In this episode, I start with a trip back to 1916, when Clarence Saunders launched the first self-service supermarket, Piggly Wiggly, and everyone thought it was a ridiculous idea. Customers serving themselves? Paying cash instead of running a tab? Madness. Yet, it reshaped retail forever.

I use that story as a lens to explore today’s 'crazy-sounding' innovation: agentic shopping (AI agents shopping on our behalf). Drawing from retail analyst Andrew Lipsman’s critiques, I unpack why skepticism toward new retail tech is healthy, but can also blind us to early versions of world-changing ideas. From Webvan to Amazon to TikTok, I show how many 'failed' technologies weren’t wrong — they were just early.

Then, I dig into what needs to align for AI-driven shopping to go mainstream: better tech, real consumer pain points, frictionless distribution, sustainable economics, and cultural trust. 

Will agentic shopping become the next self-service revolution, or just another voice commerce flop? Let’s find out.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00 ] – The wild story of Clarence Saunders and how Piggly Wiggly reinvented grocery shopping.
[02:05 ] – The lesson: the future doesn’t arrive by request, it’s created by those who rethink inefficiencies.
[02:32 ] – Introducing today’s topic: why agentic shopping feels 'too weird' and why that’s familiar.
[03:13 ] – Andrew Lipsman’s skeptical take: retail tech hype cycles and a graveyard of failed innovations.
[04:17 ] – Why some 'failures' (like Webvan) were just early, not wrong — lessons from timing and execution.
[05:12 ] – Amazon’s early struggles: when buying books online seemed absurd until it wasn’t.
[07:24 ] – The TikTok lesson: from lip-syncing app to global phenomenon, how tech evolves beyond its first use case.
[08:14 ] – My firsthand experiment: buying a lavender candle through ChatGPT’s instant checkout (clunky but promising!).
[09:00 ] – What needs to align for agentic commerce to succeed: technology, pain, distribution, economics, and trust.
[12:33 ] – Back to Piggly Wiggly: irrational innovations often look crazy, until they become inevitable.
[13:28 ] – Final takeaway: better to prepare for possibility than assume limits based on early imperfections.

Links & Resources

• Read my related article from Tuesday, I Got Prime Deals. Or Did I? Why Consumer Distrust Is AI Shopping's Real Opening
• Read Andrew Lipsman's essay Agentic Commerce is a Collective Hallucination
• Read my article AI-Enabled Shopping Hits 74% Adoption
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn