can tell I like variety so I have a lot of variety. And every day is something new, and I like the camaraderie of having other people who are sharing the experience. So it’s from my point in life right now, it’s absolutely perfect for the person who’s going to retire. So this is just it’s been with COVID Oh my goodness, not having to leave we do most things on Zoom, when life gets back to normal, we’ll go back to we do like quarterly or annual planning sessions in person, but most of our calls are by so many ways so it’s proven to be an end with all of the different things that I’ve done the thing that’s been the most useful is this year everybody’s had to pivot, everybody one way, even if, even if you’re doing the same business things about a pitch change is because I’ve done so many things I find what I’m good at different things. This crazy life that I’ve had.

Mike Malatesta  48:33

Yeah, right and good point there because you know if your business is like going down during this, or if it’s going up like a rocket during this is still, it’s, it isn’t like like you pick out a pivot if you’re going down but if you’re going up, you’re scaling up really fast, faster than you ever imagined you would. There’s a lot that goes into actually making that work, It’s not just like business as usual like right because demand is there, it has to be met. You’re absolutely right. Yeah,


sailing towards the moon. It just has a whole different set of cameras and sensors, people things happen in where you just have to be average.

Mike Malatesta  49:17

So one of the things I want to make sure people understand about you. And this SEO coaching internationals coaches are very common title now that a lot of people, attached to themselves so there’s a lot of coaches, it’s a, it’s a more than probably one of the fastest growing job titles, I’d say. Right right right. But I want to. So I want to I want to, you know distinguish you from a lot of those others and so, so your organization is coaching leaders that have a combined $33 billion in annual revenue, have had over a billion dollars in value of exits having sold businesses, and they’re growing year over year. On the profit side at a very significant clip much higher than, than others so it’s not so I wanted to just put some facts or that I found on the website of course but I around the type of coaching that you’re doing versus what I see a lot of people who say their coaches, maybe are in a different ballpark, I guess so. Having started there, Cynthia, what, who are the people that you are typically working with, if there is a technical and what are the challenges that they come to you with that you then, you know, sort of massage who this 1/3 1/3 1/3 kind of approach to get them where they either want to be or think they should be or what what I’m looking for commonalities and then I want to just get some free consulting on how you attack, you know attack there, help them achieve their goal. So


we always start with the CEO, CFO or head of sales but they always start to feel they are first in contact generally. And so that’s where it starts, and most of the CEOs who come to us, they look at some of the things you saw on the website, you know, if a company’s been with us for two to three years, their evidence up by 60% They’re, they’re growing in two times the rate of national average. So, we’re all about growth, and so most people see that and say, Well, I know how to do what I’ve been doing, and within going along with PepsiCo and along the pipeline, but I know what to grow bigger, I want to build big, Our founder Mark Moses has written a book about thinking big, and that’s sort of our model, so I wouldn’t say the one thing that is a common thing for all of us is how do we help our clients make bigger. And because that’s what we that’s what we add to the party is thinking bigger, not just thinking, but then how do we break it down, we have a whole process whose whole system where you know you’ll set an annual goal and you break it down into quarterly goals and we’ve worked with a team who’s not just the person, and keep reaching those goals, and revising and move, and holding people accountable and putting dates and times and so there’s a real process to prod, there are two parts that are the ones the process that we use and the other is the people element. So, evaluate the people understand that your team has gaps. And so, If you get those two things right, you succeed. If you can get a good process in place and understand what’s triggering the flywheel in your business, or what can or what adjustments you need to make the most people come to us with a growth mindset. If they’re happy with what it is that’s not usually our client, it gets there, therapists, sometimes. The second thing could be when somebody really does not know what to do next, they’ve gotten to a point in their life. I don’t know I’m independent. And I really need to relook at. And so that’s the other thing we often help do is really look at what are your core competencies, if you’re not going to do this, what else could you do, how do you pivot this business. And it’s been interesting, we’ve had some clients who have absolutely pivoted and are more successful than they were before the pandemic. So it’s not a slam surfing.

Mike Malatesta  53:44

Okay. And do they, and so I guess I’m thinking about engagement. So I come to you and I want to have a growth mindset I want to get bigger, but I’m maybe I’m not focused right maybe that’s because I’m an entrepreneur, let’s say I’m like I’m always going in 100, different directions I how do I, maybe that’s the part of the therapist part where you have to sort of, you know, say, Is this what you really want, because if this is what you really want, we need to, you know, focus so that you stay engaged and so everybody on the team stays engaged, and I’m just


what you described is, is, is not unusual, and a lot of entrepreneurs, a lot of entrepreneurs have a you know, add or you know, quick to jump from one to the next, but that’s where sort of the planning process, so you’re not going to change you’re going to jump from one thing to the next. But if your team has a plan that they’re executing on, and you’ve agreed that those are the priorities. And then, if anybody including you wants to put something else in, you know, we’ll kind of say okay, it really is that more important than getting this thing done. The first thing that you agreed to, and sometimes it is sometimes you will have to shift, and other times it helps you. I think we can help people stay away from shiny objects a bit or at least remind themselves that is that shiny object better than what we’re working on right now.

