Chord

Episode 25 · Jun 3, 2026

Why Brian Berger Wishes He’d Gone Wholesale from Day One

Brian Berger · Founder and CEO, Mack Weldon

Brian Berger has spent nearly 15 years building Mack Weldon into a men’s basics brand with a direct, loyal customer relationship, and he did it by staying disciplined when everyone else was spending their way to growth. In this episode, he shares what he’d do differently, and the answer will surprise operators who went all-in on DTC.

Behind the Expert

Brian Berger founded Mack Weldon in 2012 after a career in early internet and consumer-tech media businesses built around advertising and sponsorship — not fashion. He'd always wanted to apply that internet and data fluency to a physical consumer product, and found his opening in the most overlooked category in menswear: socks, underwear, undershirts, and t-shirts, then dominated by licensed and mass brands like Hanes, Jockey, and Fruit of the Loom. The idea crystallized after a bad in-store experience buying underwear at Bloomingdale's. Thirteen years later, Mack Weldon has expanded from basics into sweaters, denim, wholesale, and physical retail, and Berger has become known for prioritizing profitability and capital discipline over the growth-at-all-costs playbook many of his 2012-era DTC peers followed.

The Quick Hits

  • The single biggest regret: not going multichannel — at minimum wholesale — from day one. It's cheap to start, diversifies revenue away from paid acquisition, and unlike ad auctions, isn't a zero-sum game against competitors.
  • Profitability is a discipline, not an afterthought: tie every dollar of capital raised directly to business need, and ask whether it moves you toward or away from being self-sustaining — not just toward growth.
  • Loyalty is downstream of product, not engineered by CRM. Points programs and perfect email cohorts are table stakes now; what actually creates loyalty is a product good enough that customers become net promoters.
  • Leaner teams plus selective AI: point it at specific, bounded business problems (like a CFO building an inventory-transfer app in a weekend) — not at replacing the real people and real storytelling behind the brand.
  • Relevancy in agentic/AI search runs on the same fundamentals as SEO always did — legitimate third-party content and a site that's easy to understand — not shadow pages or tactics built to game a model that will change tomorrow.

A category no one had bothered to brand

Berger didn't come from fashion — he came from early internet and consumer-tech media, businesses built on advertising and sponsorship models. What he brought to Mack Weldon was a personal frustration: buying underwear once a year at Bloomingdale's, getting asked by a sales associate "are you confused yet?", and realizing there was no real brand in the category besides a licensed Calvin Klein. Socks, underwear, undershirts, t-shirts — the foundational, overlooked items in a guy's wardrobe — were being sold by Hanes, Jockey, and Fruit of the Loom with no real product story. Mack Weldon's founding bet was to apply what Berger calls "a Lululemon-level product formula" to that boring category: a cashmere sweater blended with Lycra and lined in CoolMax cotton is the same instinct that first went into a t-shirt.

The wholesale regret

Mack Weldon launched digitally native in the summer of 2012, in the Bonobos-and-Warby-Parker wave that proved you could build a brand without a store footprint or a huge balance sheet. Looking back, Berger's clearest regret isn't a product or marketing call — it's channel sequencing. He believed the core of the business was owning the customer relationship directly, and since the product categories were semi-consumable, that relationship would compound without needing retail. What he'd do differently: go multichannel, at minimum wholesale, much earlier.

The logic is about durability, not just diversification. Wholesale carries a lower margin but skips customer acquisition cost entirely — the real cost is people: sales reps, commissions, a trade-show booth. Once that's covered, it's profitable revenue that isn't Meta or Google. And unlike paid acquisition, it isn't zero-sum: Berger's read is that most DTC-era operators mistakenly treated customer acquisition like a winner-take-all technology market, when a clothing brand launching didn't actually take share from Mack Weldon in the same way a competing rideshare app takes share from Uber.

