Brought to you by Superhuman—The fastest email experience ever made | Microsoft Clarity—See how people actually use your product | Eppo—Run reliable, impactful experiments—Nikhyl Singhal is VP of Product at Meta, overseeing teams building messaging, groups, stories, and the main Facebook feed. Before that, he served as the Chief Product Officer at Credit Karma and held various leadership roles at Google, leading teams on Google Photos and Google Hangouts. Nikhyl was also co-founder of three startups, including SayNow and Cast Iron Systems, which were acquired by Google and IBM, respectively. Alongside his successful career, he is passionate about coaching and mentoring, sharing his knowledge through the Skip podcast, newsletter and CPO community. In this episode, we discuss:• Finding your North Star and building a long and meaningful career• Why your superpower may actually be holding you back• Wisdom for aspiring product managers in the early stages of their career• Reasons you aren’t getting promoted, and advice on what to change• How to avoid short-term thinking early in your career and how to become a better manager long-term• Signs you work at an “ex-growth” company and that it’s time to leave• Signs the IC path is a reasonable pursuit• The importance of finding a community—Find the transcript at: https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career—Where to find Nikhyl Singhal:• Twitter: https://twitter.com/nikhyl• LinkedIn: https://www.linkedin.com/in/nikhyl/• Newsletter: https://theskip.substack.com/• Podcast: https://www.skip.community/• Skip CPO Community: https://www.linkedin.com/company/skip-community-for-cpos/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Nikhyl’s background(04:37) Nikhyl’s mentoring approach during critical periods of change(07:07) The power of long-term career planning(10:36) The value of gaining varied experiences rather than merely collecting logos on your resume(12:52) The unique benefits of working at a “MAGMA” company(14:50) Ex-growth companies and the impact of 0% interest rates(20:19) Signs your company may be struggling to find the right product-market fit(21:32) When you should stay at an ex-growth company(22:34) Early career advice for product managers(25:25) Mid-career strategies for promotion(29:47) Summarizing the 4 reasons you may not be getting promoted(30:15) The value of authentic feedback(33:29) Tactical tips for getting better feedback(34:46) Addressing management challenges in tech(39:50) Opportunities for those who prefer the IC path(45:25) How to become a better manager through community building(47:40) Nikhyl’s community, The Skip(51:27) Lenny’s Slack community(52:54) Late-career advice and identifying skills that need reshaping(57:07) Why it’s so important to listen to contradictory feedback(59:45) Nikhyl’s “superpower” and “shadow”(1:02:20) Mental health challenges and the third act of your career(1:08:44) Examples of North Star metrics in the third act of your career(1:12:20) Lightning round—Referenced:• Annie Pearl on Lenny’s Podcast: https://www.lennyspodcast.com/behind-the-scenes-of-calendlys-rapid-growth-annie-pearl-cpo/• The Skip podcast episode about ex-growth companies: https://www.skip.community/should-i-join-or-leave-an-x-hypergrowth-company/• Jules Walter on Lenny’s Podcast: https://www.lennyspodcast.com/leveraging-mentors-to-uplevel-your-career-jules-walter-youtube-slack/• Skip Community for CPOs on LinkedIn: https://www.linkedin.com/company/skip-community-for-cpos/• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986/• Leadership and Self-Deception: Getting Out of the Box: https://www.amazon.com/Leadership-Self-Deception-Getting-Out-Box/dp/B07H3G1KCN• Rise on Disney+: https://www.disneyplus.com/movies/rise/6Yv1uRnw2uAJ• Arc browser: https://arc.net/• Josh Miller (CEO of The Browser Company) on Lenny’s Podcast: https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Miro—A collaborative visual platform where your best work comes to life | Mixpanel—Product analytics that everyone can trust, use, and afford | Lenny’s Job Board—Hire the best product people. Find the best product gigs—Jeremy Henrickson is Rippling’s SVP of Product, responsible for scaling their product and design team across three continents. Previously, as Chief Product Officer at Coinbase, he oversaw 10x growth of the product and engineering organization and transformed a scrappy startup into a global cryptocurrency platform with tens of millions of users. He began his career at Apple in the 1990s and holds a BS and MS in computer science from