Rory Sutherland: How to Fix Housing, & Survive the AI Era
Rory Sutherland sits down with Lewis Oakley on Generation Uncharted to unpack why housing has become a generational trap, why innovation stalled in the physical world, and how AI could reshape work in ways no one is prepared for. Lewis flips the script and asks Rory what he would do if he were 20 years old today — where he’d live, what skills he’d build, and how he’d define success in 2025. Chapters 00:00 Aspirational culture & redefining success 01:15 If Rory were 20 again 03:09 Housing as a generational tax 08:46 You’re not buying a house — you’re buying planning permission 12:19 Why driving expands your life radius 17:53 The tech that improved everything except housing 21:03 Liberty ships & how to build homes like cars 37:34 Flying cars, blocked innovation & regulation 45:52 AI: huge potential, huge downsides 56:00 Missed opportunities: pubs, co-working, smart glasses 1:02:44 Rory’s product recommendation
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