Profitability as a discipline, not an afterthought

Mack Weldon got to profitability before it was fashionable, in an era — 2012 onward — when investment dollars were chasing exactly this kind of business model and the incentive was to raise, spend, and hire ahead of revenue. Berger's discipline was procedural: correlate the capital you take to the actual needs of the business, and interrogate every dollar against a single question.

That discipline extends to team size. Berger expects the next generation of durable brands to run leaner than founders assumed possible — not because ambition shrank, but because the infrastructure did. Mack Weldon no longer needs in-house engineers to run its commerce stack; Shopify and an agency cover what used to require a product-development team.

Loyalty is earned, not engineered

Berger has walked back his own earlier belief that the perfect CRM segmentation and email subject line would move the retention needle. Those are table stakes now, not differentiators. What he thinks actually works is authenticity and product quality — a local partnership like the one Mack Weldon did with Juice Press in New York, or a points-based loyalty tier that layers economic incentive on top of a product people already want.

His test for a loyalty program is blunt: think about the loyalty programs that actually excite you — they're usually the ones with an economic hook, like a punch card. But you wouldn't be loyal to that brand if the underlying product were bad. The program is the icing; the product is the cake.

Leaner teams, selective AI

Berger's clearest AI success story is narrow and operational, not creative: during a recent warehouse move, Mack Weldon's CFO/COO built a custom app over a weekend to manage dynamic inventory transfers — turning a process he'd have had to personally micromanage into one a team member could run with him providing oversight. That's the pattern Berger trusts: AI solving a specific, bounded business problem. He's far more cautious about AI in creative and brand storytelling, where consumer apparel and CPG haven't fully solved for physical models, and where the line between "proprietary creative" and "generic, sanitized AI output" isn't settled yet.

Relevancy in the agentic era

On agentic commerce, Berger is deliberately unhurried — engaged, not chasing. Mack Weldon's own team is starting to split its search behavior between Google and tools like Claude or ChatGPT, and the brand is already showing up when someone asks an AI for the best men's boxer briefs. Berger's explanation is that it isn't magic: it's the same affiliate and third-party content work the team has done for twelve years, because the models are drawing on what's already out there, not generating brand reputation from nothing.

He's explicitly wary of treating AI relevancy as a new algorithm to reverse-engineer — the same trap that turned SEO into a game of chasing a ranking signal that changes underneath you. His approach stays close to fundamentals: legitimate third-party content and a site built to be understood, by people and by agents alike, rather than shadow pages engineered to game a model.

Sound Bites

  • Comfort is the punch line for everything that we do.
  • If I could rewind the clock, and if I look at some of our peers that have really broken out, I would have done multi-channel — at minimum wholesale, which doesn't cost a lot from a capital perspective — much earlier.
  • The need for capital really should be directly correlated to the needs of the business. And with every dollar you take, the mindset should really be: is this taking me further away from being a profitable business, or is this just helping me advance my goals in line with whatever my profitability goals are?
  • You don't really have control over your customer. The one thing you have control over is making sure everything they buy from you, they love — and that when you show up in the world, you do it in an authentic, incredible way.
  • We can't have all this kind of sanitized AI creative out there in the world. But there will be a place for it, and it will reduce the need that you have on your physical team.

The Chord take

Strip away the sock drawer and this is a story about sequencing and discipline. Mack Weldon's founding-era peers largely bet everything on owning the direct customer relationship and treating acquisition like a land grab — Berger's regret is that he played that same game for longer than he should have, when a cheaper, non-zero-sum channel was sitting right there in wholesale. The thread runs through everything else he talks about: profitability tied to actual need instead of available capital, loyalty earned through product instead of engineered through CRM, AI pointed at one bounded operational problem instead of the whole brand voice. Even his read on agentic commerce refuses the shortcut — the brands showing up when someone asks an AI for a recommendation are the ones that did the unglamorous, structural work for years, not the ones chasing this month's ranking trick. For operators, the lesson isn't "add wholesale" or "add AI." It's that durability comes from diversified, disciplined foundations built early — the channels, the capital structure, the content — and there's no later shortcut that substitutes for not having built them.

