The Retail Pilot

When Tanya Golesic took the helm of Mackage in July 2021, she inherited a Canadian brand with extraordinary product and almost no story. "The minute you put the product on, you wouldn't want to take the product off," Golesic tells Ken. "But it was lacking a brand story. It was lacking storytelling." Four years and a record-breaking 2025 later, the former Jimmy Choo president has transformed a down-outerwear specialist into a global luxury lifestyle brand—stretching price points to $3,500, balancing the men's-women's split, and betting on the Croatia national team at the World Cup. This is a masterclass in brand building from someone who learned the craft at Ralph Lauren, Marc Jacobs, Canada Goose, and LVMH. In this episode of The Retail Pilot, Ken sits down with Tanya Golesic, CEO of Mackage, to trace her journey from a Croatian immigrant family in Canada to the top of global luxury fashion, and to unpack how she's scaling Mackage beyond its outerwear roots. This is a conversation about craftsmanship, curation, building inside a private-equity-backed startup, and why fashion has more in common with sports than most people think. In this episode you'll learn: How Tanya went from a Croatian immigrant family in Canada to leadership at Ralph Lauren, Marc Jacobs, LVMH, Canada Goose, and Jimmy Choo Why she turned down Mackage the first time—and how a "six-and-a-half-year interview" led her to the CEO role The "aesthetics that protect" brand ethos: why Mackage product must be fashionable, functional, and technical all at once How Mackage shifted from 50% heavyweight down to a 12-month lifestyle business spanning leather, cashmere, ready-to-wear, and rainwear Why 2025 was a record year with double-digit growth—and how launching a real spring collection unlocked it The logo strategy: segmenting between a "quiet luxury" customer and a streetwear customer with flexible branding How she stretched price points from $850–$1,200 up to $3,500 without raising prices across the board The wholesale discipline: applying the 80/20 rule and pulling back doors to focus on top-tier accounts Mackage's global retail expansion across Canada, the US, Paris, Japan, China, and Korea—and when to use partners vs. going in-house Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Pete Nordstrom unpacks the eight-year journey to go private, the strategic partnership with Liverpool that made it possible, and what's actually changed since May 2025, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.  Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, Ken sits down with Pete Nordstrom – Co-CEO of the 125-year-old fashion retailer – to unpack the eight-year journey to go private, the strategic partnership with Liverpool that made it possible, and what's actually changed since May 2025. They explore why the Saks-Neiman Marcus merger created an opening Nordstrom is now seizing, how the Rack is scaling toward 25+ new stores a year, and where AI is genuinely moving the needle. Pete is candid about the failed 2017 take-private attempt, the Canada expansion that became his generation's "biggest black eye," and why no department store has ever successfully exported its model abroad. This is a conversation about staying relevant across generations, competing with Amazon and Walmart, and the unglamorous discipline of just trying to be the best Nordstrom you can be. In this episode you'll learn: Why Nordstrom went private in May 2025, and why the 2017 attempt failed How the Liverpool partnership came together: 51% Nordstrom family, 49% Liverpool, zero pressure to merge or exit The real downsides of being a public company: morale, distraction, governance overhead, and a stock price tied to a struggling sector narrative What's actually changed day-to-day since going private and the one thing Pete misses about public-company rigor Why Pete sees the Saks-Neiman's merger as a once-in-a-generation opportunity for Nordstrom to capture market share How Nordstrom is winning brand partnerships, top talent (like Yumi Shin from Bergdorf Goodman), and customers from struggling competitors The Rack expansion strategy: 25 stores this year, with capacity to potentially open 50 annually Why Nordstrom Rack competes more with Macy's than with TJ Maxx—and what that means for store growth The competitive reality of Amazon and Walmart in beauty, marketplace, and replenishment, and why Nordstrom can't get left behind Why Nordstrom's marketplace (launched 18 months ago) is one of the company's biggest untapped growth levers The Canada lesson: Why no department store has ever succeeded outside its home country – and what Pete learned from trying What Pete hopes will be true at Nordstrom's 150th anniversary – and why agility matters more than any specific plan Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Mickey Drexler tells all on how he operates with startup intimacy and five decades of wisdom, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.  Hosted on Ausha. See ausha.co/privacy-policy for more information.

