In this episode of The Retail Pilot, we sit down with Amanda Baldwin, the newly appointed CEO of Olaplex and former CEO of Supergoop, for an in-depth conversation about her remarkable career journey—from Wall Street to the heart of the beauty industry. Amanda shares how her early curiosity about brands evolved into a passion for consumer-driven storytelling, innovation, and leadership in some of the world’s most iconic beauty companies.

We explore her pivotal career moments, including her transition from finance to beauty, the foundational experiences she gained at Estée Lauder and LVMH, and how she scaled Supergoop from a small team to a category-defining brand. Now at the helm of Olaplex, Amanda outlines her vision for rebuilding brand strength, deepening pro community relationships, and driving innovation through groundbreaking R&D.

This episode offers a masterclass in brand leadership, navigating industry change, and staying grounded in purpose while scaling globally.

If you enjoyed this conversation, be sure to like, follow, and leave a review—it helps us reach more listeners and continue bringing you these powerful insights.

Show Notes:

• Amanda’s early curiosity about consumer brands and storytelling

• Lessons learned from Wall Street, Estée Lauder, and LVMH

• The early growth story of Supergoop and how innovation drove scale

• Why product quality and emotional connection are non-negotiable for brand longevity

• Olaplex’s patented technology, salon-first strategy, and Amanda’s plans to reinvigorate the brand

• Investing in team, infrastructure, and culture as part of operational excellence

• Navigating the public markets while staying focused on long-term brand value

• Advice for early-career professionals and the role of mentorship in her success

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

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:

• 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.

  
  

• 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.

  
  

• 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.

  
  

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 pushback

• How Chinese subsidies disrupted entire U.S. industries, one bid at a time

• Why companies like Boston Proper depend on Chinese manufacturing

• What domestic production could look like in the age of automation and AI

• Why rushed trade policy reform could do more harm than good without a plan

• The moral and economic case for reciprocal trade and environmental accountability

Topics Covered:

• The decline of American manufacturing over six decades

• Fast fashion, fair labor, and environmental implications

• Tariffs as economic tools: punishment, leverage, or necessity?

• What a balanced and effective trade strategy might actually look like
  

  
  

Final 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.

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 Ferragamo

• How wrapping gifts as a teenager sparked her lifelong passion for retail

• The importance of embracing both product and operations to become a successful CEO

• Daniella’s experience launching digital at Gucci and transforming Barneys' online business

• Lessons learned from leading Barneys through financial challenges and innovation

• Driving Ferragamo’s digital growth and building an omnichannel strategy

• How Ferragamo is shifting from a men's shoe powerhouse to a women's leather goods leader

• The critical role of customer experiences, lifestyle branding, and storytelling in luxury today

• Insight into the evolving challenges in the luxury retail market — from tariffs to changing consumer behaviors

• Daniella’s leadership approach: building cohesive, collaborative, and empathetic teams

• Advice for young professionals entering the retail and fashion industries

• Rapid-fire questions: favorite brands, dream city to live in, favorite shows, and who she’d love to meet
  

  If 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.

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.com

• Background: Former Chief Growth Officer at FreshDirect and Chief Business Officer at Slice

• Topics Covered:

  • PJ’s transition from private equity to food tech

  • Lessons learned from FreshDirect and Slice

  • Modernizing a 94-year-old business and earning trust as an outsider

  • Building high-performing, happy teams and instilling accountability

  • The cultural and operational shifts at Nuts.com under her leadership

  • Strategic moves toward omnichannel growth and retail distribution

  • The impact of AI across departments, from sales to creative

  • How Nuts.com is adapting to rising cocoa costs and sourcing challenges

  • Leadership philosophy and importance of founder-CEO alignment

  • Looking ahead: launching a sister brand and expanding customer reach

• Key Insight: Balancing legacy with innovation requires empathy, structure, and a relentless focus on the customer experience.

Sponsored by Firework

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

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.

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

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.

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

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.

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.

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

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

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

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