Brittany Cobb: Founder & CEO of Flea Style

Episode 802

On today’s episode, we welcome Brittany Cobb, Founder and CEO of Flea Style and author of the forthcoming book How to Style a Hat — a modern style guide and cultural manifesto centered on confidence, authenticity, and self-expression. What began as a small, underfunded side project rooted in Brittany’s love of flea markets and vintage culture has grown into a nationally recognized experiential retail brand valued at over $15 million, with seven locations redefining how people shop and connect with personal style.
Brittany’s path to building Flea Style was shaped by her early career as a lifestyle journalist and her instinct for storytelling — skills she seamlessly translated into entrepreneurship. Long before the shop-small movement gained momentum, she created a brand that celebrates individuality over trends and emotional connection over fast fashion. From launching The Original Hat Bar, an interactive concept that transformed hat shopping into a creative experience, to expanding into hospitality with in-store cafés and tearooms, Brittany has consistently pushed the boundaries of what modern retail can be. Her personal journey with melasma further deepened her belief in style as a confidence-building tool, inspiring both her brand ethos and her upcoming book.
In this episode, Brittany shares what it takes to build a category-defining brand from the ground up, why experiential retail is more relevant than ever, and how personal style can shape identity and self-expression. We talk about turning adversity into creative leadership, building emotional resonance in business, balancing the many roles of founder and mother, and scaling while staying authentic. A thoughtful conversation for founders, creatives, and anyone looking to lead with originality and confidence.

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Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone and welcome back to the Kara Goldin show today. I’m so, so thrilled to be joined by an incredible, incredible founder who is also the CEO of this great brand, and it’s called FleaStyle. And if you are not familiar with FleaStyle, you are going to be so excited to hear all about this. You might notice that I have this incredible hat on, which is kind of a prop part of the brand of FleaStyle, but we’ll get into that a lot more. But Brittany is also the author of the forthcoming book called How to Style a Hat, which is coming out in April. Cannot even wait for you to read it, but it’s a modern guide centered on confidence and authenticity and self expression. But Brittany is a creative entrepreneur who has transformed a small, underfunded side project into FleaStyle, which is a nationally recognized experiential retail brand, now valued at millions and Millions of dollars, with nine locations, mostly in Texas, around Dallas, but also in many other locations, including Louisville and Nashville and some of the others on their website, but rooted in her lifelong love of flea markets and vintage culture and Storytelling, Brittany built the brand well before the rise of the shop. Small movement from launching the original hat bar, an interactive concept that revolutionized how people shop for personal style, to expanding into hospitality with cafe and tea room. Brittany has done it. I think all I mean you, you have just absolutely killed it. So I’m so excited to talk with Brittany all about building a category, defining brand, what she has enjoyed, what has been hard and overall, how is it going? So very excited to have you here. Brittany, so nice to meet you.

Brittany Cobb 3:05
Thank you for having me and so nice to meet you too.

Kara Goldin 3:08
Absolutely so for listeners just discovering FleaStyle, how do you describe the brand and what makes it different from anything else out there that one might encounter around hats.

Brittany Cobb 3:23
Well, that’s a long question, because we’ve been around now 16 years, and we started as something very different than we are today, which I think is a common founder story. You know, you kind of figure things out and evolve with the times, especially when covid is kind of in your timeline. But the name FleaStyle started back in 2009 when I started as a flea market, I started as the Dallas flea and the Houston flea and was hosting these pop up events all over Texas. And so flea market was a huge part of the story and the name because of what we were doing as it evolved and it became more of a retail experience, because people wanted to shop it more than, you know, once or twice a year, FleaStyle really stuck today. We still carry items from flea markets. I personally collect. We work with makers from all over the country to bring their goods, whether they’re handmade or collected, but we’ve really evolved into an experiential retail outpost where you can make things that are one of a kind to you, hats being the number one thing we offer. And so it’s, it’s kind of a long story, but it’s a huge part of our story. And something important today that I’m always involving flea market finds. It’s evolved into the original hat bar, which we founded way before they became popular. And so now those flea market finds are decorating hats and making these beautiful one of a kind style pieces.

Kara Goldin 4:41
I love it. So for those who might not have an opportunity to go to one of your locations, can you describe exactly what they’ll find? And I it’s probably different than how it all started 16 years ago. But what is the promise to consumers today?

