Brian Chesky is the co-founder and CEO of Airbnb. Under Brian’s leadership, Airbnb has grown into a community of over 4 million hosts who have welcomed more than 1.5 billion guests across over 220 countries and regions. I had the privilege of working under his leadership, so it is a great honor to have him on the show. We discuss:

• How Airbnb has shifted their thinking on product management

• Why bureaucracy happens in companies, and how to avoid it

• The importance of founders diving into the details

• Why Airbnb moved away from traditional growth channels and what they are doing instead

• Airbnb’s newly released features

• How and why Brian encourages his team to set ambitious goals

• Why he says he still has a lot to prove

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Find the full transcript at: https://www.lennyspodcast.com/brian-cheskys-new-playbook/#transcript

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Where to find Brian Chesky:

• X: https://twitter.com/bchesky

• LinkedIn: https://www.linkedin.com/in/brianchesky/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Brian’s background

(05:18) The current structure of product management at Airbnb

(09:21) How fast-moving companies become slow-moving bureaucracies

(12:20) Brian’s thoughts on performance marketing

(13:50) Airbnb’s rolling two-year roadmap

(15:30) Brian’s journey as CEO in a growing company

(18:34) Best practices for A/B testing

(20:30) Who inspired Airbnb’s new direction

(23:18) The first changes Brian implemented at the onset of the pandemic

(24:51) Why founders should be “in the details”

(30:15) Airbnb’s marketing, communication, and creative functions

(31:38) Advice for founders on how to lead

(34:15) Tips for implementing Airbnb’s business methodology

(38:48) Airbnb’s winter release

(41:47) Why Airbnb no longer has separate guest and host teams

(42:38) Brian’s thoughts on design trends

(45:36) The importance of empowering hosts with great tools

(45:57) How setting ambitious goals improves team performance

(50:05) Tips for preventing burnout

(56:02) Tips for personal and professional growth

(58:19) Why Brian says he still has a lot to prove

(1:02:58) Paying it forward

(1:05:03) A fun fact about Brian

(1:09:26) Airbnb’s origin story

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Referenced:

• Localmind: https://www.crunchbase.com/organization/localmind

• Config 2023 in review: https://www.figma.com/blog/config-2023-recap/

• Why Founders Fail: The Product CEO Paradox: https://techcrunch.com/2013/08/10/why-founders-fail-the-product-ceo-paradox/

• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/

• Jony Ive on Crunchbase: https://www.crunchbase.com/person/jonathan-ive

• Charles Eames: https://en.wikipedia.org/wiki/Charles_Eames

• Airbnb 2023 Winter Release: https://news.airbnb.com/en-in/airbnb-2023-winter-release-introducing-guest-favorites-a-collection-of-the-2-million-most-loved-homes-on-airbnb/

• Airbnb 2023 winter release reel: https://x.com/bchesky/status/1722243847751970861?s=20

• John Wooden’s website: https://coachwooden.com/

• An 85-year Harvard study found the No. 1 thing that makes us happy in life: It helps us ‘live longer’: https://www.cnbc.com/2023/02/10/85-year-harvard-study-found-the-secret-to-a-long-happy-and-successful-life.html

• Sam Altman on X: https://twitter.com/sama

• Alfred P. Sloan: https://en.wikipedia.org/wiki/Alfred_P._Sloan

• Bob Dylan quote: https://quotefancy.com/quote/950807/Bob-Dylan-An-artist-has-got-to-be-careful-never-really-to-arrive-at-a-place-where-he

• OpenAI: https://openai.com/

• Michael Seibel’s website: https://www.michaelseibel.com/

• Y Combinator: https://www.ycombinator.com/

• The Norman Rockwell Museum: https://www.nrm.org/

• Rhode Island School of Design: https://www.risd.edu/

• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/

• Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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Fletch, Vaughan & Hayley's Lil Bitta Pod -15th October, 2025