Explore every episode of the podcast The Retail Pilot

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.

Connect with Ken:
-Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. 

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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.

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
• 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.

Connect with Ken:
-Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube.

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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
• 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.

Connect with Ken:
-Follow Ken Pilot Ventures on LinkedIn, Instagram, and YouTube. 

Hosted on Ausha. See ausha.co/privacy-policy for more information.

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.

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

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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In this episode of The Retail Pilot, we’re joined by Scott Friend, a longtime leader in the retail and venture capital world. A partner at Bain Capital Ventures and the co-founder of ProfitLogic, Scott shares his journey from operator to investor, his unique lens on early-stage startups, and what separates great founders from the rest. We unpack the evolution of BCV over the past 20 years, the power of founder-market fit, and why customer success is non-negotiable in today’s startup landscape.

Scott offers candid insights on investing in companies like Rent the Runway, Jet.com, Attentive, Miracle, and Archive, plus his take on AI's growing influence in commerce. From the one that got away (Peloton) to his thoughts on grit, momentum, and the founder’s mindset, this conversation is packed with value for entrepreneurs, investors, and anyone passionate about the future of commerce.

Key Topics Covered:

• Scott’s journey from building ProfitLogic to investing at Bain Capital Ventures

• What makes a founder stand out (and why most are first-timers)

• How BCV approaches early-stage vs. growth-stage investing

• Common characteristics of breakout founders like Jen Hyman and Marc Lore

• The importance of customer success and analytic rigor

• AI’s disruptive role in commerce platforms

• Why focus and momentum matter more than perfection

• Personal stories behind high-stakes risk and reward (including Jet.com)

• The investment that got away and the companies he’d double down on

• Rapid fire: Favorite show, CEO admiration, and meeting the Dalai Lama
  

If you enjoyed this episode, be sure to subscribe, leave a review, and share with your network. For more insights on the future of commerce and investing, follow The Retail Pilot wherever you get your podcasts.

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In this inspiring episode of The Retail Pilot, retail legend Jenny Ming shares her remarkable journey—from launching Old Navy at Gap Inc. to leading transformative growth at Rothy’s. Jenny reveals how she navigated career pivots, built billion-dollar brands, embraced fast fashion logistics, and stayed true to her values through every leadership chapter. This is a masterclass in visionary retail, thoughtful decision-making, and building businesses with purpose.

Whether you're an aspiring entrepreneur, retail exec, or brand builder, Jenny’s insights on creating iconic customer experiences, staying nimble, and leading through complexity will leave you inspired and energized.

Show Notes:

• Jenny shares the pivotal moment she was offered the opportunity to launch a new retail brand while planning a move to Hong Kong.

• How Old Navy went from “Gap Warehouse” to a standalone brand—and why other potential names like “Monorail” and “Forklift” thankfully didn’t make the cut.

• Her approach to launching with 50 stores from the start, and why thinking like an investor helped shape early decisions.

• The reality of working with a lean, scrappy team and the lessons she learned in intrapreneurship at Gap Inc.

• Why Old Navy's lighthearted brand tone and accessible price points resonated with families—and made fashion fun again.

• Transitioning into CEO roles after Gap, including a decade at Charlotte Russe and her bold comeback at Rothy’s.

• The importance of sustainability, style, and washability in Rothy’s brand DNA—and how Jenny helped the company return to profitability in months.

• How she’s expanded Rothy’s into Nordstrom, Bloomingdale’s, Anthropologie, and international markets while maintaining brand integrity.

• Her take on tariffs, supply chain diversification, and how early planning helped Rothy’s navigate disruption.

• Why testing, listening, and growing with your team are pillars of her leadership style.

• Jenny’s thoughts on the power of strategic collaborations, the future of retail tech, and what keeps her inspired as a mentor and coach.

• Plus: her leadership must-do’s, favorite cities, favorite brands, and what she looks for when hiring.
  
  Enjoy the episode? Be sure to subscribe, leave a review, and share it with someone who’s building something bold. Your support helps us bring more candid stories from retail’s top voices to your feed.

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In this episode of The Retail Pilot, host Ken Pilot welcomes Emily Gittins, Co-founder and CEO of Archive — a technology company transforming fashion's relationship with resale. With a deep background in mathematics, environmental science, and business, Emily takes us through her journey from Cambridge to BCG to Google X, and eventually to co-founding Archive with a bold vision: enable brands to profit from resale and reduce fashion waste at scale.

Emily unpacks how Archive partners with top brands like The North Face, Oscar de la Renta, and New Balance to integrate branded resale into their business models — creating new revenue streams while advancing sustainability. Discover how her team is changing industry perceptions, scaling globally, and pioneering circular solutions in new verticals like home goods and electronics.

Whether you're a fashion exec, sustainability advocate, or retail tech enthusiast, this episode offers a masterclass in turning purpose into profit.

Show Notes:

🔹 Guest Background

• Emily’s education: BA in Mathematics (Cambridge), MBA & MS in Environmental Science (Stanford)

• Past experience: BCG, Google X, international development work on gender equity and mobile tech
  

🔹 Key Topics Covered

• Why fashion is responsible for 8% of global greenhouse gas emissions

• The myth of resale cannibalizing full-price sales

• Archive’s unique tech platform for peer-to-peer resale, in-store trade-ins, and consignment

• Partnerships with brands like Lululemon, Doc Martens, and M.M.LaFleur

• The data-driven approach to pricing, SKU matching, and profit optimization in resale

• Scaling Archive internationally and expanding into new categories

• Raising $60M+ in funding and what’s next for the circular economy
  

🔹 Powerful Stats & Takeaways

• 100 billion clothing items are produced annually — enough to clothe the next 6 generations

• Resale customers have 2–3x higher lifetime value than new-only customers

• M.M.LaFleur saw a 3% revenue boost in year one from resale alone

• Resale is expected to become a $350B market
  

🎙️ Listen Now:
Available on Spotify, Apple Podcasts, and your favorite streaming platforms.

