The Retail Pilot (Ken Pilot)

Ken interviews Amy Williams, the CEO at Citizens of Humanity Group, for this Flight of The Retail Pilot. Amy joined Citizens of Humanity as the company’s President in 2009 and ultimately assumed the Chief Executive Officer position in 2015, overseeing the business for the company’s family of brands including Citizens of Humanity and AGOLDE. Williams previous experience includes Executive Vice President at Lucky Brand Jeans and Senior Vice President of Product Development and Design for Gap Inc. Williams serves on the board at Girls Inc of Greater Los Angeles and empowerHER. She is an advisor to Every Mother Counts and Bay Area Women’s Sports Initiative. 

Key Takeaways Include:

1.    Bridging Business and Design: Amy's career trajectory highlights the importance of bridging the gap between business strategy and creative design in the retail industry. She emphasized the significance of understanding consumer preferences, maintaining commercial viability, and fostering collaboration between merchandising and design teams. This balance between creativity and business acumen is crucial for successful product development and brand growth.

2.    Entrepreneurial Leadership: Amy's transition from corporate roles to entrepreneurial ventures demonstrates her adaptability and leadership versatility. She thrived in both structured corporate environments, such as at Gap Inc., and in more dynamic, entrepreneurial settings, such as at Lucky Brand and Citizens of Humanity. Her ability to navigate different organizational cultures and drive results underscores the importance of entrepreneurial spirit and strategic vision in leadership roles.

3.    Strategic Distribution Expansion: At Citizens of Humanity, Amy was tasked with developing a distribution strategy to expand beyond traditional wholesale channels. This involved exploring opportunities in specialty retail and e-commerce while working closely with company founders and private equity stakeholders. Amy's focus on diversifying distribution channels and adapting to evolving market trends reflects the agility and foresight required to drive brand expansion and maximize growth potential in the competitive retail landscape.

4.    Sustainable Growth and Brand Integrity: Amy emphasizes the importance of sustainable growth and brand integrity. Citizens of Humanity and A Golde focus on quality products, investing in design, and maintaining high standards in distribution. They prioritize long-term brand development over short-term financial gains, taking inspiration from European brands that prioritize generational development.

5.    Strategic Expansion and Retail Experience: The company aims to expand its retail presence thoughtfully, focusing on creating experiential and lifestyle-oriented stores rather than rapid expansion for the sake of growth. They seek to deepen relationships with existing retail partners, improve retail presentations, and explore opportunities for retail expansion in select locations.

6.    Marketing and Brand Building: Instead of traditional marketing methods, Citizens of Humanity and A Goldie rely on organic brand building and word-of-mouth promotion. They prioritize product quality and strategic partnerships with tastemakers, avoiding paid advertising and focusing on creating a desirable brand image through events, partnerships, and thoughtful product placement.

7.    Focus on Technology and Operations: While the company acknowledges the importance of technology in advancing their business, they admit to being more focused on other aspects due to their smaller team size. However, they recognize the need for technological advancements, particularly in areas such as inventory management and data analytics. Improving inventory accuracy, tracking product performance, and opti...

Ken Pilot interviews Sheryl Clark, CEO & President of Boston Proper, a best-kept secret for women over 40, designing unique, on-trend, high-quality fashion for every occasion. Sheryl’s experience includes time at Bloomingdales, Gap and Old Navy prior to joining Boston Proper.

Key highlights of the interview are:

1. Sheryl's Background and Career Journey: Sheryl shares her background, growing up in an Italian immigrant family, and her early fascination with clothing. She discusses her education in business economics and fashion merchandising, as well as her start in the Bloomingdale's executive training program.
2. Career at Gap Inc.: Sheryl talks about her time at Gap Inc., including her experiences at Bloomingdale's and the Gap. She highlights a pivotal moment when she took on a VP of men's position, demonstrating the importance of being open to new opportunities.
3. Transition to Old Navy: Sheryl discusses her transition to Old Navy, where she played a significant role in the brand's growth and success. She emphasizes the importance of key items and marketing in differentiating the brand.
4. Challenges and Growth at Boston Proper: Sheryl shares her decision to leave Gap Inc. and join Boston Proper as CEO. She reflects on the challenges and changes the company underwent, including a sale to Chico's and a subsequent transition to private equity ownership. She also introduces the concept of "Lucy," the brand's target customer.
5. Future Plans and Strategies: Sheryl outlines the three pillars of Boston Proper's growth strategy: shifting from catalog-focused to customer-focused, enhancing customer experience, and going digital. She also announces the upcoming launch of the Miracle marketplace, which aims to expand the brand's assortment and reach new customers.
6. Marketplace Strategy vs. Pure Wholesale: Sheryl Clark discusses Boston Proper's interest in utilizing the Miracle Marketplace Network rather than pure wholesale due to margin considerations and the need to refine their sourcing strategy.
7. Transition to Digital: Sheryl emphasizes the brand's shift towards digital, acknowledging the challenge of transitioning a 30-year-old catalog-centric culture to a digital-focused approach.
8. Introduction of a Loyalty Program: Sheryl mentions the launch of Boston Proper's first-ever loyalty program with Yap-O, aiming to increase customer frequency and average order value.
9. Technological Advancements: Sheryl outlines the adoption of various technologies to enhance customer experience, including Publitas for digitizing the physical catalog, Gorgias for customer service, and exploring shoppable video platforms like Firework.
10. Marketing Shift Towards Digital: Sheryl discusses the evolution of Boston Proper's marketing strategy from predominantly catalog-based to allocating over 50% of marketing spend on digital channels. She highlights successful ventures into OTT advertising and podcasts with iHeartMedia.

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Join Ken as he sits down with two retail extraordinaires, Gary Sheinbaum, CEO of Ashley Stewart, and Nadia Boujarwah, Co-Founder and CEO at Dia&Co. Discover how they're taking the plus-size industry by storm with their dynamic strategies and cutting-edge insights.

From fashion to empowerment, learn how these industry leaders are changing the game and making a difference.

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Ken Pilot interviews Peiman Raf, Co-Founder and CEO of Madhappy, for this 50th Flight of The Retail Pilot - Leaders & Legends podcast. This interview was conducted live at The University of Michigan's Ross School of Business at the Michigan Fashion and Multimedia Summit.

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In this episode first aired May 8, 2023, Ken sits down with Louisa Serene Schneider, Founder and CEO of Rowan, a company that offers safe ear piercings exclusively by licensed nurses. Louisa shares her journey from being a hedge fund analyst to launching Rowan in 2017 and raising over $35 million in venture funding. 

Join Ken as he dives into Louisa's journey and learn how she turned her passion for creating a safer ear piercing experience into a successful business venture!

Key Takeaways from this interview include:

1.    Unique Business Idea and Inception: Louisa's "aha moment" for starting Rowan came from her research and personal experiences, noticing the lack of safe and reputable places for ear piercing. This led to the founding of Rowan, a company that prioritizes safety by using licensed nurses for ear piercings.

2.    Growth and Expansion: Since its inception in 2017, Rowan has rapidly expanded, with 25 studios expected to be open soon and plans to reach 35 by the end of 2023. The company has successfully scaled across various locations, including major cities and diverse areas, proving its business model's adaptability and appeal.

3.    Pivot from Target to Standalone Stores: Initially, Rowan offered services within Target stores but later pivoted to standalone stores due to operational challenges and better performance metrics from their own locations. This strategic shift allowed Rowan to focus on its core business and optimize customer experience.

4.    Financial Performance and Profitability: Rowan's stores have shown impressive financial performance, with some achieving break-even points in well under a year and generating strong sales per square foot. Although the company is currently profitable at the unit level, growth expenses mean that overall profitability is still a work in progress.

5.    Future Growth and Potential: Rowan is considering various growth strategies, including international expansion, partnerships, and potentially exploring new services like nose piercings. The company remains focused on expanding its footprint while maintaining high standards of safety and customer satisfaction.

6.    Value of a Strong Board: Louisa emphasized the importance of assembling a great board of directors. She highlighted members like Tracy Gardner, Anna Badell, and Mike Bifano, each bringing unique expertise and support to the company. Having knowledgeable and candid board members is crucial for a company's success.

7.    Inspirational Leaders and Companies: Louisa admires various leaders and companies for their innovative and resilient business models. She mentioned Berkshire Hathaway for its straightforward acquisition strategy, the revival of Banana Republic, and brands like Lululemon and Hermes for their excellence in their respective markets.

8.    Learning from Challenges: Reflecting on her experience with Target, Louisa discussed the importance of learning from business challenges. While the partnership didn’t end as envisioned, it provided significant brand recognition and valuable insights about the company. The experience highlighted the need to adapt and make informed decisions despite having imperfect information.

9.    Technology and Retail: Louisa shared insights into the tech stack Rowan uses, including Shopify for e-commerce, NetSuite for ERP, and Gorgeous for customer service. She highlighted the importance of choosing the right technology platforms early in a company's development to enhance customer experience and operational efficiency.

10. Pragmatic Approach to Innovation: Louisa discussed the pilot program for virtual try-on technology, weighing its benefits against its costs and feasibility for their current scale. She concluded that while the te...

Ken Pilot interviews Danielle Bernstein on this episode of The Retail Pilot podcast.

Danielle is a native New Yorker and fashion influencer turned business mogul. She has a dedicated fan base of over 3.3 million followers and counting across her social media platforms. Danielle started her internationally recognized blog in 2010 as a daily dose of outfit inspiration for women everywhere, before growing the platform into an aspirational yet relatable home for all things coveted. Danielle has since launched her brand, Shop WeWoreWhat, a direct to consumer and wholesale business with millions of customers worldwide.

Key takeaways from this podcast interview include:

· Value of Early Work Experience: Danielle emphasized the importance of early career "bitch work" in building character, work ethic, and appreciation for later success. Her experiences folding clothes, steaming garments, and doing menial tasks gave her valuable perspective and helped shape her career.

· Adaptability and Innovation in Career Development: Danielle's journey into fashion was unplanned. Initially interested in event planning and nightlife, she pivoted to fashion during college. Her ability to adapt and innovate, particularly with the launch of her street style blog "We Wore What," showcases the importance of seizing new opportunities and being an early adopter of social media.

· Authenticity and Risk-Taking: Danielle discussed the importance of authenticity in her personal and professional life. She highlighted her willingness to take risks and pursue what she wants, whether in her love life or business ventures. This proactive and fearless approach has been crucial to her success.

· Building a Diverse and Inclusive Brand: The "We Wore What" brand caters to a broad demographic, with price points under $200, ensuring accessibility. Danielle's commitment to maintaining a high-low mix in her wardrobe reflects her belief that style isn't about expensive labels but about creativity and personal expression.

· Long-Term Brand Partnerships and Influencer Integrity: Danielle values long-term partnerships over one-off deals, which she believes build trust with her audience. She advises other influencers to adopt a similar approach, focusing on authentic, enduring collaborations rather than short-term financial gains. This strategy has helped her maintain credibility and longevity in her career.

· Creative Process and Inspiration: Danielle Bernstein elaborates on her creative process, highlighting the importance of data-driven design based on past best-sellers, customer feedback, and personal inspiration from everyday items and runways. She emphasizes "smart designing" by reinventing successful styles to create new products.

· Controversy and Resilience: Addressing past controversies regarding accusations of copying designs, Danielle firmly denies these claims and underscores the rigorous, multi-layered process her design team follows to ensure originality. She reflects on how facing cancel culture has made her stronger as a leader and business owner.

· Campaigns and Storytelling: Bernstein discusses the significance of themed collections and destination-based photo shoots in creating a compelling narrative for her brand. Locations like St. Barthes and Italy are chosen to enhance the storytelling aspect of her collections, making the process engaging for followers and customers.

· Influencer Marketing and Brand Strategy: Danielle notes the shift in influencer marketing towards a more results-oriented approach, where brands focus on monetary ROI. She points out that longevity in the industry requires filling a unique market niche and having the ability to sell products effectively.

Ken interviews Sharon Price John, President and CEO of Build-A-Bear Workshop since 2013, where she has led the turning around and redefining of the multimillion-dollar company.

Sharon graduated from the University of Tennessee, worked in the ad industry in New York City, earned an MBA from Columbia University, and managed iconic kids’ brands at companies like Mattel and Hasbro before accepting the role of president of the Stride Rite Children’s Group, which led to her taking the helm at Build-A-Bear.

Sharon also serves on the board of directors at Jack in the Box, and on the executive committee of the Toy Industry Association board. She has been named to the University of Tennessee’s Top 100 Alumni of the last 100 years and recognized as a Distinguished Alumni by Columbia Women in Business. In March 2023, she was number six on the Forbes 20 Customer-Centric Companies Led by Women.

Recently, Sharon has authored and published the book "Stories & Heart: Unlock the Power of Personal Stories to Create a Life You Love," which has achieved impressive success since its release in January 2023.

Sharon has three children and lives in St. Louis with her husband, Russ.

Key Takeaways from this episode include:

1.    Turnaround Expertise: Sharon Price John shared her experience in turning around companies, drawing parallels between her work at StrideRite and Build-A-Bear. She emphasized the importance of strategic decisions, cost-cutting measures, and aligning the organization towards a common goal.

2.    Experiential Retail and Adaptability: The discussion highlighted Build-A-Bear's emphasis on experiential retail, with the closure of physical stores during the pandemic presenting a unique challenge. Sharon discussed the company's swift adaptation, leveraging online sales and the fortunate timing of key initiatives, such as the partnership with Salesforce.

3.    Baby Yoda Strategy: The timely identification and retention of the popular character Baby Yoda (from The Mandalorian) became a crucial element in sustaining revenue during the pandemic. Build-A-Bear's decision to hold inventory and focus on online sales, using Baby Yoda as a catalyst, showcased strategic foresight.

4.    Employee Engagement: Sharon shared a motivational approach used during the challenging times, encouraging employees to view financial goals as catching a metaphorical dollar bill. This approach helped instill a sense of responsibility and accountability, creating a positive impact on the organization's financial performance.

5.    Future Initiatives: Looking forward, Build-A-Bear has outlined key initiatives for the future, including the expansion to additional locations, enhancing the digital experience, and reinvesting in the business. These initiatives aim to build on the momentum gained during the pandemic and position the company for continued success.

6.    Diversification of Store Models: Build-A-Bear has evolved its store model significantly. They have various types of stores, including owned and operated, partnership models with companies like Great Wolf Lodge and Carnival Cruise Lines, temporary pop-up shops, and franchise businesses in multiple countries.

7.    Enhancing In-Store Experience: The company has focused on improving the in-store experience by updating store formats, introducing a discovery format, and enhancing the efficiency of the stuffing process. The renegotiation of leases and consideration for turnover dynamics has been part of their strategy.

8.    Adaptation to COVID Challenges: Build-A-Bear did not significantly close stores during the COVID period but focused on renegotiating leases. They navigated the challenges posed by the pandemic, especially in international franchises like India and Ch...

Ken sits down with Hali Borenstein, CEO of Reformation, for this episode of The Retail Pilot - Leaders & Legends.

Bio

Hali Borenstein is the CEO of sustainable fashion brand Reformation. Hali has been with Reformation since 2014, when she joined the company as Director of Merchandising, and most recently served as President of the company prior becoming CEO.

Under Hali’s leadership, Reformation has grown to 1,000 team members, over 40 retail locations and its international business has more than tripled. She has also overseen significant category expansion and product innovation during her tenure, establishing Reformation as a day-to-day wardrobe staple. Hali has accelerated the brand’s progress toward its lofty sustainability commitments, including Climate Positive by 2025 and a new commitment to be fully Circular by 2030.

A native of Miami Beach, Florida, Hali received her BA from Duke and her MBA from the Stanford. In addition to her role at Reformation, she serves on the Board of Directors for Carter’s Inc. Hali currently lives in Los Angeles with her husband and their two daughters.

Summary

Hali Borenstein, CEO of Reformation, shares her journey in the retail industry, the growth of Reformation, and the unique store experience. She discusses the impact of a major investor, the company's growth strategy, and the innovative technology used in Reformation stores. In this conversation, Hali discusses Reformation's commitment to sustainability, their approach to sustainable fabrics, factory partnerships, circularity, vintage products, and marketing strategies. She also shares insights on leadership, mentors, and lessons learned from past decisions.

Takeaways

• Hali's background in retail and her journey to becoming the CEO of Reformation
• The impact of a major investor on Reformation's growth and expansion
• The unique store experience and innovative technology used in Reformation stores
• Reformation's mission is to bring sustainable fashion to everyone, and sustainability is at the core of their business practices.
• The majority of Reformation's products come from sustainable materials, and they are committed to minimizing the use of non-sustainable fabrics.
• Reformation's factory partnerships, commitment to circularity, and vintage product offerings align with their broader mission of sustainability.
• The company's marketing strategy focuses on building great content, brand awareness, and collaborations with influential figures and brands.
• Hali's leadership style is influenced by various mentors and lessons learned from different leaders, emphasizing the importance of asking questions and seeking expertise when needed.

Chapters

00:00

Journey to Retail CEO

03:10

Impact of Major Investor

10:41

Innovative Store Experience and Technology

13:34

Growth Strategy and Expansion

25:52

Sustainable Fabrics and Circular Economy

32:02

Vintage Products and Circular Business Model

34:44

Innovative Marketing Strategies

40:21

Lessons in Leadership and Decision-Making

Keywords

retail, Reformation, CEO, growth strategy, technology, store experience, sustainability, investor, expansion, sustainability, sustainable fashion, supply chain, circularity, vintage, marketing, leadership, mentors, decision-making

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Ken Pilot speaks with Ramy Brook Sharp one year later on The Retail Pilot podcast. Ramy is the Founder and CEO of eponymous brand, Ramy Brook.

In this conversation, Ken and Ramy discuss the current state of Ramy Brook, a fashion brand, and the strategies they are implementing to grow the business. They talk about the balance between wholesale and e-commerce, successful collaborations, marketing tactics, and the use of technology like AI in the fashion industry. In this part of the conversation, Ramy Brook Sharp discusses the use of AI technology in the fashion industry, the growth and future plans for Ramy Brook, and the potential for expansion into new product categories and markets. She also talks about the importance of the team and the role of her husband in the financial aspect of the business. The conversation concludes with a rapid-fire round of questions.

Takeaways

·     Ramy Brook is a fashion brand known for its sexy, silky tops and contemporary price point.

·     The company has a balanced approach to sales, with about 50% of revenue coming from wholesale and 50% from e-commerce.

·     Successful collaborations with jewelry designers, shoe brands, and activewear companies have helped expand Ramy Brook's product offerings and reach new customers.

