[00:00:00] Gayle Perry: I knew that I had to put myself in front of the camera, use the city as a backdrop, and just be out in the world. I was consistent every single day. If you believe in something that you've created or a service that you provide, stay consistent. Block out that noise.

[00:00:18] Michael Oved: At 26 years old, you were recruited by the CEO of Calvin Klein. How did you land that gig?

[00:00:23] Gayle Perry: If you can allure and create this emotion and a mood—really pull people into wanting to be a part of that world—then you've got it. You know what really helped me have the attitude for it? It's—

[00:00:39] Michael Oved: Welcome back to 30 Years in 30 Minutes. I'm your host, Michael Oved, and we've got a great episode for you today. With that, it is my pleasure to introduce to you today's guest.

Gayle Perry is a personal stylist, interior designer, and arbiter of all things style. She's the force behind the large and ever-growing platform, Gayle Style, which boasts around 500,000 followers. She's also the creator of Gayle Tuck, Gayle Tie, and Gayle Roll—style tips that help women and men look their best, feel their most confident, and be their most productive selves.

Gayle is known around the world for her innate sense of style, her keen eye for statement pieces, her creativity in high-low dress, and her ability to heal and empower through style—no matter the body type, budget, or age. Gayle, it is such an honor, such a pleasure to have you with us today.

[00:01:25] Gayle Perry: Thank you. I'm so pleased to be here.

[00:01:27] Michael Oved: So before we go into your tremendous accomplishments, tell us more about you—a bit more about your upbringing, your journey to eventually becoming one of the most influential personal stylists on social media.

[00:01:38] Gayle Perry: I came from a very large family. There are seven children. I'm the oldest of six and was a real mommy at quite a young age in a divorced home.

[00:01:50] Gayle Perry: And that really helped me gain momentum and strength in many ways. I was also bullied—and that began in sixth grade. I just remember there being a lot of tough stuff, whether it was at home or at school.

There was something that got me through those tough days. I would watch my mother when she got dressed. My mother was two things: she was a nurse and also a model. An interesting combination, because she would help heal people, and then she would also put on these dreamy outfits.

[00:02:18] I remember on some of those very tough days that I would find myself in her closet, trying on some of those pieces and feeling different. They didn't have to be expensive pieces—the ones I wore—but if it was my favorite brown corduroy or a great T-shirt, when I felt that I looked good, I felt good. And I felt capable. It was kind of like Wonder Woman putting on a cape. I felt I could get through anything: the tough stuff, being a child of divorce, being bullied in school. That's at the core of the young Gayle.

[00:03:04] Michael Oved: So you were super interested in fashion from when you were younger. How did that translate? How did you further develop those interests while you were in high school, while you were in college?

[00:03:14] Gayle Perry: I realize now—I had so much creativity in me. It's interesting because my career in fashion began on the business side, and we'll get to that in a moment.

When I look back now, I just remember that creativity got me through a lot. Whether it was dreaming up outfits the night before or even in the morning, standing in front of my closet. Or the way I would put my room together. A certain bookshelf had to look a certain way, and everything had a place. The items had to be quite special—again, not expensive, but meaningful—and they looked good.

[00:04:00] That was something that just was in me. I found through that process—whether it was putting my room together in a certain way or dressing myself—that again, it empowered me and fueled me. And it also was really exciting.

[00:04:04] Michael Oved: I mean, so that empowerment—I totally understand. That fueled you, and that truly is how a lot of people become successful. There's this interest of theirs that arises out of perhaps necessity—and they just run with that.

So I guess for you, how did running with that look like in your early days?

[00:04:23] Gayle Perry: Well, I was running away from the bullies or doing anything I had to do to stand up to them. So it really was necessity. I'm so glad you said that, because I had to get through. I had to get through tough stuff as a child of divorce, and I had to get through going to school when I was walking into a classroom and there were literally girls in the doorway who were ready to kick me on my way in.

[00:05:00] I didn't have a choice. I had to find tools. And dressing well was one of those tools that really gave me that armor. It wasn't so much armor like, “Okay, I'm going to fight back,” it was more preparedness.