Put it to work

  1. 1Pressure-test whether a cheap, non-zero-sum channel — wholesale, retail, trade shows — could diversify revenue and reduce your dependency on paid acquisition, the way Berger wishes he'd done years earlier.
  2. 2Correlate every dollar of capital raised to a specific business need, and ask whether it's moving you toward or away from profitability — not just toward growth.
  3. 3Split your growth-marketing and brand-marketing job descriptions honestly. They require different skills; don't expect one early hire to be both a data analyst and a brand storyteller.
  4. 4Invest in legitimate third-party content and clear site fundamentals as your defense against algorithmic and AI-search volatility, instead of manipulative tactics that get patched out the moment a model updates.
Full transcriptShow ↓

Bryan Mahoney

Welcome back to another episode of the Brilliant Commerce Podcast, where I get a chance to sit down with some of the brightest minds in commerce, working behind iconic — and, as I like to say, next-to-be-iconic — brands. I think Mack Weldon is probably right in between the two. I've been a customer for a really long time. So joining me in person today — my favorite way to do this is in person — is Brian Berger, CEO and founder of Mack Weldon. Brian, thanks for joining me.

Brian Berger

Thanks for having me. And thanks for the compliment on the sweater.

Bryan Mahoney

I get so many compliments on this. I'm wearing Mack Weldon, but for those who are watching or listening — what is Mack Weldon? Tell me a little bit about the brand.

Brian Berger

You're a really good example of our customer. We started the brand — our mission was reinventing men's basics. We were really focused on a very narrow set of product categories that were often overthought: socks, underwear, t-shirts, undershirts — the core essential, foundational items of a guy's wardrobe. The market was all licensed product or mass — Hanes, Jockey, Fruit of the Loom, those types of guys. So we figured there's an opportunity to come in and apply a Lululemon-level product formula to this boring category. Guys care a lot about these things because they're on your body all day, and if you talk to guys, most of them really have opinions about it. So that was our original mission — wrapping it all up in a better customer experience, really rooted in e-commerce in a high-touch way. And over the years, we've been given permission, largely by our consumer, to expand into other product categories — like the sweater you're wearing, or denim. Everything we make is focused on wardrobe essentials, classic menswear. We're not looking at fashion categories, we're not chasing trends. It's about those foundational pieces and applying a very rigorous product formula to it. The sweater you're wearing is cashmere blended with a little bit of Lycra, and the entire inside is lined with CoolMax cotton, so you can wear it without a shirt underneath and it feels great on your skin. Comfort is the punch line for everything we do.

Bryan Mahoney

And there is that level of quality — I've been buying this stuff for at least ten years now, and I still have a lot of the original pieces I bought. One of the things I always found interesting about you is you didn't grow up in this industry, but you really geek out over the technology behind it, the fabric. I'd get emails from you sometimes saying, 'I'm really excited for you to try this, here's why — can you give me feedback?' How did you find your way into this? You clearly care about it.

Brian Berger

It wasn't an accident, but my background is consumer tech. I grew up in early internet, tech media businesses — business models rooted in advertising and sponsorship around content, distributed through the internet. So I had real knowledge about using the internet and digital marketing data to reach consumers. But I was always personally passionate about brands that solved a problem for consumers — whether a better process, a better retail experience, a better product. In my own journey, I'd always believed the end state for me would be applying my background in consumer internet and technology to a more physical, consumer product business. And this category — I was always complaining about t-shirts, underwear, socks. Why can't these be better? Why are we still wearing our grandparents' version? There was no brand here other than Calvin Klein, which was really a licensed product at the time. So I had a window in my career where I could actually focus on this and do it.

Bryan Mahoney

It wasn't with the background you had — I think it would've been easy to spot an arbitrage opportunity, a cohort of customers that might be efficient to acquire. But you told a classic founder story — there was something driving you crazy, something that didn't exist, that you had to go create.

