Jenna Lyons on Leaving J.Crew and The Real Housewives to Reinvent Herself

9 Sep 2026 · 1 h 5 min · 27 chapters

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In short

Jenna Lyons reflects on reinvention after leaving J.Crew (2017) and moving beyond fashion into TV, beauty, home decor, and brand strategy. She discusses why clothing details, tailoring, and “intentional effortlessness” matter, how confidence is built through feedback, and how identity can collapse after a career shift.

Guest background

Jenna Lyons began at J.Crew at 21 as an assistant menswear designer. Over two decades she became president and executive creative director across J.Crew, Madewell, and Factory, credited with tripling revenue and transforming the brand’s fashion influence. She later became a reality TV figure and founded beauty/home-related ventures; she’s now a partner/executive creative director at a brand strategy firm.

Key claims

Middle-tier fashion lost craftsmanship focus; she stopped buying as much and prefers made-to-order pieces and tailoring. Confidence comes from positive reflection, not complacency. People fear standing out because confidence can make others feel threatened. “Effortless” style is intentional, not contrived.

Notable examples

J.Crew blazer linings (silk tie piping, contrast lining, cross-stitch); seventh-grade bias-cut long skirt that led to her sewing career; 2006 US Open night match dress designed off Nike; her J.Crew catalog-to-magazine approach; leaving J.Crew brought depression, isolation, and no calls, followed by TV/consulting opportunities.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Jenna Lyons: From J.Crew to Reinvention

0:00 to 1:58

Learn about Jenna Lyons' impactful journey from J.Crew to her current ventures.

“I didn't get a single phone call, you know, and I think people have said to me, I don't believe you.”

Jenna Lyons: From J.Crew to Reinvention

2:03 to 2:14

Learn about Jenna Lyons' impactful journey from J.Crew to her current ventures.

The Importance of Detail in Fashion

2:29 to 3:54

Explore the significance of craftsmanship and detail in clothing.

“I can only imagine there's a few out there.”

Identity Through Clothing

3:54 to 6:54

Jenna reflects on how clothing shaped her identity and self-confidence as a child.

“I think that has gotten lost, you know, in a lot of fashion other than really high end.”

Building Confidence in Fashion Choices

6:54 to 9:56

Discussing the journey of gaining confidence in fashion and the challenges faced.

“So I got a subscription to Vogue for Christmas and my grandmother gave me a sewing machine and I was like, this is it.”

Memorable Fashion Moments in Sports

9:56 to 12:04

Maria and Jenna share their memorable fashion moments from their careers.

“But again, it's because I had feedback that they either sold well, or people said I love them, or I pinned your bathroom, or all those things that you get that reflection back.”

Embracing Uniqueness in Style

12:04 to 14:01

Jenna offers advice on how to embrace unique fashion choices and self-expression.

“But I, like you, I was so focused on the details.”

Embracing Unique Style Choices

14:01 to 20:52

Discover how to highlight your individuality and stand out through fashion.

“But back to those contradictions in design, like not everyone develops that confidence to make bold choices.”

Sponsor: Amazon Prime

20:53 to 22:30

Learn how Amazon Prime supports a fast-paced lifestyle with essential deliveries.

“And if you want to take advantage of it all, which I always do, you have to learn to keep a bag packed and your calendar loose.”

Jenna's Journey at J.Crew

22:31 to 28:00

Explore Jenna Lyons' influential career from designer to president at J.Crew.

“I want to take you back to the years at J.Crew because they were incredibly pivotal in your career.”
Show all 27 chapters

Fashion Industry Challenges

28:00 to 33:28

Learn about the competitive landscape of the fashion industry, especially for mid-tier brands.

“And the problem is that with the influx in the United States of Zara and H &M and Uniqlo, they are producing great clothes at a really affordable price.”

Career Trajectory Insights

33:37 to 36:05

Understand the importance of focusing on work and experience over titles in a career.

“As someone that started at a company at the bottom of the ladder and worked their way all the way to the top, how do they go about that trajectory?”

Evolution of Fashion Magazines

36:05 to 38:16

Explore the changes in fashion magazines and their impact on style curation.

“catalog into, I'd say, like a glossy magazine that showcased the brand from an entirely different perspective.”

Authenticity in Social Media

38:16 to 40:46

Discuss the role of authenticity in social media and its relevance to modern brands.

“He wants to learn something and he wants to really learn something that feeds him.”

Post-J.Crew Transition

40:46 to 42:01

Hear Jenna Lyons reflect on the emotional challenges after leaving J.Crew.

“talk about the year that you left J.Crew.”

Navigating Personal Isolation and Identity

42:01 to 44:04

Jenna discusses the emotional fallout of her professional identity and personal relationships post-J.Crew.

“I had all these people taking care of me and all of a sudden I had none of them.”

Transitioning from Athlete to New Identity

44:04 to 46:30

Maria shares her experience of losing her identity after retiring from sports and how it relates to Jenna's journey.

“I wasn't depressed because I loved what I did for so long, but I loved it because my body and my mind was in it and my body was depleted.”

The Struggles of Reinventing Oneself

46:30 to 49:20

Jenna reflects on the challenges and loneliness of her quiet period after leaving J.Crew and how it affected her self-worth.

“Honestly, it took, I would say, over a year, almost more.”

The Influence of Motherhood on Career Choices

49:20 to 51:45

Jenna discusses balancing her career ambitions with motherhood and how her son perceives her work.

“I really didn't, I did not see how unhappy I was and how scared I was and how lonely I was.”

Reality TV: The Unexpected Challenge

51:45 to 55:04

Jenna reflects on her experience with reality TV, the emotional toll it took, and the lessons learned.

“And there's never been a time where I've ever felt like he doesn't remember the stuff that I missed.”

Consulting for Brand Development

55:04 to 56:00

Jenna explains her role in consulting for brands and how her experiences shape her approach to value creation.

Consulting in Diverse Industries

56:00 to 57:24

Learn about the challenges and insights of consulting across different sectors.

“really re-established and rethought about what that brand could be.”

AI's Role in Daily Life and Business

57:24 to 59:45

Explore how AI is utilized in personal life and its potential in business optimization.

“I remember when AI first started and I was like, oh, OK, now I can, you know, change, you know, change what my countertop looks like in my kitchen and I see if I want to change the color.”

The Future of AI in Fashion

59:45 to 1:01:28

Discuss the potential impacts of AI on fashion, models, and authenticity.

“I think probably much more on the manufacturing side than anything else.”

Fashion Choices and Personal Preferences

1:01:28 to 1:04:05

Hear insights on fashion choices, dress codes, and personal style opinions.

“I think it's so hard to understand where it's going.”

Empowerment Through Hiring and Confidence

1:04:05 to 1:05:29

Understand the importance of hiring talented individuals and personal confidence.

“It impacts people the way they perceive you.”

Empowerment Through Hiring and Confidence

1:05:35 to 1:05:55

Understand the importance of hiring talented individuals and personal confidence.

“so I need products and services that can actually keep up with me.”
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Transcript

Automatic transcript. May contain errors.