And I always came from a place—I didn’t want to be bullish like them. I just wanted to be more. I in fact used to pray for them and hope that overnight maybe God would do something in their sleep and just help them be kinder the next day.

[00:05:21] Michael Oved: So how do you deal with bullies? Because there are a lot of people who encounter bullies in their life. There must be a balance that you strike when it comes to bullies. Obviously, you have to fight back—or maybe you don’t—so you don’t look helpless or allow yourself to be stepped on. What is that balance? How did you approach it, and looking back, how could you have approached it in a better way?

[00:05:43] Gayle Perry: It’s so important—we have to strengthen ourselves. I learned that as a young girl. I said, “What do I need to do to give myself the strength and the muscle to get through?” Because you have to show that you’re strong and that you're not going to take it.

[00:05:58] Gayle Perry: But at the same time, you're not going to go to their level and be a bully back. So I definitely stood up and said, “Hey, cut it out.” And I also found that I created other pockets where I could go. At one point, it was theater. And I was not meant for the stage, but I was a stage manager just to be part of the theater.

[00:06:23] Gayle Perry: It’s so important. I have younger kids, and I tell them: give yourself the strength that you need, and then go find other avenues. Find your people. I only needed one person, and I found that person in the theater program in high school.

[00:06:43] Michael Oved: That’s wonderful. And it’s so interesting to me that you mentioned theater and performances as your outlet, because for me—I’m a classically trained pianist and guitarist—whenever I was dealing with something, I always used to default to “Let me play the piano, let me play the guitar.” So it’s wonderful to hear you say that.

[00:07:01] Michael Oved: Moving on to your college years. So in high school, you developed your interest in fashion. You kind of saw it as an outlet that you could go to. And then in college, how did you approach fashion?

[00:07:13] Gayle Perry: It was so exciting for me. I had the opportunity to move away from a place where—while I had the most amazing family and so much love—any divorced family is hard. I knew that once I got away, and also being so responsible for younger siblings, it was finally my time.

[00:07:23] Gayle Perry: And I also—because I was going through so much in junior and high school—I couldn’t apply myself academically. And I’ll tell you, back in the day with the Barron’s book, when you were looking at what schools you could get into, the section I could go to was “less competitive.” I couldn’t even go to “competitive.” But I didn’t let that hinder me from knowing that I could do good things in life.

[00:08:00] Gayle Perry: So I saw it as an opportunity—let me get away, let me really focus on me and my interests. I didn’t know at the time, initially in college, that fashion would be my career. I just knew that no matter what, I was always going to present myself in a meaningful and thoughtful way. Because when you make that impression on others, it builds confidence.

[00:08:20] Gayle Perry: I always did that. I was the girl who—even during final exams—showered and got dressed. I didn’t roll out in my sweatpants because I knew if I was dressed and showered, I would do better. But the fashion stuff came a little later.

[00:08:43] Michael Oved: I think it’s super interesting that you spoke about not being able to apply yourself academically, and then when it came time to apply to colleges, you weren’t ready for that. A lot of our viewers—most, actually—are people who are still in school, getting ready for their lives, really excited about their future. And a lot of people—most, in fact—aren’t able to attend those prestigious institutions.

[00:09:04] Michael Oved: From someone like yourself, who’s accomplished so much—yet, as you said, you had trouble performing academically—is it still possible to be successful if you’re not academically successful? And how can you offset that in the real world?

[00:09:20] Gayle Perry: I mentor a lot of young people, and I love sharing my story. That’s why I was really honored and thrilled to talk with you today, because I do have a story. I could have easily been demotivated, knowing I couldn’t go where my friends were going—to higher institutions, more competitive schools.

[00:09:32] Gayle Perry: But I said to myself, “I have an opportunity here. I’m going to get the best education that I can and work really hard.” And I knew that would give me opportunities I didn’t yet have. I love telling my story because I had so many obstacles, and I worked really hard in college. I transferred. I did better at the next school. And I’ve had an incredible and meaningful career that I’m so grateful for.

[00:10:08] Michael Oved: And I think as we go through your career, the key that’ll emerge—the string that will run through it—is resilience. Even looking at your schooling… going back to my question, when you don’t have the academics to succeed, is success really just a function of hard work? You’ve got to get down, get dirty, be willing to work harder than anyone else. Is that really what success is, independent of academics?

