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 Notes

• Ken 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.

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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 Path
  From piano lessons at 4 to BCG consultant by day and musician by night—how John balanced brains and creativity.

• The Origin of A-Frame & Loved01
  Ari 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 Gap
  Designing products for melanin-rich and aging skin—without celebrity price tags.

• Formulation & Sourcing Strategy
  How Loved01 created high-quality, plant-based products domestically with no compromises.

• Chrissy Teigen’s Favorite Products
  What John’s wife loves about the brand—and why their $15 exfoliator beats high-end competitors.

• Retail Approach & Affordability
  The importance of being accessible—through retailers like CVS, Amazon, and QVC.

• The Power of Live Selling
  Why QVC, CBS, and Amazon are outperforming traditional ad spend—and how John’s charisma shines through.

• Using Data to Drive Growth
  How real-time feedback helps the team pivot, learn, and win with the right audiences.

• Expanding the Brand & What’s Next
  New products, fragrance updates, B2B partnerships, and opportunities in hospitality.

• Rapid Fire Fun
  John shares his favorite clothing brands, travel destination, dream meeting, and more.

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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!

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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.

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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 Discussed

• Dana Telsey’s Career Journey – Her experience in equity research, investment banking, and retail strategy

• Retail Trends for 2025 – Personalization, curation, and the growing role of AI in retail

• Top Companies to Watch – Birkenstock, Warby Parker, Walmart, Abercrombie & Fitch, and Lululemon

• Luxury Retail & Department Stores – The Saks-Neiman Marcus merger and the shift toward direct-to-consumer strategies

• The Impact of AI in Retail – Enhancing personalization, content creation, and supply chain management

• Social Media & Retail – The influence of TikTok and social commerce on brand visibility

• The Evolution of Physical Retail – The rise of pop-up shops, smaller store formats, and experiential retail

• Tariffs & Global Production – How supply chain shifts and economic uncertainty affect pricing

• Nike & Sneaker Market Competition – Challenges from rising brands like Hoka, On Running, and Skechers

• Retail Technology & Customer Experience – AI-powered POS, RFID, and real-time analytics in retail
  
  

Highlights & Key Takeaways

• AI & Personalization – Retailers are investing in AI to refine customer experiences and optimize operations

• Success of Top Brands – Birkenstock’s full-price strategy, Warby Parker’s store model, and Abercrombie’s resurgence

• Luxury Retail Shifts – Direct-to-consumer is becoming the primary focus for major luxury brands

• Retail Media Networks – Gaining traction but still proving their impact on sales and customer engagement

• Power of Social Media – TikTok has become a critical platform for understanding emerging consumer trends

• Tariffs & Rising Costs – Retailers are diversifying supply chains to reduce dependency on China

• In-Store Experience Matters – Brands like Skims and RH are leveraging immersive retail environments

• Nike’s Competitive Pressure – Facing challenges from new brands, Nike must redefine its market strategy

• Retail’s Need for Agility – The most successful brands are those that adapt quickly to changing consumer demands

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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 Kniffen

Jan Kniffen shares his outlook for retail in 2025:

• Retailers are optimistic after a solid 2024 holiday season

• Consumer spending expected to remain healthy, especially among higher-income shoppers

• Lower-income consumers adapting to higher costs

• Tariffs not a major concern for most retailers

• Positive outlook for discretionary retailers like Ralph Lauren, Nike, Lululemon

Interview with Emily Current and Meritt Elliott

Ken speaks with the co-founders of The Great about their journey and brand:

Brand Origins

• Met as UCLA students, bonded over vintage fashion

• Started as celebrity stylists before launching denim brand Current/Elliott

• Founded The Great in 2015, focusing on casual, nostalgic Americana

  
  

The Great Brand

• Offers casual, vintage-inspired clothing across multiple categories

• About $50 million in annual revenue

• Distribution split between e-commerce, retail stores, and wholesale

  
  

Business Approach

• Self-funded, focused on organic growth

• Value wholesale partnerships alongside direct-to-consumer

• Emphasis on in-person experiences and community building

  
  

Collaborations

• Partnerships with Eddie Bauer, Birkenstock, Pottery Barn

• Interested in future collaboration with Converse

  
  

Marketing Strategy

• Rely heavily on word-of-mouth and organic growth

• Use collaborations and retail stores as marketing tools

• Celebrity fans include Reese Witherspoon and Rachel Bilson

  
  