Brittany Cobb 5:00
So when you walk into a FleaStyle store, you’re going to instantly be inspired by our decor, the vibe, the feel we’re all about, vintage finds, bringing you into a residential feeling. It feels like your cool aunt’s home or a space that you kind of want to move into. The whole thing is built around my love for design, interior design, and it really makes you want to hang out and linger. From there, we have beautiful women’s apparel and jewelry and all sorts of interesting goods, but we’re really known for our original hat bars, which are inside every store. They typically take up at least half of our spaces. And you’ll select the hat of your dreams, and then we have 1000s of items to decorate them with, and so it really becomes this experience. It’s a place for core memories and to have a lot of fun and build something that’s totally you

Kara Goldin 5:51
were you always into hats growing up. Or how did this idea all come about? Beyond the flea markets, I feel like there has to be a big personal story in the background that you said everyone needs to have the right hat.

Brittany Cobb 6:07
Yeah, so I think so many founders are answering a question or a need that they personally have. For me, it was about hats. I have a skin condition called melasma. It’s a very common skin condition, but something that I need to protect my skin every single day. And so growing up in Southern California, I was always in the sun. I was a big athlete, played water polo softball, so I always had to cover my skin. And at the time, there just weren’t great hat options. I mean, you had a couple, and you know, target or your favorite little stores, but they were not like they are today. And so to make them unique or not, wear the same thing over and over, I would decorate my hats. I would put a ribbon around it, or, you know, a brooch that I collected at a flea market, or whatever it may be. And people started to notice, and it was really in covid, where we were all, you know, maybe not washing our hair as often or wearing a hat all the time, because we were home a lot more, and people were wanting me to help bring their hats to life because they were sick and tired of the same thing. And it’s really grown organically, but it totally stems from my need to wear one every day.

Kara Goldin 7:09
I love that. So you launched the business before the concept shop, small movement gained traction. Did you feel ahead of the curve at the time? I mean, was it a little lonely out? There were people saying, What are you doing starting this company? Yeah.

Brittany Cobb 7:28
I mean, back in 2009 I was a journalist, so I was covering and I was covering all lifestyle sectors. So, you know, I meet a cool shoe maker, jewelry maker, a baker, and they were also interesting, making unique things. And it’s how I was kind of collecting for my home or, you know, getting things that were interesting for a dinner party. And people were noticing, but they couldn’t go shop them like I could having the access as a journalist. And so I decided to put them under one roof, and I called it the Dallas flea at the time, inspired by the flea markets I grew up going to in California, but also I was just moving back from New York, where I watched the Brooklyn Flea really take off. And you’re right, there was nothing outside of that, and especially in Dallas, which is shiny and new and very you know much about kind of more of an elevated shopping experience. So it was definitely against the grain. But people loved it, and it was early on in the shop, small movement. I’m really proud of how many makers we’ve supported, I mean, 10s of 1000s over the years, and it’s a huge part of our DNA. Still today, we carry tons of them in our stores. We still can sign with them. We host pop ups at our stores. It’s important to me to always stay connected to the makers and shakers. So you

Kara Goldin 8:37
went from being a lifestyle journalist to actually starting a a company that had a lot of physical goods, very different than what you had done. Where did you get the courage to just say, I need to just go do this?

Brittany Cobb 8:59
Call it courage. Call it maybe naivete. I don’t know. I think that’s part of it, right? You don’t know what you don’t know. And so you just kind of for me anyway. Go for it. It was like, What do I have to lose? Um, I was again, solving a problem that I personally wanted in my life. I wanted to shop unique people, and so I was just gonna throw the spaghetti see what stuck. I’m really glad that it did. But, you know, I think courage maybe a little crazy, maybe a little just not knowing the outcome, but it helped me kind of figure it out, and also give myself grace for all the stumbles along the way. And you know, I wasn’t trying to do it perfectly. I was just trying. And I think my, one of my favorite sayings is just do it, or just start, you know, you just have to kind of get one foot in front of the other, and then figure it out and grateful. I was in my mid 20s. I didn’t have a whole lot to lose. I didn’t have a family I had to feed, and just took a shot.

Kara Goldin 9:54
So you launched your first location in Dallas.

Brittany Cobb 9:58
Yes. So first location was. Right my backyard.

Kara Goldin 10:01
And what was the point where you said, this can be more than that one location?

