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 · host Boxlight Creative Studio

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 tumultuous times (FT / Irish Times) — https://www.irishtimes.com/business/2026/05/04/why-co-ceos-might-suit-our-tumultuous-times/ 📖 Reid Hoffman: Tours of Duty — The New Employer-Employee Compact (HBR) — https://hbr.org/2013/06/tours-of-duty-the-new-employer-employee-compact Episodes mentioned: ▶️ Mark Read — Leading 22,000 Employees Who Bet Against You: https://youtu.be/O6oWoVf5X3I ▶️ Natasha Frangos — The Imposter Feeling Every Leader Faces: https://youtu.be/a9AHf_pMHgg ▶️ Sharon White — Why The Best Leaders Are Impossible to Read: https://youtu.be/JluTfnfJYD4 📧 Send us thoughts and questions at [email protected] 💼 Follow us on socials!: Instagram: https://www.instagram.com/whatwedontknow.pod/ LinkedIn: https://www.linkedin.com/company/what-we-dont-know-podcast/ Jimmy's LinkedIn: https://www.linkedin.com/in/jimmy-mcloughlin-obe/ Hayaatun's LinkedIn: https://www.linkedin.com/in/hayaatun/ Credits: Producer: Sunny Winter Producer: Thuy Dong Producer: Jimmy McLoughlin OBE Learn more about your ad choices. Visit podcastchoices.com/adchoices

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This episode was published on May 13, 2026.

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