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: https://www.sidebar.com/lenny/?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=pbod | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc | Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ 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 podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.