·     Marketing efforts focus on social media platforms like Facebook and Instagram, as well as influencer partnerships and traditional digital marketing.

·     The use of AI technology, such as Raspberry AI, is being explored to improve design iterations and speed up the production process. AI technology can save time and improve the process in the fashion industry, particularly in areas like photo shoots and design decisions.

·     Ramy Brook is focused on slow and steady growth, with plans to expand the team in design and sales.

·     The brand is exploring new product categories such as jewelry and accessories.

·     International expansion is a key area of growth for Ramy Brook.

·     The company is considering opening brick-and-mortar stores in strategic locations.

·     Ramy Brook admires designers Donna Karan and Diane von Furstenberg and would like to meet Taylor Swift.

Chapters

00:00

Introduction and Catching Up

02:47

The Growth of Ramy Brook: From Sexy Tops to a Full Collection

06:15

Balancing Wholesale and E-commerce: Ramy Brook's Sales Strategy

10:24

Successful Collaborations: Expanding Ramy Brook's Product Offerings

15:06

Marketing Tactics: Social Media, Influencers, and Digital Advertising

26:17

The Impact of AI Technology in the Fashion Industry

28:13

Growth and Future Plans for Ramy Brook

31:43

Exploring New Product Categories and Markets

37:12

The Importance of the Team and Financial Oversight

38:21

Potential Expansion into Brick-and-Mortar Stores

42:23

Rapid-Fire Round: Celebrity Guests, Favorite Designers, and More

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In this episode of The Retail Pilot, Ken sits down with the brilliant mind behind Solo Brands, John Merris, a prominent disruptor in the retail industry. John brings a wealth of knowledge and experience to the table, sharing invaluable strategies for achieving profitability in both direct-to-consumer (DTC) and wholesale channels.

This episode delves into the fascinating world of retail entrepreneurship and the challenges faced by emerging brands seeking to establish a strong foothold in today's competitive market. Tune in as John offers unique insights and actionable advice, honed through years of hands-on experience, on how to effectively navigate the intricacies of DTC and wholesale operations.

During this engaging conversation, Ken and John explore the critical factors that drive success in DTC sales, from building an engaging online presence to optimizing customer acquisition and retention.

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Join Host Ken Pilot for an Exclusive Interview with Steve Madden: The Visionary Behind the Iconic Footwear and Accessories Brand

Key Highlights:

Steve Madden's Early Career Steve Madden's journey in retail began at a shoe store in Cedarhurst, Long Island. By leveraging his connection as Johnny Madden's little brother, he secured a job that marked the start of his illustrious career in the shoe business.

Creative Influence in the Shoe Business During the mid-'70s, Steve worked in an era marked by creative trends, especially in men's footwear like platform shoes. Inspired by the store owner who fancied himself a shoe designer, Steve's passion for the creative side of the shoe business blossomed.

Mentorship at Gildor At Gildor, a renowned shoe retailer, Steve found a mentor in Larry, the owner's son. Larry's emphasis on perfect displays and attention to detail profoundly influenced Steve's approach to business.

The Influence of Sobriety Steve credits his sobriety as a pivotal factor in his success. Getting sober allowed him to focus and make better business decisions, ultimately driving his achievements.

Impact of Jordan Belfort Steve's association with Jordan Belfort, the infamous "Wolf of Wall Street," had mixed consequences. While Jordan's entrepreneurial spirit encouraged Steve, their financial dealings led to legal troubles and Steve's imprisonment. Despite this, Steve acknowledges Jordan's impact on his journey.

Appreciation for Teamwork Steve highlights the importance of a strong team, crediting his success to the people around him. His childhood friend, Jamie Carson, played a crucial role as CEO during Steve's absence, protecting the company during challenging times.

International Business Steve's brother, John Madden, significantly contributed to the international expansion of Steve Madden. John's charm and relationship-building skills complemented Steve's hands-on business approach. Today, the brand operates in approximately 50 countries, advocating for international trade as a means to foster mutual understanding and peace.

The Steve Madden Group The Steve Madden Group owns several notable brands, including Betsey Johnson, Dolce Vita, BB Dakota, Big Buddha, Blondo, and Greats. Steve Madden remains open to further acquisitions, particularly in the apparel sector, with a focus on good management and innovative ideas.

Steve Madden: The Man Behind the Brand Steve Madden is an award-winning designer and entrepreneur whose company is valued at over $3 billion. Despite facing significant challenges, including addiction and legal troubles, he has built a global empire through resilience and creativity.

In 1990, with just $1,100, Madden launched his brand, anticipating consumer needs and delivering cutting-edge collections. His Queens-based factory quickly transformed his dream into reality, giving birth to the Steve Madden brand.

Today, with over 200 stores worldwide, numerous brand acquisitions, and collaborations with stars like Sydney Sweeney, Cardi B, and Kendall and Kylie Jenner, Steve Madden continues to innovate and lead the industry.

Steve's humble beginnings and the support he received are never far from his mind. As a recovering addict and someone managing ADD, he actively supports organizations that offer second chances.

A native New Yorker, Steve resides in Manhattan with his children and remains deeply involved in his company's operations, from Long Island City headquarters to showrooms and stores worldwide.

Don't miss this insightful conversation with Steve Madden, an entrepreneurial icon who turned a small investment into a global powerhouse, inspiring millions with his creativity, resilience, and dedication.

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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, join Ken as he sits down with retail legend, Mindy Grossman.

Mindy Grossman is a highly accomplished businesswoman who has held leadership positions in companies such as HSN, Nike and Weight Watchers. Her innovative approaches to retail and marketing have earned her numerous accolades throughout her career.

Tune in to hear Ken and Mindy explore Mindy's journey to success, the challenges she's faced along the way, and the lessons she's learned that can inspire listeners to achieve their own goals.

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Ken Pilot interviews Mindy Grossman, a return guest to The Retail Pilot Podcast.

Mindy Grossman is a Partner and Vice Chair at Consello, a financial services advisory and strategic investing platform.

Prior to Consello, Mindy joined Weight Watchers in 2017 as the CEO and President leading the repositioning and rebranding of the company to WW Intl. From 2008 to 2017 Mindy took IAC retail public and then became CEO of HSN, a $4B DTC business. Earlier in her career, Mindy had key Leadership roles with Nike, Ralph Lauren, Warnaco, Tommy Hilfiger and and Oxford industries.

Mindy has been recognized and awarded numerous times over her career including Forbes Magazine’s The 100 Most Powerful Women, an Advisory role on President Obama’s Digital Economy board as well as serving as chairman of the NRF.

Mindy currently is an investor in and on The Board of Directors of Herself Health and Fanatics, Inc., VF, American Heart Association and HungryRoot.

Summary

Mindy Grossman discusses the diverse services provided by the company and the role her team plays with major companies. She highlights the importance of customization and collaboration in their advisory practices. Mindy also talks about the investments made by Consello Capital in tech-enabled services and consumer retail. She emphasizes the power of storytelling in business and the need for brands to create authentic and engaging experiences for customers. Mindy shares her passion for education and her involvement in various non-profit organizations. She reflects on her favorite moments in her professional career, including starting a business, leading the apparel business at Nike, and her time at HSNI.

Takeaways

·     Consello provides a diverse range of advisory and investment services to major companies, with a focus on customization and collaboration.

·     Investments made by Consello Capital are centered around tech-enabled services and consumer retail.

·     Storytelling is a powerful tool in business, allowing brands to create authentic and engaging experiences for customers.

·     Mindy Grossman is passionate about education and is involved in various non-profit organizations.

·     Her favorite moments in her professional career include starting a business, leading the apparel business at Nike, and her time at HSNI.

Chapters

00:00

Introduction and Overview of Consello Group

03:10

Customized Advisory and Investment Services

09:53

Investments in Tech-Enabled Services and Consumer Retail

13:07

The Power of Storytelling in Business

23:57

Favorite Moments in Mindy Grossman's Professional Career

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Ken interviews Chris Riccobono, Co-Founder and Executive Chairman of Untuckit., one of the fastest-growing men’s retail brands in the U.S.

After earning his Bachelor’s degree from Providence College in 2001, Chris began his career at GE Healthcare and enrolled in Columbia Business School in 2007. While working towards his MBA, Chris thought of the idea for UNTUCKit after speaking with lots of men about their fit problems—especially the length of their collared shirts—and began the business from his apartment in Hoboken. It began as just a side job, but once Chris and his early customers realized that he’d solved a big problem in men’s fashion, the business quickly grew beyond his expectations—with a compound annual growth rate over 100% each year—into the brand we know today with more than 50 retail locations by the end of 2018 and an entrance into the international market.

In addition to furthering his education and growing the brand, Chris dedicated time to sharing his passion for wine through a video blog called Pardon That Vine, traveling the world interviewing winemakers, and teaching beginners about wine. Chris was a winner of the Entrepreneur Of The Year® 2018 Award in New York and in his spare time he works closely with the Cancer Center at Atlantic Health System in New Jersey.

Chris currently lives in New Jersey with his wife and children.

1. Untuckit's Origin and Chris Riccobono's Journey: Chris Riccobono, the co-founder of Untuckit, started the company with the idea of creating a shirt designed to be worn untucked, addressing a common problem in men's fashion. The concept emerged from Chris's frustration with traditional shirts being too long, and he decided to venture into the fashion industry despite having no prior experience in the field.
2. Struggles and Early Challenges: Untuckit faced initial challenges, including the difficulty of finding the right shirt length and manufacturing issues. They encountered setbacks like shirts shrinking and buttons unraveling. Chris and his partner struggled to make a quality product and initially had limited resources, raising a modest amount of money to launch the brand.
3. Marketing Strategies and Growth: Untuckit adopted unconventional marketing strategies, such as radio ads and airline ads, to promote their unique product. The tagline "shirts designed to be worn untucked" resonated well with the audience. Despite the slow initial growth, Untuckit's brand strength and customer satisfaction led to significant success, with a focus on brick-and-mortar stores alongside online presence.
4. Impact of the COVID-19 Pandemic: The podcast covers the unexpected challenges Untuckit faced during the COVID-19 pandemic. The company went from a position of rapid growth to considering bankruptcy within a few months. Chris highlights the importance of resilience and adaptability in overcoming the challenges posed by the pandemic, which significantly impacted the fashion industry.
5. Current and Future Plans: Despite the challenges, Untuckit managed to survive and adapt. Chris discusses their recovery strategy, including negotiating with landlords and factories, raising debt, and ultimately becoming profitable again. Untuckit is optimistic about the future, planning to open 20-25 stores, exploring international markets, and diversifying into wholesale. The company aims to continue its growth trajectory and capitalize on its brand strength.
6. Efficient Store Strategy: Chris emphasizes the importance of efficient store design and operations. He prefers stores in the range of 1,200 to 1,500 square feet, with a focus on cost-effective buildouts. The goal is to provide a productive and efficient shopping experience.
7. Move Away from Large, Expensive Stores: Chris challenges the tradition...

Ken Pilot interviews Dave Powers, Presidet & CEO of Deckers Brands, a global footwear and apparel company based in Santa Barbara, Calif.

His current role includes prioritizing strategic initiatives and investments to expand the global distribution footprint of Deckers Brands, while also ensuring consumers have a seamless experience when engaging directly with each channel or brand. He focuses on long-term growth and Omni Channel strategies for the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®.

Since 2012, Dave has served in various roles at Deckers Brands, including spearheading growth initiatives for the company’s brand portfolio as President of Brands and leading direct-to-consumer strategies as President of Direct-to-Consumer.

Dave is passionate about consumer-led insight and innovation as well as doing great in business and doing good for people and the planet. His passion for innovation as well as improvement led by consumer insight has resulted in gains in operating margin and revenue. Dave also remains committed to sustainability as well as making a positive societal impact and leading a strong company culture.

Under his leadership as President & CEO since 2016, Deckers Brands has received accolades for stellar financial performance and sustainability efforts. In 2019, Deckers was selected by Investor's Business Daily® as one of the 50 Best ESG Companies: A List of Today's Top Stocks For Environmental, Social and Governance Values. The company was also recognized by Footwear News as 2020 Company of the Year for its financial performance and commitment to diversity, equity and inclusion as well as significant charitable giving for COVID-19 relief. Most recently, in 2023, Deckers was named on Newsweek’s list of America’s Greenest Companies and Just Capital’s Most Just Companies list.

In 2020, Dave was named a 2020 Businessperson of the Year by Fortune, ranking number 13 on their list of top executives. Dave also ranked on the list of Barron’s Top CEOs of 2023.

Dave has over twenty years of experience in merchandising, concept development and leadership of global retail operations at some of the industry’s top brands. Prior to joining Deckers Brands, he held executive leadership roles at Converse, including four years as Vice President of Global Direct-to-Consumer where he successfully guided the expansion of the brand globally, and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel.

A native of New Hampshire, Dave graduated Cum Laude from Northeastern University with a bachelor’s degree in marketing. Now residing in Santa Barbara, Calif., he enjoys spending time outdoors with his wife and two sons.

Some Key Takeaways of the Podcast Episode are:

1.    Career Evolution: Dave Powers began his career journey with a background in designing apparel and marketing. He transitioned from a rough patch working odd jobs to eventually joining Levi's and later the Gap. His experience ranged from starting in the stores to moving up the ladder, gaining valuable knowledge in merchandising, apparel, and visual marketing.

2.    Transition to Footwear: Despite not considering himself a footwear guru initially, Dave found his p...

Ken interviews Co-Founders of Negative, Marissa Vosper and Lauren Schwab.

Lauren Schwab co-founded Negative in 2014 alongside Marissa Vosper with no experience in the fashion and manufacturing industry. With a passionate belief that women deserved to love the garments closest to their skin, Lauren taught herself every stage of developing, fitting and producing beautiful and functional intimate apparel. Prior to Negative, Lauren started her career in finance, working at two globally recognized investment management firms. Lauren was selected as one of WWD's 40 Under 40 list of industry notables who are changing the face of retail, fashion and the beauty industry. She graduated from the University of Pennsylvania with degrees in Art History and Diplomatic History. When she isn't working on Negative, she loves spending time with her husband and 3 little kids.

Marissa Vosper was born and raised in Boulder, CO. She attended the University of Pennsylvania, earning degrees in Political Science and Spanish Language. After establishing her early career in branding, she co-founded Negative in 2014 alongside Lauren Schwab. Within the company, Marissa is focused on all aspects of brand strategy, communications, marketing, web and customer experience. Prior to Negative, she worked at two large branding agencies for a variety of clients, including Fortune 500 corporations, fashion labels, luxury brands and start-up businesses. She was honored as part of the Forbes 30 Under 30 List of Entrepreneurs for Art & Style. Marissa currently resides in New York City with her husband and 3 sons.

Key takeaways from this episode include:

1.    Inspiration Behind Negative Underwear: Marissa and Lauren were inspired to start Negative Underwear after recognizing a gap in the market for high-quality, minimalist lingerie. Dissatisfied with the options available, they embarked on a four-year journey from concept to launch, conducting market research and product development while maintaining full-time jobs.

2.    Differentiation in the Market: Negative Underwear aimed to distinguish itself by offering a product that combined high-quality raw materials sourced from European heritage mills with an accessible price point through a direct-to-consumer model. The founders identified a lack of options between luxurious, but expensive, brands and mass-market, poorly made options, positioning Negative Underwear in a unique space.

3.    Strategic Naming and Branding: The name "Negative" was chosen to reflect the brand's commitment to minimalism and a direct, provocative appeal. The founders wanted to stand out from other lingerie brands that often had French or girly names. The name embodied their vision of creating a straightforward, American brand that challenged existing norms in the lingerie market.

4.    Self-Funding and Growth Philosophy: Negative Underwear has achieved substantial growth without external funding. Marissa and Lauren emphasize the importance of sustainable and thoughtful growth, drawing parallels to iconic brands that built their success over time. They prioritize making a superior product and focus on creating brand allegiance through a methodical and customer-centric approach.

5.    Future Growth Opportunities: While the brand has primarily focused on direct-to-consumer sales, the founders acknowledge the potential for growth in various channels, including wholesale, retail, and even exploring platforms like Amazon. Despite having experimented with pop-ups and partnerships in the past, their lean approach allows themto adapt quickly to new opportunities, leaving the door open for potential expansion.

6.    Lean Team and Profitability: Negative has maintained a lean team with around 15 full-time employees, emphasizing a disciplined and profitabl...

Enjoy a replay of this beloved episode of The Retail Pilot podcast.

In this episode, Ken sits down with Ryan Babenzien, the brilliant mind behind Greats, a renowned footwear brand that has taken the industry by storm. But today, Ryan is here to share his latest venture: Jolie, a groundbreaking showerhead filter brand.

Join Ken as he delves into Ryan's entrepreneurial journey, from building a successful sneaker empire to tackling a new frontier in personal care.

Discover the inspiration behind Jolie and how Ryan's passion for sustainability and wellness led him to revolutionize the way we experience showers.

Key Takeaways from this podcast include:

· Career Path and Transition to Retail: Ryan initially studied economics and considered a career in finance but pivoted to entertainment, eventually transitioning to retail. His experience in entertainment, where he represented celebrity talent and advised brands on product placement, honed his marketing skills and influenced his later ventures in retail and brand building.

· Founding Greats and Its Success: Babenzian founded Greats, the first digitally native footwear brand, in 2014. His knowledge of footwear and the direct-to-consumer (D2C) model contributed to its rapid success. Greats was sold to Steve Madden in 2019. This venture taught him valuable lessons in brand building and the challenges of online businesses involving products with sizing.

· Jolie Skin Co's Innovative Approach: Inspired by the inefficiencies he observed with products that have sizing, Babenzian founded Jolie Skin Co, focusing on water purity for better skin, hair, and well-being. Jolie offers a subscription-based model with a showerhead that includes a filter to purify water, addressing contaminants that can harm skin and hair.

· Marketing and Growth Strategy: Jolie's growth strategy heavily relies on user-generated content (UGC) and organic marketing. Instead of spending heavily on paid advertising, they focused on influencer marketing at a micro level, leading to 5,000 pieces of UGC in their first year. This grassroots approach has been pivotal in creating a strong community and driving efficient, profitable growth.

· Efficient Business Model and Future Outlook: Jolie became profitable within six months, aided by its subscription model and low churn rate. With a small team of three full-time employees and several contract partners, they have efficiently scaled the business, projecting significant growth. Babenzian aims for a strategic exit within 36 months, building on the lessons from his first entrepreneurial venture and maintaining a clear focus on profitability and sustainable growth.

