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Welcome to Cloudlandia

Welcome to Cloudlandia

Written by: 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.© Dean Jackson and Dan Sullivan
Episodes
  • The Outsiders Who Built Toronto

    The Outsiders Who Built Toronto
    Jul 15 2026
    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/
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    1 hr and 1 min
  • Discovering Zero

    Discovering Zero
    Jul 1 2026
    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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    50 mins
  • Thirty Years of Vectors

    Thirty Years of Vectors
    Jun 17 2026
    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/
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    59 mins
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