Learn More About Archive:
https://www.archiveresale.com

Sponsored by Firework

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In this episode of The Retail Pilot, we sit down with Amanda Baldwin, the newly appointed CEO of Olaplex and former CEO of Supergoop, for an in-depth conversation about her remarkable career journey—from Wall Street to the heart of the beauty industry. Amanda shares how her early curiosity about brands evolved into a passion for consumer-driven storytelling, innovation, and leadership in some of the world’s most iconic beauty companies.

We explore her pivotal career moments, including her transition from finance to beauty, the foundational experiences she gained at Estée Lauder and LVMH, and how she scaled Supergoop from a small team to a category-defining brand. Now at the helm of Olaplex, Amanda outlines her vision for rebuilding brand strength, deepening pro community relationships, and driving innovation through groundbreaking R&D.

This episode offers a masterclass in brand leadership, navigating industry change, and staying grounded in purpose while scaling globally.

If you enjoyed this conversation, be sure to like, follow, and leave a review—it helps us reach more listeners and continue bringing you these powerful insights.

Show Notes:

• Amanda’s early curiosity about consumer brands and storytelling

• Lessons learned from Wall Street, Estée Lauder, and LVMH

• The early growth story of Supergoop and how innovation drove scale

• Why product quality and emotional connection are non-negotiable for brand longevity

• Olaplex’s patented technology, salon-first strategy, and Amanda’s plans to reinvigorate the brand

• Investing in team, infrastructure, and culture as part of operational excellence

• Navigating the public markets while staying focused on long-term brand value

• Advice for early-career professionals and the role of mentorship in her success

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A few weeks ago, I wrote an open letter to President Trump urging him to reverse the extreme tariffs and embargoes imposed on China. These policies have had a significant impact on the apparel, footwear, and toy industries—industries that have long operated offshore due to cost efficiencies and global supply chains. The response was overwhelming: over 800 reactions, 70,000 views, and 50+ reposts on LinkedIn, reflecting broad concern across the industry.

However, the post also sparked a thoughtful and passionate response from a former colleague who sees a different path forward—one that includes a revival of U.S.-based manufacturing.

In this episode of The Retail Pilot, we sit down for a grounded, no-holds-barred conversation about tariffs, trade, and the real-world ripple effects on American business.

Joining me are:

• Adrian Miramontes, COO/CFO of Boston Proper, a women’s apparel brand that manufactures 80%+ of its product in China and now faces existential risk due to tariff-related cost increases.

  
  

• Jan Rogers Kniffen, CEO of J Rogers Kniffen Worldwide and longtime retail executive and CNBC contributor, who shares sobering insights on the long-term hollowing out of U.S. manufacturing.

  
  

• Bear Clark, Chief Innovation Instigator at Ear Micro and a pioneer in the hearables industry, who once ran a thriving U.S.-based manufacturing company—until Chinese subsidies and trade shifts changed everything.

  
  

Together, we explore both sides of the issue—from the hopeful possibilities of automation and fair trade to the painful reality many small-to-mid-sized retailers now face. Whether you're a policymaker, entrepreneur, or consumer, this episode will challenge how you think about global sourcing, pricing, and the future of U.S. industry.

You’ll Learn:

• Why my call to reverse tariffs gained massive traction—and pushback

• How Chinese subsidies disrupted entire U.S. industries, one bid at a time

• Why companies like Boston Proper depend on Chinese manufacturing

• What domestic production could look like in the age of automation and AI

• Why rushed trade policy reform could do more harm than good without a plan

• The moral and economic case for reciprocal trade and environmental accountability

Topics Covered:

• The decline of American manufacturing over six decades

• Fast fashion, fair labor, and environmental implications

• Tariffs as economic tools: punishment, leverage, or necessity?

• What a balanced and effective trade strategy might actually look like
  

  
  

Final Thoughts:
We may not all agree on the solution, but this conversation marks a critical starting point: how can the U.S. support fair, strategic trade that benefits workers, business owners, and consumers alike—without trading stability for short-term politics?

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In this episode of The Retail Pilot, host Ken Pilot sits down with Daniella Vitale, CEO of Ferragamo and one of the most influential leaders in luxury retail. From wrapping gifts at a small shop in New Jersey to leading some of the biggest names in fashion — including Armani, Gucci, Barneys New York, Tiffany & Co., and now Ferragamo — Daniella shares her remarkable career journey, pivotal leadership lessons, and deep passion for product innovation.

Daniella opens up about navigating the digital transformation of legacy brands, scaling Ferragamo’s digital business, and why authentic customer experiences are the future of luxury. She also discusses her philosophy on leadership, career advice for the next generation, and how Ferragamo is evolving its women's business to drive growth in a challenging global market.

Whether you're an aspiring fashion executive, a retail enthusiast, or a brand leader navigating change, Daniella’s insights will leave you inspired, informed, and ready to take bold chances.

Show Notes:

• Introduction to Daniella Vitale’s career in luxury retail, including her leadership roles at Armani, Gucci, Barneys New York, Tiffany & Co., and Ferragamo

• How wrapping gifts as a teenager sparked her lifelong passion for retail

• The importance of embracing both product and operations to become a successful CEO

• Daniella’s experience launching digital at Gucci and transforming Barneys' online business

• Lessons learned from leading Barneys through financial challenges and innovation

• Driving Ferragamo’s digital growth and building an omnichannel strategy

• How Ferragamo is shifting from a men's shoe powerhouse to a women's leather goods leader

• The critical role of customer experiences, lifestyle branding, and storytelling in luxury today

• Insight into the evolving challenges in the luxury retail market — from tariffs to changing consumer behaviors

• Daniella’s leadership approach: building cohesive, collaborative, and empathetic teams

• Advice for young professionals entering the retail and fashion industries

• Rapid-fire questions: favorite brands, dream city to live in, favorite shows, and who she’d love to meet
  

  If you found value in this episode, don’t forget to share it with your network and help us spread these inspiring lessons across the industry!
  

