The Watson Weekend hosts, Rick Watson and Jessica Lasesky, and guest Nick Kaplan discuss retail and commerce trends for Q4 and 2025. This week’s headline hangover includes the resurgence of Toys R Us, Airbnb's pilot kitchen stocking service with Instacart, and the integration of AI to enhance efficiency rather than replace humans.

The Big 2025 “Jeoparty” Retro Game

Jeoparty host Jessica Lasesky uses the Watson Weekend version of the popular TV game show Jeopardy to try and confuse or showcase the brilliance of Rick Watson and Nick Kaplan. What did the previous Watson Weekend guests have to say about categories/topics such as Riddle Me RMN, Culture Club, AI Illuminati, Marketplace Mayhem, and Things Rick Said That Shouldn’t Be on Record?

AI & Tech Themes (AI Illuminati)

AI will not replace humans — it will reveal them

from • Beyond the Hype: The Future of Commerce, A...

Shopify Summer ‘24 Edition is described as “AI for AI”

A running joke that it was peak AI hype, - from • Shopify Editions Recap Conversation With S...

Kristen Wiley: Half of AI tools were built to write… LinkedIn posts - from • Influencer Marketing Should Be A Car That ...

What AI still cannot automate: “judgment” (or taste) - from • How a 115-Year-Old Company Uses A Framewor... and • Beyond the Hype: The Future of Commerce, A...

Culture & Leadership Themes (Culture Club)

“No courage in consensus.”

Jo Baker From • BigCommerce Marketing Needs Help Says Indu...

“Empathy doesn’t slow performance — it scales it.”

Donna Felix from • The Watson Weekend Live Show: Ep. 61 w/ Do...

The winning blend of traits: IQ + EQ + adaptability (AQ)

Donna Felix from • The Watson Weekend Live Show: Ep. 61 w/ Do...

Marketplace & Retail Themes (Marketplace Mayhem)

“Everyone’s a disruptor… until the invoice shows up.”

From • The $36 Trillion B2B Commerce Revolution: ... - VC perspective: marketplaces sound utopian until the economics hit.

Sellers say marketplaces “empower sellers”—but sellers call it:

“Commission with extra steps.

Marketplace guests:

Michael McCluskey, from Lowe's - • Lowe's VP Reveals How They Built a $[___] ...

A discussion of:

Ulta launching a marketplace and a future episode.

Beauty brands rising through TikTok

Need to balance seller and buyer incentives

Logistics & Ops (Flexport Says What)

Delivery is the last touchpoint with the customer

John Shea from • The Amazon Power Play: John Shea Breaks Do...

Golden rule: “Over-communicate and never miss a promise date.”

Nate Skiver from • Shipping Smackdown: Nate Skiver on the Par...

The team jokes about Rick’s spicy-wing “emotional memory” during the Auctane interview.

Favorite Rick Quotes (Things Rick Said That Shouldn’t Be on Record)

These were turned into trivia questions:

“Vibe-based forecasting”

(Describing certain retail forecasting styles)

Agency attribution = “Kabuki theater”

(Paid media taking credit for brand-driven performance)

To Dave Finnegan’s ‘curiosity is strategy’: “That’s a KPI I can respect.”

From • From Orvis to Dinosaurs: A Conversation wi...

To Josh Carter: “Every cult says that.”

From • Social Commerce Showdown: Josh Carter on T...

(Context: influencers, brand community building)

Advertising and Retail Media Networks (Riddle Me RMN)

The word Kiri Masters swore she’d never say again in 2025 - Incrementality

From • The Internal Conflicts Retail Media Networ...

The Watson Weekend is sponsored by Rithum

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helping brands grow profitably across marketplaces, dropship, and retail media.

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Chapters

00:00- Introduction

02:24 - Headline Hangover

08:32 - The Big 2025 “Jeoparty” Retro Game

41:37- Show ends

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