Bree McKeen: Founder & CEO of Evelyn & Bobbie

Episode 889

Tolerate discomfort? Not today. ✨
On The Kara Goldin Show, I sit down with Bree McKeen, Founder and CEO of Evelyn & Bobbie — the intimates brand reimagining what women should expect from their bras.
Bree’s own experience as a 34G woman dealing with tension headaches, shoulder pain, and posture issues led her to question one of the most worn — and least questioned — items in a woman’s wardrobe.
We talk about how she left a finance career to reinvent the bra from the inside out, developed Evelyn & Bobbie’s patented EB Core® wire-free support technology, and built a brand focused on comfort, confidence, inclusivity, and real product innovation.
If you’re interested in founders solving real customer pain points and challenging industries that accepted “good enough” for too long, check out the interview on my podcast. You can find it here or anywhere you listen to podcasts 🎧

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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. We 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. What happens when one of the most worn items in a woman’s wardrobe has not been meaningfully rethought in nearly a century, and someone finally decides to question the entire thing? Today’s guest is Bree McKeen, who is the founder and CEO of Evelyn & Bobbie, an intimates brand redefining what women should expect from their bras and undergarments? And Bree is a former Silicon Valley executive who spent years dealing with headaches, shoulder pain, posture issues, and eventually realized that the problem was something millions of women deal with every day-a bra and undergarments that maybe needed to be engineered a little bit better. So she left a promising finance career and set out to reinvent the bra from the inside out. I cannot wait to talk to her about the incredible patented EB Core technology wire-free system that Evelyn & Bobbie has patented, designed to be the best bra, and I always say not just bra, but also other undergarments too that are really, really redefining what it means to be a product in this category. So, Bree, so nice to meet you, and welcome to the Kara Goldin Show. I’m so excited to meet you, and such a fan of everything that you’re doing, and Evelyn & Bobbie, so welcome.

Bree McKeen 2:22
Well, ditto, Kara. I’m so happy to be here.

Kara Goldin 2:25
Very, very excited. So, for so Brie, for listeners who are just hearing about Evelyn & Bobbie, or maybe they have seen Evelyn and Bobby, heard about Evelyn & Bobbie, but they don’t really understand what the brand stands for today, and what makes it different from other intimates companies. I’d love to hear from you what that

Bree McKeen 2:49
is. Yeah, when I came to this industry as an industry outsider, I was not a bra designer when I started this company. I saw an industry Deeply lodged in outdated convention that did not serve us, so we threw out all the old ways of making bras, started from scratch, and ultimately created after 88 years of the underwire. It was patented in 1931. Our patented EB Core is the first true structural replacement for the underwire in almost a century.

Kara Goldin 3:26
Wow, that’s that’s amazing! And you had a personal experience, which every great entrepreneur that I’ve met has can tell their story. Can you talk a little bit about what was going on with you personally and why you decided I need to go do this?

Bree McKeen 3:43
Yeah, Kara, I’m a 34G. That is actually incredibly average in the United States. I had a routine of taking my bra off in the car before I put my seatbelt on. Every day for me was underwire discomfort. The weight of my bust would create pressure points on my ribs. I had permanent divots in my shoulders. I would get tension headaches almost every day at 3p.m. And I ended up going on what I thought was going to be a posture journey, thinking that my discomfort was something wrong with me, and discovered that ultimately there was a massive set of problems in the bra industry that needed to change. You mentioned

Kara Goldin 4:30
that you didn’t have experience in the bra industry other than the fact that you were a consumer. What was the moment when you just said maybe I can go do this. That you were qualified. That you that you knew how to actually start.

Bree McKeen 4:48
I studied design thinking at Stanford. Spent some time in that space and in the D School, the design school at Stanford, and. Human-centric design, what they call design thinking, is a way of innovating. And as I did diligence on this opportunity, because I I was sitting on the other side of the table doing due diligence for a boutique VC firm, when I started doing diligence on this idea, it was really clear to me that the woman’s experience, the person who wears the product, was completely missing from the equation. It was not being considered. It wasn’t being tested, and so I saw my outside perspective as an advantage, and I had seen that work in Silicon Valley. I recognized that there was this belief that this is the way bras have been designed, so that’s the way to design bras, and it was completely wrong.