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In this episode of The Retail Pilot, host Ken Pilot welcomes PJ Oleksak, the dynamic CEO of Nuts.com and the first woman and non-family member to lead the 94-year-old business.

With a rich background that includes leadership roles at FreshDirect and Slice, PJ shares how she combines a deep understanding of finance with a passion for food to lead transformative change in legacy brands. She walks us through her journey from private equity to pioneering online grocery, her leadership philosophy, and how she’s steering Nuts.com toward omnichannel growth.

PJ also discusses the challenges and opportunities in modernizing a family-owned business—building a performance-driven culture, embracing AI and tech innovation, and preparing to launch a sister retail brand. Whether you're in e-commerce, food retail, or scaling a family business, this episode offers practical wisdom on navigating growth while staying true to your roots.

Show Notes:

• Guest: PJ Oleksak, CEO of Nuts.com

• Background: Former Chief Growth Officer at FreshDirect and Chief Business Officer at Slice

• Topics Covered:

  • PJ’s transition from private equity to food tech

  • Lessons learned from FreshDirect and Slice

  • Modernizing a 94-year-old business and earning trust as an outsider

  • Building high-performing, happy teams and instilling accountability

  • The cultural and operational shifts at Nuts.com under her leadership

  • Strategic moves toward omnichannel growth and retail distribution

  • The impact of AI across departments, from sales to creative

  • How Nuts.com is adapting to rising cocoa costs and sourcing challenges

  • Leadership philosophy and importance of founder-CEO alignment

  • Looking ahead: launching a sister brand and expanding customer reach

• Key Insight: Balancing legacy with innovation requires empathy, structure, and a relentless focus on the customer experience.

Sponsored by Firework

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In this episode of The Retail Pilot, host Ken Pilot dives into the future of branding and retail innovation with Emily Heyward & JB Osborne, Co-Founders of Red Antler and a pre-flight discussion with retail futurist Jan Kniffen.

From the transformative role of AI in customer experience to the secret sauce behind some of today’s most iconic brands, this conversation explores how emotional resonance, creativity, and technology intersect in modern retail. Ken, Emily, and JB also discuss brand building from scratch, the challenges of rebranding, and their venture fund Habitat Partners. Plus, they reflect on favorite campaigns, dream brand revivals, and the evolving landscape of consumer expectations.

Show Notes

• Ken Pilot introduces the episode with commentary from retail expert Jan Kniffen on the seismic impact of AI across industries, especially in retail.

• Jan shares why AI will redefine omnichannel experiences and customer expectations, emphasizing the urgency for retailers to invest or fall behind.

• Emily Hayward and JB Osborne join Ken to discuss Red Antler’s approach to branding, which centers on empathy, storytelling, and strategic creativity.

• Insights into how Red Antler partners with early-stage founders and legacy businesses, building emotional connections through meaningful brand positioning.

• Reflections on helping launch brands like Allbirds, Casper, Burrow, and Hinge, including the challenges and rewards of naming and storytelling.

• Candid thoughts on the rise and stumbles of DTC pioneers and how capital structure, not branding, often drives downfall.

• A look at Habitat Partners, their investment arm, and why equity plays helped foster long-term alignment with founders.

• Exploration of how AI is impacting creative workflows, campaign ideation, and brand communication.

• Rapid fire favorites, from travel destinations to go-to coffee brands, and the dream jobs Emily and JB would pursue outside of Red Antler.

• Plus, JB and Emily name the brands they’d love to reimagine—from OpenTable to LinkedIn—and share their vision for brand leadership in a tech-driven era.

This episode is sponsored by Firework.

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In this inspiring episode of The Retail Pilot: Leaders & Legends, host Ken Pilot sits down with EGOT-winning artist and entrepreneur John Legend, alongside brand builder Ari Bloom, co-founder and CEO of A-Frame Brands. Together, they unpack the story behind their inclusive skincare line Loved01—a brand created with intention, affordability, and care for melanin-rich and sensitive skin.

John shares how his dual passion for music and academics shaped his career, why love is the foundation of everything he creates, and what it’s like building a brand with his longtime stylistic and creative team. Ari details the strategy behind launching socially conscious brands through A-Frame, lessons from live selling on QVC and Amazon, and how the data is shaping their next moves.

👉 Promo Code: Get 25% off your next Loved01 purchase at Loved01.com with code PILOT25 — valid through May 1.

📌 Chapters & Highlights:.

• John’s Early Career Path
  From piano lessons at 4 to BCG consultant by day and musician by night—how John balanced brains and creativity.

• The Origin of A-Frame & Loved01
  Ari shares how A-Frame Brands came to life and why teaming up with John was a natural fit.

• Why the Name “Loved01”
  The personal meaning behind the brand name and how it reflects self-care and connection.

• Filling the Skincare Gap
  Designing products for melanin-rich and aging skin—without celebrity price tags.

• Formulation & Sourcing Strategy
  How Loved01 created high-quality, plant-based products domestically with no compromises.

• Chrissy Teigen’s Favorite Products
  What John’s wife loves about the brand—and why their $15 exfoliator beats high-end competitors.

• Retail Approach & Affordability
  The importance of being accessible—through retailers like CVS, Amazon, and QVC.

• The Power of Live Selling
  Why QVC, CBS, and Amazon are outperforming traditional ad spend—and how John’s charisma shines through.

• Using Data to Drive Growth
  How real-time feedback helps the team pivot, learn, and win with the right audiences.

• Expanding the Brand & What’s Next
  New products, fragrance updates, B2B partnerships, and opportunities in hospitality.

• Rapid Fire Fun
  John shares his favorite clothing brands, travel destination, dream meeting, and more.

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On this episode of The Retail Pilot, host Ken Pilot welcomes the visionary designer and founder, Jonathan Adler. Known for his signature blend of chic sophistication and playful wit, Jonathan shares his incredible journey from an aspiring potter to building a global design empire. From his early days spinning clay at summer camp to landing his first collection at Barney’s and expanding into furniture, lighting, and decor—this episode is packed with insights on resilience, creativity, and building a timeless brand.