Future Plans

• Expanding reach to new geographic markets

• Considering growth in men's, children's, and home categories

  
  

Working as Co-CEOs

• Emphasize complementary skills and shared vision

• Stress importance of understanding all aspects of the business

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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 2024

• The brand's growth trajectory and end-of-year projections

• Expansion of retail stores and focus on in-store experiences

• Product development and bestselling items

• Marketing strategies and collaborations

• Tech innovations and simplification efforts

• Team building and company culture

• Preparing for potential tariff changes in 2025

• Exciting plans and collaborations for 2025

Highlights:

• Faherty now operates 72 stores, with plans to open more in 2025

• The brand is doing "hundreds of millions" in revenue

• Focus on hero products like the Legend Shirt and Stretch Terry Pants

• Emphasis on creating a boutique feel while making shopping easier for customers

• Upcoming collaborations with a surf club in Ghana and big wave surfers in Portugal

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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 Yalof

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Rent the Runway 2.0 - Redefining the Future of Fashion with Jennifer Hyman

Jennifer Hyman, co-founder and CEO of Rent the Runway, joins Ken Pilot to discuss the company's journey over the past 15 years.

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, a company that is disrupting the trillion-dollar fashion industry with the world’s first and largest shared designer closet. She has led the company for 15 years through all stages of growth, from inception in 2009 to a scale of more than 3M lifetime customers. Jennifer took the company public in 2021, making her the first woman ever to IPO a company with an all-female executive suite and the 30th woman ever to IPO a company. She has been honored on the TIME Top 100 Most Influential People List and the CNBC Disruptor List for 5 out of 10 years. She also serves on the Board of Directors of The Estée Lauder Companies and Zalando.

Rent the Runway's Origins and Growth

• Hyman pitched the concept to Diane von Furstenberg 48 hours after having the idea

• The company now rents about $5 billion worth of designer clothing annually

• Rent the Runway works with over 1,000 designers and has had 100% brand retention over 15 years

Business Model and Profitability

• The company has focused on becoming capital-light, with revenue sharing agreements with brands.

• Rent the Runway has more than doubled its margins over the last few years.

• The goal is to reach free cash flow breakeven.

Challenges and Resilience

• COVID-19 presented significant challenges for the business.

• Hyman emphasizes the importance of resilience and staying in the game.

Marketing and Customer Acquisition

• The company is refocusing on top-of-funnel marketing activities.

• Rent the Runway is leveraging its community and introducing new initiatives like the "Icons" program.

  
  

Physical Retail and Partnerships

• Hyman expresses interest in partnerships with retailers like Sephora, Ulta, or Zara.

• Previous partnerships with Neiman Marcus drove significant foot traffic.

Industry Insights

• Hyman discusses the disruption in the fashion industry, particularly from companies like Shein and Amazon.

• She notes the changing perception of brand value among consumers. T

• echnology and AI Rent the Runway is exploring AI applications in various areas, including photography, customer service, and search algorithms.

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Jennifer Hyman, co-founder and CEO of Rent the Runway, joins Ken Pilot to discuss the company's journey over the past 15 years.

Rent the Runway's Origins and Growth

• Hyman pitched the concept to Diane von Furstenberg 48 hours after having the idea
• The company now rents about $5 billion worth of designer clothing annually
• Rent the Runway works with over 1,000 designers and has had 100% brand retention over 15 years

Business Model and Profitability

• The company has focused on becoming capital-light, with revenue sharing agreements with brands.
• Rent the Runway has more than doubled its margins over the last few years.
• The goal is to reach free cash flow breakeven.

Challenges and Resilience

• COVID-19 presented significant challenges for the business.
• Hyman emphasizes the importance of resilience and staying in the game.

Marketing and Customer Acquisition

• The company is refocusing on top-of-funnel marketing activities.
• Rent the Runway is leveraging its community and introducing new initiatives like the "Icons" program.

Physical Retail and Partnerships

• Hyman expresses interest in partnerships with retailers like Sephora, Ulta, or Zara.
• Previous partnerships with Neiman Marcus drove significant foot traffic.

Industry Insights

• Hyman discusses the disruption in the fashion industry, particularly from companies like Shein and Amazon.
• She notes the changing perception of brand value among consumers.

Technology and AI

• Rent the Runway is exploring AI applications in various areas, including photography, customer service, and search algorithms.