Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup

Tanya Golesic, CEO of Mackage: From Canadian down to a Global Luxury Brand

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 [https://open.spotify.com/show/3fpiSlpsAfbLVKaLY5HppF?si=451f892a512b4f2d&nd=1&dlsi=ff22e57c0ac24c52] podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode [https://open.spotify.com/episode/5sGwx2hG75iWvjvEz6GjP4], 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 [https://www.linkedin.com/company/ken-pilot-ventures/posts/?feedView=all&viewAsMember=true], Instagram [https://www.instagram.com/kenpilotventures/], and YouTube [https://www.youtube.com/@TheRetailPilot].  Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

Pete Nordstrom: From public to private, Nordstrom’s gains momentum.

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 [https://open.spotify.com/show/3fpiSlpsAfbLVKaLY5HppF?si=451f892a512b4f2d&nd=1&dlsi=ff22e57c0ac24c52] podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode [https://open.spotify.com/episode/1Ak83n2nuRaibwrDfnvhRb], 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 [https://www.linkedin.com/company/ken-pilot-ventures/posts/?feedView=all&viewAsMember=true], Instagram [https://www.instagram.com/kenpilotventures/], and YouTube [https://www.youtube.com/@TheRetailPilot].  Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup

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 [https://open.spotify.com/show/3fpiSlpsAfbLVKaLY5HppF?si=451f892a512b4f2d&nd=1&dlsi=ff22e57c0ac24c52] podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode [https://open.spotify.com/episode/7flQSuVxqhDFEhseHw0GqA], 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 [https://www.linkedin.com/company/ken-pilot-ventures/posts/?feedView=all&viewAsMember=true], Instagram [https://www.instagram.com/kenpilotventures/], and YouTube [https://www.youtube.com/@TheRetailPilot]. See Mickey Live: Ken and Mickey will be together on stage at Commerce Next [https://community.commercenext.com/] on June 24th - join them for an unfiltered conversation about the craft of retail. Learn More About Alex Mill: * Visit AlexMill.com [http://AlexMill.com] to shop the collection * Follow @AlexMill [https://www.instagram.com/alexmillny/]on Instagram Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

Rhone CEO Nate Checketts on Mind & Body Wellness: How Mental Fitness Built a $100M Performance Brand

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 [https://open.spotify.com/show/3fpiSlpsAfbLVKaLY5HppF?si=451f892a512b4f2d&nd=1&dlsi=ff22e57c0ac24c52] for more conversations with retail industry leaders shaping the future of commerce. Previous episode [https://open.spotify.com/episode/6echNaqwDNtEs9CY9zAXUH]: 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 [https://www.linkedin.com/company/ken-pilot-ventures/posts/?feedView=all&viewAsMember=true], Instagram [https://www.instagram.com/kenpilotventures/], and YouTube [https://www.youtube.com/@TheRetailPilot]. Learn More: Visit Rhone.com [http://Rhone.com] for the 12 Pursuits mental fitness framework and free wall calendar. Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.

Guggenheim Analyst Simeon Siegel: Why Revenue Matters More Than Hype in Retail + 2026 Stock Picks

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 [https://open.spotify.com/show/3fpiSlpsAfbLVKaLY5HppF?si=451f892a512b4f2d&nd=1&dlsi=ff22e57c0ac24c52] podcast for more conversations with retail industry leaders and visionaries shaping the future of commerce. If you missed our last episode [https://open.spotify.com/episode/3wmyPDviAv1SHxBH2tpFvk], 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 [https://www.linkedin.com/company/ken-pilot-ventures/posts/?feedView=all&viewAsMember=true], Instagram [https://www.instagram.com/kenpilotventures/], and YouTube [https://www.youtube.com/@TheRetailPilot]. Hosted on Ausha. See ausha.co/privacy-policy [https://ausha.co/privacy-policy] for more information.