Brian Berger

As the story goes — even from a customer experience standpoint, I was at Bloomingdale's, where I used to buy my underwear once a year, and the sales guy came over and said, 'Are you confused yet?' It was a terrible, confusing experience. I cared about it, I could never find what I liked — it was this total morass of stuff. So why not do it better? That's what we did.

Bryan Mahoney

2012.

Brian Berger

2012. Launched in the summer of 2012.

Bryan Mahoney

And when you launched, you launched entirely digitally native — it wasn't really called DTC yet, it was sort of becoming DTC, right at the beginning.

Brian Berger

Yeah — Andy Dunn, who was a pioneer in consumer apparel — Bonobos and Warby Parker were the two brands that really paved the way for brands like ours, because they showed you could actually build a customer experience, develop the product, deliver the product, and do it all without needing lots and lots of money — or lots and lots of physical locations.

Bryan Mahoney

One of the things I've appreciated watching the arc of Mack Weldon is that you now have a physical retail presence. You've been given permission by your customers to expand your offering — even to expand where you interact with them, into physical space. If you'll indulge me, let's take a trip down memory lane — 2012 to 2026. So much has changed for what it means to be a brand that launched online and is now meeting customers where they are. I always found you were someone who didn't chase trends — a lot of brands raised a lot of VC dollars and went all in on acquiring customers. I know you chased a couple of technology trends along the way, but your approach has always been one of discipline. What advice would you give the Brian of 2014, two years into the journey, watching the DTC explosion around him? What did you get right, and what would you do differently today?

Brian Berger

What we got right was staying really focused. It's easy to get distracted when you're dealing with limited resources — there's a real opportunity cost to chasing trends. In our business, if you make a big bet on a product category that doesn't materialize, that creates real business risk. So we stayed focused — we're trying to expand our aperture a little, in line with customer and brand objectives. In terms of what I'd do differently, and the advice I'd give anybody starting a brand today: try to be in all the places your consumer is, as early as possible. We weren't one of those brands saying 'we're cutting out the middleman, retail sucks' — we didn't believe that. But we did believe the core fundamental of our business model was investing in a customer relationship, and because our product categories were semi-consumable, we'd have a chance at a long-term relationship with that customer — so there wasn't a perceived need for stores. If I could rewind the clock, and I look at some of our peers who've really broken out, I would have gone multichannel — at minimum wholesale, which doesn't cost a lot from a capital perspective — much earlier. You diversify your revenue streams, you can build a profitable revenue stream earlier than DTC in many instances, and it's marketing — it's another channel that isn't Meta and Google that you can show up on for your consumer.

Bryan Mahoney

So durability — how do you build redundancy into the business early on? Through diversification, finding those profitable channels. On the surface you'd think, how can wholesale be more profitable than just acquiring a customer on Facebook or Google? But it takes some experience to know that.

Brian Berger

With wholesale, you're just marking up your product by a little less — you don't have the customer acquisition cost, but you do have cost. You have to hire people to go sell, pay them commission, get a booth at a trade show. But once you get to a certain level, you cover those costs, and if you're doing it right, those are profitable revenue dollars.

Bryan Mahoney

That's a good segue to profitability. You're also known as a CEO who focused on getting profitable maybe before it was fashionable, when everyone else was in growth-at-all-costs mode. How hard was that?

Brian Berger

It's hard because you're constantly in tension between investing in growth and building a sustainable, self-sustaining business. When we started in 2012, there was a lot of investment dollars chasing this category and business models like ours — a huge draw toward chasing that valuation, getting the capital in, hiring a big team.

Bryan Mahoney

For me it felt like a land rush — so much money, you had to hire everyone because if you didn't, your competitor would. I'd imagine it was the same in your space — how do we make sure we get the customer before they get the customer?

