

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.
Hosted by Ausha. See ausha.co/privacy-policy for more information.
Hosted by Ausha. See ausha.co/privacy-policy for more information.
Episodes
Mentioned books

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.

Jan 21, 2025 • 37min
Open Air Shopping Innovations: Reimagining Retail with Steve Yalof, President & CEO of Tanger, Inc.
In this episode of The Retail Pilot, Ken Pilot welcomes back Stephen Yalof, President and CEO of Tanger, Inc. With over 25 years of experience in the commercial real estate industry, Stephen shares insights into Tanger's growth strategies, the evolution of retail spaces, and how the company is adapting to changing consumer behaviors. From expanding into full-price lifestyle centers to enhancing customer experiences through digital innovation and loyalty programs, Stephen provides a comprehensive look at Tanger's journey and future direction. Key Topics Discussed 1. Tanger’s Recent Successes Performance Highlights: Tanger achieved a 4.3% increase in net operating income (NOI) and a 97.4% occupancy rate. The company executed 543 leases covering 2.6 million square feet over the past year. Expansion Efforts: Recent acquisitions include The Promenade at Chenal in Little Rock, Arkansas, which features the only Apple Store in the state. 2. Growth Strategy Diversification: While maintaining its core outlet business, Tanger is expanding into full-price open-air lifestyle centers that include specialty stores, grocery anchors, and other amenities. Acquisition Focus: Stephen emphasized the importance of acquiring high-quality properties in strategic markets to leverage existing regional management teams. 3. Enhancing Customer Experience Tanger Club Loyalty Program: A tiered membership program offering discounts and perks for shoppers. Members can choose between free or paid memberships ($20 annually) for additional benefits. Digital Integration: Introduction of QR codes for real-time offers and digital savings passports, replacing outdated coupon books. Amenities and Entertainment: Investments in food offerings, gathering spaces, and entertainment options like pickleball courts to create a more engaging shopping experience. 4. Industry Trends Blending Physical and Digital Retail: Tanger is exploring e-commerce integration as part of its long-term strategy while using digital tools to enhance in-store experiences. Health & Beauty Brands: Increased presence of brands like Sephora and Ulta in outlet environments, offering regular-priced products alongside experiential services. 5. Leadership and Team Building Talent Development: Stephen emphasizes hiring complementary skill sets to address organizational blind spots and promoting from within to keep employees motivated. Communication Practices: Regular town halls, employee resource groups (ERGs), and an intranet ensure transparency and engagement across the organization. 6. Reflections on Leadership Lessons Learned: Stephen highlights the importance of "failing fast" to pivot quickly when strategies don’t work. He also stresses the value of building a strong team aligned with company goals. Notable Quotes "Fail fast—if something doesn’t work, pivot quickly and move on." – Stephen Yalof "We’re lifestyle-izing our portfolio by adding food, beverage, amenities, and entertainment to enhance the customer experience." – Stephen Yalof "Our loyalty program is about understanding our customers better and providing them with personalized value." – Stephen YalofHosted by Ausha. See ausha.co/privacy-policy for more information.

Jan 20, 2025 • 59min
Rent the Runway 2.0: Redefining the Future of Fashion with Jennifer Hyman
In this fascinating discussion, Jennifer Hyman, Co-founder and CEO of Rent the Runway, dives into the company's revolutionary impact on fashion. She shares how she pitched the idea to Diane von Furstenberg within 48 hours of conceiving it. Hyman reflects on Rent the Runway's resilience during COVID-19 and the shift towards sustainability and community engagement targeted at young consumers. She also reveals insights about their innovative business model and the emotional experience of taking the company public, highlighting female leadership in the industry.