Retail icon Mickey Drexler doesn't do retirement. At 80, the man who built Gap into a $14 billion empire, founded Old Navy, and revitalized J.Crew is running Alex Mill like a scrappy startup, and loving it. "I love what I do more now," Drexler says. "I don't have someone breathing down my neck." This is Mickey unfiltered: no corporate boards, no bureaucracy, no focus groups. Just 30 team members, two stores, and a merchant's eye as sharp as when he reinvented Ann Taylor in the 1980s. In this episode of The Retail Pilot, Ken goes behind the scenes at Alex Mill to explore how Mickey operates with startup intimacy and five decades of wisdom. They walk through design boards covered in vintage scarves, discuss why "a great store looks like it was bought by one person," and unpack Mickey's weekend update ritual - clipping magazines, photographing street style, bringing visual inspiration to the team every Monday. In this episode you'll learn: Why Mickey runs Alex Mill with only 30 people and why smallness is an advantage The "white space" strategy: How Mickey identified opportunities at Ann Taylor, Gap, and Alex Mill Mickey's weekend update: How he curates inspiration from magazines, street style, and everyday observations The curation philosophy: Why less is more and how to edit 32 prints down to 3-5 "If you know, you know": Mickey's brand-right approach and why focus groups are the enemy Why AI will never pick colors and what technology can't replace in retail Biggest career mistakes: Hiring wrong executives, opening too many stores, expanding internationally How Mickey got fired from Gap with no notice after building $14B - and what he wishes he'd done Why wholesale helped Alex Mill reach minimums with only two stores The tension between designers (what's next) and merchants (what's been) - and how to bridge it Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Nate Checketts (Rhone CEO) on why wholesale saved his brand, how women's beat 8 years of men's in 2, and building mental fitness into brand DNA, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. See Mickey Live: Ken and Mickey will be together on stage at Commerce Next on June 24th - join them for an unfiltered conversation about the craft of retail. Learn More About Alex Mill: Visit AlexMill.com to shop the collection Follow @AlexMill on Instagram Hosted on Ausha. See ausha.co/privacy-policy for more information.

Most performance apparel brands tell you they're building a lifestyle. Nate Checketts actually means it. As CEO and co-founder of Rhone, he's built a company where mental fitness isn't marketing—it's the foundation. "We say internally that we are a wellness company that just happens to sell clothes," Checketts explains. But here's what makes that more than a tagline: in year two of launching women's apparel, Rhone did more revenue than it generated in its first eight years of men's business combined. In this episode of The Retail Pilot, Ken Pilot unpacks Rhone's unconventional journey—from defying the "wholesale is dead" narrative to launching a women's line that's reshaping the company's trajectory. They discuss why Warby Parker's advice to embrace wholesale early changed everything, how the 12 Pursuits mental fitness framework became both internal culture and external brand positioning, and why Checketts spent years resisting a women's launch before discovering his best customers were already 30% female. In this episode you'll learn: Why Rhone embraced wholesale when every DTC brand said it was dead—and how it drove faster profitability How Rhone's women's business generated more revenue in 2 years than 8 years of men's The mental health crisis that inspired Nate to start Rhone—and why he couldn't build "just another apparel brand" Rhone's 12 Pursuits framework: How Benjamin Franklin's 13 virtues became a scalable mental fitness system Why "commuter" apparel became one of Rhone's biggest categories How Rhone navigated tariffs with a "third, third, third" model—splitting costs between suppliers, margins, and customers The Rerun resale program with Archive: Why high-quality product beats greenwashing Rhone's AI approach across design, merchandising, and customer service—and why "losing your job to someone who uses AI better" is the real risk How Rhone differentiates from Lululemon and Alo by targeting "whole person health" vs. yoga-focused positioning Essential listening for: brand founders navigating wholesale vs. DTC decisions, retail operators building purpose-driven businesses, apparel executives considering gender expansion, and anyone interested in how premium performance brands compete in an oversaturated market. Subscribe to The Retail Pilot for more conversations with retail industry leaders shaping the future of commerce. Previous episode: Simeon Siegel (Guggenheim Securities) on the consumer spending paradox, 2026 stock picks, and why NPS should be banned from boardrooms. Connect: Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. Learn More: Visit Rhone.com for the 12 Pursuits mental fitness framework and free wall calendar. Hosted on Ausha. See ausha.co/privacy-policy for more information.

