Lenny's Podcast: Product | Growth | Career

• 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)

  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• Mary Hubbard on LinkedIn: https://www.linkedin.com/in/maryfhubbard/• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Founder mode: https://paulgraham.com/foundermode.html• Cow.com: https://www.cow.com/• David Karp on X: https://x.com/davidkarp• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/• Alibaba: https://www.alibaba.com/• WP Engine Tracker: https://wordpressenginetracker.com/• Kumbh Mela: https://en.wikipedia.org/wiki/Kumbh_Mela—Recommended book:• Maintenance: Of Everything (in progress): https://books.worksinprogress.co/book/maintenance-of-everything/addenda/page/introduction—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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• An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead)

  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 [email protected].—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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• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)

  Bob Moesta, co-creator of the Jobs to Be Done framework, recently published a new book, Job Moves. Drawing from interviews with over 1,000 people about their career transitions, it offers a practical playbook for career development. In our conversation, we discuss:• The four different “quests” that drive career changes• Why job features (salary, title) matter less than experiences• How to identify what gives you energy vs. drains you• The power of taking a “jobcation”• A template for crafting your career story• Tips for hiring and retaining great talent• The importance of prototyping potential careers• Much more—Brought to you by:• Eppo—Run reliable, impactful experiments• Vanta—Automate compliance. Simplify security• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta—Where to find Bob Moesta:• X: https://x.com/bmoesta• LinkedIn: https://www.linkedin.com/in/bobmoesta/• Website: https://www.jobmoves.com/• Podcast: https://pca.st/gg6goo1n• The Re-Wired Group: https://therewiredgroup.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) Bob's background(05:10) Bob’s new book, Job Moves(09:31) Job features vs. job experiences(11:16) Four reasons people leave jobs(17:20) Energy drivers and energy drains(31:05) Prototyping your next job(34:32) Pushes and pulls(40:01) Understanding that no job is perfect(43:18) Taking a jobcation(51:22) Finding the right next step(55:18) Navigating job applications and interviews(58:28) How to craft your career story(01:04:04) Strengths and weaknesses: leveraging your superpowers(01:06:21) Hiring and writing job descriptions(01:11:20) Self-awareness and founding a startup(01:21:24) Conclusion and final thoughts—Referenced:• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta• Ethan S. Bernstein on LinkedIn: https://www.linkedin.com/in/ethanbernstein/• National Geographic: https://www.nationalgeographic.com/• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career• The Story Spine (also known as Pixar’s Story Structure): https://www.storyprompt.com/blog/the-story-spine-also-known-as-pixars-story-structure• Tobi Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke• Job Moves resources: https://www.jobmoves.com/resources• Why Employees Quit: https://hbr.org/2024/11/why-employees-quit—Recommended book:• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:24:55
• A founder’s guide to crisis management | Uri Levine (Waze co-founder, serial entrepreneur)

  Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover:• The two types of startup crisis and how to handle them• Why speed of action is the most important thing• How to keep your team motivated when things look dire• A framework for deciding whether or not to pivot• What to do when product-market fit disappears• How to approach raising money during a crisis• More—Brought to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Rippling—Automate HR, IT, and finance so you can scale faster• OneSchema—Import CSV data 10x faster—Find the transcript at: https://www.lennysnewsletter.com/p/a-founders-guide-to-crisis-management-uri-levine—Where to find Uri Levine:• X: https://twitter.com/urilevine1• LinkedIn: https://www.linkedin.com/in/uri-levine• Website: https://urilevine.com• Book: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637746601/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=&sr=—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) Welcome back, Uri!(05:10) The new chapter: navigating crises(08:15) Types of crises founders face(29:10) Navigating cash crises(38:31) The importance of never giving up(46:26) How to keep people engaged through a crises(47:59) Transparency in crisis management(56:58) Navigating product-market-fit challenges(59:27) Deciding when to pivot or shut down(01:13:34) Real-life startup survival stories(01:17:06) Avoiding and preparing for crises(01:21:21) Final thoughts and book promotion—Referenced:• Waze: https://www.waze.com/• Moovit: https://en.wikipedia.org/wiki/Moovit• Order Chat: https://www.crunchbase.com/organization/order-chat• Fibo: https://finder.startupnationcentral.org/company_page/fibo• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox• TomTom: https://www.tomtom.com/• Khosla Ventures: https://www.khoslaventures.com/• WeSki: https://www.weski.com/• Larry Silverstein: https://en.wikipedia.org/wiki/Larry_Silverstein• Oversee: https://oversee.biz/• Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups• 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• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Zip: https://zip.co/us• Qualcomm: https://www.qualcomm.com/• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_148788—Recommended book:• Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs (updated 2025 version): https://urilevine.com/book/#Pre-order—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:23:45
• OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic)

  Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspective on the cutting edge of AI and large language models. In our conversation, we discuss:• How OpenAI builds product• What people misunderstand about AI model training• Differences between how OpenAI and Anthropic operate• The role of synthetic data in model development• How to build trust between users and AI models• Why she moved from engineering to research• Much more—Brought to you by:• Enterpret—Transform customer feedback into product growth• Vanta—Automate compliance. Simplify security• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen—Where to find Karina Nguyen:• X: https://x.com/karinanguyen_• LinkedIn: https://www.linkedin.com/in/karinanguyen28• Website: https://karinanguyen.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) Introduction to Karina Nguyen(04:42) Challenges in model training(08:21) Synthetic data and its importance(12:38) Creating Canvas(18:33) Day-to-day operations at OpenAI(20:28) Writing evaluations(23:22) Prototyping and product development(26:57) Building Canvas and Tasks(33:34) Understanding the job of a researcher(35:36) The future of AI and its impact on work and education(42:15) Soft skills in the age of AI(47:50) AI’s role in creativity and strategy development(53:34) Comparing Anthropic and OpenAI(57:11) Innovations and future visions(01:07:13) The potential of AI agents(01:11:36) Final thoughts and career advice—Referenced:• What’s in your stack: The state of tech tools in 2025: https://www.lennysnewsletter.com/p/whats-in-your-stack-the-state-of• Anthropic: https://www.anthropic.com/• OpenAI: https://openai.com/• What is synthetic data—and how can it help you competitively?: https://mitsloan.mit.edu/ideas-made-to-matter/what-synthetic-data-and-how-can-it-help-you-competitively• GPQA: https://datatunnel.io/glossary/gpqa/• Canvas: https://openai.com/index/introducing-canvas/• Barret Zoph on LinkedIn: https://www.linkedin.com/in/barret-zoph-65990543/• Mira Murati on LinkedIn: https://www.linkedin.com/in/mira-murati-4b39a066/• JSON Schema: https://json-schema.org/• Anthropic—100K Context Windows: https://www.anthropic.com/news/100k-context-windows• Claude 3 Haiku: https://www.anthropic.com/news/claude-3-haiku• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html• Cursor: https://www.cursor.com/• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management• Lee Byron on LinkedIn: https://www.linkedin.com/in/lee-byron/• GraphQL: https://graphql.org/• Claude in Slack: https://www.anthropic.com/claude-in-slack• Sam Altman on X: https://x.com/sama• Jakub Pachocki on LinkedIn: https://www.linkedin.com/in/jakub-pachocki/• Lennybot: https://www.lennybot.com/• ElevenLabs: https://elevenlabs.io/• Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k• Tuple: https://tuple.app/• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar—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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

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  1:14:33

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