Brian Berger

That's the thing, though — it's not a zero-sum game. In technology, maybe Uber and Lyft is zero-sum, maybe ChatGPT and Claude is zero-sum. In our world, it's not. But everyone started to think that way. The world isn't sitting around waiting for the next clothing brand to launch. Customers learn about your brand the way that they do, and obviously you want to do it fast and build enterprise value quickly — everybody's got their motivations. But the need for capital should be directly correlated to the needs of the business. With every dollar you take, the mindset should be: is this taking me further from being a profitable business, or is it helping me advance my goals in line with my profitability goals? We were not always — I mean, now our business is more like, how small can we be in order to build. It's a bit of a different mindset now.

Bryan Mahoney

I want to float a thesis by you — I believe the next wave of these iconic brands, the ones that achieve real commercial success, will be run by teams far leaner than I ever imagined possible. Do you believe we can get there?

Brian Berger

I think that's true. When you really think about the critical needs of the business, they've gotten a lot less complicated. When we started, we were on a tech e-commerce platform that required engineers and product development people. Now we have Shopify and an agency, and one or two people internally on things like creative. We're in a creative revolution right now — what will be acceptable in terms of AI-based creative, and what we'll still need to stay unique. There's still going to be a need for unique creative — we can't have all this sanitized AI creative out in the world. But there will be a place for it, and it will reduce the need you have on your physical team.

Bryan Mahoney

Let's bring it back to the permission your customers and future customers give you to interact with them that way. How do you balance the relationship and trust you've earned with them — and how do you equip your team with the tools they need to deliver the experience that's allowed you to grow for nearly 15 years?

Brian Berger

I've also really evolved on that. There was a time I really believed the perfect CRM strategy, the perfect cohort management, the perfect email subject line were the things that would move the needle on retention and loyalty — and those things matter. But I think they're more like table stakes now. I think what really matters — and this isn't novel — is you need to be delivering a great product, and you need to show up in a really authentic way for your consumer. That can be an email, it can be a partnership with a local — we just did something here in New York with Juice Press we were excited about, around how to start your day off. It can be a killer social or ad campaign. But at the end of the day, you can't really engineer it — the customer is going to buy when they're going to buy. There's only so many times you can hit them over the head with an email saying 'it's time to replenish' — they're probably going to replenish when they want to. A little maybe, but not that much. So you have to be committed to that. There's a level of letting go of control — you don't really have control over your customer. The one thing you have control over is making sure everything they buy from you, they love — and that when you show up in the world, you do it in an authentic, incredible way.

Bryan Mahoney

I think showing up with the right voice at the right time is a great point — it can't only be promotional. Your team does a good job with content, talking about the technology in the product in a way that doesn't feel intimidating — it makes me excited to try it, because you've earned my trust.

Brian Berger

You're listening because we've earned some credibility with you. But that doesn't mean you're going to buy everything in your wardrobe from us, or replenish twice as fast as you used to.

Bryan Mahoney

It just means you make good t-shirts, so you stick around for a while. I get this question a lot — a brand just launching, thinking 'I need a loyalty program' — and I'm never quite sure what to say. Mack Weldon took a little while — you had this innovative bundling system early on, the free shipping calculator was a smart product, and now you have a loyalty program that's gone through a couple of iterations.

Brian Berger

Yeah, it's points-based — you qualify for different tiers that give you benefits beyond just economic ones. There's a percentage of your customers that are going to be motivated by something like that, and you almost have to have it — it's table stakes. But what really creates loyalty is creating awesome products that people are talking about to the people in their life, becoming net promoters on your behalf. The loyalty program is a component of it, but think about the loyalty programs that are most exciting to you — they're usually ones that give you something economic, like a points-based thing. You're psyched about that, but you wouldn't be achieving loyalty with those brands if their product sucked. You're getting to those levels because the product is great, and the loyalty program is just the icing on top.

Bryan Mahoney

How much does your team look at data to help with those decisions today? You were one of the early movers in making those data investments — your team was always pretty data-informed. How has that evolved?