Kara Goldin 5:54
And what was your first, if you can remember, going back to I guess 2014 when you were thinking, okay, now it’s time to go do this. Did you write a business plan? Did you pick up the phone and start talking to people who might be able to give you insight? Did you talk to professors at Stanford? I mean, what was kind of the first step that you made?

Bree McKeen 6:17
I started by talking to other women, and that’s a practice that we still have today. What I think lit the biggest fire in my belly that this became more about solving a bra problem for myself, and ultimately, I think about culture change around women’s product design was that I would talk to women and say, “Hey, do you love your underwire bra, and do you know what size you are? And do you have a drawer full of bras that you just can’t wait to put on? And we all, every woman listening, knows the answers. No, she had 20 bras in her drawer. She wore one of one or two of them, the ugly, comfy ones that she felt like she probably shouldn’t be wearing. And most critically, Kara, when I talked to women about their bra life, immediately within a few sentences, the conversation went to what was wrong with their body, and I realized that the bra industry had become a marketing industry more than a product design industry, and we had all-all of us as women-internalized this idea that if the product didn’t fit or the product didn’t work, it was probably because there was something wrong with our bodies. My shoulders are too broad. My shoulders are too narrow. I have this big rib cage. I have this tiny rib cage. My boobs are so big. My boobs are so small. It was like, no, our bodies are fine. Let’s be empirical about how human bodies present, and then let’s change the product to actually work with the realities of our bodies.

Kara Goldin 7:48
So, EB Core, your patented technology. Can you talk a little bit about that?

Bree McKeen 7:54
Yeah. So, we take 120 band and cup sizes, which was developed in 1933. By the way, if you don’t know what your bra size is, not your fault. It is the most confusing sizing system, and ultimately doesn’t work very well. We take 120 conventional sizes and bring it down to seven easy sizes from extra small to three XL by using advanced performance athletic apparel manufacturing methods. So I share my supply chain with Nike, Adidas, Under Armor, all the big performance athletic apparel brands, and what we did with the EB Core was take a three dimensional approach. So really powerful high recovery fabrics that we developed took 18 months just to develop these proprietary fabrics, and then we put a network of supports inside the garment. So you can think of it as like a three-dimensional scaffolding or an exoskeleton, and then specifically replacing the underwire with more of a shelf, so it’s a three-dimensional sling, if you will, that shifts the load of your bust off of your delicate neck and shoulder muscles and onto your core. So, if you think about old school bras, old school underwire bras, as kind of, I think of it like a bag that you hang over your shoulder. We’re creating a shelf that sits on your core to lift from below. Now, this all sounds very engineered because it is, but when you wear it, it just feels like a second skin. And what we hear from customers all the time is that they forget they were wearing it.

Kara Goldin 9:38
Yeah, it’s it is so comfortable. I love your products, and I have to say that I was skeptical because you know, only having a choice of seven products, you’re thinking, how could this possibly work for me? And it does. And I just think that it’s so so interesting what you’ve done, and especially because. Because, as you mentioned, you hadn’t been in this industry, but prior to this, you were working in venture capital.

Bree McKeen 10:09
Yeah, in early stage investing. So, but on the investor side of the table, and so that was really helpful in venture formation, I think, for me. But I, of course, still made plenty of mistakes as we all do, but yes, I think it was really a love for innovation that drove me to this. I mean, at the end of the day, I am a product person, and it took 1000s of prototypes to get to this design. It’s interesting because when women try our products for the first time, it feels really new. Once you get it and you experience it, it is easier than it makes your bra life easier than it’s ever been before. But you know, these products are really snug when you get them, and then over three wears, it basically molds to your body for a custom fit. It’s it’s unlike anything else on the market.

Kara Goldin 11:04
So you develop the product and launch it, and how did you figure out your go to market strategy at this point?

