Winner Sells All: Exploring the Amazon and Walmart Rivalry with Jason Del Rey

Joining us in conversation about his just released new book Winner Sells All: Amazon, Walmart, and the Battle for Our Wallets is Jason Del Rey, the veteran business journalist who has spent a decade reporting on Amazon, Walmart, and how technology is transforming retail.

We explore the evolution of the rivalry and how it's shaped the world of commerce, while learning about some of the key inflection points that have propelled Walmart's race to embrace digital technology, including the Jet.com acquisition. We compare and contrast the two retail giant's innovation DNA through Jason's great behind the scenes anecdotes gleaned from his more than 150 interviews. We conclude with a review of each company's healthcare ambitions.

But first, as is our custom, we kick-off the penultimate episode of Season 6 with the week in retail news, exploring what the latest macro-economic news portends for the balance of the year. Then we do some quick hits on Overstock.com's "stalking horse" bid for Bed, Bath & Beyonds intellectual property, Westfield's decision to walk away from its downtown San Francisco mall, and what to make of Kroger's lukewarm earnings report.

About Jason

Jason Del Rey is a veteran business journalist who spent a decade at Recode, a leading online technology publication, reporting on Amazon, Walmart, and how technology is transforming retail, both online and in stores. He is the host of Land of the Giants: The Rise of Amazon, a narrative podcast series about the tech giant’s rise and the impact of its relentless ambition on hundreds of millions of people across the globe. He was also the producer of Code Commerce, an event series featuring unscripted interviews with the most influential executives and entrepreneurs working at the intersection of technology and commerce. In 2019, the National Retail Federation named him one of the “25 People Shaping Retail’s Future.” He lives in Northern New Jersey with his wife and two children.

About Us

Steve Dennis is an advisor, keynote speaker and author on strategic growth and business innovation. You can learn more about Steve on his website. The expanded and revised edition of his bestselling book Remarkable Retail: How To Win & Keep Customers in the Age of Disruption is now available at Amazon or just about anywhere else books are sold. Steve regularly shares his insights in his role as a Forbes senior contributor and on Twitter and LinkedIn. You can also check out his speaker "sizzle" reel here.

Michael LeBlanc is the Founder & President of M.E. LeBlanc & Company Inc and a Senior Advisor to Retail Council of Canada as part of his advisory and consulting practice. He brings 25+ years of brand/retail/marketing & eCommerce leadership experience, and has been on the front lines of retail industry change for his entire career. Michael is the producer and host of a network of leading podcasts including Canada’s top retail industry podcast, The Voice of Retail, plus Global eCommerce Leaders podcast, and The Food Professor with Dr. Sylvain Charlebois. You can learn more about Michael here or on LinkedIn.

Be sure and check out Michael's latest venture for fun and influencer riches - Last Request Barbecue, his YouTube BBQ cooking channel!

About Us

Steve Dennis is a strategic advisor and keynote speaker focused on growth and innovation, who has also been named one of the world's top retail influencers. He is the bestselling author of two books: Leaders Leap: Transforming Your Company at the Speed of Disruption and Remarkable Retail: How To Win & Keep Customers in the Age of Disruption. Steve regularly shares his insights in his role as a Forbes senior retail contributor and on social media.

Michael LeBlanc is a senior retail advisor, keynote speaker and media entrepreneur. Michael has delivered keynotes, hosted fire-side discussions hosted senior retail executive on-stage in 1:1 interviews worldwide. Michael produces and hosts a network of leading retail trade podcasts, including The Remarkable Retail Podcast, The Voice of Retail, The Food Professor, The FEED powered by Loblaw and the Global eCommerce Leaders podcast. He has been recognized by the NRF as a global Top Retail Voice for 2025 and 2026 and continues to be a ReThink Retail Top Retail Expert for the fifth year in a row.