Brian Berger

You get so much data, and the question is can you organize it in a way where it's credible and authoritative. At the beginning, it's 'can I trust this data, do I need some massive sanitizing exercise?' The first step was getting ourselves to a place where everything felt like it was in the right place and was really credible, so we could trust it and cut it in a way that served our needs — and I'd say we do a really good job at that now, but it took a lot of effort to get there. The challenge with data, and propagating it through the organization, is having business owners with a data mindset — knowing what questions to ask the data to serve the business best. Over time we've had to make sure our team is asking the right questions, because otherwise you get into data-for-data's-sake, or data paralysis, people just getting overwhelmed. Getting the data organized, and then asking the right questions — that's actually the more challenging, more unique part.

Bryan Mahoney

One question I get a ton, and I've seen the roles in the organization evolve a lot over the last decade — someone will say 'I need to hire a CMO,' and want that CMO to do brand and voice, and then someone else says the CMO needs to be hyper-analytical. You've had a number of CMOs over the years at Mack Weldon — how do you see the marketing role evolving? If you were advising a young founder on their first key marketing hire, do you skew brand, skew analytical, are they two different roles, or one person in one body?

Brian Berger

I really think there are two different roles. The role of a growth marketer is one of deep analytics, trial and error, iteration and testing — much more of a technical acumen. They don't care what creative you're showing, they're looking at the results, and they want it to perform in line with those results. That doesn't mean it's one-dimensional — you can get a lot of initial sales but not a lot of long-term sales, so how you're saying it still matters, so people feel like they're getting what they bought into. But the skill set you want from a growth person is completely different from what you want from a pure brand person, who needs to think about voice and tone, imagery, design, aesthetic — how you're showing up in the world. They're just different things. If you're actually talking about a CMO, the best ones understand both really well — that's sort of the ivory-tower top job — but I'd argue you need to be a more mature business to really justify that ivory-tower person, because everybody needs to be contributing in a very tangible way in a smaller business.

Bryan Mahoney

Especially now as teams get leaner — I'm seeing more people with decades of experience roll their sleeves back up.

Brian Berger

You have to — it's not a luxury. It's different for a bigger, more mature brand managing agencies. But even a couple-hundred-million-dollar brand, everybody's generally playing a real functional role.

Bryan Mahoney

So you have a director of brand and a director of performance and growth marketing?

Brian Berger

It could be a more senior title, but one group has to justify their budget — this is what we need to meet the deliverables we have — and it's harder for them to specifically track ROI relative to what they're spending. Whereas the growth team are effectively media buyers.

Bryan Mahoney

So one thing growth teams need to think about today is buying media on this new emerging channel — agentic commerce. How is your team thinking about that, if at all?

Brian Berger

Everybody's thinking about it — it'd be more notable not to be. I feel like we're going to start losing productivity before we actually gain it, because — I'll use myself as an example — a couple weeks ago I was like, I have to figure out use cases, in my business life or personal life, to really get exposure to the power of these tools. I know that's happening across everybody's world right now regardless of role. It's even better if you have a specific business problem you're trying to solve, and you use that educational time to try to solve it. Right now we're mostly using it for baseline efficiencies. One great example — we recently had to move warehouses, and there was a situation where we needed to transfer inventory from one place to another in a pretty dynamic way. Charlie, our CFO and COO — an absolute superhero — over the weekend built an app that took a process he would've had to personally micromanage and turned it into one where somebody on his team manages it and he plays more of an oversight role, because he built a really dynamic tool to solve a very specific business problem we had. That's really where I think the power is right now. And then, certainly, things every business like ours does that'll get more productized — like creative development — it's not quite there yet for consumer apparel, consumer CPG, physical product businesses that need physical models. It's amazing for changing backgrounds, lighting, things like that — clothing on a model is almost there, but not quite. And then there's the question of where's the line between 'this is our brand, our proprietary creative,' and 'this is just generic for the catalog.' I'm not quite there yet.

