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:

Omni—AI analytics your customers can trust

Vanta—Automate compliance. Simplify security.

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.

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents.

We discuss:

1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes

2. How AI is changing the role of managers

3. Why the productivity gap between AI power users and everyone else is widening

4. Why “models will eat your scaffolding for breakfast”

5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Sentry—Code breaks, fix it faster

Datadog—Now home to Eppo, the leading experimentation and feature flagging platform

—

Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers

—

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

—

Where to find Sherwin Wu:

• X: https://x.com/sherwinwu

• LinkedIn: https://www.linkedin.com/in/sherwinwu1

—

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 Sherwin Wu

(03:10) AI’s role in coding at OpenAI

(06:53) The future of software engineering with AI

(12:26) The stress of managing agents

(15:07) Codex and code review automation

(19:29) The changing role of engineering managers

(24:14) The one-person billion-dollar startup

(31:40) Management lessons

(37:28) Challenges and best practices in AI deployment

(43:56) Hot takes on AI and customer feedback

(48:57) Building for future AI capabilities

(50:16) Where models are headed in the next 18 months

(53:35) Business process automation

(57:22) OpenAI’s ecosystem and platform strategy

(01:00:50) OpenAI’s mission and global impact

(01:05:21) Building on OpenAI’s API and tools

(01:08:16) Lightning round and final thoughts

—

Referenced:

• Codex: https://openai.com/codex

• 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

• OpenClaw: https://openclaw.ai

• The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code

• The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas)

• Quora: https://www.quora.com

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

• Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar

• Sam Altman on X: https://x.com/sama

• Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957

• The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html

• Overton window: https://en.wikipedia.org/wiki/Overton_window

• Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt

• Responses: https://platform.openai.com/docs/api-reference/responses

• Agents SDK: https://platform.openai.com/docs/guides/agents-sdk

• AgentKit: https://openai.com/index/introducing-agentkit

• Ubiquiti: https://ui.com

• Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB

• eero: https://eero.com

• Opendoor: https://www.opendoor.com

—

Recommended books:

• Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871

• The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959

• There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750

• Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034

• Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373

—

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.

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI.

We discuss:

1. Why having no coding background can be an advantage when building with AI

2. Why most of your time should go to planning and chat mode, not prompting

3. What to do when you get stuck: his 4x4 debugging workflow

4. The PRD and Markdown file system that keeps AI agents aligned across complex builds

5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking

6. Why design skills and taste are going to be the most important skills in the future

7. His “genie and three wishes” mental model for making the most of AI’s limitations

8. How product, engineering, and design roles are converging—and what that means for your career

—

Brought to you by:

Strella—The AI-powered customer research platform: https://strella.io/lenny

Samsara—Saving lives with AI built for physical operations: https://samsara.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/getting-paid-to-vibe-code

—

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

—

Where to find Lazar Jovanovic:

• X: https://x.com/lakikentaki

• LinkedIn: https://www.linkedin.com/in/lazar-jovanovic

• YouTube: https://www.youtube.com/@50in50challenge

• Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off)

—

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 Lazar and professional vibe coding

(04:53) What a professional vibe coder actually does day-to-day

(09:26) Why non-technical backgrounds can be an advantage

(12:24) The importance of self-awareness

(14:42) His “genie and three wishes” mental model

(17:43) Developing taste and judgment in the age of AI

(21:46) The parallel project approach for better outcomes

(29:30) Creating dynamic context windows with PRDs

(36:56) Why elite vibe coders focus on planning, not coding

(44:43) Creating MD files to guide AI development

(50:57) Why prototyping still matters

(56:50) Why “good enough” is no longer good enough

(01:00:53) The future of engineering in an AI world

(01:05:14) What to do when you get stuck: his 4x4 debugging workflow

(01:14:27) Helping agents learn from their mistakes

(01:15:35) Why watching agent output is more important than code

(01:19:08) The incredible pace of AI development

(01:22:55) Why emotional intelligence will become more valuable

(01:28:30) How to become a professional vibe coder

(01:30:10) Why building in public is the fastest path to opportunities

(01:37:03) Final thoughts on focusing on quality over tech stack

—

Referenced:

• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• 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

• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna

• Lovable: https://lovable.dev

• Lovable + Shopify: https://lovable.dev/shopify

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Mobbin: https://mobbin.com

• Dribbble: https://dribbble.com

• 21st.dev: https://21st.dev

• Lovable base prompt generator: https://chatgpt.com/g/g-67e1da2c9c988191b52b61084438e8ee-lovable-base-prompt

• Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator

• Felix Haas’s newsletter: https://designplusai.com

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

• Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism

• UI style guide: http://uistyle.lovable.app

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

• Ben Tossell on X: https://x.com/bentossell

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4

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

• The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen

• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

• Slumdog Millionaire: https://www.imdb.com/title/tt1010048

—

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.

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship.

We discuss:

1. Why repair—not perfection—defines strong leadership

2. Why you need to connect before you correct to build cooperation and trust

3. The “most generous interpretation” framework for handling difficult behaviors

4. How to correctly set boundaries (vs. making requests)

5. The power of “I believe you, and I believe in you”

6. What it looks like to be a “sturdy” leader

—

Brought to you by:

Merge—Fast, secure integrations for your products and agents: https://merge.dev/lenny

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

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

—

Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap

—

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

—

Where to find Dr. Becky Kennedy:

• X: https://x.com/GoodInside

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

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

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

• Website: https://www.goodinside.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 Dr. Becky Kennedy

(05:14) Connecting parenting and leadership

(08:40) The power of repair

(11:05) Connecting before correcting

(17:45) Good Inside framework at work

(22:08) The most generous interpretation (MGI)

(25:46) Curiosity over judgment

(27:07) Understanding behavior change

(31:08) What potty training can teach us about workplace behavior

(34:40) Naming your intention

(35:41) Sturdy leadership

(40:52) How to set boundaries well

(46:33) The role of leadership and consensus

(50:50) The importance of being “locatable”

(52:40) A powerful story of betrayal and realization

(57:12) Building resilience over happiness

(01:00:34) The power of the phrase “I believe you, and I believe in you.”

(01:09:08) The Good Inside community and resources

(01:16:22) AI corner

(01:19:52) Good Inside’s mission

(01:22:26) Lightning round and final thoughts

—

Referenced:

• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi

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

• From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng

• Punch: https://en.wikipedia.org/wiki/Punch_(play)

• Figma: https://www.figma.com

• Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan

• Replit: https://replit.com

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

• Lovable: https://lovable.dev

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Claude: https://claude.ai

• ChatGPT: https://chatgpt.com

• Secrets We Keep on Netflix: https://www.netflix.com/title/81697668

• K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621

• Liberty puzzles: https://libertypuzzles.com

—

Recommended books:

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

• Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481

• Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117

• The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/

• The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072

• 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

—

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.