Lenny's Podcast: Product | Growth | Career

By: Lenny Rachitsky
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  • Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.

    www.lennysnewsletter.com
    Lenny Rachitsky
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Economics Leadership Management & Leadership
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Episodes
  • Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder)

    Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder)
    Mar 6 2025
    Ivan Zhao is the co-founder and CEO of Notion. Ivan shares the untold story of Notion, from nearly running out of database space during Covid to finding product-market fit after several “lost years,” and the hard-won lessons along the way.—What you’ll learn:1. Why you sometimes need to “hide your vision” behind something people actually want—what Ivan calls “sugar-coating the broccoli”2. How Ivan and his co-founder persevered through multiple product resets and complete code rewrites3. Why Notion prioritized systems over headcount, keeping the team small and focused even at scale4. Why Ivan believes in craft and values as the foundation for product development, balancing technical excellence with aesthetic sensibility5. The surprising story of how Notion nearly collapsed during Covid when their single database almost ran out of space with only weeks to spare6. Community-led growth tactics7. Ivan’s unique journey from a small town in China8. Much more—Brought to you by:• Eppo—Run reliable, impactful experiments• Airtable ProductCentral—Launch to new heights with a unified system for product development• Sinch—Build messaging, email, and calling into your product—Find the transcript at: https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao—Where to find Ivan Zhao:• X: https://x.com/ivanhzhao• LinkedIn: https://www.linkedin.com/in/ivanhzhao/—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) Introduction to Ivan Zhao(04:41) Ivan’s early life and education(07:46) Discovering the vision for Notion(10:49) The lost years of Notion(13:56) Rebuilding and perseverance(17:14) Layoffs and company morale(18:53) Advice for startup founders(25:08) Product-market fit(29:56) Staying lean and efficient(34:27) Creating a unique office culture(37:20) Craft and values: the foundation of Notion’s philosophy(38:44) Navigating tradeoffs in product and business building(41:24) Leadership and personal growth(49:11) Challenges and crises: lessons from Notion’s journey(51:08) Building horizontal software: joys and pains(01:02:40) Philosophy of tools and human potential(01:06:17) Lightning round and final thoughts—Referenced:• Ürümqi: https://en.wikipedia.org/wiki/%C3%9Cr%C3%BCmqi• Notion: https://www.notion.com/• SpongeBob SquarePants: https://en.wikipedia.org/wiki/SpongeBob_SquarePants• Augmenting Human Intellect: https://web.stanford.edu/class/history34q/readings/Engelbart/Engelbart_AugmentIntellect.html• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay• Ted Nelson: https://en.wikipedia.org/wiki/Ted_Nelson• Steve Jobs on Why Computers Are Like a Bicycle for the Mind (1990): https://www.themarginalian.org/2011/12/21/steve-jobs-bicycle-for-the-mind-1990/• Xerox Alto: https://en.wikipedia.org/wiki/Xerox_Alto• React: https://react.dev/• Simon Last on LinkedIn: https://www.linkedin.com/in/simon-last-41404140/• Magna-Tiles: https://www.magnatiles.com/• Design on a deadline: How Notion pulled itself back from the brink of failure: https://www.figma.com/blog/design-on-a-deadline-how-notion-pulled-itself-back-from-the-brink-of-failure/• Bryan Johnson on X: https://x.com/bryan_johnson• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook• Smalltalk: https://en.wikipedia.org/wiki/Smalltalk#:• Lisp: https://en.wikipedia.org/wiki/Lisp_(programming_language)• DeepSeek: https://www.deepseek.com/• Shana Fisher: https://www.crunchbase.com/person/shana-fisher• LAMY 2000 fountain pens: https://www.jetpens.com/LAMY-2000-Fountain-Pens/• Macintosh 128K: https://en.wikipedia.org/wiki/Macintosh_128K• Toshiba rice cooker: https://www.toshiba-lifestyle.com/us/cooking-appliances/rice-cooker• Transistor radio: https://en.wikipedia.org/wiki/Transistor_radio• Jira: https://www.atlassian.com/software/jira• Salesforce: https://www.salesforce.com/• HubSpot: https://www.hubspot.com/• Zendesk: https://www.zendesk.com/• Misattributed McLuhan quote: https://mcluhangalaxy.wordpress.com/2013/04/01/we-shape-our-tools-and-thereafter-our-tools-shape-us/• Phin Barnes on LinkedIn: https://www.linkedin.com/in/phineasbarnes/• Hacker News: https://news.ycombinator.com/• Pablo Picasso quote: https://www.goodreads.com/quotes/629531-good-artists-copy-great-artists-steal#:~• Connections with James Burke on Prime Video: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.484e32c5-60bd-4493-a800-e44fd0940312• The Enneagram Institute: https://www.enneagraminstitute.com/—Recommended book:• The Romance of the Three Kingdoms: https://www.amazon.com/Romance-Three-Kingdoms-Luo-Guanzhong/dp/024133277X—Production and marketing by https://penname.co/. ...
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    1 hr and 12 mins
  • The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)

