Episode 37 - Fashioning a Life of Passion and Purpose with Designer Cynthia Rowley

podcast Nov 11, 2021


Today on the podcast we have an amazing conversation with a truly inspiring guest to share with you! Fashion designer, business owner, and author. Cynthia Rowley has built an enviable career and life through hard work and dedication to her passion and practice. In our chat, we get to hear about the bigger picture and some of the finer details too. Cynthia talks about her early attraction to fashion, and desire to express herself in ways that she did not see in her small hometown in Illinois. We also get to discuss staying on the edge of fear and uncertainty, and why it is so vital to continue to explore the unknown. One of the main themes that comes through in this conversation, and in all of Cynthia's initiatives, is her authentic involvement and commitment to her brand and work; for her, the business has always been about more than just making money! So, to hear it all and catch a glimpse of a real-life unicorn, be sure to listen in with us!

Key Points From This Episode:

  • An introduction to today’s guest, Cynthia Rowley, and her background in fashion.
  • Cynthia's childhood years in Illinois and her early trend towards mismatched fashion and creativity.
  • Applying to art school and the move to New York after college.
  • The aspirations of freedom and creativity that Cynthia had on arrival in New York.
  • Growth in her company and the support that Cynthia received from her parents.
  • The pivot that Cynthia and her company made away from stocking wholesalers.
  • Growing into the role and identity of a designer.
  • Cynthia's experiences of motherhood and how this impacted her life's trajectory.
  • The importance that Cynthia places on living mindfully and in the present!
  • Unpacking Cynthia's decision to use herself as the name and face of her brand.
  • Expanding into authorship and a little about the books that Cynthia has written.
  • Creating your own rewards and celebrating personal wins on a daily basis.
  • Authentically bringing a vision to life through hard work and commitment.
  • How Cynthia has been able to balance her creative passion with business acumen.
  • Cynthia's passion for traveling and leaning into different experiences.
  • A message from Cynthia about the rewards of hard work!


“I was working as a bartender, as well as starting to make clothes. I abandoned everything for the unknown, no friends, and I just thought if I'm going to do this, I’ve got to go to New York, and I had no money and nowhere to live and I figured it out.” — @Cynthia_Rowley [0:06:48]

“I really just wanted this boundless platform for creativity, [it] was really always the motivation. It was never money. It was never fame.” — @Cynthia_Rowley [0:09:40]

“If it's not a 50/50 chance, it's going to be epic, or the end of my career, then maybe it's not worth doing.” — @Cynthia_Rowley [0:14:43]

“I think, living in the present is probably one of the most important things about running a company. You can never look back with any regrets. You can never rest on your laurels.” — @Cynthia_Rowley [0:24:28]

Links Mentioned in Today’s Episode:

Cynthia Rowley
Swell: A Girl's Guide to the Good Life
Cynthia Rowley on Twitter
Potential to Powerhouse
Tracy Holland on Instagram



[00:00:05] ANNOUNCER: Welcome to from Potential to Powerhouse: Success Secrets from Female Leaders, where female trailblazers share their journeys and the aha moments that made all the difference, with your host, serial entrepreneur and trailblazer herself, Tracy Holland.

[00:00:23] TH: Hi. This is Tracy Holland, your host of Potential to Powerhouse. Today, we have a true fashion entrepreneur powerhouse. We’re speaking to Cynthia Rowley, who began her fashion career while studying at the Art Institute of Chicago. After she graduated, she took a little bit of seed money that her grandmother had given her and moved to New York to start her fashion business. She has been on the forefront of fashion for decades. She has a brand that is in double-digit growth. She has self-funded this business and so is the single shareholder.

What I think is so interesting about Cynthia, is not only does she have this incredible fashion sense and design. I mean, she’s probably one of the most well-known designers for designing things that are outside of core fashion, for example, she’s the one who designed surf wear, and looked at wetsuits and decided to bring Cynthia Rowley designs to wetsuits. She did roller skates. She’s done all kind of categories that I would call adjacent to fashion and has brought her fashion sense to those categories and made them her own. She’s also a world traveler and loves to find exotic destinations. She’s a mother and she have a podcast with her daughter around wellness, health and mindfulness. She’s also a bestselling author and she’s appeared in numerous television shows, as both a judge and as a guest.

