Lenny's Podcast: Product | Growth | Career Lenny Rachitsky

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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: https://www.lennyspodcast.com/thinking-beyond-frameworks-casey-winters-pinterest-eventbrite-airbnb-tinder-canva-reddit-grubhub/
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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: http

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Kevin Aluwi is the co-founder and former CEO of Gojek. With over 2.7 million drivers and over 3 billion orders completed, Gojek is the biggest startup in Indonesia and all of Southeast Asia. In today’s podcast, Kevin shares the story of how Gojek overcame endless obstacles—including being underfunded, being unable to send drivers payment, and the local motorcycle mafia coming after their drivers. We cover the importance of brand, the value of doing the hard things, how to be super-scrappy, and helpful tips on building a tech company outside of Silicon Valley.

Find the full transcript at: https://www.lennyspodcast.com/taxi-mafias-cash-vaults-and-100-mom-growth-the-story-behind-southeast-asias-biggest-startup-kevin-aluwi-gojek/#transcript

Where to find Kevin Aluwi:
• Twitter: https://twitter.com/kaluwi
• LinkedIn: https://www.linkedin.com/in/kaluwi/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:
• Gojek: https://www.gojek.com/en-id/
• WeChat: https://www.wechat.com/
• Sequoia: https://www.sequoiacap.com/
• eFishery: https://efishery.com/en/
• What You Do Is Who You Are: How to Create Your Business Culture: https://www.amazon.com/What-You-Do-Who-Are/dp/0062871331
• How Brands Grow: What Marketers Don’t Know: https://www.amazon.com/How-Brands-Grow-What-Marketers/dp/0195573560/
• The Menu on HBO: https://www.hbo.com/movies/the-menu
• Cyberpunk Edgerunners on Netflix: https://www.netflix.com/title/81054853
• Arc: https://arc.net/
• Steam Deck: https://store.steampowered.com/steamdeck

In this episode, we cover:
(00:00) Kevin’s background
(05:00) How Gojek got started and the current scale
(08:35) Some of the services that Gojek currently offers or has offered
(09:37) Kevin’s thoughts on super-apps
(15:36) The importance of brand
(23:08) How to create branding with consistency across copy and design
(26:53) Challenges Gojek had in the early days that required scrappiness
(33:03) Why Kevin doesn’t believe in moats as a durable solution, and the value of doing hard things
(37:30) How Gojek hired private security to keep their drivers safe
(39:38) The value of founders doing and understanding multiple roles within the company
(44:12) How Kevin’s failed finance career led him to take a bet on building tech in Indonesia
(47:30) Tips on building a tech company outside of Silicon Valley 
(52:09) What the market is like in Indonesia 
(55:42) What’s next for Kevin
(57:41) Lightning round

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


Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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Lulu Cheng Meservey was formerly head of comms at Substack (where I host my newsletter and podcast) and is currently the Executive Vice President of Corporate Affairs and Chief Communications Officer at Activision Blizzard. She also writes one of my favorite newsletters, “Flack,” where she shares tactical advice for company comms, PR, and messaging. In today’s episode, we dive deep into the world of PR and comms. We discuss why taking risks is crucial, how to gain attention as an underdog, and why it’s important to have a super-specific audience. Lulu outlines several frameworks I’d never heard of before, including a concentric circles framework for identifying your audience, the cultural erogenous zones, and even a physics-based framework for comms.

Find the full transcript at: https://www.lennyspodcast.com/navigating-comms-and-pr-lulu-cheng-meservey-substack-activision-blizzard/#transcript

