Make It Happen: Jenny Ming on Leadership, Legacy, and the Power of Starting Smart

Make It Happen: Jenny Ming on Leadership, Legacy, and the Power of Starting Smart

In this inspiring episode of The Retail Pilot, retail legend Jenny Ming shares her remarkable journey—from launching Old Navy at Gap Inc. to leading transformative growth at Rothy’s. Jenny reveals how she navigated career pivots, built billion-dollar brands, embraced fast fashion logistics, and stayed true to her values through every leadership chapter. This is a masterclass in visionary retail, thoughtful decision-making, and building businesses with purpose.


Whether you're an aspiring entrepreneur, retail exec, or brand builder, Jenny’s insights on creating iconic customer experiences, staying nimble, and leading through complexity will leave you inspired and energized.

Show Notes:

  • Jenny shares the pivotal moment she was offered the opportunity to launch a new retail brand while planning a move to Hong Kong.

  • How Old Navy went from “Gap Warehouse” to a standalone brand—and why other potential names like “Monorail” and “Forklift” thankfully didn’t make the cut.

  • Her approach to launching with 50 stores from the start, and why thinking like an investor helped shape early decisions.

  • The reality of working with a lean, scrappy team and the lessons she learned in intrapreneurship at Gap Inc.

  • Why Old Navy's lighthearted brand tone and accessible price points resonated with families—and made fashion fun again.

  • Transitioning into CEO roles after Gap, including a decade at Charlotte Russe and her bold comeback at Rothy’s.

  • The importance of sustainability, style, and washability in Rothy’s brand DNA—and how Jenny helped the company return to profitability in months.

  • How she’s expanded Rothy’s into Nordstrom, Bloomingdale’s, Anthropologie, and international markets while maintaining brand integrity.

  • Her take on tariffs, supply chain diversification, and how early planning helped Rothy’s navigate disruption.

  • Why testing, listening, and growing with your team are pillars of her leadership style.

  • Jenny’s thoughts on the power of strategic collaborations, the future of retail tech, and what keeps her inspired as a mentor and coach.

  • Plus: her leadership must-do’s, favorite cities, favorite brands, and what she looks for when hiring.

    Enjoy the episode? Be sure to subscribe, leave a review, and share it with someone who’s building something bold. Your support helps us bring more candid stories from retail’s top voices to your feed.


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Unpacking Q3 Consumer Insights With Oliver Chen: Luxury, Beauty, Retail & AI

Unpacking Q3 Consumer Insights With Oliver Chen: Luxury, Beauty, Retail & AI

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

30 Okt 202440min

Bursting the Skincare Bubble: How Shai Eisenman Set Out to Disrupt the Skincare Industry

Bursting the Skincare Bubble: How Shai Eisenman Set Out to Disrupt the Skincare Industry

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 entrepreneurshipBubble focuses on affordable, high-quality skincare products for younger consumersThe company built a community of 4,600 Gen Z advisors before launchingBubble now has over 50,000 brand ambassadors who provide input on all decisionsProducts are priced affordably (around $15) but with prestige-level qualityInitially launched D2C but quickly pivoted to retail partnershipsNow available in 13,000 U.S. stores including Walmart, Ulta, CVS, and AmazonRecently expanded to the UK (Boots) and Australia (Priceline)Business Strategy:Focused on margin dollars rather than margin percentageFound retail partnerships more profitable than D2C for their price pointInvests in physical experiences and grassroots marketing over traditional advertisingCollaborates with brands like Disney to reach new audiencesRaised capital primarily from individuals and early-stage fundsAims to be profitable and not reliant on external fundingCommunity Engagement:Uses multiple platforms to communicate with brand ambassadorsOffers gift cards and commissions to ambassadorsRuns college campus programs with exclusive merchandiseInvolves community in product development, naming, and marketing decisionsChallenges and Growth:Adapting leadership style and operations as the company scalesExpanding internationally while remaining an independent brandBalancing control over brand experience with benefits of retail partnershipsLeadership Insights:Values building a strong team and fostering communityRelies on experienced advisors for guidance in different growth stagesEmphasizes the importance of adapting to different business stages Hosted by Ausha. See ausha.co/privacy-policy for more information.

22 Okt 202435min

Mickey Drexler: A Mensch and a Mentor at the Helm of Alex Mill

Mickey Drexler: A Mensch and a Mentor at the Helm of Alex Mill

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

8 Okt 202451min

Simeon Siegel Returns: A Retail Analyst's POV on the State of the Industry

Simeon Siegel Returns: A Retail Analyst's POV on the State of the Industry

Ken Pilot interviews Simeon Siegel, MD and Senior Analyst, Retail & eCommerce for BMO Capital Markets, for this Flight of The Retail Pilot PodcastOverview: 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!Hosted by Ausha. See ausha.co/privacy-policy for more information.

17 Sep 202435min

Tech Talk: Digital Marketing Strategy for Retail Transformation - A Conversation with January Digital Founder & CEO, Vic Drabicky, & Stev...

Tech Talk: Digital Marketing Strategy for Retail Transformation - A Conversation with January Digital Founder & CEO, Vic Drabicky, & Stev...

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

10 Sep 202439min

Soft Threads, Bold Moves: Mike Natenshon's Journey as the Founder of Marine Layer

Soft Threads, Bold Moves: Mike Natenshon's Journey as the Founder of Marine Layer

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

4 Sep 202445min

THROWBACK EPISODE - "Burn Rate": How Andy Dunn Built and Exited Bonobos While Confronting Mental Illness

THROWBACK EPISODE - "Burn Rate": How Andy Dunn Built and Exited Bonobos While Confronting Mental Illness

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

27 Aug 202454min

From Gilt to Glamsquad: Alexandra Wilkis Wilson’s Journey Building Unicorns and Investing in Talent

From Gilt to Glamsquad: Alexandra Wilkis Wilson’s Journey Building Unicorns and Investing in Talent

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”.SummaryAlexandra 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.TakeawaysAlexandra 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.Chapters00:00Introduction and Background02:36The Attraction to Gilt05:34The Early Vision and Success of Gilt09:02Gilt's Journey to Unicorn Status12:07Challenges and Exit of Gilt15:29Glam Squad: Inception and Expansion18:44Lessons Learned and Next Ventures23:22Dresser and FITS: Innovative Ventur...

20 Aug 202447min

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