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Brian Chesky’s new playbook

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.

Brian CheskyguestLenny Rachitskyhost
Nov 11, 20231h 13mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Brian Chesky reveals Airbnb’s radical product, org, and growth reboot

  1. Brian Chesky explains how Airbnb overhauled product management, collapsing PM and product marketing into a smaller, more senior, story- and distribution-focused function while offloading program management to true program managers.
  2. He describes shifting Airbnb from a divisional, politics-prone structure to a highly functional, CEO-in-the-details model with a single, rolling two‑year roadmap and twice‑yearly, company-wide launches.
  3. Chesky outlines a growth strategy that deemphasizes dependence on performance marketing in favor of building standout products, tightly integrating marketing and engineering, and educating customers on new features.
  4. He also shares his views on ambitious goal-setting, avoiding burnout, nurturing relationships, and maintaining a beginner’s mindset to keep up with the company’s evolving scale.

IDEAS WORTH REMEMBERING

5 ideas

Unify product and marketing ownership to ensure both great products and great storytelling.

Airbnb merged inbound PM responsibilities with outbound product marketing so the same leaders understand the product, the customer, and the go-to-market story—closing the common gap where teams ship features no one hears about or adopts.

Adopt a functional, not divisional, structure to reduce politics and bureaucracy.

Chesky dismantled multiple business-line divisions (e.g., separate guest/host teams) in favor of core functions—design, engineering, product marketing, marketing, etc.—all aligned to a single company-wide roadmap to keep everyone rowing in the same direction.

Create one rolling, long-range roadmap and anchor execution to a clear launch cadence.

Airbnb runs on a rolling two‑year product strategy updated every six months, with major launches twice a year; this concentrates focus, forces tradeoffs, and makes it easier for the entire organization to coordinate around coherent, customer-facing releases.

Founders should stay deeply in the product details without slipping into command‑and‑control micromanagement.

Chesky argues that responsible leadership means regularly reviewing work, understanding nuances, and unblocking teams—similar to how a board probes a CEO—rather than outsourcing product judgment entirely or merely ‘empowering’ people without true oversight.

Use growth channels selectively; let product excellence and education do more of the work.

While Airbnb still uses performance marketing, Chesky reframed it as a precise ‘laser’ rather than the primary growth engine, emphasizing brand, product marketing, and education about new features as longer-term, compounding advantages.

WORDS WORTH SAVING

5 quotes

Way too many founders apologize for how they wanna run the company.

Brian Chesky

You can't build a product unless you know how to talk about the product.

Brian Chesky

Leaders are in the details… If you don't know the details, how do you know people are doing a good job?

Brian Chesky

We wanted a company where 1,000 people could work but it looked like 10 people did it.

Brian Chesky

I still feel like I have a lot to prove. I haven't made it yet.

Brian Chesky

Redefining the product management function at Airbnb (PM + product marketing + program management split)Transition from divisional structure to a functional, founder-led organization with one roadmapNew product development and launch cadence, including Airbnb’s guest favorites and listing tabPhilosophy on leadership: ‘leaders are in the details’ vs. micromanagementShifting growth strategy away from heavy performance marketing toward product- and brand-led growthSetting highly ambitious goals (‘add a zero’) and pacing the organizationPersonal practices: managing burnout, relationships, and continuous learning as a founder-CEO

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