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

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Mar 30, 2023

Guest

Casey Winters

Casey Winters, a legendary advisor in the product and growth space with experience at Airbnb and Eventbrite, shares his insights on breaking free from conventional frameworks. He discusses the pitfalls of the 'zero interest rate phenomenon' for product managers and emphasizes the balance of intuition and expertise in startups. Listeners will learn about leveraging network effects and the challenges of consumer subscriptions, along with Casey's contrarian approach to hiring product managers and thoughts on AI's role in the future of product management.

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insights

INSIGHT

Zero Interest Rate PM

The "zero interest rate phenomenon" describes product managers who rely heavily on resources and frameworks instead of their own judgment.
This over-reliance on research and best practices hinders risk-taking and quick learning through shipping.

insights

INSIGHT

CPO Challenges

The CPO role is challenging, with frequent misalignment with CEOs and shifting business needs.
Success is difficult to maintain, and the role often has a short tenure.

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ADVICE

Focus on Value

For product managers, prioritize learning quickly and trying things out, especially in uncertain environments.
Focus on adding value to customers and the business, using frameworks as tools, not strict guidelines.

Get the Snipd Podcast app to discover more snips from this episode

Navigating the CPO Journey

03:40 • 23min

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Balancing Intuition and Expertise in Startups

26:45 • 12min

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Understanding Network Effects in Business Models

39:11 • 4min

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Marketplace Evolution and Competition Insights

42:45 • 22min

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Navigating Consumer Subscription Challenges

01:04:39 • 9min

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Pop Culture Favorites and Product Development Insights

01:13:48 • 2min

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Musical Recommendations and Podcast Closing Thoughts

01:16:12 • 2min

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• Mentioned in 317 episodes

Thinking, Fast and Slow

Daniel Kahneman

In this book, Daniel Kahneman takes readers on a tour of the mind, explaining how the two systems of thought shape our judgments and decisions. System 1 is fast, automatic, and emotional, while System 2 is slower, effortful, and logical. Kahneman discusses the impact of cognitive biases, the difficulties of predicting future happiness, and the effects of overconfidence on corporate strategies. He offers practical insights into how to guard against mental glitches and how to benefit from slow thinking in both personal and business life. The book also explores the distinction between the 'experiencing self' and the 'remembering self' and their roles in our perception of happiness.

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• Mentioned in 46 episodes

The Goal

Eliyahu M. Goldratt

The book tells the story of Alex Rogo, a factory manager who is given three months to improve his underperforming plant or face its closure. With the guidance of his former physics professor, Jonah, Alex learns to apply the Theory of Constraints to identify and manage bottlenecks in the production process. Through this approach, Alex and his team transform the factory, improving efficiency, reducing inventory, and increasing profitability. The novel uses the Socratic method to teach fundamental business concepts and emphasizes the importance of continuous improvement and critical thinking in management.

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Station Eleven

Emily St John Mandel

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Profit from the Core

A Return to Growth in Turbulent Times

Chris Zook

James Allen

Profit from the Core is based on a ten-year study by Bain & Company of 2,000 companies across various industries. The book argues that many growth strategies fail because companies diversify too far from their core business. Zook and Allen outline three key factors for successful growth strategies: maximizing the core business, expanding into related businesses, and redefining the business before competitors do. The book stresses the importance of 'adjacency expansion' from the core and provides practical advice on how to revitalize and expand a company's core to achieve profitable growth.

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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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Find the full transcript at: Zhttps://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

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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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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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