Stanford. In today’s episode, we discuss:• Strategies for sustaining focus and momentum at scale• The case against MVPs• The problem with frameworks• “Compound startups” and how this influences Rippling’s product development process• Advice for founders wanting to move faster• Why you don’t understand your product unless you’re “in the weeds”• Hiring practices at Rippling and how young PMs can build fruitful careers—Find the transcript at: https://www.lennysnewsletter.com/p/moving-fast-and-navigating-uncertainty—Where to find Jeremy Henrickson:• Twitter: https://twitter.com/jeremyhenricks• LinkedIn: https://www.linkedin.com/in/jeremyhenrickson/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Jeremy’s background(03:24) What it was like leading product teams at Coinbase during the crypto boom(05:25) How Jeremy kept teams focused and the biggest challenges he faced at Coinbase(07:35) Advice for going through intense periods at work(08:52) Maintaining velocity at scale(12:07) An example of small teams with clear missions(14:29) A model for building products(18:03) Jeremy’s thoughts on MVPs (minimum viable products)(22:26) Designing for the most complex use case first(23:17) What a compound startup is and how it works at Rippling(27:09) Rippling’s unique culture of fast decision-making(28:14) Rippling’s leadership values(32:13) Advice for cultivating fast-decision-making teams(33:44) How deep-level thinking and working on the ground helped Rippling expand to other countries(38:42) Why product leaders need to be right(40:42) How Rippling decided where to expand to first(42:29) The case for expanding internationally before you think you’re ready(45:32) Why Jeremy isn’t a huge fan of frameworks(48:08) The differences between building product at Rippling and Coinbase(52:49) How Jeremy hires PMs at Rippling(58:29) Advice for junior PMs(1:00:19) Lessons from working with a founder who has strong opinions about what the product should be(1:02:15) Lightning round—Referenced:• Coinbase: https://www.coinbase.com/• Ethereum: https://ethereum.org/en/• Parker Conrad on Twitter: https://twitter.com/parkerconrad• Rippling: https://www.rippling.com/• Excellent Advice for Living: Wisdom I Wish I’d Known Earlier: https://www.amazon.com/Excellent-Advice-Living-Wisdom-Earlier/dp/0593654528• Matt MacInnis on Twitter: https://twitter.com/stanine• Rippling’s leadership principles: https://www.rippling.com/life• Airbnb cereal story: https://www.cnbc.com/2023/04/18/airbnb-ceo-says-he-wooed-first-investors-with-boxes-of-cereal.html• Guidewire: https://www.guidewire.com/• Jira: https://www.atlassian.com/software/jira• Kyle Boston on Twitter: https://twitter.com/KyleB• Quicksilver (book one of the Baroque Cycle series:) https://www.amazon.com/Quicksilver-Baroque-Cycle-Vol-1/dp/0060593083/r• Consider Phlebas (book 1 of The Culture series): https://www.amazon.com/Consider-Phlebas-Culture-Iain-Banks/dp/031600538X/• The Last of Us on HBO: https://www.hbo.com/the-last-of-us• The Game on Paramount+: https://www.paramountplus.com/shows/the-game-2021/• Tenet: https://www.imdb.com/title/tt6723592/• Corsair H60 CPU cooler: https://www.amazon.com/CORSAIR-Hydro-Liquid-Cooler-Radiator/dp/B00A0HZMGA• Focal Bathys headphones: https://www.amazon.com/Focal-Over-Ear-Bluetooth-Headphones-Cancelation/dp/B0B93YKQT3• Pandemic: https://www.amazon.com/Z-Man-Games-ZM7101-Pandemic/dp/B00A2HD40E• Gloomhaven: https://www.amazon.com/Cephalofair-Games-CPH0201-Gloomhaven/dp/B01LZXVN4P—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Microsoft Clarity—See how people actually use your product | Lenny’s Job Board—Hire the best product people. Find the best product gigs | Eppo—Run reliable, impactful experiments—Nancy Duarte is the CEO of Duarte Inc. and has helped create over 250,000 presentations for influential business leaders across the globe, including Apple, TED, the World Bank, and Al Gore’s An Inconvenient Truth. She’s also written six best-selling books, and her TED talk has garnered over 3 million views. She regularly contributes to HBR, MIT-Sloan, and Forbes, and her books are essential reading in leading business schools worldwide. In today’s episode, we discuss:• Why empathy is at the heart of everything Nancy does• Why you’re presenting more often than you think• Tactics for creating interesting presentations and telling better stories• The concept of a “torchbearer leader” and why it’s important• Strategies for overcoming stage fright and nerves• Tips for communicating and presenting remotely• How Nancy landed Apple as a client and what she learned—Find the transcript at: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how—Where to find Nancy Duarte:• Twitter: https://twitter.com/nancyduarte• LinkedIn: https://www.linkedin.com/in/nancyduarte/• Website: https://www.duarte.