The Retail Pilot

Ken Pilot
  • 4.6 (29)
  • Management
  • Updated Weekly

The Retail Pilot is a series of interviews conducted by Ken Pilot with “Leaders and Legends” of the Retail industry. Ken will focus the conversation on his guests’ career journeys and their greatest career accomplishments and disappointments; gather insight into their leadership styles; learn who inspired them as they progressed through their careers; identify brands they admire; discover challenges they have faced; and talk about where they think Retail is headed and how they are leveraging technology to get there. Hosted on Ausha. See ausha.co/privacy-policy for more information.

  1. 2d ago

    Shea Jensen, President of Urban Outfitters North America: Inside the Brand's Comeback

    When Shea Jensen took over as President of Urban Outfitters North America in February 2024, the brand was posting double-digit comp declines. Eighteen months later, it's posting double-digit comp gains. "It's much more fun to go backwards in time when you're serving customers than forwards in time," Jensen tells Ken. "Nothing's better than going back to college." Jensen spent 35 years at Nordstrom, starting in a stock room at age 15, and is running one of retail's most-watched turnarounds by doing the unglamorous work: rebuilding BDG denim as a category authority, stretching Out from Under into lounge and athleisure, right-sizing the fleet, and meeting Gen Z where they actually live, on Reddit – on Pinterest, and now on DoorDash. In this episode of The Retail Pilot, Ken and co-host Melissa Gonzalez sit down with Shea Jensen, President of Urban Outfitters North America, to unpack the strategy behind the brand's comeback. They explore the customer-first product philosophy driving BDG denim and Out from Under, the four-tier store strategy, the fleet right-sizing that unlocked productivity, the digital channels that actually matter for Gen Z , the DoorDash partnership pulling last-minute shoppers, and the collabs with Chipotle and Dunkin' that turned into cultural moments. In this episode you'll learn: Why Urban Outfitters is going backwards in time to win with Gen Z and Gen AlphaThe BDG denim strategy: premium denim at a non-premium price, building fit franchises with staying powerHow Out from Under became a lounge and athleisure powerhouse without trying to compete with LululemonThe price elasticity playbook: covering opening, mid, and best price points to serve every customerUrban's four store types: high-profile, community, college, and core doorsThe fleet right-sizing story: going from oversized boxes to a 7,000–9,000 sq ft sweet spotWhy Reddit, Pinterest, connected TV, and TikTok are driving discovery, not Facebook or Instagram aloneThe DoorDash partnership pulling customers in on Thursday and Friday afternoonsThe Chipotle, Dunkin', and beverage collabs turning brand partnerships into cultural momentsThe one piece of career advice Shea would give her younger store manager selfThis episode is for you if: you're a retail operator running a turnaround, a merchant balancing private brands and national brands, a marketer trying to reach Gen Z where they actually are, a store designer rethinking format, or a brand leader curious how one of retail's most iconic names is rebuilding its cultural relevance. 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 Neil Saunders, Managing Director and Retail Analyst at GlobalData, unpacks the biggest stories shaping retail in the back half of 2026, 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.

    Shea Jensen, President of Urban Outfitters North America: Inside the Brand's Comeback

  2. Aug 4

    Neil Saunders, Managing Director of GlobalData: Inside Retail's Winners, Losers & the Back Half of 2026

    There's a common assumption in retail right now that the top of the market is the only thing growing. Neil Saunders, Managing Director of GlobalData Retail and one of the industry's most-followed analysts, doesn't buy it. "Every broad income group has contributed to the increase in retail sales," Saunders tells Ken. The K-shaped economy is real, he argues, but it's hiding in the volume numbers, not the dollars. It's one of many contrarian reads he brings to this wide-ranging conversation on the state of retail in 2026, from tariffs and consumer resilience, to why Lululemon's stores now feel "sterile," and which retail names he'd put his own money behind today. In this episode of The Retail Pilot, Ken sits down with Neil Saunders, Managing Director and Retail Analyst at GlobalData, to unpack the biggest stories shaping retail in the back half of 2026: the tariff pass-through math (roughly 40–45% to consumers), the K-shaped consumer decoded, the denim wars between Levi's, Gap, and Abercrombie, the athleisure shift away from Lululemon toward Vuori and Alo, the department store resurgence under merchant-led leaders at Macy's and Saks, Walmart's move on the $100K+ household, and where AI is actually delivering results. In this episode you'll learn: The tariff pass-through math: ~40–45% of costs pushed to consumers, the rest absorbed through sourcing shifts and margin The K-shaped consumer, decoded: why the real divergence is hiding in volume, not value Why the first half of 2026 was propped up by tax refunds and what that means for the back half How Gap's "cultural currency" strategy under Richard Dickson is pulling younger customers back The athleisure shift: why Lululemon is losing ground to Vuori, Alo, and Abercrombie's YPB Why department stores aren't going extinct and why Tony Spring at Macy's is Neil's pick for best retail CEO Walmart's move on the $100K+ household and why they still behave like a small entrepreneurial retailer The global fast fashion breakdown: why Uniqlo is winning, Zara is mature, and H&M feels like "yesterday's retailer" This episode is for you if: you're a retail operator trying to read the macro signal from the noise, a brand leader benchmarking your category's competitive landscape, an investor tracking public retail names into the back half of 2026, a marketer thinking about cultural currency and celebrity partnerships, or anyone who wants a candid analyst read on who's actually winning in retail right now. 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 CEO of Vuori, Joe Kudla unpacks how a former CPA and fashion model turned a men's yoga apparel gap into one of the most admired brands in performance wear, 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.

