The Retail Pilot

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.

29 Apr 42min

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.

15 Apr 35min

In this episode of The Retail Pilot, host Ken Pilot dives into the future of branding and retail innovation with Emily Heyward & JB Osborne, Co-Founders of Red Antler and a pre-flight discussion with retail futurist Jan Kniffen. From the transformative role of AI in customer experience to the secret sauce behind some of today’s most iconic brands, this conversation explores how emotional resonance, creativity, and technology intersect in modern retail. Ken, Emily, and JB also discuss brand building from scratch, the challenges of rebranding, and their venture fund Habitat Partners. Plus, they reflect on favorite campaigns, dream brand revivals, and the evolving landscape of consumer expectations.Show NotesKen Pilot introduces the episode with commentary from retail expert Jan Kniffen on the seismic impact of AI across industries, especially in retail.Jan shares why AI will redefine omnichannel experiences and customer expectations, emphasizing the urgency for retailers to invest or fall behind.Emily Hayward and JB Osborne join Ken to discuss Red Antler’s approach to branding, which centers on empathy, storytelling, and strategic creativity.Insights into how Red Antler partners with early-stage founders and legacy businesses, building emotional connections through meaningful brand positioning.Reflections on helping launch brands like Allbirds, Casper, Burrow, and Hinge, including the challenges and rewards of naming and storytelling.Candid thoughts on the rise and stumbles of DTC pioneers and how capital structure, not branding, often drives downfall.A look at Habitat Partners, their investment arm, and why equity plays helped foster long-term alignment with founders.Exploration of how AI is impacting creative workflows, campaign ideation, and brand communication.Rapid fire favorites, from travel destinations to go-to coffee brands, and the dream jobs Emily and JB would pursue outside of Red Antler.Plus, JB and Emily name the brands they’d love to reimagine—from OpenTable to LinkedIn—and share their vision for brand leadership in a tech-driven era.This episode is sponsored by Firework.Hosted by Ausha. See ausha.co/privacy-policy for more information.

1 Apr 44min

In this inspiring episode of The Retail Pilot: Leaders & Legends, host Ken Pilot sits down with EGOT-winning artist and entrepreneur John Legend, alongside brand builder Ari Bloom, co-founder and CEO of A-Frame Brands. Together, they unpack the story behind their inclusive skincare line Loved01—a brand created with intention, affordability, and care for melanin-rich and sensitive skin.John shares how his dual passion for music and academics shaped his career, why love is the foundation of everything he creates, and what it’s like building a brand with his longtime stylistic and creative team. Ari details the strategy behind launching socially conscious brands through A-Frame, lessons from live selling on QVC and Amazon, and how the data is shaping their next moves.👉 Promo Code: Get 25% off your next Loved01 purchase at Loved01.com with code PILOT25 — valid through May 1.📌 Chapters & Highlights:.John’s Early Career PathFrom piano lessons at 4 to BCG consultant by day and musician by night—how John balanced brains and creativity.The Origin of A-Frame & Loved01Ari shares how A-Frame Brands came to life and why teaming up with John was a natural fit.Why the Name “Loved01”The personal meaning behind the brand name and how it reflects self-care and connection.Filling the Skincare GapDesigning products for melanin-rich and aging skin—without celebrity price tags.Formulation & Sourcing StrategyHow Loved01 created high-quality, plant-based products domestically with no compromises.Chrissy Teigen’s Favorite ProductsWhat John’s wife loves about the brand—and why their $15 exfoliator beats high-end competitors.Retail Approach & AffordabilityThe importance of being accessible—through retailers like CVS, Amazon, and QVC.The Power of Live SellingWhy QVC, CBS, and Amazon are outperforming traditional ad spend—and how John’s charisma shines through.Using Data to Drive GrowthHow real-time feedback helps the team pivot, learn, and win with the right audiences.Expanding the Brand & What’s NextNew products, fragrance updates, B2B partnerships, and opportunities in hospitality.Rapid Fire FunJohn shares his favorite clothing brands, travel destination, dream meeting, and more.Hosted by Ausha. See ausha.co/privacy-policy for more information.

25 Mar 29min

On this episode of The Retail Pilot, host Ken Pilot welcomes the visionary designer and founder, Jonathan Adler. Known for his signature blend of chic sophistication and playful wit, Jonathan shares his incredible journey from an aspiring potter to building a global design empire. From his early days spinning clay at summer camp to landing his first collection at Barney’s and expanding into furniture, lighting, and decor—this episode is packed with insights on resilience, creativity, and building a timeless brand.Jonathan also speaks into the intersection of business and design, the importance of humor in his work, his collaboration with Consortium, and his vision for the future of retail. Plus, hear about his relationship with husband Simon Doonan, the lessons he's learned over 30+ years in business, and why he believes in the power of "more."Key Takeaways:🔹 How Jonathan Adler transformed his passion for pottery into a global lifestyle brand🔹 The importance of humor and storytelling in design🔹 The business lessons he learned the hard way (including forgetting to send his first invoice!)🔹 Why he believes in the power of “more” when it comes to brand expansion🔹 His favorite sources of inspiration, from Slim Aarons to travel destinations💡 Enjoyed the episode? Leave us a review on your favorite podcast platform!Hosted by Ausha. See ausha.co/privacy-policy for more information.

18 Mar 43min

In this episode of The Retail Pilot, host Ken Pilot kicks off with a PreFlight segment featuring retail expert Jan Kniffen. They dive into the ever-changing sneaker market, discussing Nike’s comeback, the rise of On Running and Hoka, and how brands like Skechers and New Balance are shaking up the industry.Following PreFlight, Ken welcomes special guest Sarah LaFleur, Founder and CEO of M.M.LaFleur, for an insightful conversation about how she built a brand that redefined workwear for women. From launching the company in 2013 to navigating the challenges of COVID and financial setbacks, Sarah shares her journey of resilience, innovation, and customer-driven design.Learn how M.M.LaFleur’s mission to simplify dressing for professional women has evolved, how Sarah leveraged trunk shows and word-of-mouth marketing to scale the brand, and why she believes adaptability is key to entrepreneurial success. Plus, she shares insights on the future of retail, the role of AI in fashion, and her vision for M.M.LaFleur in the next decade.Key Takeaways:✈️ PreFlight with Jan Kniffen:🔹 The rise of smaller sneaker brands and how they’re impacting Nike & Adidas🔹 Why Nike is poised for a strong comeback in 2025-2026🔹 How the running shoe market is evolving and what it means for retailers🛫 Main Interview with Sarah LaFleur:🔹 The inspiration behind M.M.LaFleur and how it started🔹 How Sarah built a brand focused on function, fashion, and ease🔹 The impact of COVID on retail and how M.M.LaFleur pivoted🔹 Raising capital and overcoming financial hurdles in record time🔹 The future of retail and the role of AI in fashion🔹 The power of mentorship and community support🎧 Listen Now on Your Favorite Podcast Platform!Don’t forget to leave us a review and share this episode.Hosted by Ausha. See ausha.co/privacy-policy for more information.

4 Mar 41min

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.

18 Feb 35min

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.

4 Feb 48min