Where to find Lulu Cheng Meservey:
• Twitter: https://twitter.com/lulumeservey
• LinkedIn: https://www.linkedin.com/in/lulu-cheng-meservey/
• Newsletter: https://www.getflack.com/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:
• “Binders full of women”: Mitt Romney’s four words that alienated women voters: https://www.theguardian.com/world/shortcuts/2012/oct/17/binders-full-of-women-romneys-four-words
• Bill Bishop’s newsletter on Substack: https://www.sinocism.com/
• Hamish McKenzie on Twitter: https://twitter.com/hamishmckenzie
• The Network State: How to Start a New Country: https://www.amazon.com/Network-State-How-Start-Country-ebook/dp/B09VPKZR3G
• How to increase virality: https://www.lennysnewsletter.com/p/increasing-virality
• Ryan Petersen on Twitter: https://twitter.com/typesfast
• Brian Armstrong on Twitter: https://twitter.com/brian_armstrong
• Palmer Luckey on Twitter: https://twitter.com/PalmerLuckey
• Pirate Wires: https://www.piratewires.com/
• NYX: https://www.nyxcosmetics.com/
• Gates of Fire: An Epic Novel of the Battle of Thermopylae: https://www.amazon.com/Gates-Fire-Novel-Battle-Thermopylae/dp/055338368X
• The Last of Us on HBO: https://www.hbo.com/the-last-of-us
• Notion: https://www.notion.so/
• Lex: https://lex.page/

In this episode, we cover:
(00:00) Lulu’s background
(04:36) What helps an idea spread
(06:17) Mitt Romney’s “binders full of women”
(07:19) Advice for coming up with contagious phrasing
(08:36) Lulu’s esoteric reference that left her Twitter followers confused
(11:08) The importance of taking risks, and Lulu’s thread on standing for free speech
(12:53) An example of another sticky phrase
(14:40) The cultural erogenous zones framework
(16:08) How Kamala Harris made people care about education
(17:29) How to get attention as the underdog
(20:25) How Substack used the concentric circles framework to spread information
(21:32) Understanding the layers in those concentric circles
(25:44) How to get started figuring out your concentric circles
(27:03) An example of aligning messaging with people’s values 
(28:19) Lulu’s mathematical formula framework for comms for a purpose
(28:54) A physics-based framework for comms
(35:56) How Balaji Srinivasan used the concentric circles approach with his book The Network State
(39:46) The importance of a super-specific audience
(41:12) Reasons your comms are failing
(42:40) Why you should focus on one direct communication channel at first
(46:58) Why not every founder needs to be on Twitter
(48:02) Who LinkedIn works better for
(49:23) Examples of messaging with a human voice and hopping on trends quickly
(51:11) Reasons for direct comms 
(53:52) How to get started s

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Josh Miller is the CEO and co-founder of The Browser Company, where he helped build Arc, my go-to web browser. In today’s episode, we get an inside look at the unique structure and values of The Browser Company and how their company culture has helped them land some of the best talent in tech. Josh shares ways that his company embraces experimentation, including their “optimizing for feelings” approach to building, and explains why extreme transparency is at the forefront of everything they do.
Special invite link to skip the waitlist: https://arc.net/gift/lenny

Find the full transcript at: https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/#transcript

Where to find Josh Miller:
• Twitter: https://twitter.com/joshm
• LinkedIn: https://www.linkedin.com/in/josh-miller-b31259106/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:
• Early access to Arc: https://arc.net/gift/lenny
• The Browser Company: https://thebrowser.company/
• Arc: https://arc.net/
• Hursh Agrawal on LinkedIn: https://www.linkedin.com/in/hurshagrawal/
• Hacker News: https://news.ycombinator.com/
• Scott Belsky on LinkedIn: https://www.linkedin.com/in/scottbelsky/
• Notes on Roadtrips: https://thebrowser.company/values/
• Shahed Khan on Twitter: https://twitter.com/_shahedk
• Paper by FiftyThree:  https://www.hellobrio.com/blog/digital-drawing-paper-fiftythree
• Vimeo: https://vimeo.com/
• Peter Vidani on Twitter: https://twitter.com/pter
• The Verge: https://www.theverge.com/
• Ellis Hamburger on LinkedIn: https://www.linkedin.com/in/ellishamburger/
• Airbnb’s Snow White project: https://uxdesign.cc/how-airbnb-proved-that-storytelling-is-the-most-important-skill-in-design-15d04ac71039
• General Magic: https://www.generalmagicthemovie.com/
• Linear: https://linear.app/
• Raycast: https://www.raycast.com/
• Cron: https://cron.com/
• Thrive Capital: https://thrivecap.com/
• Tuple: https://tuple.app/
• Figma: https://www.figma.com/
• Harold and the Purple Crayon: https://www.amazon.com/Harold-Purple-Crayon-Crockett-Johnson/dp/0062086529
• Seeing Is Forgetting the Name of the Thing One Sees: https://www.amazon.com/Seeing-Forgetting-Name-Thing-Sees/dp/0520256093/
• God Save Texas: A Journey into the Soul of the Lone Star State: https://www.amazon.com/God-Save-Texas-Journey-State/dp/0525520104
• The Last of Us on HBO: https://www.hbo.com/the-last-of-us
• Adam Curtis documentaries on YouTube: https://www.youtube.com/playlist?list=PLStWlBRkr0N_aYjPmbrrjm_rsstpkUBLc
• Notion: https://www.notion.so/