[00:10:29] Gayle Perry: Believing in yourself. Doing everything you can to convince yourself—but also to show people. I had a professor who said, “An A here is going to be a C where you’re going.” And I said, “Watch me.” So yes—the hard work is really, really important. And not taking no for an answer.

[00:10:50] Gayle Perry: There’s always a way. I would say to myself, “Just watch me. Watch what happens.” I gave myself the inner pep talks I needed to stay on course. Be consistent and work really hard. But believing in yourself is so critical—and not taking no for an answer. It begins at “no.”

[00:11:13] Michael Oved: I even told you this the last time we spoke. A quote I live by is: attitude is altitude. Your attitude will determine how high you go.

[00:11:26] Michael Oved: I’m sure for you, when you were breaking into the fashion world—which is not easy—it probably was, in large part, a function of your attitude. Which I actually think is the hardest part about success: having the right attitude. Can you tell us a little bit about how you broke into the fashion world? What attitude did you need to have?

[00:11:42] Gayle Perry: What really helped me have the attitude for it was dressing the part and assuming the role before I was there. I speak about this at colleges, universities, corporations, banks, law firms: assume the role.

[00:12:00] Gayle Perry: That really helped me believe I could do it. And the reason I started a business that is accessible—no matter body type, budget, or age—is because you can do it. You don’t need a certain income level or body type. Style is accessible.

[00:12:12] Gayle Perry: So I assumed the role before I had it. And when you show up that way, it fosters confidence—and people have more confidence in you. They give you a chance.

[00:12:26] Michael Oved: Tell us a little bit about the first chances you had as a result of that confidence. You started your career at Donna Karan. Can you tell us how you got that gig and what that experience was like?

[00:12:38] Gayle Perry: I graduated with an English major—and I tell everyone, don’t be afraid of an English or liberal arts degree. Being able to communicate and write has really served me.

[00:12:48] Gayle Perry: I was working at a legal publishing house reporting on food labeling law—companies that were misleading the public. But our division folded. I lost my job. I was 23, living in a walkup with a roommate, rent was due. What was I going to do?

[00:13:08] Gayle Perry: I went to the New York Times—back when we still went to the newspaper—and found a headhunter ad for advertising. I called him, and he said, “I’m sorry, I don’t speak with English majors.” I said, “Speak with me. I want advertising.” He said, “Okay. Thursday at two.”

[00:13:29] Gayle Perry: I was in his office and told him, “Look, I’ll do whatever I need to do. I need to work in advertising.” I started working for Donny Deutsch. It was amazing—new business. I was fortunate because my aunt worked at the New York Times and knew Donna Karan needed an associate media director.

[00:13:48] Gayle Perry: She called me. I was literally in the closet—sorry, Donny—but I was hiding at Deutsch Advertising, and I said, “Yes, I’ll be there.” So it started for me at 23.

[00:14:00] Gayle Perry: I absorbed everything I could—whether I was researching bath products to pitch The Body Shop, picking up dry cleaning, or ordering pizza for a meeting at midnight. I was so happy to be in the room. I read every fax I sent. I just wanted to learn.

[00:14:16] Gayle Perry: It was exciting to me. I always believed I could someday be in the role of the head of the company. I saw that for myself. I was in those rooms with some of the best creative minds, and I know that helped me build my business.

[00:14:39] Michael Oved: I think something you said that really stood out to me is the importance of just being in the room. When you're in the room, you're exposed to so much—you’re exposed to knowledge, to where the decisions are being made. Hearing that is empowering, especially for someone like me who's figuring out what comes next in my life.

[00:15:02] Gayle Perry: I tell a lot of young people today who say, “I just want to go out there now and either be a stylist or have my own company,”—and I say, “You know what? If you have an opportunity, even if it’s not exactly what you envisioned, take it.” One woman once said to me, “I just don’t really want to be at Ralph Lauren looking at fabrics.” And I was like, “Are you kidding me? You’re at Ralph Lauren, looking at fabrics!” Even if you don't want to be in that division—get there, go do that.

