Brian Chesky

2 statements across 2 episodes · 1 bullish · 1 bearish · 2 people on the record · first statement Mar 3, 2020 by Mike Maples Jr. · said 39 times in 8 episodes since 2020 · across every show →

Mentions by year

brought up most by Alfred Lin (16), Mike Maples Jr. (7), Ryan Petersen (6), Shane Parrish (5), Neil Pasricha (3), Garry Tan (2)

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2025 29 mentions in 6 episodes 5 per episode
2022 3 mentions in 1 episode
2020 7 mentions in 1 episode

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Everything said about Brian Chesky, oldest first

Mar 3, 2020 positive
Insight
Maples: An earned secret is a counterintuitive insight discovered through direct work
“So it's basically Some work that you did to discover something that most people would think is non-intuitive.”
Mike Maples Jr. Mar 3, 2020 ▶ 39:34 #77 Mike Maples: Living in the Future
Aug 5, 2025 negative
Opinion
Brian Chesky's founder involvement rule does not scale for Flexport
“I think he says like, if the company should only do as many things as the founder can be personally involved in, it's a nice ideal. It doesn't work at my company. We're like in all these different countries and all these different modes of transport that like …”
Ryan Petersen Aug 5, 2025 ▶ 57:15 Ryan Petersen: Building Flexport
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