You’re going to enjoy this conversation. She’s so impressive. The thing that I enjoyed so much about her, not only her sense of spirit in herself, and connectivity to mindfulness, but I also just – she resonates and passion for what she loves aesthetically, which is where the true passion around her designs come from. But she also has an incredible sixth sense in business and has been able to build this empire for herself from nothing, and create a lifestyle and create a business that is her own, that she gets to wake up every morning and walk in the door and it feels like home. It represents her ethos. Even though it’s been a difficult road at times to self-fund and self-grow a business to this level, she’s been able to do so extremely successfully. Her thoughts on that are really most fascinating. Welcome Cynthia to the show.


[00:02:51] TH: TH: Yeah. Let’s kick off. If you would, I’d love to just get a sense of Cynthia as a little one. You were born in the Midwest, yes, in Ohio.

[00:03:01] CR: Illinois.

[00:03:02] TH: Oh, in Illinois. That’s right.

[00:03:05] CR: Illinois. Yeah.

[00:03:05] TH: I understand, you always love to be mismatched. You were a fashion – stepping into your fashion sense as a young woman. Is that right?

[00:03:14] CR: Well, I mean, I grew up in a really small town. There was no fashion influence there at all, really. It was preppy, if anything. I started sewing at age seven, making my own clothes. That was really my truest form of self-expression, and my outlet for to say, this is who I am. Some of the things, yes, did get a little crazy, mismatch. I think, that’s the time when you can really experiment.

[00:03:48] TH: Were your parents, were they more traditional in what they did for a living, or what was the home life like?

[00:03:55] CR: Well, my dad’s, well, now retired science teacher. He was a little Inspector Gadget thing, like Mr. Wizard or whatever, Nutty Professor. Then my mom is from a family of artists. She was at home when we were kids. My grandparents were both artists. My mom went to art school, too. It was natural for me to think I was going to have a creative – I mean, I just didn’t know any other way to be in life, like a store bought a birthday card. Never. Everything was like, you just made it. If you had an idea, you made it.

That was how I could manifest my imagination, too. Growing up in a small town where it’s called Barrington, but I call it the Borington, because there really wasn’t a lot to do. Great, beautiful town and great people in the town, but not a lot of engaging cultural activities. You had to make it up as you went along.

[00:05:15] TH: Yeah. You were enough of a passionate artist, that you applied to art school. Is that right?

[00:05:22] CR: Yeah. I ended up – I loved art, all through school, high school, and growing up and making clothes, and just making anything. Then, I went to the Art Institute in Chicago, where I graduated, I won the fellowship. That was not a lot of money. At the time, it seemed like a lot of money. It was enough for me to pack up a U-haul and drop to New York, and that’s what I did.

[00:05:55] TH: What were the parents thinking at that time? Were they in support? Or were you somewhat of that independent spirit already in which they thought she’s going to do what she’s going to do?

[00:06:07] CR: I mean, my parents have always been pretty, I would say, passively supportive. They never said don’t do that. They never said do that. If it was decided, if I had decided it, after the age of 18, of course, which is when they said you can do whatever you want when you’re 18. Definitely, I did. I saved up all my all my craziness for after 18. They just supported the idea, but I was leaving a town, where I knew I had friends and family and I was working as a bartender, as well as starting to make clothes.

I abandoned everything for the unknown, no friends, and I just thought if I’m going to do this, I got to go to New York, and I had no money and nowhere to live. I figured it out. That’s why I think, little by little, I think, and then we’re going to maybe talk about anything I would do differently, if I was going to go back. I don’t think I was prepared. I was very naive, which naiveté can be a plus, in a lot of ways, because you don’t know what you don’t know. It can really give you a fearlessness, I think.