[00:15:23] Michael Oved: So in your early days at Donna Karan—and for those listening who don’t know, Donna Karan is a very successful designer and the founder of DKNY—what were the important lessons you learned from watching how she ran her business? What did you take from her day-to-day routines, her mindset?

[00:15:45] Gayle Perry: Certainly, the way she cared for women and approached empowering them through style. That’s something I still use all the time—understanding what works best on a woman, and on a man too, because I style men as well.

[00:16:00] Gayle Perry: But even more than that, I learned how to communicate a message and build a brand. When you put content out there, it has to do three things: it has to allure, it has to be relevant to the audience you're serving, and it has to provide a service. There has to be a reason. Donna’s philosophy—especially with in-store events—was always, “Make it a destination. Give people a reason to come to you.” That’s what I do on my Instagram. I try to provide a service, make it a place, a destination—with relevance—and help people.

[00:16:37] Michael Oved: I want to go a bit deeper into that. How do you allure? How do you stay relevant? And how do you provide a service?

[00:16:46] Gayle Perry: Sure. For instance, being around some of the most creative minds who were developing ad campaigns taught me that I had to put myself in front of the camera. I had to use the city as a backdrop—Bill Cunningham, Scott Schuman… street style was always the most inspiring to me.

[00:17:00] Gayle Perry: I would dream up outfits and get out on the street. To me, New York City is the grittiest, coolest, most beautiful and spirited backdrop you could have. And I was out in the world, every single day, no matter the weather. I’d show what I was wearing and the inspiration behind it. That inspiration actually came from a colleague who once said, “I stand in front of my closet trying to remember what you wore.”

[00:17:36] Michael Oved: For people who want to start their own fashion label—and you've gotten to know Donna Karan really well—what advice do you have? There are so many steps in that process. What's the most important thing to do first?

[00:17:52] Gayle Perry: Get as much experience as possible. Fashion school is incredible, but even if you can’t do that, get an internship with a designer. Just be in the room and gather as much as you can. And also, start creating things—for yourself, for friends.

[00:18:09] Michael Oved: When you’re getting that experience, what questions should you ask? What should you strive to learn? Because it’s one thing to say, “I’m going to intern with a stylist or at Ralph Lauren,” but what’s the most important thing to focus on while you’re there?

[00:18:30] Gayle Perry: Ask questions. I remember when interns or entry-level folks would ask how I got there—because I went from Donna Karan to Condé Nast, to a number of magazines, and helped build style.com. I’ve done a lot of entrepreneurial things, and I was always surrounded by amazing people.

[00:18:45] Gayle Perry: And I loved when young people would say, “Gayle, how did you do this?” Because we all had people who helped us. So ask questions. And don’t be afraid of the grunt work or the process along the way. It might feel annoying at the beginning, but when you’ve taken care of every step and been in those early roles, that experience will matter.

[00:19:13] Gayle Perry: Later, you’ll be able to say, “I started here. I did this. I was in those rooms where X, Y, and Z happened. And now I’m doing it on my own.” That’s a big deal. That’s résumé-building. And even if you’re not in the exact department you want yet—that’s okay. Remember that word: yet.

[00:19:47] Michael Oved: Taking a step back—you started at Donna Karan at 23. And then, at 26 years old, you were recruited by the CEO of Calvin Klein to run their entire media department, managing their entire U.S. advertising budget across all divisions. That’s a very impressive gig to land at 26. How did that come about?

[00:20:11] Gayle Perry: It was so exciting. The industry had a lot of young people in key roles, and I had made a name for myself. My job was to buy the advertising in magazines—back when magazines were king and queen. If you were in Vogue or advertising in Vogue, that’s where people got their influence.

[00:20:28] Gayle Perry: I became close with the publishers and had a reputation as a strong negotiator. I remember bosses saying, “Don’t be fooled by Gayle. She may show up looking the way she does—so beautiful, so kind—but beware. She’s strong. She’s a fierce negotiator.”

[00:21:00] Gayle Perry: The CEO of Calvin Klein saw that I could get the prime real estate in the magazines for Donna, and that’s what they wanted. And I was really good at it. It was hard work. There were tears. These companies are tough places to work—with all due respect—because the work is hard. But the tough stuff brings the glory.