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Nancy’s background(03:25) The insane number of presentations Nancy has helped create(04:52) The most memorable presentation of Nancy’s career, and what it taught her(07:04) The lasting impact of working with Al Gore(09:00) How Nancy landed Apple as a client(11:44) How working with Apple informed future presentations(16:22) 3 things to remember when creating a deck(17:33) The importance of empathy(20:29) Empathy in action(22:40) Why internal presentations are so high-pressure(23:09) Signs you’re doing a good job making the audience the hero of the story(25:38) The structure of great talks(28:08) Lessons from great historical speeches(30:02) You’re presenting more often than you think(32:07) How Nancy uses this story structure in her marriage(35:00) The framework What is? What could be? What is the ideal bliss?(36:07) The importance of visuals(41:12) Slide-making principles (titles, organization, and more)(45:46) The Minto Pyramid Principle(48:02) Think and plan before diving into software(50:00) The Duarte process for crafting presentations(53:18) How remote work has influenced the way we communicate and present (55:46) Strategies for overcoming stage fright and nerves(1:01:10) The concept of “torchbearer leaders” and why it’s important (1:04:54) The surprising truth about informal vs. formal production quality(1:07:37) Examples of PMs telling great stories(1:11:49) Lightning round—Referenced:• Al Gore’s An Inconvenient Truth: https://algore.com/library/an-inconvenient-truth-dvd• Apple’s Think Different campaign: https://www.youtube.com/watch?v=5sMBhDv4sik• The Secret Structure of Great Talks (Nancy’s TED talk): https://www.ted.com/talks/nancy_duarte_the_secret_structure_of_great_talks• The Structure of Great Talks graphic: https://www.google.com/search?q=nancy+duarte+ted+talk+great+story+up+and+down+like+teeth&tbm=isch&sa=X&ved=2ahUKEwi2hoCZmJH_AhVXATQIHb1KC2AQ0pQJegQIBxAB&biw=1512&bih=838&dpr=2#imgrc=5Jei-bDCXe2qQM• I Have a Dream speech by Martin Luther King Jr.: https://www.youtube.com/watch?v=vP4iY1TtS3s• The Minto Pyramid Principle: Logic in Writing, Thinking and Problem Solving: https://www.amazon.com/Minto-Pyramid-Principle-Writing-Thinking• The Minto Pyramid Principle and the SCR Framework, by Lenny: https://www.lennysnewsletter.com/p/minto-pyramid-principle-scr• Illuminate: Ignite Change Through Speeches, Stories, Ceremonies, and Symbols: https://www.amazon.com/Illuminate-Through-Speeches-Stories-Ceremonies• Marshall Ganz: https://www.hks.harvard.edu/faculty/marshall-ganz• Brian Chesky: https://www.linkedin.com/in/brianchesky/• Airbnb’s Snow White storyboards: https://uxdesign.cc/how-airbnb-proved-that-storytelling-is-the-most-important-skill-in-design-15d04ac71039• The Writer’s Journey: https://www.amazon.com/Writers-Journey-Anniversary-Mythic-Structure• Business Proposal: https://asianwiki.com/Business_Proposal• Writer: https://writer.com/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Coda—Meet the evolution of docs | Lenny’s Job Board—Hire the best product people. Find the best product gigs | Eco—Your most rewarding app—Andy Raskin helps CEOs align their leadership teams around a strategic narrative—a single story that powers success in sales, marketing, product, fundraising, and recruiting. His clients include Gong, Dropbox, Uber, Salesforce, Square, and IBM. In today’s episode, we discuss:• What a strategic narrative is, and how to craft one• How having a strategic narrative can bring alignment to your entire company• Examples of strategic narratives in action• Who needs a strategic narrative and who doesn’t• Why Andy thinks about movements instead of categories—Find the transcript at: https://www.lennysnewsletter.com/p/the-power-of-strategic-narrative—Where to find Andy Raskin:• LinkedIn: https://www.linkedin.com/in/andyraskin/• Website: https://www.andyraskin.com/• Podcast: https://andyraskin.com/podcast/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Andy’s background(08:03) What is a strategic narrative?