Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net.

In our in-depth conversation, Simon shares:

1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works”

2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m.

3. Why mid-career engineers (not juniors) are most at risk right now

4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding)

5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA

6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster

7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality

—

Brought to you by:

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

Vanta—automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Simon Willison:

• X: https://x.com/simonw

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

• Website: https://simonwillison.net

• Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns

—

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 Simon Willison

(02:40) The November 2025 inflection point

(08:01) What’s possible now with AI coding

(10:42) Vibe coding vs. agentic engineering

(13:57) The dark-factory pattern

(20:41) Where bottlenecks have shifted

(23:36) Where human brains will continue to be valuable

(25:32) Defending of software engineers

(29:12) Why experienced engineers get better results

(30:48) Advice for avoiding the permanent underclass

(33:52) Leaning into AI to amplify your skills

(35:12) Why Simon says he’s working harder than ever

(37:23) The market for pre-2022 human-written code

(40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026

(44:34) The impact of cheap code

(48:27) Simon’s AI stack

(54:08) Using AI for research

(55:12) The pelican-riding-a-bicycle benchmark

(59:01) The inherent ridiculousness of AI

(1:00:52) Hoarding things you know how to do

(1:08:21) Red/green TDD pattern for better AI code

(1:14:43) Starting projects with good templates

(1:16:31) The lethal trifecta and prompt injection

(1:21:53) Why 97% effectiveness is a failing grade

(1:25:19) The normalization of deviance

(1:28:32) OpenClaw: the security nightmare everyone is looking past

(1:34:22) What’s next for Simon

(1:36:47) Zero-deliverable consulting

(1:38:05) Good news about Kakapo parrots

—

References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union

—

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

—

Lenny may be an investor in the companies discussed.

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life.

We discuss:

1. The exact step-by-step process to install and set up OpenClaw (it’s easier than you think)

2. How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer)

3. Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management)

4. Why multiple specialized agents beat one general-purpose agent

5. The security risks everyone worries about—and how to handle them

6. Browser limitations, memory issues, and practical workarounds

—

Brought to you by:

Mercury—Radically different banking

Omni—AI analytics your customers can trust

Orkes—The enterprise platform for reliable applications and agentic workflows

—

Where to find Claire Vo:

• X: https://x.com/clairevo

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

• Podcast: https://www.youtube.com/@howiaipodcast

• Website: https://clairevo.com

• ChatPRD: https://www.chatprd.ai

—

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 Claire and OpenClaw

(08:00) The journey from OpenClaw skeptic to believer

(11:50) What OpenClaw actually does that’s useful

(13:35) OpenClaw vs. other AI agent products

(17:05) How to actually install OpenClaw: the basics

(18:49) Setting up like you’d onboard a real assistant

(20:41) Security and privacy considerations

(24:53) Live demo: Installing OpenClaw step-by-step

(28:47) Setting up Q: an agent for her kids’ homework

(34:08) Understanding “soul,” “identity,” and “memory”

(40:40) The unlock: multiple agents, not just one

(45:02) How to run multiple agents on one machine

(47:28) Jesse Genet’s homeschooling use case

(49:58) Real examples and use cases

(56:41) Finn, Claire’s family agent

(1:00:05) Sage the Course Bot

(1:02:15) Common issues and workarounds

(1:08:08) The Exa/Perplexity web search workaround

(1:09:29) Memory management and context overload

(1:12:09) Pro tip: Screen sharing to manage Mac Minis

(1:14:18) Using Google Workspace for agent collaboration

(1:16:24) What makes OpenClaw special

(1:20:15) The “yappers API” and ramble mode

(1:22:04) Using Claude Code as your OpenClaw brain surgeon

(1:25:16) Bringing management skills to AI agents

(1:29:32) Why this matters

(1:32:37) Lightning round and final thoughts

—

Referenced:

• OpenClaw: https://openclaw.ai

• Claude Cowork: https://claude.com/product/cowork

• Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics

• Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete

• Telegram: https://telegram.org

• WhatsApp: https://www.whatsapp.com

• Fin: https://fin.ai

• Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175

• 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk

• Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org

• Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/

• ChatGPT Atlas: https://chatgpt.com/atlas

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

• Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser

• Buffer: https://buffer.com

• Brave: https://brave.com/search/api/

• Exa: https://exa.ai

• Hilary Gridley on X: https://x.com/yourgirlhils

• How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with

• How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI

• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang

• How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

• Age of Attraction on Netflix: https://www.netflix.com/title/81779095

• Oura Ring: https://ouraring.com/

• Eight Sleep: https://www.eightsleep.com

• Hoopsalytics: https://hoopsalytics.com

• DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp

• Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

—

Recommended books:

• Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400

• Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X

• Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

—

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

—

Lenny may be an investor in the companies discussed.

