Retail Gets Real Podcast

The digital strategy behind Mack Weldon’s growth

Retail Gets Real episode 384: Mack Weldon CEO Brian Berger on retail strategy and advice for aspiring entrepreneurs
June 11, 2025
Men's boxer briefs

The story of Mack Weldon begins with a moment many men know all too well — standing in the underwear aisle, overwhelmed by the choices and underwhelmed by the experience. In this episode of Retail Gets Real, Brian Berger, founder and CEO of Mack Weldon, shares how frustration as a consumer inspired him to reinvent men’s basics with a focus on smart design, technical innovation and a radically improved shopping experience.

How one frustrating shopping trip sparked a retail revolution

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Mack Weldon founder and CEO Brian Berger

For Berger, the tipping point came during an annual underwear restock at Bloomingdale’s. Staring into what he calls “the abyss,” he was asked by a salesperson, “Are you confused yet?” That question became the catalyst for what would become one of the most innovative menswear brands of the last decade. With a background in internet-based consumer businesses, Berger knew he could merge ecommerce innovation with product-first thinking — applying the same level of care and performance design seen in brands like Nike and Patagonia to everyday essentials like underwear, socks, and tees.

While Mack Weldon launched with a focus on underwear and socks, Berger always envisioned the potential to grow beyond. Over time, feedback from loyal customers drove expansion into polos, sweatpants, and elevated wardrobe staples. Still, the strategy remains the same: Deliver on quality, fit and fabric, then expand thoughtfully into adjacent categories. The success of this model underscores an important insight — loyalty comes not just from selling a product, but from solving a problem.

The modern retail customer: algorithm-driven and expectation-heavy

Berger discusses the changing landscape of customer acquisition, explaining how algorithmic traffic from platforms like Meta and Google drives the majority of new business. Interestingly, while the brand targets a core demographic of 25- to 50-year-old professional men, creative campaigns often resonate with audiences well outside that range. To serve this diverse customer base, Berger emphasizes the importance of omnichannel strategy, consistent customer feedback loops and a deep understanding of what drives loyalty over time.

Reflecting on the current AI boom, Berger shares a balanced view of excitement and cautious optimism. He sees real opportunity for artificial intelligence to streamline customer experience — think AI-curated shopping recommendations for a wedding or vacation — but also recognizes the risks of disruption, especially when so much of a brand’s visibility depends on third-party platforms. His takeaway? Stay curious, stay adaptable, and focus on grounded use cases that deliver tangible value.

Tune in to hear how Berger turned a common pain point into a thriving brand — and what his story reveals about the future of retail, innovation and consumer loyalty.

Episode Chapters


(00:00:00) The origin of Mack Weldon

  • How product discomfort turned into a market opportunity

  • Why early DTC brands like Warby Parker inspired the launch

  • What men really care about when it comes to basics like underwear and socks


(00:04:58) The story behind the brand name

  • Is the brand name based on a real person?

  • The trademark challenges of naming a consumer brand

  • Rejected names that didn’t make the cut


(00:07:30) Growing the brand by knowing the customer

  • How customer feedback sparked new categories like polos and sweats

  • Why not every product extension is a guaranteed success

  • How fabric platforms like Silver shape future product strategy

  • How data mining and research shape future strategy and loyalty goals


(00:12:44) Navigating the AI era as a retail founder

  • Why physical products spark more passion than digital content

  • The risks and rewards of relying on big tech platforms

  • How AI could reshape shopping, creativity, and customer experience

  • A practical approach to adopting AI without getting overwhelmed


(00:19:53) Father’s Day picks and the future of retail

  • Brian Berger’s go-to Mack Weldon favorites for the season

  • Why passion alone isn’t enough to start a business

  • How capital constraints are reshaping brand growth

  • Why celebrity-backed brands are gaining momentum


Resources:

Read Full Transcript

Episode transcript, edited for clarity

[00:00:18] Bill: Welcome to Retail Gets Real, where we hear from retail’s most fascinating leaders about the industry that impacts everyone, everywhere, every day. I’m Bill Thorne from the National Retail Federation, and on today’s episode we’re talking to Brian Berger. He’s the CEO and founder of menswear brand Mack Weldon. We’re going to talk to Brian about why he started his retail company, who his customer is today, and his advice for aspiring entrepreneurs. Brian Berger, welcome to Retail Gets Real.

[00:00:51] Brian: Thank you so much, Bill. Really appreciate it, and thanks for the introduction. It’s great to be here.

