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.
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Données mises à jour le 09/09/2026
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Shea Jensen, President of Urban Outfitters North America: Inside the Brand's Comeback
mardi 18 août 2026 • Durée 50:01
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 Alpha
The BDG denim strategy: premium denim at a non-premium price, building fit franchises with staying power
How Out from Under became a lounge and athleisure powerhouse without trying to compete with Lululemon
The price elasticity playbook: covering opening, mid, and best price points to serve every customer
Urban's four store types: high-profile, community, college, and core doors
The fleet right-sizing story: going from oversized boxes to a 7,000–9,000 sq ft sweet spot
Why Reddit, Pinterest, connected TV, and TikTok are driving discovery, not Facebook or Instagram alone
The DoorDash partnership pulling customers in on Thursday and Friday afternoons
The Chipotle, Dunkin', and beverage collabs turning brand partnerships into cultural moments
The one piece of career advice Shea would give her younger store manager self
This 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.
Neil Saunders, Managing Director of GlobalData: Inside Retail's Winners, Losers & the Back Half of 2026
mardi 4 août 2026 • Durée 01:04:13
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"
Vuori Founder Joe Kudla: From Garage Startup to $5Billion+ Activewear Brand
mardi 21 juillet 2026 • Durée 58:28
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 of
Why raising money in 2013 was "almost impossible", and how $400K from friends and family got it started
How the first store became a community hub, art gallery, and office all at once
The REI break that proved premium men's athleisure could be a wholesale category
How Vuori hit profitability by 2017 with the office in the backstock room
The capital strategy most people misunderstand: $1.2B+ raised for shareholders, only ~$2M put on the balance sheet
The international growth story: from a beach town in Encinitas to customers in China and Korea
James Reinhart, Co-Founder & CEO of Thredup: Building the Future of Resale
mardi 7 juillet 2026 • Durée 56:24
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 Thredup
Why the first year ran on $70K with 7 employees – and why Boston VCs passed before Silicon Valley said yes
The "Netflix of shirts" original pitch – and why it was a "terrible business" that taught them everything
How Thredup hit ~$400M in annual revenue and a 25% YoY increase in active buyers
The KPIs James actually tracks: contribution margins, LTV to CAC, and units per hour throughput
The 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 Thredup
The direct listings launch: how Thredup is competing with Poshmark and Depop
Inside Thredup's distribution centers: hundreds of thousands of items processed daily, 1M+ photos a day
The Dallas warehouse: 4 football fields, 4 stories high, 10M items, $600–700M in throughput
How AI is powering search, discovery, and Pinterest-board-to-shop curation
The 4-day work week experiment that never ended – and the sabbatical and maker day policies before it
Denise Incandela, EVP of Walmart Fashion: How Walmart Became a True Fashion Destination
mardi 23 juin 2026 • Durée 46:34
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
Tanya Golesic, CEO of Mackage: From Canadian down to a Global Luxury Brand
mardi 2 juin 2026 • Durée 55:03
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
Pete Nordstrom: From public to private, Nordstrom’s gains momentum.
mardi 19 mai 2026 • Durée 45:55
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
Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup
mercredi 6 mai 2026 • Durée 01:09:41
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.
Rhone CEO Nate Checketts on Mind & Body Wellness: How Mental Fitness Built a $100M Performance Brand
mardi 14 avril 2026 • Durée 57:34
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
Guggenheim Analyst Simeon Siegel: Why Revenue Matters More Than Hype in Retail + 2026 Stock Picks
vendredi 13 mars 2026 • Durée 55:08
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
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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.
How Vuori handled the tariff hit: don't panic, never cut corners, and split the cost three ways
The 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.
Why 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.
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.
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.
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.
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.
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.
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.
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.
