The Best One Yet The Best One Yet

🌁 “LIVE from SF” — The Gap’s boy band. AI’s GrandmaSlop. SaaS: Swimming-as-a-Service. +SF Billboard Boom

Sep 24, 2026 · 25m

Summary

Hosts Nick and Jack discuss three pop business stories from a live show in San Francisco. First, The Gap is investing in a new boy band to recreate its 1990s "fashion-tainment" strategy. Second, they explore "grandma slop," noting that older generations embrace AI-generated family images while younger users react with disgust. Finally, they analyze private equity's consolidation of the pool maintenance industry into "swimming as a service."

Topics discussed

Intro: Live from SF and today's three stories San Francisco's AI billboard boom and city culture Sponsors: Monarch and Indeed The Gap invests in boy band JYT for 'fashion-tainment' Grandma Slop: AI images and the generational divide Sponsors: NetSuite and Nutrafol Private Equity and the rise of Swimming as a Service Audience recap and Best Fact Yet on SF history Live audience shoutouts and celebrations Closing thanks and Hotels.com sponsor segment
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