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