A weekly advice column about building product, driving growth, and accelerating your career.
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
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Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer
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Where to find Hamilton Helmer:
• X: https://twitter.com/hamiltonhelmer
• LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/
• Website: https://7powers.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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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-to-blockbuster.html
• Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/
• What Is Strategy?: https://hbr.org/1996/11/what-is-strategy
• TSMC: https://www.tsmc.com/english
• Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System
• America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/
• Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke
• Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes
• Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter
• Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982
• The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311
• The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X
• American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX
• Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/
• Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland
• Ogilvy: https://www.ogilvy.com/
• Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005
• Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill
• Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498
• The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo)
• Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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
—
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Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke
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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/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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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 Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/
• Richard Thaler on X: https://twitter.com/R_Thaler
• Stewart Butterfield on X: https://twitter.com/stewart
• Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)
• How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66
• The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/
• The Alliance for Decision Education: https://alliancefordecisioneducation.org/
• Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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
—
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Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour
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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
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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/tools/facebook-live
• Kevin Hart on X: https://twitter.com/KevinHart4real
• Clubhouse: https://www.clubhouse.com/
• Vine: https://en.wikipedia.org/wiki/Vine_(service)
• Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/
• Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/
• Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624
• Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW
• The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM
• Star Trek official site: https://www.startrek.com/
• Dune: part 2: https://www.dunemovie.com/
• Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer
• Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942
• Devs on Hulu: https://www.fxnetworks.com/shows/devs
• Nick Offerman on X: https://twitter.com/nick_offerman
• 3 Body Problem on Netflix: https://www.netflix.com/title/81024821
• Perplexity AI: https://www.perplexity.ai/
• Particle: https://www.particle.news/
• Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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
—
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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: [email protected]
—
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
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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://www.notion.so/pen-name/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb
• Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322
• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey
• Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2
• Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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:
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• 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-free
• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/
• Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/
• Design Disruptors: https://www.invisionapp.com/films/design-disruptors
• Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/
• Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/
• Design Nation: https://dn.businesstoday.org/
• Stuart Weitzman on X: https://twitter.com/StuartWeitzman
• Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/
• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/
• Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot
• Hestia: https://en.wikipedia.org/wiki/Hestia
• Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076
• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/
• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649
• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7
• Dune: Part 2: https://www.dunemovie.com/
• Arc browser: https://arc.net/
• Pika: https://pika.art/home
• The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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
—
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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://www.linkedin.com/in/rememberlenny/
• Milk Video: https://milkvideo.com/
• Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/
• How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups
• Collison installation: https://news.ycombinator.com/item?id=18400504
• Stripe: https://stripe.com/
• Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/
• John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/
• Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/
• Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/
• Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/
• 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/
• YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups
• ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software
• Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies
• New space companies: https://www.ycombinator.com/rfs#new-space-companies
• A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer
• Spatial computing: https://www.ycombinator.com/rfs#spatial-computing
• New defense technology: https://www.ycombinator.com/rfs#new-defense-technology
• Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america
• Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue
• Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones
• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/
• Sam Altman on X: https://twitter.com/sama
• Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/
• Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/
• Marc Andreessen on X: https://twitter.com/pmarca
• Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/
• Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0
• Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757
• Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1
• Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/
• The Sopranos on HBO: https://www.hbo.com/the-sopranos
• The Wire on HBO: https://www.hbo.com/the-wire
• Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA
• Oura ring: https://ouraring.com/
• Apple watch: https://www.apple.com/watch/
• SiPhox: https://siphoxhealth.com/
• Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC
• How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0
• The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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:
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• 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-market/
• Open-core model: https://en.wikipedia.org/wiki/Open-core_model
• GitLab Duo: https://about.gitlab.com/gitlab-duo/
• GitLab Docs: https://docs.gitlab.com/
• Anthropic: https://www.anthropic.com/
• GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/
• Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382
• The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/
• The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3
• Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416
• Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B
• The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/
• Artifact News: https://artifact.news/
• Superhuman: https://superhuman.com/
• Arc browser: https://arc.net/
• An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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:
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• 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 | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/
• Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/
• Lattice: https://lattice.com/
• Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/
• Positioning: https://www.lennysnewsletter.com/p/positioning
• Retool: https://retool.com/
• David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/
• Persona: https://withpersona.com/
• Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/
• Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/
• Looker: https://en.wikipedia.org/wiki/Looker_(company)
• Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/
• Ironclad: https://ironcladapp.com/
• Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ
• Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/
• Verkada: https://www.verkada.com/
• Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/
• Databricks: https://www.databricks.com/
• Stripe Radar: https://stripe.com/radar
• Stripe Atlas: https://stripe.com/atlas
• Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader
• Cash App: https://cash.app/
• Square Checking: https://squareup.com/us/en/campaign/banking/checking
• Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital
• Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/
• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/
• Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/
• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/
• Simon Kucher: https://www.simon-kucher.com/
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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/silicon-valley
• Chrysler Pacifica: https://www.chrysler.com/pacifica.html
• Waymo: https://waymo.com/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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
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• LinkedIn Ads—Reach professionals and drive results for your business
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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
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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/
• 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.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/
• FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion
• What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021
• A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite
• Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/
• Zip: https://ziphq.com/
• The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx
• How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie
• What is SQL?: https://aws.amazon.com/what-is/sql/
• GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss:
• The concept of “daring to be dull”
• The power of visualization to desensitize oneself to speaking situations
• Managing negative self-talk
• The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks)
• The ADD structure for Q&As (answer, detailed example, describe relevance)
• Breathing techniques to reduce anxiety, such as the double exhale
• Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications)
• Much more
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Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and
—
Where to find Matt Abrahams:
• X: https://twitter.com/tftsthepod
• LinkedIn: https://www.linkedin.com/in/maabrahams/
• Website: https://mattabrahams.com/
• Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo
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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) Matt’s background
(04:50) Techniques for managing anxiety in public speaking
(10:57) Dare to be dull
(13:40) Reframing anxiety as excitement
(16:08) Using mantras to boost confidence
(18:45) Managing negative self-talk
(20:03) Normalizing speaking anxiety
(23:12) Using conversation as a communication technique
(24:52) Using the double-exhale breathing technique
(28:29) Getting present-oriented
(29:46) Using tongue twisters
(33:34) Broad advice for speaking on the spot
(38:35) The PREP structure
(38:59) The What? So What? Now What? structure
(42:10) Toastmasters and improv
(45:31) Getting better at small talk
(51:05) The importance of sharing back
(52:33) Giving feedback
(56:31) Improving toasts and tributes
(01:02:57) Mastering Q&A sessions
(01:07:25) Apologizing effectively
(01:09:29) Closing thoughts
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
—
Lenny may be an investor in the companies discussed.
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