0:00I didn't get a single phone call, you know, and I think people have said to me, I don't believe you. But I had become so synonymous with this brand that all of the bigger brands that could afford me didn't want me. I mean, what is Ralph or Michael Kors or Gap or Banana? They're like they don't want me because I'm J.Crew. It was scary. And I and then I separated from my girlfriend. I mean, it was just talk about the house that I built. It was just coming down brick by brick.

0:32It's Fashion Week here in New York, and I thought, who better to talk to than one of the most influential people in American fashion? Jenna Lyons started as an assistant menswear designer at J.Crew Brand at just 21 years old. Two decades later, she was president and executive creative director of the company she helped triple the revenue and turn a mall brand into a genuine in force in fashion. But her story doesn't stop there. She's since reinvented herself as a reality TV star, a beauty founder, a home decor designer, and now a partner and executive creative director for a brand strategy firm for businesses.

1:08Through every act, one thread has stayed consistent. She refuses to choose. Sequins and camouflage, a feathered skirt with a crisp white button-down, masculine and feminine, pretty and tough, all at once, all on purpose. She spent her whole career proving that the most interesting thing you can be is contradictory. I'm Maria Sharapova, and this is Pretty Tough.

1:47Speed makes it possible to seize every moment wherever I am. Whether I'm at a hotel, at the office, on set, or at home, I know my favorite products are just a click away. Visit Amazon.com slash Prime to find millions of items delivered fast. Same day delivery? It's on Prime. Available in select areas. Terms apply.

2:13Jenna, welcome to Pretty Tough. Thank you for having me. So much for joining me for this conversation. I feel like our worlds have crossed in some ways, but we never have officially met. So it's true. Yes. New beginnings. I'm excited. Welcome to the show. Thank you. I love to start these segments with a quote by the guest. I can only imagine there's a few out there. Let's see which one you picked. It's funny how many of our guests have the same reaction. They're like a little excited and a little scared. But since it's fashion week, we are going to ask you a question. about clothes. And it's about, you said something about a friend who was making clothes for the very first time.

2:52And you say, everyone underestimates the amount of detail that goes into clothing. And I love that because I feel like we're currently in a world where we don't focus on the small things. We make a big deal out of something that's not really important. and the way something is made, the fabric, the stitching, the producers, the people, like the heart and the soul behind a product is so important. When I think people recognize it, even though they don't realize, I remember we used to make jackets at J.Crew and we would put these incredible interior linings, so like this beautiful silk tie piping and a contrast lining and then a beautiful little button and a cross stitch.

3:35And interestingly enough, they were just navy blue blazers. Everyone probably already owned one or they didn't necessarily have a reason to buy a new one. But that's all they talked about. And it's interesting you say that. Sometimes it's the stuff inside. It's like that secret. It makes you know that someone really thought about what was made. They put time into it. They put love and care. I think that has gotten lost, you know, in a lot of fashion other than really high end. I think things have really separated. The world is really very, very high end or very commodity. And so I think that middle tier is not getting serviced as well as they used to.

4:12And what are some of those details in your wardrobe right now that are important to you? I've stopped consuming clothes the way I used to. I think I look for, I have a lot of my clothes made now. I used to purchase a lot of clothes, but I don't do that as much because I really enjoy getting something made. Like I have all of my shirts made. I have most of my suits made. I mean, jeans are hard. You can't really get jeans made. That's sort of a no-no. I still tailor my jeans, though. You do? Yes. I like to get a size up and then I tailor the waist. Oh, interesting. Because I have a longer torso.

4:47Is that what's going on? Yeah. Are you sure? Definitely. I'm kidding. Definitely. Wider hips, long torso. Have you ever tried Japanese jeans? Yes, but then they're too short. Yeah, that is a problem. And I don't like very cropped jeans. No, same. There is one brand that I really like that actually is a Japanese denim brand that makes them longer, which I will share with you. Please, because we're going to reference that in the show. I want to take you back to seventh grade. No, God. Honestly, please, because at the current state I'm in, I would like to go back. So a popular girl commented on a skirt that you were wearing.

5:22It was long, which at the time wasn't like the popular length to wear. Well, it also wasn't available to me. So you probably experienced this like you were, you're 6 '2", correct? And I don't know, how old were you when you were 6 '2", your full height? Like 18 years old. Oh, so I was six feet tall in seventh grade. So that's like 13. So there was no place for me to shop because I was very skinny, but really tall. And there was no like J brand jeans or all these new skinny, longer jeans. It doesn't frame. That didn't exist back then. And so I was constantly shopping in the big and tall section.

5:57So it wasn't necessarily that it wasn't a popular length, but it just didn't exist for me. Everything that was that long was much bigger. and anything that fit my little frame was really short. And so it was the first time I'd ever made something that was like liquidy long and thin. It was bias cut. So it really kind of was very shapely. And, you know, I mean, again, I had my little seventh grade body and I like realized that that was just something I'd never been able to wear before. And so Darlene Patterson sent me a note in social studies and was like, I really like your skirt. And I was like, I made it.

6:30And then she was like, would you make me one? And it was like the world sort of opened up. It was the first time that I'd ever gotten really positive feedback about the way I looked. And the fact that it was something that I'd made, that I made myself, that I could make again, that I realized, like, this could be a gig. It was the first time I thought maybe I— In seventh grade. In seventh grade. That's when I knew what I wanted to do. So I got a subscription to Vogue for Christmas and my grandmother gave me a sewing machine and I was like, this is it. I'm off. Was it also one of the first times where you realized that a garment can have that much power on your identity?

7:08It was pretty loaded because I started to understand it wasn't just the clothing that gave me power, but it was the way that I was reflected back from another person and how impactful that can be, how someone else saying you look good. I really hadn't experienced that. I was kind of an ugly duckling and I had a genetic disorder. So my teeth were shaped like cones and I had a huge bald spot in the back of my head. So I had not gotten any kind of reverberation to me that I looked good. And so I think it was very loaded in the sense that clothing can be armor, clothing can be power, but clothing can also really build your confidence.

7:45And I didn't get that. I mean, I was 13 and, you know, it was really an exciting moment. And I guess the simplicity of a compliment coming from another young girl. Especially someone I admired, which I think. And I feel like that lesson, I mean, resonates today. For everyone. several many years later of course I mean I think somebody who you look up to or respect giving you positive feedback is really so much more valuable than anything I also think this idea that I created the thing myself so I had it had a deeper level of accolade because I made it and I made all the choices I picked the pattern I picked the fabric it was a yellow with watermelons I mean, I love that you mentioned that because I mean, going back many years, I mean, you were known to put these incredible combinations together, like sparkles, camouflage, different shapes and patterns and volume with, you know, volume on the top and a pencil skirt.

8:49Where did you grow that confidence to make those bold decisions? I mean, I don't know where the hell it came from because I didn't have it growing up and I didn't have it when I was in college and I didn't. It was a little bit like building a house by hand. It didn't happen overnight. I really had positive feedback. And every time I got positive feedback, I felt a little better and more confident. And the next time I did something well and somebody said, OK, you did a great job or that sold really well, it kind of added another layer to my house. But the house was little and kind of broken and certainly not confidence.

