Make It Happen: Jenny Ming on Leadership, Legacy, and the Power of Starting Smart
The Retail Pilot10 Juni

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.


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

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Brian Berger: Innovation, technology and underwear - how a trip to a department store inspired the creation of Mack Weldon, "sharp clothe...

Brian Berger: Innovation, technology and underwear - how a trip to a department store inspired the creation of Mack Weldon, "sharp clothe...

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

1 Maj 202337min

Mindy Grossman: Award-winning brand-builder, inspirational leader and strategic visionary shares her inspiring story

Mindy Grossman: Award-winning brand-builder, inspirational leader and strategic visionary shares her inspiring story

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

24 Apr 202344min

Gary Sheinbaum & Nadia Boujarwah: Innovation and inclusivity in plus-size women's apparel

Gary Sheinbaum & Nadia Boujarwah: Innovation and inclusivity in plus-size women's apparel

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

17 Apr 202343min

Millard "Mickey" Drexler: A candid conversation about the life and career of an actual Retail "Legend" - Part 2

Millard "Mickey" Drexler: A candid conversation about the life and career of an actual Retail "Legend" - Part 2

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

6 Apr 202354min

Millard "Mickey" Drexler: A candid conversation about the life and career of an actual Retail "Legend" - Part 1

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

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