Retail earnings season just wrapped, and the headlines are telling one story while the data tells another. Consumer sentiment is dismal. Tariffs are squeezing margins. Geopolitical uncertainty looms. Yet average retail revenues grew 7-9% in Q4, and consumers keep spending. How do you reconcile these contradictions? Simeon Siegel, Senior Managing Director at Guggenheim Securities and one of Wall Street's most data-driven retail analysts, cuts through the noise with a simple philosophy: "The first thing I look at is revenues. Because it's very easy to conflate growth rates with revenue sizes." In this episode of The Retail Pilot, Ken sits down with Siegel to dissect what's really happening in retail beyond the sentiment surveys and macro doom-scrolling. From Nike's "dying" $47 billion business to Gap's viral comeback, from the D2C myth to why NPS scores should be banned from boardrooms, Siegel brings his signature contrarian analysis backed by hard numbers. This isn't about feelings—it's about what consumers are actually doing with their wallets, which stocks are positioned to win, and why the retail industry's most cherished beliefs might be leading CEOs astray. In this episode you'll learn: Why consumer spending remains strong despite abysmal consumer sentiment—and what that divergence really means The revenue vs. narrative disconnect: How Nike can be "dying" with $47-49 billion in sales Which retail subsectors are winning and losing in the K-shaped economy (hint: it's a market share story, not a demographic one) Simeon's top stock picks for 2026: Why he's bullish on Nike, TJX, Ross, Birkenstock, Planet Fitness, and Capri The real impact of tariffs on Q4 earnings: What retailers passed through vs. what they absorbed Why Gap Inc.'s comeback under Richard Dickson is working—and whether it's sustainable beyond the hype The one KPI Simeon wants banned from retail boardrooms: Net Promoter Score (NPS) and why it misleads executives Why "D2C is not all it's cracked up to be": The data-driven case for wholesale distribution How the Iran conflict could impact consumer spending, gas prices, and petroleum-based athleisure costs The department store survival blueprint: What Macy's, Nordstrom, and off-price retailers are getting right Why TJ Maxx's lack of e-commerce is actually an asset for moving premium brand inventory "invisibly" Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Terry Lundgren (former Macy's CEO) and Jan Rogers Kniffen dissect the Saks Global bankruptcy, predict the future of department stores, and reveal why some retailers will survive while others won't, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. Hosted on Ausha. See ausha.co/privacy-policy for more information.

The department store industry just witnessed one of its most dramatic collapses. When Saks Global filed for bankruptcy in early 2026, it marked the end of an ambitious—but fatally flawed—attempt to merge two luxury retail icons.  For Terry Lundgren, former Chairman and CEO of Macy's, and Jan Rogers Kniffen, one of retail's most respected strategists, the failure was inevitable. "Putting two very weak financially organizations together will not make anything other than one big financially weak organization," Lundgren warned before the deal even closed.  In this episode of The Retail Pilot, host Ken Pilot brings together two industry veterans who've navigated mergers, bankruptcies, and retail transformation for decades. They reveal what killed Saks Global, why some department stores will survive while others won't, and what the retail landscape will look like in 2026 and beyond. In this episode you'll learn: Why the Saks Global and Neiman Marcus merger was "DOA" from the beginning and what red flags signaled the collapse How Terry Lundgren successfully executed one of retail's most successful acquisitions: the May Department Stores deal that created a national Macy's footprint Why department stores aren't broken—just overleveraged—and how the right balance sheet can save the model The "My Macy's" strategy: How localized assortments and 70 district buying teams drove billion-dollar growth The marketplace opportunity: How third-party sellers can expand assortments without inventory risk Why physical stores still matter and how to make them "fun" again with experiential retail, restaurants, and curated galleries Walmart's dominance: How they're "firing on all cylinders" and taking market share from Target, Kohl's, and JCPenney Amazon's retail store struggles and why they should "buy somebody that has stores and let them run it" The future in 10 years: Which department stores will survive (spoiler: Macy's, Bloomingdale's, Nordstrom, and Dillard's) What it takes to save Saks and Neiman Marcus: A "white knight with deep pockets" and a long-term vision This episode is essential listening for retail operators managing consolidation and change, investors evaluating the department store sector, vendors navigating complex retail partnerships, and anyone seeking to understand the forces reshaping American retail from two executives who've been at the center of it all. Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Lizanne Kindler, CEO of Knitwell Group, shares how she leads eight iconic fashion brands generating over $6 billion in revenue and successfully integrated three separate companies into one unified powerhouse, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. Hosted on Ausha. See ausha.co/privacy-policy for more information.

