The Retail Pilot

Ken Pilot

The Retail Pilot is a series of interviews conducted by Ken Pilot with “Leaders and Legends” of the Retail industry. Ken will focus the conversation on his guests’ career journeys and their greatest career accomplishments and disappointments; gather insight into their leadership styles; learn who inspired them as they progressed through their careers; identify brands they admire; discover challenges they have faced; and talk about where they think Retail is headed and how they are leveraging technology to get there.

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21 episodes
fortnightly
Avg 52 min
English

Episodes 21

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August 18 · 50 min
Shea Jensen, President of Urban Outfitters North America: Inside the Brand's Comeback
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...
August 4 · 1 hr 4 min
Neil Saunders, Managing Director of GlobalData: Inside Retail's Winners, Losers & the Back Half of 2026
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...
July 21 · 58 min
Vuori Founder Joe Kudla: From Garage Startup to $5Billion+ Activewear Brand
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 fir...
July 7 · 56 min
James Reinhart, Co-Founder & CEO of Thredup: Building the Future of Resale
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...
June 23 · 46 min
Denise Incandela, EVP of Walmart Fashion: How Walmart Became a True Fashion Destination
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 transform...
June 2 · 55 min
Tanya Golesic, CEO of Mackage: From Canadian down to a Global Luxury Brand
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 lac...
May 19 · 45 min
Pete Nordstrom: From public to private, Nordstrom’s gains momentum.
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...
May 6 · 1 hr 9 min
Retail Legend Mickey Drexler: From Building Gap & Old Navy to Running Alex Mill Like a Startup
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. "...
April 14 · 57 min
Rhone CEO Nate Checketts on Mind & Body Wellness: How Mental Fitness Built a $100M Performance Brand
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 we...
March 13 · 55 min
Guggenheim Analyst Simeon Siegel: Why Revenue Matters More Than Hype in Retail + 2026 Stock Picks
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 co...
February 24 · 59 min
The Department Store Crisis: Terry Lundgren & Jan Rogers Kniffen on Saks Global Bankruptcy and What The Future Holds for Department Stores
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, f...
February 10 · 42 min
Lizanne Kindler Leading A $6 Billion Fashion Empire, The KnitWell Group
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 int...
January 27 · 51 min
Breaking the Salon Ceiling: How Madison Reed Redefined Hair Color with Amy Errett
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 wit...
Dec 16, 2025 · 32 min
Why Retail Is Holding Up Better Than Expected with Matt Shay
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...
Dec 12, 2025 · 53 min
A Legacy of Style and Innovation with Gene Pressman
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...
Nov 25, 2025 · 51 min
The Evolution of Coach: Lew Frankfort on Culture, Consumers, and Creative Leadership
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...
Nov 13, 2025 · 48 min
Inside Tecovas: The $300 Million Brand Redefining Western Retail
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 expa...
Oct 28, 2025 · 51 min
Clean Beauty Movement: Gregg Renfrew on Reinventing Beauty with Counter
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 selli...
Oct 14, 2025 · 40 min
The Ralph Lauren Way: Storytelling, Style, and Staying Power with David Lauren
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 stor...
Sep 23, 2025 · 1 hr 3 min
Fashionphile’s Rise: Where Resale Meets Reinvention
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 beg...

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