
The Retail 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.
Hosted by Ausha. See ausha.co/privacy-policy for more information.
Latest episodes

May 9, 2025 • 48min
Tariffs: Two Sides Of Trade
A few weeks ago, I wrote an open letter to President Trump urging him to reverse the extreme tariffs and embargoes imposed on China. These policies have had a significant impact on the apparel, footwear, and toy industries—industries that have long operated offshore due to cost efficiencies and global supply chains. The response was overwhelming: over 800 reactions, 70,000 views, and 50+ reposts on LinkedIn, reflecting broad concern across the industry.However, the post also sparked a thoughtful and passionate response from a former colleague who sees a different path forward—one that includes a revival of U.S.-based manufacturing.In this episode of The Retail Pilot, we sit down for a grounded, no-holds-barred conversation about tariffs, trade, and the real-world ripple effects on American business. Joining me are:Bear Clark, Chief Innovation Instigator at Ear Micro and a pioneer in the hearables industry, who once ran a thriving U.S.-based manufacturing company—until Chinese subsidies and trade shifts changed everything.Jan Rogers Kniffen, CEO of J Rogers Kniffen Worldwide and longtime retail executive and CNBC contributor, who shares sobering insights on the long-term hollowing out of U.S. manufacturing.Adrian Miramontes, COO/CFO of Boston Proper, a women’s apparel brand that manufactures 80%+ of its product in China and now faces existential risk due to tariff-related cost increases.Together, we explore both sides of the issue—from the hopeful possibilities of automation and fair trade to the painful reality many small-to-mid-sized retailers now face. Whether you're a policymaker, entrepreneur, or consumer, this episode will challenge how you think about global sourcing, pricing, and the future of U.S. industry.You’ll Learn:Why my call to reverse tariffs gained massive traction—and pushbackHow Chinese subsidies disrupted entire U.S. industries, one bid at a timeWhy companies like Boston Proper depend on Chinese manufacturingWhat domestic production could look like in the age of automation and AIWhy rushed trade policy reform could do more harm than good without a planThe moral and economic case for reciprocal trade and environmental accountabilityTopics Covered:The decline of American manufacturing over six decadesFast fashion, fair labor, and environmental implicationsTariffs as economic tools: punishment, leverage, or necessity?What a balanced and effective trade strategy might actually look likeFinal Thoughts:We may not all agree on the solution, but this conversation marks a critical starting point: how can the U.S. support fair, strategic trade that benefits workers, business owners, and consumers alike—without trading stability for short-term politics?Hosted by Ausha. See ausha.co/privacy-policy for more information.

Apr 29, 2025 • 42min
Inside the Mind of a Luxury CEO: Daniella Vitale’s Lessons on Retail, Resilience, and Reinvention
In this episode of The Retail Pilot, host Ken Pilot sits down with Daniella Vitale, CEO of Ferragamo and one of the most influential leaders in luxury retail. From wrapping gifts at a small shop in New Jersey to leading some of the biggest names in fashion — including Armani, Gucci, Barneys New York, Tiffany & Co., and now Ferragamo — Daniella shares her remarkable career journey, pivotal leadership lessons, and deep passion for product innovation.Daniella opens up about navigating the digital transformation of legacy brands, scaling Ferragamo’s digital business, and why authentic customer experiences are the future of luxury. She also discusses her philosophy on leadership, career advice for the next generation, and how Ferragamo is evolving its women's business to drive growth in a challenging global market.Whether you're an aspiring fashion executive, a retail enthusiast, or a brand leader navigating change, Daniella’s insights will leave you inspired, informed, and ready to take bold chances.Show Notes:Introduction to Daniella Vitale’s career in luxury retail, including her leadership roles at Armani, Gucci, Barneys New York, Tiffany & Co., and FerragamoHow wrapping gifts as a teenager sparked her lifelong passion for retailThe importance of embracing both product and operations to become a successful CEODaniella’s experience launching digital at Gucci and transforming Barneys' online businessLessons learned from leading Barneys through financial challenges and innovationDriving Ferragamo’s digital growth and building an omnichannel strategyHow Ferragamo is shifting from a men's shoe powerhouse to a women's leather goods leaderThe critical role of customer experiences, lifestyle branding, and storytelling in luxury todayInsight into the evolving challenges in the luxury retail market — from tariffs to changing consumer behaviorsDaniella’s leadership approach: building cohesive, collaborative, and empathetic teamsAdvice for young professionals entering the retail and fashion industriesRapid-fire questions: favorite brands, dream city to live in, favorite shows, and who she’d love to meetIf you found value in this episode, don’t forget to share it with your network and help us spread these inspiring lessons across the industry!Hosted by Ausha. See ausha.co/privacy-policy for more information.