· Importance of Multi-Channel Distribution: Ryan emphasizes that relying solely on direct-to-consumer (D2C) sales is not sustainable due to the high costs of digital marketing. He advocates for a diverse retail strategy, which includes being in various retail channels and marketplaces like hair salons, Goop, Erewhon, Home Depot, and Target. This diversified approach helps in maintaining profitability and reaching a broader customer base.

· Direct-to-Consumer Still Dominates: Despite the emphasis on multi-channel distribution, over 90% of Jolie's business remains direct-to-consumer. This channel is profitable from the first purchase, highlighting its importance to the company. Additionally, 15% of their top line comes from Amazon, showcasing the significance of leveraging well-established digital marketplaces.

· Potential Retail Expansion: Ryan mentions the possibility of Jolie opening its own retail stores in the future, with innovative concepts like high-tech vending machines and small, productive retail spaces. This would enhance brand presence and provide customers with a unique shopping...

This episode of The Retail Pilot - Tech Talk - features Ken Pilot's interview with Joe Yakuel, Co-Founder & CEO of brkfst.io, and three of his customers.

Soumya Sriraman is an experienced CEO and general manager with deep expertise in building streaming businesses across a variety of media companies. She most recently led Qurate Retail Group’s streaming commerce business, which includes the QVC+ and HSN+ and previous to that she led the Amazon channels business.

Stephen Simonis is a strategic advisor, investor and mentor to many leading CPG brands, and is currently Chief Revenue Officer at The Beard Club.

Cezanne Huq is A veteran marketer and product strategist and brings nearly 27 years of management, product and digital marketing experience leading in-house and agency teams domestically and globally for large-scale brands. Most recently, Cezanne led the digital teams for HelloFresh, Molekule, Lifelock, Intuit and Experian.

In this podcast interview, we learn about how brkfst.io helps brands create authentic content tailored to audience and platform. Receive hundreds of UGC video ads from over 5,000 content creators within 3 weeks.

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Ken Pilot interviews Terry Lundgren for this flight of The Retail Pilot - Leaders & Legends.

Terry Lundgren served for 14 years as CEO of Macy’s, Inc., operator of Macy’s, Bloomingdale’s, Bluemercury and one of the largest retail ecommerce businesses in America. He retired from Macy’s, Inc. in January 2018 after serving for 10 months as the company’s Executive Chairman. Prior to becoming CEO of the company in February 2003 and Chairman and CEO in January 2004, Lundgren had been President and Chief Merchandising Officer since May 1997. 

He is the founder of the Terry J. Lundgren Center for Retail at the University of Arizona where he hosts an annual conference for retail industry leaders and students interested in a career in retail and related industries.

Lundgren currently serves on the boards of The Procter & Gamble Company, New DataNetwork, and the Economic Club of New York. He is a former board member of Kraft Foods Inc. the Federal Reserve Bank of New York, Carnegie Hall and has participated in numerous charitable and civic efforts. He has served as co-chairman of the Partnership for New York City and the American Heart Association CEO Roundtable, and as chairman of the National Retail Federation (twice), National Minority Supplier Development Council, and the American Society of Corporate Executives. Lundgren also currently serves as an Executive In Residence at Columbia Business School.

Key Takeaways from Ken's conversation with Terry include:

Terry Lundgren's Career Journey: Terry Lundgren started his retail career at Bullocks Department Store, which is now Macy's, and worked his way up to become the CEO of Neiman Marcus at the age of 37. Later, he played a key role in the acquisition and transformation of Federated Department Stores into Macy's Inc.

Mentorship and Influential Figures: Alan Questrom, a prominent figure in the retail industry, was a significant mentor for Terry Lundgren. Questrom's guidance and influence played a crucial role in Lundgren's career decisions, including taking a lower-paying job at Bullocks, which eventually led to his successful career.

Strategic Acquisitions at Macy's: Lundgren orchestrated major acquisitions at Macy's, including the purchase of Marshall Field and the acquisition of May Company. These strategic moves were aimed at expanding Macy's into a national brand and increasing its market presence.

E-commerce Initiatives and Early Adoption: Lundgren recognized the potential of e-commerce early on and supported the development of online platforms at Macy's, leveraging the expertise of teams in Silicon Valley. Despite challenges, including the dot-com bust in 2000, Macy's continued to invest in e-commerce, establishing a significant lead over competitors.

Challenges Facing the Retail Industry Today: Lundgren identifies three major challenges for retailers:

• Overcapacity of Physical Retail Space: There is an excess of physical retail space, and the industry needs to adapt by reducing store numbers.
• Potential Consumer Spending Slowdown: With a potential decline in consumer spending, especially among middle and lower-income households, retailers may face economic headwinds.
• Department Store Positioning: Department stores need to differentiate themselves to stay relevant. Lundgren advises a focus on offering unique products and enhancing the shopping experience to give consumers a reason to choose Macy's over other options.

Department Stores' Future: Terry Lundgren believes that department stores will continue to exist in the future. He emphasizes the importance of adapting to the changing retail landscape by providing differentiated reasons for customers to choose one department store over another.

...

Ken Pilot conducts his second interview with Chris Burch, Founder of Burch Creative Capital, for this episode of The Retail Pilot.

· Diverse Business Ventures: Chris Burch's company, Burch Creative Capital, is actively involved in multiple industries including hotels, real estate development, prefab building, technology, and retail. He highlights an innovative project in Boston where they are constructing low-income housing using prefabricated materials in collaboration with the Public Housing Authority.

· Prefab Housing Innovation: A significant project discussed is the construction of an 11-story building with 240 apartments using prefabricated materials. This method improves quality control, speeds up construction, and is beneficial for workers. The project, named Lab 9, is unique and has potential for expansion.

· Hotel and Hospitality: Burch's hotel, Nihi, off the coast of Bali, has received numerous accolades and is known for its unique, community-focused experience. Burch is expanding his hospitality ventures with a new project in Costa Rica, emphasizing authentic experiences and community involvement.

· Green Lane Salad Chain: Burch introduced a new salad chain, Green Lane, offering fresh, affordable salads through a drive-through model. The business has received positive feedback and is expanding rapidly with plans to roll out more locations. The chain maintains a focus on value, quality, and customer satisfaction.

· Fashion Industry Involvement: Burch is involved in several fashion brands, including STAUD, Rowing Blazers, Danielle Guizio, and Solid and Striped. Each brand is at different stages of growth or turnaround, with a focus on affordability and customer engagement. Burch emphasizes the importance of operational efficiency and strategic pricing in the fashion industry.

· Investment Philosophy and Approach: Chris Burch invests in businesses with momentum and potential for significant growth. He prefers to partner with businesses, offering not just capital but also operational expertise, which gives him an edge over traditional private equity funds. He looks for companies with demand and potential, even if they are currently struggling, like Rowing Blazers, which had strong brand perception but was facing operational challenges.

· Involvement and Value Addition: Burch's level of involvement varies depending on the needs of the business. He can provide strategic vision or get into detailed operational aspects if necessary. He emphasizes the importance of building a solid management team and working directly with entrepreneurs to maximize business potential.

· Preference for Control and Strategic Planning: Burch prefers to have significant control over the businesses he invests in, avoiding situations where board control could impede his influence. He focuses on long-term strategic planning, aiming to envision where the business will be in ten years and working towards that vision.

· Vision for New Ventures: Burch is interested in integrating supply chain and luxury experiences into new markets, particularly in housing, hotels, and hospitality. He is exploring the development of a new, unique hotel concept in Hialeah, blending luxury, entertainment, and wellness. He believes the future of hospitality lies in creating spaces that offer both high-energy entertainment and serene relaxation.

· Lessons Learned and Investment Criteria: Over his career, Burch has learned the importance of separating emotionality from investment decisions and the critical role of hiring competent CEOs. He tends to sell his investments early, which has been both a benefit for peace of mind and a potential downside in terms of missed growth opportunities. He looks for substantial stakes in companies, p...

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Join Ken as he sits down with Brian Berger, Founder & CEO of Mack Weldon, a leading menswear brand that has taken the industry by storm.

With a focus on design, performance and functionality, Mack Weldon offers a specialty line of underwear, socks and t-shirts that has garnered a loyal following among men worldwide.

Brian brings over a decade of experience in the digital world to his role at Mack Weldon, having served in leadership positions at Comcast, WebMD and Excite@Home.

Tune in to this episode to learn more about Brian's journey in the world of retail and discover how he has built Mack Weldon into the success story it is today. 

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Ken Pilot interviews Sid and Ann Mashburn, Founders of Sid Mashburn and Ann Mashburn, for this episode of The Retail Pilot Podcast.

Sid Mashburn grew up in small-town Mississippi but began his design career in New York in the mid-1980s, as J.Crew’s first men’s designer. He designed the brand’s first heritage piece— the Barn Jacket. He was later recruited by Ralph Lauren to join the design team at Polo, and after subsequent stints leading design at Tommy Hilfiger and Lands’ End, it was time to do his own thing. His wife, Ann Mashburn had been on the editorial side of fashion, working in magazines at Condé Nast (Vogue, Glamour) and then as a stylist at J.Crew. Since meeting in their early 20s, they’d known that whether it was making mix tapes or throwing parties, what they really loved wasn’t just creating things, but sharing them with others.

Summary

Sid and Anne Mashburn discuss their journey in building their retail business, which includes six stores and an online presence. They emphasize the importance of creating a unique and personalized shopping experience for their customers, with a focus on customer service and curated merchandise. They also talk about the challenges they faced in launching their business and the decision to expand into online sales. The conversation touches on the significance of the tailor shop in their stores and the success of their made-to-measure business.

Ann Mashburn discusses the importance of the experience and memory associated with buying and wearing clothing. She emphasizes the value of made-to-measure clothing and the attention to detail it requires. Ann also talks about the role of marketing in reaching customers and reinforcing the brand. She mentions the use of digital marketing and email campaigns as effective strategies.

Ann and Sid Mashburn discuss the challenges and benefits of working together as a married couple. They highlight the importance of trust and the support they provide each other. They also mention their mentors and the inspiration they draw from different designers and places. Ann and Sid share their vision for the future of their business, including expanding to more cities and growing their e-commerce presence. They emphasize the importance of creating special experiences for every customer and maintaining a sense of restraint in their growth. Finally, they discuss the value of personal connections and relationships in their industry.

Takeaways

·     Creating a unique and personalized shopping experience is key to building a successful retail business.

·     Customer service and curated merchandise are important factors in attracting and retaining customers.

·     Expanding into online sales can be a significant growth opportunity for brick-and-mortar retailers.

·     The tailor shop adds a bespoke element to the store and enhances the overall customer experience.

·     The made-to-measure business allows for a deeper level of customer engagement and satisfaction. The experience and memory associated with buying and wearing clothing can be just as important as the clothing itself.

·     Made-to-measure clothing offers a personalized and high-quality experience for customers.

·     Digital marketing and email campaigns are effective strategies for reaching and engaging customers.

·     Working together as a married couple requires trust and support.

·     Mentors and relationships with industry professionals can provide valuable advice and guidance.

·     Creating special experiences for every customer is a key focus for the business.

·     Maintaining a sense of restraint and thoughtful growth is important for long-term success.

·     Personal connections and relationships are highly valued in the industry.

Chapters

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Ken speaks with Lori Coulter, Co-Founder and CEO of Summersalt, on this Flight of The Retail Pilot - Leaders & Legends.

Lori Coulter is the Co-Founder and CEO of Summersalt, a generation-defining lifestyle brand known for its data-backed fit and designer quality products without the designer price tag. In 2020, she was named one of Inc. Magazine’s Top 100 Female Founders.

Lori and her Co-founder, Reshma Chattaram Chamberlin, launched Summersalt to change the conversation around swimwear and address a true market gap by creating designer swimwear without the designer price tag. Summersalt’s product is data-backed with 1.5 million measurements taken from 10,000 women’s body scans.

From day one, Summersalt knew it wouldn't stop at swimwear. The first challenge was to transform the swimwear shopping experience from being intimidating and vulnerable to fun and empowering. Quickly, Summersalt expanded to include adventure-friendly essentials that help make every aspect of a woman's wardrobe more joyful and comfortable—from sleepwear to intimates to activewear. Named one of the Top 100 Upstarts in the world by CNBC, The Lead’s Breakout Company of the Year, and Fast Company’s Brands That Matter in 2022, the brand has seen exceptional growth and consumer adoption, garnering praise from leading outlets including Vogue, Elle, CNN and Forbes.

Prior to launching Summersalt, Lori, a veteran start-up founder with deep expertise in design, supply chain and ecommerce, launched one of the first mass customization startups at the intersection of technology, fashion and data to incorporate body scanning and made-to-order manufacturing.

Lori holds a Master of Business Administration from Washington University in St. Louis and a Bachelor of Business Administration from Baylor University. She serves on the Board of Trustees at her alma mater Washington University in St. Louis and champions inclusive economic development and entrepreneurship as a member of the University’s Skandalaris Center National Council. Outside of Summersalt, Lori enjoys spending time with her husband and two sons, and exploring the world through her love of travel and adventure.

Key takeaways from this episode are:

1.    Customer-Centric Approach: Lori Coulter emphasizes the importance of understanding and meeting the needs of the consumer. From the early stages, they focused on creating swimwear that empowered women to feel confident and engage with life. Their emphasis on fit, inclusivity, and sustainability reflects their commitment to their customers' values and preferences.

2.    Direct-to-Consumer Success: Summersalt's success largely stems from its direct-to-consumer business model. By bypassing traditional retail channels and selling directly to customers online, they maintain a closer connection with their audience and have more control over their brand experience. This approach allowed them to optimize fit based on real-time feedback and manage returns effectively.

3.    Strategic Partnerships and Collaborations: Summersalt leverages strategic partnerships and collaborations to expand its reach and grow its brand. They've collaborated with major retailers and plan to continue doing so, utilizing physical retail spaces alongside their online presence to reach a wider audience.

4.    Adaptability and Resilience: The company demonstrated adaptability and resilience, particularly during challenging times such as the COVID-19 pandemic. Despite facing a significant drop in revenue, they managed to bounce back and even thrive by tapping into consumer demand for swimwear and leveraging their online presence.

5.    Holistic Marketing Strategy...

Ken Pilot interviews Simeon Siegel, MD and Senior Analyst, Retail & eCommerce for BMO Capital Markets, for this Flight of The Retail Pilot Podcast

Overview: In this episode, leading retail analyst Simeon Siegel returns to discuss the current state of the retail sector, emphasizing the importance of execution in a challenging economic environment.

• Key Topics: Simeon's Role: Simeon explains his work as a retail analyst, helping investors understand which companies are performing well and which are struggling. He covers 20-30 companies and provides ratings such as outperform, underperform, and market perform.
• Current Retail Climate: The year has been progressively challenging for retail, with lingering effects from the pandemic. While some sectors are struggling, others are thriving, highlighting a divergence between winners and losers in the market.
• Luxury Market Trends: The luxury sector is experiencing pressure for the first time in years, with growth slowing from 8% to 4%. Despite this, some brands like Prada and Hermes continue to perform well.
• Execution Matters: The conversation emphasizes that execution is key in today's market. Companies that adapt and perform well are gaining market share, while larger, established brands face challenges.
• Consumer Health: Despite concerns about credit card debt and inflation, the U.S. consumer remains resilient. Retailers need to balance promotions and marketing to maintain brand value while driving sales.
• Technology Investments: As retailers navigate challenges, there is a focus on investing in technology that enhances both online and in-store experiences. The importance of inventory management and customer engagement is highlighted.
• Winners in Retail: Companies like TJX are noted for their strong performance due to their unique value propositions for both consumers and vendors. Other brands showing potential include Nike, despite recent struggles.

Conclusion: The episode wraps up with reflections on the evolving retail landscape, emphasizing the need for brands to adapt strategically to maintain relevance and profitability amidst changing consumer behaviors and economic conditions.

Listen for More: Tune in for deeper insights into retail trends and expert analysis from Simeon Siegel!

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In this episode of the Retail Pilot Podcast, Ken Pilot engages with retail legend Mickey Drexler, discussing the current state of retail, pricing trends, and the importance of customer experience. Drexler shares insights from his journey at Alex Mill, emphasizing the significance of quality, team dynamics, and the evolving landscape of retail. The conversation also features Ali Dillon, the President of Alex Mill, Alex Drexler, Founder, and Creative Director, Somsack Sikhounmuong, who discuss their roles and the brand's vision, highlighting the importance of community and innovative marketing strategies.

Key Takeaways Include:

Recent Success: Alex Mill has experienced strong sales performance attributed to changes in merchandising and management.

Product Focus: Sweaters and denim are particularly successful categories for Alex Mill, with emphasis on fit and quality.

Retail Strategy: Alex Mill follows a "less is more" approach, focusing on smaller store sizes and selective expansion.

Marketing Channels: Instagram is a primary driver of brand awareness, with the company also exploring TikTok marketing.

Expansion Plans: Alex Mill is planning to open a new store in Rockefeller Center, aiming for an early November launch.

Customer Acquisition: Word-of-mouth marketing plays a crucial role in the brand's growth and recognition.

Product Diversity: Mickey emphasizes the importance of offering multiple color options for key items to create visual impact and customer appeal. Sustainability and reworking products can also create new opportunities.

Team Dynamics: A strong, diverse team is critical for successful product execution and business operations.

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Ken Pilot interviews Shai Eisenman, CEO and Founder of Bubble, on this episode of The Retail Pilot Podcast. Bubble Skincare is the first modern, affordable, science-backed skincare line formulated to clean, balance and hydrate young skin all for under $20. Today, the Bubble line consists of 20+ products that work together to create a complete routine from face cleansers to face masks. Bubble products are available on hellobubble.com, in over 16,000 retail locations across the US, Austrailia and the UK including Boots, Beauty Bay, CVS Walmart and Ulta stores.

Prior to starting Bubble in 2018, Eisenman started her B.A. at 15, and began her career in business at 16 years old. She lives in New York with her partner and two children. 