Bree McKeen 11:13
Oh, Kara, we our first product that we launched tanked, like just failed miserably. Like I had a I had a talented CTO from MIT. We had algorithmic sizing, and it was like so much newness, and ultimately way too complex. And so mine is a fail forward story for sure. So we had to do massive layoffs, downsize the company, and relaunch a completely different version using the same intellectual property, but that failure taught me everything I needed to know about the simplicity that women ultimately were seeking, and that became the destination. But really, I would say our marketing-we’re still getting our marketing up and running because we had to pivot and relaunch the company. Those were those were hard days, Kara. I lost a lot of hair

Kara Goldin 12:12
dealing with that. And and would you say it was when you look back on those? What do you think was your biggest mistake? Was it product was it go to market strategy was it what do you think was the key thing

Bree McKeen 12:27
it was product yeah I mean we we did we launched a wildly innovative bra that now knowing what I know now I would have never attempted in less than 48 months we did it in 12 And the product didn’t match the design thesis and the intent, and I knew that, and I didn’t listen to my gut. And we launched it, and but you know, it’s I’m grateful for all of it because it really taught me what I was missing from that human centric design, and that was simplicity. At the end of the day, good design is simple.

Kara Goldin 13:08
Yeah, no, definitely, and I think we’ve had so many founders on here who have talked a lot about that, like make it so simple, and also make it easy for the consumer to be able to purchase something and not make it so complicated that they’re nervous to do it in every single category. So, so then you regrouped and decided to come out with a different line of products. And how long did it take you to say we need to stop right and we need to regroup. And would you say that it wasn’t soon enough? I think oftentimes that’s something that founders, you know, they’re defending their baby, right? When when the numbers don’t lie, and we’ve heard numerous stories where, like in in the case of the company I founded, Hint, there were you know flavors where we were like, no, give it some more time, it’ll be fine. But you know, it was very clear that it was not going to make it. Did you have any kind of sense now that you probably should have pulled it earlier or anything else like that? I

Bree McKeen 14:19
mean, my gut was screaming at me not to launch it, but I was under pressure from timelines, and and I had made some big promises to my investor. Right, so I pivoted pretty damn quickly. Kara, I had started working on the Defy Bra. That was the first of the the next generation of products, we had already started working on that, and so it launched. I think within seven months of the initial pivot, but it was we had to launch with such with a lot less in terms of resources. So we definitely put some some good money after bad on that first version of the of the company, but the first product, the Defibra, started selling out immediately, and you know we’ve been doing this now since 2018 is when the Defibra launched. We just launched our ninth product, so wow! Yeah, we just launched our ninth style, where you know other companies, and frankly, I’ve seen bra companies come and go that make a few good products, get some recognition, and then they merchandise like hell. That is not my strategy. We have 270 real fit models. We believe in fewer, better things. We obsess over fit. I think in a way that no other company in the world does. I mean, we have hundreds or 1000s of hours of wear testing per style, and frankly, I will personally not sign off on anything because of my lessons with the first pre-pivot version of the company. I will not launch anything that I can’t wear for a 12-hour day and do all the things that I want to do in the day in that product. I don’t believe that women should have to wear more than one bra in a day. Go do all the things, and that’s what our bras do.

Kara Goldin 16:23
So, what is the biggest myth consumers believe about what makes a bra supportive?

Bree McKeen 16:30
That you can’t get lift without an underwire. I would say is the number one myth. That used to be true. I get it. That used to be true for me until the EB core. And then the second myth is that if your bra doesn’t fit, it’s probably because there’s something wrong with your body. Nope, that is not it. Your body is perfect; it is the bra that needs to change, and that is not the message that women have been getting. And I know why most bra companies are designing on a 34B. If they’re really progressive, they’ll design for a 34B and a 34D. Okay, that does not help your GHIJ cups at all because it’s an engineering problem. A 34B might have a pound of breast tissue, and you know when we go up to a two XL and a three XL, where we are dealing with 20 pounds plus of breast tissue, you have to engineer each size differently, and we do. That’s awesome. So Evelyn & Bobbie, where did the name come from? I wanted the brand to be grounded in real women, so Evelyn & Bobbie were my two matriarchs. Two of my matriarchs, Evelyn was my maternal grandmother. She was a starlet in the ’30s. She represents beauty for our brand. And then my aunt Bobby was a remarkable woman. She symbolizes purpose. We believe in beauty and purpose being forever linked. Aunt Bobby was an entrepreneur. She traveled the world. She was a seamstress. She taught now. There’s hardly a stitch, Kara, in any of my garments. They’re super high tech, but she taught me how to sew. And I remember being 10 years old and having to go through with her and trim each bobbin thread so carefully, she really instilled that the details are what make a garment truly premium. So you have one of

Kara Goldin 18:30
the 16 patents that you have. Is that right?