(10:34) How Salesforce would have pitched the old way(12:02) Examples of a strategic narrative in action (15:23) How one piece of writing skyrocketed Andy’s career(16:40) The power of writing online(17:53) Two paths to writing online(19:27) Naming the old game(20:59) Naming the stakes (23:29) Naming the objective(25:17) Naming the obstacles(26:35) Overcoming the obstacles(26:57) How the strategic narrative parallels the hero’s journey (28:25) Telling one story well vs. being a good storyteller(29:18) The 5-step framework summarized(31:33) An example of the 5-step framework in action(36:12) The impact of shifting to the strategic narrative approach (39:08) Companies that are nailing their strategic narrative (40:36) Why Andy thinks about movements instead of categories(44:15) Should every company have a strategic narrative?(46:33) Signs that something is broken in your strategic narrative(48:53) Steps to get started on your own(51:36) How to reach Andy(51:53) Why the second session is the low point in the process(55:30) Why the CEO needs to be part of the process(57:40) Lightning round—Referenced:• Salesforce: https://www.salesforce.com/• Marc Benioff: https://www.linkedin.com/in/marcbenioff/• Zuora: https://www.zuora.com/• The Greatest Sales Deck I’ve Ever Seen: https://medium.com/the-mission/the-greatest-sales-deck-ive-ever-seen-4f4ef3391ba0• Gong: https://www.gong.io/• Tien Tzuo: https://www.linkedin.com/in/tientzuo/• Want a Better Pitch? Master the “Move”: https://medium.com/firm-narrative/want-a-better-pitch-master-the-move-5fbee071ca7f• Star Wars: https://www.starwars.com/• The Hero with a Thousand Faces: https://www.amazon.com/Thousand-Faces-Collected-Joseph-Campbell/dp/1577315936• 360Learning: https://360learning.com/• Nick Hernandez: https://www.linkedin.com/in/nicoconut/• Amit Bendov: https://www.linkedin.com/in/amitbendov/• Drift: https://www.drift.com/• OneTrust: https://www.onetrust.com/• “Shitty First Drafts” by Anne Lamott: https://learning.hccs.edu/faculty/pamela.golden/engl2327/shitty-first-drafts-by-anne-lamott/view• Story: https://www.amazon.com/Story-Substance-Structure-Principles-Screenwriting/• Out of Sheer Rage: https://www.amazon.com/Out-Sheer-Rage-Wrestling-Lawrence/• Station Eleven: https://www.imdb.com/title/tt10574236/• Fitbit: https://www.fitbit.com/global/us/home• Apple Watch: https://www.apple.com/watch—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Microsoft Clarity—See how people actually use your product | Eppo—Run reliable, impactful experiments | Eco—Your most rewarding app—Gustav Söderström is the Co-President and Chief Product and Technology Officer at Spotify. He is responsible for Spotify’s global product and technology strategy, overseeing the product, design, data, and engineering teams. Prior to Spotify, he founded 13th Lab, a startup that was later acquired by Facebook’s Oculus. He also served as the Director of Product and Business Development for Yahoo Mobile and founded Kenet Works, a company focused on community software for mobile phones, which was acquired by Yahoo in 2006. In today’s episode, we discuss:• How Spotify structures product teams to promote freedom of thought• Lessons on thinking long-term and navigating negative feedback• Why Gustav started a podcast and what he’s learned• How AI has impacted the work PMs, engineers, and designers do within Spotify• AI-generated music and its impact on artists• What’s next for Spotify and Spotify Podcasting—Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the—Where to find Gustav Söderström:• Twitter: https://twitter.com/GustavS• LinkedIn: https://www.linkedin.com/in/gustavsoderstrom/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Gustav’s background(04:08) The various roles Gustav has occupied at Spotify(06:54) Why Gustav launched a podcast and what he learned(12:37) How PMs and product teams should think about AI(21:23) AI-generated music(26:19) Will AI continue to be a magic trick for products?(28:27) How Spotify organizes product teams(34:33) How Spotify operationalized autonomy(35:45) Why Spotify uses a centralized model for structuring their organization(43:34) The big bet Spotify took with redesigning its interface, and what they learned(57:26) How they tested their hypothesis before launch(1:02:35) Gustav’s “10% planning time” methodology (1:03:53) How to bring energy and clarity to your work(1:08:07) How to systematize deep thinking(1:10:29) The peeing-in-your-pants analogy (1:11:38) Thoughts on how the Swedish culture is portrayed in Succession (1:13:30) What’s next for Spotify and Spotify Podcasting(1:15:52) Lightning round—Referenced:• Spotify: https://open.spotify.com/• Daniel Ek: https://www.linkedin.com/in/daniel-ek-1b52093a/• Spotify: A Product Story podcast: https://open.spotify.com/show/3L9tzrt0CthF6hNkxYIeSB• Spotify’s AI DJ: https://newsroom.spotify.com/2023-02-22/spotify-debuts-a-new-ai-dj-right-in-your-pocket/• Avicii: https://avicii.com/• DALL-E: https://openai.com/product/dall-e-2• Stable Diffusion: https://stability.ai/• Midjourney: https://www.midjourney.com/• Brian Chesky: https://www.linkedin.com/in/brianchesky/• Succession on HBO: https://www.hbo.com/succession• Fjällräven: https://www.fjallraven.com/us/en-us• 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy• Charlie Munger: The Complete Investor: https://www.amazon.com/Charlie-Munger-Tren-Griffin• The Mystery of the Aleph: Mathematics, the Kabbalah, and the Search for Infinity: https://www.amazon.com/Mystery-Aleph-Mathematics-Kabbalah-Infinity• Something Deeply Hidden: Quantum Worlds and the Emergence of Spacetime: https://www.amazon.com/Something-Deeply-Hidden• Helgoland: Making Sense of the Quantum Revolution: https://www.amazon.com/Helgoland-Making-Sense-Quantum-Revolution• The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/The-Beginning-of-Infinity• The Fabric of Reality: The Science of Parallel Universes—and Its Implications: https://www.amazon.com/The-Fabric-of-Reality• The Case Against Reality: Why Evolution Hid the Truth from Our Eyes: https://www.amazon.com/The-Case-Against-Reality-audiobook/dp/B07VL5TCVF/ref=sr_1_1• Gödel’s Proof: https://www.amazon.com/G%C3%B6dels-Proof-Ernest-Nagel• The Demon in the Machine: How Hidden Webs of Information Are Solving the Mystery of Life: https://www.amazon.com/Demon-Machine-Information-Solving-Mystery• Halt and Catch Fire on Apple TV: https://tv.apple.com/us/show/halt-and-catch-fire/umc.cmc.5s15r46uj0wx044tipm2zoh88• Duolingo: https://www.duolingo.com/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Braintrust—For when you needed talent, yesterday | Eppo—Run reliable, impactful experiments | Rows—The spreadsheet where data comes to life—Scott Belsky is an entrepreneur, author, investor, and currently Adobe’s Chief Strategy Officer and EVP of Design and Emerging Products. He founded Behance, an online platform for creative professionals to showcase and discover work, and served as CEO until its acquisition by Adobe. Scott is an early advisor and investor in several businesses at the intersection of technology and design, including Pinterest, Uber, Warby Parker, Airtable, and Flexport. He is also the author of two nationally bestselling books and founded 99U, a publication and conference focused on productivity in the creative world. In today’s episode, we discuss:* How to strengthen your product sense* Why you should only do half the things you want* What it takes to build a successful consumer product* Why you are probably underinvesting in onboarding* The future of AI and how to prepare for it* Advice for founders and PMs who are feeling stuck* Why resourcefulness will take you further than resources* Adobe’s current priorities and their exciting path ahead—Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-on-building-product-sense—Where to find Scott Belsky:• Twitter: https://twitter.com/scottbelsky• LinkedIn: https://www.linkedin.com/in/scottbelsky/• Blog: https://www.implications.com/• Website: www.scottbelsky.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Scott’s background(04:50) Why Scott shifted roles at Adobe(08:29) Advice for PMs looking to build product sense(10:43) The first mile(13:18) How to develop more empathy(16:33) How to build consumer products that work(20:42) Scott’s philosophy that you should “only do half the things you want to do”(26:15) Scott’s optimism about how the world will look in five years with AI(29:44) How AI will impact product teams(32:55) How the PM role will change as a result of AI(35:09) How Adobe is leveraging AI tools(36:59) What the term “golden gut” means(38:15) Advice for PMs to stay ahead of the new AI trends(41:02) How to start writing more(41:49) The messy middle(47:03) What Scott looks for as an angel investor (50:16) Why resourcefulness will take you further than resources (52:41) Adobe’s current priorities and the path ahead(54:58) Lightning round —Referenced:• Adobe: https://www.adobe.com/• Behance: https://www.behance.net/• Casey Winters on Lenny’s Podcast: https://www.lennyspodcast.com/thinking-beyond-frameworks-casey-winters-pinterest-eventbrite-airbnb-tinder-canva-reddit-grubhub/• Crafting The First Mile Of Product: https://medium.com/positiveslope/crafting-the-first-mile-of-product-7ed25e8f1027• Shishir Mehrotra on Lenny’s Podcast: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/• Scott’s tweet on only doing half the things you want to do: https://twitter.com/scottbelsky/status/1441469886975279109?s=20• Matt Mochary on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/• Adobe Firefly: https://www.adobe.com/sensei/generative-ai/firefly• Howie Liu (CEO at Airtable): https://www.linkedin.com/in/howieliu/• ChatGPT: https://openai.com/blog/chatgpt• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072• Adobe Express: https://www.adobe.com/express• Build: An Unorthodox Guide to Making Things Worth Making by Tony Fadell: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067• Cosmos: A Spacetime Odyssey on Netflix: https://dvd.netflix.com/Movie/Cosmos-A-Spacetime-Odyssey/80004448• Vinod Khosla’s prediction: https://futurism.com/80-of-it-jobs-can-be-replaced-by-automation-and-its-exciting• Queue: https://www.queue.co/• Tome: https://tome.app/• Kevin Kelly on The Tim Ferriss Show: https://tim.blog/2014/08/29/kevin-kelly/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Microsoft Clarity—See how people actually use your product | Eco—Your most rewarding app | LMNT—Zero-sugar hydration—Ayo Omojola is Chief Product Officer at Carbon Health, one of the fastest-growing and most innovative health tech companies in the world. Previously, he was a PM leader at Cash App, where he co-created the Cash Card and scaled it to a nine-figure revenue line for Square. He’s also an angel investor in companies like Mercury, Modern Treasury, Faire, and many others. In this episode, we discuss:• How Cash App broke through the noise and became a consumer app success story• Why small teams are better than big ones• Hard-won lessons on team building and hiring• Why it’s “criminal” not to connect people in your network to things that they need• Why you sometimes shouldn’t listen to experts• The importance of first-principles thinking• Advice for health tech founders—Find the full transcript at: https://www.lennyspodcast.com/frameworks-for-product-differentiation-team-building-and-thinking-from-first-principles-ayo-omojola-carbon-health-cash-app/#transcript—Where to find Ayo Omojola:• Twitter: https://twitter.com/ay_o• LinkedIn: https://www.linkedin.com/in/omojola/• Blog: https://kunle.app/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Ayo’s background(04:13) The story of how Ayo used Quora for discoverability (06:44) The scale of Cash App (07:37) What Cash App did well(10:12) Lessons from building consumer apps (13:08) Why it’s so important to be different(14:08) What Ayo learned from how Square/Block operates(16:36) How to succeed at building a startup within a startup(19:06) How Ayo transitioned from fintech to health tech(22:51) Why Ayo loves hiring founders (28:32) Team-building strategies(32:12) The importance of going deep and challenging assumptions(36:58) Why you should always ask questions(38:45) Lessons in leadership(41:43) Advice for founders in the health-care space(44:48) What Carbon Health is(46:58) Lightning round—Referenced:• Ayo on Quora: https://www.quora.com/profile/Ayo-Omojola• Carbon Health: https://carbonhealth.com/• Cash App: https://cash.app/• Lob: https://www.lob.com/• Mailform: https://www.mailform.io/• Venmo: https://venmo.com/• PayPal: https://www.paypal.com/us/home• Apple Cash: https://www.apple.com/apple-cash/• Square: https://squareup.com/us/en/home/• Block: https://block.xyz/• Pinwheel: https://www.pinwheelapi.com/• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032• Children of Time: https://www.amazon.com/Children-of-Time• Children of Memory: https://www.amazon.com/Children-Memory-Adrian-Tchaikovsky/• Children of Ruin: https://www.amazon.com/Children-Ruin-Time-Adrian-Tchaikovsky/• Stormlight Archive: https://www.amazon.com/Stormlight-Archive-Boxed-Set-Books/• Fire in the Deep: https://www.amazon.com/Fire-Deep-Robert-J-Miller/• War of the Worlds on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.49a287c2-44ed-4ffc-afa0-fab86dd0d31d• Succession on HBO Max: https://play.hbomax.com/player/urn:hbo:episode:GWukCJAu0e4uHwwEAAAB5• No Context Succession on Twitter: https://twitter.com/nocontextroyco—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Braintrust—For when you needed talent, yesterday | AssemblyAI—Production-ready AI models to transcribe and understand speech | Miro—A collaborative visual platform where your best work comes to life—Jonathan Becker is the founder and president of Thrive Digital, where he and his team have deployed more than $3.5 billion in paid acquisition budgets for companies like Uber, Asana, Square, Tempur-Pedic, and MasterClass. He spent the first part of his career mastering SEO and is a world