Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss: • How Nubank builds a fanatical user base • Tactics for driving word-of-mouth growth • Measuring customer love through the Sean Ellis score • The importance of strategic clarity • The role of category design in creating successful products • Why companies should strive to be “fundamentally different,” not “incrementally better” • Nubank’s vision for an AI-powered banking future — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Mercury—The powerful and intuitive way for ambitious companies to bank • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal — Where to find Jag Duggal: • LinkedIn: https://www.linkedin.com/in/jagduggal/ — 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) Jag’s background (04:34) Nubank’s remarkable achievements (06:01) Nubank’s product development process (11:23) Nubank’s values (12:16) Building products people love fanatically (15:21) The Sean Ellis score (21:27) An example project using the Sean Ellis score (25:07) Picking up the phone and calling customers (28:20) The importance of starting small and iterating (30:42) Pushing back effectively (34:10) Uncovering pain points through customer research (37:53) An example of setting a clear hypothesis (42:01) Developing a strategy (52:16) “Be fundamentally different, not incrementally better” (53:10) Category design (57:37) Nubank’s founding story and goals for the future (01:00:46) Advice for adding new product lines (01:03:46) The future of fintech and banking (01:09:23) AI corner (01:12:34) Failure corner (01:20:24) Key takeaways (01:22:11) Lightning round — Referenced: • Nubank: https://nubank.com.br/en/ • Coinbase: https://www.coinbase.com/ • Robinhood: https://www.robinhood.com/ • SoFi: https://www.sofi.com/ • Affirm: https://www.affirm.com/ • Lemonade: https://www.lemfi.com/ • Bank of America: https://www.bankofamerica.com/ • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875 • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible • Sequoia Capital: https://www.sequoiacap.com/ • Churrascaria: https://en.wikipedia.org/wiki/Churrascaria • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/ • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/ • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket • Reid Hoffman o
Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss: • The most common traits among successful product managers • The 3 W’s framework for PM career growth • The Four A’s of leveling up in product management • The right way to push back as a PM • Common pitfalls that stall PM careers • Vikrama’s advice for transitioning into product management • Why intent alone is not enough — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Webflow—The web experience platform • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development — Where to find Vikrama Dhiman: • X: https://twitter.com/vikramadhiman • LinkedIn: https://www.linkedin.com/in/vikrama/ • Website: https://www.vikramadhiman.com/ — 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) Vikrama’s background (03:56) Three common traits among great PMs (07:09) The first W: What you produce (15:40) The second W: What you bring to the table (18:58) The third W: What’s your operating model? (20:36) Three traits that make you a great PM to work with (21:49) How to improve the quality and quantity of your outputs (23:26) The art of the pushback (26:55) Common factors that impede career growth (33:39) Vikrama’s personal reflections (39:33) Choosing which skill(s) to focus on developing (46:28) The ambiguity of the PM role (51:47) The 8 axis for PM growth (56:57) Contrarian corner: Why intent alone is not enough (59:30) Lightning round — Referenced: • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock • Gojek: https://www.gojek.com/en-id • SQL: https://en.wikipedia.org/wiki/SQL • Oracle: https://www.oracle.com/ • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/ • Workday: https://www.workday.com/ • Salesforce: https://www.salesforce.com/ • Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681 • Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555 • Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK • Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F • DramaBox: https://www.dramaboxapp.com/ • Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/ • Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF • 9 Best Hawker Centers in Singapore—and What to Eat There: https://ww
Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss: • Potential sources of power that startups should develop from an early stage • Common misconceptions among companies about the types of power they possess • How power relates to strategy • The difference between a moat and a power • Practical strategies for non-leaders to leverage insights about power and strategy in their work • AI’s impact on competitive advantages and barriers to entry — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer — Where to find Hamilton Helmer: • X: https://twitter.com/hamiltonhelmer • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/ • Website: https://7powers.com/ — 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) Hamilton’s background (04:08) When power becomes important (08:24) How strategy relates to power (12:09) How power informs strategy (14:46) The sequence of powers (21:13) Common misconceptions (24:39) Network effects vs. network economies (26:58) Uber’s success (29:16) Moats vs. powers (31:12) Strategies for non-leaders to leverage power and strategy (37:51) Advice on how to become a strategic thinker (39:27) AI’s impact on the seven powers (45:43) Why moving fast is not a power (50:24) Three things that create value in a company (51:16) The debt trajectory of the U.S. (56:35) Optimism for the future (59:25) Lightning round — Referenced: • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/ • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/ • Strategy Capital: https://strategycapital.com/ • Warren Buffett: https://www.forbes.com/profile/warren-buffett/ • Charlie Munger: https://www.forbes.com/profile/charles-munger/ • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6 • Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973 • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars
Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover: • What Annie learned from the late Daniel Kahneman • The power of pre-mortems and “kill criteria” • The relationship between money and happiness • The power of “mental time travel” • The nominal group technique for better decision quality • How First Round Capital improved their decision-making process • Many tactical decision-making frameworks — Brought to you by: • Vanta—Automate compliance. Simplify security. • UserTesting—Human understanding. Human experiences. • LinkedIn Ads—Reach professionals and drive results for your business — Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke — Where to find Annie Duke: • X: https://twitter.com/AnnieDuke • LinkedIn: https://www.linkedin.com/in/annie-duke/ • Website: https://www.annieduke.com/ • Substack: https://www.annieduke.com/substack/ — 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) Annie’s background (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness (09:15) The importance of unconditional love in parenting (15:15) Mental time travel and “nevertheless” (20:06) The extent of improvement possible in decision-making (24:54) Independent brainstorming for better decisions (35:36) Making sure people feel heard (42:41) The “3Ds” framework to make better decisions (44:49) Decision quality (55:46) Improving decision-making at First Round Capital (01:05:05) Using pre-mortems and kill criteria (01:10:15) Making explicit what’s implicit (01:10:55) The challenges of quitting and knowing when to walk away (01:19:23) Where to find Annie — Referenced: • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research# • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/ • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut • Cass Sunstein on X: https://twitter.com/CassSunstein • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market • First Round Capital: https://firstround.com/ • Brett Berson on X: https://twitter.com/brettberson • Renegade Partners: https://www.renegadepartners.com/ • Renata Quintini on X: https://twitter.com/rquintini • Roseanne Wincek on X: https://twitter.com/imthemusic • Josh Kopelman on X: https://twitter.com/joshk • Bill Trenchard on X: https://twitter.com/btrenchard • Linnea Gandhi on X: https://twitter.com/linneagandhi • Maurice Schweitzer on X: https://twitter.com/me_schweitzer • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/ • Quit: The
more | Kayvon Beykpour Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss: • The story of being let go from Twitter after Elon’s acquisition • How he turned Twitter’s stagnant culture around • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done • Why Periscope failed • Advice for building consumer products • When to copy, when to innovate — Brought to you by: • Enterpret—Transform customer feedback into product growth • OneSchema—Import CSV data 10x faster • Heap—Cross-platform product analytics that convert, engage, and retain customers — Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour — Where to find Kayvon Beykpour: • X: https://twitter.com/kayvz • LinkedIn: https://www.linkedin.com/in/kayvz/ — 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) Kayvon’s background (04:31) Getting Elon up to speed at Twitter (11:34) The story of being let go from Twitter after Elon’s acquisition (21:09) Changing the product culture at Twitter (29:44) Building the “hide replies” feature (32:02) Sacred crows, taking bold bets, and reigniting growth (34:28) Aquihires and their impact (42:40) Tips for successful acquisitions and staffing (47:00) The limitations of frameworks like JTBD (53:20) Signs you’ve gone too far with a framework (57:44) Lessons from building Periscope (01:00:41) Reasons why Periscope failed (01:07:24) The challenges of implementing video at Twitter (01:12:05) Copying ideas in good taste (01:17:58) How to get better at building consumer products (01:19:51) What Kayvon is building (01:20:31) Lightning round — Referenced: • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3 • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/ • Elon Musk on X: https://twitter.com/elonmusk • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/ • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/ • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc. • Keith Coleman on X: https://twitter.com/kcoleman • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/ • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/ • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/ • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/ • Chris Sacca’s website: https://chrissacca.com/ • Facebook Live: https://www.facebook.com/formedia
Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss: • The benefits of building robust relationships, in life and work • The 15% rule, and how it will help you build better relationships • The power of vulnerability • Examples of how to practice vulnerability • Why mental models you build early in life hold you back later • The “three realities” and “the net” • The art of inquiry • Practical tips for avoiding defensiveness when getting feedback • The impact of long Covid on Carole’s life — Brought to you by: • Eppo—Run reliable, impactful experiments • CommandBar—AI-powered user assistance for modern products and impatient users • The a16z Podcast—Featuring conversations with the founders and technologists shaping our future — Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin — Where to find Carole Robin: • LinkedIn: https://www.linkedin.com/in/carole-robin/ • Email: carolerobinllc@gmail.com — 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) Carole’s background (05:17) The importance of building robust relationships (10:20) The “Touchy Feely” course at Stanford (13:29) An example of the in-class experience (17:19) Leaders in Tech: developing interpersonal competence (21:36) Progressive disclosure and the 15% rule (24:28) Appropriate disclosure (26:52) The power of vulnerability (34:57) Admitting mistakes and sharing feelings (37:08) Understanding mental models (42:57) The “three realities” framework (53:52) The power of feedback and personal change (58:47) The art of inquiry (01:03:27) How to get better at giving feedback (01:07:47) Exercises and continued learning (01:10:49) “Advice hinders relationships” (01:16:49) Failure corner: AFOG (01:20:30) Takeaways (01:21:51) Lessons from long Covid — Referenced: • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships • Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ • Leaders in Tech: https://leadersintech.org/ • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows • Steve Jobs: https://www.forbes.com/profile/steve-jobs/ • Sheryl Sandberg on X: https://twitter.com/sherylsandberg • Ursula Burns: https://www.forbes.com/profile/ursula-burns/ • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/ • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/ • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://pen-name.notion.site/Carole-Ro
Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss: • How to effectively take ideas from 0 to 1 at larger companies • How to craft a compelling vision • The importance of vulnerability and feedback • The role of intuition and product sense in making decisions • How to practically communicate your vision • How to balance collaboration and strong opinions • Advice for building a strong team culture • Pivoting with grace and enthusiasm • The current AI revolution and its impact on PM — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Lenny’s Talent Team—Hire the best product people. Find the best product gigs • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor — Where to find Mihika Kapoor: • X: https://twitter.com/mihikapoor • LinkedIn: https://www.linkedin.com/in/mihikakapoor/ — 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) Mihika’s background (04:29) Core attributes of great product managers (07:34) Crafting a compelling vision (12:12) The vision behind FigJam (18:25) Delivering a vision without design or engineering skills (21:52) Creating momentum (26:36) The importance of strong conviction (27:45) Direct communication (32:48) Building hype (42:20) Immersing yourself in user insights (47:16) Operationalizing user insights (50:33) Caring deeply about what you build (54:01) Finding passion in your work (57:00) Building a strong culture (01:07:07) Pivoting with grace and enthusiasm (01:11:48) Design Nation (01:13:15) Mihika’s weaknesses (01:16:07) Building new products at larger companies (01:20:50) Coming up with a great idea (01:22:49) The key to going from 0 to 1 (01:26:47) Spreading the idea across the company (01:29:15) Closing thoughts (01:32:11) Lightning round — Referenced: • Figma: https://www.figma.com/ • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/ • The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949 • FigJam: https://www.figma.com/figjam/ • Cognition: https://www.cognition-labs.com/ • Devin: https://www.cognition-labs.com/introducing-devin • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/ • Replit: https://replit.com/ • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/ • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/ • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625 • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/ • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/ • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/ • Config: https://config.figma.com/ • Dev Mode: https://www.figma.com/dev-mode/ • Asana: https://asana.com/ • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/ • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-fr
Director) Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss: • Why founders need to adopt the mindset “Just don’t die” • The most common reason startups fail • When to pivot, and characteristics of a good pivot • The concept of “tar pit ideas” and examples of bad startup ideas • Why investors say no to startups • The importance of market size in investment decisions • The pitfalls of founders over-delegating • Effective ways to talk to customers • 20 ideas Dalton is looking to fund — Brought to you by: • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups — Where to find Dalton Caldwell: • X: https://twitter.com/daltonc • LinkedIn: https://www.linkedin.com/in/daltoncaldwell/ — 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) Dalton’s background (04:41) The value of simple advice (07:04) Dalton’s advice: “Just don’t die” (08:39) Knowing when to stop (11:45) Deciding to pivot (14:26) Characteristics of a good pivot (17:53) Knowing when to pivot (19:03) Zip’s journey and finding a market (21:22) Why Dalton says to “Move towards