    The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)
    Mar 2 2025
    Matt Mullenweg is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with over 1,700 employees across 90 countries. In this episode, he discusses some of the most controversial topics surrounding WordPress, Automattic, and the broader open source community.—What you’ll learn:• Matt’s response to public criticism• Why products like Meta’s Llama are “fake open source”• How his team is turning around Tumblr after acquiring it for just $3 million (after Yahoo bought it for $1.1 billion)• Why he mortgaged his home to fund San Francisco’s iconic Bay Lights project• Matt’s philosophy: “Don’t just build a product; build a movement”• Why open source matters: “If the Founding Fathers were around today, they’d be open source advocates”—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta—Automate compliance. Simplify security.• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/the-creator-of-wordpress-opens-up-matt-mullenweg—Where to find Matt Mullenweg:• X: https://x.com/photomatt• LinkedIn: https://www.linkedin.com/in/mattm/• Instagram: https://www.instagram.com/photomatt/• Website: https://ma.tt/—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) Introduction to Matt Mullenweg(05:10) Matt’s career journey(11:15) Bay Lights project and philanthropy(17:28) How Matt got involved with open source(23:25) Why products like Meta’s Llama are “fake open source”(27:14) The future of open source and how to get involved(35:25) Building a successful online community(39:12) The WP Engine controversy(50:24) Facing criticism and controversy(55:29) Addressing community concerns(01:08:29) Forking Advanced Custom Fields(01:11:15) The role of social media and public perception(01:16:43) Acquiring and reviving Tumblr(01:24:25) Automattic’s acquisition strategy(01:28:51) Final thoughts and future plans—Referenced:• WordPress: https://wordpress.com/• Automattic: https://automattic.com/• CNET: https://www.cnet.com/• Akismet: https://akismet.com/wordpress/• Jetpack: https://jetpack.com/• Toni Schneider on LinkedIn: https://www.linkedin.com/in/tonischneider/• WooCommerce: https://woocommerce.com/• Beeper: https://www.beeper.com/• Day One: https://dayoneapp.com/• Simplenote: https://simplenote.com/• Pocket Casts: https://pocketcasts.com/• Creative Commons: https://creativecommons.org/• Audrey Capital: https://audrey.co/• Stripe: https://stripe.com/• SpaceX: https://www.spacex.com/• Calm: https://www.calm.com/• August: https://august.com/• Daylight Computer: https://daylightcomputer.com/• Keys Jazz Bistro: https://keysjazzbistro.com/• Joomla: https://www.joomla.org/• Drupal: https://new.drupal.org/• Shopify: https://www.shopify.com/• Wix: https://www.wix.com/• Squarespace: https://www.squarespace.com/• Tumblr: https://www.tumblr.com/• Gravatar: https://gravatar.com/• The Bay Lights: https://illuminate.org/projects/thebaylights/• The Bay Lights 360: https://illuminate.org/the-bay-lights-360/• Ben Davis on LinkedIn: https://www.linkedin.com/in/ben-davis-sf/• Kinder High School for the Performing and Visual Arts: https://www.houstonisd.org/hspva• Jack Dorsey: We’re Losing our Free Will to Algorithms: https://www.youtube.com/watch?v=9_8NganZSFI• Marc Andreessen: https://a16z.com/author/marc-andreessen/• Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/• An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead): https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet• Llama: https://www.llama.com/• WordCamp US & Ecosystem Thinking: https://ma.tt/2024/09/ecosystem-thinking/• As Wall Street Chases Profits, Fire Departments Have Paid the Price: https://www.nytimes.com/2025/02/17/us/fire-engines-shortage-private-equity.html• WordCamp Asia: https://asia.wordcamp.org/2025/• Justin Baldoni Hit with Defamation Suit as PR Teams Turn on Each Other over Blake Lively’s ‘It Ends with Us’ Smear Campaign Allegations: https://deadline.com/2024/12/justin-baldoni-defamation-lawsuit-publicist-blake-lively-1236241784/• How WordPress Hot Nacho Scandal Shapes WP Engine Dispute: https://www.searchenginejournal.com/how-wordpress-hot-nacho-scandal-shapes-wp-engine-dispute/539069/• Gutenberg: https://wordpress.org/gutenberg/• ClassicPress: https://www.classicpress.net/• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff• ...
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    1 hr and 34 mins
  • An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead)