Jonathan also speaks into the intersection of business and design, the importance of humor in his work, his collaboration with Consortium, and his vision for the future of retail. Plus, hear about his relationship with husband Simon Doonan, the lessons he's learned over 30+ years in business, and why he believes in the power of "more."

Key Takeaways:

🔹 How Jonathan Adler transformed his passion for pottery into a global lifestyle brand
🔹 The importance of humor and storytelling in design
🔹 The business lessons he learned the hard way (including forgetting to send his first invoice!)
🔹 Why he believes in the power of “more” when it comes to brand expansion
🔹 His favorite sources of inspiration, from Slim Aarons to travel destinations

💡 Enjoyed the episode? Leave us a review on your favorite podcast platform!

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In this episode of The Retail Pilot, host Ken Pilot kicks off with a PreFlight segment featuring retail expert Jan Kniffen. They dive into the ever-changing sneaker market, discussing Nike’s comeback, the rise of On Running and Hoka, and how brands like Skechers and New Balance are shaking up the industry.

Following PreFlight, Ken welcomes special guest Sarah LaFleur, Founder and CEO of M.M.LaFleur, for an insightful conversation about how she built a brand that redefined workwear for women. From launching the company in 2013 to navigating the challenges of COVID and financial setbacks, Sarah shares her journey of resilience, innovation, and customer-driven design.

Learn how M.M.LaFleur’s mission to simplify dressing for professional women has evolved, how Sarah leveraged trunk shows and word-of-mouth marketing to scale the brand, and why she believes adaptability is key to entrepreneurial success. Plus, she shares insights on the future of retail, the role of AI in fashion, and her vision for M.M.LaFleur in the next decade.

Key Takeaways:

✈️ PreFlight with Jan Kniffen:
🔹 The rise of smaller sneaker brands and how they’re impacting Nike & Adidas
🔹 Why Nike is poised for a strong comeback in 2025-2026
🔹 How the running shoe market is evolving and what it means for retailers

🛫 Main Interview with Sarah LaFleur:
🔹 The inspiration behind M.M.LaFleur and how it started
🔹 How Sarah built a brand focused on function, fashion, and ease
🔹 The impact of COVID on retail and how M.M.LaFleur pivoted
🔹 Raising capital and overcoming financial hurdles in record time
🔹 The future of retail and the role of AI in fashion
🔹 The power of mentorship and community support

🎧 Listen Now on Your Favorite Podcast Platform!
Don’t forget to leave us a review and share this episode.

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In this episode of The Retail Pilot, host Ken Pilot interviews Dana Telsey, CEO and Chief Research Officer of Telsey Advisory Group. They explore key trends shaping the future of retail, including AI-driven personalization, shifting consumer behaviors, and the evolution of store formats. Dana shares insights on top-performing brands like Birkenstock, Warby Parker, and Abercrombie & Fitch, along with the challenges facing luxury retail and department stores. The discussion also covers tariffs, global supply chain shifts, and the increasing role of social media in retail strategy.

Key Topics Discussed

• Dana Telsey’s Career Journey – Her experience in equity research, investment banking, and retail strategy

• Retail Trends for 2025 – Personalization, curation, and the growing role of AI in retail

• Top Companies to Watch – Birkenstock, Warby Parker, Walmart, Abercrombie & Fitch, and Lululemon

• Luxury Retail & Department Stores – The Saks-Neiman Marcus merger and the shift toward direct-to-consumer strategies

• The Impact of AI in Retail – Enhancing personalization, content creation, and supply chain management

• Social Media & Retail – The influence of TikTok and social commerce on brand visibility

• The Evolution of Physical Retail – The rise of pop-up shops, smaller store formats, and experiential retail

• Tariffs & Global Production – How supply chain shifts and economic uncertainty affect pricing

• Nike & Sneaker Market Competition – Challenges from rising brands like Hoka, On Running, and Skechers

• Retail Technology & Customer Experience – AI-powered POS, RFID, and real-time analytics in retail
  
  

Highlights & Key Takeaways

• AI & Personalization – Retailers are investing in AI to refine customer experiences and optimize operations

• Success of Top Brands – Birkenstock’s full-price strategy, Warby Parker’s store model, and Abercrombie’s resurgence

• Luxury Retail Shifts – Direct-to-consumer is becoming the primary focus for major luxury brands

• Retail Media Networks – Gaining traction but still proving their impact on sales and customer engagement

• Power of Social Media – TikTok has become a critical platform for understanding emerging consumer trends

• Tariffs & Rising Costs – Retailers are diversifying supply chains to reduce dependency on China

• In-Store Experience Matters – Brands like Skims and RH are leveraging immersive retail environments

• Nike’s Competitive Pressure – Facing challenges from new brands, Nike must redefine its market strategy

• Retail’s Need for Agility – The most successful brands are those that adapt quickly to changing consumer demands

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Ken Pilot interviews Emily Current and Meritt Elliott, Co-Founders of fashion brand, The Great, on this Flight of The Retail Pilot Podcast. Plus, he has a short "Pre-Flight" conversation with Jan Kniffen, former retail executive and current CNBC retail expert, to discuss what 2025 looks like for the retail industry.