What does it take to lead eight iconic fashion brands generating over $6 billion in revenue? Lizanne Kindler's journey began at age 11 in a Washington D.C. department store, where her aunt—then president of the Garfinckles chain—gave her a glimpse into the magic of retail. "I remember feeling the buzz, the energy, the beauty," she recalls.  That transformative summer set a young Danish girl on an unlikely path: move to America and build a career in fashion retail. Today, as Executive Chair and CEO of KnitWell Group, Kindler oversees Ann Taylor, Loft, Talbot's, Lane Bryant, Chico's, White House Black Market, and Soma—proving that childhood dreams fueled by curiosity and determination can reshape an entire industry. In this episode you’ll learn: -How a childhood experience in a D.C. department store sparked a lifelong passion for fashion retail -The strategy behind merging three separate companies into one unified $6+ billion powerhouse -Why brand marketing is "really back at the center" after years of performance-focused strategies -How growing up with deaf parents shaped Kindler's leadership style and ability to synthesize complex information -Why 75% of retail sales still happen in physical stores despite the digital revolution -The secrets behind Loft's "Summer of Loft" campaign and its massive customer acquisition success -How to maintain distinct brand DNA while managing eight different fashion brands -Micro-influencer strategies and the return of cultural relevance in marketing Whether you're interested in brand building, modern marketing strategies, organizational integration, or want insider insights on leading a multi-brand retail empire, this conversation offers actionable lessons on managing complexity at scale. Don’t forget to subscribe to The Retail Pilot podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode, where Amy Errett shares how she built Madison Reed into a high‑growth, tech‑powered beauty company with hundreds of millions in revenue and a fiercely loyal customer base, be sure to tune in. Connect with Ken: -Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. Hosted on Ausha. See ausha.co/privacy-policy for more information.

Amy Errett didn’t just enter the hair‑color category — she rewired it. In a space dominated by legacy brands, fragmented salons, and decades of “the way it’s always been done,” she built Madison Reed into a high‑growth, tech‑powered beauty company with hundreds of millions in revenue and a fiercely loyal customer base. In this conversation, Amy shares how she trusted her operator instincts, spotted a massive overlooked category, and built a business with SaaS‑like retention in a consumer wrapper. She breaks down the early decisions that shaped Madison Reed’s trajectory, the pivotal moment Ulta came calling, and how the pandemic revealed the company’s grit, resilience, and product superiority. We also explore how AI became a foundational advantage from color‑matching and personalization to labor modeling and customer experience and why staying obsessively focused on one thing has become Madison Reed’s moat. If you’re interested in category disruption, operational excellence, or building a brand that scales with intention, this episode is a masterclass in modern leadership. Show Notes • Amy’s shift from investor to operator and the “itch” she couldn’t ignore • Why hair color is a massive, misunderstood category hiding in plain sight • The early DTC years and the product‑quality proof points that changed everything • How Ulta became a breakthrough moment — and why Amy almost said no • The pandemic surge: demand, resilience, and the unexpected acceleration • Scaling from six stores to nearly 100 and building a membership‑driven model • The role of AI in formulation, staffing, personalization, and customer care • Why Madison Reed stays laser‑focused on hair color instead of expanding broadly • The economics behind the business — recurring revenue, retention, and margins • Amy’s perspective on IPO potential and why predictable revenue matters • International expansion, retail partnerships, and what’s next for the brand If you’re building, scaling, or reinventing a category, this episode is packed with insights you won’t want to miss. Listen now and subscribe to The Retail Pilot for more conversations with leaders shaping the future of retail. Hosted on Ausha. See ausha.co/privacy-policy for more information.