Mike Malatesta  55:10

Yeah, right. Okay. Good point. Good point. Well that’s right and that’s, yeah that’s why they come because they are, you know, if you want to accomplish something you got to have a system and a process for it and you have to follow it right. I mean that’s


the first thing we do is we get a profile on the person, but we don’t use Myers Briggs we use disk. Okay, understand who we’re dealing with right away. So that, and I’m always happy to share my profile with anybody because it helps in any relationship to understand each other. And so if, if we both know that shiny object is the issue and if that’s something you want to work on. I mean, you’re not going to change should not get distracted but you could change to not react every single time. And think about it. So, you know, we look for incremental change. I think we will do change but not like, I just don’t think my earlier degrees I have one in psychology and you’re just you, fundamentally, are who we are. And you can understand yourself better and learn how to make life work better for yourself but dramatic change. It’s not,

Mike Malatesta  56:22

you’re probably really out I’m wondering when you first started. And you, you did acknowledge you know you always want to find other people that, you know, you can work with that can do things better than you that kind of thing, but I’m wondering how you, you know, when you were first getting started as a coach sort of resisted the temptation to say do this, this.




We can see, okay, here’s the answer. But that’s not the right thing to do. And so it’s a little bit of a balance sometimes you do say, you know, I’ve seen this movie before and it doesn’t end well and let me tell you what my



Mike Malatesta  57:03

is. Yeah.


But the real value and the artistry of coaching is helping somebody learn how to do that in themselves, like helping them learn how to come to the conclusions themselves. And there’s an art to asking questions, What I was thinking I had to learn and I’m still learning is the art of asking the right question. And because it’s gonna work a lot better. It’s one of the if I give you the answer it’s another thing and become to yourself, because then it’s in you, and then it’s you’re doing what what’s right for you, right, it’s

Mike Malatesta  57:38

mine, it’s yours. Yeah, it’s property Yeah,


you’re right up many of us sort of jumped to the end and see it, but we have to get through the process to understand that yourself. And so, that’s the part that I think every single one of us has had to learn. Okay, there’s nobody who’s come in. It’s very different being a CEO than coaching the CEO.

Mike Malatesta  58:02

Yeah, I’m thinking you may need a coach inside of your organization to make sure that all of you focus on being coaches instead of being CEOs because it’s, that’s exactly what we do. Okay.


And then, you know we have somebody who shadows us in the beginning and says, Okay, here’s what you did right here’s how you could have done that better. No, we do that

Mike Malatesta  58:24

ourselves. Okay, makes sense. Makes sense.


If you want to keep getting better, I just have become a huge fan of coaching, and if you think of it. Anything you want to get better at. If you are open to getting that kind of expertise and help. You’re going to get better. There’s a reason, all these athletes have coaches. Right, yeah, Bill Gates has a coach I mean he’s one of the biggest proponents that head of Google, they’re just all kinds of people who can look down business people have realized there’s no reason they can’t help themselves get better by having that outside perspective.

Mike Malatesta  59:02

Yeah they was a Tim Cook there wrote the book about Bill, I can’t remember Bill’s last night. Yeah Bill Campbell. trillion dollar coach, right, yeah yeah yeah yeah I read that


book and it just made my heart sing because I can just imagine how gratifying it was to, to build Cameron who was actually one of my YPO girlfriends Mary Baker, actually. Bill Campbell, who was coaching, she was at Intel at the time and he is the Godfather one of her kids. So she has handled it was an amazing man, But got paid really throughout Silicon Valley, that’s what they call him the trillion dollar coach.

Mike Malatesta  59:48

He was a great, great book the trillion dollar coach, because this guy had been a CEO, multiple CEOs his IRA, CEO positions of their call. But it became a coach and what was unique about him as he didn’t take any fee to be a coach to Steve Jobs and to, you know Tim Cook and two other Turgay and lots of, lots of people. And he never took a fee because he, he was like he couldn’t. I can’t be honest with you if you’re paying me right it’s like you’re not so not what you’re, that’s not what I’m here for something, I’m paraphrasing in this book, read the book, it’s a great book. I learned a ton from it. Yes, right, right, Right, well everybody. Yeah, but, but, I’m sorry. Oh, that’s fine.


He told me an interesting story about her and him. He said, she said she would have her calls with him, and he would just always talk about her personal life, you know, how are the kids doing how’s this how’s that finally one day she said, Aren’t you supposed to be my business coach, why are you always talking about my kids and my family. He says, Well, I see your results, I know you’re doing fine. So I want to find out about the whole person. That’s. And he was that, I mean he coached little kids. He was literally a coach to

Mike Malatesta  1:01:15

write football coach, I remember. Yeah.


