Welcome to Cloudlandia

Dean Jackson and Dan Sullivan
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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.

  1. Jul 15

    The Outsiders Who Built Toronto

    In this episode of Welcome to Cloudlandia, Dean and Dan trace how a handful of outsiders built modern Toronto, and why every name they drop turns out to have something in common. Show notes: https://deanjackson.com/podcasts/wtc/178-the-outsiders-who-built-toronto/

    The Outsiders Who Built Toronto

  2. Jul 1

    Discovering Zero

    In this episode of Welcome to Cloudlandia, Dean and Dan explore why AI feels less like a new technology and more like the moment humanity discovered zero. Show notes: https://deanjackson.com/podcasts/wtc/177-discovering-zero/

    Discovering Zero

  3. Jun 17

    Thirty Years of Vectors

    In this episode of Welcome to Cloudlandia, these two longtime collaborators trace how small decisions compound over decades to build momentum. Show notes: https://deanjackson.com/podcasts/wtc/176-thirty-years-of-vectors/

    Thirty Years of Vectors

  4. May 20

    Money, Scent, and the Art of the Did List

    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/

    Money, Scent, and the Art of the Did List

  5. May 13

    Guessing, Betting, and the AI Attention Economy

    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/

    Guessing, Betting, and the AI Attention Economy

  6. Apr 22

    Rules Over Insights: Time Sense and the Decider Role

    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/

    Rules Over Insights: Time Sense and the Decider Role

  7. Apr 15

    Secrets, Surveys, and 30-Year Bets

    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/

    Secrets, Surveys, and 30-Year Bets

  8. Apr 8

    The Inevitability System

    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/

    The Inevitability System
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4.3
out of 5
10 Ratings

About

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.

Information

  • Creator
    Dean Jackson and Dan Sullivan
  • Years Active
    2020 - 2026
  • Episodes
    172
  • Rating
    Clean
  • Copyright
    © Dean Jackson and Dan Sullivan
  • Show Website
    Welcome to Cloudlandia

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