    An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead)
    Feb 27 2025
    Keith Coleman (VP of product) and Jay Baxter (founding ML engineer), the minds behind Community Notes, reveal how a small, scrappy team inside Twitter/X built the most trusted crowdsourced information system on the internet—one that’s changing the way we understand truth online. What you’ll learn:1. How Community Notes actually works—a deep dive into the groundbreaking algorithm that rewards “bridging agreement” instead of majority rule2. The seemingly crazy yet brilliant way this idea survived multiple CEO changes—from Jack to Parag to Elon3. How this project started with a dumpster fire GIF (literally)—the untold backstory of its early launch4. The secret to running ultra-fast, high-impact product teams—no OKRs, no Jira; just one Google Doc5. What Meta’s adoption of Community Notes means for the future of online (mis)information—why this open source system is becoming the industry standard—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Productboard—Make products that matter• Wix Studio—The web creation platform built for agencies—Find the transcript at: https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet—Where to find Keith Coleman:• X: https://x.com/kcoleman• LinkedIn: https://www.linkedin.com/in/keith-coleman-19b12b46/—Where to find Jay Baxter:• X: https://x.com/_jaybaxter_• LinkedIn: https://www.linkedin.com/in/jaybaxter/• Website: http://jaybaxter.net/—In this episode, we cover:(00:00) Introduction to Community Notes(06:56) How the “bridging-based” algorithm works(13:33) The impact and scale of Community Notes(17:24) Understanding the note publishing threshold(21:32) Challenges and philosophies(26:26) The effect of notes on re-sharing content(29:41) Origin story(35:46) Embracing small teams for big impact(40:23) The thermal project approach(47:47) Algorithm development and internal competitions(50:34) An inside look at how the team operates(58:56) Working with Elon(01:05:30) Launching Birdwatch(01:10:48) The core principles behind Community Notes(01:26:15) Anonymity and pseudonymity in contributions(01:32:17) Sustaining the project through leadership changes(01:37:57) Future directions for Community Notes(01:42:12) Final thoughts and optimism for the future—Referenced:• Community Notes on X: https://x.com/CommunityNotes• Sign up to be a Community Notes contributor: https://communitynotes.x.com/guide/en/contributing/signing-up• The Making of Community Notes: https://asteriskmag.com/issues/08/the-making-of-community-notes• “Readers added a Community Note to this Tweet”: https://x.com/HelpfulNotes/status/1718103364792205704• Note-ranking algorithm: https://communitynotes.x.com/guide/en/under-the-hood/ranking-notes#matrix-factorization• Study: Community Notes on X could be key to curbing misinformation: https://giesbusiness.illinois.edu/news/2024/11/18/study--community-notes-on-x-could-be-key-to-curbing-misinformation• Study Finds X’s (Formerly Twitter’s) Community Notes Provide Accurate, Credible Answers to Vaccine Misinformation: https://qi.ucsd.edu/study-finds-xs-formerly-twitters-community-notes-provide-accurate-credible-answers-to-vaccine-misinformation/• Did the Roll-Out of Community Notes Reduce Engagement with Misinformation on X/Twitter?: https://dl.acm.org/doi/10.1145/3686967• Kayvon Beykpour on LinkedIn: https://www.linkedin.com/in/kayvz/• Jack Dorsey on X: https://x.com/jack• “Birdwatch gives me the creeps” tweet: https://x.com/elonmusk/status/1589454464611540992• Blake Scholl on LinkedIn: https://www.linkedin.com/in/blakescholl/• Creating Truthtelling Incentives with the Bayesian Truth Serum: https://www.eecs.harvard.edu/cs286r/courses/fall12/papers/DW08.pdf• Asana: https://asana.com/• Spaces: https://blog.x.com/en_us/topics/product/2021/spaces-is-here• Amazon MTurk: https://www.mturk.com/• Community notes on GitHub: https://github.com/twitter/communitynotes• What do I think about Community Notes?: https://vitalik.eth.limo/general/2023/08/16/communitynotes.html• X’s community-led approach: tackling inaccurate and misleading information: https://blog.x.com/en_us/topics/company/2023/xs-community-led-approach-tackling-inaccurate-and-misleading-information• Linda Yaccarino on LinkedIn: https://www.linkedin.com/in/lindayaccarino/• Messi-Ronaldo rivalry: https://en.wikipedia.org/wiki/Messi%E2%80%93Ronaldo_rivalry• Supernotes paper: https://arxiv.org/pdf/2411.06116v1—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
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    1 hr and 48 mins

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