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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