Pre-Flight with Jan Kniffen

Jan Kniffen shares his outlook for retail in 2025:

• Retailers are optimistic after a solid 2024 holiday season

• Consumer spending expected to remain healthy, especially among higher-income shoppers

• Lower-income consumers adapting to higher costs

• Tariffs not a major concern for most retailers

• Positive outlook for discretionary retailers like Ralph Lauren, Nike, Lululemon

Interview with Emily Current and Meritt Elliott

Ken speaks with the co-founders of The Great about their journey and brand:

Brand Origins

• Met as UCLA students, bonded over vintage fashion

• Started as celebrity stylists before launching denim brand Current/Elliott

• Founded The Great in 2015, focusing on casual, nostalgic Americana

  
  

The Great Brand

• Offers casual, vintage-inspired clothing across multiple categories

• About $50 million in annual revenue

• Distribution split between e-commerce, retail stores, and wholesale

  
  

Business Approach

• Self-funded, focused on organic growth

• Value wholesale partnerships alongside direct-to-consumer

• Emphasis on in-person experiences and community building

  
  

Collaborations

• Partnerships with Eddie Bauer, Birkenstock, Pottery Barn

• Interested in future collaboration with Converse

  
  

Marketing Strategy

• Rely heavily on word-of-mouth and organic growth

• Use collaborations and retail stores as marketing tools

• Celebrity fans include Reese Witherspoon and Rachel Bilson

  
  

Future Plans

• Expanding reach to new geographic markets

• Considering growth in men's, children's, and home categories

  
  

Working as Co-CEOs

• Emphasize complementary skills and shared vision

• Stress importance of understanding all aspects of the business

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In this episode of The Retail Pilot, host Ken Pilot sits down with Alex and Mike Faherty, co-founders of Faherty Brand, to discuss their business journey, recent successes, and future plans.

Key Topics Discussed:

• Faherty's performance during Black Friday and Cyber Monday 2024

• The brand's growth trajectory and end-of-year projections

• Expansion of retail stores and focus on in-store experiences

• Product development and bestselling items

• Marketing strategies and collaborations

• Tech innovations and simplification efforts

• Team building and company culture

• Preparing for potential tariff changes in 2025

• Exciting plans and collaborations for 2025

Highlights:

• Faherty now operates 72 stores, with plans to open more in 2025

• The brand is doing "hundreds of millions" in revenue

• Focus on hero products like the Legend Shirt and Stretch Terry Pants

• Emphasis on creating a boutique feel while making shopping easier for customers

• Upcoming collaborations with a surf club in Ghana and big wave surfers in Portugal

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In this episode of The Retail Pilot, Ken Pilot welcomes back Stephen Yalof, President and CEO of Tanger, Inc.

With over 25 years of experience in the commercial real estate industry, Stephen shares insights into Tanger's growth strategies, the evolution of retail spaces, and how the company is adapting to changing consumer behaviors. From expanding into full-price lifestyle centers to enhancing customer experiences through digital innovation and loyalty programs, Stephen provides a comprehensive look at Tanger's journey and future direction.

Key Topics Discussed

1. Tanger’s Recent Successes Performance Highlights: Tanger achieved a 4.3% increase in net operating income (NOI) and a 97.4% occupancy rate. The company executed 543 leases covering 2.6 million square feet over the past year. Expansion Efforts: Recent acquisitions include The Promenade at Chenal in Little Rock, Arkansas, which features the only Apple Store in the state.

2. Growth Strategy Diversification: While maintaining its core outlet business, Tanger is expanding into full-price open-air lifestyle centers that include specialty stores, grocery anchors, and other amenities. Acquisition Focus: Stephen emphasized the importance of acquiring high-quality properties in strategic markets to leverage existing regional management teams.

3. Enhancing Customer Experience Tanger Club Loyalty Program: A tiered membership program offering discounts and perks for shoppers. Members can choose between free or paid memberships ($20 annually) for additional benefits. Digital Integration: Introduction of QR codes for real-time offers and digital savings passports, replacing outdated coupon books. Amenities and Entertainment: Investments in food offerings, gathering spaces, and entertainment options like pickleball courts to create a more engaging shopping experience.

4. Industry Trends Blending Physical and Digital Retail: Tanger is exploring e-commerce integration as part of its long-term strategy while using digital tools to enhance in-store experiences. Health & Beauty Brands: Increased presence of brands like Sephora and Ulta in outlet environments, offering regular-priced products alongside experiential services.

5. Leadership and Team Building Talent Development: Stephen emphasizes hiring complementary skill sets to address organizational blind spots and promoting from within to keep employees motivated. Communication Practices: Regular town halls, employee resource groups (ERGs), and an intranet ensure transparency and engagement across the organization.

6. Reflections on Leadership Lessons Learned: Stephen highlights the importance of "failing fast" to pivot quickly when strategies don’t work. He also stresses the value of building a strong team aligned with company goals.

Notable Quotes "Fail fast—if something doesn’t work, pivot quickly and move on." – Stephen Yalof "We’re lifestyle-izing our portfolio by adding food, beverage, amenities, and entertainment to enhance the customer experience." – Stephen Yalof "Our loyalty program is about understanding our customers better and providing them with personalized value." – Stephen Yalof

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Rent the Runway 2.0 - Redefining the Future of Fashion with Jennifer Hyman

Jennifer Hyman, co-founder and CEO of Rent the Runway, joins Ken Pilot to discuss the company's journey over the past 15 years.

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, a company that is disrupting the trillion-dollar fashion industry with the world’s first and largest shared designer closet. She has led the company for 15 years through all stages of growth, from inception in 2009 to a scale of more than 3M lifetime customers. Jennifer took the company public in 2021, making her the first woman ever to IPO a company with an all-female executive suite and the 30th woman ever to IPO a company. She has been honored on the TIME Top 100 Most Influential People List and the CNBC Disruptor List for 5 out of 10 years. She also serves on the Board of Directors of The Estée Lauder Companies and Zalando.

Rent the Runway's Origins and Growth

• Hyman pitched the concept to Diane von Furstenberg 48 hours after having the idea

• The company now rents about $5 billion worth of designer clothing annually

• Rent the Runway works with over 1,000 designers and has had 100% brand retention over 15 years

Business Model and Profitability

• The company has focused on becoming capital-light, with revenue sharing agreements with brands.

• Rent the Runway has more than doubled its margins over the last few years.

• The goal is to reach free cash flow breakeven.

Challenges and Resilience

• COVID-19 presented significant challenges for the business.

• Hyman emphasizes the importance of resilience and staying in the game.

Marketing and Customer Acquisition

• The company is refocusing on top-of-funnel marketing activities.

• Rent the Runway is leveraging its community and introducing new initiatives like the "Icons" program.

  
  

Physical Retail and Partnerships

• Hyman expresses interest in partnerships with retailers like Sephora, Ulta, or Zara.

