Welcome to Cloudlandia podcast

Welcome to Cloudlandia

Dean Jackson and Dan Sullivan

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.

172 episodios

The Outsiders Who Built Toronto
15/7/2026
1:00:41
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/
Discovering Zero
1/7/2026
50:28
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/
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Thirty Years of Vectors
17/6/2026
58:46
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/
Money, Scent, and the Art of the Did List
20/5/2026
1:03:55
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/
Guessing, Betting, and the AI Attention Economy
13/5/2026
1:05:53
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/
Rules Over Insights: Time Sense and the Decider Role
22/4/2026
55:57
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/
Secrets, Surveys, and 30-Year Bets
15/4/2026
1:02:41
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 Inevitability System
8/4/2026
1:05:07
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/
Thinking What You Think, Liking What You Like
1/4/2026
54:08
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/
Arguing With Time
25/3/2026
1:03:40
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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