Bree McKeen 18:34
I think we have 18 internationally now. Six of those are fully issued U.S. utility patents, and those are the most important patents. Those are the ones that ensure we are the only bra brand in the world with that powerful shelf, that EB core. So interesting. I read something or heard you talking about what your experience in getting those patents taught you about about women venting products for women. You know, can you share a little bit more about that? Yeah, patents are proof. Patents are proof that you have a novel concept. Utility patents are hard to get, and look, we’re still living in a world. I think I don’t. I haven’t seen the stat for 2025, but every year, female-founded companies get around 2% of venture capital, and it’s something that I’m really passionate about because I feel like this is not just happening in bras; it’s happening across women’s products everywhere, where human-centric design is not happening for women. We are not. I mean, look at healthcare. Yeah, there are so many things that just completely ignore the woman’s experience, and we need to start having human-centered design for women’s products. But you got to get your product funded, and there’s a pretty chance that the bulk of your investor pool is not using that female product, and that. People naturally invest. There’s no fault in it. People naturally invest in things that they can understand. So if you’re bringing a women-centric product to market and reliant on male investors, IP is something they can understand. Patents they can understand. They can hand that to their lawyer and say, “Do due diligence on this patent.

Kara Goldin 20:25
Yeah, it’s it’s so true. I always said when we were going through the process of raising money and talking to Silicon Valley investors, we didn’t have any technology behind the water, but my story of being a huge diet soda drinker and wanting to get off of sweeteners. My favorite line that that came out of the the pitch sessions that we were a part of was, “I’ll have to ask my wife or my girlfriend about this, and I can only imagine some of your conversations. Right? Oh my

Bree McKeen 21:00
gosh! I mean, oh, I you’re the first woman who has reflected that back to me, and that moment, I I finally started saying, oh, I didn’t realize that your wife was so pivotal for your due diligence process. It seems like I should be talking to her.

Kara Goldin 21:16
Yeah, it’s it’s so funny, and a lot of times they would not even know that they said it right, like it’s just they would just say it off off the cuff, but it’s it’s just too much. One of the trademarks that you have is the true complexion color range. I’d love to hear you describe that and talk a bit more about that too.

Bree McKeen 21:35
Yeah, in my human centric design, I learned that a nude bra is the first bra that women want to buy. That’s the first color because it disappears beautifully under your white t-shirt, and anything that disappears beautifully under your white t-shirt disappears under everything. So, nude is not one color. So we have lots of colors of nude, so that everybody can have that white t-shirt experience of a bra that completely disappears, and I will tell you also, Kara, this bra is so flawless because of the technology. Just the smoothing, the 360 degree smoothing. I’m obsessed.

Kara Goldin 22:16
Yeah, no, it’s it’s so so terrific. What customer feedback has led to your biggest product improvements.

Bree McKeen 22:24
One of the things that we do differently is we will be iterative. That’s a a real tenet of design thinking. So we have taken a couple of our best sellers and improved a couple of the sizes based on consumer feedback and larger data sets, so that is not we. We will have subtle rolling changes because we’re designing down to the to the millimeter, which is pretty controversial in in any apparel industry to have rolling changes for core change for core products, but every innovation at Avalon and Bobby has come from listening to women. So we just launched, and we actually just won the won an Oprah Bra Award for our new Busty Bra, and the Busty Bra is for if you’re if you’re listening to this and you’re busty, you already know it’s for women that have a tiny rib cage but a really full volumous bust, and that customer has been ignored by the industry forever. They’re hard to fit. You got to an abandoned cup size. You got to have so many SKUs to look after that body type, and we knew with our powerful four-way stretch and our proprietary glues that we could we could solve that problem. So we just launched with three sizes: small plus, medium plus, and large plus. And the reviews are pouring in from customers. It’s only been in their hands for a few days. But when I say that these products can be life changing for someone, they are. But that’s the busty bra. Our most recent launch came from listening to women, and then we were supposed to launch months earlier. Even though we had met all of our metrics for launch, I could see that there was something happening in the backbend after two or three weeks of wear, that wasn’t giving that perfect smoothing hug that I wanted, and I said, “We’re not launching it. We’re going to go back and get it right because mediocre is not good enough. And that’s something we take a lot of pride in. And I think it’s of it’s something that companies don’t do right. They they hit a launch deadline for better or worse, and we prioritize the customer loving her bra.