the mountains and the desert” (23:45) Tar pit ideas (26:49) Understanding why investors say no (29:14) The importance of market size (32:16) Avoiding over-delegation and hiring senior people too early (36:43) Why startups fail (40:30) Effectively talking to customers (45:17) Examples of startups hustling to talk to customers (48:01) Patterns of successful startups (52:05) YC’s Request for Startups (55:37) Early days of Silicon Valley (01:05:33) Contrarian corner: growth hacking for early startups (01:09:28) Failure corner (01:11:15) Closing thoughts (01:12:22) Lightning round — Referenced: • Y Combinator: https://www.ycombinator.com/ • Tiger Woods’s website: https://tigerwoods.com/ • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17 • Brex: https://www.brex.com/ • Retool: https://retool.com/ • Segment: https://segment.com/ • Mixpanel: https://mixpanel.com/ • Whatnot: https://www.whatnot.com/ • Andreessen Horowitz: https://a16z.com/ • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/ • Zip: https://ziphq.com/ • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/ • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/ • Foursquare: https://foursquare.com/ • Razorpay: https://razorpay.com/ • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/ • Lenny Bogdonoff on LinkedIn: https://ww
David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss: • How GitLab operationalizes transparency • The philosophy behind recording and sharing team meetings on YouTube • Their extensive public employee handbook • GitLab’s core value of having “short toes” • Challenges and advice for doing remote work well • Strategies for ensuring effective communication in a remote work environment • GitLab’s breadth-over-depth strategy • The company’s unique approach to AI • The value of using humor in high-stakes conversations — Brought to you by: • Orb—The flexible billing engine for modern pricing • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way — Where to find David DeSanto: • X: https://twitter.com/david_desanto • LinkedIn: https://www.linkedin.com/in/ddesanto/ • Threads: https://www.threads.net/@david.the.beard — 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) David’s background (04:20) Maintaining an epic beard (05:29) Why GitLab publicly shares team meetings (09:49) The GitLab Handbook (11:30) GitLab’s issue tracker (14:29) How to successfully build a culture of transparency (18:11) Benefits of operating with transparency (19:55) The value of building in public (21:53) How GitLab implements their core value of kindness (25:16) What it means to have “short toes” (27:41) Other core values (32:16) Common reasons for not fitting in at GitLab (34:42) Advice for remote teams (42:04) Advice for getting into product (43:52) Advice for PMs who are struggling in a remote world (48:25) Specific tools that help with remote work (53:13) Time zones and remote work (57:18) Breadth-over-depth strategy (01:04:14) AI at GitLab (01:13:11) GitLab’s products and solutions (01:14:54) Lightning round — Referenced: • GitLab: https://about.gitlab.com/ • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4 • The GitLab Handbook: https://handbook.gitlab.com/ • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/ • Y Combinator: https://www.ycombinator.com/ • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/ • Salesforce: https://www.salesforce.com/ • GitLab values: https://handbook.gitlab.com/handbook/values • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure • GitLab direction: https://about.gitlab.com/direction/ • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7 • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • HubSpot: https://www.hubspot.com/ • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-mar
Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss: • Why product-market fit (PMF) matters • First Round Capital’s four-part PMF framework • Level one: Nascent product-market fit • Level two: Developing product-market fit • Level three: Strong product-market fit • Level four: Extreme product-market fit • Examples of companies at each level • How to know if you’re stuck at a level, and how to get unstuck • What to change if you’re stuck: persona, problem, promise, and product • The goals and challenges at each stage — Brought to you by: • WorkOS—The modern API for auth and user identity • Eppo—Run reliable, impactful experiments • CommandBar—AI-powered user assistance for modern products and impatient users — Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market — Where to find Todd Jackson: • X: https://twitter.com/tjack • LinkedIn: https://www.linkedin.com/in/toddj0/ — 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) Todd’s background (06:07) First Round Capital’s PMF framework (09:07) Why product-market fit is so important (11:02) Who can benefit from this framework (12:55) The product-market fit method (16:54) Broad overview of the framework (21:35) Level one: nascent product-market fit (33:16) The four P’s (39:13) Level two: developing product-market fit (49:13) Signs you’re stuck at level two, and what to do (55:12) Level three: strong product-market fit (01:00:17) Signs you’re stuck at level three, and what to do (01:02:22) Level four: extreme product-market fit (01:06:55) Rough timelines for each level (01:11:18) A quick recap of the framework (01:12:15) Diving deeper on the four P’s: what to do if you’re stuck (01:13:56) Dollar-driven discovery (01:25:11) Apply for the product-market-fit method program — Referenced: • First Round: https://firstround.com/ • Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup • Dropbox: https://www.dropbox.com/ • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/ • How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ • How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit • Product-market fit method: http://pmf.firstround.com/ • Stripe: https://stripe.com/ • Plaid: https://plaid.com/ • Paths to PMF: https://review.firstround.com/series/product-market-fit/ • WeWork: https://www.wework.com/ • Casper: https://casper.com/ • Vanta: https://www.vanta.com/ • Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/ • Ramp: https://ramp.com/ • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geof
Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss: • Knowing what you want in your career and being clear about it • Finding your zone of genius and how to operate within it • How to maintain a fast pace in larger companies • How to make it easy for your boss to help you achieve your goals • Advice for navigating the tech industry as a woman • The role of a CPTO and the benefits it brings to organizations • Why she built ChatPRD • Tips for building your own AI tools • The impact of AI on product management and what skills will continue to be important — Brought to you by: • Orb—The flexible billing engine for modern pricing • Dovetail—Bring your customer into every decision • Vanta—Automate compliance. Simplify security — Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor — Where to find Claire Vo: • X: https://twitter.com/clairevo • LinkedIn: https://www.linkedin.com/in/clairevo/ • TikTok: https://www.tiktok.com/@chiefproductofficer — 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) Claire’s background (04:50) How to achieve career progression (10:11) Avoiding promotion obsession (13:50) How Claire stepped into leadership roles (17:24) Operating in your zone of genius (23:03) How to maintain a fast pace (27:46) Setting a high bar for quality and talent (29:54) Normalizing feedback (33:09) Being a woman in tech (47:09) The role of a CPTO (54:19) Building ChatPRD (59:39) Tips for building a GPT (01:02:27) The impact of AI on product management (01:08:08) How AI is changing the product management role (01:14:36) Efficiency gains with ChatPRD (01:16:39) Contrarian corner: sales-led product organizations (01:20:11) Lightning round — Referenced: • LaunchDarkly: https://launchdarkly.com/ • Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw • Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/ • Optimizely: https://www.optimizely.com/ • GitLab: https://about.gitlab.com/ • ChatPRD: https://www.chatprd.ai/ • You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at • SpaceX’s Starship: https://www.spacex.com/vehicles/starship/ • GitHub Copilot: https://github.com/features/copilot • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/ • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Stripe Press: https://press.stripe.com/ • Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327 • Poor Things: https://www.imdb.com/title/tt14230458/ • Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3 • Silicon Valley on HBO: https://www.hbo.com
Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss: • The biggest lessons he has learned from building HubSpot • The importance of leaning into your strengths • Dharmesh’s data-oriented approach to public speaking • How he developed HubSpot’s culture code • The decision-making process at HubSpot • His contrarian approach to building products • Why founders and product teams are all fighting the second law of thermodynamics • How “flash tags” can save your teams time • How to decide what ideas are worth investing in — Brought to you by: • Explo—Embed customer-facing analytics in your product • Vanta—Automate compliance. Simplify security • LinkedIn Ads—Reach professionals and drive results for your business — Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building — Where to find Dharmesh Shah: • X: https://twitter.com/dharmesh • LinkedIn: https://www.linkedin.com/in/dharmesh/ • Website: https://dharmesh.com/ — 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) Dharmesh’s background (04:20) Fun facts about Dharmesh (06:31) His data-oriented approach to public speaking (11:45) Advice for adding humor to your presentations (15:28) Why he has no direct reports (18:46) You can shape the universe to your liking (20:02) Lessons from building HubSpot (23:43) Contrarian ways of running a company (37:26) Fighting the second law of thermodynamics (40:29) The importance of simplicity in running a business (45:22) Succeeding in the SMB market (50:29) Zigging when others are zagging (54:17) When it makes sense to go “wide and deep” (57:33) Using flashtags to communicate opinions (01:02:44) HubSpot’s decision-making process (01:09:41) Deciding what ideas to invest in (01:15:26) Defining and maintaining company culture (01:30:46) The potential of AI (01:37:03) Practical advice for learning AI (01:40:07) Where to find Dharmesh — Referenced: • WordPlay: https://wordplay.com/article/unlimited • ChatSpot: https://chatspot.ai/ • Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26 • Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/ • The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/ • SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/ • Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/ • First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles • Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/ • The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics • What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business • Shopify: https://www.shopify.com/ • Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.l
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