9:28That was not something I had growing up and not something I had really until like I would say the middle of my career, probably not until I was like in my early 30s. You know, I really didn't have it. And it came it was hard earned. And I think there is this idea. Some people just have it, and I'm so envious of those people who just have it. Do you still feel like you have to work at it, or does it come more naturally now? I certainly trust my choices now. But again, it's because I had feedback that they either sold well, or people said I love them, or I pinned your bathroom, or all those things that you get that reflection back.

10:05But were you confident when you were growing up? I was not confident in my fashion choices, no. When did you know, I mean, obviously you were 17 when you won Wimbledon, so that's a very young age. But when do you feel like you were like, oh, I'm better than a lot of these people? Never. Never? I never allowed myself to believe that. Really? Why? Because every time that I got to the point of feeling confident or it turned into complacency, like I was good enough or I was good or great, whatever it was, it meant that there was nothing else for me to reach. And I just that for me was a very dangerous place.

10:41That's when I did my worst work. Really? Is during the moments of where you felt like you won and you were at the top. But with fashion and the things that I wore, I think with sport, you just become comfortable with being sweaty and uncomfortable and movement. And you grow into your body because you're already so exposed. I mean, what more can they see? I mean, sweat, tears, emotion, wind, losing, all of it. And you're going to dress this bit on national television. There's like no material. Because the less material, the better, the cooler it is. But you did make some interesting choices that I remember really distinctly.

11:20Like I remember that pink, frothy little dress that you wore. And I remember. Yeah. So like going back to 2006, I wore this little black dress that was very much inspired by Audrey Hepburn. Was this the Ricardo Tichy moment? No, that was several years later, but that was an iteration of it. He took like a modern spin on it. But the original, the original dress that I wore in 2006 was actually a design off at Nike. So they asked three designers within the company to design a night match for the US Open. And it was the first time that someone wore a different dress during the night match than the date dress.

11:56I love that. Well, and it's black, too, which is not traditional. Not traditional at all. Yeah, it was usually full of pattern, color, accessories. Yes. But I, like you, I was so focused on the details. And that neckline was very unique. And when you first look at it, you're like, how do you play tennis in that? But because of the materialization that we used and the shape, I mean, we worked on the shape. Like I was like, can I lift my arm? Like, can I serve? I've got really important things to take care of. There's some really specific goals here. But yeah, that was one of my favorite moments.

12:28How did that come to be? Like, how did you end up partnering with Ricardo Tishi? Like, that's a pretty unique experience. I mean, Nike doesn't do a lot of those. So they must like if Nike has to do a collaboration, it's usually with someone that doesn't have a sportswear line. So at the time, Ricardo was at Givenchy. So there was nothing there was no interference, no competition. And he had a great relationship with Nike. He'd actually done a little collab with them before on different products. So it was like a natural evolution of his partnership. and I remember that moment he came to my house in Los Angeles and I read that I thought that was yeah must have been so exciting I mean Ricardo was iconic because he was kind of mysterious like he I like I loved that goth approach about him and honestly I was a little nervous because I didn't know how that would feel on the court because my choices were a little more elegant streamlined and he definitely pushed the boundaries with what we can do with a tennis dress so it was fun picking his brain and I also think he learned a lot because he's like oh we can't do that because she's going to be sweating profusely men in general oftentimes it's so funny because I was putting on my shoes and I'm like I'm going to see Maria Sharpeau back to wear heels because she's tall and well I chose loafers so we did well we're the same height now but I was like hobbling towards the door I was like these are deeply uncomfortable I was like only a man could do this to us.

14:02Only a man could design these shoes. Oh, Christian. I know. I know. It's okay. But back to those contradictions in design, like not everyone develops that confidence to make bold choices. And for people that are not convinced about, you know, where to make impact in their wardrobe choices. Like, what would you suggest? I would say probably my best piece of advice is accentuate whatever makes you different. I remember really distinctly being afraid to wear heels. And I love heels. And I like the way I feel in heels. I like walking into a room in heels. And at some point, I was just like, why would I not?

14:45Like, everyone wants to be tall. Everyone wants to be able to wear really high heels and very wide leg pants and, you know, look like a tall drink of water. And I don't know why I was so afraid. I think I'd been conditioned because I got so tall, so young. But I think, you know, if you have something that makes you unique, I think using that and highlighting that. I also think developing signatures. I think it's so easy to get stuck in something that looks like everyone else. And, you know, I think particularly as it relates, I see it with jewelry where people are wearing the same bracelets. We all know, and I'm not they're wonderful, but like, what is it that's you?

15:22What is it that's yours? What makes you stand out? I think is a lot more interesting than just kind of following in the pack. Why do you think that people are so afraid of standing out? It's interesting, even when people do find their thing and when people stand out, I think someone who has confidence, people who don't have confidence want to take down. And I remember really distinctly being on a TV show with Matt Lauer and he said to me, he's like, oh, you know, well, your star is really rising now. That's when people want to take you down. And I do think there is something, I think, I don't know what it is and I don't know where this comes from, but I think particularly with women, it's harder.

15:56There's, isn't always this build everyone up like attitude. Sometimes there's this, and so I think people who have confidence and who show up in a room and who actually know who they are, sometimes make that person who doesn't feel as good about themselves a little uneasy. And so I think it can be scary because it kind of puts you in a little bit more of a spotlight. I think once you get through that and get over it, I mean, I'm sure you've been through so much. Yeah, that's something that sport really taught me is like through sport, you kind of just grow this thicker skin of not giving a crap.

16:29You're like, this is me. This is who I am. Win or lose. This is my personality. These are my emotions. And this is my style. You know, take it or leave it. Yeah, it's admirable. And it's also something that isn't that easy to do. And I think everyone wants that. Everyone wants to be able to like walk onto a court or walk into a room and own the room and feel in charge. And it's a hard, it's a hard one thing. And so it's not easy for everyone to do. I think it's scary for a lot of people. It was scary for me until I started to figure it out. I mean, I feel there's, there's always a little element of scary, but that's when you're pushing boundary.

17:05So I'm like, that's okay. I kind of like this feeling. I know if it's not scary, what are we doing? That's true. I recently saw your YouTube video where you're talking about effortless, like the secret to feeling looking effortless. What is it about that idea or that concept that resonates with you? I think it's a little bit of what you said where you're being a little bit more unapologetic about what makes you special and what makes you you, because that doesn't take effort. You know, know, to just say this is who I am, this is my style, and this is the way I roll is attractive. It's sexy. I think things that feel labored or contrived are not sexy.

17:50And I'm not attracted to something where you can tell that everything is completely orchestrated. You know, anyone can do and it doesn't. That's that's not truly like that's effortful. And I just not I don't know, It doesn't attract me. There is an element of contradiction in that in a way where I compare it to sport because that's something I did for so long is like you want it to look effortless, but you do put so much work and effort into the grind and the repetition and trial and error. And sometimes you're like, well, why should I apologize for showing that effort? Right. And I think there's an element of that in fashion where you see someone, you're like, oh, well, they're overdressed.