[00:00:56] Bill: I’m excited for the conversation because as we were talking before we started taping, you’ve done a lot of things, and among them built a very successful company. And as we always say about retail, it’s technology, it’s innovation and it’s risk. And you’ve covered all of those bases. So let’s talk about what inspired you to found Mack Weldon.

[00:01:16] Brian:  I love that question because it’s really how many brands and new ventures come to pass. And it was really the plight of a frustrated consumer.

[00:01:29] Bill: I knew you were going to say that.

[00:01:30] Brian: I hated shopping for underwear and socks. I would go annually to Bloomingdale’s. And in my last trip there, the salesperson said to me, as I stood there looking into this abyss, “Are you confused yet?” And that was really the “a-ha” moment for me.

Just from a customer experience standpoint, the idea that guys who were not buying mass market brands, this is the experience. And as someone who spent their whole career helping to build consumer internet-based businesses, it just seemed to me that there was an opportunity to apply a lot of the advances that were being made in ecommerce and brand building and direct-to-consumer marketing to bring a new brand to life, one that really focused on not only solving for the customer experience piece, but was really product-centric and rooted in innovation and things that many other brands that I admired were doing — Patagonia, Lemon, Nike and others.

[00:02:33] Bill: OK, so two guys talking underwear. You don’t get in a lot of conversations with your buddies about underwear, ever, really. And yet if we did have the conversation, we’d all have our opinions about the type and what’s comfortable, what’s not, what gets you through the day, what doesn’t.

[00:02:52] Bill: So I think that the idea that you go, this is the product that you’re going to focus in on, did anybody say, "Underwear? Really?"

[00:03:03] Brian: Oh, a lot of people said that, including my long-term mentor and board member, Howard Socol, who has spent his entire career as a leader in the consumer retail industry. And there was a lot of crazy to do this. But I think what you said leading up to that is really the crux of it. If you talk to guys, if you even crack the door open with guys about their underwear, their T-shirts, their socks, these foundational items in their wardrobe, they have a lot to say.

[00:03:35] Bill: Right.

[00:03:35] Brian: And it’s not a taboo thing because we’re not talking about risqué and things that are of a sexually charged nature. They’re talking about functionality. They’re talking about fit. They’re talking about how it wears. They’re talking about comfort.

In the early days when we were doing not overly scientific research about things that were important, attributes for the consumer experience and the product experience, there were a lot of things that came up. A lot of common things.

We realized that if we could address some of these product-related issues, and we could highlight that in the way that we marketed to consumers, then we had a shot at bringing new consumers into this brand. The world is very different today than 13 years ago when we started the brand.

Warby Parker and Bonobos were the only two brands of note that were coming at consumers in the way that we did initially. There were others like us, but everyone was small. So it was an opportunity to land-grab a little bit and get customers in. And so that’s what we did.

[00:04:50] Bill: Who’s Mack Weldon?

[00:04:52] Brian: Mack Weldon is actually not a person. It’s a name that was — Weldon was a brand in the early 1900s that made underwear and sleepwear, and it was an abandoned trademark, and we discovered it. We liked it. We felt that it was masculine. It had a sense of timelessness. And then Mac was a modern alter ego to it.

You end up with a lot of these explorations with respect to brand naming because it’s very hard to name a consumer brand without getting yourself into trouble. So lesson one for me was getting real about trademark law, which was the most unsexy thing on the planet, and very frustrating for me as an outsider. But we got to a place that felt right and ran with it. And it’s been a great name for this business.

[00:05:39] Bill: It is a great name. And to your point, it’s very masculine. It’s very non-threatening. It’s like, oh yeah, my neighbor, Mack Weldon.

[00:05:47] Brian: You do different things. We started playing around with naming. You also have identity work happening in parallel. And so the M&W is — look, our logo looks like a crown, but it also looks like flat lock stitching, which is something that we use in a lot of our products. And so there was that aspect to it that we really liked, because we really wanted everything to essentially revert back to product and product first and product innovation. Because we felt that that was a major differentiator.

A lot of the brands that we were trying to steal share from in the early days were licensed brands like Calvin Klein that had huge awareness and mass celebrity marketing campaigns and incredible creative prowess. But the product itself was not so great.

[00:06:38] Bill: Was there a second choice?

[00:06:40] Brian: Well, my choice, which got laughed out of the room, was Top Drawer.

[00:06:47] Bill: I like that.

[00:06:48] Brian: So Top Drawer got laughed at.