So that’s what I would I would aspire to be, I don’t care about the money, but I would aspire to be somebody who could influence and help as many people as he did.

Mike Malatesta  1:01:28

And he certainly puts a big exclamation point on what you had said that everybody needs a coach, I mean the these top people that you think know everything because they’re running these huge organizations. They, they’re lost sometimes just like all of us are, don’t know what to do or need.


My reason for joining my mailing list for the forum’s which is individual groups, everybody else is sort of in the same shoes in that that I realized in retrospect, kind of serve my needs. If I’d known about coaching that would have been even better. But so I think why PBL does it to a degree with our forums, but if you want somebody to work on your specific business, this is just that much better.


I agree,


my person.

Mike Malatesta  1:02:14

I totally agree. I totally agree. Well, Cynthia. This has been so much fun. Thank you so much for being on the show and sharing your stories and your experiences, your wisdom. And congratulations on your career and, you know who New Port is Girl look at you know, people.


That’s great to meet you. Well, it’s

Mike Malatesta  1:02:39

been my pleasure to have you on the show today. Thanks for sharing how should people get ahold of you if they want to connect


your computer.

Mike Malatesta  1:02:50

Okay, simple as that. I have that in the show notes too.


Thank you.

Mike Malatesta  1:02:57

Okay. Well, thanks, I hope that went okay for you.


I was gonna ask you that. Right, yeah, a lot more of these than I.

Mike Malatesta  1:03:07

Yeah it was great. Super. Yeah,


I thought of one more person I want to refer to you. Okay. His name is Andy Brown, and he is in one of these businesses that I think would be timely and interesting to your listeners. He is in the business of air purifiers. They have got I mean their businesses going through the roof. And he’s actually got a really really high quality product that they’re selling up and that they’re doing business with schools and restaurants and, and the subject with him would be, you know, how do you deal with our apartment would be, you know how you deal with it and the interesting thing is this business has been around for 15 years, and they really have the sciences and everything behind it. There are multiple other players in the category, there’s no real category. Right now, I would not be surprised the Andy King would be useless even at one point and he’s got a good background himself, okay, but I would not be surprised if they are the ones who are able to pull off getting some, some brand recognition. It’s just the business is going through the roof. And I think that he’s starting to look at how does he build a brand. In addition to, you know, just the financial returns because they actually have a very good product, and he wouldn’t be, he wouldn’t be interesting just to hear how did you know how to have what do you do when you have a tiger relative. Yeah okay


good analogy Yeah, sure.


It’s just, it’s astounding, and it started off and the person that started off with people who had allergies and asthma and they are very rare. They have like a lifetime guarantee, you can return your unit after 20 years and they will replace it so that they built that he calls that the Sherman tanks, but they build a really exceptional quality product and it looks nice. And then last year when the, the institution started meeting products, he started, I think he’s in 30,000 schools. By the end of this year that could be 300,000 schools so they’re just kind of rampant growth path so I will email you this information.

Mike Malatesta  1:05:23

I’ll do my best. Okay, fabulous. Yeah, thank you. Yeah.


Sarah story is so interesting because of the term that she took with her. Doing the female led businesses with startups in Africa, yeah. And then she started the beginning of her story, she and her husband were careworkers, I don’t even know where somewhere, they met he’s, he’s British, and they met, doing good, good deeds, good work. And then through that they learned. The thing that came up with the idea of doing very high end glamping there outside most of our national parks, and it’s about the price of a nice hotel, but it’s really still thinking of going, I think it I think it’s going to more than many other things, it’s going to rebound because you have your own project template you’ve become a real bet and you ever move out to them which for me is my it might be a few others around you so as far as safety goes and everybody’s worried about coming back. And I asked her, and she said they have they actually are coming back in a big way, but she had, I don’t know how much they’ll tell you, but she had a tale of us, selling out venture capitals and capitalists who that are private. Private equity, private equity, who said that they were with her growth plan, and we’re going to support it and then within a year, they bring it. And so she ended up leaving. And so that part of the story is not so happy but she ended up getting enough money out of it for the rest of her life, and is now doing something that she was very passionate about so I think it’s a happy ending, but he wasn’t. She’s just a great distance

Mike Malatesta  1:07:20

to meeting her, I appreciate the introduction, and all of them.


I just figured variety is good.

Mike Malatesta  1:07:27

Yeah, for sure.


You got to get some really interesting stories. We’ll get it that way. Got it.

Mike Malatesta  1:07:34

All right, well thank you. Okay, yeah. All right, thanks. Thanks, Cynthia. Alright, see you later. Bye.

Mike Malatesta

Mike Malatesta

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I help entrepreneurs get unstuck, take back their power, achieve their life objectives, and create the futures they want.

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