Yeah, I guess that just fake it till you make it idea was that sums up my early years. Oh, I was saying, if I think I wasn’t – I didn’t really. I wasn’t prepared. I was ill-prepared. I didn’t really have the tools. I had the enthusiasm, and the passion, and the gusto and the energy to do it, but none other tools and no knowledge. Because I didn’t really learn it. I was so naive that I didn’t know there were factories that made things. I thought you just hired seamstresses. I didn’t know. I just didn’t know anything. That’s the one thing that I think I should have been – maybe a little more prepared. Now, obviously, it’s so much easier to get information and educate yourself in whatever you want to do. I mean, it’s a whole different time now. It’s definitely much better time to be such –

[00:08:38] TH: Oh, 100%. Yeah, completely. I agree. I mean, it’s like a time where you didn’t have the Internet, so you couldn’t start researching. It’s piecing things together, asking questions, stumbling. It’s like, following the breadcrumbs, I always say. When you rolled into New York, I can’t even imagine. You’re rolling into New York. Are you thinking at that point, “I want to be a fashion designer” or were you headed there, because ultimately, there was something you wanted to do in fashion, but you weren’t necessarily sure? Where were you at that stage?

[00:09:14] CR: Well, I started selling little boutiques in Chicago. I had the process a little bit, an understanding of the process, like make something, get an order, then make multiples. Then send an invoice and get paid. Simple as that. I kind of knew the process, but I of course, wanted it to be huge and important. I mean, I really just wanted this boundless platform for creativity was really, always the motivation. It was never money. It was never fame. It was always like, how can I have a vision and make it a reality and have the tools to do so on a daily basis over and over and over?

[00:10:03] TH: What blows me away, Cynthia, one of the things about you that just blew me away was that, I think, I understood that you raised $3,000, from your grandmother, who gave you seed money to start this.

[00:10:15] CR: I had the money from the Art Institute, which was about $2,000. My grandmother gave me around $1,500 or $2,000, just to like, “Okay, you’re moving to a new city.” That was all I had. That was it. Guess what, I’ve never – I don’t have any loans. The company is very, very, very knock-wood, profitable. We’ve grown. In the last year, we’ve doubled. It’s all knock wood, been the 20-plus year overnight success story. It’s really been, in the beginning, it was so small and incremental growth, because I never had outside capital. 

My dad literally would co-sign loans where their house would be on the line, so that I could buy fabric, sew real fast, ship it out, get paid and then pay back the loan. That was the first year or two, they supported me in that way. It was always like, had to pay it back immediately. Then, I’ve never had investors, that might be happening soon-ish. We’ll see. Because now, I think we’re at a point now where it makes more sense.

[00:11:36] TH: 100%.

[00:11:38] CR: Yeah, it’s been a long, slow, steady growth and mostly, just building the brand awareness, which people think that companies 10 times bigger than it is, because of the awareness, which is to me an opportunity. That’s what we’re working on now.

[00:11:55] TH: It is remarkable.

[00:11:56] CR: Filling up that bucket, that opportunity bucket.

[00:12:00] TH: Yeah. I mean, Cynthia, what you have built in your name, your reputation, the incredible product and styles, and even just the fact that you’re at the forefront of, and I understand this, because of your passion for surfing, but this idea of I’m going to design wetsuits to be fashionable. I mean, you really are an incredible visionary. I think, what really blows my mind and blew my mind as I got to read about you and understand your story is you have an incredible sixth sense in business. You have great business acumen.

You would not be where you are today with ownership of your own business and sell funding it based on receivables, if you didn’t have great instincts, coupled with excellent taste, because if sell-through doesn’t happen, as you well know, if sell-through, it doesn’t happen and people are buying what you make next season, there’s not the demand that it was. In many cases, I think, tell me if you disagree, but I think you’re in many cases, only as good as last season, at some point in your career, until you become a Cynthia Rowley and everybody knows you. Then there’s a tipping point in which maybe that shifts.

