Lenny’s Podcast: Product | Growth | Career

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.

In this episode, you’ll learn:

1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI

2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills

3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers

4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence

5. How “vibe coding” is changing how companies operate

6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)

7. “Model maximalism” and why today’s AI is the worst you’ll ever use again

8. Practical prompting techniques that improve AI interactions, including example-based prompting

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Brought to you by:

• Eppo—Run reliable, impactful experiments

• Persona—A global leader in digital identity verification

• OneSchema—Import CSV data 10x faster

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Where to find Kevin Weil:

• X: https://x.com/kevinweil

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

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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) Kevin’s background

(04:06) OpenAI’s new image model

(06:52) The role of chief product officer at OpenAI

(10:18) His recruitment story and joining OpenAI

(17:20) The importance of evals in AI

(24:59) Shipping quickly and consistently

(28:34) Product reviews and iterative deployment

(39:35) Chat as an interface for AI

(43:59) Collaboration between researchers and product teams

(46:41) Hiring product managers at OpenAI

(48:45) Embracing ambiguity in product management

(51:41) The role of AI in product teams

(53:21) Vibe coding and AI prototyping

(55:55) The future of product teams and fine-tuned models

(01:04:36) AI in education

(01:06:42) Optimism and concerns about AI’s future

(01:16:37) Reflections on the Libra project

(01:20:37) Lightning round and final thoughts

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Referenced:

• OpenAI: https://openai.com/

• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/

• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/

• Waymo: https://waymo.com/

• X: https://x.com

• Facebook: https://www.facebook.com/

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

• Planet: https://www.planet.com/

• Sam Altman on X: https://x.com/sama

• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k

• OpenAI evals: https://github.com/openai/evals

• Deep Research: https://openai.com/index/introducing-deep-research/

• Ev Williams on X: https://x.com/ev

• OpenAI API: https://platform.openai.com/docs/overview

• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• StackBlitz: https://stackblitz.com/

• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet

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

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i

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

• Figma: https://www.figma.com/

• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/

• Andrej Karpathy on X: https://x.com/karpathy

• Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/

• Cursor: https://www.cursor.com/

• Windsurf: https://codeium.com/windsurf

• GitHub Copilot: https://github.com/features/copilot

• Patrick Srail on X: https://x.com/patricksrail

• Khan Academy: https://www.khanacademy.org/

• CK-12 Education: https://www.ck12.org/

• Sora: https://openai.com/sora/

• Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115

• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)

• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/

• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/

• Peter Zeihan on X: https://x.com/PeterZeihan

• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R

• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G

• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

• MySQL: https://www.mysql.com/

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Recommended books:

• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X

• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341

• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X

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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.

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.

What you’ll learn:

1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in

2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings

3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning

4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure

5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it

6. The power of “signposting”—and why executives skim your docs without it

7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction

8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives

9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders

10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out

11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today

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Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

—

Where to find Wes Kao:

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

• Website: https://www.weskao.com/

• Maven course: https://maven.com/wes-kao/executive-communication-influence

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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) Introduction to Wes Kao

(05:34) Working with Wes

(06:58) The importance of communication

(10:44) Sales before logistics

(18:20) Being concise

(24:31) Books to help you become a better writer

(27:30) Signposting and formatting

(32:05) How to develop and practice your communication skills

(40:41) Slack communication

(42:23) Confidence in communication

(50:17) The MOO framework

(54:00) Staying calm in high-stakes conversations

(57:36) Which tactic to start with

(58:53) Effective tactics for managing up

(01:04:53) Giving constructive feedback: strategy, not self-expression

(01:09:39) Delegating effectively while maintaining high standards

(01:16:36) The swipe file: collecting inspiration for better communication

(01:19:59) Leveraging AI for better communication

(01:22:01) Lightning round

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Referenced:

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

• Communication is the job: https://boz.com/articles/communication-is-the-job

• Maven: https://maven.com/

• Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics

• How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise

• Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive

• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

• Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language

• Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it

• Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression

• 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

• The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining

• Swipe file: https://en.wikipedia.org/wiki/Swipe_file

• Apple Notes: https://apps.apple.com/us/app/notes/id1110145109

• Claude: https://claude.ai/new

• ChatGPT: https://chatgpt.com/

• Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1

• The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221

• Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/

• The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/

• Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A

• 1,000,000: https://www.lennysnewsletter.com/p/1000000

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Recommended books:

• On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/

• Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/

• On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375

• Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884

• Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/

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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.

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to them them escape the cycle of endless sprints, missed deadlines, and dragging projects.

What you’ll learn:

1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.

2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.

3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.

4. Why most teams struggle with too little detail in their planning, not too much.

5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.

6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.

7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.

8. The clear warning signs that your current development process is failing before it’s too late to change course.

9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.

10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.

11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.

12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.

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Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Merge—A single API to add hundreds of integrations into your app

• Airtable ProductCentral—Launch to new heights with a unified system for product development

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Where to find Ryan Singer:

• X: https://x.com/rjs

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

• Website: https://www.ryansinger.co/

• Course: https://www.ryansinger.co/srl/

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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) Ryan’s background

(04:38) The origins of Shape Up

(07:40) Implementing Shape Up in different companies

(09:56) How Shape Up is different

(19:02) The core elements of Shape Up

(26:29) Shaping sessions and timeboxing

(37:23) Flexible sprint planning

(38:56) The output of a shaping session

(46:57) Balancing detail and flexibility

(53:50) A deep dive into shaping sessions

(01:01:32) Fat marker sketches

(01:02:48) Getting started using Shape Up

(01:13:20) Signs it's time to try the Shape Up method

(01:18:25) Feature factories

(01:25:59) The role of the PM in Shape Up

(01:28:26) What makes Basecamp unique

(01:35:55) The second edition of the book

(01:38:30) Linking product strategy and shaping

(01:41:53) Conclusion and final thoughts

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Referenced:

• Basecamp: https://basecamp.com/

• David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/

• Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/

• Intercom: https://www.intercom.com/

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta

• Scrum: https://www.scrum.org/

• 37signals: https://37signals.com/

• Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/

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Recommended books:

• Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup

• Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/

• Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581

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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.

Gaurav Misra is the co-founder and CEO of Captions, an AI-powered video creation company and one of the most successful consumer AI products in the world today. Previously he was a product leader at Snap, where he created the design engineering function and spent years helping develop features used by hundreds of millions of users worldwide. With a background in both engineering and design, Gaurav brings a unique cross-functional perspective to product development.

What you’ll learn:

1. Why the “ship a marketable feature every week” approach helps his team stay focused and the product stay top of mind for users amid constant AI breakthroughs

2. How to balance rapid shipping with maintaining quality by cutting scope rather than compromising on timelines

3. The “secret roadmap” strategy that helps Captions develop breakthrough features competitors never see coming

4. Why taking on strategic technical debt is essential for startups to outpace larger companies

5. How Captions accidentally ignored their most successful product for 1.5 years (and why it still grew to 500K users with no updates or support)

6. How Snap’s unique product development approach—with designers functioning as PMs—enabled their success as the last major social network to break through

7. Why AI video will transform marketing before other industries

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Brought to you by:

• Brex — The banking solution for startups

• Paragon—Ship every SaaS integration your customers want

• Coda—The all-in-one collaborative workspace

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Find the transcript at: https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

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Where to find Gaurav Misra:

• X: https://x.com/gmharhar

• LinkedIn: https://www.linkedin.com/in/gamisra1/

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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) Gaurav’s background

(04:47) The exciting era of AI and startups

(09:30) Staying top of mind

(11:26) Tips for staying focused

(13:14) Shipping marketable features weekly

(19:03) Managing technical debt in startups

(25:31) Snap’s unique product development approach

(32:09) Brainstorming with AI

(35:09) What Snap got right

(41:06) Scaling with a small, agile team

(49:33) The shift toward prototyping in product management

(51:47) The product manager role

(55:40) Snap’s mission and product decisions

(01:02:13) The future of AI-generated video

(01:10:20) Leveraging AI for marketing

(01:14:37) Failure corner

(01:20:21) Lightning round and closing thoughts

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Referenced:

• Snap: https://www.snap.com/

• Captions: https://www.captions.ai/

• Iron Man on Disney+: https://www.disneyplus.com/movies/iron-man/6aM2a8mZATiu

• J.A.R.V.I.S.: https://en.wikipedia.org/wiki/J.A.R.V.I.S.

• Cursor: https://www.cursor.com/

• Devin: https://devin.ai/

• Eye contact: https://www.captions.ai/eye-contact

• Nvidia: https://www.nvidia.com

• Descript: https://www.descript.com

• Evan Spiegel on LinkedIn: https://www.linkedin.com/in/evan-spiegel-8ab74034a/

• TikTok: https://www.tiktok.com/

• Spotlight: https://www.snapchat.com/spotlight/

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Patrick Collison on X: https://x.com/patrickc

• DeepSeek: https://www.deepseek.com/

• ByteDance Goku: New video generation AI model, better than OpenAI Sora: https://medium.com/data-science-in-your-pocket/bytedance-goku-new-video-generation-ai-model-better-than-openai-sora-56c017a320a5

• Will Smith eating spaghetti and other weird AI benchmarks that took off in 2024: https://techcrunch.com/2024/12/31/will-smith-eating-spaghetti-and-other-weird-ai-benchmarks-that-took-off-in-2024/

• Silo on AppleTV+: https://tv.apple.com/us/show/silo/umc.cmc.3yksgc857px0k0rqe5zd4jice

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

• Linear: https://linear.app/

• Superhuman: https://superhuman.com/

• Notion: https://www.notion.com

• Perplexity: https://www.perplexity.ai/

• OmniHuman-1 AI Video Generation Looks Too Real: https://www.youtube.com/watch?v=fY0KB516m-E

—

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.

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

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Where to find Rahul Vohra:

• X: https://x.com/rahulvohra

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

• Email: Rahul@superhuman.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) 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

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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 podcast@lennyrachitsky.com.

—

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 podcast@lennyrachitsky.com.

—

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: Eric@stackblitz.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 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 podcast@lennyrachitsky.com.

—

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 podcast@lennyrachitsky.com.

—

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 podcast@lennyrachitsky.com.

—

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

• 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 podcast@lennyrachitsky.com.

—

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:

• 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.

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 podcast@lennyrachitsky.com.

—

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 podcast@lennyrachitsky.com.

—

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 podcast@lennyrachitsky.com.

—

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

—

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/

—

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.

Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss:

• Why speed and quality aren’t actually at odds

• Linear’s unique approach to product development

• Nan’s systematic approach to creativity

• Linear’s philosophy on deadlines

• The “double triangle” framework for product management

• Nan’s approach to landing his dream product roles

• Much more

—

Brought to you by:

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

• Paragon—Ship every SaaS integration your customers want

• Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

—

Where to find Nan Yu:

• X: https://x.com/thenanyu

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

—

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 Nan Yu and Linear

(04:54) Survey insights: Linear vs. Jira

(07:51) The speed vs. quality myth

(09:24) Building and iterating quickly

(15:31) Avoiding bloat in enterprise software

(23:57) Understanding user needs deeply

(30:09) How to approach customer calls

(34:10) Creating strong emotional hooks

(40:31) Managing the product backlog

(44:46) Systemizing creativity

(48:16) Demo: Saving drafts in Linear

(51:38) Breaking constraints and building at extremes

(54:15) Adopting new tools

(58:22) The “double triangle” framework for product management

(01:04:23) Effective job-hunting strategies for PMs

(01:09:15) Thoughts on deadlines

(01:14:15) Lightning round

—

Referenced:

• Jira: https://www.atlassian.com/software/jira

• Linear: https://linear.app/

• Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459

• Magnus Carlsen on X: https://x.com/magnuscarlsen

• Hikaru Nakamura on X: https://x.com/gmhikaru

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• Customer Request feature on Linear: https://linear.app/customer-requests

• Everlane: https://www.everlane.com/

• Schlep Blindness: https://paulgraham.com/schlep.html

• Linear’s triage tool: https://linear.app/docs/triage

• Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Mode: https://mode.com/

• The Diplomat on Netflix: https://www.netflix.com/title/81288983

• Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/

—

Recommended books:

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/

—

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.

Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares:

• His playbook for developing a product strategy

• The difference between “small s” and “big S” strategy

• How to run strategy sprints

• Who should be involved in strategy work

• Common pitfalls in strategy development

• The role of AI in future strategy development

• More

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Airtable ProductCentral—Launch to new heights with a unified system for product development

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/an-operators-guide-to-product-strategy-chandra-janakiraman

—

Where to find Chandra Janakiraman:

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

—

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) Chandra’s background

(04:47) The importance of strategy

(12:40) Defining product strategy

(15:42) Developing a winning strategy: an overview

(18:51) The preparation phase

(30:46) The strategy sprint process

(45:51) The design sprint

(51:19) Document writing

(57:39) Rolling out your strategy

(01:01:28) Resourcing and roadmapping

(01:04:42) Strategy lessons from Zynga

(01:11:34) Strategy lessons from Meta

(01:15:55) Big S strategy

(01:26:58) AI in strategy formulation

(01:38:12) Final thoughts and lightning round

—

Referenced:

• Headspace: https://www.headspace.com/

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• VRChat: https://hello.vrchat.com/

• Andrew Chen on LinkedIn: https://www.linkedin.com/in/pmandrewchen/

• Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq

• How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

• Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

• Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures): https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis

• Chandra’s flow chart: https://docs.google.com/document/d/1SLmQ0oRFadzJnNM3MJetnLUvB18U4W4GXU4KtJ2ujEQ/edit?tab=t.0

• Chandra’s strategy template: https://docs.google.com/document/d/1iNeYUaMnpicvkpVZO-gj9cCxLeHfWN0xtGm_QoxgemE/edit?tab=t.0#heading=h.5d3jz6v86yrs

• Zynga: https://www.zynga.com/

• David Foster Wallace’s quote about water: https://www.goodreads.com/quotes/97082-there-are-these-two-young-fish-swimming-along-and-they

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

• Elon Musk’s quote: https://www.youtube.com/shorts/wf8TadbGYok

• Concept car: https://en.wikipedia.org/wiki/Concept_car

• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview

• Armand Ruiz on LinkedIn: https://www.linkedin.com/in/armand-ruiz/

• What is a multi-armed bandit? Full explanation: https://amplitude.com/explore/experiment/multi-armed-bandit

• IF on Prime Video: https://www.amazon.com/IF-John-Krasinski/dp/B0CW19SCVW

• Dune: Part 2 on AppleTV+: https://tv.apple.com/us/movie/dune-part-two/umc.cmc.363aycnv6vy9qgekvew6fveb9

• Dune Prophecy on Max: https://www.max.com/shows/dune-prophecy-2024/57660b16-a32a-476f-89da-3302ac379e91

• Capybara Go on the App Store: https://apps.apple.com/ph/app/capybara-go/id6596787726

• Bluesky: https://bsky.app/

• Steve Jobs: The Lost Interview on Prime Video: https://www.amazon.com/Steve-Jobs-Lost-Interview/dp/B01IJD1BES

—

Recommended books:

• The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1599869772

• Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487/

• Good Strategy Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239/

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

• Sprint: https://www.amazon.com/SPRINT-Jake-Zeratsky-Knapp/dp/0593076117

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

• 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 Ten Faces of Innovation: Strategies for Heightening Creativity: https://www.amazon.com/dp/0385512074

—

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.

Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss:

• 10 growth tactics that never work

• Her 3 favorite growth frameworks

• How to increase your career optionality

—

Brought to you by:

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

• Vanta—Automate compliance. Simplify security

• OneSchema—Import CSV data 10x faster

—

Find the transcript at: https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna

—

Where to find Elena Verna:

• Newsletter: https://www.elenaverna.com/

• X: https://x.com/elenaverna

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

—

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, Elena!

(06:02) Common mistakes growth teams make

(08:31) #1: Hiring for growth roles too soon

(15:09) #2: Hiring a head of growth to fix your problems

(19:20) #3: Doing a rebrand to drive growth

(25:11) #4: Obsessing over your competition

(34:00) #5: Believing that your problems are unique

(42:32) #6: Prioritizing other growth channels above earned channels

(50:55) #7: Failing to evolve your growth model

(01:01:06) #8: Not hiring advisors

(01:05:55) #9: Over-experimenting

(01:10:44) #10: Color optimizations, third-party signups, one-email wonders, and removing friction

(01:15:00) Elena’s favorite growth frameworks

(01:18:50) Contrarian corner: full-time jobs

(01:26:05) Lightning round and final thoughts

—

Referenced:

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• Six rules of hiring for growth: https://www.lennysnewsletter.com/p/hiring-growth

• Figma: https://www.figma.com/

• Miro: https://www.figma.com/

• Notion: https://www.figma.com/

• Carol Wong on LinkedIn: https://www.linkedin.com/in/carol-wong-14133927/

• Dropbox: https://www.dropbox.com/

• The Law of Shitty Clickthroughs: https://andrewchen.com/the-law-of-shitty-clickthroughs/

• Miroverse: https://miro.com/miroverse/

• GitHub: https://github.com/

• My 9 Favorite Growth Frameworks: https://www.elenaverna.com/p/my-9-favorite-growth-frameworks

• Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loops

• Racecar Growth Framework: https://www.reforge.com/blog/racecar-growth-framework

• The Adjacent User: https://andrewchen.com/the-adjacent-user-theory/

• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

• Why I’m Unquitting Full-Time Roles: https://www.elenaverna.com/p/why-im-unquitting-full-time-roles

• Noah Smith’s newsletter: https://www.noahpinion.blog/

• Beef on Netflix: https://www.netflix.com/title/81447461

• Veep on Max: https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a

• The Last of Us on Max: https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a

• Heated boots: https://www.amazon.com/heated-boots/s?k=heated+boots

• Airpods Max: https://www.apple.com/airpods-max/

• Memes by Elena: https://www.elenaverna.com/p/ten-funniest-growth-memes

—

Recommended books:

• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/

• The Martian: https://www.amazon.com/Martian-Andy-Weir/dp/0553418025

• We Are Legion (Bobiverse #1): https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587

• Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285

—

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.

Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss:

• Why everything worthwhile requires suffering

• Why most people operate on autopilot, and how to break free

• The “genie methodology” for discovering your true path

• The Nine Lives exercise for exploring different life possibilities

• How to overcome limiting beliefs that hold you back

• Why “not now” is often just another way of saying “never”

• More

—

Brought to you by:

• Merge—A single API to add hundreds of integrations into your app

• Persona—A global leader in digital identity verification

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver

—

Where to find Graham Weaver:

• LinkedIn: https://www.linkedin.com/in/graham-weaver-2b79

• Instagram: https://www.instagram.com/grahamcweaver

• YouTube: https://www.youtube.com/@grahamcweaver

• Website: https://www.grahamweaver.com

• TikTok: https://www.tiktok.com/@grahamcweaver

—

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) Graham’s background

(05:30) Helping students find their true path

(07:40) The genie methodology

(12:36) Breaking free from autopilot mode

(17:54) Identifying and overcoming limiting beliefs

(20:33) Teaching entrepreneurship and personal fulfillment

(22:53) The reality of long-term success

(35:14) The role of accountability and executive coaching

(40:22) Daily goal setting for success

(43:11) The Nine Lives framework

(48:01) The dangers of the “not now” mentality

(55:27) Navigating life’s transitions

(57:19) Failure corner

(01:00:24) When to quit and when to persevere

(01:02:18) Final thoughts and lightning round

—

Referenced:

• Setting Goals: Demystified: https://www.grahamweaver.com/blog/goals

• Tony Robbins’s website: https://www.tonyrobbins.com

• Alpine Investors: https://alpineinvestors.com

• Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: https://www.grahamweaver.com/blog/stanford-graduate-business-school-last-lecture-2024

• I turned 50 today. Here is the most important thing I learned in my first half century: https://www.grahamweaver.com/blog/turning-50

• Where the Crawdads Sing on Prime Video: https://www.amazon.com/Where-Crawdads-Sing-Daisy-Edgar-Jones/dp/B0B5KBKDNL

• Chilipad Cube Bed Cooling System: https://www.amazon.com/Chilipad-Cube-Bed-Cooling-System/dp/B07GT9MYRW

• Sleepme OOLER Sleep System: https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G

• Eightsleep: https://www.eightsleep.com

• Howard Thurman’s quote: https://www.goodreads.com/quotes/6273-don-t-ask-what-the-world-needs-ask-what-makes-you

—

Recommended books:

• Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752

• The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379

• Don’t Believe Everything You Think: Why Your Thinking Is the Beginning and End of Suffering: https://www.amazon.com/Dont-Believe-Everything-Think-Expanded/dp/B0D47VYQMY

• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

—

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.

Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss:

• Key indicators that it’s time to hire PMs

• How to build your early PM team

• Why founders should initially take on the product manager role themselves

• How to attract top PM talent

• What she’s learned about going multi-product

• A case for investing in quality

• More

—

Skip the Mercury Personal waitlist: https://mercurytechnologies.typeform.com/lenny

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• OneSchema—Import CSV data 10x faster

• Airtable ProductCentral—Launch to new heights with a unified system for product development

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-to-build-your-product-team-from-scratch-rohini-pandhi

—

Where to find Rohini Pandhi:

• X: https://x.com/rohinip

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

—

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) Rohini’s background

(05:00) The role of product managers at Mercury

(09:51) Key indicators that it’s time to hire PMs

(13:18) Building the product team at Mercury

(19:53) Why you should avoid hiring PMs too early

(22:26) The different flavors of product management

(26:15) How to attract top talent

(35:59) Advocating for quality in product development

(44:10) Going multi-product

(46:37) Organizational structure for multi-product success

(50:57) Organizational culture for multi-product success

(52:07) Customer obsession and product development

(57:36) More lessons from going multi-product

(01:05:57) Transparent Collective: supporting underrepresented founders

(01:09:54) Lightning round

—

Referenced:

• Immad Akhund on X: https://x.com/immad

• Mercury: https://mercury.com

• Square: https://squareup.com

• Product management career ladders: https://www.lennysnewsletter.com/p/product-management-career-ladders

• Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7

• Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860

• What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html

• Mercury Bill Pay: https://mercury.com/bill-pay

• Zip: https://zip.co

• Jira: https://www.atlassian.com/software/jira

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

• Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product

• Gokul Rajaram on X: https://x.com/gokulr

• Transparent Collective: https://www.transparentcollective.com

• 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/16-reading-tips-from-naval-ravikant

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking

• Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses

• Severance on AppleTV+: https://tv.apple.com/us/show/severance

• Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent

• Waymo: https://waymo.com

• Adam Robinson on X: https://x.com/IAmAdamRobinson

• Cyan Banister—From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More): https://tim.blog/2024/11/28/cyan-banister

• Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson

• Jobs at Mercury: https://mercury.com/jobs

—

Recommended books:

• Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890

• The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927

• Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367

• The Song of Achilles: https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627

—

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.

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about:

• The three eras of Dropbox’s growth and evolution

• The challenges he’s faced over the past 18 years

• What he learned about himself

• How he’s been able to manage his psychology as a founder

• The importance of maintaining your learning curve

• Finding purpose beyond metrics and growth

• The micro, macro, and meta aspects of building companies

• Much more

—

Brought to you by:

• Paragon—Ship every SaaS integration your customers want

• Explo—Embed customer-facing analytics in your product

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

—

Where to find Drew Houston:

• X: https://x.com/drewhouston

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

—

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 Drew and Dropbox

(04:44) The three eras of Dropbox

(07:53) The first era: Viral growth and early success

(14:19) The second era: Challenges and competition

(20:49) Strategic shifts and refocusing

(29:36) Personal reflections and leadership lessons

(40:19) Unlocking mindfulness and building support systems

(43:14) The Enneagram test

(50:35) The challenges of being a founder CEO

(58:11) The third era: Rebooting the team and core business

(01:22:41) Lessons and advice for aspiring founders

(01:27:46) Balancing personal and professional growth

(01:42:38) Final reflections and future outlook

—

Referenced:

• Dropbox: https://www.dropbox.com/

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

• Paul Graham’s website: https://www.paulgraham.com/

• Hacker News: https://news.ycombinator.com/

• Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/

• Sequoia Capital: https://www.sequoiacap.com/

• Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/

• Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/

• TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/

• Dropbox viral demo: https://youtu.be/7QmCUDHpNzE

• Digg: https://digg.com/

• Reddit: https://www.reddit.com/

• Hadi and Ali Partovi: https://www.partovi.org/

• Zynga: https://www.zynga.com/

• Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc

• Dropbox Carousel: https://en.wikipedia.org/wiki/Dropbox_Carousel

• Dropbox Is Buying Mega-Hyped Email Startup Mailbox: https://www.businessinsider.com/dropbox-is-buying-mega-hyped-email-startup-mailbox-2013-3

• 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin

• Intel: https://www.intel.com/

• Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore

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

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

• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)

• Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/

• The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Ben Horowitz on X: https://x.com/bhorowitz

• Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker

• GitLab: https://about.gitlab.com/

• Automattic: https://automattic.com/

• Dropbox Dash: https://www.dash.dropbox.com/

• Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/welcome-command-e-to-dropbox-

• StarCraft: https://en.wikipedia.org/wiki/StarCraft_(video_game)

• Procter & Gamble and the Beauty of Small Wins: https://hbr.org/2009/10/the-beauty-of-small-wins

• Teaching Smart People How to Learn: https://hbr.org/1991/05/teaching-smart-people-how-to-learn

—

Recommended books:

• Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business: https://www.amazon.com/Guerilla-Marketing-Inexpensive-Strategies-Business/dp/0618785914

• Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X

• High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/

• Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821

• Zone to Win: Organizing to Compete in an Age of Disruption: https://www.amazon.com/Zone-Win-Organizing-Compete-Disruption/dp/1682302113

• Warren Buffett’s books: https://www.amazon.com/warren-buffett-Books/s?k=warren+buffett&rh=n%3A283155

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239

• Invent and Wander: The Collected Writings of Jeff Bezos: https://www.amazon.com/Invent-Wander-Collected-Writings-Introduction/dp/1647820715/

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE

—

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.

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss:

• The psychology behind why we avoid difficult conversations

• Specific scripts for having five common difficult conversations

• How to handle defensive reactions in the moment

• The three questions you should end every meeting with

• “The founder prenup” that every founding team should work through

• Common leadership myths

• Stories of failure from Alisa’s career

—

Brought to you by:

• Eppo—Run reliable, impactful experiments

• Rippling—Automate HR, IT, and finance so you can scale faster

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

—

Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn

—

Where to find Alisa Cohn:

• X: https://x.com/AlisaCohn

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

• Website: https://www.alisacohn.com

• Podcast: https://www.alisacohn.com/podcast

—

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) Alisa’s background

(04:48) Having difficult conversations

(12:48) Scripts for performance feedback

(20:20) How to respond when someone is defensive or upset

(25:07) Scripts for handling promotion disappointments

(31:00) Scripts for handling terminations

(35:44) The importance of positive feedback

(38:49) Understanding your job as a leader

(44:55) Recognizing your own blind spots

(49:38) Three vital questions to ask in every meeting

(55:57) The founder prenup

(01:08:24) Failure corner

(01:13:00) Final thoughts and lightning round

—

Referenced:

• Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

• How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson

• Joe Gebbia on X: https://x.com/jgebbia

• Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425

• Core Values List: https://jamesclear.com/core-values

• How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing

• Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii

• Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ

• Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on

—

Recommended books:

• From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473

—

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.

Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss:

• Gong’s unique approach to working with design partners

• Their unique pod model

• Why Eilon makes big decisions quickly

• Lessons learned from being early in AI

• The power of extreme focus

• His “spiral method” for learning complex topics quickly

• How to maintain quality while optimizing for speed

—

Brought to you by:

• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs

• Think Fast Talk Smart—Tools and techniques to help you communicate more effectively

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/inside-gong-eilon-reshef

—

Where to find Eilon Reshef:• LinkedIn: https://www.linkedin.com/in/eilonreshef

—

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) Eilon’s background

(04:20) The pod model

(06:33) Working with design partners

(09:13) Finding and coordinating design partners

(13:12) Balancing customer feedback and vision

(15:10) Gong's 95% feature adoption

(17:05) The importance of autonomy and trust

(23:30) How to implement this unique way of working

(27:15) Speed and decision-making

(31:47) Early AI adoption and lessons learned

(35:50) Building effective AI teams

(38:16) The spiral method for learning

(41:36) Narrowing down the initial customer profile

(44:24) Failure corner

(46:35) Lightning round

—

Referenced:

• Gong: https://www.gong.io

• Cisco: https://www.cisco.com/

• How Gong builds product: https://www.lennysnewsletter.com/p/how-gong-builds-product

• What is Montessori education?: https://amshq.org/About-Montessori/What-Is-Montessori

• Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov

• Amit Bendov on LinkedIn: https://www.linkedin.com/in/amitbendov/

• Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the

• Nvidia: https://www.nvidia.com

• Figma: https://www.figma.com

• The Spiral Method: https://www.gong.io/blog/using-the-spiral-method/

• Webex: https://www.webex.com/

• L’Oréal: https://www.lorealparisusa.com/

• American Express: https://www.americanexpress.com/

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Dishwasher basket: https://www.amazon.com/Munchkin-High-Capacity-Dishwasher-Basket/dp/B07ZPMYKKS/

• What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Hanlon’s razor: https://en.wikipedia.org/wiki/Hanlon%27s_razor

• Sabich: https://en.wikipedia.org/wiki/Sabich#Ingredients_and_description

• Careers at Gong: https://www.gong.io/careers

—

Recommended books:

• Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM

• “The Machine That Won the War”: https://www.goodreads.com/book/show/18402398-the-machine-that-won-the-war

• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986

• The Ideal Executive: https://www.amazon.com/Ideal-Executive-Ichak-Kalderon-Adizes/dp/0937120030/

• Crucial Conversations: Tools for Talking when Stakes Are High: https://www.amazon.com/Crucial-Conversations-Tools-Talking-Stakes/dp/1260474186/

—

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.

Shaun Clowes is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversation, we discuss:

• Why most PMs are bad, and how to fix this

• Why great AI products are all about the data

• Why he changed his mind about being data-driven

• How to build your B2B growth team

• How to choose your next career stop

• Much more

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• BuildBetter—AI for product teams

• Wix Studio—The web creation platform built for agencies

—

Find the transcript at: https://www.lennysnewsletter.com/p/why-great-ai-products-are-all-about-the-data-shaun-clowes

—

Where to find Shaun Clowes:

• X: https://x.com/ShaunMClowes

• LinkedIn: https://www.linkedin.com/in/shaun-clowes-80795014/

• Website: https://shaunclowes.com/about-shaun

• Reforge: https://www.reforge.com/profiles/shaun-clowes

—

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) Shaun’s background

(05:08) The state of product management

(09:33) Becoming a 10x product manager

(13:23) Specific ways to leverage AI in product management

(17:15) Feedback rivers

(19:20) AI's impact on data management

(24:35) The future of enterprise businesses with AI

(35:41) Data-driven decision-making

(45:50) Building effective growth teams

(50:18) The evolution of product-led growth

(56:16) Career insights and decision-making

(01:07:45) Failure corner

(01:12:32) Final thoughts and lightning round

—

Referenced:

• Steve Blank’s website: https://steveblank.com/

• Getting Out of the Building. 2 Minutes to See Why: https://www.youtube.com/watch?v=TbMgWr1YVfs

• OpenAI: https://openai.com/

• Claude: https://claude.ai/

• Sachin Rekhi on LinkedIn: https://www.linkedin.com/in/sachinrekhi/

• Video: Building Your Product Intuition with Feedback Rivers: https://www.sachinrekhi.com/video-building-your-product-intuition-with-feedback-rivers

• Confluent: https://www.confluent.io

• Workday: https://www.workday.com/

• Lenny and Friends Summit: https://lennyssummit.com/

• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k

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

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

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

• Jira: https://www.atlassian.com/software/jira

• Ashby: https://www.ashbyhq.com/

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• 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

• Charlie Munger quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome

• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

• Metromile: https://www.metromile.com/

• Tom Kennedy on LinkedIn: https://www.linkedin.com/in/tom-kennedy-37356b2b/

• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg

• Wiz: https://www.wiz.io

• Colin Powell’s 40-70 rule: https://www.42courses.com/blog/home/2019/12/10/colin-powells-40-70-rule

• Detroiters on Netflix: https://www.netflix.com/title/80165019

• Glean: https://www.glean.com/

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• Listen: Five Simple Tools to Meet Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301

• Empress Falls Canyon and abseiling: https://bmac.com.au/blue-mountains-canyoning/empress-falls-canyon-and-abseiling

—

Recommended books:

• The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898

• Inspired: How to Create Products Customers Love: https://www.amazon.com/Inspired-Create-Products-Customers-Love/dp/0981690408

—

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.

Marc Benioff is the co-founder and CEO of Salesforce, the second-largest software company in the world. He started programming at age 15, selling his first program for $75, and went on to build Salesforce into a company worth more than $300 billion that also owns Slack, Tableau, Quip, and MuleSoft. Marc is known as a marketing legend, and is now leading Salesforce into the era of AI agents. In our conversation, we discuss:

• The importance of maintaining a beginner’s mind

• His approach to product launches and marketing

• Managing through tough times and layoffs

• His relationship with Steve Jobs and lessons learned

• Why Salesforce is betting big on AI agents

• Many stories from his entrepreneurial roller coaster

• Much more

—

Brought to you by:

• Cloudinary—The foundational technology for all images and video on the internet

• Enterpret—Transform customer feedback into product growth

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

—

Where to find Marc Benioff:

• X: https://x.com/benioff

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

—

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 Marc Benioff and Salesforce

(03:54) Marc’s early career and domain names

(05:59) The App Store story and lessons from Steve Jobs

(15:18) Lessons from launching Salesforce

(22:03) The importance of keeping a beginner’s mindset

(29:53) Why Marc calls Salesforce the “25-year startup”

(31:47) Agentforce

(36:09) Why Marc says AI is the defining technology of our lifetime

(40:12) AI’s impact on the workforce

(42:31) Entrepreneurs need to be like conductors

(46:02) Failure corner

(50:32) The future of AI agents

(56:34) Final thoughts and farewell

—

Referenced:

• Bill.com: https://www.bill.com

• App Store: https://www.apple.com/app-store/

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

• Oracle: https://www.oracle.com

• Larry Ellison on X: https://x.com/larryellison

• Siebel Systems: https://en.wikipedia.org/wiki/Siebel_Systems

• Saba Software: https://talentedlearning.com/lms-vendor-directory/saba-software

• Tom Siebel on LinkedIn: https://www.linkedin.com/in/thomassiebel

• Avon: https://www.avon.com

• Salesforce Chief Has Pulled Some Crazy Stunts: https://www.businessinsider.com/marc-benioff-salesforcecom-chief-has-pulled-some-crazy-stunts-2012-3

•  Matthew McConaughey on Instagram: https://www.instagram.com/officiallymcconaughey

• Woody Harrelson on Instagram: https://www.instagram.com/woodyharrelson

• “Ask More of AI” with Matthew McConaughey: https://www.youtube.com/playlist?list=PLnobS_RgN7JaxOsLD8WH0I9E6osK3UrfI

• Marc’s tweet about the ad with McConaughey and Harrelson: https://x.com/Benioff/status/1866175950062239784

• Chris Rock on Instagram: https://www.instagram.com/chrisrock

• Sushi Iwa: http://www.sushiiwa.jp/en/

• Ryoanji Temple Rock Garden: https://www.japan.travel/en/spot/1145/

• Neil Young Archives on Instagram: https://www.instagram.com/neilyoungarchives

• Mount Tam: https://en.wikipedia.org/wiki/Mount_Tamalpais

• Spirit Rock: https://www.spiritrock.org

• Jack Kornfield: https://www.spiritrock.org/teachers/jack-kornfield

• Agentforce: https://www.salesforce.com/form/agentforce/demo

• Minority Report on Prime: https://www.amazon.com/Minority-Report-Tom-Cruise/dp/B00A2FSSHK

• Peter Schwartz on X: https://x.com/peterschwartz2

• UCSF Health: https://www.ucsfhealth.org

• A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

• Does AI improve doctors’ diagnoses? Study puts it to the test: https://www.sciencedaily.com/releases/2024/11/241113123419.htm

• A.I. Will Transform the Global Economy—if Humans Let It: https://www.nytimes.com/2024/12/07/special-series/ai-transform-global-economy.html

• Wargames on Prime: https://www.amazon.com/Wargames-Dabney-Coleman/dp/B0011EQBOS

• Her on Prime: https://www.amazon.com/Her-Joaquin-Phoenix/dp/B00KATY250

• AI (Einstein) at Salesforce: https://www.salesforce.com/in/artificial-intelligence

• Salesforce Signs Definitive Agreement to Acquire Airkit.ai: https://www.salesforce.com/news/stories/salesforce-signs-definitive-agreement-to-acquire-airkit-ai

• Salesforce Buys Big Data Startup RelateIQ for Up to $390M: https://techcrunch.com/2014/07/11/salesforce-buys-big-data-startup-relateiq-for-up-to-390m

• Salesforce to cut workforce by 10% after hiring ‘too many people’ during the pandemic: https://techcrunch.com/2023/01/04/salesforce-to-cut-workforce-by-10-after-hiring-too-many-people-during-the-pandemic

• Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell

• Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor

• Akio Toyoda: https://en.wikipedia.org/wiki/Akio_Toyoda

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

• TRS-80: https://en.wikipedia.org/wiki/TRS-80

• CLOAD Magazine: https://archive.org/details/cload_newsletter

—

Recommended books:

• Ghost Fleet: A Novel of the Next World War: https://www.amazon.com/Ghost-Fleet-Novel-Next-World/dp/054470505X

• Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company—and Revolutionized an Industry: https://www.amazon.com/Behind-Cloud-Salesforce-com-Billion-Dollar-Company/dp/0470521163

• Trailblazer: The Power of Business as the Greatest Platform for Change: https://www.amazon.com/Trailblazer-Business-Greatest-Platform-Change/dp/1984825194

—

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.

Farhan Thawar is the head of engineering at Shopify, where he oversees more than 1,000 engineers and a platform that powers over 10% of all U.S. e-commerce. Before Shopify, he was VP of engineering at Pivotal Labs and Xtreme Labs, and co-founder of Helpful.com. In our conversation, Farhan shares:

• Why choosing the harder path leads to better outcomes

• How to create intensity within your org (without burnout)

• Why every company should be embracing pair programming

• How he hires without interviewing

• How he built the world’s largest internship program

• His mission to create a “crafter’s paradise” for engineers

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Persona—A global leader in digital identity verification

• Vanta—Automate compliance. Simplify security

—

Find the transcript at: https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawer

—

Where to find Farhan Thawar:

• X: https://x.com/fnthawar

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

—

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) Farhan’s background

(05:38) Choosing the hard path

(09:37) Getting comfortable with looking dumb

(13:20) Lessons from working with visionaries

(19:19) Creating intensity in organizations

(22:06) The power of pair programming

(29:18) Shopify’s culture of intensity

(37:18) Meeting Armageddon: revolutionizing company meetings

(39:46) Reducing distractions

(41:10) Deleting 1M+ lines of code

(49:05) Three buckets of building

(57:45) Remote work and trust battery

(01:00:29) Finding stability in uncomfortable times

(01:03:14) Hiring philosophy

(01:11:41) Internship programs and co-op systems

(01:15:32) Lessons from managing 120 direct reports

(01:20:40) Failure corner

(01:27:46) Lightning round and closing thoughts

—

Referenced:

• The Steve Jobs quote about connecting dots: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only

• Shopify: https://www.shopify.com/

• GitHub: https://github.com/

• Farhan’s “questions to ask” framework: https://x.com/fnthawar/status/1514193402828574721

• Palantir: https://www.palantir.com/

• Joe Liemandt: https://www.linkedin.com/in/liemandt

• Chamath Palihapitya: https://en.wikipedia.org/wiki/Chamath_Palihapitiya

• Xtreme Labs: https://www.xtremelabs.io

• Parkinson’s law: https://www.verywellmind.com/what-is-parkinsons-law-6674423

• Pair programming: https://dev.to/documatic/pair-programming-best-practices-and-tools-154j

• Cody Fauser on LinkedIn: https://www.linkedin.com/in/codyfauser

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

• Chaos Monkey: We look at Shopify’s new ‘culture of focus’: https://www.siliconrepublic.com/careers/shopify-chaos-monkey-meetings-culture-deann-evans

• Empowering devs with AI: How Shopify made GitHub Copilot core to its culture: https://www.youtube.com/watch?v=wVKBwcm5dbw&t=2318s

• Tobi Lütke of Shopify: Powering a Team with a ‘Trust Battery’: https://www.nytimes.com/2016/04/24/business/tobi-lutke-of-shopify-powering-a-team-with-a-trust-battery.html

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Stop Being Deceived by Interviews When You’re Hiring: https://www.forbes.com/sites/forbesleadershipforum/2012/02/07/stop-being-deceived-by-interviews-when-youre-hiring/

• Shopify’s made the Life Story a major part of their interview: https://news.ycombinator.com/item?id=39294140

• Internships at Shopify: https://internships.shopify.com

• Nick Adams on LinkedIn: https://www.linkedin.com/in/nick-adams-32b28139

• React Native: https://reactnative.dev

• Swift: https://www.swift.org

• Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview

• The Power of Performance Reviews: Use This System to Become a Better Manager: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager

• Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev

• The Secret to a Great Planning Process—Lessons from Airbnb and Eventbrite: https://review.firstround.com/the-secret-to-a-great-planning-process-lessons-from-airbnb-and-eventbrite

• How to do great work: https://www.paulgraham.com/greatwork.html

• Challengers on Prime: https://www.amazon.com/Challengers-Luca-Guadagnino/dp/B0CX5MZ9M4

• Halt and Catch Fire on Prime: https://www.amazon.com/Halt-Catch-Fire-Season-1/dp/B0CKXZNT96

• Meta Ray-Bans: https://www.meta.com/smart-glasses/shop-all

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

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Recommended books:

• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/Undoing-Project-Friendship-Changed-Minds/dp/0393254593

• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• Manna: Two Visions of Humanity’s Future: https://www.amazon.com/Manna-Two-Visions-Humanitys-Future-ebook/dp/B007HQH67U

• Business Adventures: Twelve Classic Tales from the World of Wall Street: https://www.amazon.com/Business-Adventures-Twelve-Classic-Street/dp/1504000021

—

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.

Jackson Shuttleworth is a Group PM at Duolingo, where he leads the retention team and the powerful streak feature. The streak feature, which gamifies consecutive days of learning, has been Duolingo’s most important and innovative growth lever and a key driver of their growth to a $14 billion business with almost 600 million users. In our conversation, we dive deep into the history and lessons of this feature:

• The evolution of the streak feature

• Biggest insights from over 600 streak-related experiments

• Biggest specific wins and misses along the way

• Key principles for building effective streak mechanics

• How to operate a high-velocity product team

• Tips for building engaging notification systems

• Much more

—

Brought to you by:

• Pendo—The only all-in-one product experience platform for any type of application

• Vanta—Automate compliance. Simplify security

• Coda—The all-in-one collaborative workspace

—

Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-duolingo-streaks

—

Where to find Jackson Shuttleworth:• LinkedIn: https://www.linkedin.com/in/jackson-shuttleworth/

—

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) Jackson’s background and an overview of Duolingo’s streak feature

(06:00) The impact of streaks on Duolingo’s success

(09:58) The origin and evolution of streaks

(14:50) Key experiments and insights

(24:38) User psychology and engagement strategies

(28:36) Duolingo’s product review structure

(33:07) Designing for clarity and adaptability

(46:59) Developing the Streak Freeze feature

(50:47) Balancing monetization and retention

(54:08) Notification strategies

(58:15) The Perfect Streak feature

(01:00:40) Enhancing the user experience 

(01:04:47) Team operations and experimentation

(01:18:57) Who can benefit from streaks

(01:21:00) Lightning round

—

Referenced:

• Duolingo streaks: https://duolingo.fandom.com/wiki/Streak

• How to make learning as addictive as social media: https://www.ted.com/talks/luis_von_ahn_how_to_make_learning_as_addictive_as_social_media?subtitle=en

• Luis von Ahn on LinkedIn: https://www.linkedin.com/in/luis-von-ahn-duolingo/

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

• Royal Match: https://www.dreamgames.com/games/royal-match

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• You’re on fire! Or, how we brought the streak milestone to life: https://blog.duolingo.com/streak-milestone-design-animation/

• Duolingo Doubles Down on Design and Animation with Acquisition of Hobbes: https://investors.duolingo.com/news-releases/news-release-details/duolingo-doubles-down-design-and-animation-acquisition-hobbes

• Hobbes: https://www.hobbes.work/

• Jira: https://www.atlassian.com/software/jira

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

• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon/

• Peloton: https://www.onepeloton.com/

• Bluey on Disney+: https://www.disneyplus.com/series/bluey/1xy9TAOQ0M3r

• Emily in Paris on Netflix: https://www.netflix.com/title/81037371

• Multi-position ladders at Home Depot: https://www.homedepot.com/b/Building-Materials-Ladders-Multi-Position-Ladders/N-5yc1vZasew

—

Recommended books:

• A Guide to Midwestern Conversation: https://www.amazon.com/Guide-Midwestern-Conversation-Taylor-Phillips/dp/1984861336

• Fate Is the Hunter: A Pilot’s Memoir: https://www.amazon.com/Fate-Hunter-Ernest-K-Gann/dp/0671636030

—

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.

Seth Godin is a legend. He’s a marketer, teacher, entrepreneur, and author of more than 20 books, including Purple Cow, Permission Marketing, and Linchpin. He also writes one of the most popular and longest-running blogs in the world (approaching publishing 10,000 in a row!) and continues to shape how we think about marketing, brand, product, and creating lasting change in the world. In our conversation, we discuss:

• How to build remarkable products that spread

• The four critical strategic choices that determine your future

• How to develop good taste and high standards

• The role of tension in great strategy

• How Seth used Claude to write his newest book

• Much more

—

Brought to you by:

• DX—A platform for measuring and improving developer productivity

• Vanta—Automate compliance. Simplify security

• Paragon—Ship every SaaS integration your customers want

—

Find the transcript at: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

—

Where to find Seth Godin:

• Blog: http://seths.blog/

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

• Website: https://www.sethgodin.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) Seth’s background

(05:17) Understanding good taste and upholding high standards

(08:09) Become the best at whatever you do

(09:48) Seth’s journey as a product manager

(14:09) What people often get wrong when building products

(16:00) Building a brand in the age of AI

(19:04) Using AI to enhance writing

(22:40) Four critical elements for an effective strategy

(27:38) The role of tension in strategy

(29:15) The concept of the purple cow

(33:11) "Safe is risky"