Lenny's Podcast: Product | Career | Growth

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
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Where to find Keith Rabois:
• X: https://x.com/rabois
• LinkedIn: linkedin.com/in/keith
• Website: https://www.khoslaventures.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 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
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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
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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
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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

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
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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 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
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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.


To hear more, visit www.lennysnewsletter.com

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
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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 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
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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.


To hear more, visit www.lennysnewsletter.com

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
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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 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
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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
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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.


To hear more, visit www.lennysnewsletter.com

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)
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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
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com