expert in DTC, lead generation, demand generation, and user acquisition. In today’s episode, we discuss:• Signs that your company is a good fit for paid growth• Strategies for optimizing ad creatives• The merits of different marketing channels: paid vs. organic search, TikTok and short-form• Insights on attribution and how to approach it effectively• How market conditions and AI impact paid growth• The crazy story of how Jonathan won Uber as a client—Find the full transcript at: https://www.lennysnewsletter.com/p/mastering-paid-growth-jonathan-becker—Where to find Jonathan Becker:• Twitter: https://twitter.com/jzbecker• LinkedIn: https://www.linkedin.com/in/jonathanbecker123/• Website: https://thrivedigital.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Jonathan’s background(07:25) The crazy story of how Jonathan won Uber as a client(11:56) Interchangeable terms for “paid growth”(12:31) Why you shouldn’t put all your eggs in one basket(16:48) What kind of companies should pursue paid growth(23:07) Is it possible to reach scale exclusively through paid growth?(27:07) The evolution of performance marketing(29:39) Advice for founders choosing between SEO and paid(32:18) Strategies for optimizing ad creatives(44:43) Paid vs. organic search, TikTok and short-form(49:56) Where to spend money in order to drive growth for B2B SaaS(55:06) Attribution in performance marketing (1:04:18) The impact of AI on paid growth(1:12:52) Advice for early-stage startups on hiring in-house vs. hiring an agency (1:17:09) Qualifications to look for in your hires(1:23:23) How Jonathan won Snapchat as a client(1:28:55) Lightning round—Referenced:• Andrew Wilkinson: https://www.linkedin.com/in/awilkinson/• Garrett Camp: https://www.forbes.com/profile/garrett-camp/• TikTok: https://www.tiktok.com/• Grammarly: https://app.grammarly.com/• Athletic Greens: https://athleticgreens.com/en• Supermetrics: https://supermetrics.com/• Recast: https://getrecast.com/• Midjourney: https://www.midjourney.com/• DALL-E: https://openai.com/product/dall-e-2• Storyworthy: https://www.amazon.com/Storyworthy-Engage-Persuade-through-Storytelling/dp/1608685489• Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike-ebook/dp/B0176M1A44• American Kingpin: https://www.amazon.com/American-Kingpin-Criminal-Mastermind-Behind/dp/1591848148• The Big Short: https://www.imdb.com/title/tt1596363/• White Lotus on HBO: https://www.hbo.com/the-white-lotus—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Mixpanel—Product analytics that everyone can trust, use, and afford | Eppo—Run reliable, impactful experiments | Braintrust—For when you needed talent, yesterday—David Singleton is Chief Technology Officer at Stripe, where he oversees engineering and design teams. Since joining Stripe, David has helped grow the technology org across the U.S. and developed new engineering hubs in Singapore and Dublin as well as Stripe’s fifth hub, remote engineering, across the globe. Before Stripe, he spent 11 years at Google, where he was VP of Engineering, leading product development and coordinating more than 15 different hardware partnerships. In today’s episode, we cover:• Hiring secrets that set Stripe employees apart• How to build a product-minded engineering team• How to operationalize meticulousness• Strategies for maintaining developer productivity at scale• The process of “friction logging” used to make better products• How AI is changing the way engineers work• Insights for planning and prioritizing at scale—Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-culture-of-excellence—Where to find David Singleton:• Twitter: https://twitter.com/dps• LinkedIn: https://www.linkedin.com/in/davidpsingleton/• Website: https://blog.singleton.io/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) David’s background(04:22) How Stripe’s unique hiring process has helped them build an incredible team(12:27) An example of a relentlessly curious and passionate employee(14:11) Structured hiring loops at Stripe(16:39) How Stripe built a product-minded engineering culture(21:56) Stripe’s operating principles (25:39) How Stripe uses “friction logging” to build a meticulous product culture (32:22) How to operationalize friction logging(35:02) How to set PMs up for success(36:53) Stripe’s collaborative approach to product evaluation(41:17) Advice for presenting to CTOs (42:58) How to get better at building products(45:28) Stripe’s “engineerications” and the importance of getting into the weeds as a leader(52:03) Auto-testing and other strategies to improve shipping