Episodes
172
Latest episode
Jul 2026
Language
EN-US
Dean Jackson and Dan Sullivan think out loud about business, marketing, technology, and the ongoing move of the economy into "Cloudlandia", the digital-first world layered over the physical one. Long-form, unscripted conversations between two longtime collaborators.
How a handful of outsiders built modern Toronto, and why every name that comes up turns out to have something in common. Show notes: https://deanjackson.com/podcasts/wtc/178-the-outsiders-who-built-toronto/
Why AI feels less like a new technology and more like the moment Europe discovered zero, when traders could do in seconds what took all afternoon. Show notes: https://deanjackson.com/podcasts/wtc/177-discovering-zero/
Dan's annual London trip, AI transforming industries the way automation reshaped farming, and his MELT framework: money, energy, labor, transport. Show notes: https://deanjackson.com/podcasts/wtc/176-thirty-years-of-vectors/
The most enduring business lessons often come wrapped in the most unexpected stories. Show notes: https://deanjackson.com/podcasts/wtc/175-money-scent-and-the-art-of-the-did-list/
The most valuable currency in an AI-saturated world isn't data or content, it's the 1,000 minutes of attention each person has available every single day. Show notes: https://deanjackson.com/podcasts/wtc/174-guessing-betting-and-the-ai-attention-economy/
The most powerful systems aren’t built on motivation; they’re built on rules that make the right action the only option. Show notes: https://deanjackson.com/podcasts/wtc/173-rules-over-insights-time-sense-and-the-decider-role/
Protecting what you've built, revisiting where you started, and betting on the systems that have never let you down. Show notes: https://deanjackson.com/podcasts/wtc/172-secrets-surveys-and-30-year-bets/
The most productive stretch of your life probably isn’t waiting for motivation, it’s waiting for the right constraint. Show notes: https://deanjackson.com/podcasts/wtc/171-the-inevitability-system/
A candid reflection on how the spread of AI is making authentic human presence feel more valuable, not less. Show notes: https://deanjackson.com/podcasts/wtc/170-thinking-what-you-think-liking-what-you-like/
Every conversation has the potential to reveal something useful hidden within the ordinary, and this one delivers several of those moments. Show notes: https://deanjackson.com/podcasts/wtc/169-arguing-with-time/
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Ann Carden
Holly Jean Jackson
Dr. Allen Lycka