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.

We discuss:

1. Why great ideas often don’t get buy-in

2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much

3. Why executives are usually optimizing for a global maximum while you are often optimizing locally

4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”

5. Why you should go in to learn, not to convince

6. Why showing only one option is a mistake

7. Why AI will make influence more important, not less

—

Brought to you by:

Omni—AI analytics your customers can trust

Lovable—Build apps by simply chatting with AI

Vanta—Automate compliance, manage risk, and accelerate trust with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Jessica Fain:

• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989

—

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 Jessica Fain

(03:53) Why influence is the highest-leverage skill in product

(04:47) Why great ideas fail without executive buy-in

(06:00) How executives actually think

(09:05) The fundamentals: context-setting, communication, and empathy

(10:22) Stop pitching for approval—start co-creating with execs

(12:59) Influence vs. politics (and why people get it wrong)

(15:44) How to disagree with execs without losing trust

(17:20) Going in to learn, not to convince

(19:08) How to present ideas

(26:05) The Minto-style approach and tailoring your communication to each exec

(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”

(30:24) Understanding incentives to unlock buy-in

(32:10) Aligning product work with company strategy

(35:10) Quick summary

(37:31) Disarming the executive

(40:49) Speed matters: why fast follow-up builds momentum

(43:32) How to run high-impact meetings (the 60-second rule)

(47:00) Why influencing execs is part of your job

(49:15) Asking for more resources and thinking in 10x bets

(52:23) What to do when your idea gets rejected

(54:18) Clarifying information

(56:50) How to build trust and make ideas stick

(58:30) Shrinking big ideas into experiments

(01:02:27) Common mistakes people make when influencing leaders

(01:06:00) How to grow into your next role

(01:09:32) How AI is changing influence and product work

(01:17:55) Using AI to simulate exec feedback and improve pitches

(01:21:15) Protecting our brains from overwhelm

(01:22:44) Lightning round and final thoughts

—

Referenced:

• Box: https://www.box.com

• Slack: https://slack.com

• Brightwheel: https://mybrightwheel.com

• Webflow: https://webflow.com

• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood

• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua

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

• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid

• Calendly: https://calendly.com

• Glassdoor: https://www.glassdoor.co.in/index.htm

• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai

• Ethan Eismann on X: https://x.com/eeismann

• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank

• Checkr: https://checkr.com

• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl

• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan

• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief

• Barbara Minto’s website: https://www.barbaraminto.com

• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff

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

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

• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD

• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2

• Casa: https://getcasa.com

• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix

• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles)

—

Recommended books:

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

• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061

• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243

• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X

—

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

—

Lenny may be an investor in the companies discussed.

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes.

We discuss:

1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump

2. Why Jacob sees 40% average movement when negotiations are run well

3. When negotiation actually starts (hint: it’s much earlier than you think)

4. Why information + timing create power

5. The biggest mistakes people make when negotiating

6. How to navigate the important “What’s your comp expectation?” question without anchoring too low

7. Why the best interviews feel more like discovery calls than interrogations

—

Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Mercury—Radically different banking

Omni—AI analytics your customers can trust

—

Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Jacob Warwick:

• Substack: https://www.execsandthecity.com

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

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

• Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course

—

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 Jacob Warwick

(04:12) How much comp people leave on the table

(07:52) Why you shouldn’t feel greedy asking for more

(09:45) What founders should know about negotiation

(13:03) How Jacob works behind the scenes

(15:35) The biggest mistakes people make when negotiating

(19:30) Home-field advantage and controlling the conversation

(23:02) The step-by-step approach to negotiating an offer

(30:17) Jacob’s passion and why these tips don’t work on kids

(32:04) Who should speak first about compensation

(35:36) Understanding power

(39:52) Breaking out of salary bands by focusing on pain points

(45:45) Brief summary

(47:20) Selling the vacation: How to visualize success

(50:07) Controlling the narrative and planting seeds

(59:01) Jacob’s role as hype man

(01:01:05) Positioning yourself like a product

(01:02:49) Making the process frictionless for hiring managers

(01:06:20) Flipping the interview to extract information

(01:12:17) Five tactical tips for negotiating comp

(01:21:45) What to do when negotiations fall apart

(01:25:05) Why negotiation is different for every individual

(01:28:55) Why outcomes aren’t predetermined

(01:32:52) Wild Hollywood negotiation stories

(01:37:35) The first step you should take after getting an offer

(01:40:30) Jacob’s personal mission

(01:44:42) Lightning round and final thoughts

—

Referenced:

