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

Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu

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

A running joke that it was peak AI hype,  - Shopify Editions Recap Conversation With Shopify Agencies

Kristen Wiley: Half of AI tools were built to write… LinkedIn posts - Influencer Marketing Should Be A Car That Can Be Driven Anywhere with Kristen Wiley

What AI still cannot automate: “judgment” (or taste) - How a 115-Year-Old Company Uses A Framework That Contains Bridges, Boats, and Moats with David Katz and  Beyond the Hype: The Future of Commerce, AI, and Human Creativity with Dilip Keshu

Culture & Leadership Themes (Culture Club)

“No courage in consensus.”

Jo Baker from https://www.youtube.com/watch?v=ym5QZpt3xzM

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

Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8

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

Donna Felix from https://www.youtube.com/watch?v=Lb1K--Ylvd8

Advertising and Retail Media Networks (Riddle Me RMN)

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

From https://www.youtube.com/watch?v=pQv5rWAAfNs

Marketplace & Retail Themes (Marketplace Mayhem)

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

Jack Freeman from https://www.youtube.com/watch?v=vJTDWyWqXmI - VC perspective: marketplaces sound utopian until the economics hit.

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

“Commission with extra steps.

A discussion of:

- Ulta launching a marketplace and a future episode.

- Beauty brands rising through TikTok.

- The need to balance seller and buyer incentives.

Marketplace guests:

Michael McCluskey, from Lowe's  - https://www.youtube.com/watch?v=8bMxX83kcPo

Logistics & Ops (Flexport Says What)

Delivery is the last touchpoint with the customer

John Shea from https://www.youtube.com/watch?v=ydQpB23iEf4

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

Nate Skiver from https://www.youtube.com/watch?v=HaRpllir2S4

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

CMOs will be part marketer and therapist.

Jo Baker from https://www.youtube.com/watch?v=ym5QZpt3xzM

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 https://www.youtube.com/watch?v=OnKh8ohmep0

• To Josh Carter: “Every cult says that.”

From https://www.youtube.com/watch?v=-XY_z3fEU_o

(Context/clues: influencers, brand community building)

The Watson Weekend is sponsored by Rithum

In commerce, every second counts.

Rithum connects every channel with AI automation and insights,

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

Learn more at rithum.com

Chapters

00:00- Introduction

02:24 - Headline Hangover

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

41:37- Show ends

#watsonweekend #ai #marketplaces #leadership #retailmedianetworks #jeoparty

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