802 Brittany Cobb: Founder & CEO of Flea Style

0:00I am unwilling to give up, but I will start over from scratch as many times as it takes to get where I want to be.

0:09Kara Goldin:You just want to make sure you will get knocked down, but just make sure you don't get knocked out. So your only choice should be, go focus on what you can 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. Thanks to HomeServe for sponsoring this episode. It's 2026 and owning a home is an incredible milestone until something breaks. One minute, everything is running smoothly, and the next you're dealing with a burst pipe, a broken water heater, or an HVAC system that decides to quit at the worst possible time.

1:04Kara Goldin:Repairs don't wait for a convenient moment, and they definitely don't wait for your budget to be ready. You insure your health, your car, even your phone, but what about the systems inside your home? Many homeowners are surprised to learn that regular insurance often doesn't cover everyday wear and tear, like plumbing failures, electrical issues, or heating and cooling breakdowns. That's where HomeServe comes in. HomeServe is like a subscription for your home. For as little as$4.99 a month, you can choose a plan that fits your needs and your budget. And when something covered goes wrong, instead of scrambling to find a contractor, you just call their 24-7 hotline and start the repair process.

1:46Kara Goldin:It's that simple. If you've ever had a surprise home repair, you know how expensive it can get and how stressful it is trying to fix it fast. Honestly, if I had needed this, HomeServe is what I'd use. Having that kind of backup brings real peace of mind. They've been helping homeowners for over 20 years with a trusted national network of 2 ,600 local contractors with 4.5 million customers. a 4.8 out of 5 post-repair rating, and an A plus BBB rating. They're the real deal. Help protect your home system and your wallet with HomeServe against covered repairs. Plans start at just$4.99 a month. Go to homeserve.com to find the plan that's right for you.

2:33Kara Goldin:That's homeserve.com. Not available everywhere. Most plans range between$4.99 to$11.99 a month your first year. Terms apply on covered repairs. Imagine running a business with a dozen different software tools, each expensive, overly complicated, and completely disconnected. It's frustrating, time-consuming, and unnecessary. Now imagine having everything you need in one place. That's Odoo. Odoo brings all your core business tools together in a single easy-to-use platform, so everything works seamlessly, from accounting and CRM to marketing, inventory, HR, and manufacturing. Odoo keeps your entire operation connected and running smoothly.

3:24Kara Goldin:If your business needs it, Odoo's got it, giving you clarity, control, and peace of mind. Odoo sounds pretty amazing, right? So stop wasting your time and money on those expensive, disconnected platforms and let Odoo harmonize your business with simple, efficient software that can handle everything for a fraction of the price. It doesn't get much better than that. So what are you waiting for? Discover how Odoo can take your business to the next level by visiting odoo.com. That's O-D-O-O dot com. Odoo, modern management made simple. Hi, everyone, and welcome back to the Kara Golden Show. So 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 Flea Style.

4:20Kara Goldin:And if you are not familiar with Flea Style, 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, a part of the brand of flea style, 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 Flea Style, 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, locations, including Louisville and Nashville and some of the others on their website.

5:35Kara Goldin: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 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.

6:26Kara Goldin:So nice to meet you. Thank you for having me and so nice to meet you too. Thanks to HomeServe for sponsoring this episode. It's 2026 and owning a home is an incredible milestone until something breaks. One minute everything is running smoothly and the next you're dealing with a burst pipe, a broken water heater, or an HVAC system that decides to quit at the worst possible time. Repairs don't wait for a convenient moment, and they definitely don't wait for your budget to be ready. You insure your health, your car, even your phone, but what about the systems inside your home? Many homeowners are surprised to learn that regular insurance often doesn't cover everyday wear and tear, like plumbing failures, electrical issues, or heating and cooling breakdowns.

7:15Kara Goldin:That's where HomeServe comes in. HomeServe is like a subscription for your home. For as little as$4.99 a month, you can choose a plan that fits your needs and your budget. And when something covered goes wrong, instead of scrambling to find a contractor, you just call their 24-7 hotline and start the repair process. It's that simple. If you've ever had a surprise home repair, you know how expensive it can get and how stressful it is trying to fix it fast. Honestly, if I had needed this, HomeServe is what I'd use. Having that kind of backup brings real peace of mind. They've been helping homeowners for over 20 years with a trusted national network of 2 ,600 local contractors with 4.5 million customers, a 4.8 out of 5 post-repair rating, and an A -plus BBB rating.

8:09Kara Goldin:They're the real deal. Help protect your home system and your wallet with HomeServe against covered repairs. Plans start at just$4.99 a month. Go to homeserve.com to find the plan that's right for you. That's homeserve.com. Not available everywhere. Most plans range between$4.99 to$11.99 a month your first year. Terms apply on covered repairs. Imagine running a business with a dozen different software tools, each expensive, overly complicated, and completely disconnected. It's frustrating, time-consuming, and unnecessary. Now imagine having everything you need in one place. That's Odoo. Odoo brings all your core business tools together in a single easy-to-use platform, so everything works seamlessly.

9:02Kara Goldin:From accounting and CRM to marketing, inventory, HR, and manufacturing, Odoo keeps your entire operation connected and running smoothly. If your business needs it, Odoo's got it, giving you clarity, control, and peace of mind. Odoo sounds pretty amazing, right? So stop wasting your time and money on those expensive disconnected platforms and let Odoo harmonize your business with simple, efficient software that can handle everything for a fraction of the price. It doesn't get much better than that. So what are you waiting for? Discover how Odoo can take your business to the next level by visiting odoo.com.