NRF President and CEO Matt Shay joins The Retail Pilot to break down what is really happening inside retail as the holiday season reaches its peak. From consumer resilience and record setting holiday sales forecasts to tariffs supply chain challenges and pricing pressures this conversation offers a clear view of the forces shaping retail performance right now. Matt shares how retailers are navigating uncertainty while continuing to execute at a high level and why consumers remain the driving force behind the economy. The discussion also explores how AI is being applied across retail operations from supply chain and fulfillment to marketing customer engagement and in store experiences and why AI is becoming a powerful equalizer for mid size retailers. Show Notes • Introduction and welcome to Matt Shay • The state of the consumer heading into the holiday season • Why retail performance remains strong across categories • NRFs outlook on holiday sales and economic confidence • The impact of tariffs on pricing supply chains and planning • Why uncertainty has made this year especially challenging for retailers • How AI is being used across retail today • AI and its role in customer experience and brand storytelling • What CEOs are saying about AI and the future of jobs • Why physical stores continue to matter • Gen Z and renewed energy around in store shopping • What to expect from NRF 2026 and upcoming industry priorities • Key questions mid size retailers should ask after the holidays • Rapid fire questions to close out the conversation If you found this episode valuable subscribe to The Retail Pilot for more conversations with leaders shaping retail today. Share this episode with your team and leave a review to help others discover the show. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, we sit down with Gene Pressman, a third-generation leader behind the iconic Barneys New York, to unpack how a single store became a cultural force. From redefining American fashion to championing emerging designers, Gene shares the behind-the-scenes decisions, risks, and creative instincts that shaped Barneys into more than retail—it became an experience. Gene reflects on growing up inside the business, learning from his father and grandfather, and helping transform Barneys from a men’s discount store into a global destination for innovation, humor, and uncompromising taste. The conversation spans pivotal moments like discovering Giorgio Armani, building the women’s business, creating unforgettable windows and advertising, expanding globally, and navigating the realities of rapid growth. This is a candid, thoughtful look at creativity versus data, risk-taking versus safety, and why true merchants don’t give customers what they ask for—they give them what they don’t know they want yet. Show Notes Gene Pressman’s role in transforming Barneys New York into a cultural and retail icon Growing up in the Pressman family and learning the business from the ground up How Barneys introduced American audiences to designers like Giorgio Armani, Comme des Garçons, Dries Van Noten, and more The shift from men’s fashion to building a groundbreaking women’s business Why humor, irreverence, and creativity were central to Barneys’ DNA The decision to take advertising and creative in-house and what made Barneys’ campaigns unforgettable Expansion to Madison Avenue, Los Angeles, and Tokyo—and the challenges that came with growth Balancing creative vision with financial realities in large-scale retail Why data can’t replace instinct in merchandising and brand building Reflections on legacy, culture, and what Barneys represented beyond shopping If you enjoyed this conversation, subscribe to The Retail Pilot and leave a review—it helps more listeners discover the show. For the full story behind Barneys’ rise, challenges, and lasting impact, check out Gene Pressman’s memoir They All Came to Barneys. Follow The Retail Pilot for more conversations with the leaders shaping retail, culture, and brand innovation. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode, Ken Pilot speaks with Lew Frankfort, CEO of Coach, who helped guide the company from a $6 million leather goods business to a global brand generating more than $5 billion in annual sales. Over 35 years, Frankfort helped define Coach’s culture, expand its product vision, grow internationally, and strengthen its connection to the consumer. He reflects on the decisions that shaped the company’s growth, the values that guided his leadership, the importance of collaboration, and the role of customer insight in every major step. Frankfort also shares how he evaluates emerging consumer brands today through his work at Benvolio Group. The conversation provides a clear look at how purposeful leadership, strong teams, and consumer understanding can shape a brand’s trajectory. Show Notes – How Frankfort first learned about Coach and why he decided to join the company – Early observations about customers, product loyalty, and unmet demand – The growth journey from $6 million to $5 billion and the decisions that supported it – The meaning behind “magic + logic” and how it guided product and brand development – Why consumer insight was central to Coach’s identity and long-term success – Building strong teams through immersive interviewing and shared values – Encouraging collaboration between creative and business departments – Approaching retail before “omni-channel” was defined: stores, catalog, outlets, wholesale, and early e-commerce – Lessons learned from major turning points, including Coach’s path to independence If this conversation resonated with you, share it with someone interested in retail, brand building, or leadership. Subscribe to The Retail Pilot for more conversations with leaders shaping the future of the industry. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, I sit down with David Lafitte, CEO of Tecovas, the Austin-based Western footwear and apparel brand reshaping what it means to build a premium lifestyle business. From radical hospitality to strategic wholesale expansion, David shares how the company has scaled past $200M+, opened more than 50 stores, and become one of the most influential names in modern Western retail. He walks through his unexpected journey from law to leading high-growth consumer brands, his operational philosophy, and what it takes to build a team capable of sustaining long-term momentum. This conversation offers a rare, inside look at brand building, product strategy, retail expansion, and navigating explosive consumer demand, all rooted in the Western lifestyle movement. Show Notes How Tecovas grew into a $200M+ brand with more than 50 stores nationwide The brand’s shift from digitally native to an omni-channel powerhouse Radical hospitality and how it differentiates Tecovas in-store Product strategy including women’s growth, denim, shirting, and lifestyle expansion Wholesale partnerships with Nordstrom, Dillard’s, and independent Western stores The cultural tailwinds driving Western’s resurgence Using AI to optimize inventory, customer experience, forecasting, and store allocation Lessons from taking over leadership from a founder International expansion opportunities and operational discipline Enjoy 20% off at Tecovas with the exclusive code PILOT20 at checkout. 