Co-CEOs, Devil Wears Prada 2, AI Creativity, Brian Chesky's Hiring | What We Don't Know: Watercooler

Co-CEOs, Devil Wears Prada 2, AI Creativity, Brian Chesky's Hiring | What We Don't Know: Watercooler

From What We Don't Know with Matt Brittin & Hayaatun Sillem by Boxlight Creative Studio

May 13, 2026 · 24 min

About this episode

Hayaatun and Jimmy discuss various topics including awards, AI, leadership models, and loyalty in organizations.

Awards, AI, Co-CEOs & Loyalty | What We Don't Know Watercooler Hayaatun and Jimmy pull up a chair at the coffee machine to catch up on what's been catching their eye - the City AM Awards, The Devil Wears Prada 2, a controversial Airbnb CEO interview, and your questions on noise, loyalty, and whether AI will swamp the best human ideas. Timestamps 00:00 Welcome to the coffee machine 00:45 Are awards overrated, or do we actually need them? 02:00 The UK startups that got away: why the post-pandemic story isn't as bleak as you think 04:00 The Devil Wears Prada 2 and what pop culture gets right about loving hard work 05:30 Brian Chesky personally hires Airbnb's top 200 — genius or quietly disempowering? 08:30 Co-CEOs: bold leadership model or recipe for confusion? 12:00 Q from Flora: how do you find the signal in the noise? 16:30 Q from the comments: how long should you stay loyal to an organisation? 19:30 Q from Ken: will a billion AI ideas drown out the one great human one? 22:30 See you next time Resource: 🎙️ Brian Chesky: AI Founder Mode — Invest Like the Best with Patrick O'Shaughnessy — https://colossus.com/episode/ai-founder-mode/ 📰 Pilita Clark: Why co-CEOs might suit our…

People in this episode

Hosts: Hayaatun, Jimmy

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Mentioned in this episode

Organizations: Airbnb, City AM

Books & works: The Devil Wears Prada 2

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