18:41They tried really hard. And it's critical. Oh, that's interesting. So I think there's a difference between being overdressed and trying too hard. Tell me. Okay. I'm intrigued. Well, to me, being overdressed is being a little bit too dressed for the occasion, meaning you didn't totally nail it. You didn't really understand what you were walking into. You maybe thought it was going to be fancier than it was, or maybe you are wearing your heel of full beat of makeup and diamonds and everyone else is in jeans. That to me is being overdressed. Well, they got the wrong party invite. Right. And listen, I've been there.

19:17I think that trying too hard is firing in all cylinders where everything is a thing and every, I don't know, just doesn't, like, I'm all for overdressed if the look is pulled together and there is some sort of sense of elegance. But when everything feels contrived and everything is a label and everything feels like something, you know exactly where it is or you can tell exactly where it came from or you know the, you know, that's the part where I don't know. I remember when I would I've done a lot of red carpet commentary. And I think one of the things that I always appreciate is when there's something a little bit off, when the haircut is a little bit shorter, when there's a little bit of a nuance, when somebody wears separates as opposed to wearing a gown, when they're not fully tan and fully perfect.

19:58and there's a little bit of an interest. You know, I think there's some, I think, you know, Cate Blanchett, there's always something a little soft about her. She always sort of, the jewelry is a little off or, and I mean off, meaning not traditional. You know, she's not wearing the full set of the necklace, the earrings that she, she knows how to break things up. And there's always that, Julianne Moore, I think is another one who doesn't do the traditional. And I think that to me feels, while very elevated and up and dressed, there is this deep understanding of style and nonchalance in there that I think is really hot.

20:32But I think it was intentional. It is, but it's intentional in the way that like... Looks effortless. Yes, it looks effortlessly. It's intention that looks effortless. It's intentional effortlessness. If that's a term, but we just created it.

20:52this is advertiser content from amazon prime september is go time for me i've got the open and fashion week back to back honestly i'm not scared of a packed schedule which is good because when the open and fashion week overlap it's chaos but the opportunities tend to be ones i never want to pass up i'll go from watching a match at arthur ash straight to a fitting back in manhattan then pivot to a brand meeting before I've even had a chance to eat lunch. And if you want to take advantage of it all, which I always do, you have to learn to keep a bag packed and your calendar loose. Every day moves fast.

21:28Thankfully, Prime moves just as fast, getting me what I need to say yes to any opportunity that comes to me before the moment slips away. Say the outfit I hope to wear isn't fitting right, Prime gets me fashion tape before I hit the show. Or maybe I get invited to a brand event with a few hours notice, but my phone is low on battery, which happens a lot. Prime has me covered with a portable charger delivered to my next location. Last minute business meeting across town. My favorite type of notebook and pen. Yes, I can be particular. And yes, I still love taking handwritten notes will be waiting for me at the front desk.

22:03And when the lights go down, that's when I step into recovery mode so I can do it all over again tomorrow. Magnesium salts for the bath, a face mask for a reset, a gym mat for stretching it all out. I kind of need all of that right now. All delivered wherever I am, when I need them. It's all about staying ready and making sure I'm prepared for what's next. Visit amazon.com slash prime to find millions of items delivered fast. Same day delivery, it's on Prime. Available in select areas, terms apply.

22:40I want to take you back to the years at J.Crew because they were incredibly pivotal in your career. You went from assistant menswear designer at age 21 all the way to the very top job. Creative director. President. President of three brands. So we had J.Crew, Madewell, and Factory. So it was three, which I think a lot of people don't realize. It was insane. Wow. I had no time. And you've credited your rise to a kind of obsession, not just with any garment, but how it's styled, how it's photographed back to those very details. Like, why was the entire package so important to you at that time? Before I had the top job, I oftentimes would have, you know, I had women's design.

23:29And then what would happen is the clothing would get handed over to the merchant team, they would edit and purchase it, then it would get handed over to the marketing team, they would decide how it was going to market it, and the stylist would take it, then the catalog team with the stylist would photograph it, then it would go into the store, and it would be set in a certain way, then there would be, you know, the storytelling and the writers who would get involved. So you had all of these different people putting their own spin, not bad, just their own spin. And so you can imagine as that initial concept gets all the way to the end, it got diluted or it just changed meaning along the way.

24:02And I realized that in order for me to maintain a consistent point of view around the product that we originally started to design, I was going to need to actually manage all of those steps. And it didn't happen overnight. But I oftentimes would say to the team, it's not that I have a better idea. It's just I have one filter. So the copy and the way that we talk about the product, the way that we're editing the film, the way that we're styling it, the way that we're actually shooting it for the catalog, the way that we're actually marketing it in stores, the way that you see every touch point that the customer has with that product is with a lens that starts from where the clothes started from as opposed to a lot of different things happening along the way.

24:40And so it was really about protection. It was about protecting the thing that we had all created that I really wanted to look a certain way and to be perceived a certain way. And in absence of that, it kind of got slintered. Lost its value. Does it feel like in the creative space and creative jobs, bosses expect you to be in one lane? And when you try to break through and experience all the different facets of the business, you're considered a rule breaker? It depends on the person and I think it depends on the team. You know, I think not everyone is right brain, left brain. Some people really sit steadfastly in one area and they like being in that.

25:29And I think there are a lot of people on the creative team who didn't want to really understand the business or they were like, let me just design my thing and this is my happy place. And I completely understand and respect that. That didn't work for me. I didn't because I wanted to, as I said, be able to really have a heavier hand in the trajectory of the whole product. And I also cared about the business and wanted it to do well because I knew that the better the product we designed did, the more opportunities we'd have to do more things and to try and experiment. So I understood that part. But I also had a boss at the time, like Mickey Dresser, who was a CEO, really supported me and believed in that and gave me chances and gave me opportunities that I probably would never have had.

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26:07I wasn't trained for it. I didn't go to business school. You know, I think things are changing now with the world we're living in, where traditional trajectories for people and going to college and doing all the things that you that's all going out the window. But tell me a little bit more about him, because, I mean, he was just one of those people who loved product and he put product and the customer first. You know, I think we had come from a place where we looked at the bottom line and that was what we focused on. But the bottom line is really, you know, a result of the product and what the customer perceives the product as being and whether they love it or don't love it.

26:43So I think he really reversed the conversation and said, like, let's just focus on the product and make sure it's beautiful. And then let's focus on the storytelling and making sure that the customer understands why this sweater is better than the other sweater, because this is Laura Piana Cashmere. And we're able to buy this in a bulk rate because we are buying a ton of it and literally tons. And so let's tell the story. And so that really shifted the customer's perception of the brand and shifted what we were able to do. And so he gave, you know, a lot more opportunities to people who were coming out of the design space.

27:15And he paralleled design to business. So, you know, by making me the president, he was saying, listen, the creative side of this business is just as important as the business side. And they are interlinked. Does it feel like there aren't enough of those CEOs at the moment in the fashion space that give creatives more space to breathe? I think the fashion space has changed so much. I mean, the turnover. Well, that's at the top. I think, yes. I think that, you know, when you're talking about, you know, the houses coming out of Europe, that's a very different conversation. But you have this real division of church and state.

