Gap's Chief Entertainment Officer move

Steve Dennis and Michael LeBlanc kick off their annual predictions episode with a fast-moving review of the retail news of the week. They begin with the long-delayed U.S. TikTok deal finally reaching resolution, noting how deeply TikTok now influences product discovery, cultural trends, and transactional commerce through TikTok Shops. While the platform remains critical for retailers, both hosts raise concerns around privacy, political influence, and how algorithmic control may evolve under new ownership.

The conversation then turns to tariff volatility and geopolitical uncertainty, highlighting how unpredictable trade policy continues to make planning difficult for retailers. Steve points out that Amazon is already seeing tariff-driven price increases creep into both its first-party and marketplace businesses, reinforcing how global policy decisions are now flowing directly into consumer pricing. They also discuss Gap’s creation of a Chief Entertainment Officer role, using it as a signal that retailers are increasingly seeking growth through media, licensing, and brand-driven content ecosystems rather than traditional merchandising alone.

From there, Steve delivers his provocative 2026 retail predictions. He argues that the “Great Concentration” will continue, with Amazon, Walmart, and Costco capturing a disproportionate share of both sales growth and profits. This concentration fuels a powerful investment flywheel that makes it increasingly difficult for mid-tier retailers to compete. He predicts a mixed year for major turnarounds, with some traction at Gap and Nike, limited progress at Macy’s, and deeper structural challenges for Target.

AI emerges as one of the most consequential themes, with Steve describing 2026 as a truly “agentic” year. Search, shopping, and discovery are rapidly shifting toward AI-driven experiences, creating massive innovation but also high risk of disintermediation for brands that fail to adapt. Physical stores, he argues, will matter more for experiential brands and less for undifferentiated ones, accelerating the bifurcation between meaningful store concepts and those that lack a clear role.

Steve also predicts intensifying competition in last-mile delivery, as Amazon and Walmart push same-day and narrow delivery windows even further, especially in grocery and essentials. Luxury faces an uneven future, with Saks Global likely emerging from bankruptcy smaller and fragile, and growth concentrated among a few elite brands. Resale, however, finally appears poised for breakout momentum, driven by affordability pressures and improving business models across the sector. Wellness and longevity become a new growth frontier, extending far beyond groceries into subscriptions, services, and lifestyle ecosystems.

The episode closes with their “remarkable” stories of the week and a look around the corner, led by Lululemon’s latest product misstep involving see-through apparel and a tone-deaf customer response. Michael highlights the promotion of former guest Chris Nicholas to lead Walmart International, while Steve flags growing bond-market volatility as a key macro signal to watch. 

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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 2025 and continues to be a ReThink Retail Top Retail Expert for the fifth year in a row.