In this episode, we cover:
(00:00) Josh’s background
(03:56) Arc and the metrics they use to track growth
(04:42) Arc’s retention numbers
(08:22) Josh’s product-building philosophy and why he believes in optimizing for feelings
(18:57) How The Browser Company’s values create a culture that allows them to ship so quickly
(22:46) The “Notes on Roadtrips” doc about values
(27:48) How Josh is able to hire such amazing talent
(37:29) The good and bad of building in public
(45:16) Some of the odd teams at The Browser Company and why Josh calls it a prototype-driven culture
(46:01) The membership team
(48:07) The storytelling team
(52:00) Why The Browser Company doesn’t have traditional PMs
(54:07) A case for adding PMs
(57:32) The role of data, even in a company that optimizes for feelings
(58:30) Airbnb’s Snow White project
(1:02:14) How impactful moments in Josh’s life influenced values at The Browser Company
(1:03:08) How the film General Magic has inspired Josh
(1:04:32) The value of novel names
(1:06:50) Why T

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Christina Wodtke is an author, Stanford University professor, and speaker who teaches strategies for building high-performing teams. She’s also the author of Radical Focus, which some consider the de facto guide to OKRs. In today’s episode, we dive into OKRs and how they can be used to help your team achieve better results. Christina shares her expertise on crafting OKRs, how she uses them in her personal life, and common mistakes you should avoid when you sit down to write your own. She discusses effective goal setting and outlines a systematic approach to achieving key results. Finally, Christina gives some specific tips on how to improve your storytelling and drawing skills and explains why it’s smart to set ambitious goals.

Find the full transcript here: https://www.lennyspodcast.com/the-ultimate-guide-to-okrs-christina-wodtke-stanford/

Where to find Christina Wodtke:
• Twitter: https://twitter.com/cwodtke
• LinkedIn: https://www.linkedin.com/in/christinawodtke/
• Website: https://eleganthack.com/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:
• OKR worksheet template: http://eleganthack.com/wp-content/uploads/2022/03/OKR_Worksheet.pdf
• Yahoo’s peanut butter memo: https://www.wsj.com/articles/SB116379821933826657
• The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756/
• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006087
• Pencil Me In: https://www.amazon.com/Pencil-Me-Christina-Wodtke-ebook/dp/B075Z8J35G?
• The Back of the Napkin: Solving Problems and Selling Ideas with Pictures: https://www.amazon.com/Back-Napkin-Expanded-Problems-Pictures/dp/1591842697/ref=sr_1_1
• The Minto Pyramid Principle: https://www.barbaraminto.com/
• Lane Shackleton’s guest post on Lenny’s Newsletter: https://www.lennysnewsletter.com/p/how-coda-builds-product
• The Product Trio by Teresa Torres: https://www.producttalk.org/2021/05/product-trio/
• Ken Norton’s website: https://www.bringthedonuts.com/about/
• The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth: https://www.amazon.com/Fearless-Organization-Psychological-Workplace-Innovation/dp/1119477247
• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X/
• Cloud Atlas: https://www.amazon.com/Cloud-Atlas-Novel-David-Mitchell/dp/0375507256
• Black Panther: Wakanda Forever: https://www.imdb.com/title/tt9114286/
• The Team That Managed Itself: A Story of Leadership: https://www.amazon.com/Team-that-Managed-Itself-Leadership-ebook/dp/B07ZG5Y689