Key Points:

• Shai started Bubble after an early start in academics and entrepreneurship
• Bubble focuses on affordable, high-quality skincare products for younger consumers
• The company built a community of 4,600 Gen Z advisors before launching
• Bubble now has over 50,000 brand ambassadors who provide input on all decisions
• Products are priced affordably (around $15) but with prestige-level quality
• Initially launched D2C but quickly pivoted to retail partnerships
• Now available in 13,000 U.S. stores including Walmart, Ulta, CVS, and Amazon
• Recently expanded to the UK (Boots) and Australia (Priceline)

Business Strategy:

• Focused on margin dollars rather than margin percentage
• Found retail partnerships more profitable than D2C for their price point
• Invests in physical experiences and grassroots marketing over traditional advertising
• Collaborates with brands like Disney to reach new audiences
• Raised capital primarily from individuals and early-stage funds
• Aims to be profitable and not reliant on external funding

Community Engagement:

• Uses multiple platforms to communicate with brand ambassadors
• Offers gift cards and commissions to ambassadors
• Runs college campus programs with exclusive merchandise
• Involves community in product development, naming, and marketing decisions

Challenges and Growth:

• Adapting leadership style and operations as the company scales
• Expanding internationally while remaining an independent brand
• Balancing control over brand experience with benefits of retail partnerships

Leadership Insights:

• Values building a strong team and fostering community
• Relies on experienced advisors for guidance in different growth stages
• Emphasizes the importance of adapting to different business stages

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Ken interviews Matt Mueller, Founder and CEO of Knot Standard, the leader in premium custom menswear in the United States. Matt has been one of the most pivotal figures behind tech innovation in menswear over the last decade, creating the unique, AI-powered Style Wall and Fit App for Knot Standard, and holding numerous other patents. He has a 25-year record in global business and technology, having worked with firms such as the Advisory Board Company, Gannett, Harvard, and Dubai Holding. Beyond his professional successes, Matt is the extremely proud father of his five young children, and holds a degree in Finance from the McIntire School of Commerce at the University of Virginia where he is also a Guest Lecturer. When he is not simultaneously working on Knot Standard or advising new startups, Matt and his family enjoy traveling around the globe.

Key Takeaways of the Podcast Include:

1.    Matt, the CEO of Kot Standard, is a pioneer in tech innovation for menswear. He has over 25 years of experience in global business and technology, and has played a pivotal role in developing AI-powered style solutions for menswear.

2.    Kot Standard started as an online-only custom clothing brand based in Dubai. They focused on providing confidence through well-fitting, custom-made clothing. Over time, they expanded their offerings and entered the brick-and-mortar space with successful store openings.

3.    Technology has been a crucial component of Knot Standard's success. They developed in-house measuring apps and integrated ordering and supply chain systems, which enabled them to efficiently produce custom clothing without the need for extensive inventory.

4.    During the COVID-19 pandemic, Knot Standard introduced virtual appointments, which turned out to be a critical move for their survival. These virtual appointments, along with their technology-driven approach, allowed them to adapt and thrive in a challenging retail landscape.

5.    Knot Standard's innovative business model is now being extended to partnerships with established brands. They have partnered with retailers like Brooks Brothers and Nordstrom, leveraging their technology to offer custom clothing solutions within existing stores. This approach minimizes inventory risks and provides a new revenue stream for the partner brands.

6.    Knot Standard is exploring international expansion, considering opportunities in global markets. They believe that their technology-driven, custom clothing platform can be successfully replicated in various regions around the world.

7.    Business Growth: In the last 18 months, Knot Standard has experienced significant growth, particularly with partnerships like Nordstrom and Brooks Brothers. They now cover about $25 million in annual orders, with half of that coming from their online platform and the other half from physical stores.

8.    Revenue Sources: Approximately 25% of Knot Standard's revenue comes from software and wholesale installations. This is a significant portion of their overall business, and it is expected to grow in the coming years.

9.    Store Performance: Knot Standard's own stores have been performing exceptionally well, with an average four-wall EBITDA of 32%. This is significantly higher than industry averages, indicating the success of their approach to retail.

10. Funding and Investment: Knot Standard has raised approximately $35 million in funding to support their growth. Their lead investor is a group called Provenance, which recognized the value of the brand's loyal customer base and high-end purchase behavior.

11. Competition and Differentiation: Knot Standard sees its competition as not just ot...

Ken Pilot interviews Alex and Mike Faherty, co-founders and leaders of eponymous apparel brand, Faherty for this episode of The Retail Pilot. 

Alex is a co-founder and CEO at Faherty. Prior to starting at Faherty, Alex spent over a decade in Investment Banking and Private Equity. Formerly a football player at Yale, Alex takes a coaching mentality in how he runs the business, knowing that so much of a brand's success is who makes up the team. When he has time, and isn't coaching T-ball, he likes to surf.

Mike wrote his college essay about starting Faherty Brand, going on to major in Fashion Design at Washington University in St. Louis before spending a decade in New York’s fashion industry. His passion is sourcing high-quality fabrics from around the world and developing innovative new ones himself. Mike loves playing basketball and finding off-the-beaten-track surf spots and restaurants.

 Key Highlights:

1. Faherty has had a successful business with Australian tourists in the States, as the brand resonates well with English-speaking customers. They're planning to expand further, starting with a partner in Australia.

2. Retail store growth is seen as a valuable way to capture customers, as it allows them to experience the brand in person and make a more significant commitment to the higher-priced products.

3. The founders emphasize the authenticity of retail stores, as customers can't be deceived by appearances, and they have to genuinely like the products.

4. Faherty is focused on finding unique, interesting locations for its retail stores, rather than following a cookie-cutter approach. They look for underserved areas with potential customers.

5. Catalogs have been an important acquisition channel for Faherty since 2015. They are looking to evolve the catalog experience to stand out and feel more like a magazine or coffee table book.

6. Faherty is shifting its approach to social media, aiming to create platform-specific content for various channels. They recognize the need to adapt to changing social media trends.

7. The founders discuss their tech stack, highlighting platforms like Shopify for e-commerce and New Store for POS. They also use NetSuite for ERP and have implemented in-house tech solutions for design and development.

8. Faherty is exploring how AI can enhance the customer experience, especially in terms of managing inbound and outbound communications efficiently.

9. One of the challenges for Faherty is ensuring that as the brand grows, it still feels intimate and special to consumers, rather than becoming too corporate or generic.

10. Mike emphasizes the importance of refining the sampling process using AI to ensure that only the most promising designs move forward, reducing sample expenses.

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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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Join your host Ken Pilot in this episode of The Retail Pilot, as he sits down with Marc Metrick, the driving force behind the transformative journey of luxury retail giant Saks Fifth Avenue. From his early days at Saks to his pivotal role in the acquisition and integration of the iconic brand, Marc takes us through a captivating tale of strategic evolution and reinvention.

Learn how Marc's visionary leadership led to a critical juncture in 2019, as Saks embarked on a groundbreaking split into two distinct entities. He unveils the motivations behind this move, detailing the challenges and opportunities it presented. Marc's insightful narrative shines a light on the redefined hierarchy of KPIs, talent acquisition, and resource prioritization that formed the bedrock of Saks' digital-first transformation.

Marc's unique perspective on owning the IP, controlling pricing and promotion, and the symbiotic relationship between the e-commerce and stores arms of Saks will leave you with a deep appreciation for the intricacies of luxury retail management.

Join us as we dive into Marc Metrick's journey, unveiling the secrets behind Saks Fifth Avenue's evolution into a modern-day retail powerhouse.

If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

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A THROWBACK to one of our earlier episodes of The Retail Pilot podcast with Andy Dunn, Founder of Bonobos and Author of Burn Rate.

In this compelling episode, Ken sits down with Andy Dunn, a renowned entrepreneur and co-founder of the game-changing men's clothing brand, Bonobos. However, the conversation goes beyond Andy's professional accomplishments, as Andy delves into a deeply personal and significant aspect of his life: his journey with mental health and bipolar disorder and how it lead to crafting his memoir, Burn Rate.

Listen as Andy bravely shares his experiences, offering a candid and enlightening perspective on the intersection of entrepreneurship and mental well-being. In a society that often glorifies the hustle and overlooks the challenges entrepreneurs face behind the scenes, Andy's story serves as a reminder that success doesn't always come without its struggles.

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Ken interviews Nick Graham, CEO of SPACEONE Industries and Founder and Chief Underpants Officer of Joe Boxer. Nick Graham changed the face of fashion when he turned his underwear company into one of America¹s most popular lifestyle brands. Graham coined the phrase "The Brand is the Amusement Park, the Product is the Souvenir” and uses this philosophy in everything he does.

Graham was the first clothing designer on the internet in 1992, did the first live-streaming fashion show with Microsoft from an airplane hangar in Iceland and in 1998 installed the world’s largest e-mail in New York’s Times Square. He holds the record for the highest point a pair of underwear has been alone, (120,000 feet by single thrust rocket), and the unofficial record for the Worlds Fastest Fashion Show, (1.2 seconds by Human Cannonball).

He staged the first transatlantic runway show 30,000 feet above Greenland with his friend Richard Branson, and is currently collaborating with Bill Nye the Science Guy.

Currently Graham is the CEO of SPACEONE Industries that designs and produces space inspired consumer products for Men, Women and Children and is distributed through better department stores in the United States. The company also produces products for private space companies including Blue Origin, and Axiom to name a few. Graham has collaborated with many numerous space initiatives over his career including being major sponsor of the 50th Anniversary of Apollo 11 at Kennedy Space Center, launching Virgin Galactic with Richard Branson and having Apollo 11 astronaut Buzz Aldrin and Science Guy Bill Nye walk in his Men’s fashion show called “Life On Mars” at New York Fashion Week.

1.    Building Personal Relationships in Business: The conversation between Ken and Nick highlights the importance of personal connections in business relationships. Despite the professional setting, their banter shows a long-standing friendship, emphasizing the significance of personal rapport in business dealings.

2.    Entrepreneurial Journey: Nick Graham's journey from designing ties to founding Joe Boxer illustrates the entrepreneurial spirit and the unpredictable paths that lead to success. From humble beginnings to significant brand launches, his story underscores the importance of seizing opportunities and embracing creativity.

3.    Branding and Marketing Strategy: Nick Graham's approach to branding emphasizes emotional engagement and storytelling. His philosophy that "the brand is the amusement park and the product is the souvenir" encapsulates the idea of creating an emotional connection with consumers, transcending the mere transactional aspect of purchasing.

4.    Innovation and Adaptation: The evolution of Joe Boxer, from its inception to its collaborations with major retailers like Macy's and Kmart, demonstrates the importance of innovation and adaptation in staying relevant in the market. Nick's willingness to pivot and explore new ventures, such as his foray into fragrance and consulting with JCPenney, underscores the entrepreneurial mindset needed for sustained success.

5.    Community and Brand Loyalty: The discussion touches upon the significance of building a community around a brand and fostering brand loyalty. Nick highlights the importance of understanding and speaking to the target audience, creating a sense of belonging, and fostering brand evangelism among consumers. This underscores the idea that successful brands go beyond selling products; they create a lifestyle and communitythat resonates with their audience.

6.    Humor and Emotional Connection in Branding: Nick Graham emphasizes the importance of incorporating humor, irony, and a sense of fun into brand design to create emotional connections with customers. He believes that this approach sets his b...

On this flight of The Retail PIlot, Ken Pilot interviews Pete Nordstrom, the President and Chief Brand Officer of Nordstrom. Throughout his career, Pete has helped Nordstrom innovate the customer shopping experience and redefine the role fashion plays in customers’ lives leading major strategic initiatives such as building the designer offering to a $1.5 billion business, evolving Nordstrom’s mix of brands and categories and bringing in limited distribution brands as exclusive partners.  

Since taking over leadership of Nordstrom in 2000, Pete and his brothers grew the business from $5.1 billion to $15.1 billion, increased the number of stores by more than 200 locations and opened Nordstrom’s first flagship store in New York City as an experiential shopping destination. Driven by a Nordstrom principle to “leave it better than we found it,” they also led the organization to achieve 100 percent pay equity for employees, earn a spot on Fortune 100 Best Companies to Work For list for 20 years in a row and set a target to give back more than $50 million in local communities where we do business by 2025.  

Key takeaways from this podcast episode include:

1.    Early Introduction to Retail: Pete Nordstrom's entry into the family business started at a young age, with his father emphasizing the importance of work during summers. He began working at Nordstrom at the age of 12, starting with simple tasks like sweeping and stock work in the shoe department.

2.    Career Progression: Nordstrom's career at the company progressed from selling shoes at age 16 to various managerial roles, including store manager and regional manager. He followed a typical career path within the company, starting from entry-level positions and gradually moving up through the ranks.

3.    Family Business Dynamics: Nordstrom discussed the dynamics of being part of a multi-generational family business. He shared insights into the transition of leadership within the company, including his own experience when he and his brothers were given the opportunity to lead after a change in leadership.

4.    Customer Service and Brand Building: Nordstrom emphasized the importance of customer service and adapting to changes in consumer preferences. He discussed Nordstrom's commitment to providing exceptional service while also recognizing the shift in customer expectations towards speed and convenience, particularly in the digital age. Additionally, Nordstrom highlighted the company's approach to brand partnerships and its focus on amplifying brands' presence through strategic collaborations.

5.    Adaptation to E-commerce: Nordstrom acknowledged the evolution of retail, particularly with the rise of e-commerce. He discussed how Nordstrom adapted to the changing landscape by not only maintaining its renowned customer service but also by embracing online channels and forming partnerships with direct-to-consumer (DTC)brands to reach a broader audience.

6.    Changing Business Models: Pete Nordstrom highlights the evolving nature of business relationships, moving from traditional wholesale models to more flexible arrangements. He emphasizes the importance of solving customer needs while discussing various financial arrangements with brands.

7.    Diversification in Retail: The discussion explores the shift from traditional retail models to omnichannel approaches. Nordstrom discusses the integration of physical stores and online platforms, emphasizing the importance of reaching customers through multiple channels.

8.    Partnerships and Discovery: Nordstrom emphasizes the value of partnerships with brands and the importance of maintaining a spirit of partnership rather than transactional relationships. He also highlights the role of platforms like marketplaces in...

In this episode of The Retail Pilot, host Ken Pilot sits down first in a Pre-Flight conversation with Simeon Siegel, Senior Retail Analyst for BMO Capital Markets, to discuss the state of the Retail market both post-election and leading into the holiday season.

For the main Flight, Ken speaks with Rachelle Hruska MacPherson, founder of the fashion brand Lingua Franca. Rachelle shares the unexpected journey that led her to create a company known for its hand-embroidered cashmere sweaters and socially conscious messaging.

Origins of Lingua Franca

• Rachelle started the company unexpectedly in 2016 while dealing with stress from her previous business
• The idea came from embroidering "booyah" on an old sweater as a therapeutic exercise
• Early success came from a viral "I Miss Barack" sweater after the 2016 election

Business Growth and Model

• Lingua Franca offers custom embroidery on cashmere and cotton items
• The company has expanded into ready-to-wear clothing and collaborations
• Current revenue is under $30 million, with 60-70% from direct-to-consumer sales

Product and Pricing

• Cashmere sweaters with embroidery retail for around $380
• Cotton items start at $150, opening up a new market segment
• Custom embroidery is available in stores and through an online customizer

Marketing and Collaborations

• Growth has been largely organic, with minimal traditional marketing
• Collaborations with celebrities, artists, and brands have been key to expansion
• Upcoming collaborations include Wicked and Gilmore Girls

Challenges and Future Plans

• Rachelle discusses the difficulties of scaling while maintaining brand authenticity
• She emphasizes the importance of product quality and customer service
• The company is exploring new marketing strategies, including digital advertising

Personal Insights

• Rachelle shares her favorite travel destinations and TV shows
• She discusses the importance of mentorship and community in the fashion industry

The episode provides an in-depth look at how Lingua Franca has grown from a personal project into a socially conscious fashion brand, navigating the challenges of scaling while maintaining its core values and unique positioning in the market.

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Ken Pilot interviews Scott Tannen, Founder and CEO of Boll & Branch on this flight of The Retail Pilot Podcast.

Scott Tannen is the CEO and Founder of Boll & Branch, the world’s leading luxury bedding brand, which he founded in 2014 with his wife Missy Tannen. 

Boll & Branch was one of the earliest direct-to-consumer brands in the soft home world of bed and bath products, and is the first ever 100% organic Fair Trade Certified™ bedding company. Every product, from their sheets to their down pillows, is made sustainably, with a transparent supply chain, and today Boll & Branch is one of the largest e-commerce-first luxury home brands, loved by millions of Americans, including every living US president, and countless celebrities. 

Scott started his career at Nabisco / Kraft Foods, and was pivotal in the strategic development and modernization of communication efforts for brands including Altoids, Oreo, Planters, Milk-Bone, Life Savers and dozens of others. During his time with the conglomerate, he also oversaw Digital communications and marketing for Kraft Foods entire portfolio of Nabisco Cookies & Crackers, Confections and Snacks brands. He later went on to join Wrigley, establishing the digital division for their global portfolio of brands, including Orbit, 5 Gum, Juicy Fruit, Life Savers, and others. Prior to Co-Founding Boll & Branch, Scott was the Founder & President of Candystand.com, which he launched in 2008 and sold to Publisher’s Clearing House in 2010.

Scott’s work has been recognized by the advertising and creative industry with awards including Gold and Bronze Clios, Effies and Cannes Lions. He sits on the advisory boards of several technology and consumer goods companies, and is a Vanderbilt University alum. Scott resides in New Jersey with his wife Missy, their three children, and two dogs.

Summary

Boll & Branch is a leading luxury linens and bedding company that focuses on transparency, traceability, and sustainability in its supply chain. The founders, Scott and Missy Tannen, started the company 10 years ago with no background in textiles, which gave them a unique advantage in reimagining how the industry operates. They have built a strong brand that values quality, authenticity, and customer trust. Boll & Branch started with a focus on sheets and bedding but has expanded into other categories like pillows and bath products. They aim to create a complete solution for the bedroom and bathroom. The company has been self-funded and profitable since its early years, allowing them to maintain control and focus on long-term sustainability. They recently raised capital to clean up their cap table and have a strong partnership with Elk Hatton, who invested $100 million in 2019. Boll & Branch has achieved a net revenue of around $200 million and continues to grow. They prioritize customer retention and emotional connection by providing traceability and transparency through their OriginTrack feature. The company is primarily direct-to-consumer but also has retail stores and partnerships with retailers like Nordstrom. Bowen Branch has dedicated spaces in Nordstrom and Bloomingdale's, with specific merchandising and fixturing. Wholesale is a small part of the business, with the majority of sales coming from direct-to-consumer channels. The decision to sell on Amazon is a defensive play to capture customers who search for brands on the platform. Bowen Branch aims to maintain a strong online presence while expanding its retail stores. The company offers bespoke services, such as custom manufacturing and interior design consultations. Marketing efforts focus on word-of-mouth, TV, influencers, social media, and print catalog. Bowen Branch positions itself at a higher price point, offering super...

On this episode of The Retail Pilot podcast, Ken speaks with Nick Green, Co-Founder & CEO of Thrive Market, a membership-based online platform that makes healthy and sustainable living easy and affordable to all. Nick launched Thrive 10 years ago shortly after graduating from Harvard.