• The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating

• Sam Altman on X: https://x.com/sama

• Tom Brady on X: https://x.com/TomBrady

• Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8

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

• Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts

• Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon

• Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that

• Chris Voss on X: https://x.com/fbinegotiator

• Werewolf: https://playwerewolf.co

• Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion

• How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy

• ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation

• Marvel: https://www.marvel.com

• Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030

• Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0

• Minuscule: https://www.youtube.com/user/Minuscule

• Claude Cowork: https://claude.com/product/cowork

• Macrofactor: https://macrofactor.com

• Whoop: https://www.whoop.com

• Gemini: https://gemini.google.com/app

• The Cody Dieruf Foundation: https://breathinisbelievin.org

• Cystic Fibrosis Foundation: https://www.cff.org

—

Recommended books:

• Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941

• Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X

• You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229

• Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325

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

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

• 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 [email protected].

—

Lenny may be an investor in the companies discussed.

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it.

We discuss:

1. The collection of moments that led me to what I do now

2. When I added a paywall, and how I knew it was working

3. The hidden treadmill behind shipping a newsletter post and podcast episode every week

4. The most stressful moments I’ve had in business and in life

5. How I think about stress, consistency, and keeping the business small

—

Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184

—

Brought to you by:

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Michelle Rial:

• X: https://x.com/TheRialMichelle

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

• Website: https://www.michellerial.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 and role reversal

(04:06) What would Lenny be doing without the newsletter?

(07:20) The moments that led to starting the newsletter

(09:58) Does Lenny still enjoy the work?

(12:42) Stress management and misophonia

(14:00) The psychedelic trip that changed everything

(15:45) Online happiness course and baseline optimization

(17:30) Thunder round: Lenny’s misophonia worst sounds

(20:20) What makes Michelle’s charts so shareable

(23:55) Where chart ideas come from (and why meditation helps)

(26:59) Where does “Lenny” come from?

(28:54) Being recognized in public

(31:24) Early projects

(36:30) Michelle and Lenny’s yin and yang

(37:49) Missing office culture (but not really)

(39:37) Lenny’s face blindness

(40:47) The $100M fraud attack story

(42:50) Michelle’s childbirth emergency

(47:22) Michelle’s creative process

(51:58) Lenny’s favorite children’s books

(54:00) Product management lessons in parenting

(55:31) Defining product management in five words

(58:23) Why Michelle pivoted to children’s books

(01:01:30) The power of iteration and real experience

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter

—

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

Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan.

We discuss:

1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software

2. Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that

3. The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed

4. The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer

5. The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early

6. How reading old books is the best way to build taste

—

Brought to you by:

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Lovable—Build apps by simply chatting with AI

—

Episode transcript: https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Qasar Younis:

• X: https://x.com/qasar

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

• Website: https://qy.co

• Reading list: https://qy.co/books

—

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 Qasar and Applied Intuition

(04:01) The optimistic vision: How AI will create abundance

(08:49) Why anxiety about AI comes from misunderstanding—and how to fight fear with knowledge

(12:58) The market sell-off explained

(16:31) Self-driving cars: Why 30,000 annual deaths prove we need autonomy now

(20:22) The spectrum of physical AI

(28:00) How AI is coming just in time

(33:26) Why comparing Chinese AI companies to American AI companies is a category error

(39:12) Why Qasar finally joined Twitter after staying silent for a decade

(45:08) Why successful companies almost always show early signs of traction

(50:40) Applied Intuition’s core values

(56:00) Why the company cleans its own office—and never spent a dollar of raised capital

(58:50) Quasar’s reading philosophy

(01:06:14) How to operationalize listening to naysayers

(01:12:53) The importance of decisiveness

(01:14:55) Removing emotions from decisions

(01:19:02) Why most Silicon Valley CEOs don’t have great taste—and how to develop it