    Neil Saunders, Managing Director of GlobalData: Inside Retail's Winners, Losers & the Back Half of 2026

  3. Jul 21

    Vuori Founder Joe Kudla: From Garage Startup to $5Billion+ Activewear Brand

    When Joe Kudla launched Vuori out of a Southern California garage in 2013, he was betting against his own track record. He'd already tried the apparel business twice and failed both times. He had a comfortable life, a thriving financial consulting firm he'd built to hundreds of employees, real financial independence, the kind of success that came from humble beginnings near Seattle. And he walked away from it. What pulled him back was a men's activewear gap nobody else was serving and a creative pull he'd spent years ignoring. "I just didn't want to look back and be like, yeah, I wanted this so bad, but I never really jumped in with two feet," Kudla tells Ken. With $400K from friends and family and two employees who are still with him today, he went all in. Sixteen years later, Vuori is a billion-dollar global brand valued north of $5 billion, spanning 100+ stores, 30+ countries, and 3,000+ employees, and here's the kicker: he built the entire thing having put only about $2M on the company's balance sheet. In this episode of The Retail Pilot, Ken sits down with Joe Kudla – Founder and CEO of Vuori – to unpack how a former CPA and fashion model turned a men's yoga apparel gap into one of the most admired brands in performance wear. They explore the founding story, the fabric-first product philosophy, the community-driven retail model that started in a 3,000-square-foot popup doubling as an art gallery, the REI break that opened wholesale, the capital strategy that returned $1.2B+ to shareholders, and the tariff playbook that protected quality over margin. In this episode you'll learn: The white space that launched Vuori: an underserved men's yoga market 2x the size of surfing, and activewear you'd want to live in, not change out ofWhy raising money in 2013 was "almost impossible", and how $400K from friends and family got it startedHow the first store became a community hub, art gallery, and office all at onceThe REI break that proved premium men's athleisure could be a wholesale categoryHow Vuori hit profitability by 2017 with the office in the backstock roomThe capital strategy most people misunderstand: $1.2B+ raised for shareholders, only ~$2M put on the balance sheetThe international growth story: from a beach town in Encinitas to customers in China and KoreaHow Vuori handled the tariff hit: don't panic, never cut corners, and split the cost three waysThe leadership philosophy: a "no drama" culture policy, fabric-first meetings, and why Kudla is still the fit model 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 James Reinhart, Co-Founder and CEO of Thredup, explains how he built one of the most operationally complex companies in fashion, 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.