• Previous partnerships with Neiman Marcus drove significant foot traffic.

Industry Insights

• Hyman discusses the disruption in the fashion industry, particularly from companies like Shein and Amazon.

• She notes the changing perception of brand value among consumers. T

• echnology and AI Rent the Runway is exploring AI applications in various areas, including photography, customer service, and search algorithms.

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In this episode of The Retail Pilot, host Ken Pilot sits down first in a Pre-Flight conversation with Simeon Siegel, Senior Retail Analyst for BMO Capital Markets, to discuss the state of the Retail market both post-election and leading into the holiday season.

For the main Flight, Ken speaks with Rachelle Hruska MacPherson, founder of the fashion brand Lingua Franca. Rachelle shares the unexpected journey that led her to create a company known for its hand-embroidered cashmere sweaters and socially conscious messaging.

Origins of Lingua Franca

• Rachelle started the company unexpectedly in 2016 while dealing with stress from her previous business
• The idea came from embroidering "booyah" on an old sweater as a therapeutic exercise
• Early success came from a viral "I Miss Barack" sweater after the 2016 election

Business Growth and Model

• Lingua Franca offers custom embroidery on cashmere and cotton items
• The company has expanded into ready-to-wear clothing and collaborations
• Current revenue is under $30 million, with 60-70% from direct-to-consumer sales

Product and Pricing

• Cashmere sweaters with embroidery retail for around $380
• Cotton items start at $150, opening up a new market segment
• Custom embroidery is available in stores and through an online customizer

Marketing and Collaborations

• Growth has been largely organic, with minimal traditional marketing
• Collaborations with celebrities, artists, and brands have been key to expansion
• Upcoming collaborations include Wicked and Gilmore Girls

Challenges and Future Plans

• Rachelle discusses the difficulties of scaling while maintaining brand authenticity
• She emphasizes the importance of product quality and customer service
• The company is exploring new marketing strategies, including digital advertising

Personal Insights

• Rachelle shares her favorite travel destinations and TV shows
• She discusses the importance of mentorship and community in the fashion industry

The episode provides an in-depth look at how Lingua Franca has grown from a personal project into a socially conscious fashion brand, navigating the challenges of scaling while maintaining its core values and unique positioning in the market.

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In this episode of The Retail Pilot, host Ken Pilot welcomes Jan Rogers Kniffen, CEO of J Rogers Kniffen Worldwide and retail industry expert, to discuss the current state and future of retail. Key Topics Discussed: Post-Election Retail Bounce

• Jan predicts a post-election retail bounce, as seen in previous presidential election years
• Discretionary retail is currently running at zero inflation, making it attractive to consumers

Fourth Quarter Outlook

• Despite potential headwinds, Jan expects a strong fourth quarter
• Forecasts 3.5-4% sales growth, similar to last year
• Believes discretionary goods will perform well due to their perceived value compared to inflating services

Walmart vs. Target

• Walmart is outperforming Target significantly
• Walmart is attracting higher-income customers, traditionally Target's demographic
• Walmart's focus on in-store experience and competitive pricing is paying off

Off-Price Retail Sector

• TJ Maxx ranked as the fifth-best retailer in America by Jan
• Concerns about over-saturation in the off-price sector
• Potential challenges for off-price retailers as the market matures

Department Store Future

• Predicts most department stores will go private by the end of 2026
• Cites lower interest rates and increased real estate values as factors facilitating buyouts
• Mentions Nordstrom, Macy's, and Kohl's as potential candidates for privatization

Tariffs and Manufacturing

• Discussion on the impact of potential tariffs, especially on goods from China
• Many retailers have already reduced their exposure to Chinese manufacturing
• Predicts that moderate tariff increases might be absorbed by Chinese manufacturers rather than passed on to consumers

Notable Quotes:

"May the bounce be with you." - Jan Rogers Kniffen on the post-election retail bounce

"I think it's come down to who can do this stuff as opposed to where you happen to be." - Jan Rogers Kniffen on retail performance

Closing Thoughts:

Jan expresses optimism for the retail sector going into the fourth quarter and 2025, despite potential challenges. He emphasizes the importance of execution and adaptation in the evolving retail landscape.

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On this episode of The Retail Pilot podcast, Ken speaks with Nick Green, Co-Founder & CEO of Thrive Market, a membership-based online platform that makes healthy and sustainable living easy and affordable to all. Nick launched Thrive 10 years ago shortly after graduating from Harvard.

The business has also been recognized as a leader in regenerative agriculture, carbon-neutral shipping, and Zero Waste operations, and in 2020 became the nation’s largest grocer to receive B Corp Certification.

Outside of Thrive Market, Nick lives in Venice, CA with his wife, Carolina, and their three children.

Key Points

About Thrive Market: An online retailer offering natural and organic products at affordable prices through a membership model1

Mission: Making healthy and sustainable living easy, affordable, and accessible to all1

Business Model: $60 annual membership fee

• Curated assortment of natural and organic products
• AI-powered personalization
• Zero-waste fulfillment and carbon-neutral shipping

Company Stats

• Founded: 10 years ago
• Members: 1.5 million
• Annual Sales: Over half a billion dollars
• Profitability: Now profitable and cash flow positive1

Nick Green's Background

• Grew up in Minneapolis with a health-conscious mother
• Previously founded and sold an education company
• Met co-founder Gunnar, who grew up on a hippie commune

Business Strategy

• Product Mix: 90% third-party brands
• 10% Thrive Market branded products (generating 25% of sales)
• Private Label Strategy: Focus on filling gaps in the catalog rather than copying existing products1
• Margin Profile: Strong margins on both private label and third-party products
• Sustainability: Zero-waste fulfillment centers, carbon-neutral shipping

Marketing Strategy

• Referrals: 25% of new members come from existing member referrals
• Influencer Marketing: Unique approach to partnerships
• Digital Marketing: Leveraging technology for personalized experiences

Future Outlook

• Focus on expanding online presence rather than immediate brick-and-mortar plans
• Potential for future physical stores, but not a current priority
• Continued investment in AI and personalization technologies

Competitive Advantage

• Purpose-built for healthy living
• Membership model driving profitability and customer behavior
• Technology-first approach to e-commerce
• Strong focus on sustainability and ethical supply chains

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Ken Pilot interviews Oliver Chen for this flight of The Retail Pilot podcast.