—

Referenced:

• Applied Intuition: https://www.appliedintuition.com

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Elad Gil’s website: https://eladgil.com

• Bosch: https://www.bosch.com

• Berkshire Hathaway: https://www.berkshirehathaway.com

• Naval Ravikant on X: https://x.com/naval

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

• Waymo: https://waymo.com/

• Tesla: https://www.tesla.com

• DeepSeek: https://www.deepseek.com

• Rivian: https://rivian.com

• Crate & Barrel: https://www.crateandbarrel.com

• OpenClaw: https://openclaw.ai

• Sam Altman on X: https://x.com/sama

• Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig

• What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal

• 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger

• Andreessen Horowitz: https://a16z.com

• John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211

• Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette

• Steve Ballmer on X: https://x.com/Steven_Ballmer

• General Motors: https://www.gm.com

—

Recommended books:

• House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633

• Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one

• The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685

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

• The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916

• Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835

• My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965

• Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552

• Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009

• SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230

• A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X

—

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

Lenny may be an investor in the companies discussed.

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.

—

We discuss:

1. Why the classic discovery → mock → iterate design process is becoming obsolete

2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack

3. Whether AI will eventually surpass humans in taste and judgment

4. Why Jenny left a director role at Figma to return to IC work at Anthropic

5. The three archetypes Jenny is hiring for now

6. Why chatbot interfaces may be more durable than most people expect

—

Brought to you by:

Mercury—Radically different banking: https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaign

Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/

Omni—AI analytics your customers can trust: https://omni.co/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Jenny Wen:

• X: https://x.com/jenny_wen

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

• Substack: https://jennywen.substack.com

• Website: https://jennywen.ca

—

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 Jenny Wen

(04:23) Why the traditional design process is dead

(06:33) The two new types of design work

(10:00) How widespread this shift will be

(13:00) Day-to-day life as a designer at Anthropic

(18:45) Jenny’s AI stack

(20:03) Why Figma still matters for exploration

(22:25) Advice for working with engineers

(24:19) How to maintain craft, quality, and trust in the AI era

(27:35) Will AI ever have “taste”?

(31:38) The future of chatbot interfaces

(35:33) Moving from director back to IC

(41:00) The 10-day build of Claude Cowork

(46:06) Hiring: the three archetypes

(50:44) Advice for new and senior designers

(54:42) The value of “low leverage” tasks for managers

(57:52) Why the best teams roast each other

(01:01:45) The legibility framework

(01:07:22) Lightning round and final thoughts

—

Referenced:

• Figma: https://www.figma.com

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

• v0: https://v0.app

• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk

• Claude Cowork: https://claude.com/product/cowork

• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code

• Claude Code in Slack: https://code.claude.com/docs/en/slack

• Lex Fridman’s website: https://lexfridman.com

• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

• OpenClaw: https://openclaw.ai

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Socratica: https://www.socratica.info

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

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

• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667

• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early

• Palantir: https://www.palantir.com

• Stripe: https://stripe.com

• Linear: https://linear.app

• Notion: https://www.notion.com

• Julie Zhuo’s website: https://www.juliezhuo.com

• Sentimental Value: https://www.imdb.com/title/tt27714581

• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD

• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle

• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP

• Retro: https://retro.app

• Granola: https://www.granola.ai

—

Recommended books:

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

• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767

• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X

—

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

—

Lenny may be an investor in the companies discussed.

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li.

We discuss:

1. How Cisco went AI-first across 90,000 employees

2. His six-part framework for building great companies: timing, market, team, product, brand, distribution

3. Why he says he couldn’t have done this job without AI

4. His “right to win” strategic framework

5. His communication framework for preventing “packet loss” across an organization

6. Why he flips “praise in public, criticize in private” and does the exact opposite

7. The important communication lesson his mother taught him

—

Brought to you by:

Sentry—Code breaks, fix it faster: https://sentry.io/lenny

Framer—Build better websites faster: https://framer.com/lenny

Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Jeetu Patel:

• X: https://x.com/jpatel41

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

• Website: https://blogs.cisco.com/author/jeetupatel

—

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 and welcome

(04:15) Insights from Cisco’s Al summit

(08:45) Transforming Cisco into an Al-first company

(15:33) What Cisco actually does in the Al infrastructure stack

(19:09) The future of Al

(24:36) Raising kids in the AI era

(29:46) “Permission to play” framework

(36:50) Lessons from great CEOs

(42:02) Leading at scale

(50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule

(57:45) Surrounding yourself with good human beings

(58:35) Lessons from loss

(01:03:21) Career advice: platforms, hunger, and preparation

(01:10:21) The six-part framework for building great companies

(01:19:05) Lightning round and final thoughts

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival

—

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

Lenny may be an investor in the companies discussed.

Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work.

We discuss:

1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month

2. The counterintuitive product principles that drove Claude Code’s success

3. Why Boris believes coding is “solved”

4. The latent demand that shaped Claude Code and Cowork

5. Practical tips for getting the most out of Claude Code and Cowork

6. How underfunding teams and giving them unlimited tokens leads to better AI products

7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks

8. Three principles Boris shares with every new team member

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny

Sentry—Code breaks, fix it faster: https://sentry.io/lenny

Metaview—The AI platform for recruiting: https://metaview.ai/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Boris Cherny:

• X: https://x.com/bcherny

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

• Website: https://borischerny.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 Boris and Claude Code

(03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back)

(05:35) One year of Claude Code

(08:41) The origin story of Claude Code

(13:29) How fast AI is transforming software development

(15:01) The importance of experimentation in AI innovation

(16:17) Boris’s current coding workflow (100% AI-written)

(17:32) The next frontier

(22:24) The downside of rapid innovation 

(24:02) Principles for the Claude Code team

(26:48) Why you should give engineers unlimited tokens

(27:55) Will coding skills still matter in the future?

(32:15) The printing press analogy for AI’s impact

(36:01) Which roles will AI transform next?

(40:41) Tips for succeeding in the AI era

(44:37) Poll: Which roles are enjoying their jobs more with AI

(46:32) The principle of latent demand in product development

(51:53) How Cowork was built in just 10 days

(54:04) The three layers of AI safety at Anthropic

(59:35) Anxiety when AI agents aren’t working

(01:02:25) Boris’s Ukrainian roots

(01:03:21) Advice for building AI products

(01:08:38) Pro tips for using Claude Code effectively

(01:11:16) Thoughts on Codex

(01:12:13) Boris’s post-AGI plans

(01:14:02) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

—

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

—

Lenny may be an investor in the companies discussed.

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach.

We discuss:

1. His LOCKS framework for evaluating founders

2. Why you should build your team like the 2004 Red Sox

3. Why hiring “spicy” candidates beats consensus picks

4. Why enterprise sales will be the last white-collar job AI replaces

5. Some of my favorite “Halliganisms”

—

Brought to you by:

Sentry—Code breaks, fix it faster: http://sentry.io/lenny

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny

—

Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been

—

Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

—

Where to find Brian Halligan

• X: https://x.com/bhalligan

• LinkedIn: linkedin.com/in/brianhalligan

• Delphi: https://www.delphi.ai/bhalligan

• Podcast: https://sequoiacap.com/series/long-strange-trip

—

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 Brian Halligan

(03:56) The perpetual state of constructive dissatisfaction

(05:25) Coaching CEOs

(07:49) The art of interviewing and hiring

(11:21) Getting the most out of reference calls

(13:10) Homegrown talent vs. big company hires

(16:31) Traits of successful CEOs

(19:40) Brian’s LOCKS framework for evaluating founders

(21:34) Are great CEO’s born or made?

(23:41) Giving effective feedback

(25:54) The future of go-to-market strategies

(31:56) Understanding forward deployed engineers

(34:17) How the CEO role has evolved over the last 20 years

(38:10) Halliganisms

(01:01:18) The CEO’s role in scaling a company

(01:02:41) Lightning round and final thoughts

—

Referenced:

• Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria

• HubSpot: https://www.hubspot.com

• Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

• McKinsey & Company: https://www.mckinsey.com

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

• Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang

• Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg

• James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca

• Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392

• OpenClaw: https://openclaw.ai

• Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat

• Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159

• Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm

• 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

• Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin

• Glassdoor: https://www.glassdoor.com

• 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

• Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a

• Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia

• Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir

• Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh

• Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• The American Revolution: https://www.pbs.org/kenburns/the-american-revolution

• Delphi: https://www.delphi.ai

• Sonos: https://www.sonos.com

• Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan

• The Boston Red Sox: https://www.mlb.com/redsox

—

Recommended book:

• Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520

—

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

—

Lenny may be an investor in the companies discussed.