27:57And when you think about there's the top top, which is really very elite, incredibly expensive. Unattainable. Pretty unattainable for most people. And then you have mass. And the problem is that with the influx in the United States of Zara and H &M and Uniqlo, they are producing great clothes at a really affordable price. And so it's making it much more challenging for the J. Cruz and the Madewells and the Michael Kors and all those people who are sort of sitting in that middle zone because they're competing against a humongous engine. And so, you know, I'm not really sure exactly what's happening on the inside.

28:36I don't have visibility to, you know, what they're experiencing. I will say what, you know, is happening at Gap with Zach Pozen being inside Gap. I think that's changed and you can really see his impact. So I think that that's really, you know, that's that to me gives me hope. And when you say impact, is it on the garment, on the piece, on the business, on the which piece of that business? I mean, well, and that's I guess the thing is to me, the business is the clothing that they're selling clothing. So that is the business. And so you see the quality of the clothes or the style has come back.

29:10There's they're much more relevant. The fits are better. I think, you know, when you look at Gap today versus what it was two years ago, it's a complete 180. And I think it feels more relevant. People are wearing Gap again. I'm hearing people feeling like, you know, it's back in the zeitgeist. And it was really not for quite some time. And that has really been because of, you know, I think Richard brought in Zach Posen to really change the thinking around what the brand was. they are doing Gap Studio, which is this more sort of tailored, more high-end, I don't know if I would say high-end, but more sort of couture designed.

29:44And you talk about tailoring, like tailoring is such a key piece of your wardrobe and something that you focused on immensely at J.Crew. And I don't think enough emphasis is made by many other brands because most of the clothing I buy. It's tailored. I think people don't really understand how unique and different that area of clothing and the way that you make that kind of clothing is. Because there's been sort of this dumbing down, so to speak, of apparel industry, I don't really think most people understand truly like what goes into a tailored garment and what tailoring really means. It's just not as culturally understood here in the United States.

30:29I think people who are European usually have a different relationship to tailoring because they understand that tailoring isn't just going and getting something fit. Tailoring is actually the workmanship that goes into cutting a jacket or a trouser. At one point, you compared your role as a fashion executive to a glorified crossing guard. Can you elaborate on that? Sure. I mean, I think anytime you get to a point where you are sitting in a pretty senior seat, if you are doing the work, you're not you need to let people do their thing. And so what happens is you start to really be more it's more about guidance.

31:11And so it's that's why I like into a crossing heart, which is like, hold on a second. Let's not do that. You come over here. Let's do that. This is great. Let's move this to the forefront. You over there, can you hold over? Can you come around this person? I want you to look at this. And so it's really about thinking about the idea runway and making sure also that you're getting the best out of each team, that they also are seeing what the other ones are doing. If something is not going the right direction, let's hold on that. But did that come natural to you? Because that's very different to designing the garment.

31:46It is. But when you get to, I mean, by the time I was, you're not designing when you're the president anymore. It's managing. And managing is a total, I mean, no one trains you for managing. I learned how to manage the hard way. On the job. Making mistakes, making people cry, making people hate me. And I think, you know, it's something that you start to see where you're like, how do I get the best out of someone? And oftentimes it's letting them do their thing. It's not micromanaging them. It's giving them room to make their own mistakes. It's remembering what did I enjoy when I was a sub, you know, a subordinate?

32:19What made me feel good? It's, you know, having, you know, giving someone real feedback, making sure that you're making decisions, not dragging decisions out, like just moving and not. I think that's another thing, like the analysis paralysis of, you know, having somebody, a boss who doesn't make a decision is like. Yeah, just choose.

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33:42As someone that started at a company at the bottom of the ladder and worked their way all the way to the top, how do they go about that trajectory? I mean, I would say if that's your goal, you're probably focused on the wrong thing. I think when you are trying to just move up, everyone around you feels that. I have been on the receiving end of people who worked for me, and I felt like they were more interested in the next move than the work that they were doing today. I was really fortunate. I loved making clothing. And so it wasn't really on my mind, particularly at the outset of my career. I just wanted to make beautiful things.

34:25And my desire to have a bigger job really stemmed from the fact that I wanted to protect and continue to really foster the land of these beautiful things. I didn't want these land of misfit toys to look like misfit toys. I wanted to protect all of my babies and take them all the way to the end. And that was my primary reason for wanting a bigger job. So I think focusing on the work and focusing on doing something, I know everyone says this, but if you're doing something that makes you look at the clock every day, you're probably doing the wrong thing. And not focusing on the title. Titles don't mean anything.

35:02I mean, the number of times I've walked into a room and there are very senior people in the room, people don't listen to a title. People listen to people who know what they're talking about, who have the experience. There's no replacement for experience. And now I think with this world of Instagram and social media where people see someone who yesterday was driving, you know, to work in a beater and now all of a sudden they're pulling up in a Bentley, that's just like being a supermodel. It's a lottery. It doesn't happen to everyone. And there's no replacement for hard work. And I think also, like, I'm just not interested in somebody who doesn't have anything to say.

35:38Like, I know how hard you worked. and there is pride and authenticity in that and you earned your position and that has staying power what doesn't is just you know the stuff that's on the surface yeah it's not that it's not that interesting at the end of the day we're all going to stop working and we're all going to be sitting next to each other at a dinner party and like i want to be somebody that people want to talk to one of the things you did at j crew was you turned at what looked like a traditional catalog into, I'd say, like a glossy magazine that showcased the brand from an entirely different perspective.

36:18It wasn't about just one piece. It was a curation of style, of identity, of color, of choices. Do you think that type of magazine exists in fashion today? I think it doesn't. I mean, from a magazine perspective, I would say magazines have shifted also in a completely different direction. I think what was nice about the catalog was that you could purchase everything and the prices were not that unattainable for a huge portion of the country. I think magazines, that world is so different. You know, I think one of the things that was really unusual is that a lot of designers started to say you can't mix clothes.

37:00So when I was coming up, I remember so vividly Teen Vogue had a really incredible stylist. And oftentimes she would take sport clothes and mix them with, you know, dress, you know, very dress up clothes. Back to the contradiction. Totally. And it was so inspiring, this idea of taking a couture ball gown and mixing it with a little Adidas sweatshirt. And, you know, it was so up my alley. And then over time, you know, because there were designers, you know, whether it would be a Ralph or a Prada, they wanted their clothing to look like it came off of the runway so that you could see what their brand was.

37:33And I understand why they're asking for that. But what it did is it sort of made it so that when you actually do a photo shoot, it's now one page is Tom Ford, one page is Prada, one page is Ralph. There isn't that mixing. And so we got to mix anything. thing. We were able to do whatever we wanted because we were all one brand. And so we were able to, I think, show people, you know, different ways to wear things that was a little bit more unexpected because we were only answering to ourselves, which was great. Let's talk about the power of social media. Is there an authentic way to use these platforms to accentuate a certain style and not just be a trend follower?

38:14When things don't feel authentic and you don't feel like you're getting a real inside piece of something or genuine conversation or point of it's so obvious it's so obvious and i think now you know it's interesting because i have a my son is is going to be 20 in a month and i can't believe i have 20 that's so weird i have 16 more years to go to that we'll talk later it goes really fast but what i i watch his connection to it and he is so discerning and so quick to say, mom, that's not real. Mom, I don't care about that. He wants to learn something and he wants to really learn something that feeds him.

38:54He's very different about his approach to social media. And I'm so happy about that because I do think, you know, I see I'll send him things and he's like, that's not cool, mom. I'm like, okay. I guess I won't do that. But he's really, he really does key into when somebody share something that feels authentic and real. He knows the difference immediately. I'm a little bit more susceptible because I think I came into it sort of midway through. Like I resisted personally for so long. And then when I did a TV show, they were like, you have to do it. And I was like, okay, so I have a funny relationship with it.

39:28But I think it's, listen, I think as AI continues to shift, it's going to take on even more of a sort of need for the authenticity that's going to become much more paramount than it is now even. I mean, who do you think is doing it well? What brands, in your opinion? From a brand perspective? I think, well, it depends on the size. I would say from a smaller scale, I think what Lila Gohar is doing, I don't know if you've seen her stuff, but I think she's a really interesting approach and it feels it's idiosyncratic and you can really see that idiosyncrasy. but very authentic to her exactly and i think you really you get a sense of her there is a a makeup artist named her name it goes by share webb who is out of england and she does these videos and she gets on she's like hello my beauties and she'll do a make and i like i find myself watching them they're you know like 15 minutes long they're so good because she's so you feel like you're in the living room with her so i think when that takes a lot of confidence by the way hello that is not i don't have that i could not no i mean she's beautiful and her makeup techniques are great you would love them because she's got your coloring so i'll oh i'll definitely yes because she's really good what i like about them is they're they're quirky and authentic and you see the personality in that and that i think is really interesting so let's shift gears and talk about the year that you left J.Crew.

40:50It's 2017 and you were nine years. Yeah, nine years. It was a big transition. Yes. And you were very honest about it. You described it as one of the most challenging, difficult periods of your career. Can you describe the first few months after leaving? I mean, I think in retrospect, I was deeply depressed. I don't think I realized at the time how, you know, ironically, I saw someone who I worked with for 17 years for breakfast yesterday morning, actually. And I realized part of what was so hard is these people had become my family. So while I lost my family, the people that I trusted, I enjoyed, I laughed with, I was fed with emotionally, I also lost my identity.

41:48I all of a sudden didn't really know who I was. I stopped getting invited to everything. I also had, you know, I had someone cooking for me every day. I had three assistants. I had a nanny. I had all these people taking care of me and all of a sudden I had none of them. I didn't need all these people. And I also was sort of like, I wanted to just be by myself. And so I, you know, I obviously had the assistant crew and then the people that were at home. And I just found myself really alone and confused about who my friends were and who they weren't. And it became very clear very quickly of who was really someone I could trust.

42:29And I think having it all fall out at once was really dark. It was dark. And also, I, you know, I didn't get a single phone call, you know, and I think people said to me, I don't believe you. But, you know, I was just talking to my friend about this yesterday morning, which was, I had become so synonymous with this brand that all of the bigger brands that could afford me didn't want me. I mean, what is Ralph or Michael Kors or Gap or Banana? They don't want me because I'm J.Crew. And they didn't want to bring in the person who was at J.Crew. Well, she's just going to make it look like J.Crew. And so, you know, on top of losing everything, I also wasn't getting any phone calls.

43:15It was scary. and I and then I separated from my girlfriend I mean it was just literally like talk about the house that I built it was just coming down brick by brick and and I couldn't really talk about it with anyone because I think most people were like oh you're so lucky you know I had a massive sevens agreement and like even though I wasn't fired I was it was an amicable negotiation and they were like you you have a non-compete you can't work anyway so well so I was in a good And, you know, I had a really good situation. So it was hard to be like, oh, woe is me. And so I was really quiet and just kind of hibernated.

43:54And it was not smart. I should have done something about it in retrospect. I really, yeah, it was dark. The thing that really touched me, what you just said, is about identity. and I can so relate to that because as a female athlete so much of your identity is shaped within the first 25 to 30 years of your life and when you come out of it and when I say come out of it it's like from one day you are a top athlete and the next day you wake up and you don't have a coach anymore and you don't have a physio you do not have an agenda you're not flying to a tournament and you just look around you and you're like, who am I?

44:43Who's with me? What am I doing? When am I starting? You have so many questions to answer. I wasn't depressed because I loved what I did for so long, but I loved it because my body and my mind was in it and my body was depleted. And even though my mind still wanted it, I was smart enough to recognize that you can't do this job without an engine and your body is your engine. And if you can't tap into everything that runs this body for you, then what do you have? Do you play tennis still? I don't. Not at all? Not like a few times. Really? Yeah. Oh, that's interesting. Do you think you'll teach your kids to he's not showing much interest i'm not kidding he's like he puts the ball away really yeah does your husband play like for fun i mean i make fun of him

45:52i remember like even now when i travel and sometimes you go to to a few countries where they still require you to fill out a form like on arrival and the very few countries that still do that and there it asks you what your occupation is and I always wrote athlete and every time I wrote it it made me feel so strong oh that's just writing out those words and I still continue to do that because I still feel that that is a huge part of my identity what did you do in the moment And how did you break through that identity crisis? Honestly, it took, I would say, over a year, almost more. And it wasn't until I started just taking phone calls and starting to think about, well, what could my life look like?

46:42I, you know, I had done everything I was expected to all of my life. I, you know, worked hard from the time I got out of college, married a man, had a baby, bought a house. Like I did the things I tried to move up in my career. And I remember really distinctly, I was like 40 years old and had a birthday party. And I had this beautiful brownstone in Brooklyn and had just been photographed in Domino magazine. And I was doing really well in my career. J.Crew had gone public. I have this beautiful little boy and a lovely husband and all of my friends in my backyard. And I remember just standing there and thinking like, I am not happy.

47:19Something was just off. And this was before I left, but I was I think there was things going on for me that I was still struggling with and didn't really I didn't know. I think I'd just done everything that everybody expected me to do and never really tapped into what made me happy. And so when no one called, I sort of realized I have this chance to try things that I probably wouldn't have tried before. I don't I would never have thought about going on TV or doing any of those things, mostly because I just assumed that I had to go and get another corporate job and, you know, work for the man, so to speak.

47:55And I mean, I could not be more thrilled. You know, I think I now a lot of the work that I do, which is consulting work, is so informed by all the different experiences I had. But I probably would never have found that if I had just gone and taken another corporate job. I would just be doing exactly the same thing in the grind. And I'm so much happier that I didn't. So you had this quiet period. A long quiet period. For a long time. Is that something in retrospect that you suggest? Or like if someone is going through a shift in their life or shift in their career, whether it's personally, professionally.

48:38I found that it was nice to take a step back and reevaluate. Yeah. I mean. But I'm hearing that it was so lonely that that also made it incredibly hard because you didn't have you didn't know who to reach out to and who to speak about it with. First of all, I agree. I think having it is a luxury, I think, from a financial standpoint to be able to take a bite, like a beat. And I feel deeply grateful that I had that time to let my mind wander and to entertain things. And I probably should have gotten help. I should have reached out and I should have had more community around me and I should have probably gone there.