[00:06:50] Bill: Guess where my underwear is? It’s in the top drawer.

[00:06:53] Brian: Yeah, now I can laugh at it. The other name that I really liked was Base, base layer.

[00:07:01] Bill: I don’t like that one.

[00:07:03] Brian: That was another popular name.

[00:07:04] Bill: I do like Top Drawer though, for underwear. That’s really brilliant. It’s underwear, then socks, then T-shirts.

[00:07:12] Brian: Yeah. In reflection, the brand is about much more than those handful of products that we started with.

[00:07:17] Bill: Sure, sure, sure, sure. Right. Exactly.

[00:07:20] Brian: Which is license to having [inaudible] brand.

[00:07:22] Bill: So as you said, you now offer an array of menswear. How did this evolution happen? It seems to me that you may have been thinking about this from the beginning, that you would expand into different categories.

[00:07:33] Brian: Well, I hoped that would be the case. I hoped that we would deliver against the value proposition across the products that we launched with, and that would give us license from our consumers to do more and apply that formula to other things. But to be determined. But stay focused on the original mission and suite of products, and do that really well.

And then hopefully one day you get an opportunity to do more than that, expand beyond that. And that call came. We’d regularly hear from consumers — “Love this fabric. Wish you could make it in a T-shirt.” “Love this. I love your T-shirts. Why don’t you make polos?" That sort of thing. And so polos and our Ace, which is our elevated sweats or lounge French Terry program, those were the first product line extensions that we made and have been extraordinarily successful platforms for us.

I think that there have been some cases where it’s been a natural extension of the brand and everything’s been up and to the right. And we’ve had other categories where it’s been a learning experience. Just because I love and I buy my underwear and socks and my T-shirts from you, that doesn’t mean necessarily I want to buy everything in my wardrobe from you.

That was a little bit of a — and you were still in that learning, like what are the things that consumers will consider from us, and how can we frame that into a product strategy and a product roadmap that enables us to deliver the brand and the business objectives that we have?

[00:09:12] Bill: Sure.

[00:09:13] Brian: Typically that reverts back to extensions of existing fabric platforms that have been successful in other categories. So we have silver that we use an array of things. Wardrobe essentials, non-fashion, non-novelty, non-hyper-seasonal items. And things where we can take these products up to another level in a purposeful way. So that’s how we’ve done it.

[00:09:41] Bill: You talked about your customer, your consumer. Who is that? How are you reaching them?

[00:09:47] Brian: Who it is and how we reach them are not necessarily connected, which is a weird thing to say. So historically, brands would a whole bunch of customer mapping and figure out who their archetype is and go out and buy media publications that claim to reach that demographic of people.

Nowadays, everyone, or at least brands like ours, get the lion’s share of their new customers from algorithms that send them traffic. Those algorithms can be stimulated by creative that appeals to 25-year-old guys and 60-year-old guys. You just don’t know. But generally speaking, if you looked at the bell curve for us, it’s 25- to 50-year-old mass affluent professional guys.

That’s typically who we target. But we have meaningful percentages of customers above and below that. But that’s where we program ourselves to. And oddly also for us, we have not had to or never really had to hyper-focus on a niche category and then branch out from there.

We’ve always been reasonably broad in terms of our appeal. And I’m not sure whether that’s a good thing or a bad thing ultimately, but, for us, we’ve leaned into that and make sure our marketing and our voice and our messaging is inclusive of all those demographics.

[00:11:20] Bill: How do you get that feedback from your customers? When you say they like the feel of the particular fabric that we use, and why not make a polo? Is that just people that are reviewing the product, or do you actively go out and seek thoughts?

[00:11:36] Brian:  I think it’s two-fold. It’s inbound from consumers, both from the standpoint of our customer service data and having 13 years of customer service interactions. We do a lot of data mining when we launch something new to get insights from our consumers. And then we’re also doing regular first- and third-party research to get information from our customer base.

And then also, with respect to the third-party research, it’s customers, non-customers, and however we want to segment it. One-hit wonders. People who were customers but have never come back. So we’re always trying to get as much information as we can to help inform what people are liking and maybe what’s causing people to not become repeat buyers from us.

Ultimately, our objective is loyalty. We’re making an investment to get that first customer, and ultimately the profitability and the scale comes from that customer sticking around for a while.

[00:12:38] Bill: So, retail. You ended up in retail. Now, when you were getting your political science degree as an undergraduate, were you thinking about retail at all?