The business has also been recognized as a leader in regenerative agriculture, carbon-neutral shipping, and Zero Waste operations, and in 2020 became the nation’s largest grocer to receive B Corp Certification.

Outside of Thrive Market, Nick lives in Venice, CA with his wife, Carolina, and their three children.

Key Points

About Thrive Market: An online retailer offering natural and organic products at affordable prices through a membership model1

Mission: Making healthy and sustainable living easy, affordable, and accessible to all1

Business Model: $60 annual membership fee

• Curated assortment of natural and organic products
• AI-powered personalization
• Zero-waste fulfillment and carbon-neutral shipping

Company Stats

• Founded: 10 years ago
• Members: 1.5 million
• Annual Sales: Over half a billion dollars
• Profitability: Now profitable and cash flow positive1

Nick Green's Background

• Grew up in Minneapolis with a health-conscious mother
• Previously founded and sold an education company
• Met co-founder Gunnar, who grew up on a hippie commune

Business Strategy

• Product Mix: 90% third-party brands
• 10% Thrive Market branded products (generating 25% of sales)
• Private Label Strategy: Focus on filling gaps in the catalog rather than copying existing products1
• Margin Profile: Strong margins on both private label and third-party products
• Sustainability: Zero-waste fulfillment centers, carbon-neutral shipping

Marketing Strategy

• Referrals: 25% of new members come from existing member referrals
• Influencer Marketing: Unique approach to partnerships
• Digital Marketing: Leveraging technology for personalized experiences

Future Outlook

• Focus on expanding online presence rather than immediate brick-and-mortar plans
• Potential for future physical stores, but not a current priority
• Continued investment in AI and personalization technologies

Competitive Advantage

• Purpose-built for healthy living
• Membership model driving profitability and customer behavior
• Technology-first approach to e-commerce
• Strong focus on sustainability and ethical supply chains

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Ken Pilot interviews Tim Parr, CEO & Founder of Caddis, for this flight of The Retail Pilot podcast.

Tim Parr is the CEO and Founder of CADDIS, an eyewear brand that crushes age stereotypes. He believes in defying our society’s addiction to youth and fueling getting older and owning it. Tim is an entrepreneur who has also worked for some of the most respected brands. Patagonia, L.L. Bean, Filson. Tim has lectured at the Stanford School of Design, Modern Elder Academy, San Francisco Academy of Art, and the California College of Arts. In 2013 he formed a bluegrass band and hit the road touring the Western United States.

Summary

Tim Parr, the founder of CADDIS, shares his journey of starting a lifestyle brand focused on eyewear for people over the age of 40. He discusses the broken customer experience in the eyewear market and the opportunity to create a brand that is authentic and transparent. Tim emphasizes the importance of owning one's age and challenges the ageism prevalent in society. He also talks about the size of the 50+ demographic and the potential for growth in the market. Tim shares his approach to marketing, including the use of in-person experiences and tangible materials like catalogs. He highlights the significance of strong design, brand position, and storytelling in attracting customers. Tim also mentions his mentors and the challenges of maintaining innovation and creativity in the business.

Takeaways

• The eyewear market for people over the age of 40 has a broken customer experience, creating an opportunity for a brand like CADDIS to provide authentic and transparent products.
• Owning one's age is a powerful message that resonates with the 50+ demographic, which controls a significant portion of household income and spending power.
• In-person experiences and tangible materials like catalogs can be effective marketing tools for a lifestyle brand, allowing customers to connect with the brand on a deeper level.
• Strong design, brand position, and storytelling are essential for attracting customers and building a successful brand.
• Having mentors, both male and female, can provide valuable guidance and support in building a business.
• Maintaining innovation and creativity is a challenge for leaders, but it is crucial for the long-term success of a brand.

Chapters

00:00

Introduction and Tim's Journey

04:04

Identifying the 40+ Market for Eyewear

06:02

The Origin and Importance of the CADIS Name

07:15

Owning Your Age and Challenging Ageism

10:53

The Size and Potential of the 50+ Demographic

14:18

Elevating the CADIS Brand and Attracting Celebrities

19:24

Differentiating from Competitors like Warby Parker

21:47

The Importance of Authenticity and Creativity in Marketing

25:58

The Role of Tangible Marketing in Connecting with Customers

26:05

Tim's Role as CEO and Leadership Challenges

29:04

Margins and Product Manufacturing

32:11

Advice for Tim's Past Self and Lessons Learned

34:30

Mentors and the Importance of Innovation and Creativity

36:23

Rapid Fire Questions

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In this episode of The Retail Pilot, host Ken Pilot welcomes Jan Rogers Kniffen, CEO of J Rogers Kniffen Worldwide and retail industry expert, to discuss the current state and future of retail. Key Topics Discussed: Post-Election Retail Bounce

• Jan predicts a post-election retail bounce, as seen in previous presidential election years
• Discretionary retail is currently running at zero inflation, making it attractive to consumers

Fourth Quarter Outlook

• Despite potential headwinds, Jan expects a strong fourth quarter
• Forecasts 3.5-4% sales growth, similar to last year
• Believes discretionary goods will perform well due to their perceived value compared to inflating services

Walmart vs. Target

• Walmart is outperforming Target significantly
• Walmart is attracting higher-income customers, traditionally Target's demographic
• Walmart's focus on in-store experience and competitive pricing is paying off

Off-Price Retail Sector

• TJ Maxx ranked as the fifth-best retailer in America by Jan
• Concerns about over-saturation in the off-price sector
• Potential challenges for off-price retailers as the market matures

Department Store Future

• Predicts most department stores will go private by the end of 2026
• Cites lower interest rates and increased real estate values as factors facilitating buyouts
• Mentions Nordstrom, Macy's, and Kohl's as potential candidates for privatization

Tariffs and Manufacturing

• Discussion on the impact of potential tariffs, especially on goods from China
• Many retailers have already reduced their exposure to Chinese manufacturing
• Predicts that moderate tariff increases might be absorbed by Chinese manufacturers rather than passed on to consumers

Notable Quotes:

"May the bounce be with you." - Jan Rogers Kniffen on the post-election retail bounce

"I think it's come down to who can do this stuff as opposed to where you happen to be." - Jan Rogers Kniffen on retail performance

Closing Thoughts:

Jan expresses optimism for the retail sector going into the fourth quarter and 2025, despite potential challenges. He emphasizes the importance of execution and adaptation in the evolving retail landscape.

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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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Ken Pilot interviews Alexandra Wilkis Wilson for this episode of The Retail Pilot podcast.

Alexandra is an ENTREPRENEUR, INVESTOR & BOARD DIRECTOR.

She is best known as Co-Founder of ecommerce sensation, Gilt, which grew to $650M+ within 5 years of its launch and later sold to Hudson’s Bay Corporation. She was also Co-Founder of GLAMSQUAD, and Fitz, a closet organizing and styling company, which sold to Tradesy the peer-to-peer luxury recommerce company.

Today, Alexandra is Co-Founder and Managing Partner of growth equity fund, Clerisy, investing in consumer and techsumer companies. She has been an avid angel investor and advisor to over 80 consumer tech companies including Rent the Runway, The Mirror and Bubble. Alexandra is an active champion of female founders and the co-author of New York Times bestseller, “By Invitation Only: How We Built Gilt and Changed the Way Millions Shop”.

Summary

Alexandra discusses her entrepreneurial journey, starting with her time at Gilt and later founding Glamsquad. She shares the challenges and successes of both ventures and the lessons she learned along the way. She also talks about her involvement in other startups and her decision to join Clerisy, a growth equity fund. Alexandra discusses her career journey, the founding of Clerisy Partners, and their investment strategy. She highlights the importance of understanding consumer needs and solving problems in a unique way. Wilson emphasizes the hands-on approach of Clerisy Partners, where they actively partner with portfolio companies and provide support beyond capital. She also shares her leadership philosophy, the influence of mentor Mindy Grossman.

Takeaways

Alexandra Wilkis Wilson had an entrepreneurial spirit from a young age and pursued a career in investment banking before venturing into the world of retail and entrepreneurship.

Gilt, founded in 2007, grew rapidly and became a successful online luxury fashion retailer, attracting a large customer base with its timed sales and curated assortments.

Glam Squad, founded by Alexandra Wilkis Wilson, offered in-home beauty services and expanded to multiple markets, providing a hyper-local experience.

Alexandra Wilkis Wilson applied the lessons learned from Gilt to Glam Squad, including managing people, motivating teams, and giving and receiving feedback.

She later worked on other ventures, including Dressr, an app that used AI and machine learning to help users style outfits, and FITS, a service that organized consumers' closets and provided styling recommendations.

Alexandra Wilkis Wilson joined Clerisy, a growth equity fund, to continue her involvement in the tech and consumer-focused industry. Understanding consumer needs and solving problems in a unique way is key to successful investments.

Clerisy Partners takes a hands-on approach and actively partners with portfolio companies.

Delivering tough messages and providing constructive feedback is important for effective leadership.

Mindy Grossman has been a mentor and role model for Alexandra Wilkis Wilson.

Favorite streaming shows include El Tiempo Entre Costuras, Fauda, and Outlander.

Favorite vacation destinations are Key Biscayne and Brazil.

Taylor Swift is someone Alexandra Wilkis Wilson would love to meet.

Clerisy Partners aims to invest in the next unicorn among their portfolio companies.

Chapters

00:00

Introduction and Background

02:36

The Attraction to Gilt

05:34

The Early Vision and Success of Gilt

09:02

Gilt's Journey to Unicorn Status

12:07

Challenges and Exit of Gilt

15:29

Glam Squad: Inception and Expansion

18:44

Lessons Learned and Next Ventures

23:22

Dresser and FITS: Innovative Ventur...

In this episode of The Retail Pilot - Tech Talk, Ken Pilot speaks with Vic Drabicky and Josh Krepon about performance marketing in the Retail/Fashion Industry.

Summary

In this conversation, Vic Drabicky, CEO and founder of January Digital, and Josh Krepon, President of US D2C and Global Digital at Steve Madden, discuss the current state of performance marketing and the importance of balancing algorithmic marketing with inspirational and influential marketing. They also touch on the challenges of creating and managing content, the role of video in marketing, and the rise of TikTok shops. The conversation covers various topics related to retail and marketing, including the impact of consumer behavior shifts, the role of video commerce, the importance of collaborations and influencers, the use of MarTech in loyalty and data management, and the potential impact of the election on the retail environment.

Key Takeaways

• Performance marketing has dominated the marketing landscape in the past decade, but brands now need to find a balance between algorithmic marketing and inspirational/influential marketing.
• Creating and managing content can be challenging, and brands need to strike a balance between volume and quality.
• Video marketing is becoming increasingly important, and brands need to adapt to the changing landscape of platforms like TikTok.
• The rise of TikTok shops and partnerships with platforms like Amazon indicate that video commerce is on the horizon. Consumer behavior takes time to shift, and it may not always align with predictions or trends.
• Video commerce is a growing trend, but it may take a long time for people to change their behaviors and adopt it on a large scale.
• Collaborations and partnerships with influencers or other brands can be successful if they are authentic, aligned with the brand's values, and provide value to the customers.
• MarTech tools can be used for retention and loyalty programs, as well as data management and analysis.
• The outcome of the election can impact the retail environment, with consistency and confidence being important factors for stability and growth.

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To kick off The Retail Pilot podcast, Ken sat down with Millard "Mickey" Drexler, Chairman of Alex Mill. Come along for the ride as Ken and Mickey discuss his legendary career building brands and leading companies such as Ann Taylor, Gap, Old Navy, J.Crew, Madewell and now Alex Mill.

Ken's conversations with Mickey will be featured throughout three episodes exploring his journey through retail, running the business, and Mickey's favorite picks.

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On this Flight of The Retail Pilot Ken speaks with LEGEND, Tommy Hilfiger, Principal Designer, Tommy Hilfiger Global.

Uplifting and inspiring consumers since 1985, Tommy Hilfiger has pioneered one of the world’s most recognized premium lifestyle brands. With Hilfiger’s vision and leadership as Principal Designer, his eponymous brand celebrates the essence of classic American style with a modern twist. Tommy Hilfiger offers premium quality and value to consumers worldwide under the TOMMY HILFIGER and TOMMY JEANS lifestyles, with a breadth of collections including men’s, women’s and kids’ sportswear, denim, accessories, and footwear.

Hilfiger’s career in fashion began when he was a high school student in 1969 — opening his first store, People’s Place, in his hometown of Elmira, New York. A decade later, he moved to Manhattan to pursue a career in fashion design, before launching his namesake brand with a single menswear collection. Since then, global retail sales of TOMMY HILFIGER products have grown to reach approximately $9.1 billion in 2022, powered by more than 16,000 associates worldwide — present in 100 countries and more than 2,000 retail stores, including its largest global flagship store at tommy.com.

Hilfiger has a longstanding passion for philanthropy and making the world a better place for future generations. Through the global TommyCares organization, the brand supports various international initiatives and charities like Save the Children, the World Wildlife Fund and Fashion Minority Alliance. Hilfiger currently sits on the Board of Next for Autism. Through the Tommy Hilfiger Fashion Frontier Challenge and People’s Place Program, the brand is also making strides in its ambitious vision to create fashion that Wastes Nothing and Welcomes All – which actively focuses on topics such as social and environmental sustainability, diversity, and inclusivity in fashion and beyond.

Diverse achievements in business and fashion have earned Hilfiger numerous distinguished awards including the CFDA’s prestigious Geoffrey Beene Lifetime Achievement Award in 2012, British GQ’s Design Legend of the Year in 2020, BFC’s Outstanding Achievement Award in 2021 and WWD's John B. Fairchild Honor for Lifetime Achievement in 2022. Hilfiger’s life and career have been chronicled in his memoir, American Dreamer, published in November 2016 — reflecting his experiences in the fashion industry from the last 35-plus years. Recounting his early childhood and formative years, it explores the setbacks, triumphs, and sheer determination that drove him to build a multi-billion-dollar global brand.

Key takeaways from this interview include:

Tommy Hilfiger's Background: Tommy Hilfiger began his journey in retail and design at a young age, starting his own business at 18 years old by opening a retail store -People’s Place - selling jeans in 1969. This venture eventually led him to designing and creating products for his stores, culminating in the establishment of his own brand.

Innovative Store Concepts: Hilfiger's early stores, particularly People's Place, were not just retail outlets but cultural hubs influenced by music and fashion. They offered a variety of products, hosted band practices, and provided an immersive experience for customers, aligning with the youth culture of the time.

Cultural Influences on Brand Identity: Hilfiger aimed to differentiate his brand from traditional preppy styles by infusing it with elements of music, particularly hip-hop, and embracing a more inclusive approach to fashion. This cultural fusion helped establish the personality of the Tommy Hilfiger brand.

Disruptive Advertising Strategy: The Hangman ad campaign, conceived by advertising executive George Lois, was a bold and disruptive move that garnered attention for the brand. Despite...

Join Ken as he delves into Sandra's remarkable journey, exploring her early experiences, challenges faced, and the transformative moments that shaped her into the formidable leader she is today. Sandra's personal and professional triumphs provide valuable insights and inspiration for aspiring Latinx entrepreneurs seeking to make their mark.

During the conversation, Sandra opens up about her roots and the cultural values that have shaped her perspective on business and leadership.

Sandra is widely recognized for her exceptional leadership skills and her ability to navigate the complex world of fashion and retail. She shares her experiences as a former CEO and industry executive, shedding light on the unique challenges faced by Latinx professionals in these competitive sectors. Sandra's expertise and keen business acumen offer practical advice for Latinx entrepreneurs and women looking to break barriers and achieve success in any industry.

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Discover the story behind Indochino's rise to prominence and how CEO Drew Green and his team have revolutionized the way men approach their personal style. Listen in as Ken and Drew explore the company's commitment to craftsmanship, attention to detail, and the seamless blending of traditional tailoring techniques with modern technology.

Tune in to gain valuable industry insights from Drew's perspective and learn about the exciting future of custom men's clothing. Whether you're a fashion enthusiast, entrepreneur, or simply curious about the inner workings of a successful fashion brand, this episode will provide you with a captivating glimpse into the world of Indochino.

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Ken interviews three experts in Retail store staffing for the inaugural Tech Talk podcast episode.

Sharonda Weatherspoon is the SVP, Head of Retail Transformation, Client Development, and Operations, as well as the Co-Chair of North America's Diversity and Inclusion ERG. She has spent over 24 years at Ralph Lauren, surviving my tenure, and moving up through the ranks, starting as a General Manager, and in her most recent role, as SVP of retail stores from North America. Sharonda has always worked directly with the stores and fully understands the frontline experience where her focus has been to create the best customer experience and the appropriate staff to support it.

Ron Thurston is the founder of OSSY, a platform that aggregates store employee talent from sales associate to leadership roles, enabling retailers and brands to easily access Aussie's labor pool. Ron is also the author of the Amazon bestseller, Retail Pride, championing joy and success in the service industry. Ron's book draws on his experience and store leadership roles with Intermix, San Laurent, Tory Burch, Apple, West Elm, and Gap. Ron also hosts a podcast, Retail in America.

Mike Myers is the co-founder and CEO of Reflex and has spent the last decade building early stage companies as both a founder and an early stage venture. Reflex works with some of the top brands in retail today and helps brands leverage a flexible labor model to drive store performance. Retailers use Reflex to connect with experienced on-demand retail store associates and to flex their labor models to support the real time needs of the business.

Key Takeaways from this episode are:

1.    Evolution of Retail Staffing Post-COVID: The post-COVID environment has significantly changed the landscape of retail staffing. Retailers have had to adapt rapidly to evolving business models, leading to challenges in finding and retaining talent. Competing for local talent, dealing with the gig economy, upskilling rapidly, and identifying the right candidate profiles have become significant hurdles.

2.    Shift Towards On-Demand Flexible Talent: The emergence of platforms like Reflex has transformed the staffing model. They facilitate connecting retailers with on-demand, experienced retail talent, allowing for real-time staffing adjustments based on business needs rather than fixed hiring plans.

3.    Tech-Driven Recruitment Solutions: Reflex, as a tech platform, streamlines the staffing process. It provides a platform for retailers to access a pool of vetted workers for various roles, from back of house to front of house, offering flexibility in scheduling and facilitating worker-retailer feedback through ratings and reviews.

4.    Challenges and Benefits of Adopting New Staffing Models: Trust remains a significant obstacle for retailers adopting flexible staffing solutions like Reflex. However, the platform's benefits, including reducing turnover costs, addressing immediate staffing needs, and potential cost savings in comparison to traditional hiring and retention methods, make a compelling case for its adoption.