49:15Like I just was not talking it out. And I, I, I should have. And I, I, so I, I think I would still, if I had to do all over again, I probably would take the time and I would give myself a little more scaffolding than I had. I really didn't, I did not see how unhappy I was and how scared I was and how lonely I was. I was just, it was lonely and it's not a lonely, like you and I are sitting together and we're having a car. It was a lonely and like, I had a huge life, a huge team and I, we laughed and I had so much fun and I loved making the clothes and I, it never got old. I just didn't want to be a manager in the way that I was at that point.

49:54I wasn't. And you go from that to sitting on your sofa alone. It's really, um, there should have been your boy's a teenager at the middle. He was, you know, I remember really distinctly when I started my own thing and we had this launch night and I could tell there was this glimmer in my son's eye. And I was like, I am so excited to see you happy. I said, what's so, what, you know, what's going on? And he's like, I'm just so happy you're back in the world. You know, it made me sad to see you sitting on the couch, mommy. And I was like, okay, I thought he would be so happy to have me around. And he was happy to have me around, but I think he was much happier seeing me be engaged in the world.

50:32And I was excited. I had something to talk about and something to share and something to make. I think there's also that part where you're creating something and you have something to show. You can show up at a match and someone can watch you play and you can actually have a beginning, middle and end to something that people can can they can process we were making all these clothes and then there was a catalog and we're like we made this thing as a team we created this and then all of a sudden I had nothing to show it was like you're walking the walk totally you're not talking to your son about it you're not talking to him about the problems about the solutions you're just you're showing up at work every day and you're showing an example and I mean I talk about this a lot with my girlfriends because we all have a version of mom guilt.

51:20Like I head out to this trip to do these recordings. You know, I drop off my son at school and I know I'm not going to be there for pickup and I'm going to miss bath time. And there is this, you know, hole in me that's like, I should be there. I want to be there. But I also have a career that I'm incredibly ambitious about. And I'm, by the way, not apologizing for it. Well, you should talk to my son if you ever feel bad. And he loves nothing more than to brag about me and to talk about all the things I do. And he is so proud. And there's never been a time where I've ever felt like he doesn't remember the stuff that I missed.

51:57When I ask him about his best memories from when he's little, he'll talk about coming into my office and getting to play with the girls who make jewelry. And he'll come coming to a fitting and getting to try on all the big coats and retaking it. You know, those are the things he remembers. you know walking into the office and everyone knew his name you know all the security guards are like hey Beck you know those are the memories that he says he has never said to me that he remembers when I went on a business trip he doesn't remember so if you need to pick me up you can talk to my son Beckett so it's 2023 and you surprise a lot of people by joining a very popular show Real Housewives of New York and then you surprise them by leaving the show two years later.

52:39Yeah. Well, talk me through the decision of going on the show. Well, I mean, I started an eyelash company, which I don't have any eyelashes because of my genetic disorder. So I was, you know, he very fortunately got into Target and they had purchased a huge number of units, which was very exciting. Over 750 ,000 units after seven months in business. Yes, we were clicking away at a very fast rate. But we were doing really well in New York and Chicago and L.A. and all the places that people really knew me from my previous life and understood what the brand was. But we weren't doing so well in some of the other states where people weren't as familiar with me or the brand.

53:17And so they had said to me, we need you guys to do some sort of national marketing. And I was like, yeah, we can't afford that. Well, this is before the show. And I was like, we can't afford that. And then through a long twist and turn, I ended up, you know, getting a call from Mandy Cohen. Would you consider? And I was like, this is the perfect avenue. It's the right audience. It is national. It is big all at once. And so... Your business hat went on. That was the reason. You know, I... What surprised you about reality TV? It's hard. I thought with all of my experience of running a company and being, you know, through a lot, we had had, I mean, 27 years, I had gone through a lot.

54:03I had seen ups and downs. I had had great bosses and terrible. You know, I had really experienced a lot of tears, a lot of heartache, a lot of very intense stress. So I was like, I can handle this. It's a bunch of women on a TV show. Like, I got this. It's not the same. I knew it was a TV show, but I couldn't help but take some of it personally. And it got under my skin. And I found myself really struggling sometimes. And I was really surprised. And it's also just hard to have a camera on you at all times in a vulnerable scenario. I don't know. I was not prepared for that part. It was fun. I'm glad I did it.

54:43I have no regrets. And it was really interesting to see the process and how it went. But it was definitely for my emotional well-being, probably. I'm just not cut out for it. You know, I don't think that I'm like. And you don't know until you try. You don't know until you try.

55:04So tell me about Fundamental Co. Sure. Because you're helping frame brand as a value creation for private equity firms and portfolio companies, which is sort of an unusual another another side yes walk me through that it was during the pandemic and I was you know we were just finishing I just finished another tv show so I'd done a tv show called stylish with Jenna Lyons this was prior to um during the housewives and I remember talking to this guy who was a dear friend um on the beach Johnny Bauer because that's where all the conversations happened and the pandemic was on the beach. And he was working at a company called Blackstone and he had established with Inside Blackstone, basically a brand sort of, what I would say is taking all the different brands they made and if they needed a carve out, if they were preparing for an exit, if they were looking for a rebrand, and Johnny would oversee that team who really re-established and rethought about what that brand could be.

56:06And so when he was doing that, He asked if I would help consult some of the companies that he was working on where he didn't necessarily have people internally who understood that world. So there was a home company. There was a fashion company. There was a beauty company. And they were all things that I had experience with. And I had never really consulted before. I had been on the receiving end of consultants. It's totally different than anything I've ever done. But I get to use my brain in a much more interesting way. And everything is different. Every company that we work with is different.

56:36Every challenge is different. Every ask is different. They're not all. And every stage of the company must be different. You know, taking a brand and and transmitting what that brand is about. The simpler, the better, the more complicated and convoluted and and laid in the messages, the more hard, the harder it is for the consumer to to understand that. And I think with age and experience comes that realization, like, don't be afraid for it to be simple, like brick to forehead. It is OK. You don't need to spin a fantastical web. What you need to do is think about like core focus, what's important.

57:13That is the nucleus of everything. And then you can go from there. Let's talk about AI. I want to pick your brain. Do you use it? A hundred percent. What do you use it for? I remember when AI first started and I was like, oh, OK, now I can, you know, change, you know, change what my countertop looks like in my kitchen and I see if I want to change the color. And I was using it, thinking about it in a very simplistic way and a very and truthfully, AI's worst trait right now is creative. It's not actually there yet in terms of the creative. It's one of the last bastions of research. And I think all these all these gyms for AI are training in fintech and finance for all the reasons we understand.

57:54And so, you know, I think what I was hoping that I would use it for isn't really what I would use it for. I think what I find it is great at for just day-to-day life, not, and I wouldn't talk about this in terms of work because I think in work we're really thinking about it in a different way. We're thinking about AI really in terms of how can you optimize or rethink what a business could be, not like making small iterative changes like data research, because that's easy. For me, it's it's I have like a well of conversations and those conversations have sort of started to get this my little cloud bot to know to know who I am.

58:32I think training your little bot to know you and, I mean, to make it more personal is honestly like, which is a little weird, scary. Well, yeah, it's the world of unknown. I did ask it to read everything about me so that it knows who I am and to understand where I'm coming from. So when it makes suggestions, it's informed. But I think having it know you a little bit and being able to actually build a structure around you so that it can make good suggestions for all parts of your life. I don't use it for anything creative as of right now because it just doesn't really have any taste. My husband makes these very funny images of like my son on a very large horse or like playful images that are so ridiculous.

59:21He has more time on his hands. Yeah, that's what I tell him. I'm like, you do the work, honey. I mean, I do really love that stuff. I mean, I think. But it's amazing how it's done in 15 seconds. It is. It's creepy. It's so creepy. It's so creepy. But how do you think AI will impact fashion? I mean, that's a good question. I think probably much more on the manufacturing side than anything else. I mean, I think I'm sure you've seen already that people are sewing and wearing cameras. And I think the actual supply chain will be much more impacted than I think we understand. There is, you know, I'm very curious to see, particularly as you get to handwork, like any sort of beading and that kind of stuff.

1:00:06I have no idea if robots or like what the future of that is. It's a little unpredictable. What about models? You know, it's interesting. I think that there will be a certain sector that will probably, you know, shift into using AI models. I mean, listen, if you look at it, as the world moves more and more online, already you see things where, you know, it's just the model's head is cut off and it's the same body. So now that you can actually start to change that swimsuit or that jean. But the fact of the matter is, I think, as we talked about earlier, the more. Like silicone the world becomes, I think the more analog and touchy people are going to be.

1:00:50I think it's interesting to talk to the younger generation. They're so in desire of authenticity. They're not embracing. They're embracing it in terms of supply chain or things being easier, but not. as much in like it it severs trust I think a lot in terms of anything creative so I I certainly hope there's no way that we will get away with it not impacting the fashion industry and models and all that I'm sure it will at a certain point but I think it's not going to be um I don't think it'll touch the create like the product being made I'm there or created I suppose time I'm saying this but like I'm like time will tell I know we can have another conversation in five years and see where we are.

1:01:34I think it's so hard to understand where it's going. What do you think of the word tastemaker? I was going to play a little game with you. It's just a few fashion choice questions and I want your take. Okay. If you've made any of them yourself. Don't worry. You won't hurt my feelings. Okay. Dress codes for weddings. Yay or nay? I okay I love a dress code and I love a theme and here's why I don't like ugly pictures I like everyone I love it when someone says please wear black and white or please wear white or please wear pink you like direction well because the photos look better I just care about a pretty photo I could give a shit where you get your clothes I don't care what you wear but just let's make the picture look good animal print on a first date you can wear whatever the hell you want on a first date.

1:02:25No rules. Really? Yeah. If you are feeling like you want to wear an animal print on a first date, like by all means, go for it. Couture on the tennis court. 100. Please. You're all for it. Please. Who am I talking to? Oh my God. Nothing would make me heavier. Karate pant for every day. I think I know the answer. Absolutely. Yes. Absolutely. I wear, I have these matto. You would love them. They would look so good on you. The matto pants? The Meadows. Do you have them? Yes. I love them. They're my favorite. I love the brand. And I get so many compliments on them and they're perfect for tall girls.

1:03:00A neutral lip since you're wearing a bright lip. My rule is a lip and no eye, eye and no lip. Oh, I like that. I mean, you can have a little bit to just give definition. I don't have any eyelashes, so I have to do something. So one or the other. But one or the other. Please, I don't want to see a red lip. I mean, unless you're like, you know, in a movie, music video or something, then you can do whatever you want. But on a day-to-day basis, I don't need to see an eye and a lip at the same time. It's too much for me. Trying too hard. It's too much for me. That's Jenna's version of trying too hard.

1:03:29What is a routine that's helped shape your success? This is a hard one. The thing that I recommend to everyone is hire people who are smarter than you and don't be afraid to hire really smart people. I think sometimes I remember really distinctly someone came in after having interviewed. Someone said, this girl could have my job. And I'm like, great, then hire her. those are the people that allow you to do more. And I think sometimes people get afraid of having people around them that could really nip at their heels. And I think it's a good thing. What is a common misconception about you? That I'm a cunt.

1:04:04I mean, we should end it on that note. But we do have two more. What is something?

1:04:15What makes you feel tough? i can't take her seriously sorry um i don't know if i ever really feel tough it's not really in my lexicon i don't i can feel confident and that would be like a five inch heel but power suit suits don't really do it it's the it's the height which i imagine you probably felt like there's something really powerful but you're already tall i know but there's something really nice about being really tall. And I remember when, I'll never forget, when we were basically going on a, when you are getting ready to IPO, you go on a tour, as you're familiar with this, and I'll never forget our CFO saying, where are the highest heels you've got?

1:05:00And I was like, okay. It impacts people the way they perceive you. It is really, and I don't know, so I love a high heel. Tough as a high heel. Love it. And what is something that makes you feel pretty? I would say when Cass takes my picture. And that is a beautiful picture. She's so talented. Thank you, Jenna. Thank you for joining our little podcast. This is not a little podcast. It's a big grown-up podcast.

1:05:35Thanks to Amazon Prime for supporting this episode. I'm an athlete, businesswoman, and mom. so I need products and services that can actually keep up with me. Prime has all the essentials to help me seize every opportunity that comes my way. No matter what your passion is, no matter what your pursuit of excellence is, Prime can keep up with you too. Visit amazon.com slash prime to find millions of items delivered fast. Same day delivery? It's on Prime. Available in select areas? Terms apply.

From the publisher

It’s New York Fashion Week, and who better to speak with than fashion icon and entrepreneur Jenna Lyons?

Maria and Jenna discuss everything from her meteoric rise at J. Crew, from assistant designer to president and executive creative director to her advice on developing personal style, why she decided to walk away from the Housewives, to complete career reinvention.

0:00 – Intro: Stepping Into Your Power with Jenna Lyons

2:15 – The Early Grind: Starting Out as an Assistant at 21

7:30 – Learning the Business Side: Moving from Design to Executive Decision-Making

13:10 – The J.Crew Golden Era: Shaping a Cultural Force and American Style

19:45 – Mastering Creative Control: Protecting Your Vision in Corporate Boardrooms

26:00 – The Cost of Perfectionism: Overcoming Burnout and High-Stakes Pressure

33:20 – The Breaking Point: Stepping Down and Navigating a Public Identity Crisis

41:10 – Rebuilding from Scratch: Finding Your Voice Outside the Corporate Machine

47:50 – Style as a Language: Why Authenticity Outlasts Every Trend

54:30 – Stepping Back into the Spotlight: Navigating Reality TV and Modern Media

1:01:15 – Redefining Ambition and Setting Boundaries on Your Own Terms

1:08:00 – Closing Advice: The One Thing Every Ambitious Leader Needs to Hear

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About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship. 

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