Kara Goldin 24:46
I love that you’ve expanded into retail with Bloomingdale’s and Nordstroms, and internationally, you and I were just chatting about John Lewis and in the UK. So exciting! So, how do you think about? Retail expansion for a product that customers they need to experience it, right? I mean, that’s the that’s the key. They want to try it on. Obviously, it’s maybe easier to in a in an experience with direct to consumer because they understand that they can return them and make sure that you can see them. But what is the experience that what has wholesale taught you that maybe direct to consumer could not? I would say our

Bree McKeen 25:30
prioritization of in person bra shopping is something that we’ve always had. So I’m also in 350 local bra boutiques. I love supporting American small business, and the expansion in department stores has a really similar effect. I think the best way to buy a bra is to go try it on, and ideally to have a fit expert who can who can help you. Now, buying it direct to consumer is also amazing, but partners like Nordstrom, man, they’ve been incredible partners. Where we have grown so quickly with them, there is so much demand for these products. We’re now being rolled out to all doors. We also have a fast growing partnership with Shields, which I just love Shields as a proof point because this is. Do you know? Do you know Shields, Kara? No, I’m not familiar with them. They’re like mega outdoor sportsmen department stores, I guess. But they’re all like you can buy a new rifle, a Yeti cooler, and an Evelyn and Bobby bra. I mean, they and and I just love it because those are these are active women on the go who want premium products, and you know, so the wholesale expansion to me is really, really critical because I love meeting a woman where she’s at. You know, if she’s walking in to Nordstrom, which is, I think, still one of the premier kind of bra expert destinations, we’re part of their prosthesis program. Our bras are amazing after any kind of breast surgery. They’re a surgeon recommended, and so the education piece can can happen person to person in a really intimate way in the Nordstrom fitting room. And so I love wholesale. I just I think it’s the best experience for bra shopping.

Kara Goldin 27:23
So, when you think about your role in building Evelyn & Bobbie with, you know, amazing products as you’ve done, what do you hope that people will take away from it? That you are doing that they hear that you’re sitting in that seat, not just as a founder, but also the CEO, somebody who’s thinking about them, who wants to solve problems. What do you want to be known for?

Bree McKeen 27:51
I want women everywhere to understand that your body was never the problem. Your body was never the problem, and we have every right to demand more from our products. We are voting with our dollars, so vote for those female-founded companies that are prioritizing your experience in product design because it matters, right? Like my daughters will grow up with the belief that bras should be comfortable. Kara, did you grow up with the belief that bras should be comfortable?

Kara Goldin 28:37
No, no, not at all.

Bree McKeen 28:40
How basic, right?

Kara Goldin 28:42
Yeah.

Bree McKeen 28:42
So that’s it.

Kara Goldin 28:44
Yeah, definitely. Well, Bree, thank you so much for joining me today. I love your story, and Evelyn & Bobbie, you guys are killing it. I I love everything about it-the technology, the products. You know, it’s so nice to hear from the people behind the brands. I just, I think you are doing really, really great things. And for everyone listening, be sure to check out Evelyn & Bobbie, and follow what Brie and her team are building over there. They have some new products that have just come out. Definitely, as Bree was saying, that everybody should definitely check that out. We’ll have all the info in the show notes. And thank you again, Bree. Thanks everyone for listening. Until next time at the Kara Goldin Show.

Bree McKeen 29:32
Thank you, Kara.

Kara Goldin 29:33
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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