5.    Changing the Perception of Retail Jobs: The introduction of platforms like Ossy seeks to redefine the hiring process, especially for the retail workforce. It aims to replace traditional resumes with dynamic digital profiles, utilizing AI-driven algorithms to match candidates with suitable retail roles, focusing on soft skills, empathy, and curiosity, ultimately changing how individuals perceive and access retail job opportunities.

6.    Industry Insights through Trade Shows and Networking: Sharonda gains industry knowledge and stays updated by attending trade shows like NRF. and various others. Networking through LinkedIn and connections with individuals like...

Join Ken on this inspiring episode as he sits down with Deirdre Quinn, a trailblazing entrepreneur and the driving force behind the renowned fashion brand, Lafayette 148 New York, a brand and company built on passion, experience and love of the business. Deirdre's journey from a small start-up to an influential figure in the fashion industry is nothing short of extraordinary.

Deirdre Quinn's passion for empowering women is palpable in every aspect of her work. Throughout the episode, she shares her personal experiences and challenges faced while building her brand, shedding light on the significance of creating a supportive and inclusive environment for women in the fashion world. From her early days of working in a small loft to overseeing an international fashion empire, Deirdre's story is one of determination, resilience, and unwavering dedication.

Through Lafayette 148 New York, Deirdre has revolutionized the industry by offering sophisticated, luxurious clothing for the modern woman. With a commitment to craftsmanship, sustainability, and inclusivity, her brand has become synonymous with timeless elegance and impeccable quality. During the conversation, Deirdre delves into the creative process behind her designs, her vision for the future of fashion, and how she stays true to her brand's core values.

As a female leader in a predominantly male-dominated industry, Deirdre has become a beacon of inspiration for aspiring entrepreneurs and fashion enthusiasts alike. Her insights on leadership, gender equality, and the importance of nurturing talent are invaluable lessons for anyone seeking to make a mark in their respective fields. Her dedication to philanthropy and giving back to the community further showcases her commitment to creating a better world.

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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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Michelle Wlazlo joined JCPenney in March 2019 as executive vice president, chief merchandising officer, reporting to Marc Rosen, chief executive officer. Wlazlo is responsible for leading the Company’s global merchandise strategy and operations including Merchandising, Planning and Allocation, Pricing, Product Design, and Development and Sourcing.

Wlazlo brings more than 30 years of merchandising and stores experience from a variety of retailers. In her three years at JCPenney, she has led the charge in clarifying and defining the positioning of the Company’s private brands to give customers more choice. Wlazlo led the launch of Thereabouts, JCPenney’s most inclusive kid’s brand yet with adaptive apparel for children of all abilities; established JCPenney Beauty’s partnership with hero brand Thirteen Lune, providing a hyper-inclusive beauty experience; and led the introduction of Hope & Wonder, JCPenney’s new purpose-driven private brand, which celebrates festive holidays as well as important cultural moments and gives back to nonprofit partners, to life. Most recently, Wlazlo led the launch of JCPenney’s denim lifestyle brand for men, Mutual Weave.

Prior to joining JCPenney, she served as senior vice president, merchandising over apparel and accessories, baby gear and essentials at Target Corporation. Before Target, Wlazlo spent 19 years at GAP, Inc., in a variety of roles for Gap, Gap Outlet and Old Navy. She began her career at Saks Fifth Avenue, Inc., before assuming roles as store manager and buyer at Bebe Stores, Inc.

Wlazlo attended Lowthian College in Minneapolis and the Executive Education Program at Columbia University’s Graduate School of Business. She currently serves on the board of directors for the National Association for the Education of Young Children.

Key takeaways from this podcast interview include:

1.    Personal Journey to Retail: Michelle Wlazlo's journey into retail stemmed from a fascination and curiosity with shopping. Her experience working in her stepmom's store during high school ignited her passion for the industry, emphasizing the power of fashion and accessories to impact people's lives through simple transactions.

2.    Diverse Career at Gap Inc.: Wlazlo spent 19 years at Gap Inc., where she had the opportunity to work in various areas within the company. She specialized in turning around initiatives, launching new businesses, and bringing fresh perspectives to different divisions, demonstrating adaptability and problem-solving skills.

3.    Product Focus at JCPenney: Upon joining JCPenney, Wlazlo prioritized fixing the product assortment and driving clarity between brands. Recognizing the importance of good product, she emphasized the need to deliver quality and value to customers, focusing on improving the overall product experience.

4.    Partnership with CEO Mark Rosen: Wlazlo highlighted her strong working relationship with CEO Mark Rosen, describing their partnership as complementary and based on trust. They share a passion for product and have a similar taste level, learning from each other and maintaining open communication to drive the company forward.

5.    Inclusion and Private Label Strategy: JCPenney's focus on...

Ken Pilot interviews Mike Natenshon, Founder of Marine Layer, for this episode of The Retail Pilot Podcast.

Mike Natenshon started Marine Layer the day after his girlfriend threw away his favorite shirt. In the ensuing 10 years, Marine Layer has grown into a complete California-inspired lifestyle brand delivering new favorite shirts to wherever their customers are. Although considered 'digital first' Marine Layer operates 50 stores and two 1969 VW buses nationwide.

Summary

MarineLayer is a retail brand that started as an online t-shirt company and later expanded to brick-and-mortar stores. The company focuses on creating high-quality, comfortable clothing for men and women. They have a balanced distribution model, with 60% of sales coming from retail stores, 40% from direct-to-consumer online sales, and a small percentage from wholesale.

MarineLayer has been able to maintain profitability and grow steadily by taking a measured approach to expansion and focusing on building a strong brand. They have plans to continue growing all three distribution channels and are considering international expansion in the future.

Marine Layer is a brand that focuses on creating comfortable and casual clothing for both men and women. The stores are designed to feel like a room in your home, with a familiar and intimate atmosphere.

The company has a program called Respun, which is an upcycling initiative that collects old t-shirts and finds new uses for them. They offer customers a recycling bag and a credit towards future purchases.

In terms of marketing, Marine Layer uses paid social media advertising on platforms like Instagram and TikTok, as well as catalogs. They have also explored connected TV advertising but found it to be expensive and not as targeted as other channels.

In terms of technology, Marine Layer has invested in Endless Isle, which allows them to share inventory across channels and provide a seamless customer experience. They are also exploring the use of AI for customer analytics and predictive product merchandising.

As a leader, Mike is focused on protecting the company's culture and maintaining a fun and collaborative work environment. Marine Layer operates on a hybrid work model, with employees working three days in the office and two days remotely. Mike's favorite Marine Layer item is a t-shirt that he has worn for the births of both of his daughters.

Takeaways

• MarineLayer started as an online t-shirt company and later expanded to brick-and-mortar stores.
• They have a balanced distribution model, with 60% of sales from retail stores, 40% from online sales, and a small percentage from wholesale.
• The company focuses on creating high-quality, comfortable clothing for men and women.
• MarineLayer has been able to maintain profitability and grow steadily by taking a measured approach to expansion and focusing on building a strong brand.
• They have plans to continue growing all three distribution channels and are considering international expansion in the future. Marine Layer focuses on creating comfortable and casual clothing for both men and women.
• The stores are designed to feel like a room in your home, with a familiar and intimate atmosphere.
• Respun is Marine Layer's upcycling program that collects old t-shirts and finds new uses for them.
• Marine Layer uses paid social media advertising and catalogs for marketing.
• They have invested in technology like Endless Isle for seamless inventory management and are exploring the use of AI for customer analytics.
• Mike is focused on protecting the company's culture and maintaining a fun and collaborative work environment.
• Marine Layer operates on a hybrid work model, with employees working three days i...

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Dave Heath is the Co-Founder and Chief Executive Officer of Bombas. Prior to the launch in 2013, Dave dedicated two years to rigorous product testing and refinement to create the best performing and most comfortable sock available, while staying true to their mission of helping those in need. 

Dave holds a BA from Babson College with majors in Marketing, Management, and Entrepreneurship. Previously, he led business development as one of the founding employees at UrbanDaddy followed by joining the new media acquisitions and strategy team at Yucaipa Companies. As a true serial entrepreneur, Dave has founded three companies, with one successful exit, and has invested and consulted on a range of start-up businesses from concept, through launch and continued growth. Dave has been featured on ABC’s Shark Tank, NBC TODAY Show, CBS This Morning, ABC Good Morning America, Bloomberg TV and in The New York Times, and was named EY Entrepreneur of the Year in 2017.

In this episode of The Retail Pilot, Dave Heath joins Ken Pilot and discusses the journey of starting a mission-based sock company and the challenges and successes along the way. He shares insights on the importance of focus, sustainable growth, and using time to your advantage. Dave also talks about the power of partnerships and collaborations that align with Bombas' mission. He emphasizes the need for authenticity and staying true to the brand's values. Additionally, he discusses the role of technology in marketing and the future of the company. In this conversation, Dave Heath discusses the potential of AI in e-commerce and its application in various areas such as asset creation, site updates, and site merchandising. He also introduces Constructor, an AI-powered site merchandising tool. The conversation touches on the use of AI in customer service and the importance of understanding the customer experience. Additionally, Dave shares his favorite streamed shows and provides a promo code for Bombus products.

Key Takeaways from this episode of The Retail Pilot with Dave Heath, CEO of Bombas:

1.    Entrepreneurial Journey and Problem-Solving Approach: Dave Heath's journey began with a desire to work for himself, learning various skills and exploring different industries, always with the intent of eventually starting his own business. His approach was less about the industry and more about identifying and solving problems. He noticed the lack of socks in homeless shelters, leading him to start Bombas with a mission to donate a pair of socks for every pair sold.

2.    Socially Conscious Business Model: Bombas was established with a buy-one-give-one model, similar to TOMS Shoes, to address the significant need for socks in homeless communities. Over time, this model evolved to include not just socks but also underwear and t-shirts, the top three most requested clothing items at homeless shelters.

3.    Founding Team Dynamics: Dave Heath, along with co-founder Randy Goldberg and two others, formed a cohesive team where each member possessed specific skills that complemented one another. Their self-awareness of strengths and weaknesses helped them work effectively together, aligning their shared values and visions for the company's ethical growth.

4.    Sustainable Growth Strategy: Bombas adopted a deliberate, focused growth strategy rather than chasing rapid expansion. They avoided excessive fundraising and maintained profitability from the outset. They prioritized methodical growth, aiming for sustainability and quality over immediate scale. This approach allowed them to retain control and avoid unnecessary stress associated with continuously raising capital.

5.    Multi-Channel Distribution Strategy: Despite primarily being a direct-to-consumer (D2C) brand, Bombas strategically entered the wholes...

Throwing it back to the debut episode of The Retail Pilot, join your host Ken Pilot, as he embarks on an inspiring conversation with none other than Millard "Mickey" Drexler, the visionary Chairman of Alex Mill.

Buckle up as Ken and Mickey delve into the riveting tales that have shaped Mickey's illustrious career, leaving an indelible mark on the retail landscape. From his groundbreaking endeavors at Ann Taylor, Gap, and Old Navy to his iconic stewardship at J.Crew, Madewell, and now Alex Mill, Mickey's story is a testament to innovation, perseverance, and unmatched expertise.

If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

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1.    Todd Snyder's Background: Todd Snyder, a retail designer, grew up in Ames, Iowa, with a background in business. Despite his unconventional path, his passion for clothes and fashion ultimately led him to pursue a career in design.

2.    Early Fashion Influences: During his high school years, Todd admired designers such as Calvin Klein, Ralph Lauren, and Armani. However, as he transitioned into college and began working in retail (particularly selling Ralph Lauren's Polo clothing), his admiration for Ralph Lauren's work grew, solidifying his aspiration to become a designer.

3.    Early Retail Experience: Todd gained valuable experience in the retail industry, working at various stores in Iowa, including Yonkers and The Buckle. He also worked in a store called Bedowers, where he not only sold menswear but also worked in the tailor shop, sparking his interest in the process of creating clothing.

4.    Internship at Ralph Lauren: Todd's first significant step into the fashion industry was through an internship at Ralph Lauren. As an intern, he took on various tasks, ranging from fetching coffee to organizing the closet. This experience allowed him to make a positive impression and eventually led to freelance opportunities with the company.

5.    Transition to J.Crew: In 1993, Todd transitioned to J.Crew, a pivotal time for the company's growth. While at J.Crew, he contributed to the development and expansion of the business.

6.    Challenges of Running a Business Solo: Todd shares the difficulties he faced while self-funding his business, highlighting the limitations of personal credit and the need for external investment. He reflects on the pivotal moment when American Eagle approached him, providing an opportunity for growth.

7.    Transition from Wholesale to Direct-to-Consumer: Todd discusses the evolution of his business model, emphasizing the shift from primarily wholesaling to being almost entirely direct-to-consumer. He explains the challenges he faced with wholesale, such as differing seasonal schedules and SEO competition, and the benefits of focusing on direct customer engagement.

8.    Diverse Product Assortment and Customer Segmentation: Todd emphasizes his commitment to offering a wide range of products, from sweatshirts to tuxedos, to create a one-stop shopping experience for men. He also shares insights on customer segmentation and the importance of effectively managing a growing customer base.

9.    Marketing Strategies: Todd discusses the various marketing channels he utilizes, including influencer collaborations, affiliate partnerships, and social media advertising. He highlights the shift towards mobile-focused advertising and the challenges posed by recent iOS changes

10. Embracing Technology for Customer Engagement: Todd reveals his interest in implementing AI-driven tools to enhance customer experience. He expresses the importance of using technology, like CRM systems and AI, to predict and cater to customer preferences, providing a personalized shopping experience.

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Ken interviews Nyakio Grieco, Co-founder of Thirteen Lune and Founder of Relevant: Your Skin Seen on this flight of The Retail Pilot - Leaders & Legends.

Nyakio (pronounced Neh-Kay-Oh) Grieco is a beauty entrepreneur and advocate for clean, inclusive beauty that suits all skin types, tones, and needs. As a veteran beauty founder and trusted industry voice, Nyakio has launched successful businesses: her award-winning brand nyakioTM, based on her family’s Kenyan roots and beauty secrets that launched in 2002, and inclusive beauty e-commerce destination, Thirteen Lune, launched with cofounder Patrick Herning in 2020. Thirteen Lune launched as the first of its kind, e-commerce destination designed to inspire the discovery of beauty brands created by BIPOC founders that resonate with people of all colors. Thirteen Lune has since partnered with retailer JC Penney for inclusive beauty shop-in-shop locations in over 600 stores nationwide.

Continuing her commitment to inclusive beauty Nyakio created Relevant: Your Skin Seen, a clean, science-led skincare brand that works for all skin tones and types. Working with top labs to ensure a diverse mix of chemists, Nyakio formulated each product with superfruits and actives in efficacious percentages to create products that truly perform. Most recently, the brand expanded into the cosmetics category with six color and complexion products. All products in the range are formulated with skincare benefits and serve and celebrate every skin tone, while hyper prioritizing consumers who have been underserved.

Most recently, Nyakio Grieco has been honored with the CEW 2023 Female Founder Award, the Beauty Matter 2023 Future50 Award and included on the Inc. Magazine 2023 Female Founders 200 List.

Key takeaways from the interview include:

1.    Cultural Heritage and Beauty: Nyakio Grieco's journey into the beauty space was deeply influenced by her Kenyan heritage, particularly her grandmother's beauty secrets rooted in natural ingredients like coffee beans and sugar cane. This connection to her family's traditions and the use of earth-derived elements shaped her early interest in skincare.

2.    Transition from Entertainment to Beauty: Despite initially pursuing a career in sports and entertainment, Grieco found herself drawn to the beauty industry through her work with actresses and exposure to beauty products. She noticed a gap in the market for products celebrating Africa's rich resources and heritage, leading her to pivot her career towards beauty entrepreneurship.

3.    Challenges of Entrepreneurship: Grieco faced significant challenges as a black female founder, especially in accessing capital and navigating the beauty industry's landscape. Despite setbacks and failures, she persevered, leveraging mentorship, resourcefulness, and industry connections to keep her brand afloat and eventually succeed.

4.    Creation of ThirteenLune: Following the acquisition of her brand by Unilever, Grieco co-founded Thirteen Lune with Patrick Herning, aiming to create an inclusive beauty retail platform highlighting products by black and brown founders. The platform aims to debunk stereotypes and provide visibility for diverse beauty brands, challenging the notion that these products are only for specific demographics.

5.    Expansion and Future Vision: Despite the rapid growth of Thirteen Lune through partnerships with JCPenney and other retailers, Grieco remains focused on expanding the platform's direct-to-consumer presence and nurturing its brand identity. She sees opportunities for standalone stores, global expansion, and further development of their private label brand, Relevant. The goal is to continue championing diversity in the beauty industry while nurturing and growing the brands within the Thirteen Lune...

Ken interviews Simeon Siegel, Managing Director, Senior Analyst of Retail and eCommerce for BMO Capital Markets.

Key takeaways from the interview include:

1.    Role as an Equity Research Analyst: Simeon's job involves assessing publicly traded companies within the retail sector. He emphasizes the importance of being objective in his analysis, even if it means delivering hard truths that may not always be well-received by company stakeholders.

2.    Divergence in Retail Performance: Despite macroeconomic fears and media narratives about the decline of retail, Simeon highlights that many retail companies are performing well. He notes significant revenue growth and improved gross margins in the retail sector, indicating positive consumer behavior.

3.    Impact of Interest Rates: Simeon discusses the potential effects of Federal Reserve decisions on retail performance. While lower interest rates traditionally stimulate spending, he suggests that the impact may not be as significant for retailers, particularly those with strong cash positions and minimal debt.

4.    Segment-Specific Performance: Retail success varies across different sectors and brands. Simeon emphasizes that success in retail requires a compelling story, understanding of the target customer, and execution. He notes that while certain sectors like luxury and teen retail are thriving, success isn't guaranteed solely by being in a favorable sector.

5.    DTC (Direct-to-Consumer) Realities: There's a growing realization that DTC isn't always the golden solution it's made out to be. Removing the middle person doesn't necessarily lead to cost savings for the consumer; instead, the costs are absorbed differently. Brands pivoting to DTC may not see the expected increase in revenue, gross margin, or profit.

6.    The Power of Off-Price Retailing: TJX (T.J. Maxx, Marshalls, HomeGoods) is recognized as a disruptor in the retail sector, despite its minimal e-commerce presence. Their model of selling expensive items at discounted prices has reshaped consumer perceptions and buying habits. Other off-price retailers may also take share from consumers but in different ways.

