The Retail Pilot

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-teache...

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 l...

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...

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...

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,...

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...

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 St...

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 w...

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...

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, spotte...

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 navigat...

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...

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 th...

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 Weste...

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 mov...

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 cr...

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 pi...

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,” Ma...

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 b...

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 litiga...

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 w...

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 edito...

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 po...

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,...

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...