[00:21:34] Gayle Perry: It was like business school for me. And from there, as you know, I left to help launch a technology company that made magazines interactive—moving toward digital. I was always the person to say, “Of course, I’ll roll up my sleeves and try it.”

[00:21:38] Michael Oved: And so at Calvin Klein, you got the role partially because of your negotiating skills. What would you say is the most important thing in negotiation? And how do you develop that skill?

[00:21:49] Gayle Perry: Listen. Just stop talking and listen.

[00:21:54] Gayle Perry: When you're presenting something—whether it's an idea on paper or in conversation—you need to hear the thought process of the person you’re speaking to. You need to hear their objections. Too often, we’re focused on listing all the benefits, saying “This is why it’s great,” and, “Here’s how I understand your business.” Just listen.

[00:22:17] Gayle Perry: Then take a pause and address the concerns or obstacles they raised—speak to what they consider benefits. Show them you’re really there to listen. That makes a big difference.

[00:22:34] Michael Oved: We had the founder of SparkNotes on a few months back, and he said something very similar. He said when you’re negotiating, it’s important to be the last person to speak in the room. Would you agree?

[00:22:45] Gayle Perry: I would. First, you want to hear what someone likes about your product or service, what their challenges are. People need to feel heard.

[00:22:56] Gayle Perry: Then you can craft your response. You’re in charge of your business. You know how to work around obstacles because you have the solution. So be solution-minded. And really—who doesn’t love a solution-minded person?

[00:23:18] Gayle Perry: I remember when I was in sales—or even when I was buying—it was so important to be solution-oriented, consultative in your pitch, and collaborative in how you engage.

[00:23:26] Michael Oved: Having been exposed to so many ads—and having been so instrumental in analyzing them while you were at Calvin Klein—what makes a good ad?

[00:23:36] Gayle Perry: If you can allure—create an emotion, a mood—and really pull people in, make them want to be a part of that world or feel a certain way, then you’ve got it. That’s what I try to do in building my business and putting myself out there.

[00:24:00] Gayle Perry: But I brought it down a notch—made it more accessible. Fashion ads for Donna Karan, Calvin Klein, Vogue—they’re aspirational. And I wanted to balance that—be aspirational, yes, but also be someone people can relate to. Like a friend in your life.

[00:24:30] Michael Oved: After you left Calvin Klein, from 2006 to 2011, you helped build style.com, then you launched DuJour, revitalized The Village Voice, and grew Gallery Magazine. How did you get those gigs? Where did that entrepreneurial drive come from?

[00:24:54] Gayle Perry: Like I said earlier—when I encourage young people to take a great job, even if it’s not exactly where they want to be yet—I did the same. In every job, I made a point to get to know as many people as I could. And I made sure they felt better after having met me.

[00:25:05] Gayle Perry: Whether it was the early days when I said, “Sure, I’ll get you a coffee,” or “I’ll fax that for you,”—or later, when I was leading meetings—I always focused on making people feel good. That goes a long way.

[00:25:33] Michael Oved: So what goes into building a magazine?

[00:25:35] Gayle Perry: Once you build a reputation for yourself and people know that you’re the one who can help them build their business or take it to another level, then that’s what happens. There’s so much that goes into it, whether it’s the editorial side or creating the amazing content.

[00:25:55] Gayle Perry: I was lucky that I got to really spend time with the editorial side, which I loved as an English major. That’s what really inspired me to go from buying advertising for Donna Karan and Calvin Klein to selling it, because the notion of showing up in a meeting and explaining why the content made the most sense and was most relevant for a designer or a brand was so exciting to me.

[00:26:20] Gayle Perry: Having that conviction as to why there was brand synergy—that was always really important to me. On the editorial side and the business side, it was about coming with the right ideas. Ideas that were going to help scale business and further build their brand identities.

[00:26:41] Gayle Perry: I was very instrumental in helping print-minded CEOs of fashion houses understand that soon enough—and this was back in ’99, 2000—people would buy clothing online. I can't tell you how many CEOs said to me, “Gayle, I have no idea what you're talking about. I trust you. Here's my money.” If you can come from a place of being educated and consultative and really understand your business, people will want to go there.