[00:13:12] CR: Oh, thank you. Well, about three years ago, we really shifted a lot of the wholesale because to me, it didn’t make sense that you would ship goods to someone. They’d sit in a store, you’d hope someone would come in to the store. You’d hope they’d pick your thing. You’d hope they try to – just was like, so many filters that it didn’t make sense to me that you’d be throwing up that many roadblocks to your own audience.

We’ve pivoted and we really are right now, we’re 90% DTC with dropships and affiliates and our own brick and mortar. I just saw the writing on the wall. I do think — thank you for saying that about being a little bit of a visionary, because I do think when I look back at my career, I was the first designer to work with a Target, before Isaac Mizrahi, before any of their short-term collabs. I was doing it for three years and built a 100-million a year business at Target. Then and now, working with mass retailers then became the paradigm for designers doing runway shows, and then also, understanding a more accessible path.

I think, even, I think, there’s just been so many risk taking, I would say, where I thought, you know what? This is crazy. I always say, if it’s not a 50/50 chance, it’s going to be epic, or the end of my career, then maybe it’s not worth doing. I need to be doing something that I’ve never done. I like to be a little bit scared all the time. I like to be challenged. I like to try things that only the craziest people would try. That’s what we did with wetsuits. Now, it’s really become the functional fashion part of our brand, where we’re pretty dresses, and then badass wetsuits and serpent swim. We are in a week, introducing skiing and snowboarding apparel. All functional, everything. That’s coming up in about a week. I mean, I would just be bored if all I was doing was apparel. To me, I’m just like, I have to keep pushing myself.

[00:15:41] TH: Yeah. I mean, you’re in home furnishings. You’re in glasses, color cosmetics, you’re in handbags. I mean, you are a lifestyle mega brand. I think, I would love to know, because if anyone’s listening and saying, “Gosh, I’m just starting out as a designer myself. Yes, I have the Internet and I have all of this resource.” Was it perfect timing, or was there a magical tipping point? Do you remember a particular shift in which you felt like you were slogging uphill, and it shifted or pivoted to all of a sudden, you realize like, “Hey, I’m actually a designer. People know my name.” It was at the Target breakthrough, or was there something that you can hindsight, that you remember that you thought, “Wow, this is a pivotal moment”?

[00:16:28] CR: I mean, you always say, you can’t believe the good reviews and you can’t believe the bad reviews. Early on, I guess when I won the CFDA award, that was exciting. I knew that wasn’t enough. Just was not even close to enough. That brought a little bit of recognition. Then yeah, I would say, Target was big. A lot of name recognition with that. Then, I guess, just through the years, putting so many things out there and being open to talking to my audience and being out there in front of the brand, I think, we built a really loyal – we have a really loyal audience. Yeah, I’m just really grateful.

I think, it’s fun that we can introduce new products, whether it’s something in home, or something in sport, or accessory, or ancillary fashion category. I feel like, I’m doing it for my customers, for our audience. Doing it to keep them excited. Of course, it’s exciting for me, but I feel it’s my duty to keep reinventing the DNA of the brand that people know, but totally reimagining it in different ways, how does that manifest itself in – I’m looking around here. Yoga mats, little cashmere throws. There’s some cute boots over there.

[00:18:04] TH: I think, it’s interesting, too, because you’ve had such an epic career, how did you end up managing personal life in terms of falling in love, or having a child? I mean, you were able to incorporate all of that into building this incredible company? Was that fate and timing? Did you know you wanted to have a child? Was there an understanding that you felt like, “I could take some time away from the business to do this?” Or you just thought, “You know what, it’s one day at a time, and I’m going to figure it out”?

[00:18:41] CR: Well, I’ll tell you. I had a five-day maternity leave with my first daughter and a 48-hour maternity leave with my second daughter. I would never condone that ever. People in my company take as much time as they need. It’s just for me personally, I’ve had a roller coaster personal life. My greatest love has through thick and thin, always been my work. When I lost my first husband at age – I was 34, he was 30. I thank God, I had my work, because I could pour myself into it.