Oliver Chen is a Managing Director and senior equity research analyst covering retail and luxury goods at TD Cowen.  His deep understanding of the consumer and his ability to forecast the latest trends and technological changes that will impact the retail space have set him apart from peers.

Prior to joining TD Cowen in 2014, he spent seven years at Citigroup, worked in the investment research division at UBS, in the global mergers and acquisitions/strategic planning group at PepsiCo International, and in JPMorgan’s consumer products/retail mergers and acquisitions group.

Oliver holds a bachelor of science degree from Georgetown University, an MBA from the Wharton School at the University of Pennsylvania, and is a CFA charterholder.

His passion for the sector began at the age of 12 when he began working with his parents at their retail business in Natchitoches, Louisiana.

Summary:

In this conversation, Oliver Chen discusses the current state of luxury retail and the beauty sector, highlighting the challenges and opportunities faced by brands. He emphasizes the importance of pricing strategies, the impact of digital transformation, and the need for brands to connect with younger consumers. The discussion also covers emerging trends in fragrance, the potential of the men's beauty market, and the role of AI in enhancing the retail experience.

Key Takeaways:

• Luxury retail is facing an inflection point with declining sales.
• China's economic factors are influencing luxury spending.
• LVMH's strong brand portfolio positions it well in the market.
• Hermes thrives due to its timeless luxury appeal.
• Luxury brands are increasingly focusing on direct-to-consumer sales.
• Ralph Lauren's success is attributed to its cultural relevance and value perception.
• Fragrance is a growing category with opportunities for premiumization.
• The men's beauty market is still developing but shows potential.
• TikTok is becoming a significant platform for beauty brands.
• AI is set to transform the retail experience through personalized search.

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Ken Pilot interviews Shai Eisenman, CEO and Founder of Bubble, on this episode of The Retail Pilot Podcast. Bubble Skincare is the first modern, affordable, science-backed skincare line formulated to clean, balance and hydrate young skin all for under $20. Today, the Bubble line consists of 20+ products that work together to create a complete routine from face cleansers to face masks. Bubble products are available on hellobubble.com, in over 16,000 retail locations across the US, Austrailia and the UK including Boots, Beauty Bay, CVS Walmart and Ulta stores.

Prior to starting Bubble in 2018, Eisenman started her B.A. at 15, and began her career in business at 16 years old. She lives in New York with her partner and two children. 

Key Points:

• Shai started Bubble after an early start in academics and entrepreneurship
• Bubble focuses on affordable, high-quality skincare products for younger consumers
• The company built a community of 4,600 Gen Z advisors before launching
• Bubble now has over 50,000 brand ambassadors who provide input on all decisions
• Products are priced affordably (around $15) but with prestige-level quality
• Initially launched D2C but quickly pivoted to retail partnerships
• Now available in 13,000 U.S. stores including Walmart, Ulta, CVS, and Amazon
• Recently expanded to the UK (Boots) and Australia (Priceline)

Business Strategy:

• Focused on margin dollars rather than margin percentage
• Found retail partnerships more profitable than D2C for their price point
• Invests in physical experiences and grassroots marketing over traditional advertising
• Collaborates with brands like Disney to reach new audiences
• Raised capital primarily from individuals and early-stage funds
• Aims to be profitable and not reliant on external funding

Community Engagement:

• Uses multiple platforms to communicate with brand ambassadors
• Offers gift cards and commissions to ambassadors
• Runs college campus programs with exclusive merchandise
• Involves community in product development, naming, and marketing decisions

Challenges and Growth:

• Adapting leadership style and operations as the company scales
• Expanding internationally while remaining an independent brand
• Balancing control over brand experience with benefits of retail partnerships

Leadership Insights:

• Values building a strong team and fostering community
• Relies on experienced advisors for guidance in different growth stages
• Emphasizes the importance of adapting to different business stages

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In this episode of the Retail Pilot Podcast, Ken Pilot engages with retail legend Mickey Drexler, discussing the current state of retail, pricing trends, and the importance of customer experience. Drexler shares insights from his journey at Alex Mill, emphasizing the significance of quality, team dynamics, and the evolving landscape of retail. The conversation also features Ali Dillon, the President of Alex Mill, Alex Drexler, Founder, and Creative Director, Somsack Sikhounmuong, who discuss their roles and the brand's vision, highlighting the importance of community and innovative marketing strategies.

Key Takeaways Include:

Recent Success: Alex Mill has experienced strong sales performance attributed to changes in merchandising and management.

Product Focus: Sweaters and denim are particularly successful categories for Alex Mill, with emphasis on fit and quality.

Retail Strategy: Alex Mill follows a "less is more" approach, focusing on smaller store sizes and selective expansion.

Marketing Channels: Instagram is a primary driver of brand awareness, with the company also exploring TikTok marketing.

Expansion Plans: Alex Mill is planning to open a new store in Rockefeller Center, aiming for an early November launch.

Customer Acquisition: Word-of-mouth marketing plays a crucial role in the brand's growth and recognition.

Product Diversity: Mickey emphasizes the importance of offering multiple color options for key items to create visual impact and customer appeal. Sustainability and reworking products can also create new opportunities.

Team Dynamics: A strong, diverse team is critical for successful product execution and business operations.

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Ken Pilot interviews Simeon Siegel, MD and Senior Analyst, Retail & eCommerce for BMO Capital Markets, for this Flight of The Retail Pilot Podcast

Overview: In this episode, leading retail analyst Simeon Siegel returns to discuss the current state of the retail sector, emphasizing the importance of execution in a challenging economic environment.

• Key Topics: Simeon's Role: Simeon explains his work as a retail analyst, helping investors understand which companies are performing well and which are struggling. He covers 20-30 companies and provides ratings such as outperform, underperform, and market perform.
• Current Retail Climate: The year has been progressively challenging for retail, with lingering effects from the pandemic. While some sectors are struggling, others are thriving, highlighting a divergence between winners and losers in the market.
• Luxury Market Trends: The luxury sector is experiencing pressure for the first time in years, with growth slowing from 8% to 4%. Despite this, some brands like Prada and Hermes continue to perform well.
• Execution Matters: The conversation emphasizes that execution is key in today's market. Companies that adapt and perform well are gaining market share, while larger, established brands face challenges.
• Consumer Health: Despite concerns about credit card debt and inflation, the U.S. consumer remains resilient. Retailers need to balance promotions and marketing to maintain brand value while driving sales.
• Technology Investments: As retailers navigate challenges, there is a focus on investing in technology that enhances both online and in-store experiences. The importance of inventory management and customer engagement is highlighted.
• Winners in Retail: Companies like TJX are noted for their strong performance due to their unique value propositions for both consumers and vendors. Other brands showing potential include Nike, despite recent struggles.

Conclusion: The episode wraps up with reflections on the evolving retail landscape, emphasizing the need for brands to adapt strategically to maintain relevance and profitability amidst changing consumer behaviors and economic conditions.

Listen for More: Tune in for deeper insights into retail trends and expert analysis from Simeon Siegel!

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In this episode of The Retail Pilot - Tech Talk, Ken Pilot speaks with Vic Drabicky and Josh Krepon about performance marketing in the Retail/Fashion Industry.

Summary

In this conversation, Vic Drabicky, CEO and founder of January Digital, and Josh Krepon, President of US D2C and Global Digital at Steve Madden, discuss the current state of performance marketing and the importance of balancing algorithmic marketing with inspirational and influential marketing. They also touch on the challenges of creating and managing content, the role of video in marketing, and the rise of TikTok shops. The conversation covers various topics related to retail and marketing, including the impact of consumer behavior shifts, the role of video commerce, the importance of collaborations and influencers, the use of MarTech in loyalty and data management, and the potential impact of the election on the retail environment.

Key Takeaways

• Performance marketing has dominated the marketing landscape in the past decade, but brands now need to find a balance between algorithmic marketing and inspirational/influential marketing.
• Creating and managing content can be challenging, and brands need to strike a balance between volume and quality.
• Video marketing is becoming increasingly important, and brands need to adapt to the changing landscape of platforms like TikTok.
• The rise of TikTok shops and partnerships with platforms like Amazon indicate that video commerce is on the horizon. Consumer behavior takes time to shift, and it may not always align with predictions or trends.
• Video commerce is a growing trend, but it may take a long time for people to change their behaviors and adopt it on a large scale.
• Collaborations and partnerships with influencers or other brands can be successful if they are authentic, aligned with the brand's values, and provide value to the customers.
• MarTech tools can be used for retention and loyalty programs, as well as data management and analysis.
• The outcome of the election can impact the retail environment, with consistency and confidence being important factors for stability and growth.

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Ken Pilot interviews Mike Natenshon, Founder of Marine Layer, for this episode of The Retail Pilot Podcast.

Mike Natenshon started Marine Layer the day after his girlfriend threw away his favorite shirt. In the ensuing 10 years, Marine Layer has grown into a complete California-inspired lifestyle brand delivering new favorite shirts to wherever their customers are. Although considered 'digital first' Marine Layer operates 50 stores and two 1969 VW buses nationwide.

Summary

MarineLayer is a retail brand that started as an online t-shirt company and later expanded to brick-and-mortar stores. The company focuses on creating high-quality, comfortable clothing for men and women. They have a balanced distribution model, with 60% of sales coming from retail stores, 40% from direct-to-consumer online sales, and a small percentage from wholesale.

MarineLayer has been able to maintain profitability and grow steadily by taking a measured approach to expansion and focusing on building a strong brand. They have plans to continue growing all three distribution channels and are considering international expansion in the future.

Marine Layer is a brand that focuses on creating comfortable and casual clothing for both men and women. The stores are designed to feel like a room in your home, with a familiar and intimate atmosphere.

The company has a program called Respun, which is an upcycling initiative that collects old t-shirts and finds new uses for them. They offer customers a recycling bag and a credit towards future purchases.

In terms of marketing, Marine Layer uses paid social media advertising on platforms like Instagram and TikTok, as well as catalogs. They have also explored connected TV advertising but found it to be expensive and not as targeted as other channels.

In terms of technology, Marine Layer has invested in Endless Isle, which allows them to share inventory across channels and provide a seamless customer experience. They are also exploring the use of AI for customer analytics and predictive product merchandising.

As a leader, Mike is focused on protecting the company's culture and maintaining a fun and collaborative work environment. Marine Layer operates on a hybrid work model, with employees working three days in the office and two days remotely. Mike's favorite Marine Layer item is a t-shirt that he has worn for the births of both of his daughters.

Takeaways

• MarineLayer started as an online t-shirt company and later expanded to brick-and-mortar stores.
• They have a balanced distribution model, with 60% of sales from retail stores, 40% from online sales, and a small percentage from wholesale.
• The company focuses on creating high-quality, comfortable clothing for men and women.
• MarineLayer has been able to maintain profitability and grow steadily by taking a measured approach to expansion and focusing on building a strong brand.
• They have plans to continue growing all three distribution channels and are considering international expansion in the future. Marine Layer focuses on creating comfortable and casual clothing for both men and women.
• The stores are designed to feel like a room in your home, with a familiar and intimate atmosphere.
• Respun is Marine Layer's upcycling program that collects old t-shirts and finds new uses for them.
• Marine Layer uses paid social media advertising and catalogs for marketing.
• They have invested in technology like Endless Isle for seamless inventory management and are exploring the use of AI for customer analytics.
• Mike is focused on protecting the company's culture and maintaining a fun and collaborative work environment.
• Marine Layer operates on a hybrid work model, with employees working three days i...

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