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Blitzscaling 18: Brian Chesky on Launching Airbnb and the Challenges of Scale

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Key ideas

Chesky traces Airbnb from repeated failed launches to global scale, teaching that founders should win 100 devoted users first, then relearn the job as each stage changes it.

From a machine transcript of the audio. Quotes link to the moment they are said.

  1. 1

    Stay alive long enough to learn

    Chesky recounts launching three times, being passed over by the angels he approached, carrying credit card debt, and funding the company with about $30,000 of novelty cereal. He says the first thing Y Combinator gave the founders was a structure to work on it full time and live together, and he calls the rest of life the enemy of a startup.

  2. 2

    Design past what users expect

    Chesky passes on Paul Graham's advice that 100 people who love you beat a million who sort of like you, which led the founders to go door to door and live with hosts in New York. His seven-star exercise imagines an experience at absurd levels of service, then works back to something slightly beyond expectations that the company could actually do.

  3. 3

    Open cities in person, not by partnership

    Chesky says growth came mainly from word of mouth and press, helped by targeting events. The team went city by city holding host meetups and giving tips, and he reports hosts became more engaged after meeting the founders. He says the partnerships he tried at this stage went nowhere.

  4. 4

    Expect existential threats once it works

    Chesky describes the 2011 European clone as a threat to the whole company, since a travel site without Europe has no reason to exist. He chose not to buy it, trained country managers in San Francisco and opened offices quickly. With regulators, he moved from rallies to meeting those most opposed to Airbnb, aiming for understanding rather than affection.

  5. 5

    Expect a different job every stage

    Chesky says that after product-market fit he went from doing everything but code to mostly hiring, managing and setting the vision, with no idea at first how to manage anyone. To keep up, he recommends going to the definitive source on each topic, such as one book on management, and being shameless about asking experts.

In Brian’s words

“The five star is what people expect. But to build something people love, you almost need to do something more than they expect.”
Brian Chesky·Blitzscaling 18: Brian Chesky on Launching Airbnb and the Challenges of Scale·Watch at 34:51(opens the original in a new tab)
“partnerships in your early stage company, I found, never work because there's so much red tape and paper that by the time you ever get done, you're, like, dead.”
Brian Chesky·Blitzscaling 18: Brian Chesky on Launching Airbnb and the Challenges of Scale·Watch at 28:37(opens the original in a new tab)
“The job changes so much, you're almost playing a different sport at every job.”
Brian Chesky·Blitzscaling 18: Brian Chesky on Launching Airbnb and the Challenges of Scale·Watch at 58:12(opens the original in a new tab)

About this entry

Published
Nov 30, 2015
Channel
Greylock
Type
Video
Length
1:38:29
Language
English
Added
Nov 2, 2026
Source last checked
Nov 2, 2026
Getting startedFundraisingGrowthLeadership

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