Then, I thought I would never have a family. I thought it would never have the opportunity to have a child. Thank God, I did, but I couldn’t reconcile necessarily the happiness that I get from my work. Obviously, the greatest thing in my entire life, hands down, no question, are my kids. That is like, I would give up anything for them. I thought, if I can balance this, if I can do this, then my happiness at work, I’ll be able to raise happy children, too, and become a role model for them.

I’ve asked them now that they’re older, my youngest is 16. I say, “Did you guys ever feel like I spent too much time it work? Was I not there for you?” They both say that, watching the joy that I get from my work and combined with the seeing how hard work can make people happy and showing them that if you want something in life, you actually – you have to work hard for it. I think that in that respect, I’m so grateful to have this, to have this job and to have this company. I don’t think I’m not encouraging either one to go into this industry. They both have their own things they’re interested in. I have great people that I’ve worked with here for 20 years, or more even. I am having way too much fun to want to stop.

[00:21:17] TH: Yeah. Well, and just so you know, we’re separated at some point at birth, because I had four days off my first. I always scheduled C-sections, always on a Thursday, so I could have Thursday, Friday, Saturday, Sunday, Monday, and then be back on a Tuesday. I say the same thing that you’re saying. I don’t necessarily advocate that, because I ended up having three, 18 months apart. It’s a lot to have three kids to begin with, right? It is my greatest gift and passion.

I just figured, there’s no manual here. I think, if I show up and I’m fully present, and I get to do all the best parts of being a mom, even though I also, am in love with business and business has been an equal love to me, to my children, it was forgiveness of myself, some of the harsh opinions I had of myself of what I thought it might mean to be “a good mother,” versus not a good mother. Or am I somehow not showing up enough, because I’m not spending as much time as some of the other parents are, and really having to continue to check in with myself to recognize that these little people come through us, not necessarily from us.

I think, as much as I look back, I wouldn’t change it, because they got to see me and my best passion and my height of my – the things I love to do too, which I think inspires them to be on their own path of figuring out who they are. I so understand you.

[00:22:57] CR: I learned from them all the time. I mean, don’t you think even just being a mom is basically, you have to be as organized. It’s the same thing. I never talked about work at home, unless it’s something like super fun. Like, “Hey, you guys. Did you hear, blah, blah, blah? I’m pretty excited about this.” I don’t bring my work home with me. I do think the skills that you need to be an entrepreneur and to run a company are exactly the same skills that you need to be a mom and run a household and take care of take care of your shit.

[00:23:42] TH: Completely. The fact is, is you get to now enjoy your daughter as an adult, and you’re doing this podcast with her. You speak on the podcast a lot about topics that I’m personally passionate about; breathwork and mindfulness, meditation. Well, I would say total health and wellness 360. When did you start to, or were you always – was that always a passionate part of your life? Or when did you realize mindfulness, or slowing down and having connection with yourself and living in some of the more, I guess, present and intentional ways became important? Was there a moment that that happened? Or was it always part of your life?

[00:23:42] TH: Completely. The fact is, is you get to now enjoy your daughter as an adult, and you’re doing this podcast with her. You speak on the podcast a lot about topics that I’m personally passionate about; breathwork and mindfulness, meditation. Well, I would say total health and wellness 360. When did you start to, or were you always – was that always a passionate part of your life? Or when did you realize mindfulness, or slowing down and having connection with yourself and living in some of the more, I guess, present and intentional ways became important? Was there a moment that that happened? Or was it always part of your life?

[00:24:28] CR: Well, I think, living in the present is probably one of the most important things about running a company. You can never look back with any regrets. You can never rest on your laurels. You shouldn’t think about your own history. You should look forward, but really attack what’s happening right now. I mean, that’s always been – That’s always been my mindset, only because I think also, in the beginning, when I started, I didn’t know if I was going to be around next week.

