Brian Chesky’s new playbook

11/12/23 • 73 min

1 Listener

Lenny's Podcast: Product | Growth | Career

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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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

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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:

• 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

—

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:

Previous Episode

Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor, startup advisor)

Ramesh Johari is a professor at Stanford University focusing on data science methods and practice, as well as the design and operation of online markets and platforms. Beyond academia, Ramesh has advised some incredible startups, including Airbnb, Uber, Bumble, and Stitch Fix. Today we discuss:

• What exactly a marketplace is, if you boil it down

• What you need to get right to build a successful marketplace

• How to optimize any marketplace

• An easy litmus test to see if there’s an opportunity to build a marketplace in the space

• The role of data science in successful marketplaces

• Ramesh’s philosophy on experimentation and AI

• Advice on implementing rating systems

• Why learning isn’t free

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Brought to you by Sanity—The most customizable content layer to power your growth engine | Hex—Helping teams ask and answer data questions by working together | Eppo—Run reliable, impactful experiments

—

Find the full transcript at: https://www.lennyspodcast.com/marketplace-lessons-from-uber-airbnb-bumble-and-more-ramesh-johari-stanford-professor-startup/

—

Where to find Ramesh Johari:

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

• Website: https://web.stanford.edu/~rjohari/

• X: https://twitter.com/rameshjohari

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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) Ramesh’s background

(04:31) A brief overview of what a marketplace is

(08:10) The role of data science in marketplaces

(11:21) Common flaws of marketplaces

(16:43) Why every founder is a marketplace founder

(20:26) How Substack increased value to creators by driving demand

(20:58) An example of overcommitting at eBay

(22:24) An easy litmus test for marketplaces

(25:52) Thoughts on employees vs. contractors

(28:02) How to leverage data scientists to improve your marketplace

(34:10) Correlation vs. causation

(35:27) Decisions that should be made using data

(39:29) Ramesh’s philosophy on experimentation

(41:06) How to find a balance between running experiments and finding new opportunities

(44:11) Badging in marketplaces

(46:04) The “superhost” badge at Airbnb

(49:59) How marketplaces are like a game of Whac-A-Mole

(52:41) How to shift an organization’s focus from impact to learning

(55:43) Frequentist vs. Bayesian A/B testing

(57:50) The idea that learning is costly

(1:01:55) The basics of rating systems

(1:04:41) The problem with averaging

(1:07:14) Double-blind reviews at Airbnb

(1:08:55) How large language models are affecting data science

(1:11:27) Lightning round

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Referenced:

• Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/

• Upwork (formerly Odesk): https://www.upwork.com/

• Ancient Agora: https://en.wikipedia.org/wiki/Ancient_Agora_of_Athens

• Trajan’s Market: https://en.wikipedia.org/wiki/Trajan%27s_Market

• Kayak: https://www.kayak.com/

• UrbanSitter: https://www.urbansitter.com/

• Thumbtack: https://www.thumbtack.com/

• Substack: https://substack.com/

Next Episode

The ultimate guide to product operations | Melissa Perri and Denise Tilles

Melissa Perri is the CEO of Produx Labs, a product management training organization; author of the seminal PM book The Build Trap; and a former Harvard Business School professor of product management. Denise Tilles is the CPO at Grocket, Melissa’s colleague at Produx Labs, and a seasoned product leader with over a decade of experience. Together they authored the new book Product Operations: How successful companies build better products at scale. In today’s episode, they share insights, strategies, and real-world experiences to master all things product ops. We discuss:

• What exactly product operations is

• The three pillars of the product ops role

• The biggest benefits of adding product ops to your organization

• Which tasks product managers should offload to product ops and which they need to own

• How to help PMs embrace the value of product ops

• Examples of companies that have implemented product ops well

• Who and how to hire for this role

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This entire episode is brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

—

Find the full transcript at: https://www.lennyspodcast.com/the-ultimate-guide-to-product-operations-melissa-perri-and-denise-tilles/#transcript

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