Apr 15, 2025 • 36min
Inside Nuts.com: PJ Oleksak’s Journey From Private Equity to CEO
In this episode of The Retail Pilot, host Ken Pilot welcomes PJ Oleksak, the dynamic CEO of Nuts.com and the first woman and non-family member to lead the 94-year-old business. With a rich background that includes leadership roles at FreshDirect and Slice, PJ shares how she combines a deep understanding of finance with a passion for food to lead transformative change in legacy brands. She walks us through her journey from private equity to pioneering online grocery, her leadership philosophy, and how she’s steering Nuts.com toward omnichannel growth.PJ also discusses the challenges and opportunities in modernizing a family-owned business—building a performance-driven culture, embracing AI and tech innovation, and preparing to launch a sister retail brand. Whether you're in e-commerce, food retail, or scaling a family business, this episode offers practical wisdom on navigating growth while staying true to your roots.Show Notes:Guest: PJ Oleksak, CEO of Nuts.comBackground: Former Chief Growth Officer at FreshDirect and Chief Business Officer at SliceTopics Covered:PJ’s transition from private equity to food techLessons learned from FreshDirect and SliceModernizing a 94-year-old business and earning trust as an outsiderBuilding high-performing, happy teams and instilling accountabilityThe cultural and operational shifts at Nuts.com under her leadershipStrategic moves toward omnichannel growth and retail distributionThe impact of AI across departments, from sales to creativeHow Nuts.com is adapting to rising cocoa costs and sourcing challengesLeadership philosophy and importance of founder-CEO alignmentLooking ahead: launching a sister brand and expanding customer reachKey Insight: Balancing legacy with innovation requires empathy, structure, and a relentless focus on the customer experience.Sponsored by FireworkHosted by Ausha. See ausha.co/privacy-policy for more information.

5 snips
Apr 1, 2025 • 44min
The Architects Behind Brands You Love: How Red Antler Builds Obsession-Worthy Companies
Join Emily Heyward and JB Osborne, co-founders of Red Antler, as they share insights from their renowned branding agency that has birthed icons like Allbirds and Casper. They explore how AI is revolutionizing retail, enhancing consumer interactions and brand strategies. The duo emphasizes the power of empathy and storytelling in building memorable brands. They also discuss their innovative equity-based partnership model and reflect on their favorite campaigns, all while navigating the evolving landscape of consumer expectations.

Mar 25, 2025 • 30min
From The Studio to the Beauty Industry: John Legend on Music & Entrepreneurship
Join EGOT-winning artist and entrepreneur John Legend and A-Frame Brands' CEO Ari Bloom as they explore the world of inclusive skincare with Loved01. John reveals how his passion for music and academics shaped his dual career, while Ari shares insights on launching socially responsible brands. They dive into the importance of catering to melanin-rich skin and the innovative strategies behind their products. Expect a fascinating discussion on the future of beauty marketing and the balance between creativity and business!

Mar 18, 2025 • 43min
From Pottery to Global Design: The Creative Journey of Jonathan Adler
Jonathan Adler, a visionary designer known for his charming sophistication, recounts his transformation from a summer camp pottery enthusiast to the founder of a global design empire. He reveals the importance of humor in his work, emphasizing storytelling within design. Jonathan shares hard-won business lessons, including the significance of strategic partnerships for growth. He also discusses his inspirations, like travel and influential figures, while envisioning the future of creative brands. Plus, hear anecdotes about his lively personal life with husband Simon Doonan.

Mar 4, 2025 • 41min
Power Dressing Reimagined: Sarah LaFleur’s Mission to Simplify Workwear
Sarah LaFleur, Founder and CEO of M.M.LaFleur, shares her journey in redefining women's workwear by focusing on function and ease. She discusses overcoming challenges during COVID and the importance of community. Jan Kniffen, a retail expert, provides insights into the sneaker market, including Nike's comeback and the rise of innovative brands like Hoka and On. Together, they explore entrepreneurial resilience, the evolving landscape of retail, and the future of fashion with technology integration.