Brittany Cobb 10:07
I think you know, the first show was an instant success. We had a line around the curb. It was very obvious. People were craving this experience. I was as well. So I knew it was worth doing one more than one show. When I launched, I thought it would be a Holiday Market, and that was it. That was it. Crazy story. Actually lost my job the week before with my journalism job, so it also gave me the kind of chutzpah to figure it out, because I didn’t have something else, you know, full time. But as far as the retail piece goes, I really, I’ve always listened to my customers. You know, journalism 101, is to stay curious, and so to be listening and asking questions. And that’s always been a huge part of my founder story. And so they were saying they wanted to shop it more. You know, it was one time a year, then two times a year, then quarterly. And it was like, okay, they keep wanting this. I think retail is the answer. And I also knew, as a journalist, retail was hard. It was the last thing I wanted to dip my toe in or get into and I wasn’t a retailer. I had never really worked in retail. I had worked in restaurants as a kid, and but retail wasn’t my thing, and so when I finally did decide to open the store, I went at it a very untraditional way, which I think was my saving grace. I went 100% consignment. I had all these makers, you know, in my back pocket, and we worked together on a consignment model. I had no risk as far as inventory or spending a lot of capital up front. And I think it really helped me figure out who I wanted to be without having to spend a lot because I didn’t have the funds.

Kara Goldin 11:34
So the second store, how long was that from before you actually launched that

Brittany Cobb 11:41
I had the flea markets for about six years before my first store, and then I went quick from store one to store two. I had signed a lease only a few months later, but it took about a year to open it. So from opening to opening to store two, it was about a year later.

Kara Goldin 11:56
When did you know that this was going to be more than just an idea that you wouldn’t have to go back to being a journalist anymore, that this was actually gonna it was a real company and not just an idea.

Brittany Cobb 12:14
I think there’s a few answers to that. One is, once you start to really hire a lot of people, there’s a responsibility piece that you need to commit, and you’re now not just taking care of yourself, but others and their families. And so I felt that was store too for sure. I needed to kind of level up with my, you know, cc suite, if you will. Now we still don’t really have a C suite, but I needed some people that kind of helped me operate it. And so with that became bigger salaries, bigger responsibilities, and I really felt committed at that point. But to answer your question on when I kind of knew it was my thing and and going to go somewhere, was when I kind of unlocked what worked for me from a success standpoint, and where I could generate revenue and have really committed sales. And then that was the half bar experience. So that was a couple years later.

Kara Goldin 13:01
So experiential retail is a phrase we hear often now in community, obviously, with so many people having to work online, and even if you know maybe their company doesn’t have a physical location anymore, what have you seen that has been exciting, surprising around experiential retail, that you feel like you’re you’re really helping people,

Brittany Cobb 13:31
yeah, I mean, the flea market when I had that was experiential retail, and I didn’t realize that was even a term. I don’t think people talked about that really in 2009 but I’ve naturally been doing that since I’ve started the concept. So I guess without knowing it, it was a part of my DNA and what I wanted as a shopper. So it naturally kind of oozed through anything I did. But you’re right. I mean, today, experiential retail is a big key word, you know, we I think we do it the best. As far as a lot of experiential retail is about the retailer. It’s about whatever they’re about at FleaStyle and the original hat bar, it’s about the customer. No two hats are the same. You might come in and make something very, you know, beachy to be, you know, on your fun trip in Northern California, and your friend might come in and be heading, you know, to the Kentucky Derby and want something really preppy. And I love that we can bring all those dreams to life in the same footprint. We’re not a vibe, we’re not a certain thing. We’re not for one person or one generation or one price point. We are for everyone. Everyone needs to wear a hat at some point, whether you’re going to sports outing, you’re in carpool, you’re on the rodeo, and we have all the offerings. So it’s so fun to be able to offer something for everyone. But I think experiential retail is where it’s headed, because people are, you know, they’re a little over kind of the cookie cutter retail experience or something so transactional they want to leave with a memory, with something that feels special, if they’re going to take time away from their busy life. Or, as we all know. Things like Amazon and the convenience of online shopping, they want to do something that’s fun and that’s really worth it, and I think that’s what FleaStyle is all about.

Kara Goldin 15:09
Was there a decision that you made in in building FleaStyle that you thought, I don’t know if this is going to work. Maybe a member of your team brought it up and and, or maybe you had this idea and you said, Let’s just test it. That you’re you’re still surprised that it really, really worked.

