Lenny's Podcast: Product | Career | Growth

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
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to 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
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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
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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
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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.


To hear more, visit www.lennysnewsletter.com

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
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
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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].


To hear more, visit www.lennysnewsletter.com

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
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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
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
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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
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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.


To hear more, visit www.lennysnewsletter.com

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.
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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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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
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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.


To hear more, visit www.lennysnewsletter.com

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
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
—
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.


To hear more, visit www.lennysnewsletter.com