Bryan Mahoney

I love that, because I think the two terms — AI and agents — get conflated a lot. It's interesting to hear the team's already experimenting with tools behind the scenes. An agent is the concept of things doing things on your behalf, and they get their intelligence through AI —

Brian Berger

But in a more distributed fashion versus a centralized one — you're not using one of the big models.

Bryan Mahoney

I'm sure Charlie used a large frontier model to help build what he built. Where I'm curious to get your point of view: in the last couple of months there's been so much buzz around investment going into agent-based shopping — OpenAI had the big announcement, Stripe's been investing in it, Google's been investing in it. When I talk to brands or growth marketers and try to gauge their excitement about their products showing up within ChatGPT, with the customer able to make a direct purchase from within there — even though in recent weeks they've retreated back from that a bit — what I mostly hear is that it's just another channel to manage, in some ways like we have to think about our content the way we did fifteen years ago with SEO, looking for that relevancy. If I'm looking for a really comfortable cashmere sweater I can wear without a t-shirt underneath, instead of opening Google I might ask Claude to find it for me. Is your team thinking about this now? Does it become an important channel for you? You've got a good track record of not chasing trends — how are you balancing this out?

Brian Berger

We're not over-talking on it, but we absolutely see the potential, because of our own behavior — we're all starting to bifurcate how we think about what we used to just go to Google search for, versus what we're using Claude or ChatGPT for, or Gemini. So I'd say we're going to be with the pack on it — we're not losing our minds over it yet.

Bryan Mahoney

Is your team monitoring any traffic coming from these agents? Anything surprising you so far?

Brian Berger

It's surprising that there's a lot of traffic. And it's also really exciting when somebody types in 'what are the best men's boxer briefs' and we're on the list. A lot of that is driven off the block-and-tackle of what we've been doing for the last twelve years — building up our affiliate base, making sure there's as much legitimate third-party content out there about us as possible, because the models are looking at all of that. They're not just coming up with it themselves.

Bryan Mahoney

Is your team trying to — I hate this term — growth-hack their way into that? I've talked to people who've figured out reviews make a big difference in one model, Reddit makes a big difference in another, and they're trying to balance their content attack. But when I hear that, I instantly think of the days we'd figure out the Google algorithm, get onto the first page, then the algorithm changes and suddenly you're on page three, reverse-engineering it again. It feels a bit reverse-engineered to me, and not durable. What advice are you giving your team, or what are you looking at?

Brian Berger

We're still — and maybe we're not at the forefront on this — heavily driving the affiliate side of our business, making sure there's a lot of legitimate third-party content out there about us, because our understanding is that relevancy matters, and that's how the models get their intelligence — by looking out at the world and making a judgment based on what's there. So right now that's really where the effort is. And then there are things we're doing on the site to make sure — I heard 'AIO' is a new term, and there's all these new pieces of terminology, which is great for us, because as tech people we need the acronyms.

Bryan Mahoney

I still haven't been able to figure out exactly what the difference is, if you're building a site that's easily accessible —

Brian Berger

The same things matter — you know this better than anyone — all the things you'd do to search-engine-optimize your site are the same things you'd do for this.

Bryan Mahoney

I want to make it as easy for customers to find us as possible, as friction-free as possible. If we think about these agents — they're not super smart yet in terms of navigation, but they're incredibly powerful when it comes to reasoning. If your checkout works, if it's easy to understand why the product is great, I give the agent an awful lot of leeway to figure that out. It makes me somewhat uncomfortable when I hear about engineering tricks — publishing shadow pages just for the agents that you can't really find as a person, just to give them what they want. That doesn't feel like it's getting us closer to our customer, to being relevant for them.

Brian Berger

We're not doing that yet. But one thing I heard that was interesting the other day — also useful for improving the customer journey, conversion rates, and making growth marketing spend more efficient — is the ability to dynamically produce landing pages tied to specific customer personas, in a much more real-time manner than you were able to do before. We're not doing that yet, but there are brands experimenting with it where the results were pretty compelling.