Feb 18, 2025 • 35min
Retail Revolution: Dana Telsey on Trends, Tech & the Future of Shopping
In this episode of The Retail Pilot, host Ken Pilot interviews Dana Telsey, CEO and Chief Research Officer of Telsey Advisory Group. They explore key trends shaping the future of retail, including AI-driven personalization, shifting consumer behaviors, and the evolution of store formats. Dana shares insights on top-performing brands like Birkenstock, Warby Parker, and Abercrombie & Fitch, along with the challenges facing luxury retail and department stores. The discussion also covers tariffs, global supply chain shifts, and the increasing role of social media in retail strategy.Key Topics DiscussedDana Telsey’s Career Journey – Her experience in equity research, investment banking, and retail strategyRetail Trends for 2025 – Personalization, curation, and the growing role of AI in retailTop Companies to Watch – Birkenstock, Warby Parker, Walmart, Abercrombie & Fitch, and LululemonLuxury Retail & Department Stores – The Saks-Neiman Marcus merger and the shift toward direct-to-consumer strategiesThe Impact of AI in Retail – Enhancing personalization, content creation, and supply chain managementSocial Media & Retail – The influence of TikTok and social commerce on brand visibilityThe Evolution of Physical Retail – The rise of pop-up shops, smaller store formats, and experiential retailTariffs & Global Production – How supply chain shifts and economic uncertainty affect pricingNike & Sneaker Market Competition – Challenges from rising brands like Hoka, On Running, and SkechersRetail Technology & Customer Experience – AI-powered POS, RFID, and real-time analytics in retailHighlights & Key TakeawaysAI & Personalization – Retailers are investing in AI to refine customer experiences and optimize operationsSuccess of Top Brands – Birkenstock’s full-price strategy, Warby Parker’s store model, and Abercrombie’s resurgenceLuxury Retail Shifts – Direct-to-consumer is becoming the primary focus for major luxury brandsRetail Media Networks – Gaining traction but still proving their impact on sales and customer engagementPower of Social Media – TikTok has become a critical platform for understanding emerging consumer trendsTariffs & Rising Costs – Retailers are diversifying supply chains to reduce dependency on ChinaIn-Store Experience Matters – Brands like Skims and RH are leveraging immersive retail environmentsNike’s Competitive Pressure – Facing challenges from new brands, Nike must redefine its market strategyRetail’s Need for Agility – The most successful brands are those that adapt quickly to changing consumer demandsHosted by Ausha. See ausha.co/privacy-policy for more information.

Feb 4, 2025 • 49min
Crafting The Great: A Vision for Modern Vintage with Emily Current and Meritt Elliott
Ken Pilot interviews Emily Current and Meritt Elliott, Co-Founders of fashion brand, The Great, on this Flight of The Retail Pilot Podcast. Plus, he has a short "Pre-Flight" conversation with Jan Kniffen, former retail executive and current CNBC retail expert, to discuss what 2025 looks like for the retail industry.Pre-Flight with Jan KniffenJan Kniffen shares his outlook for retail in 2025:Retailers are optimistic after a solid 2024 holiday seasonConsumer spending expected to remain healthy, especially among higher-income shoppersLower-income consumers adapting to higher costsTariffs not a major concern for most retailersPositive outlook for discretionary retailers like Ralph Lauren, Nike, LululemonInterview with Emily Current and Meritt ElliottKen speaks with the co-founders of The Great about their journey and brand:Brand OriginsMet as UCLA students, bonded over vintage fashionStarted as celebrity stylists before launching denim brand Current/ElliottFounded The Great in 2015, focusing on casual, nostalgic AmericanaThe Great BrandOffers casual, vintage-inspired clothing across multiple categoriesAbout $50 million in annual revenueDistribution split between e-commerce, retail stores, and wholesaleBusiness ApproachSelf-funded, focused on organic growthValue wholesale partnerships alongside direct-to-consumerEmphasis on in-person experiences and community buildingCollaborationsPartnerships with Eddie Bauer, Birkenstock, Pottery BarnInterested in future collaboration with ConverseMarketing StrategyRely heavily on word-of-mouth and organic growthUse collaborations and retail stores as marketing toolsCelebrity fans include Reese Witherspoon and Rachel BilsonFuture PlansExpanding reach to new geographic marketsConsidering growth in men's, children's, and home categoriesWorking as Co-CEOsEmphasize complementary skills and shared visionStress importance of understanding all aspects of the businessHosted by Ausha. See ausha.co/privacy-policy for more information.

Jan 21, 2025 • 37min
Unraveling the Fabric of Innovation at Faherty with Alex & Mike Faherty
In this episode of The Retail Pilot, host Ken Pilot sits down with Alex and Mike Faherty, co-founders of Faherty Brand, to discuss their business journey, recent successes, and future plans. Key Topics Discussed: Faherty's performance during Black Friday and Cyber Monday 2024The brand's growth trajectory and end-of-year projectionsExpansion of retail stores and focus on in-store experiencesProduct development and bestselling itemsMarketing strategies and collaborationsTech innovations and simplification effortsTeam building and company culturePreparing for potential tariff changes in 2025Exciting plans and collaborations for 2025 Highlights: Faherty now operates 72 stores, with plans to open more in 2025The brand is doing "hundreds of millions" in revenueFocus on hero products like the Legend Shirt and Stretch Terry PantsEmphasis on creating a boutique feel while making shopping easier for customersUpcoming collaborations with a surf club in Ghana and big wave surfers in PortugalHosted by Ausha. See ausha.co/privacy-policy for more information.
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