9:46Kara Goldin:That's O-D-O-O dot com. Odoo. Modern management made simple. Absolutely. So for listeners just discovering Flea Style, how do you describe the brand and what makes it different from anything else out there that one might encounter around hats? 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 Flea Style started back in 2009 when I started as a flea market.

10:28I 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, flea style 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.

11:06And so 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.

11:25Kara Goldin:Imagine running a business with a dozen different software tools, each expensive, overly complicated, and completely disconnected. It's frustrating, time-consuming, and unnecessary. Now imagine having everything you need in one place. That's Odoo. Odoo brings all your core business tools together in a single, easy-to-use platform, so everything works seamlessly, from accounting and CRM to marketing, inventory, HR, and manufacturing. Odoo keeps your entire operation connected and running smoothly. If your business needs it, Odoo's got it, giving you clarity, control, and peace of mind. Odoo sounds pretty amazing, right?

12:13Kara Goldin:So stop wasting your time and money on those expensive disconnected platforms and let Odoo harmonize your business with simple, efficient software that can handle everything for a fraction of the price. It doesn't get much better than that. So what are you waiting for? Discover how Odoo can take your business to the next level by visiting odoo.com. That's O-D-O-O.com. Odoo, modern management made simple. Thanks to HomeServe for sponsoring this episode. It's 2026 and owning a home is an incredible milestone until something breaks. One minute, everything is running smoothly, and the next you're dealing with a burst pipe, a broken water heater, or an HVAC system that decides to quit at the worst possible time.

13:06Kara Goldin:Repairs don't wait for a convenient moment, and they definitely don't wait for your budget to be ready. You insure your health, your car, even your phone, but what about the systems inside your home? Many homeowners are surprised to learn that regular insurance often doesn't cover everyday wear and tear, like plumbing failures, electrical issues, or heating and cooling breakdowns. That's where HomeServe comes in. HomeServe is like a subscription for your home. For as little as$4.99 a month, you can choose a plan that fits your needs and your budget. And when something covered goes wrong, instead of scrambling to find a contractor, you just call their 24-7 hotline and start the repair process.

13:48Kara Goldin:It's that simple. If you've ever had a surprise home repair, you know how expensive it can get and how stressful it is trying to fix it fast. Honestly, if I had needed this, HomeServe is what I'd use. Having that kind of backup brings real peace of mind. They've been helping homeowners for over 20 years with a trusted national network of 2 ,600 local contractors with 4.5 million customers. a 4.8 out of 5 post-repair rating, and an A plus BBB rating. They're the real deal. Help protect your home system and your wallet with HomeServe against covered repairs. Plans start at just$4.99 a month. Go to homeserve.com to find the plan that's right for you.

14:35Kara Goldin:That's homeserve.com. Not available everywhere. Most plans range between$4.99 to$11.99 a month your first year. Terms apply on covered repairs. 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 it's probably different than how it all started 16 years ago, but what is the promise to consumers today? So when you walk into a flea style 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.

15:24The 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 thousands 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.

15:57Kara Goldin: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. 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, play water polo, softball. So I always had to cover my skin.

16:38And 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.

17:11And it's really grown organically, but it totally stems from my need to wear one every day.

17:16Kara Goldin: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, I mean, back in 2009, I was a journalist. So I was covering and I was covering all lifestyle sectors. So, you know, I'd meet a cool shoemaker, jewelry maker, 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.

17:58And 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, tens of thousands over the years.

18:31And it's a huge part of our DNA still today. We carry tons of them in our stores. We still consign with them. We host pop-ups at our stores. It's important to me to always stay connected to the makers and shakers.

18:42Kara Goldin:So you went from being a lifestyle journalist to actually starting 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? 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 going to throw the spaghetti, see what stuck. I'm really glad that it did.

19:30But, 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 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.

20:00Kara Goldin:So you launched your first location in Dallas? Yes. So first location was right in my backyard. And what was the point where you said this can be more than that one location? I think, you know, the first show was an instant success. We had a line around the 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. Crazy story. I actually lost my job the week before with my journalism job. So it also gave me the kind of hootspot of figure it out because I didn't have something else, you know, full time.

20:40But as far as the retail piece goes, I really, I always listen to my customers, is, 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.

21:11I had worked in restaurants as a kid, 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 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.

21:40Kara Goldin:So the second store, how long was that from before you actually launched that? 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. 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 going to, it was a real company and not just an idea? 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.

22:27And you're now not just taking care of yourself, but others and their families. And so I felt that was store two, for sure. I needed to kind of level up with my, you know, C-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 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.

23:02And then that was the half-hour experience. So that was a couple years later.

23:07Kara Goldin: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 really helping people? 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 started the concept. So I guess without knowing it, it was a part of my DNA and what I wanted as a shopper.

23:54So it naturally kind of oozed through anything I did. But you're right. I mean, today, experiential retail is a big keyword. You know, 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 flea style 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.

24:31We'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 fit.

25:13And I think that's what Flea Style is all about.

25:16Kara Goldin:Was there a decision that you made in building Flea Style that you thought, I don't know if this is going to work. Maybe a member of your team brought it up and, or maybe you had this idea and you said, let's just test it, that you're still surprised that it really, really worked. 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? 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.