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.

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

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.

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

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.

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

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.

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

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.

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

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.

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

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.

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

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.

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