Walmart just crossed a trillion-dollar valuation and is openly positioning itself as a tech-driven retailer. That milestone raises a bigger question we all care about: what has to change inside a company when the future is AI, omnichannel retail, and nonstop competition? I sit down with John Reeves, a 22-year Walmart veteran and lifelong merchant, to break down what we’re seeing on the ground and what we think it signals for 2026.

We dig into Walmart’s leadership transition and why succession planning is not org-chart theater. John shares what great CEOs do differently, including Doug McMillon’s habit of learning directly from stores and asking the questions other leaders avoid. We also talk about the practical side of transformation: using technology to improve merchandising, speeding up decision making, and preparing for how AI in retail will reshape jobs from the back office to the shopping cart bay. One of the most important points is also the simplest: paying associates more can be a strategic advantage when you’re trying to upgrade service, execution, and talent.

Then we widen the lens. Target’s brand is strong, but out-of-stocks, store standards, and long self-check lines can quietly drain trust and profitability, especially when higher-margin categories soften. Kroger’s new CEO hire gets us talking about store-walk leadership and what it takes to refocus a grocery giant on its core. We close with a clear-eyed look at Amazon’s habit loop, plus what Costco’s member trust and private label momentum can teach every retailer.

If you’re building a retail strategy for 2026, listen, take notes, and share this with a friend in the industry. Subscribe, leave a review, and tell us which retailer you’re watching most closely right now.