In this episode, we cover:
(00:00) Christina’s background
(04:54) How Christina uses OKRs to manage her personal life
(07:42) The purpose of OKRs
(16:15) Mission, vision, roadmaps, and OKRs
(20:57) How strategy ties in
(22:39) Why OKRs should be kept simple, and the ideal way to express key results
(23:45) The importance of customer satisfaction and why you need a qualitative researcher
(24:58) Common mistakes people make when writing OKRs
(26:14) An example of writing OKRs for an online magazine about interior design
(29:28) The importance of repetition
(33:17) The 5 whys
(36:40) Why you should start OKRs with your best multi-disciplinary team
(38:44) Christina’s book, Radical Focus
(40:26) The importance of storytelling and drawing (even badly!)
(43:21) Tips to become a better storyteller
(44:29) Using the Minto method for storytelling
(46:02) The cadence of OKRs and the importance of celebrations

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Aarthi Ramamurthy and Sriram Krishnan are founders, angel investors, and product leaders who host the podcast Aarthi and Sriram’s Good Time Show. They have both held leadership roles at major technology companies including Meta, Twitter, Snap, Microsoft, and Netflix. In today’s episode, we dive into how and why to build your personal brand, how to deal with impostor syndrome, and stories from Aarthi’s time at Clubhouse and Sriram’s time working with Zuck. Aarthi and Sriram share their lessons from past failures, their experience building communities, and their techno-optimism, and Sriram offers his hot take on the Jobs to Be Done framework.

Find the full transcript at: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/#transcript

Where to find Sriram Krishnan and Aarthi Ramamurthy:
• Aarthi’s Twitter: https://twitter.com/aarthir
• Sriram’s Twitter: https://twitter.com/sriramk
• Good Time Show Twitter: https://twitter.com/aarthisrirampod
• Good Time Show website: https://www.aarthiandsriram.com/

Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:
• Naval Ravikant on Twitter: https://twitter.com/naval
• Marc Andreessen on Twitter: https://twitter.com/pmarca
• Clubhouse: https://www.clubhouse.com/
• Eugene Wei’s Status as a Service: https://www.eugenewei.com/blog/2019/2/19/status-as-a-service
• Kylie Jenner on Snapchat: https://www.snapchat.com/add/kyliejenner
• The Rock on Instagram: https://www.instagram.com/therock/
• Cristiano Ronaldo on Instagram: https://www.instagram.com/cristiano
• Charli D’Amelio on TikTok: https://www.tiktok.com/@charlidamelio
• Addison Rae on TikTok: https://www.tiktok.com/@addisonre
• The founder of TikTok’s speech: https://ludlow.notion.site/Alex-Zhu-TikTok-4631f80fdcc4423a845e145e807d8e2b
• Naval’s network tweet: https://twitter.com/naval/status/847134295600746496?lang=en
• Y Combinator: https://www.ycombinator.com/
• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth
• Hunter Walk on impostor syndrome: https://hunterwalk.com/2023/03/01/imposter-syndrome-is-definitely-misnamed-might-be-a-condition-of-privilege-has-a-fascinating-history/
• On Reviews: https://boz.com/articles/reviews
• Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90
• First-principles thinking: https://fs.blog/first-principles/

In this episode, we cover:
(00:00) Sriram and Aarthi’s backgrounds
(04:16) How Sriram and Aarthi got Elon Musk on their podcast
(08:47) Reflections on Clubhouse and other social networks
(14:14) Why Aarthi and Sriram are optimistic about tech
(25:53) Why you should put yourself out there and build your personal brand
(27:09) Why you should build a network with authentic relationships, and how to do it
(28:56) Sriram’s curated communities
(31:20) What you need to get right when starting a community
(38:35) Why everyone who wants to should create content
(44:22) Why you shouldn’t try to project expertise when you’re still learning
(47:54) Dealing with impostor syndrome, and why you should lean into your strengths
(54:01) Transitioning to a role of authority
(57:30) What Sriram learned about effective management from Mark Zuckerberg
(1:01:20) The biggest failure Aarthi had, and why you shouldn’t fall for fads
(1:02:08) Sriram’s lesson from building mobile
(1:09:21) Why Sriram hates the Jobs to Be Done framework
(1:18:06) Advice for immigrants

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


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