Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub)

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Casey Winters is a longtime and legendary advisor and operator. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit and until recently was the Chief Product Officer at Eventbrite, where he managed the PM, design, research, and growth marketing teams. Before Eventbrite, he led growth and product teams at Pinterest and Grubhub. In today’s episode, we discuss what Casey calls the “zero interest rate phenomenon” product manager and how to avoid becoming one. He provides valuable insights on thinking outside popular frameworks, shipping products efficiently, and avoiding overreliance on user research. We explore the three types of network effects, how to leverage them, and how to break someone else’s network effect. Finally, Casey shares his contrarian approach to interviewing product managers and his thoughts on the future of PM roles with AI.

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Where to find Casey Winters:

• Twitter: https://twitter.com/onecaseman

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

• Blog: https://caseyaccidental.com/

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Where to find Lenny:

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

• Twitter: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Casey’s background

(03:36) What Casey is up to

(05:24) Why the CPO position is frequently short-lived

(07:26) What Casey learned in his role as CPO of Eventbrite

(10:15) The “zero interest rate phenomenon” product manager

(12:17) Advice for thinking outside common frameworks

(18:35) When to bring in research

(21:16) What Whatnot does

(21:59) Casey’s approach to interviewing PMs 

(23:29) Red flags in interview responses

(24:27) The future of product management with AI

(27:47) Founder intuition vs. team expertise

(33:33) How to influence founders

(37:17) Adding the delivery driver app at Grubhub

(40:00) Network effects

(43:10) Why Zillow is a sticky product

(44:05) How Grubhub’s network effect got taken over by DoorDash and Uber Eats

(51:47) Don’t underestimate the competition

(54:43) SaaS adding marketplace and vice versa

(01:02:30) Defining marketplaces

(1:03:34) What Substack is nailing

(1:05:43) Tips for B2C subscription startups

(1:13:15) Lightning round

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Referenced:

• Casey Winters on Lenny’s Podcast previously: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/

• Whatnot: https://www.whatnot.com/

• The 700-calorie breakfast you should eat if you want to live forever, according to futurist Ray Kurzweil: https://www.businessinsider.com/what-ray-kurzweil-eats-to-live-forever-2016-4

• The Way of the Gun on Hulu: https://www.hulu.com/movie/the-way-of-the-gun-0fc9590c-3f85-48ab-96e9-1da1b9695065

• Notion AI: https://www.notion.so/product/ai

• Zapier: https://zapier.com/

• Founder intuition vs. team expertise vs. customer expertise: https://caseyaccidental.com/founder-intuition-team-expertise/

• Erika Warren on LinkedIn: https://www.linkedin.com/in/erika-warren/

• Alyssa Ravasio (Hipcamp) on LinkedIn: https://www.linkedin.com/in/alyssa-ravasio-23114717/

• Marketplace supply strategy: comprehensive, exclusive, or curated: https://a16z.com/2021/03/31/marketplace-supply-strategy/

• Nassim Taleb on Twitter: https://twitter.com/nntaleb

• The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244

• OpenTable: https://www.opentable.com/

• Booking.com: https://www.booking.com/

• Faire: https://www.faire.com/

• How to increase your retention: https://www.lennysnewsletter.com/p/how-to-increase-your-retention-issue

• The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/r

• Profit from the Core: A Return to Growth in Turbulent Times: https://www.amazon.com/Profit-Core-Return-Growth-Turbulent/dp/1422131114/

• Party Down on Starz: https://www.starz.com/us/en/series/party-down/2011

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Station Eleven on HBO Max: https://www.hbomax.com/series/urn:hbo:series:GYZWoOQ6F9cLDCAEAAABP

• Kicking and Screaming on Netflix: https://www.netflix.com/title/70052286

• Raven by Kelela on Spotify: https://open.spotify.com/album/06uhdSmIYrWRkdnAPjcRcT

• Optical Delusion by Orbital on Spotify: https://open.spotify.com/album/2jQbFspnSh7erex6RDKQGJ

• Stakes Is High by De La Soul on Spotify: https://open.spotify.com/album/3jlC2uhYNrhikZXLviEnpu

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