[00:27:08] Gayle Perry: It was very exciting to really have a sense of both sides, and that's what I became known for. So I encourage young people: become known for things. Work really hard, and you will become known for things. You'll be the one who is thought of when there is a position to fill because you are so valued, you are needed, and you will make an impact.

[00:27:33] Michael Oved: I think that lesson—and those lessons you learned along the way—you inevitably took in the fall of 2016 when you launched your own style blog, which on Instagram is @GayleStyle and has close to 500,000 followers. Why did you create that account?

[00:27:49] Gayle Perry: I was working at the Village Voice, and a colleague said, “Gayle, I stand in front of my closet every night and try to remember what you wore that day because I want to copy it.” I loved that. I always knew that I inspired people. They would ask where I bought something or what they should wear. And my best friend said, “Gayle, listen to the universe. Everywhere you go, you're being asked these questions. You've worked so hard for all these other companies—do it for yourself now. Build your own.”

[00:28:18] Gayle Perry: I was newly divorced—this was about nine years ago—with a four- and a seven-year-old. I wanted more flexibility in my schedule. I said, “You know what? I'm just going to work really hard and try this.” I remember how scary it was—literally picking up my wobbly knee, one foot in front of the other, and just keep going. It was very exciting. It was scary, but with that fear comes excitement too.

[00:28:45] Michael Oved: And what were the initial challenges you had that made your feet wobbly? What were the challenges you faced while building your social media presence?

[00:28:55] Gayle Perry: There were naysayers. I created the Gayle Tuck. And even to me, it sounded so weird. I was like, “The Gayle Tuck? I don’t know.” But I believed in the magic of it. I believed that no matter your body type, if you taper and tuck, you provide a lengthened, more polished, and slimming appearance. That was something.

[00:29:20] Gayle Perry: In time, I would say it and say it. And I knew there were naysayers—even some friends who were kind of nasty in their comments about me putting myself out there, saying it was a bit narcissistic.

[00:29:33] Gayle Perry: But I learned from all the places I’ve worked that if you want to build something, you often have to put yourself out there. I'm so glad I did, because now I’ll be in an airport and have entire families run up to me—not just the woman who’s wearing the Gayle Tuck, but down to the children.

[00:29:54] Gayle Perry: "We're all doing the Gayle Tuck," or "We're all doing the Gayle Tie." And so I stayed really consistent. Naysayers are hard—they make you question yourself. They really do. They get at your core. It's hard. But, like I said before, if you believe in something you've created or a service that you provide, stay consistent.

[00:30:16] Gayle Perry: Block out that noise and say to yourself, “Just watch.” And that’s what happens. Some of the people who were quite unkind in the beginning have since said, “Wow, the Gayle effect is big.” Now they get the Gayle Tuck and all the things.

[00:30:32] Michael Oved: What is the key to blocking out those naysayers? Because I think it sounds really great, but it’s so difficult to actually practice. When you're in the moment—and you’ve experienced this and endured this—that’s why I keep saying the string that ties everything you’ve done together is resilience. No matter what it is you did—whether it was in high school with the bullies, or later in your career when you had to tell your boss, “Let me show you,” or here, when you had to experience and endure the naysayers—what’s the key to dealing with them?

[00:31:04] Gayle Perry: It’s what you said earlier—it’s necessity. I didn’t have a choice. I always saw a better way. I always saw myself doing greater things. I had already left those companies. I committed to doing this. I had to do this. I had to stay consistent. It is hard—and I’ll be the first to say it—but it’s essential. And there are tools to do it.

[00:31:31] Michael Oved: What are those tools?

[00:31:32] Gayle Perry: The tools are yoga, meditation, journaling. If you’re feeling like someone’s telling you they’ll never buy your belt, or your bag, or use your service, or hire you—write down all the reasons why they should. Why would you hire yourself? Why would that item enhance someone’s life? That’s really powerful.

[00:31:53] Gayle Perry: Also, bring a tribe around you—a sister, a best friend—and keep going to them and sharing. They’ll lift you up. If you have your tribe—and most importantly, you are your tribe—give yourself the tools. Put the oxygen mask on yourself so you can stay focused in your business, because what comes from that is so much personal glory.

