Last week, I fell into the hype of Amazon’s Big Deal Days. And as the boxes arrived on my doorstep, I couldn’t shake one uncomfortable thought: "did I actually get a deal?" In this episode, I unpack why online shopping feels less like convenience and more like detective work these days.

From inflated list prices and contradictory product info, to fake reviews and ad overload, I explore the five major ways consumer trust has eroded in ecommerce, and why that’s opening the door for AI shopping agents to step in. Are tools like ChatGPT and Amazon’s Rufus the solution, or are we just trading one layer of trust for another? Tune in as I break down what’s really happening behind the checkout button and what the future of trustworthy shopping might look like.

This episode is sponsored by Connected Commerce at Acosta Group

Timeline

[00:00] – Asking the uncomfortable question: did I actually get a deal?
[01:00] – Why shopper satisfaction with Amazon’s Prime events is slipping
[02:00] – The five big reasons trust has eroded in eCommerce
[02:30] – Opaque pricing and the lawsuit accusing Amazon of fake discounts
[03:00] – Inconsistent product information and hidden shopping costs
[04:00] – Manipulated reviews and ad overload on retailer websites
[05:00] – How AI shopping tools can handle the “detective work” for consumers
[06:00] – The debate: Are AI shopping agents overhyped or essential?
[07:00] – My frustrating hunt for the perfect winter boots and why trust matters
[08:15] – How AI agents like ChatGPT, Perplexity, and Rufus can rebuild confidence
[09:00] – Amazon vs. Walmart: two very different approaches to AI-assisted shopping
[09:30] – Why AI shopping isn’t a gimmick — it’s a response to real consumer pain

Links & Resources

• Read Andrew Lipsman's Media, Ads + Commerce newsletter piece, Agentic Commerce is a Collective Hallucination
• Read my article Is Retail Media Actually Kinda 'Mid'?
• Subscribe to Retail Media Breakfast Club's daily newsletter
• Follow Kiri on LinkedIn