The Retail Pilot

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.

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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.

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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.

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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.

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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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