[00:32:18] Michael Oved: Yeah. That oxygen mask metaphor—it’s such an amazing one. The airplane always says, if the plane is going down, put the oxygen mask on yourself before you help anyone else. Because if you don’t help yourself, you can’t help anyone else. I really like that you brought that up—I'm sure that’s exactly what you were thinking.

[00:32:40] Gayle Perry: When I was younger, I didn’t understand that term. I thought, “Wait a minute—if my mother sees me not being able to breathe, why wouldn’t she put it on me immediately?” But now, I encourage women and men around the world to be their best selves, so they can better help others. And they can’t do that until they put the oxygen mask on themselves first.

[00:33:02] Michael Oved: Moving to your content creation—just a quick question. You have a lot of engagement, which is wonderful, but what’s the key to boosting engagement?

[00:33:11] Gayle Perry: Being accessible to people. I remember early on, some women would say, “Who’s ever going to follow your tips if they don’t look like you?” But I make sure that I come from a place of always wanting to help.

[00:33:25] Gayle Perry: Also, I share my struggles—my hardships, my pain. If I can talk about the tough stuff I’ve been through, it normalizes it for others. They might say, “Wait, she just opened up about that? I didn’t know she was divorced. I didn’t know she was bullied all those years.” I will be writing a book, because there’s more in that equation to share. I do it because I think it really helps others.

[00:34:03] Michael Oved: Accessibility, but also being consistently accessible. Don’t give up when you’re getting 100 views. If your content hits the right niche—whatever that niche is—it’ll grow.

[00:34:15] Gayle Perry: I’m glad you said that. There have been times when I’ve said, “Oh my gosh, that reel hardly did anything,” or “Maybe they didn’t like how I wore that.” But just keep going. Not everyone is going to love what I do every time, but stay consistent. There’s a reason people are following along. Keep giving them what they came for.

[00:34:42] Michael Oved: In addition to your Instagram account, you also have a personal styling brand. You spoke a little bit about what goes into styling people—but what does go into it?

[00:34:53] Gayle Perry: Less in your closet. More of the right things. Get more mileage out of your items. Clear out the noise—the items that represent a time in your life that was sad, like something that no longer fits, or something from a divorce. There’s no reason to keep items that make you feel bad. Clear them out. Have less. Know that every item in there is great, and then everything will mix and match more easily.

[00:35:19] Michael Oved: If you’re looking at what I’m wearing now, and I asked you, “Hey, can you style me?”—what would you say about my outfit?

[00:35:25] Gayle Perry: I would say there really isn’t a need here. You’ve definitely nailed it.

[00:35:30] Michael Oved: I appreciate that. So moving on a little bit—to you. I know we’ve spoken a lot about the advice you have, but can you tell us more about you—about the Gayle Perry behind the screen?

[00:35:42] Gayle Perry: The Gayle Perry behind the screen is so in love with being a mom. I couldn’t wait to be a mom. I’m the oldest of six. It’s the hardest job in the world. It’s the most rewarding. It is such a privilege. I get so much joy out of it.

[00:36:00] Gayle Perry: I love to read—being a literature major, I’ve always loved to read. I love film and theater. I love to travel. I had the courage to leave GQ Magazine and spend a year and a half living and traveling abroad. I love being out in the world, finding inspiration in other cultures.

[00:36:20] Gayle Perry: I value time with family and friends, and I’m just grateful that I’ve had the opportunity to build a business that allows me to be the best mother I can—and give my kids a life that’s meaningful.

[00:36:36] Michael Oved: Is there something your followers don’t know about you?

[00:36:38] Gayle Perry: Here’s one for the young people: when I had my interview at Calvin Klein, I was stressed out. I didn’t own anything Calvin Klein. I called a dear friend and wore her Calvin Klein coat—and I didn’t take it off for the entire interview. That morning, I danced in my kitchen to Macy Gray at full blast to take the pressure off. And that really helped.

[00:37:01] Michael Oved: Sometimes you’re the only person who can hype yourself up. Totally. So—what’s next for you? I mean, you’ve accomplished so much, and you wear 15 billion different hats. I have no clue how you do it. But what’s the next chapter?