All I could think of is right now and what can I do? I would set tiny little goals and short-term achievements for myself, so that I could feel like, “Okay, I’ve achieved this. Reach this goal. Now, I can move on to the next one.” Because otherwise, you set lofty goals. I think, it’s really hard. I think, it’s easy to beat yourself up. It’s not happening. Why aren’t I at this level? I think, the gratefulness, the gratitude for being present and achieving things right now, I think is what pushes you forward. I love sports. I love sports. I really feel that’s my meditation. Surfing, crazy stuff. I ride a bike to work every day and home and I really feel like physical activity is a lot of what keeps me focused when I’m at work.

[00:26:20] TH: I get it. I would say, exercise is my meditation. I do love meditation, but I would say, exercise is one of my absolute requirements daily. I don’t know how to manage stress other than that, and pressure. It just is absolutely mission critical. In terms of your being so front-facing with your brand, do you have your name on the label? As you think about how you develop this empire, was there ever a time where you thought, “Gosh, maybe I should come up with a name?” Or is your name always the brand? I’m always curious, because as someone that develops brands in the beauty space, I’ve always thought through with the talent that I’m thinking through it with is, how we name the brand. How do you in hindsight now, looking back, was it just Ralph Lauren, and everyone was doing –

[00:27:22] CR: Yeah. That’s what you did. That’s what you did. Calvin Klein. Donna Karan. Name anyone, that’s what you did. If you were a designer, you used your name. There was no question. I mean, now, definitely. I actually am doing a lot of projects under different names, that people may or may not know, it’s me.

[00:27:46] TH: Interesting. Well, and I asked the question about that your name on the brand, because it jettisoned you into the forefront of the media in such a prominent way. I mean, you’ve been on The Oprah Winfrey Show. You’ve been on David Letterman. You’ve been on America’s Next Top Model, Project Runway, Good Morning America. I know, there’s a whole long list. Was there a point in time where you thought, “Gosh, I hadn’t really anticipated this being part of the brand”? Were you always comfortable being front and center, in front of the camera and in front of the media?

[00:28:21] CR: I mean, I’m not really that shy. I think, early on, I had impostor syndrome. I was definitely like, “People are going to figure out the real me. I better really take it up a notch,” in that fake it until you make it way that I was like, “I got to just put myself out there.” I forced myself to do that. Now, it’s like, how they tell writers, like, write what you know. For me to have the opportunity to talk about what we do, it’s really fun and exciting. I want people to know the story. I want people to know our sustainability efforts, and everything that we’re doing charity-wise, and how we run the company with small – we make small runs of everything we do and then replenish, so that there’s no waste.

I don’t know. Now, it’s fun for me to tell my story, because I’m really proud of how we’ve evolved, and stayed relevant. I’m really excited about new stuff we’re doing, and new things coming out, even over the next couple of months.

[00:29:46] TH: I’m so excited and thrilled to hear. I can’t wait to see what you’re up to next. You’ve also co-authored, or authored several books. When I looked at some of the titles on your books, I was really excited to see what you had developed. Were you always feeling you wanted to write a book? Or where did the decision come in?

[00:30:14] CR: I mean, everything we do is storytelling, so why not actually tell a story? Those were a long time ago now, but it was, at a time when I didn’t want to just make clothes. That was never my interest, to only make clothes. I always just wanted to create things and it didn’t matter if it was fashion, or home, or a car, or a bike, or roller skates or whatever. It didn’t matter. I think, I just early on thought, if I can give tips – The first book was called Swell: A Girl’s Guide to the Good Life. It became a best-seller. I wrote it with my best friend, Ilene. We had so much fun doing it. We were out doing all of those things.

It became this bible for young women starting out in their first jobs, or second jobs. It was really fun to do. Now, I don’t know, people have been asking me to do books for the last few years. I don’t know, it’s just so sweaty. It doesn’t seem modern to me. I mean, at the time, amazing. That was how you could talk to people. Anyone who would listen, that was how you could tell your story. Now, there’s so many other ways. Through social media, through podcasts like we’re doing right now. There’s so many other ways. To sit down and be like, “Okay, I’m going to write all my ideas into this. I don’t know.” It seems really sweaty. I don’t think I want to do it again.

