A Conversation with Jason “Retailgeek” Goldberg

“If you show me a company that succeeded with every experiment, I’ll show you a company that’s very poor at picking their experiments.” — Jason Goldberg

In this episode, Jason “Retail Geek” Goldberg — Chief Commerce Strategy Officer at Publicis Group and co-host of the top-ranked Jason & Scott Show — makes the case that most companies are asking the wrong question about AI. A 30-year commerce pioneer who launched Blockbuster’s first e-commerce site in 1995 and has since driven billions in online revenue across hundreds of clients, Jason brings rare long-view perspective to the agentic commerce moment. We dig into why Walmart went from banning AI to hitting a trillion-dollar market cap, why fast followers beat first movers, and what the one question Doug McMillan asked in every meeting has to do with all of it.

What You’ll Discover:

[02:16] Is Agentic Commerce Real — Or the Next Blockchain? → Jason’s framework for separating genuine disruption from hype, and why he thinks agentic is one of only five true disruptions in 6,000 years of commerce

[08:27] The Walmart Story: From “AI Is Illegal Here” to $1 Trillion → What a single question from Doug McMillan — asked in every meeting — unlocked inside the world’s largest retailer, and what it reveals about the job of a CEO in volatile times

[14:16] Efficiencies vs. New Behaviors: The AI Trap Most Companies Fall Into → Why optimizing what you already do will save you money this year and cost you everything in five — and the consumer behaviors that will disintermediate your shelf entirely

[19:06] The Gartner Hype Cycle as a Leadership Tool → How to use the trough of disillusionment to your advantage, and why being unrealistically optimistic about the future is just as dangerous as ignoring it

[23:11] The ROI Trap: Why You’ll Always Choose the Oak Tree Over the Acorn → The structural reason most companies starve their best future bets — and what exceptional organizations do differently

[25:15] Why Ivory Tower Innovation Almost Always Fails → The REI green vest story: what happens when the scientists solve the wrong problem, and where the real innovation instinct actually lives in your organization

[32:43] The Fast Follower Advantage — and the Regret Question → Why you haven’t missed the agentic window, what AltaVista vs. Google tells us about timing, and the one question to ask yourself before leaving any strategy meeting

Key Takeaways:

Being first rarely wins. Being prepared to move fast when the signal is clear almost always does. The CEO’s real job in disruption isn’t picking products — it’s being the chief change agent for 1.6 million people who learned from their predecessors. The ROI framework will always favor your existing business over your future one. Exceptional companies build a different budget category for experiments — and expect most to fail.

About Jason Goldberg:

Jason “Retail Geek” Goldberg is the Chief Commerce Strategy Officer at Publicis Group, where he advises the world’s largest retailers and brands on digital transformation. He co-hosts the top-ranked Jason & Scott Show podcast and has been named a leading global retail influencer by Rethink Retail for six consecutive years.