Nikhyl Singhal is the founder of The Skip, a community for senior product leaders; a former product exec at Meta, Google, and Credit Karma; and a many-time founder. He’s also one of the most honest, unfiltered voices on what’s actually happening in product management right now.

In our in-depth conversation, we discuss:

1. Why the next two years will be the most chaotic period in product management history

2. Why half of current product managers are at risk, and what separates those who’ll do well

3. Why you need to find your “moments of joy” with AI

4. The “smiling exhaustion” he’s seeing across the product community

5. The psychological barriers that prevent people from reinventing themselves

6. Why your resume’s fancy logos matter less than ever, and what matters now

7. His prediction that companies will shed 30,000 people and rehire 8,000—all AI-first

—

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/why-half-of-product-managers-are-in-trouble

—

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

—

Where to find Nikhyl Singhal:

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

• X: https://x.com/nikhyl

• Podcast & Newsletter: https://skip.show

• Skip Community: https://skip.community

• Skip Coach: https://skip.coach

• Skip.help: https://skip.help

—

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 Nikhyl Singhal

(02:25) The big picture: what’s changing for product managers

(10:00) Are product leaders doing better than 2-3 years ago?

(11:44) What will change in the next couple of years

(14:23) How companies are changing the way they build products

(15:51) What “judgment” really means for PMs

(17:46) Why there won’t be any more bad software

(20:25) The skills you need to be effective today

(23:31) Why there are more PM roles than ever

(24:27) The builder versus information-mover divide

(30:14) The non-builder problem

(30:53) Should PMs code?

(34:15) Why experienced leaders still matter

(35:44) The diversity setback nobody’s talking about

(37:21) Why your brand doesn’t matter as much anymore

(39:54) How valued skills are flipping upside down

(40:49) Why change is so hard for humans

(43:53) The “equal disappointment” algorithm

(46:39) You must cross the threshold

(48:37) This chaos will settle

(53:19) Finding your moment of joy

(58:50) Nikhyl’s AI stack and what he’s building

(1:00:53) The obsolescence mindset

(1:05:24) Specific advice for PMs right now

(1:08:58) The four jobs that will exist in the future

(1:11:59) Why alignment is changing (but not disappearing)

(1:15:40) How engineering is changing even more than PM

(1:17:04) The surprising design plateau

(1:18:49) Finding optimism in the chaos

(1:21:12) Lightning round

—

Referenced:

• Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career

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

• United Airlines: https://www.united.com

• State of the product job market in early 2026: https://www.lennysnewsletter.com/p/state-of-the-product-job-market-in-ee9

• Head of Growth (Anthropic): “Claude is growing itself at this point” | Amol Avasare: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run

• Demis Hassabis on X: https://x.com/demishassabis

• Sam Altman on X: https://x.com/sama

• Dario Amodei on X: https://x.com/DarioAmodei

• Cross on Prime Video: https://www.amazon.com/Cross-Season-1/dp/B0D6X7ZZHC

• Jack Ryan on Prime Video: https://www.amazon.com/Tom-Clancys-Jack-Ryan/dp/B0CNDCMN8R

• 24 on Prime Video: https://www.amazon.com/24-Season-1/dp/B000HPF85A

• Claude Code: https://code.claude.com

• Codex: https://chatgpt.com/codex

• Lovable: https://lovable.dev

• Sonos: https://www.sonos.com

• “There are only four jobs” on X: https://x.com/yrechtman/status/2039012253341495462

• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f

• Lioness on Paramount+: https://www.paramountplus.com/shows/lioness

• Tesla: https://www.tesla.com

• Albert Einstein’s quote: https://www.goodreads.com/quotes/115696-genius-is-1-talent-and-99-percent-hard-work

—

Recommended books:

• James: https://www.amazon.com/James-Novel-Percival-Everett/dp/0385550367

• The Adventures of Huckleberry Finn: https://www.amazon.com/Adventures-Huckleberry-Finn-Unabridged-Uncensored/dp/195483943X

—

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

—

Lenny may be an investor in the companies discussed.

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).