7.    Reevaluating Growth Strategies: Companies like Under Armour, despite revenue size, may face challenges due to low gross margins. Reevaluating strategies, possibly shifting from over-distribution to focusing on quality over quantity sales, may be necessary for sustained profitability.

8.    Tech Integration in Retail: While technology offers numerous solutions for retail, the challenge lies in identifying the most effective ones amidst the plethora of options. Companies should focus on tech solutions that reduce shrink, automate supply chains, and improve customer targeting, without letting technology overtake the core business.

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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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On Episode 30 of The Retail Pilot, Ken Pilot interviews Stephen Kuhl, Co-Founder and CEO of Burrow, a furniture design brand that’s making it radically easier for people to feel at home through innovative, award winning, furniture and unparalleled customer experience. Launched in 2017, Burrow is one of the fastest growing furniture brands in the world and has raised venture capital from leading venture firms including New Enterprise Associates, Y Combinator, Parkway VC, and Red & Blue Ventures. Mr. Kuhl is an investor and advisor to several startups including Commerce Bear, Suite Plants, and Desk View. Prior to Burrow, Mr. Kuhl was a growth investor at Commonfund Capital and worked in Accenture’s Global Strategy group, specializing in operating model design. Mr. Kuhl earned a B.S. with honors from Cornell University and an M.B.A. from The Wharton School at the University of Pennsylvania.

1.    Inception of Burrow: Stephen Kuhl, the CEO and co-founder of Burrow, shared how the idea for the company originated during an entrepreneurship class at Wharton. The inspiration came from the success of mattress-in-a-box companies like Casper, and the vision was to apply a similar concept to furniture.

2.    Revolutionizing Furniture Retail: Burrow's innovative approach involves modular, easy-to-ship furniture that can be assembled without the need for tools. This concept was developed strategically to optimize the supply chain for e-commerce, allowing for quick delivery and a wide range of customizable options.

3.    Strategic Branding with Red Antler: Kuhl highlighted the importance of branding in communicating Burrow's value proposition. The company collaborated with Red Antler for naming, visual identity, and storytelling, which played a crucial role in establishing Burrow as a distinctive D2C furniture brand.

4.    Business Growth and Model: Burrow has seen significant growth, with over 100 million in top-line sales. The company's primary focus is direct-to-consumer sales, with about 90% of their business conducted online. They also operate showrooms where customers can experience the products in person.

5.    Competing with Established Brands: Burrow competes directly with well-known brands like West Elm and Crate and Barrel. The key differentiators for Burrow are the quality, durability, convenience, and speed of delivery they offer compared to their competitors in a similar price range.

6.    Transition to Sole CEO: Stephen Kuhl discusses the transition from being co-CEO with Kabir to becoming the sole CEO of their company, Burrow. He explains that early on, they were co-CEOs, but Y Combinator advised against it, leading them to drop the title and become co-founders. Ultimately, they decided on their roles, with Stephen as the CEO and Kabir as the CTO.

7.    Importance of Co-Founders: Kuhl emphasizes the significance of the co-founder role, stating that no matter the titles, they both remained co-founders, and the success of the company depended on both.

8.    Tech Stack and SaaS Tools: Kuhl shares some details about their tech stack, mentioning that they use BigCommerce for their e-commerce site and NetSuite for ERP. He highlights the importance of leveraging technology throughout their business, including marketing technology, and the potential role of AI in future marketing.

9.    Marketing Strategies: The discussion touches on the challenges of marketing, particularly in the post-iOS changes era. Kuhl talks about diversifying their marketing channels, adapting to platforms like Instagram, TikTok, and Reels, and exploring content that resonates with their target audience.

10.    Path to Profitability: Kuhl talks about Burrow's path to profitability, mentioning that they achieved profitability...

Join Ken Pilot as he speaks with Co-Founder and CEO of Rhone, Nate Checketts, about his menswear business focused on fitness, comfort and everyday wear.

Prior to Rhone, Nate worked for and consulted with some of the biggesttechnology and entertainment properties in the world including Cisco, The NationalFootball League, Legends, FanVision and Sport Radar. Nate is also an avid entrepreneur who founded and launched 4companies before the age of 30, including Rhone and Mangia Technologies, whose patents were later acquired by the San Francisco 49ers. In 2020 Nate was selected by the Sports Business Journal to their 2020 list of Forty leaders under Forty.

In addition to Rhone, Nate also serves as Chairman of the Board to Beyond Type 1, a non-profit dedicated to the community of those with Type 1 Diabetes. Nate graduated from Brigham Young University with a BA in Finance. He and his wife Dayna reside in Connecticut with their three young boys, Gabriel, William and Nicholas.

About Rhone was founded in 2014 by brothers Nate & Ben Checketts. Rhone is a premium men's wellness brand that creates best in class performance-driven apparel that is engineered for an active lifestyle. Rhone is dedicated to using their platform and products to address and discuss the complex issues that modern men face. From raising awareness around the mental health crisis, to building mutually supportive communities, to providing men with practical tools and resources to navigate relationships, Rhone seeks to support men while providing them with versatileclothing for every aspect of their daily routine. Currently, Rhone has more than ten retail stores across the U.S., all of which are used for building community through various initiatives such as the brand's signature Mind & Muscleevents. Rhone is also sold in all Equinox locations, and available nationwide at Nordstrom, Bloomingdale’s, Dillard’s, SCHEELS, select CorePower Yoga locations, and more than 350 gyms and specialty stores across the country. Rhone is also a proud partner of Stitch Fix. More information can be found at www.Rhone.com.

Key Highlights Include:

Rhone's Origin and Vision: Rhone, a men's performance lifestyle brand, was founded with a vision to fill a void in the men's fashion space. The founders, including Nate Checketts and his brother Ben, aimed to create a brand that offered high-quality, versatile, and high-performance clothing that could be worn in various settings, blurring the lines between work and leisure attire.

Balancing Family and Business: Nate and his brother Ben, along with their brother-in-law, founded Rhone as a family venture. They emphasize that working together as a family has been a positive experience, and Ben's interest in clothing design complemented Nate's entrepreneurial background.

Omni-Channel Approach: While Rhone began as an e-commerce brand, it recognized the importance of an omni-channel approach. They expanded into physical retail stores, selecting high-end partners like Equinox to offer their products. This strategic move allowed them to meet customers where they were and helped them gain recognition in the market.

Retail Expansion and Profitability: Rhone currently operates 15 retail stores, and they prioritize profitability over rapid expansion. They are careful in selecting wholesale partners, ensuring that the brand is represented appropriately. All of their stores are profitable, which has provided a strong foundation for future growth.

Future Growth and Product Expansion: Rhone is exploring opportunities for growth, including potential expansion into the international market. They are also considering product line extensions, including potentially re-entering the women's market. However, their primary focus remains on delivering exceptional...

Ken Pilot interviews Janet Hayes, CEO of Crate & Barrel Holdings, for this episode of The Retail Pilot podcast.

Summary

Janet Hayes, CEO of Crate and Barrel Holdings, shares her journey into retail and her experience leading the company. Crate and Barrel Holdings is a multi-brand, multi-platform, multi-country company with four brands: Crate and Barrel, CB2, Crate and Kids, and Hudson Grace. Hayes discusses the strategy behind physical retail and the importance of providing exceptional shopping experiences. She emphasizes the need to inspire customers and make the buying process easier, especially in the home furnishings industry. Hayes also highlights the investment in store design, technology, and employee training to enhance the customer experience. Crate and Barrel has been addressing tech debt and selectively replacing technology to improve the customer experience. The company has a comprehensive strategy that includes technology, process, and culture changes. The leadership team consists of both tenured individuals and new hires, bringing a balance of experience and innovation. Crate and Barrel is focused on international growth, particularly in Europe and Canada. The company is preparing for the future of home decor by considering the impact of AI and maintaining a focus on quality and sustainability. Collaborations with influential partners have been successful in keeping the brands fresh. The marketing strategy is shifting towards digital and personalized content. Janet Hayes is motivated by the commitment to customers and employees, and she enjoys the energy and growth of the retail industry.

Takeaways

• Janet Hayes has over 30 years of experience in retail and has worked for companies like Macy's, Gap, Nike, and Williams Sonoma before joining Crate and Barrel Holdings as CEO.
• Crate and Barrel Holdings is a multi-brand company with four brands: Crate and Barrel, CB2, Crate and Kids, and Hudson Grace.
• The strategy behind physical retail for Crate and Barrel Holdings is to provide exceptional shopping experiences and inspire customers.
• Investments have been made in store design, technology, and employee training to enhance the customer experience.
• Crate and Barrel Holdings is focused on market share and has gained significant market share in the home furnishings industry.
• The company is investing in a new POS system that will enable associates to take transactions wherever the customer is, providing a seamless and convenient shopping experience. Crate and Barrel is addressing tech debt and selectively replacing technology to improve the customer experience.
• The company has a comprehensive strategy that includes technology, process, and culture changes.
• The leadership team consists of both tenured individuals and new hires, bringing a balance of experience and innovation.
• Crate and Barrel is focused on international growth, particularly in Europe and Canada.
• The company is preparing for the future of home decor by considering the impact of AI and maintaining a focus on quality and sustainability.
• Collaborations with influential partners have been successful in keeping the brands fresh.
• The marketing strategy is shifting towards digital and personalized content.
• Janet Hayes is motivated by the commitment to customers and employees, and she enjoys the energy and growth of the retail industry.

Chapters

00:00

Introduction and Janet Hayes' Journey into Retail

08:23

Taking on the Role of CEO at Crate and Barrel Holdings

11:24

The Strategy Behind Physical Retail at Crate and Barrel Holdings

18:57

Investing in Exceptional Shopping Experiences

23:15

Enhancing the Customer Experience with...

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Their story began in the offices of Sam & Libby Shoes, a modest footwear brand in California. John Edelman, working alongside his brother Sam, crossed paths with John McPhee, igniting a friendship that would set the stage for an indelible partnership. In their candid discussion on The Retail Pilot, the two Johns share the story of their humble beginnings, recounting how a casual dinner invitation would eventually reshape the design landscape.

Their collaborative efforts led them to Edelman Leather, a family business they nurtured into a multi-million-dollar success, later acquired by Knoll. The challenges didn't stop there. Together, they took on the ambitious task of revitalizing Design Within Reach. Against all odds, Edelman and McPhee orchestrated a remarkable turnaround, proving that dedication and strategic thinking can redefine a brand's identity.

Tune in as the Johns recall their pivotal moments, from facing skeptical employees to forging relationships with international vendors.

Learn how their enduring partnership reflects their shared values and commitment to exceptional design. Plus, tune in to discover their life now as John Edelman is President & CEO at Heller and John McPhee is CEO and Chilewich.

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On this flight of The Retail Pilot, Ken Pilot interviews Andrew Blackmon, the co-founder and CEO of The Black Tux. He manages the company's day-to-day operations and leadership team. He is passionate about diligently creating a great team/culture to execute on the company's long term vision of revolutionizing the men's formal industry. He previously worked in technology and marketing. He earned an MBA from HEC Paris and a degree in English from Pepperdine University.

Key takeaways from this podcast interview include:

1.    Identifying a Gap in the Market: Andrew and his co-founder Patrick identified a gap in the formal wear rental market through personal experience attending weddings and proms. They noticed that the available options often resulted in ill-fitting, low-quality garments, leading them to envision a better customer experience.

2.    Naivety as an Advantage: Despite lacking expertise in fashion or retail, Andrew and Patrick's youthful naivety served as an advantage. Their lack of preconceived notions allowed them to pursue their vision with energy and enthusiasm, unencumbered by industry norms or limitations.

3.    Investment and Infrastructure: The Black Tux faced challenges in securing initial investment, but eventually attracted funding from venture capitalists who believed in their concept. Building the necessary infrastructure, including warehouses equipped with dry cleaning and tailoring services, was capital-intensive but crucial for the business's success.

4.    Customer-Centric Approach: The Black Tux prioritizes the customer experience, aiming to provide high-quality, stylish rentals at affordable prices. Their focus on customer satisfaction has fueled word-of-mouth growth and contributed to their success, with over 2 million customers served to date.

5.    Diversification and Growth Opportunities: The company has expanded beyond rentals to offer products for purchase, responding to customer demand. Additionally, they are exploring opportunities for further expansion, including increasing their product assortment and opening more store locations, both independently and in partnership with retailers like Nordstrom. This focus on diversification and expansion reflects theircommitment to continued growth and innovation in the formal wear market.

6.    Identifying a Niche Market: The Black Tux identified a gap in the men's wedding band space, similar to the one they observed when they started in the tuxedo rental business. They noticed that men lacked a brand specifically targeting them for wedding bands, and they saw an opportunity to provide a branded experience like they did with Black Tux.

7.    Strategic Acquisition: Instead of just entering the jewelry market, The Black Tux strategically acquired a jewelry company with a deep history in the manufacturing side of the business. This allowed them to tap into existing expertise and offer high-quality men's wedding bands that are locally manufactured.

8.    Adapting to Market Trends: The company has expanded its product offerings beyond wedding bands to include other jewelry items like chains and bracelets. This expansion reflects the growing trend of men's interest in jewelry and allows The Black Tux to cater to a broader range of customer preferences.

9.    Direct Customer Engagement: The CEO, Andrew, personally engaged with customers through a unique SMS campaign, where he shared his own phone number and responded to every message. This direct engagement helped build a strong connection between the brand and its customers, fostering trust and loyalty.

10. Challenges and Future Plans: Despite facing challenges like a decline in weddings due to fewer relationships formed during COVID, The Black Tux is focused on overcom...

Join us in this inspiring episode as Ken sits down with Joey Zwillinger, the Co-founder & CEO of Allbirds, the groundbreaking footwear brand that's taking the world by storm. From humble beginnings to a global sensation, Allbirds has redefined the way we think about shoes, combining style, comfort, and sustainability in a way that's never been seen before.

In this candid conversation, Joey takes us on their remarkable journey, sharing the challenges he faced as they disrupted the traditional footwear industry with their eco-friendly, renewable materials and commitment to reducing their carbon footprint. Ken and Joey delve into the early days of Allbirds, from the spark of an idea to the inception of a brand that has now become a symbol of sustainable fashion.

Learn how they navigated the ever-changing world of fashion and e-commerce, adapting to evolving consumer preferences while staying true to their brand values. We'll also discover the pivotal moments that shaped their company and the values that continue to guide their decisions.

Listen now and explore the inspiring journey of Allbirds, a brand that proves that style, comfort, and sustainability can go hand in hand, revolutionizing the way we walk through life.

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Get ready for an exciting episode of the Retail Pilot as Ken sits down with Chris Burch, one of the most successful entrepreneurs and investors in the game. With over 40 years of experience in business and retail, Chris has a wealth of knowledge to share.

Join Ken as he delves into Chris's journey, from his early days selling sweaters as a college student, to his work at Tory Burch, and his current role as the founder & CEO of Burch Creative Capital. Chris shares his insights on entrepreneurship, innovation, and the future of the retail industry.

Whether you're an aspiring entrepreneur or a seasoned business leader, this episode is packed with valuable insights and advice from one of the most creative minds in the industry. Tune in now to hear from Chris Burch himself!

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Throwing it back to the second episode of The Retail Pilot, join your host Ken Pilot, as he continues the conversation with Millard "Mickey" Drexler, Retail visionary and Chairman of Alex Mill.

Come along for the ride as Ken and Mickey chat more about Mickey's legendary career building brands and his legacy with leading companies such as Ann Taylor, Gap, Old Navy, J.Crew, Madewell and now Alex Mill.

If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

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Join us on this special flight of the Retail Pilot as Ken sits down with Andrea Weiss, a trailblazing retail executive and philanthropist.

Andrea is the founder of The O Alliance, a global consulting practice focused on the retail, e-commerce, and consumer sector. She has had a distinguished career in senior leadership roles with some of the world's foremost retailers, including Guess, L Brands, and Ann Taylor.

Andrea is also a member of several public company boards, including Bed O'Reilly Auto Parts and Cracker Barrel Restaurant.

As a philanthropist, she serves as Vice Chairman of the Board of Trustees of Hampton University and Chair of Delivering Good, a 501(c)3 charity. In this episode, Andrea shares her inspiring journey and insights on leadership, diversity and inclusion, and the future of retail.

Tune in now to learn from one of the most influential women in the retail industry! 

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Next up on The Retail Pilot podcast, Ken sat down again with Millard "Mickey" Drexler, Chairman of Alex Mill.

Come along for the ride as Ken and Mickey chat more about Mickey's legendary career building brands and his legacy with leading companies such as Ann Taylor, Gap, Old Navy, J.Crew, Madewell and now Alex Mill.

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In this Flight of The Retail Pilot - Leaders & Legends, Ken speaks with Sharon Leite, CEO of Ideal Image, former CEO of The Vitamin Shoppe and Retail Leader at companies such as Gap, Bath and Body Works and Pier 1.

Key Takeaways of the Episode:

* Passion and Connection to Mission: Sharon emphasizes that passion for the business, brand, product, and mission is more important than monetary compensation. Connecting personally with your work is crucial for long-term success.

* Career Stages and Growth: Sharon's career evolved through three distinct stages: learning the business and consumer experience, turning around businesses, and applying her knowledge to legacy brands. Each stage contributed to her growth and success.

* Due Diligence and Understanding: Sharon learned the importance of thorough due diligence when considering new opportunities. Understanding the company, industry, and board's vision is essential for a successful and fulfilling career.

* Surrounding Yourself with the Right Team: Building a team that shares the vision and understands what excellence looks like is crucial, especially in situations requiring rapid change or turnaround. Having the right people in the right roles accelerates progress.

* Transforming a Business: Sharon's experience at the Vitamin Shoppe highlights the significance of rebranding, understanding the customer, telling compelling stories, and aligning with industry experts. This transformation ultimately led to success despite the challenges presented by COVID-19.

* Adaptation during COVID-19: The Vitamin Shoppe faced challenges during the COVID-19 pandemic. She had to fight to reopen their stores, and what allowed her to do so was a focus on selling essential items like food, functional foods, and water.

* Preparation paid off: Before the pandemic, the company had made strategic investments in e-commerce, technology, and loyalty programs. This preparation proved crucial, as they didn't have to scramble to implement services like online pickup, curbside pickup, etc., when COVID-19 hit. This readiness accelerated their growth during the pandemic.

* Leadership through presence and celebration: Sharon emphasized the importance of showing up, especially during tough times. She visited distribution centers, stores, and events, creating a celebratory environment within the company. This approach helped foster a sense of appreciation and connectedness among the team.

* Transition from public to private company: Sharon’s company transitioned from being a public to a private company. This move allowed her to focus on long-term business improvements without being beholden to short-term investor expectations.