👉 Shop Tecovas and use PILOT20 for 20% off. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, Ken Pilot sits down with visionary entrepreneur Gregg Renfrew, founder of BeautyCounter and now Counter, to explore what it truly means to disrupt an industry—twice. After building a billion-dollar brand and selling it to The Carlyle Group, Gregg faced the highs and lows of leadership, loss, and redemption. When BeautyCounter collapsed, she made the bold move to buy it back—relaunching as Counter with a renewed focus on transparency, high performance, and sustainability. Gregg shares her personal journey of reinvention: from navigating private equity to reclaiming her mission, empowering women entrepreneurs, and redefining what clean beauty means today. She also reveals how Counter is using modern tech, authentic storytelling, and a new direct-to-consumer model to reconnect with customers who care about purpose and performance. If you’re an entrepreneur, founder, or creative leader determined to rise again after setbacks, this episode offers a masterclass in resilience, reinvention, and leading with vision. Show Notes: The environmental wake-up call that sparked Gregg’s clean beauty mission How BeautyCounter grew into a billion-dollar global movement Lessons from losing control and the courage it took to buy it back The strategy and heart behind launching Counter Why she dropped “Beauty” from the brand name and what it symbolizes The evolution of community-driven commerce and micro-influencer partnerships Using AI, tech, and storytelling to deepen customer relationships How Counter is reshaping clean beauty standards with integrity Gregg’s advice for women raising capital and owning their power in male-dominated rooms The importance of humility, courage, and knowing when to reinvent Listen if you love: stories of comeback, entrepreneurship, clean beauty innovation, and women redefining leadership on their own terms. Subscribe to The Retail Pilot wherever you get your podcasts and visit counter.com to explore the new collection. Use code PILOT20 for 20% off your first order—exclusive for our listeners. Follow @theretailpilot for more founder stories shaping the future of retail. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot Podcast, host Ken Pilot welcomes David Lauren, Chief Branding and Innovation Officer at Ralph Lauren. Together, they dive deep into the brand’s 25-year evolution under David’s leadership from pioneering digital storytelling and shoppable windows to launching Ask Ralph, the company’s first consumer-facing AI styling tool. Lauren shares how the balance between creative vision and business discipline has kept Ralph Lauren both timeless and modern, while exploring the future of retail innovation, artificial intelligence, and global brand storytelling. Listeners will also hear exclusive insights into the company’s hospitality ventures, the magic behind its immersive retail experiences, and a personal look at Ralph Lauren’s legacy, culminating in his recent Presidential Medal of Freedom honor. If you’ve ever wondered how a heritage brand like Ralph Lauren continues to innovate while staying true to its identity, this episode is a masterclass in vision, leadership, and enduring style. Show Notes Topics covered: The evolution of Ralph Lauren from wholesale to a 70% direct-to-consumer brand How Ask Ralph, the brand’s new AI-powered personal styling tool, is redefining the shopping experience Balancing technology and tradition: using AI without losing authenticity The enduring influence of Ralph Lauren’s creative philosophy and brand discipline Behind the scenes of Ralph Lauren’s innovation milestones from shoppable windows to interactive apps Global expansion and the rise of Ralph Lauren hospitality, including The Polo Bar and Ralph’s in Paris The future of AI in retail and storytelling and why the human touch still matters most Ralph Lauren’s success story isn’t just about fashion — it’s about vision, storytelling, and timeless innovation. If you enjoyed this episode, subscribe to The Retail Pilot Podcast for more insider conversations with retail visionaries shaping the future of fashion, business, and innovation. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, Sarah Davis and Ben Hemminger, co-founders of Fashionphile, share the remarkable journey of building the largest online platform for buying and selling ultra-luxury handbags and accessories in the U.S. From its beginnings as a small eBay shop in 1999 to a multimillion-dollar brand with flagship locations in New York and California, Fashionphile has become a pioneer in luxury re-commerce. Sarah and Ben open up about the early challenges of earning consumer trust, overcoming the stigma around pre-owned luxury, and building a model based on authenticity, innovation, and customer experience. This episode dives into the mechanics of luxury resale, from authentication and pricing to the customer behaviors driving growth. Sarah and Ben also share candid insights on leadership, entrepreneurship, and what it takes to scale a business from a basement to a global stage while staying true to their vision of making pre-owned luxury both legitimate and desirable. Together, Sarah and Ben discuss: • The origins of Fashionphile and how they recognized the opportunity in luxury resale • The importance of authenticity and dispelling myths about pre-owned goods • How a 90210 address and Rodeo Drive proximity built credibility with customers • The difference between Fashionphile’s model and competitors like The RealReal and Rebag • Why their buyout approach creates stronger customer trust and profitability • The partnership with Neiman Marcus and now Saks Global, and how it has fueled growth • Their vision for international expansion and the untapped opportunities in luxury re-commerce • Leadership lessons from building a family business and keeping a team motivated by vision Tune in now to hear how Fashionphile is transforming the way the world thinks about luxury resale. And remember — subscribe so you never miss an episode of The Retail Pilot. Hosted on Ausha. See ausha.co/privacy-policy for more information.