    Vuori Founder Joe Kudla: From Garage Startup to $5Billion+ Activewear Brand

  4. Jul 7

    James Reinhart, Co-Founder & CEO of Thredup: Building the Future of Resale

    When James Reinhart walked into a Cambridge consignment store with a bag of business school clothes in 2008 – a J.Crew cashmere sweater, a Brooks Brothers coat – and was told they had no resale value, he didn't accept the answer. "I can't believe this cashmere sweater is worth zero," Reinhart tells Ken. That moment became Thredup. Sixteen years later, the company he co-founded as a broke ex-teacher earning $24K a year is a public marketplace approaching $400M in annual revenue, with 25M+ items sold this year across 35,000 brands. In this episode of The Retail Pilot, Ken sits down with James Reinhart – Co-Founder and CEO of Thredup – to unpack how a former 8th grade teacher built one of the most operationally complex companies in fashion. They explore the founding story, the "Netflix of shirts" pitch, the unit economics driving 80% gross margins, the Resale-as-a-Service partnerships with J.Crew, Athleta, Steve Madden, and Cotopaxi, the peer-to-peer launch competing with Poshmark and Depop, and the 4-day work week that became permanent. In this episode you'll learn: How a Cambridge consignment rejection and a J.Crew cashmere sweater became the genesis of ThredupWhy the first year ran on $70K with 7 employees – and why Boston VCs passed before Silicon Valley said yesThe "Netflix of shirts" original pitch – and why it was a "terrible business" that taught them everythingHow Thredup hit ~$400M in annual revenue and a 25% YoY increase in active buyersThe KPIs James actually tracks: contribution margins, LTV to CAC, and units per hour throughputThe supply-side strategy: why dominating sellers is the playbook (and what Airbnb, OpenTable, and Spotify taught him)Resale-as-a-Service: how J.Crew, Athleta, Steve Madden, and Cotopaxi power resale with ThredupThe direct listings launch: how Thredup is competing with Poshmark and DepopInside Thredup's distribution centers: hundreds of thousands of items processed daily, 1M+ photos a dayThe Dallas warehouse: 4 football fields, 4 stories high, 10M items, $600–700M in throughputHow AI is powering search, discovery, and Pinterest-board-to-shop curationThe 4-day work week experiment that never ended – and the sabbatical and maker day policies before itWhy Thredup went public – and why James thinks it made the company "so much better"This episode is for you if: you're a founder building operational moats, a retail operator exploring Resale-as-a-Service, an investor tracking unit economics, a brand leader weighing circularity, or an HR leader curious about the 4-day work week. Subscribe to The Retail Pilot for more conversations with retail leaders shaping the future of commerce. If you missed our last episode, where Denise Incandela unpacks Walmart's fashion transformation, 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.

    James Reinhart, Co-Founder & CEO of Thredup: Building the Future of Resale

  5. Jun 23

    Denise Incandela, EVP of Walmart Fashion: How Walmart Became a True Fashion Destination

    Walmart just named Denise Incandela a Sam Walton Entrepreneur of the Year — one of the highest honors inside the company, and one rarely given to merchants. It's a fitting recognition for the EVP of Fashion leading one of the largest fashion transformations in American retail. In this episode of The Retail Pilot, Ken sits down with Denise Incandela -- EVP of Fashion at Walmart U.S. and a 20-year luxury retail veteran (Saks Fifth Avenue, Ralph Lauren) -- to unpack the three pillars driving Walmart's strategy: assortment, shopping experience, and perception. They explore the 80% insight that reshaped everything, how Denise's team modernized 15 private brands while bringing in 1,000+ national brands, why Walmart pop-ups in Soho became a viral cultural moment, how AI is collapsing the design-to-shelf cycle from nine months to under one, and why the $100K+ customer is now the growth engine. This is a conversation about scale, democratization, and changing how an entire country thinks about Walmart fashion. In this episode you'll learn: Why Denise won the Sam Walton Entrepreneur of the Year Award -- and why merchants almost never receive it The three pillars of Walmart's fashion transformation: assortment, shopping experience, and perception The 80% insight that changed everything: Walmart's customer spend was happening at higher price points than it offered The private brand playbook: six $1B+ brands, four $2B+ brands, and the New York design team behind them How Free Assembly, Scoop, Joy Spun, and Weekend Academy were built -- and why some legacy brands had to be sunset The Soho pop-up that did 40% more daily volume than an average Supercenter with just three brands Cashmere for $45 and silk for the first time in Walmart's history — and what sold out almost immediately Why Walmart is "very different than fast fashion" -- and how quality sets the guardrails The Zeekit acquisition and virtual try-on driving higher conversion and lower return rates The creator strategy changing perception faster than any traditional media buy The $100K+ customer: where Walmart is winning her from, and why she's the growth engine Why "you had to shop at Walmart" is becoming "you want to shop at Walmart" 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 Tanya Golesic unpacks exactly how she's scaling Mackage beyond its outerwear roots, 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.

    Denise Incandela, EVP of Walmart Fashion: How Walmart Became a True Fashion Destination

  6. Jun 2

    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 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.

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

  7. May 19

    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 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.

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

  8. May 6

    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 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.

    Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup
See All (113)

4.6
out of 5
29 Ratings

About

The Retail Pilot is a series of interviews conducted by Ken Pilot with “Leaders and Legends” of the Retail industry. Ken will focus the conversation on his guests’ career journeys and their greatest career accomplishments and disappointments; gather insight into their leadership styles; learn who inspired them as they progressed through their careers; identify brands they admire; discover challenges they have faced; and talk about where they think Retail is headed and how they are leveraging technology to get there. Hosted on Ausha. See ausha.co/privacy-policy for more information.

Information

  • Creator
    Ken Pilot
  • Years Active
    2023 - 2026
  • Episodes
    113
  • Rating
    Explicit
  • Copyright
    © All rights reserved
  • Show Website
    The Retail Pilot

You Might Also Like