[00:37:22] Gayle Perry: In 2019, I added interior design to my portfolio of services, and I’ve really taken my interior design business to another level. I started out doing full-scale properties, but now I’m working on larger, custom projects—really incredible work.

[00:37:43] Gayle Perry: I’ve also started to incorporate that into my platform because it’s really a Gayle Style lifestyle approach. And under that umbrella, a TED Talk is like my dream. I really—if anyone is listening—

[00:37:58] Michael Oved: TED Talk!

[00:37:59] Gayle Perry: I have a TED Talk that is just bubbling over.

[00:38:04] Gayle Perry: And a book—for sure.

[00:38:07] Michael Oved: I think it’s so important to get your message across because—look, I’m speaking as a 21-year-old, I’m speaking as a Harvard student—your message is so powerful. To hear from you that no matter what failures you endured, no matter what obstacles you came across, you came out more successful than you were before.

[00:38:24] Michael Oved: You stayed true to yourself, to what you believed in, and you got stronger in what you believed. You just kept going. And I think that’s the perfect segue into this question we ask every single guest. After this, we’ll move on to rapid fire. Based on your experience—your many successes and your failures—what would you tell the next generation about how to best prepare themselves to succeed?

[00:38:55] Gayle Perry: Be open-minded. Be hardworking. Be optimistic—people want optimistic people around. And be grateful.

[00:39:04] Gayle Perry: I always was. I took none of it for granted. When someone’s applying to work with me—as an intern, for example—if they come across with real positive energy and they’ve done their homework, that goes a long way. If someone presents why they want to work with me, or in my field, I want to know they did a deep dive and really understand it.

[00:39:27] Gayle Perry: That’s just great preparedness for anything in life. Stay committed. And listen, so many people have been through tough things. It’s not easy for students today. It wasn’t easy for me. And Michael, I really appreciate the chance to lend my voice and my experiences—and the hard stuff—to your audience and to young people, because there is such a need right now.

[00:39:51] Gayle Perry: I have such a soft spot. I always say that if I’m not giving, I’m not living. And it came from necessity. It saved my life to help others. So I really appreciate the opportunity to do it.

[00:40:01] Michael Oved: Of course. And now onto the rapid fire questions. What book do you recommend?

[00:40:06] Gayle Perry: Tipping Point.

[00:40:07] Michael Oved: What has been the key to your success?

[00:40:09] Gayle Perry: Hard work. Grit. Don’t give up.

[00:40:12] Michael Oved: What is your biggest regret?

[00:40:13] Gayle Perry: Not starting my own business sooner.

[00:40:16] Michael Oved: What is a quote that you live by?

[00:40:17] Gayle Perry: If I’m not giving, I’m not living.

[00:40:20] Michael Oved: You spoke a little bit about your interior design business. What is your favorite home style?

[00:40:25] Gayle Perry: Modern but comfortable. Transitional—not too modern. Lots of textures, visual interest, and beautiful color palettes—very similar to how I dress. A mix. It’s really important to balance masculine and feminine.

[00:40:39] Michael Oved: Who is your inspiration?

[00:40:40] Gayle Perry: Kelly Wearstler—her approach to style, whether it’s in how she dresses or the spaces she designs.

[00:40:48] Michael Oved: And what’s one piece of advice you would give your younger self?

[00:40:52] Gayle Perry: Breathe. I know it sounds simple, but when I was younger—and even now—just taking those moments to breathe helps reset. The tough stuff and the pain don’t define us. They can fuel us. They can be the launchpad. When you turn pain into purpose, there’s so much glory that comes out of it.

[00:41:12] Gayle Perry: I know it sounds easier than it is. It’s really hard. But it can be done. I’ve had so many obstacles in my way, and I’m sure there are more to come. That’s life.

[00:41:27] Michael Oved: That is so powerful. That is so awesome. It has been such a pleasure speaking with you and having you on the podcast. Thank you so much for joining us today, Gayle.

[00:41:36] Gayle Perry: Thank you.

[00:41:37] Michael Oved: Thank you for listening to 30 Years in 30 Minutes. Don’t forget to like and subscribe, and let us know in the comments if there’s anyone else you want to hear from.