speeds(59:29) Improving developer productivity(1:00:54) How AI has impacted the way Stripe builds product (1:07:03) Why David is excited about Copilot(1:09:24) Lessons from managing people(1:14:30) Planning and prioritization based on first-principles thinking(1:18:23) Lenny’s feedback from using Stripe(1:19:14) What’s next for Stripe(1:22:10) Lightning round—Referenced:• Stripe: https://stripe.com/• Jeff Weinstein: https://www.linkedin.com/in/jeffwweinstein/• How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p• GitHub Copilot: https://github.com/features/copilot• High Output Management by Andrew Grove: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884• Build by Tony Fadell: https://www.amazon.com/Build/dp/1787634116/ref=tmm_pap_swatch_0• Scaling People: Tactics for Management and Company Building by Claire Hughes Johnson: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/• Andrej Karpathy on YouTube: https://www.youtube.com/@AndrejKarpathy• Midjourney: https://www.midjourney.com/home/• Emily Sands: https://www.linkedin.com/in/egsands/• Michelle Bu: https://www.linkedin.com/in/michellebu/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Brought to you by Rows—The spreadsheet where data comes to life | Braintrust—For when you needed talent, yesterday | Coda—Meet the evolution of docs—Carilu Dietrich is a former CMO, most notably the Head of Marketing who took Atlassian public. These days she’s an advisor to CEOs and CMOs of hypergrowth B2B companies and has worked with companies like Miro, Segment, Bill.com, 1Password, Productboard, Sprout Social, Weights & Biases, and more. In today’s episode, we discuss:* Patterns across the most successful hypergrowth companies* How to advance in your career, and how to someday become an executive* How to decide which company to work at* Advice for navigating the job market during tough times* How to find and execute new growth opportunities* Why most CMOs and CPOs get fired, and what we can learn from this—Find the transcript at: https://www.lennysnewsletter.com/p/how-to-achieve-hypergrowth-in-your—Where to find Carilu Dietrich:• LinkedIn: https://www.linkedin.com/in/hypergrowth-advisor/• Newsletter: www.carilu.com• Twitter: https://twitter.com/clu007—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Carilu’s background(04:28) Habits and behaviors that will help you reach an executive role(07:15) Why there is no substitute for working hard(08:15) 5 things you need to do to get to the C-suite(10:39) Choosing the right company for accelerated career growth(12:42) Criteria for assessing a phenomenal company(14:41) Asking better questions and making decisions with energy(16:05) Advice for finding a job during a recession (19:25) The importance of quality products and sustained brand advertising(24:06) Lessons from successful hypergrowth companies(28:14) Is word of mouth a necessary growth lever?(31:31) How to accelerate word-of-mouth marketing(35:28) Atlassian’s product-led growth strategy and delayed sales team hiring(39:54) When to hire your first salesperson (43:04) Common growth levers and roadblocks (47:01) How to build trust between CEOs and CMOs(49:00) Challenges of C-suite roles in startups(52:55) Bundling strategies(57:17) Lightning round—Referenced:• Tomasz Tunguz: https://www.linkedin.com/in/tomasztunguz/• Denise Persson: https://www.linkedin.com/in/denisepersson/• Oracle: https://www.oracle.com/• Atlassian: https://www.atlassian.com/• Classy: https://www.classy.org/• Snowflake: https://www.snowflake.com/en/• Salesforce: https://www.salesforce.com/• Okta’s “Businesses at Work” 2023: https://www.okta.com/businesses-at-work/• Y U No Use Hipchat billboard: https://techcrunch.com/2011/04/22/y-u-no-have-lame-billboard-hipchat/• Productboard: https://www.productboard.com/• Miro: https://miro.com/• Scott Farquhar: https://www.linkedin.com/in/scottfarquhar/• Elena Verna on Lenny’s Podcast: https://www.lennyspodcast.com/the-ultimate-guide-to-product-led-sales-elena-verna/• Tao Te Ching, Stephen Mitchell translation: https://www.amazon.com/Tao-Te-Ching-Laozi/dp/0060812451/ref=asc_df_0060812451/• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/8183227899/ref=tmm_pap_swatch_0• Never Split the Difference: https://www.amazon.com/Never-Split-Difference-audiobook/dp/B01COR1GM2/ref=sr_1_1• Everything Everywhere All At Once on Hulu: https://www.hulu.com/movie/everything-everywhere-all-at-once-fa320000-8cf3-46fc-8c45-df5ec67b71f2• Tara Brach guided meditations: https://www.tarabrach.com/guided-meditations/—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe