AI-Fueled Shopping for The Holidays

This week, I’m breaking down a fascinating shift I’ve been watching closely: the moment AI-enabled commerce finally tips from novelty to norm, just in time for the holiday shopping rush. After a near-disaster of traveling without my wallet (which somehow wasn’t a disaster at all), I couldn’t help but notice how quickly behavior changes when technology quietly becomes infrastructure. And based on fresh Salesforce data, AI is hitting that same inflection point in retail.

In this episode, I dig into what’s different this year, why AI shopping tools are suddenly actually useful, and how shoppers are blending personalized AI agents with retailer-owned chat experiences. Plus, I share some surprising insights about Gen Z’s in-store resurgence, and why the most AI-proof part of retail media might just be happening in the physical aisle.

Timeline

[00:00] – The “forgot my wallet” travel moment and how quickly new behaviors become normal
[01:06] – Why this holiday season marks AI’s first real commerce stress test
[02:24] – The most meaningful new AI shopping tools consumers didn’t have last year
[03:52] – Are shoppers using retailer chatbots, or bringing their own LLM sidekick?
[06:29] – Salesforce data: retailers with AI chatbots are seeing 7× higher growth
[07:28] – The gap between retailer chatbots and personal AI assistants
[08:22] – Gen Z’s unexpected return to in-store shopping (with AI in hand)
[10:12] – What I’m watching as $73B in projected AI-influenced sales plays out this week

Links & Resources