Brittany Cobb 15:30
Oh yeah, we’ve had fails. We’ve had, you know, sleeper hits. There’s definitely examples we’ve toyed around with, like, do we do dog hats? And people love their dogs, right? And they want to do something cute for them, crazy idea or epic idea, still to be determined, but yeah, for sure. I think for us today, some of those examples would be really interesting accessories for the hat bar. We make 90% of our goods that I don’t find at flea markets. So domino stick pins, really cool old guitar picks for our Nashville stores, you know, really thoughtful things. And sometimes we try stuff that I think is a little different, or will people really love that I have a little unique taste, maybe a little left to center, and I always love seeing that the response is, heck yes, bring us more. So we’re a little wild in some of the offerings we have, but then again, we have something for everyone. So it’s fun to see those moments.

Kara Goldin 16:23
I love it. I think hats can be intimidating for people. How do you help people get through that? Right? Because I think sometimes people are like, Oh, I’m not I’m not a hat person, or I don’t wear them all the time, or, or even when you and I were talking the fit right? So I think people just feel a little bit, not all people, certainly, otherwise you wouldn’t have a business. But there’s some people that are nervous about wearing wearing hats in some way. Is there some method that you give to people to kind of get over that, because hats are such a, I mean, they just say a lot, right? You can change without changing your clothes. You can actually change that your hat that you’re wearing, and it’s just such a, it’s style, it’s storytelling. It’s everything

Brittany Cobb 17:25
you’re right? I think that, you know, I wrote this book, How to Style a Hat, and I kick it off with, well, Miranda Lambert kicks it off with a beautiful foreword and answers so many of the things you just said. But then it leads into the first question, which is, why we wrote the book, which is, I just don’t look good in the hat. And it’s like, okay, wait a minute, anyone can wear a hat. We just got to find the right hat for you. And so we actually go through that step by step in the book and really help people understand how to find their right fit, how to find a hat they’re comfortable in, how to size it just right. So I’m really excited that the book’s going to kind of just unlock all of those questions for people, and hopefully let us move on to the fun part, which is, Okay, now let’s make the hat and have fun with it. But yeah, I think to your point, a hat can change your attitude in an instant, literally, right now, with my outfit, you know, I’m wearing a faux fur jacket and a cardigan sweater and some cowboy boots, I’m headed to the rodeo in Fort Worth. And so I put on a cowboy hat, and I instantly feel the vibe of where I’m headed. But if I took this hat off and put on, you know, ball cap or a fun foam trucker, I’m ready to pick up my kids from carpool, or hit hit the grocery store, it gets you into a mood. It sets a tone of confidence. Depending on the hat you’re wearing, it can give you coverage. There’s so many different things a hat can do for people, and I really encourage them to try that. I think all of a sudden you’ll find this really fun sense of style, of confidence and then of skin protection. I mean, in today’s day, I think they’re more important than ever, just to keep our skin healthy, and especially as women, as we’re aging and living so much longer, like, Let’s protect our skin.

Kara Goldin 19:03
Yeah, definitely. So FleaStyle has expanded across many states now. How do you maintain the intimacy and authenticity that made people fall in love with FleaStyle in the first place?

Brittany Cobb 19:19
I love this question, and I think it’s the secret sauce for any brand, especially a founder, led brand that is so ingrained in the business. I’m not an influencer, but I am for the company, and I think the most important thing is me staying close to everything we do that’s going to market, and being a huge part of the buying team and everything we purchase, it’s paying attention to the details on every hat and making sure I’m proud of them and stand behind them. I think most importantly, it’s me showing up. It’s showing up in the office daily, staying just as late as everyone else, going to those locations. You know, I fly and visit our stores every four to six weeks, as much as possible. We recently, sadly had a fire and flood. In one of our locations, and I was the first one on the scene, and it was a flight I had to leave California and go to Nashville. But it’s important to me, it shows the team I’m committed and I’m right there with them. I think it allows a buy in where they’re wanting to tell my story to our customer, because they appreciate and respect their founder. My story is the company story. So it’s important that they know my skin condition, my style, how I would want things hanging in the space, or how I’d want something styled. And so the more I’m touching my team through calls and, you know, zooms and physically being there, the more I’m going to stay close to the brand. It’s going to be how I want it to be, and something I’m proud of.

Kara Goldin 20:42
What has been the most difficult piece of growing your business over the last 16 years,

Brittany Cobb 20:50
that’s so hard. I mean, the easy answer is people. People are hard to collect to, you know, create the right team that buys into your vision and does the work they need to to build the brand. The more people you have. We have over 100 employees. I mean, it’s just challenging from an HR standpoint of hiring. How do we can keep the consistency? It’s not that people are bad. It’s just it’s hard. People are imperfect. Me too, and so, you know, leading and managing people, I think is always going to be the hardest part. After that. There’s a whole bag of challenges as you scale. But I think people would be my top answer.

Kara Goldin 21:34
Innovation in any industry, any company, is always this, you know something new, right? You whether it’s from consumers or employees or or yourself, when do you continue to add opportunities in the company? Because it’s like the you know, the what’s, what’s the word, where you know, without getting distracted, you’re constantly, you know, you think it’s a great idea, but maybe it’s going to take more capital. Maybe it’s going to take time, right? It’s going to take, you know, marketing, whatever it is, effort. Who’s going to do it, whatever it is, but how do you stay focused on the parts that have really made you successful, but also not let those just go by the wayside.

Brittany Cobb 22:32
I think prioritizing is the hardest but most important part. As a CEO and founder, I’m an extremely creative person. Luckily, I have a business side to me that I really enjoy. But when you are a creative person, staying focused and on track and remembering the ROI, what’s important to stay successful is challenging, because you have these beautiful ideas, and there’s so much more fun than accounting. And you know, the things that you don’t enjoy. And so I like to run my life, personal and business, by the 8020 rule, where I really focus on, you know, the 20% of things that yield the 80% of revenue. And so when you kind of have that North Star, you can really laser focus on what’s important. With that said, I think you can’t get to tunnel vision, where you forget about the special stuff that might fall in the the 80 that’s still important to touch and do, but on a much smaller scale. So for me, an example would be, you know, focusing on hats and accessories. Those are where our best margins are. That’s where our biggest sales are. But then, like decor in the store, the way it feels and looks is really important to me. We can’t really track that ROI, but maintaining cleanliness and the fun factor of how things look, updating signage or putting in a new neon sign, those are important too. And so I try to balance out my days and my work weeks looking at, okay, what do I need to do? What’s going to move the needle, what keeps everyone getting paid, what lets us grow? And then where can I fit in those fun pieces that I know are important to the brand, my story and honestly, keeping me excited to show up every day as a founder, you can get I mean, I had an accounting meeting that was three hours today. I wanted to run for the hills after like, I can’t put myself where I’m only in those positions as CEO, because I won’t want to show up and keep doing what I love. You’ve got to stay connected to things that keep you happy and keep going.

Kara Goldin 24:22
Definitely, one of the things that I love, love, love about FleaStyle is the virtual hat bar, which I think is everyone can experience it, even if you’re not close to one of your physical locations. Can you describe what a consumer will actually experience when they go into the virtual hap bar.

Brittany Cobb 24:46
Yes, so with nine locations, we hope you can visit us, but it’s unrealistic for everyone. And so we came up years ago with the virtual hat bar experience, where you book an appointment, we give you a call and we figure out via phase. Time or zoom, or whatever the right platform is for the customer, on how we wrap you into our magical experience. So you’ll work with one of our stylists. They’ll help get you the perfect hat. And then you’ll literally pick your things through their eyes and work with them. Walk through the hat bar experience virtually and collect all the fun pieces. They’ll try different hat bands, different pins. They’ll brand your initials, whatever you want, and you get to watch it come to life. So it’s not the exact same, but it’s a really similar experience. And people love it a lot of times they’ll build a hat in the store and then go home, you know, we have a lot of tourist stores and continue to build their hats that way. So the way to make it from wherever you live.

Kara Goldin 25:42
I love it well. Brittany, thank you so much for joining today. Your journey is such a great reminder that great brands aren’t just built on products, but also the experience and being unique and creative. So many lessons learned your courage and actually changing careers and actually doing something that is maybe not done before, and seeing whether or not it would work is just so notable. I mean, just really, really awesome. And for everyone listening, definitely check out the virtual hat bar at FleaStyle and follow along on Instagram. Also, as we mentioned, Brittany’s new book is coming out in April, How to Style a Hat so you could pre order it now, and don’t forget to connect with FleaStyle and Brittany on all social channels, and thank you again, Brittany, really, really excited that you, that you came and and shared some time with us. So Brittany Cobb, founder and CEO of FleaStyle, thank you.

Brittany Cobb 26:55
Thank you for having me. And I hope this helped anyone out there looking to start a business. I remember being in those shoes, and you just have to go for it. Wish them all the best. Awesome. Thank you. Thank you.

Kara Goldin 27:08
Thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And, of course, feel free to subscribe so you don’t miss a single episode of our podcast, just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book. Undaunted, where I share more about my journey, including founding and building. Hint, we are here every Monday, Wednesday and Friday. Thanks for listening, and goodbye for now.

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