[00:12:50] Brian: It’s not a hard no. When I was in college, I wanted to be a lawyer. And then I just took the year. When I graduated college, my focus was to study for the LSAT and to learn about the internet. Graduated college in ‘96.

[00:13:05] Bill: Yeah, that’s about the time.

[00:13:07] Brian: I had some early exposure to it because my stepbrother was an early internet founder and entrepreneur, and had a pretty hot company at the time. So I had awareness of it, which was probably unusual, but I knew how smart he was, and I knew that this was going to be a thing.

So I wasn’t focused professionally on pursuing a career in retail. But I was always really fascinated by brands that were solving for either a product or a customer experience problem and doing it better. And if you go back and you read my business school application, it says, I am going to spend my professional career so it’s really all about building a set of skills and getting exposure to businesses at a very granular level, and then applying that to an entrepreneurial venture in the consumer space, whatever that means.

So that could have been a service. It could have been an app. It could have been a food thing. It ended up here because ultimately, I became more attracted to physical goods because most of my career was spent really selling virtual goods, I guess, like content, those kinds of things.

And so, I ultimately wasn’t either as excited about those things. The idea of building products and delivering those products to consumers was something that really got me fired up.

[00:14:28] Bill: I said earlier that retail and technology and innovation, they all go hand in hand. We’ve also said for a long period of time that if you for some reason don’t like change, then you really, really should not be in retail. It’s very interesting to me that you said you were learning more about the internet back in ‘96.

Today, it’s those fateful two letters of the alphabet, A and I, that seem to be dominating just about every conversation on every corner of retail and just about everything else. So looking at AI, looking at your business, are you excited? Are you a little bit overwhelmed, or are you a little bit scared?

[00:15:08] Brian: I think excited and scared are probably the two things that come up. I think excited because there’s applications that I think can make the customer experience better, more efficient. Imagine a world where you say, I’m going to a wedding on the beach in Nantucket, and I need a blue suit. This is what I’m looking to spend, and this is how I like to wear my things and da, da, da, and it comes back and brings you a menu of curated items to look at.

So those kinds of things can end up being pretty cool for the consumer, and I think, for brands, it’s just incumbent on brands to continue to execute really well so that you’re always in the consideration set for things. I think on the scared part of it, it’s — again, we get a majority of our sales through two or three very proven channels. Meta, Google, other forms of media, podcasts and things like that.

And so any disruption to those ecosystems, not that I don’t want those ecosystems to be disrupted because I spend a lot of time hating on them, is scary. One thing, if Meta changes their algorithm and you have to learn what the new normal looks like, then I think if there’s a sea change and there’s like a whole new way of doing things, that’s all stuff that we have to stay on top of and make sure we’re adapting and not getting caught flat foot on any of that stuff.

[00:16:44] Bill: Not that anybody cares, but I tell people all the time that AI today seems to me like the internet back in the day. It was just coming out, and what were the implications, and how is it going to work, and what is it going to do to the consumer and blah? Just goes on and on and on.

I will say with AI, though, and maybe it’s just because I’m old and I’m still trying to get my arms around the internet, with AI, to me, it’s like trying to grasp the fact of infinity. The universe is infinity, constantly expanding. To me, AI is like that. It’s just so vast in its implications for humanity for just everything. It’s really hard to get your arms around. I guess what you have to do is control what you can and let the rest just play itself out.

[00:17:36] Brian: Yeah, I was at a talk recently and what you just said was the theme of it. But the speaker had an interesting perspective, and it was that rather than thinking about it as this vast open sea of new frontier, really try and ground your own adoption toward specific use cases.

The most obvious is, I got to write a wedding speech. Let me throw the prompt into ChatGPT and get a baseline. So then not having to sit there and imagine something that’s funny and witty and da da da da da from scratch. The most basic thing. maybe it’s a research prompt to do some competitive analysis.

The more specific you can be about using the tools that are available and experience the power of AI through that, the less overwhelming it is and the more informed you are how to apply it in other areas. So I thought that was a good way to think about it and have taken that advice.

But I think it’s different. If you were getting your master’s right now and you were in college and you really could create a sense of advantage by using these vast array of tools out there, then I think you get up a learning curve faster.

[00:19:02] Bill: Much faster. And it is a little less intimidating. And I guess to that point, it is, use what you can and what you’re comfortable with, take full advantage of it, and this will constantly grow. It’s just like the internet before. People just go to the internet to check the weather, whatever.