In our in-depth conversation, Keith shares:

1. The barrels vs. ammunition hiring framework (and how to spot barrels)

2. Why talking to customers is actively harmful for consumer products

3. How to identify undiscovered talent

4. Why the PM role is dying

5. The three traits of the best-performing companies right now

6. The specific interview question he asks every senior candidate

7. Why CMOs (not engineers) are becoming the #1 consumer of tokens

—

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/hard-truths-about-building-in-the-ai-era

—

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

—

Where to find Keith Rabois:

• X: https://x.com/rabois

• LinkedIn: linkedin.com/in/keith

• Website: https://www.khoslaventures.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 Keith Rabois

(01:59) Why Keith hasn’t used a computer since 2010

(04:52) The team you build is the company you build

(07:40) How Keith learned to identify talent at PayPal

(10:05) Tactics for getting better at hiring

(15:31) The barrels vs. ammunition framework

(18:52) What makes someone a barrel

(22:36) How to attract the best talent

(26:18) Building companies on undiscovered talent

(27:53) Why better performance requires more pressure

(32:36) Career advice in the age of AI

(35:14) The future of the product triad

(41:03) Why design and code are merging

(49:35) What practicing law taught Keith about entrepreneurship

(51:22) Contrarian takes on customer feedback

(1:02:33) Identifying great AI opportunities

(1:05:13) Advice for evaluating statrups 

(1:12:36) Criticizing in public vs. private

(1:15:05) Failure corner

(1:17:29) Lightning round

—

Referenced:

• Square: https://squareup.com

• Jack Dorsey on X: https://x.com/jack

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

• Simon Willison’s Weblog: https://simonwillison.net

• Vinod Khosla on X: https://x.com/vkhosla

• Peter Thiel on X: https://x.com/peterthiel

• Max Levchin on X: https://x.com/mlevchin

• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks

• Tony Xu on X: https://x.com/t_xu

• David Sze on X: https://x.com/davidsze

• Faire: https://www.faire.com

• Max Rhodes on X: https://x.com/MaxRhodesOK

• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson

• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois

• Lattice: https://lattice.com

• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640

• 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 art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights

• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs)

• Eric Glyman on X: https://x.com/eglyman

• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177

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

• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html

• Opendoor: https://www.opendoor.com

• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q

• Lovable: https://lovable.dev

• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code

• 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

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

• Jeremy Stoppelman on X: https://x.com/jeremys

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol

• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms

• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway

• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare

• Evan Moore on X: https://x.com/evancharles

• Andrew Mason on X: https://x.com/andrewmason

• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941

• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16

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

• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden

• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred

• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000

• Jon Chu on X: https://x.com/jonchu

• Kanu Gulati on X: https://x.com/KanuGulati

• Rogo: https://rogo.ai

• Profound: https://www.tryprofound.com

• Basis: https://www.getbasis.ai

• Spellbook: https://www.spellbook.legal

• Roelof Botha on X: https://x.com/roelofbotha

• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742

• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4

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

• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224

—

Recommended books:

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012

• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666

• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934

—

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.

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year.

In our in-depth discussion, Amol shares:

1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger

2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”)

3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive

4. Why activation is the single highest-leverage growth problem in AI

5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams)

6. How he uses Cowork to detect team misalignment in Slack

7. How the company’s focus on AI coding created a research flywheel that accelerated their models

—

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/anthropics-1b-to-19b-growth-run

—

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

—

Where to find Amol Avasare:

• X: https://x.com/TheAmolAvasare

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

—

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 Amol and Anthropic’s growth

(03:15) The story of cold emailing Mike Krieger to get the job

(08:28) What it’s like leading growth at the fastest-growing company ever

(10:46) What the growth team actually does at Anthropic

(12:16) The concept of “success disasters”

(13:55) Why activation is the biggest challenge in AI products

(18:05) Improving Mercury’s onboarding experience

(20:57) The importance of adding the right kind of friction

(25:10) Anthropic’s org structure

(27:06) Why Anthropic focuses on big bets over micro-optimizations

(33:34) Automating growth experiments with Claude (CASH)

(38:20) How AI is starting to identify what experiments to run

(41:07) The future of PM, engineering, and design roles

(47:19) Why you might need more PMs as engineers get more productive

(51:13) How Amol uses AI to prototype ideas and skip PRDs

(58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically

(1:03:31) Getting coaching from an AI version of your manager

(1:06:27) How Anthropic’s focus on coding and B2B drove their success

(1:12:10) Balancing growth with AI safety as a core mission

(1:18:09) Advice for thriving in an AI-first future

(1:22:53) Anthropic’s culture and the “notebook channels” on Slack

(1:35:12) Failure corner: Shutting down his startup after raising money

(1:38:25) The traumatic brain injury that changed everything

(1:46:49) Lightning round

—

References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run

—

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.

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:

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

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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

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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.