Bryan Mahoney

That makes sense to me — it's almost the next frontier of personalization, which was another trend maybe ten years ago that never really delivered unless you had a product catalog of a million SKUs. The hyper-personalization piece — I never saw strong ROI on that.

Brian Berger

Because we can create a landing page for a particular product that we think is most likely to convert the highest percentage of customers off a particular ad — but it's not a one-size-fits-all customer. You could have a woman buying for a man, or a 55-year-old affluent guy — the personas are different, and the data exists. So what if you could tweak the experience those customers were having on that landing page to better reflect who they are?

Bryan Mahoney

I like persona-based marketing — there's something that's not fully creepy about it: something about me and the experience is really good, you know what ad resonated with me, so you bucket me into one of your handful of personas and tailor it that way. I think this technology to spin up landing pages quickly is interesting — it's a way to deliver what you think is a better experience given the data you have.

Brian Berger

You remind me of the Claude Super Bowl ads — I thought those were some of the best things I've ever seen, so clever, so straightforward. But there's a point at which it becomes creepy — it's like, I'm giving you advice about your mental health, and now you're serving me ads about it.

Bryan Mahoney

Is there a future where Mack Weldon advertises during the Super Bowl, or on ChatGPT during the Super Bowl?

Brian Berger

After our large investment rounds with private equity, that was always the joke — 'oh, thanks so much, we just booked the Super Bowl.' There's a time and a place for it — not for us, not in the near term. Not a lot of eyeballs relative to a lot of chatter. But in terms of advertising generally, we'll go wherever the customer is — even in the past year, channels like Reddit, which isn't a channel for everyone, worked really well for us based on who the audience is and the ad format. X, too — there was a lot of opportunity to own a bit of share of voice there. A lot of guys there.

Bryan Mahoney

So your customer is — a formula that's worked for you since 2012?

Brian Berger

Most of the time. Every brand has primary and secondary customers — for us in particular, women buy a lot of men's clothing, so we've had to figure out how to speak to guys really well, our core customer, but also develop skills to target women as buyers for men. And the algorithm won't help you there, because it's always going to go to the place where the conversion rate is highest — oversimplifying it, it's hard to force it to do something else. So we've found that podcast advertising, influencer advertising — places where we have a bit more control over who the audience is and making sure the message reaches that audience — have been really effective ways to capture new audiences. But purely algorithm-driven marketing, it's sometimes pretty hard to get away from your most likely customer to start educating and bringing in a secondary customer.

Bryan Mahoney

So there are no shortcuts — you haven't found them yet.

Brian Berger

No. Anything that's good gets oversaturated, or if it's working instantaneously from a marketing standpoint, everybody's there, and then it becomes inefficient. You really just have to be committed to building the muscle and being really disciplined.

Bryan Mahoney

I've had a chance to sit down with probably thirty people in a chair like that and talk about this, and some of the most honest things people have said is there is no shortcut — if there's arbitrage, it's there for a minute, but it's so efficient it's gone. There's no such thing as an overnight success for a brand that has this kind of connection with its customer. You've been doing this for nearly 15 years — I hope you're doing it for the next 15, because I love the clothes. But it comes back to what it's always been: know where your customer is, show up the right way, create great products, and have the durability and resilience to keep doing it.

Brian Berger

In many ways, we started out as an innovative, business-model-driven brand, but we're operating — and all our peers are too — more like traditional consumer apparel brands. We were digital-first, we come at everything from an e-commerce, own-the-customer-relationship perspective. But we're going to trade shows, we're selling into Nordstrom, we're hiring salespeople to sell in specialty stores in all the regions of the country where our customers are — that kind of thing has been done forever. You really have to be doing all of it.

Bryan Mahoney

The more things change, the more they stay the same. I think that's a great place to wrap up. Brian, thank you for finally saying yes — I think the first time I asked, this was a lot of fun.

Brian Berger

I loved it, man. Thank you so much.