And now you can do anything with it, obviously. And I think AI is probably the same, but it’s so vast in its implications. And every time I hear about, well, you can do this with AI, and they’re developing this with AI, I think about your sons. They’re young. They’re the future of it. We grew up with the evolution of the internet. They’re growing up with the evolution of AI, and then what’s next after that.

[00:19:45] Brian: Exactly right. Yeah.

[00:19:47] Bill: Anyway, so Father’s Day. It’s coming up. What are your go-to Mac Weldon items?

[00:19:55] Brian: Absolutely. My favorite are the Pima T-shirt, Pima polo, AIRKNITx underwear, and the Ace sweats. Those are my go-tos. I have lots of other things, but those are my go-tos. And those are great products for this time of year. Cool. Easy. Go with anything. Dress them up. Dress them down.

[00:20:14] Bill: If you were asked by one of your sons or maybe all three, “Dad, I want to be an entrepreneur. Where do I start?” What would you say?

[00:20:24] Brian: I would say, start by working in a business, something that you are good at. If you’re lucky, something that you’re also interested in, passionate about. I think sometimes people get it reversed and they think, let me go into something that I’m passionate about, but it’s not necessarily something that they’re good at.

I think the probability of success is much higher if you have some predisposition toward — some talent toward something. In any case, I would say work in a business, I would say get experience, get exposure, understand fundamentals, understand market dynamics, understand how to deal with people, all of those things.

And within that, if you have an entrepreneurial mindset and a curious mindset, you can spot opportunities. You could spot inefficiencies. You can spot areas where there may be an opportunity for a new business service tool product to come in and solve for that.

The probability of landing on something that has market appeal is much greater when you’re first party observing it versus just sitting in a room and imagining something. I think the movie version is that somebody just stumbles upon this wildly innovative thing and it becomes Facebook or Uber or one of these things.

But those are once-in-a-lifetime things. A majority of entrepreneurship comes as a function of one’s experience with the business or spotting a problem in your daily life. But because you have had experience in a business, you’re way more equipped to bring that to life, even if it’s not related to that business.

[00:22:02] Bill: Or it’s somebody looking at the vast array of underwear and saying, “I can do better.”

[00:22:07] Brian:  In many ways, this was definitely a bet. We didn’t do it in a risk-averse way. There was a lot of investment made without a real sense for whether or not this was going to be something that the market wants.

[00:22:26] Bill:  Well, that’s the cool part. You throw it out there, you do your best, see what happens, and then you build a really successful business. So, we’ve talked a lot about retail in terms of where it is today, where it’s going to tomorrow, but what do you see for the future of retail?

[00:22:44] Brian:  I think the future of retail is interesting right now. A lot of what you see are brands that are getting outsized success and momentum because they’re affiliated with a celebrity or a social media influencer, or somebody who has an embedded audience that they speak to. We are not that. We’re like a more traditional brand that is built off of product and value proposition and customer experience.

I do see advantage being created by that, but just like anything else, it will become fully priced. Celebrities will have their brand, and consumers will start to reconcile with that. But I think right now what you see a lot of is that, is you see a lot of brands getting traction that way.

Omnichannel is critically important. I think you need to show up. You can’t just be a one channel distribution brand. So you’ve got to start from the point of omnichannel, like, what is your strategy for retail, wholesale and D2C fundamentally. And capital. Capital is interesting right now because when we were coming up, it was falling out of the sky.

It’s not that way anymore because a lot of consumer brands didn’t meet the moment or didn’t live up to that valuation that they had. And it’s unfortunate because you have some really amazing brands that are just plagued by the unicorn status that they achieved five years ago.

[00:24:15] Bill: Right.

[00:24:17] Brian: That doesn’t mean the brand sucks. It just means that if you do 300 million in sales, your valuation shouldn’t be two billion.

[00:24:26] Bill: True that. I am not even a business major. I’m a liberal arts major from a land-grant university in the deep south. I even know that.

[00:24:33] Brian: You don’t need that anymore. You have ChatGPT now.

[00:24:36] Bill: Exactly. Brian Berger, it has been such an incredible pleasure talking with you. Thank you so much for joining us on Retail Get Real.

[00:24:45] Brian: Likewise. Great to chat with you, Bill, and I look forward to doing it again soon.

[00:24:48] Bill: I do too. And thank you all for listening to another episode of Retail Gets Real. You can find more information about this episode at retailgetsreal.com. I’m Bill Thorne. This is Retail Gets Real. Until next time, we’ll see you then. 

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