Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer.

What you’ll learn:

• The unexpected insight about virality Rahul gained from LinkedIn’s head of growth.

• Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities.

• The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap.

• How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows.

• The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications.

• How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep.

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Fundrise Flagship Fund—Invest in $1.1 billion of real estate

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra

—

Where to find Rahul Vohra:

• X: https://x.com/rahulvohra

• LinkedIn: https://www.linkedin.com/in/rahulvohra/

• 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) Introduction to Rahul and Superhuman

(05:00) The most pivotal moment in Rahul's career

(07:01) The secret to virality

(11:02) Superhuman’s product evolution and core values

(13:32) Overcoming slowdowns at scale

(18:06) Time management and meditation

(27:35) The role of a president

(30:56) Attention to detail

(43:00) Finding your unique position

(47:32) The power of manual onboarding

(52:37) Mastering product-market fit

(59:33) Game design in business software

(01:05:35) Contrarian pricing strategies

(01:09:29) Leveraging AI

(01:15:40) Transitioning to enterprise solutions

(01:19:08) The Single Decisive Reason framework

(01:22:32) Conclusion and final thoughts

—

Referenced:

• Superhuman: https://superhuman.com/

• Rapportive: https://techcrunch.com/2012/02/22/rapportive-linkedin-acquisition/

• Elliot Shmukler on LinkedIn: https://www.linkedin.com/in/eshmu/

• What Are ‘Whales’ in Video Games: https://gamerant.com/video-games-whales-concept-term-explained/

• Figma: https://www.figma.com/

• Notion: https://www.notion.com/

• Loom: https://www.loom.com/

• How to use Team Comments to reimagine email collaboration: https://blog.superhuman.com/how-to-use-team-comments-to-reimagine-email-collaboration/

• Rajiv Ayyangar’s post on X about Superhuman: https://x.com/rajivayyangar/status/1816176308130570385

• Transcendental Meditation: https://www.tm.org/

• Laurent Valosek on LinkedIn: https://www.linkedin.com/in/laurent-valosek-18708b5a/

• Peak Leadership Institute: https://www.peakleadershipinstitute.com/

• Ed Sim’s website: https://edsim.net/

• Adelle Sans: https://fonts.adobe.com/fonts/adelle-sans

• Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans

• Greenfield project: https://en.wikipedia.org/wiki/Greenfield_project

• Why Mailbox died: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown

• Bill Trenchard on X: https://x.com/btrenchard

• How Superhuman Built an Engine to Find Product-Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

• Using the Sean Ellis Test for Measuring Your Product-Market Fit: https://medium.productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c

• Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/

• The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”): https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis

• The Trouble with Rewards: https://www.kornferry.com/insights/briefings-magazine/issue-13/519-the-trouble-with-rewards

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

•  Van Westendorp Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter

• AI-powered email for high-performing teams: https://superhuman.com/ai

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Single Decisive Reason: decision-making for fast-scaling startups: https://blog.superhuman.com/single-decisive-reason-decision-making-for-fast-scaling-startups/

• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

—

Recommended books:

• Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

—

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.

Susan Cain, author of the groundbreaking bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking, shares a guide for how introverts can thrive in the workplace without sacrificing their authentic selves. Drawing from her extensive research and personal experience, Cain offers a powerful reframing: success doesn’t require becoming more extroverted—it demands becoming more fully yourself.

—

What you’ll learn:

1. A simple definition of introversion and how it differs from shyness—plus a simple two-question test to determine where you fall on the spectrum

2. Five practical tactics introverts can use to be more successful in business while staying true to their natural temperament

3. How to handle challenging workplace scenarios like meetings dominated by loud voices and networking events that drain your energy

4. Specific strategies for managers and founders to create environments where introverted team members can contribute their best work

5. Practical techniques for saying no to energy-draining commitments

6. Strategies for managers to better support and leverage introverted team members

7. Practical advice for raising introverted children to help them develop confidence while honoring their natural temperament

8. Why seeking to become “more extroverted” is the wrong goal—and what to focus on instead to achieve professional success

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Vanta—Automate compliance. Simplify security

• Fundrise Flagship Fund—Invest in $1.1 billion of real estate

—

Find the transcript at: https://www.lennysnewsletter.com/p/the-hidden-power-of-introverts-susan-cain

—

Where to find Susan Cain:

• X: https://x.com/susancain

• LinkedIn: https://www.linkedin.com/in/susancain/

• Website: https://susancain.net/

• Instagram: https://www.instagram.com/susancainauthor/#

• Facebook: https://www.facebook.com/authorsusancain

• Substack: https://thequietlife.net/

—

In this episode, we cover:

(00:00) Introduction to Susan Cain

(05:07) Understanding introversion

(08:55) The spectrum of introversion and extroversion

(13:27) Overcoming public speaking anxiety

(17:13) Learning to embrace your introverted self

(23:16) The power of leaning into your strengths

(24:36) Strategies for introverts to thrive in their career

(34:06) The importance of saying no

(38:35) What to do instead of networking

(41:59) Effective meeting participation for introverts

(47:31) Creating a productive work environment

(51:14) Raising an introverted child

(57:58) Finding the right career fit

(01:08:09) Lightning round and final thoughts

—

Referenced:

• The power of introverts: https://www.ted.com/talks/susan_cain_the_power_of_introverts

• The hidden power of sad songs and rainy days: https://www.ted.com/talks/susan_cain_and_min_kym_the_hidden_power_of_sad_songs_and_rainy_days

• Why bittersweet emotions underscore life’s beauty: https://www.ted.com/talks/susan_cain_why_bittersweet_emotions_underscore_life_s_beauty

• Desensitization: https://en.wikipedia.org/wiki/Desensitization_(psychology)

• Malcolm Gladwell’s website: https://www.gladwellbooks.com/

• Warren Buffett on X: https://x.com/warrenbuffett

• Dale Carnegie speaking courses: https://www.dalecarnegie.com/en/presentation-skills-public-speaking-training

• Bill Gates on X: https://x.com/billgates

• Kathy Fish on LinkedIn: https://www.linkedin.com/in/kathy-fish-23b5777/

• Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello

• Ultraspeaking: https://ultraspeaking.com/lenny/

• Rethinking the Extraverted Sales Ideal: The Ambivert Advantage: https://faculty.wharton.upenn.edu/wp-content/uploads/2013/06/Grant_PsychScience2013.pdf

• Cutco: https://www.cutco.com/

• Tim Ferriss’s post about his new book: https://x.com/tferriss/status/1878936085033791817

•  Mihaly Csikszentmihalyi: https://en.wikipedia.org/wiki/Mihaly_Csikszentmihalyi

• Naval on X: https://x.com/naval

• On saying no: https://www.lennysnewsletter.com/p/how-to-say-no

• Susan Cain—How to Overcome Fear and Embrace Creativity: https://tim.blog/2019/01/24/susan-cain/

• 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

• Renee Wood on LinkedIn: https://www.linkedin.com/in/recoale/

• The Sopranos on Max: https://play.max.com/show/818c3d9d-1831-48a6-9583-0364a7f98453

• The Talented Mr. Ripley on Prime Video: https://www.primevideo.com/detail/The-Talented-Mr-Ripley/0HA0GNFQ4ZXYPDNJHQEENK2Q6Q

• Tugboat Institute: https://www.tugboatinstitute.com/

• Leonard Cohen quote: https://www.goodreads.com/quotes/4484-there-is-a-crack-in-everything-that-s-how-the-light

—

Recommended books:

• Quiet: The Power of Introverts in a World That Can’t Stop Talking: https://www.amazon.com/Quiet-Power-Introverts-World-Talking/dp/0307352153

• Creativity: Flow and the Psychology of Discovery and Invention: https://www.amazon.com/Creativity-Flow-Psychology-Discovery-Invention/dp/0062283251

• Quiet Power: The Secret Strengths of Introverted Kids: https://www.amazon.com/Quiet-Power-Secret-Strengths-Introverted/dp/0147509920

• Gandhi: An Autobiography—The Story of My Experiments with Truth: https://www.amazon.com/Gandhi-Autobiography-Story-Experiments-Truth/dp/0807059099

• Flow: The Psychology of Optimal Experience: https://www.amazon.com/Flow-Psychology-Experience-Perennial-Classics/dp/0061339202

• The Power of Myth: https://www.amazon.com/Power-Myth-Joseph-Campbell/dp/0385418868/

• Bittersweet: How Sorrow and Longing Make Us Whole: https://www.amazon.com/Bittersweet-Oprahs-Book-Club-Longing/dp/0451499794

• Good Energy: The Surprising Connection Between Metabolism and Limitless Health: https://www.amazon.com/Good-Energy-Surprising-Connection-Metabolism/dp/0593712641

• The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X

—

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.

Eric Simons is the founder and CEO of StackBlitz, the company behind Bolt—the #1 web-based AI coding agent and one of the fastest-growing products in history. After nearly shutting down, StackBlitz launched Bolt on Twitter and exploded from zero to $40 million ARR and 1 million monthly active users in about five months.

What you’ll learn:

1. How Bolt reached nearly $40M ARR and 3 million registered users in just five months with a team of only 15 to 20 people

2. How Bolt leverages WebContainer technology—a browser-based operating system developed over seven years—to create a dramatically faster, more reliable AI coding experience than competitors

3. Why Anthropic’s 3.5 Sonnet model was the critical breakthrough that made AI-generated code production-ready and unlocked the entire text-to-app market

4. Why PMs may be better positioned than engineers in the AI era

5. How AI will dramatically reshape company org charts

6. Eric’s wild founder story (including squatting at AOL’s HQ) and how scrappiness fueled his innovation

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Fundrise Flagship Fund—Invest in $1.1 billion of real estate

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

—

Where to find Eric Simons:

• X: https://x.com/ericsimons40

• LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/

• 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) Introduction to Eric Simons and StackBlitz

(04:46) Unprecedented growth and user adoption

(10:40) Demo: Building a Spotify clone with Bolt

(15:28) Expanding to native mobile apps with Expo

(19:09) The journey and technology behind WebContainer

(25:03) Lessons learned and future outlook

(29:15) Post-launch analysis

(34:15) Growing fast with a small team

(41:00) Prioritization at Bolt

(45:51) Tooling and PRD's

(48:42) Integration and use cases of Bolt

(52:24) Limitations of Bolt

(54:24) The role of PMs and developers in the AI era

(59:56) Skills for the future

(01:14:18) Upcoming features of Bolt

(01:20:17) How to get the most out of Bolt

(01:23:00) Eric’s journey and final thoughts

—

Referenced:

• Bolt: https://bolt.new/

• Cursor: https://www.cursor.com/

• Wix: https://www.wix.com/

• Squarespace: https://www.squarespace.com/

• Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/

• Evan Wallace’s website: https://madebyevan.com/

• WebGL: https://en.wikipedia.org/wiki/WebGL

• WebAssembly: https://webassembly.org/

• CloudNine: https://cloudnine.com/

• Canva: https://www.canva.com/

• StackBlitz: https://stackblitz.com/

• 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

• Y Combinator: https://www.ycombinator.com/

• Anthropic: https://www.anthropic.com/

• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/

• Linear: https://linear.app/

• Notion: https://www.notion.com/

• Salesforce: https://www.salesforce.com/

• Atlassian: https://www.atlassian.com/

• Photoshop: https://www.adobe.com/products/photoshop/

• Figma: https://www.figma.com/

• Greenfield projects: https://en.wikipedia.org/wiki/Greenfield_project

• Gartner: https://www.gartner.com/

• OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic): https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen

• Albert Pai on LinkedIn: https://www.linkedin.com/in/albertpai/

• Bolt’s post on X about “Bolt Builders”: https://x.com/boltdotnew/status/1887546089294995943

• Sonnet: https://www.anthropic.com/claude/sonnet

• ChatGPT: https://chatgpt.com/

• Breaking the Rules: The Young Entrepreneur Who Squatted at AOL: https://www.inc.com/john-mcdermott/eric-simons-interview-young-entrepreneur-squatted-at-aol.html

• Imagine K12: http://www.imaginek12.com/

• Geoff Ralston on LinkedIn: https://www.linkedin.com/in/geoffralston/

• AOL: https://www.aol.com/

• Bolt on X: https://x.com/boltdotnew

—

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.

Anton Osika is the co-founder and CEO of Lovable, which is building what they call “the last piece of software”—an AI-powered tool that turns descriptions into working products without requiring any coding knowledge. Since launching three months ago, Lovable hit $4 million ARR in the first four weeks and $10 million ARR in two months with a team of just 15 people, making it Europe’s fastest-growing startup ever.

—

What you’ll learn:

1. Why you need to be in the top 1% of AI tool users

2. Watch Lovable build a functional Airbnb clone in 30 seconds—complete with working features and modern design

3. The unconventional hiring approach that helped build a 15-person team capable of extraordinary execution

4. How traditional product development will look with AI

5. What skills will matter most to product teams going forward

6. How Anton’s team discovered a breakthrough in AI “unsticking itself”

—

Brought to you by:

• Sinch—Build messaging, email, and calling into your product

• Persona—A global leader in digital identity verification

• Fundrise Flagship Fund—Invest in $1.1 billion of real estate

—

Find the transcript at: https://www.lennysnewsletter.com/p/building-lovable-anton-osika

—

Where to find Anton Osika:

• X: https://x.com/antonosika

• LinkedIn: https://www.linkedin.com/in/antonosika/

—

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 Anton and Lovable

(05:12) Lovable’s rapid growth

(09:39) Live demo: Building an Airbnb clone

(18:34) Tips for mastering Lovable

(21:42) The origin story

(26:50) Scaling laws and getting AI unstuck

(33:20) Reliability and unique features

(36:25) The vision and future of Lovable

(38:14) Skills and job market evolution in the age of AI

(40:30) Hiring philosophy and team dynamics

(46:21) Building in Europe

(48:02) Prioritization and product roadmap

(51:38) Tools and work environment

(53:17) Tactics for moving fast

(54:37) Advice for building product teams

(57:11) Empowering non-technical founders

(58:31) Future developments and user support

(01:01:23) Failure corner

(01:05:20) Final thoughts and advice

—

Referenced:

• Lovable: https://lovable.dev/

• Lovable Launched: https://launched.lovable.app/

• Cloudflare: https://www.cloudflare.com/

• Supabase: https://supabase.com/

• GPT engineer: https://github.com/gpt-engineer-org/gptengineer.app

• Microsoft Copilot: https://copilot.microsoft.com/chats/cmFw8dTsGU8D6b9siqQ6U

• Fabian Hedin on LinkedIn: https://www.linkedin.com/in/fabian-hedin-2377b0144/

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Replit: https://replit.com/

• Cursor: https://www.cursor.com

• Bolt: https://bolt.new/

• GitHub: https://github.com/

• Lane Shackleton on LinkedIn: https://www.linkedin.com/in/laneshackleton/

• FigJam: https://www.figma.com/figjam/

• Linear: https://linear.app/

• Sana Labs: https://sanalabs.com/

• Duolingo: https://www.duolingo.com/

• Claude: https://claude.ai/

• ChatGPT: https://chatgpt.com/

• Lovable on X: https://x.com/Lovable_dev

—

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.

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 rewrites

3. Why Notion prioritized systems over headcount, keeping the team small and focused even at scale

4. Why Ivan believes in craft and values as the foundation for product development, balancing technical excellence with aesthetic sensibility

5. The surprising story of how Notion nearly collapsed during Covid when their single database almost ran out of space with only weeks to spare

6. Community-led growth tactics

7. Ivan’s unique journey from a small town in China

8. 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/. For inquiries about sponsoring the podcast, email [email protected].

—

Lenny may be an investor in the companies discussed.

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

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• 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.

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 rule

2. The seemingly crazy yet brilliant way this idea survived multiple CEO changes—from Jack to Parag to Elon

3. How this project started with a dumpster fire GIF (literally)—the untold backstory of its early launch

4. The secret to running ultra-fast, high-impact product teams—no OKRs, no Jira; just one Google Doc

5. 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:

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• 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.

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:

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• 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.

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.

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.

Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss:

• Why complexity kills entrepreneurship

• How to develop and leverage your unique talent stack

• How specifically Tobi approaches thinking from first principles

• The importance of focusing on unquantifiable qualities like joy and delight

• Why Tobi works backward from a 100-year vision

• Why metrics should support decisions, not make them

• The power of following your curiosity

• What Tobi believes it takes to be a great product leader

• Much more

—

Brought to you by:

• Sinch—Build messaging, email, and calling into your product

• Liveblocks—Ready-made collaborative features to drop into your product

• Loom—The easiest screen recorder you’ll ever use

—

Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

—

Where to find Tobi Lütke:

• X: https://x.com/tobi

• LinkedIn: https://www.linkedin.com/in/tobiaslutke/

• Website: https://tobi.lutke.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) Welcome and introduction

(04:17) The Tobi tornado

(07:10) Maximizing human potential

(11:05) Education and personal growth

(16:47) Operating without KPIs

(25:00) First-principles thinking

(40:04) Remote work

(45:59) Why Tobi never stopped coding

(54:46) Embracing disagreement

(01:01:27) The 100-year vision

(01:09:29) Balancing tactics and positioning

(01:17:15) Encouraging entrepreneurship

(01:19:34) The power of good UX

(01:28:42) The talent stack and unique opportunities

(01:34:30) The role of passion in product development

(01:36:39) Final thoughts and farewell

—

Referenced:

• 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

• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams

• The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis

• Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build

• IRC: https://en.wikipedia.org/wiki/IRC

• Goodhart’s law: https://en.wikipedia.org/wiki/Goodhart%27s_law

• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/

• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product

• The Last Dance on Netflix: https://www.netflix.com/title/80203144

• Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f

• Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property

• Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa

• Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/

• World of Warcraft: https://worldofwarcraft.blizzard.com

• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/

• Monorepo: https://en.wikipedia.org/wiki/Monorepo

• The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/

• Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify

• Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment

• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/

• We are the Web: https://link.wired.com/public/32945405

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Recommended books:

• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713

• The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

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Lenny may be an investor in the companies discussed.