[00:31:57] TH: Well, you’re the visionary. I would be completely trusting your instincts.

[00:32:04] CR: Yeah. I think there’s other ways. I mean, if I was a novelist, if I was writing fiction, that’s a whole different story. That’s an art. That’s art. I don’t need to tell my story, or I don’t need to have a monograph, really. It seems egotistical and not really important to me. I like to think ahead. Just like I was saying, I like to think ahead and not think about what’s happened in the past. Even though, I have such great memories, but I don’t think like that. Almost, my mentality is like, hey, this fashion thing is really starting to work out. This is cool. That’s literally how I feel like, “Wow, this is working.”

[00:33:00] TH: You’re so amazing. You’re just great. I think, that’s important, though, that listeners hear that from the outside, people can look in and say, “Wow, you’re so successful, and you’ve made it, and how lucky are you?” They could say that 10 years ago, 15 years ago, 20 years ago to you. Yet, we didn’t necessarily ever feel that way. It always feels like, I’m only as good as last week’s invoices. Or this this week, I make payroll, and it’s these micro wins. From the outside, people can think everything looks so easy, or it’s already happened. It’s just, I totally acknowledge the feeling. I think it was in 2017, I won my first big award. I thought, “Oh, my gosh. I didn’t even know these people knew who I was. How are they giving me an award?”

[00:33:53] CR: Don’t you create your own awards, every day? Every day, you have to tell yourself like, “Here’s my win. These are my wins today. Okay, I had a couple of setbacks, but these are my wins. That’s what I’m going to take with me when I leave. I’m going to bring it in in the morning.” I read this thing that Hemingway would – he would only stop working when he had a great idea. Because he knew, he could come in the next morning and just step on the gas. He didn’t want to finish something, and then come in in the morning and have to start all over again. When he had a great idea, he would leave and then kick it off in the morning. I think, that’s a great lesson that you take your wins, and then you try to amplify those and come in the next day, guns blazing.

[00:34:57] TH: Yeah, completely. I think, the thing I’ve heard from you, which really resonates for me too, is you’re constantly checking back in with yourself to ensure you’re feeling authentic about what it is you’re developing and designing, and that you’re continuing to keep yourself on the edge of fearful, to push yourself into something new that may not be comfortable, but feels you need to explore it. There’s a real difference, right? That’s a huge difference, than just sitting back and collecting a check and put a bunch of junior designers in and say, “Check in with me once in a while. I’m going to be drinking Mai Tais in the Bermuda Triangle.”

[00:35:37] CR: There’s me and to other people that design every single thing, that has my label on it. I mean, yes, we have partners and licensing arrangements and stuff like that, where they execute the general idea. Everything on our site, almost every product is designed by the same three people. That’s a lot of work.

[00:36:08] TH: It’s a lot of work.

[00:36:11] CR: This t-shirt, I picked these colors, these pants, I worked on this print. It’s real. I work my ass off. That is the only way that you can be authentic. It’s the only way. I mean, unless it’s not your vision. It’s your vision. I mean, ask Steve Jobs. He tried to get out and had to come back in. If you take your hands off the wheel, I think that’s when it may be hard to get back on the road going full speed ahead again.

[00:36:51] TH: Frankly, I think because you have maintained equity ownership of your business, and been able to grow it, and I’ll bet slowly, it takes time. You didn’t sell the business early on and get beholden to a bunch of investors who are asking you to perform at a P&L level that maybe inauthentic to just your own design, cadence and the pacing in which you wanted to come out with a new product.

I think, that’s such a tribute to you on the business side. I mean, that’s why I find you so remarkable on a lot of levels. You have such a strong sensibility on design. Yet, on the flip side, I would say, you’re equal to, or better as a business person, because you’ve been able to navigate both. I just find that very, very unique.

