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—Brought to you by Sidebar—Catalyze your career with a Personal Board of Directors | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Eppo—Run reliable, impactful experiments—Find the full transcript at: https://www.lennyspodcast.com/brian-cheskys-new-playbook/#transcript—Where to find Brian Chesky:• X: https://twitter.com/bchesky• LinkedIn: https://www.linkedin.com/in/brianchesky/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—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—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/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

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