What does it take to lead an iconic luxury brand into the future while navigating industry disruption, shifting consumer expectations, and bold strategic moves? For Marc Metrick, CEO of Saks Global, it is about scale, innovation, and putting the customer at the center of every decision. From steering Saks through its $2.7 billion acquisition of Neiman Marcus Group to launching “The Art of You,” Marc is redefining what luxury retail looks like in a digital-first world. In this episode of The Retail Pilot, we explore how Saks is transforming its business model, leveraging data and partnerships with Salesforce. ARG and Amazon, and building a new vision of personalization that resonates with today’s luxury consumer. Marc and I had a brief discussion around Saks product being available on Amazon. He is incredibly excited about their Amazon business (only partial catalog available). Saks Global is delivering new customers with high value. Due to certain statistics that we discussed, we had to eliminate the segment. In this conversation, Marc shares: • The strategic logic behind combining Saks, Neiman Marcus, and Bergdorf Goodman into one powerhouse • How “The Art of You” is taking personalization beyond buzzwords to create truly individualized shopping experiences • The role of technology, AI, and data in modernizing operations and elevating the customer journey • What partnerships with Amazon and Salesforce have unlocked in terms of scale, efficiency, and innovation • How Saks is rebuilding trust with vendors and strengthening relationships with brand partners • Why the US is poised to be the fastest growing luxury market in the world • His optimism about a new generation of digitally native, experience driven luxury consumers Whether you are a retail executive, brand strategist, or simply fascinated by the future of luxury, this episode offers a rare inside look at how one of the industry’s most influential leaders is reshaping the way we think about scale, personalization, and the customer experience. If you enjoyed this conversation, follow and rate the show and share this episode with someone who is curious about the future of luxury retail. The next big insight could be one listen away. Hosted on Ausha. See ausha.co/privacy-policy for more information.

What does it take to stay relevant in the fast-moving world of Gen Z and Gen Alpha? For Brieane Olson, CEO of PacSun, it’s all about purpose, co-creation, and bold innovation. From signing the Jenner sisters before they became household names to bringing PacSun into Roblox and TikTok Shop, Breanne has made youth culture the company’s North Star. In this episode of The Retail Pilot, co-hosted by Melissa Gonzalez, we dive deep into how PacSun evolved from a legacy mall brand to a billion-dollar leader in digital-first, Gen Z–centric fashion and what other retailers can learn from their fearless approach. In this conversation, Brieane shares: Her start in retail at age 15 and journey to the CEO seat How co-creation with micro-creators is driving viral sales and brand affinity The power of music, festivals, and physical retail in the digital age How PacSun uses AI across its stores, associate experience, and creative strategy The evolving role of Gen Alpha and why brands must meet them where they are Why social commerce is no longer optional and how to build it authentically Her leadership philosophy rooted in purpose, curiosity, and constant evolution Whether you're a retail executive, marketer, founder, or just obsessed with youth culture trends, this episode is full of actionable insights on what it takes to lead with relevance, empathy, and a fearless willingness to evolve. If you loved this conversation, don’t forget to follow and rate the show, and share this episode with someone who’s building the next big thing in retail. Your next favorite strategy might just be one listen away. Hosted on Ausha. See ausha.co/privacy-policy for more information.

What happens when a former lawyer walks out of a high-end jewelry store and into a tattoo parlor—and realizes neither is the right fit? You get Studs—a game-changing brand that’s reinventing the ear piercing and jewelry experience for a new generation of consumers. In this episode of The Retail Pilot, we sit down with Anna Harman, co-founder and CEO of Studs, to explore how she went from litigation and asset management to building one of the most profitable and experiential brick-and-mortar concepts in retail. With over 30 locations and sky-high four-wall profits, Studs is challenging legacy brands and tattoo shops alike with its safe, stylish, and millennial-friendly approach to ear piercing. Anna shares insights on: Her unlikely journey from law school to launching Studs The “aha” moment that sparked the idea What makes Studs profitable from day one The real competitors (hint: it’s not who you think) How she applies startup and retail incubator lessons to build a brand with soul Why lab-grown diamonds and curated collabs are driving Gen Z and millennial loyalty Her transparent, feedback-forward leadership style and how it shapes team culture Whether you're a brand builder, founder, retail executive, or just love a good reinvention story, this episode is packed with tactical gems and inspiring takeaways. Ready to reimagine what retail can look like when experience comes first? Follow, rate, and share this episode with a friend and if you’re curious about where to get pierced next, check out studs.com to explore their latest studio openings. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, host Ken Pilot sits down with the visionary team behind RetailClub: Anil D. Aggarwal, CEO & Co-Founder, Simran Rekhi Aggarwal, President & Krystina Gustafson, Chief Content Officer & Co-Founder. Known for creating transformative events like Shop Talk and Grocery Shop, this team is once again leading retail into its next great evolution, this time with AI at the center. Together, they discuss the why behind RetailClub, a new kind of gathering designed to bring together AI-curious, AI-championing, and AI-implementing professionals from across the retail industry. Unlike traditional conferences, RetailClub is a dynamic community and immersive experience complete with beachfront workshops, open-air keynotes, and the kind of deep, meaningful dialogue that can only happen face-to-face. You’ll hear how this initiative is less about flashy tech demos and more about building real, practical fluency in AI across functions from merchandising to marketing to customer service and preparing leaders to navigate exponential change. Whether you're just starting to explore AI or already leading its charge, this conversation will show you why RetailClub is the place to be. Key Themes: The story behind RetailClub and its founding vision Why retail needs a new kind of AI-native community How AI is transforming roles, business models, and entire org charts What makes RetailClub different from every other event on the calendar A glimpse into the AI Deep Dive retreat in Huntington Beach Want in? RetailClub’s first retreat takes place September 14–17 in Huntington Beach, CA. This is more than a conference it’s a curated movement to shape retail’s AI-powered future. Don’t miss it. Hosted on Ausha. See ausha.co/privacy-policy for more information.

In this episode of The Retail Pilot, we sit down with Molly Howard, cofounder and CEO of La Ligne, the beloved fashion brand known for its effortless aesthetic, powerful storytelling, and slow burn sustainable success. Molly shares her fascinating path from private equity and investment banking at Credit Suisse to working at Rag & Bone and ultimately launching La Ligne with former Vogue editors Meredith Melling and Valerie Macaulay. You’ll hear how her finance background uniquely shaped the brand’s business model, why La Ligne prioritized profitability over hype, and how her cofounder chemistry laid the foundation for trust and longevity. Molly also opens up about navigating tariffs, scaling e-commerce thoughtfully, and the turning point that made her realize they needed to “drop product like a magazine” to keep customers returning weekly. Whether you're a founder, fashion lover, or just obsessed with good retail strategy, this is a must-listen conversation filled with lessons in leadership, resilience, and intuition. Show Notes: • Molly’s unexpected journey from Credit Suisse to the fashion industry • The early days at Rag & Bone and the deal that flipped her role from banker to brand-side strategist • How a boat ride in Hawaii turned into a cofounder pitch • The vision behind La Ligne’s name and how they built a brand rooted in non-fussy French minimalism • Why La Ligne raised under $4 million and how they’ve remained profitable ever since • The benefit of launching without institutional investors • Dividing responsibilities among three cofounders and why “three is easier than two” • Building a direct-to-consumer first model with mindful wholesale partnerships like Net-a-Porter and Shopbop • The challenges and creativity that came from growing without an early e-commerce hire • Influencer marketing, ShopMy, and keeping authenticity at the center • The La Drop strategy and why weekly product releases became key to customer loyalty • Facing down supply chain shocks and rising tariffs while keeping the brand nimble • The joy of physical retail and Molly’s passion for designing store spaces • Denim, menswear, and collaborations as La Ligne’s next frontiers • Rapid fire: Molly’s favorite brands, best advice received, go-to pieces, and the Tupac class that shaped her thinking Like what you hear? Follow The Retail Pilot and leave us a review. Share this episode with a friend who loves fashion or dreams of launching their own brand. You can also tag us on Instagram with your takeaways—we’d love to hear what inspired you. Hosted on Ausha. See ausha.co/privacy-policy for more information.