[00:37:45] CR: I love the business side of it. Other, looking back to past things that I would have done differently, I never would have had – I had a Harvard MBA CEO that was a brilliant business person, but no creativity. No sense of why we’re here, what we’re doing and how these – We’re not making widgets, where it’s an emotional connection that people have with what we’re doing. I think, when, in March 2020, when I thought my career was over, and then I had to get my shit together and say, “Okay, how are we going to pivot and make this better and understand what we’re doing better?”

I put the creative people, including myself, as heads of the company running the business part of it, as well as the creative, because it really is. It’s completely, completely linked. I know, every single day, through all of our digital channels, I can tell you the best sellers, top 20, best colors. All of that informs, to some extent, while still reinventing and keeping everything fresh, it has to inform what we’re designing. You can’t design in a vacuum. You can’t just go. Then that becomes an ego trip. That’s me saying, “This is what I think you should wear.” No. You tell me what you like, and what you want, and what is right for now, and works for your lifestyle. That’s what I’m going to then imagine in through my own filter, and be inventive and original, not more – That’s how we do it. Totally different than how it was being done before.

[00:40:12] TH: Yeah. Well, I mean, I’m so inspired, and I can’t wait to meet you in person. I feel like, I need to come and sit and have Thanksgiving dinner with you. I don’t know if you’re available.

[00:40:25] CR: Well, that’s the one thing I will say, when we talk about ways to balance your life, anytime there’s a school break, I’m outie.

[00:40:36] TH: Are you?

[00:40:38] CR: Yeah. We’ve gone to Egypt for Thanksgiving vacation. We went to Senegal. It doesn’t have to be long. It just has to be really, a different experience. Anytime there’s a break, we go. Yeah, we’re going to be gone this Thanksgiving, but I don’t know if I should say that. Yeah, maybe just take that out. Anyway, I like to travel. I love to travel.

[00:41:05] TH: Yeah. Got it.

[00:41:06] CR: Hopefully, that we can do that again.

[00:41:08] TH: Yeah. Well, if you could hindsight or sit down and memorialize yourself as you want to be remembered, in really thinking about the legacy you’ve left, and how you wanted to – would want us to think back, is there anything that you’d want to share that just is a really hard lead, or intentionally focus personal mantra, or something that you would want us to know?

[00:41:40] CR: I mean, I just really want to emphasize the age old saying that hard work pays off. Because I do think everything is cumulative. I don’t think in the same way, I was saying like, don’t believe – if something great happens, that’s not it. Or if something bad happens, that’s not it either. It’s like, the cumulative effect of being able to evolve and stay relevant, and be original. I mean, that’s what I hope people remember that that’s what we tried to do. Maybe with a little wink, or a sense of humor.

[00:42:22] TH: Yeah, I was going to say, too, with just an incredible zest for life.

[00:42:29] CR: Oh, that’s so good.

[00:42:31] TH: Yeah, for sure. Actually, I would also say that you have a gift for surprising and delighting.

[00:42:39] CR: Thank you. I always say, sometimes I feel I’m the designer that’s hiding in the bushes, that pops out and goes like, “Surprise. We’re making roller skates. Surprise. Long johns and ski wear.” I just like that vision in my head, that I’m popping out, surprising everyone.

[00:43:03] TH: Yeah. I think, they said, a carefree and simple spirit.

[00:43:10] CR: Oh, that’s so nice. Hopefully, yeah. It’s not totally carefree. Not totally simple. Definitely, I think that’s a – that may be the grounding foundation that makes the chaos bearable.

[00:43:27] TH: Right. I so understand. Oh, Cynthia. Well, what an incredible afternoon. Thank you for spending this Friday with me, and sharing your story.

[00:43:40] CR: Thank you so much. I really appreciate it.

[00:43:42] TH: Yeah, you are incredible. You’re a legend.

[00:43:48] CR: No, back at you. You too. Thank you so much. It’s really fun talking.

[00:43:54] TH: It’s really an honor.

[00:43:55] CR: Yeah, I loved it.

[00:43:58] TH: All right. Well, thanks.

[00:43:58] CR: All right. Take care.

[00:43:59] TH: Okay. Bye-bye.

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