* Reimagining Ideal Image: Recently, Sharon transitioned to a new company, Ideal Image, with the goal of building a comprehensive women's lifestyle brand in beauty, health, and wellness. She plans to reimagine various aspects of the business, including services, culture, products, and market leadership. She also hinted at a potential move into health and wellness.

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Ken Pilot interviews Oliver Chen for this flight of The Retail Pilot podcast.

Oliver Chen is a Managing Director and senior equity research analyst covering retail and luxury goods at TD Cowen.  His deep understanding of the consumer and his ability to forecast the latest trends and technological changes that will impact the retail space have set him apart from peers.

Prior to joining TD Cowen in 2014, he spent seven years at Citigroup, worked in the investment research division at UBS, in the global mergers and acquisitions/strategic planning group at PepsiCo International, and in JPMorgan’s consumer products/retail mergers and acquisitions group.

Oliver holds a bachelor of science degree from Georgetown University, an MBA from the Wharton School at the University of Pennsylvania, and is a CFA charterholder.

His passion for the sector began at the age of 12 when he began working with his parents at their retail business in Natchitoches, Louisiana.

Summary:

In this conversation, Oliver Chen discusses the current state of luxury retail and the beauty sector, highlighting the challenges and opportunities faced by brands. He emphasizes the importance of pricing strategies, the impact of digital transformation, and the need for brands to connect with younger consumers. The discussion also covers emerging trends in fragrance, the potential of the men's beauty market, and the role of AI in enhancing the retail experience.

Key Takeaways:

• Luxury retail is facing an inflection point with declining sales.
• China's economic factors are influencing luxury spending.
• LVMH's strong brand portfolio positions it well in the market.
• Hermes thrives due to its timeless luxury appeal.
• Luxury brands are increasingly focusing on direct-to-consumer sales.
• Ralph Lauren's success is attributed to its cultural relevance and value perception.
• Fragrance is a growing category with opportunities for premiumization.
• The men's beauty market is still developing but shows potential.
• TikTok is becoming a significant platform for beauty brands.
• AI is set to transform the retail experience through personalized search.

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In the latest episode of the Retail Pilot - Leaders and Legends, join Ken as he sits down with Ramy Brook Sharp, CEO & Founder of Ramy Brook, a contemporary womenswear brand that helps women feel their best with the use of signature use of silk fabrics, lively colors and sophisticated silhouettes.

Ramy shares her inspiring journey of building a successful fashion brand from scratch, and how she's navigated the challenges and opportunities of the industry. With her passion for empowering women through fashion, Ramy has created a brand that truly celebrates individuality and confidence.

Tune in now to learn more about Ramy's inspiring story and her vision for the future of the fashion industry.

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Ken interviews Jeanne Jackson for this Flight of The Retail Pilot.

Jeanne P. Jackson is CEO of a private equity and consulting firm that she founded in 2002, MSP Capital. In 2018, she retired from Nike, Inc. after 16 years, serving first as a Board member for 7 years, then stepping into successive roles inside the Company as President, then Senior Advisor to the CEO. She recently retired from the Board of Directors of McDonalds, Inc., where she served since 1999, holding positions as Chair of the Compensation Committee, Chair of the Finance Committee, and member of the Governance Committee. She also recently retired from the Board of Kraft-Heinz, Inc., having served with Kraft Inc., since 2012, through the sale to a Warren Buffett/3G led Heinz, and staying with the combined Kraft Heinz entity until her retirement in May. She served on the Audit Committee and the Corporate Governance Committee. She serves currently as Director for Monster Beverages, Inc., and Delta Airlines,Inc., on both Finance and the People and Compensation Committees. In the past, Ms. Jackson has also served on the Boards of Nordstrom, Inc., Nike, Inc., Harrah’s Inc., Motorola Mobility Inc. (through its sale to Google), Williams-Sonoma, Inc., CRS Inc., and West Marine, Inc. Ms. Jackson has previously served as the Chief Executive Officer and President of Wal-Mart.com USA, LLC , President and Chief Executive Officer of Banana Republic, a Division of Gap, Inc., while simultaneously as President and Chief Executive Officer for Gap Inc.’s Direct division. Prior to Gap, Inc., Ms. Jackson held various retail and consumer Brand management positions with Victoria’s Secret, The Walt Disney Company, Saks Fifth Avenue, and Federated Department Stores.

Ms. Jackson has served on the Board of Advisors of the Harvard Graduate School of Business, and University of California, Irvine Merage School of Business. She is the Past President of the United States Ski and Snowboard Foundation Board of Trustees, and served on numerous Community Boards. She is currently a member of the International Women's Forum of Las Vegas, and has, in the past, been recognized by Business Week as “One of the Year’s 25 Best Managers,” by Fortune as one of “The Most Powerful Women in Business,” and by Ad Age as one of “The Most Powerful Women in Sports.” Ms. Jackson holds a BS from the University of Colorado, and an MBA from Harvard’s Graduate School of Business Administration.

Key takeaways from the podcast highlight Jeanne Jackson's impactful career in retail, showcasing her leadership skills, strategic thinking, and contributions to transforming and growing iconic brands.

1.    Transformation of Banana Republic: Jeanne Jackson reflects on her leadership at Banana Republic, where she took the brand from being perceived as a stepchild to becoming a formidable brand within the Gap portfolio. This transformation involved assembling a high-quality team and pushing against opposition to lead the brand into the e-commerce space.

2.    Transition to Retail Career: Jeanne's journey into retail wasn't initially planned. She had intended to enter the consumer packaged goods industry but was convinced by someone in the retail sector, Frank Arnone, to explore a career in retail. This encounter shifted her trajectory, leading her to successful roles at various retail companies.

3.    Learning and Leadership Development: Jeanne attributes her leadership skills to lifelong learning and accumulating experiences. From her early exposure to extemporaneous speaking in high school to her experiences in business school, including the Harvard Business School method's case study approach, she developed the ability to assimilate data quickly and make decisions convincingly.

4.    Selecting Board Positions: Jeanne shares her approach to selecting b...

Ken Pilot interviews Denise Incandela for this flight of The Retail Pilot.

Denise Incandela is Executive Vice President of Fashion and Private Brands for Walmart U.S. In this role, Denise is propelling Walmart’s reputation as a fashion destination, helping democratize access to stylish, quality apparel for Walmart’s 140 million weekly shoppers.

Before joining Walmart, Denise rose through the fashion industry ranks with roles as CEO of Aerosoles, President of Global Digital and Customer Experience for the Ralph Lauren Corporation and before that, EVP and CMO of Saks Fifth Avenue. Denise started her post MBA career at McKinsey & Company, where she was a leader of its retail practice.

Denise is a visionary retail executive and experienced public company board director who has transformed luxury brands and mass retailers for over 20 years, and she is renowned across the industry for her innovation and vision, team leadership and ability to drive results.

Key takeaways from this podcast interview include:

1.    Transformational Leadership: Denise Incandela's career trajectory reflects a commitment to transformational leadership. From her beginnings in investment banking and management consulting to her roles at Saks, Ralph Lauren, and Walmart, she has consistently sought opportunities to drive change and innovation within the retail industry.

2.    Early Adoption of E-commerce: Denise's entry into the retail industry was marked by the nascent stage of e-commerce. Her pivotal role in launching Saks' e-commerce business in 1999 highlights her foresight and willingness to embrace new technologies and trends, even when they were not widely accepted.

3.    Shift from Luxury to Mass Market: Denise's transition from luxury brands like Saks and Ralph Lauren to Walmart represents a significant shift in focus and target demographics. Despite the apparent disparity between luxury and mass-market retail, Denise saw an opportunity to leverage her expertise and drive transformation within Walmart's fashion segment.

4.    Building Strong Private Brands: Walmart's focus on developing private brands with distinct identities and market appeal is evident. Denise highlights the importance of building robust design teams and investing in brand development to create cohesive, desirable offerings exclusive to Walmart.

5.    Innovative Online Experience: Walmart's efforts to enhance the online shopping experience, particularly in the fashion segment, showcase a commitment to innovation. Features such as virtual try-on and social commerce initiatives demonstrate Walmart's willingness to embrace emerging technologies and adapt to evolving consumer preferences.

6.    Transformational Focus: Walmart is heavily focused on transformation, particularly in the fashion sector. They recognize the need to evolve beyond their dominant apparel business and explore new opportunities to grow.

7.    Marketing Evolution: The company acknowledges the changing landscape of consumer behavior and the importance of adapting marketing strategies accordingly. This includes leveraging technology and online platforms to reach consumers where they are.

8.    Marketplace Strategy: Walmart places significant emphasis on its marketplace strategy, which allows third-party sellers to offer products on its platform. This approach enables Walmart to expand its assortment without the need for additional inventory, contributing to growth and customer satisfaction.

9.    Store Reinvention: Walmart is actively reinventing its physical stores to enhance the fashion shopping experience. This involves overhauling assortments, improving visual displays, incorporating digital elements, and creating brand-focused environments to change c...

Ken interviews Veronica Miele Beard and Veronica Swanson Beard, sisters-in-law and Co-Founders of women's lifestyle brand, Veronica Beard.

Veronica Miele Beard is from North Caldwell, New Jersey, and hails from the world of finance. She worked in sales and trading at multiple investment banks on Wall Street—and did a stint in ad sales at Vogue—before becoming a partner and COO at technology hedge fund, Coatue, where she learned to take risks and build a business. A mother of five, Veronica loves to travel and take her kids off the grid.

Veronica Swanson Beard grew up on both coasts, in San Francisco, California and Naples, Florida. Her career in fashion started at Narciso Rodriguez and Alberta Ferretti, in wholesale, and as a buyer for Marissa Collections in Florida. If not a fashion designer, this mother of three would be flipping real estate and designing interiors.

Key Highlights of The Podcast:

1. Unique Beginnings and Partnership: Veronica Miele Beard and Veronica Swanson Beard met at a wedding and became sisters-in-law. Both shared a passion for fashion and product obsession, leading them to create a fashion line together.

2.Combining Different Skill Sets: Veronica Miele Beard came from a fashion background while Veronica Swanson Beard had a finance background. Their collaboration brought together creativity, fashion connections, business acumen, and an understanding of product, which played crucial roles in their company's formation.

3. Identifying a Market Void: Their vision focused on creating a "uniform" for women, beginning with the iconic Dickie jacket. Recognizing the need for versatile, interchangeable pieces that offered style, functionality, and adaptability for women in various professions and stages of life became their foundation.

4. Bootstrap Business Start: Starting the company required minimal initial funding. They operated from Veronica Miele Beard's apartment, driving around in Veronica Swanson Beard's car, creating samples, and handling everything themselves, emphasizing a hands-on approach and learning experience.

5. Adaptation and Growth: They initially positioned themselves in the opening designer market but repositioned to advanced contemporary, lowering price points by 30% to cater to a broader audience. Their ability to adapt, identify gaps in the market, and create a unique brand around quality products contributed significantly to their success.

6. Denim as a Crucial Component: The founders emphasize the importance of denim in their business. They've honed in on perfecting the fit and style of women's jeans, understanding that jeans are a fundamental aspect of American fashion. Denim is considered the casualization of Veronica Beard and is a key element in keeping customers engaged.

7. Customer-Centric Approach: They extensively study and understand their customers, considering various body shapes, sizes, and preferences. They recognize that women will go to great lengths to find the perfect pair of jeans and focus on ensuring their brand accommodates diverse customer needs.

8. Global Inspiration and Market Adaptation: Travel serves as a significant source of inspiration. They discuss visiting different cultures and markets, observing how women in various parts of the world approach fashion. Adapting their brand to suit different markets, understanding local preferences, colors, and trends, is a key part of their strategy.

9. Transition to Direct-to-Consumer and Retail Experience: The founders discuss their transition from wholesale to direct-to-consumer retail. They highlight the importance of owning the brand's narrative, storytelling, and creating an immersive experience in their stores, which serve as community hubs for their customers.

...

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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Join Ken as he chats with Rob Smith, CEO and Founder of The Phluid Project, a groundbreaking brand that has become a beacon of inclusivity and empowerment for the gender expansive movement. Tune in as Ken delves into Rob's inspiring journey, where he combines his expertise in retail with his deep passion for social justice to create a platform dedicated to the values and priorities of Gen Z.

As a trailblazer in the industry, Rob has led The Phluid Project to become a driving force in championing LGBTQIA+ rights and representation, with a particular focus on supporting underrepresented youth. In this conversation, Rob shares the story behind the creation of The Phluid Project and its mission to create a safe and affirming space for individuals across the gender spectrum.

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Ken Pilot interviews Stephen Yalof, President and CEO of Tanger, Inc.

Stephen Yalof is the President and Chief Executive Officer of Tanger Factory Outlet Centers, Inc., a leading operator of upscale, open-air outlet centers with 37 locations and an additional center currently under development across 20 states and Canada. Steve joined in April 2020 as President and Chief Operating Officer before succeeding Steven B. Tanger as CEO in January 2021, bringing with him over 25 years of experience in the commercial real estate industry, with a primary focus on the retail space. He oversees the operations of the executive and senior leadership teams, emphasizing evolving the customer shopping experience, and sits on the board of directors.

Before joining Tanger Outlets, Steve served as the Chief Executive Officer of Simon Premium Outlets, where he drove forward the expansion and development of their real estate portfolio. He previously served as Senior Vice President of Real Estate for Ralph Lauren and Senior Director of Real Estate for The Gap, Inc.

Steve serves as a Trustee of the International Council of Shopping Centers (ICSC), as well as on the advisory boards of HeadCount and the Center for Real Estate & Urban Analysis (CREUA) at George Washington University, his alma mater, where he earned a B.S. in Business Administration.

Key takeaways from this podcast are:

1.    Holiday Optimism: Yalof expresses optimism about the holiday selling season, citing it as one of the biggest weekends for retail sales. He emphasizes the importance of monitoring traffic, sales, and anecdotes in gauging success.

2.    Career Journey & Industry Connections: Yalof reflects on his career journey, starting from New Plan Realty Trust to working with the Gap and Ralph Lauren. He highlights the growth and accomplishments of individuals he's worked with who are now in influential roles in different companies within the retail industry.

3.    Outlet Centers & Retail Success: He delves into the outlet business model, highlighting how outlet centers differentiate themselves from traditional retail spaces. Yalof emphasizes how retailers in outlet spaces offer lifestyle-focused brand experiences and attract customers seeking brand-specific items.

4.    Tanger's Approach & Evolution: Tanger, now Tanger Inc., has redefined itself to adapt to changing consumer behavior, focusing on the local community and tourism. They've expanded offerings beyond just shopping to include better food options, amenities, and even entertainment to enhance the overall experience.

5.    Team Building & Field-Led Approach: Yalof emphasizes the importance of his team, the changes made to the leasing and operational structures, and the decentralization of the decision-making process. He values field-led management, considering each location's uniqueness and tailoring strategies accordingly.

6.    Leadership Transition and Vision: Steve Yalof has stepped into a prominent leadership role at Tanger Inc. after Steve Tanger's departure. Yalof's leadership, vision, and ability to attract talent are highlighted as crucial factors impacting the company positively.

7.    Challenges Faced: Yalof outlines three significant challenges: talent retention due to increased competition, security concerns related to organized crime affecting shoppers, and the impact of global economic fluctuations on consumer spending and disposable income.

8.    Diverse Growth Opportunities: Beyond organic growth strategies like adding new shopping centers, Tanger Inc. expl...

Ken Pilot interviews Jan Singer about her incredible career as a Retail and Fashion leader and Board Member.

Diverse Journey in Retail and Fashion: Jan Singer's career journey spans across various categories of business, not limited to retail. She's worked in luxury goods, beauty, and manufacturing for brands like Chanel, Calvin Klein, Prada, and Nike. Her experiences ranged from innovation to manufacturing and wholesaling.

Initiating Career at Chanel: Jan shared an interesting story about how she found a phone number for Chanel, called in, and ended up speaking with the president, which ultimately led to her landing a job at Chanel.

Challenging and Rewarding Leadership Roles: Jan believes that every job she's had has been challenging, and she's always been open to pushing herself to learn and grow. She mentioned navigating the 08 crisis at Nike as one of the most challenging moments. Additionally, running global footwear and apparel at Nike was a masterclass in leadership.

Qualities as a Leader: Jan emphasized the importance of generous leadership, being an energy giver, and leading with optimism. She also talked about the value of being an enterprise leader, making complicated things simple and repeatable, and considering the broader perspective beyond her own space.

Approach to Shaping Leadership Teams: Jan's approach to building a leadership team involves deep curiosity about why she's being brought in, understanding the problems the team is facing, and finding the critical few things that will make a difference. She values competency, chemistry, and balance in her teams, and is open to both internal and external talent.

Dynamic Nature of Retail: Jan Singer highlights the dynamic nature of the retail industry. She emphasizes that no single company has everything figured out, and various aspects like channel dynamics, wholesale, direct-to-consumer, and digital interactions are constantly evolving.

The Importance of Physical Stores: Jan Singer believes that stores are not dead; instead, they are evolving. She expresses her belief in the value of real estate, mentioning that stores are still crucial, but they might have shifted from malls to Main Street or open-air formats.

Retail as Therapy: Jan Singer sees retail as a form of therapy for consumers. She believes that the engagement with shopkeepers, store staff, or online customer service fulfills a human need for connection and interaction. People shop for various reasons, and it can be a positive and uplifting experience.

The Significance of Knowing the Consumer: Jan Singer emphasizes the importance of brands truly knowing their consumers. She mentions brands like Gucci that excel at understanding their customers' preferences and providing personalized services, whether through in-store interactions or online communications.

Technology and the Future of Leadership: The discussion touches on the evolving role of CEOs in the retail industry. Jan Singer suggests that the skills required today may be so diverse that a single CEO might not be sufficient. She speculates about the possibility of a collaborative leadership structure involving operations, technology, and product leadership

Overall, Jan Singer provides valuable insights into the retail industry, highlighting the need for adaptability, personalized experiences, and a balanced approach to leadership in today's rapidly changing landscape.

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Join us on an exciting episode of The Retail Pilot as Ken dives into the captivating world of fine jewelry with Jennifer and Kevin Fisher.

From humble beginnings to the glitzy heights of the fashion world, Jennifer and Kevin share candid anecdotes of their path to success, and the pivotal moments that shaped the Jennifer Fisher Jewelry empire.

Tune in to hear what makes Jennifer and Kevin a great team and how they are going through “hoops” to build their business. Plus, learn how Jennifer is leveraging her design and social following with CB2, Kassatex and more.

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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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