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  1. Masters of Scale
  2. Airbnb’s bet on an IRL future, with Brian Chesky
Airbnb’s bet on an IRL future, with Brian Chesky

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale · Oct 14, 2025

Airbnb CEO Brian Chesky on AI's rise, the need for real connection, and leading with principle in a volatile, politically charged world.

The Key Entrepreneurial Question Is "What Unique Contribution Disappears If We Don't Exist?"

Beyond finding a market gap, leaders should ask what unique imprint their company leaves on the world. The most powerful justification for a company's existence is providing an essential contribution that no one else would. This reframes the mission from a business goal to an indispensable purpose.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Airbnb's Brian Chesky: Social Media "Uninvented" Social Networking, Replacing Intimacy With Performance

The internet's evolution from social networking (connecting with friends) to social media (broadcasting to followers) destroyed a valuable product category. This shift replaced genuine intimacy with performance, contributing to a global rise in loneliness and isolation as people stare at screens instead of connecting.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Airbnb's CEO: Differentiate Between Business Decisions (to win) and Principle Decisions (to be remembered)

A business decision aims to gamify and optimize a specific outcome. A principle decision is based on core values, made without knowing the outcome, to be remembered favorably regardless of the result. Sticking to principles may mean losing a short-term battle but ultimately wins the war by building trust.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Airbnb CEO Brian Chesky Bets on "Real" Experiences as an Antidote to an AI-Generated World

As AI makes digital content increasingly artificial and indistinguishable from reality, the value of authentic, in-person human connection will skyrocket. The most powerful counter-position to the AI trend isn't less technology, but rather using technology to facilitate more tangible, "real" world interactions.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Airbnb CEO: Design Is Deeply Understanding a System's Essence, Not Just Its Look and Feel

True design isn't about aesthetics; it is the fundamental soul of a creation, revealed by how it works. It requires distilling a product or company to its simplest form through profound understanding. As AI automates coding, this ability to design systems becomes a critical skill for everyone, not just designers.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Anchor Company Values on 20-Year Truths to Avoid Political Whiplash, Advises Airbnb's CEO

Political and social climates are prone to volatile swings. Instead of reacting to short-term trends (e.g., DEI focus vs. rollback), leaders should define their company by core principles that will remain true in two decades. This provides stability and authenticity, making everything else just a fleeting trend.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago

Real AI Revolution Begins When Consumer Apps Fundamentally Change, Not Just Back-End Tech

Despite the hype, AI's impact on daily life remains minimal because most consumer apps haven't changed. The true societal shift will occur when new, AI-native applications are built from the ground up, much like the iPhone enabled a new class of apps, rather than just bolting AI features onto old frameworks.

Airbnb’s bet on an IRL future, with Brian Chesky thumbnail

Airbnb’s bet on an IRL future, with Brian Chesky

Masters of Scale·4 months ago