Retail Gets Real Podcast

The digital strategy behind Mack Weldon’s growth

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:

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