Lenny's Podcast: Product | Career | Growth

Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO).

We discuss:

1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly

2. How the company measures AI productivity gains across technical and non-technical teams

3. Which teams are benefiting most from AI (it’s not engineering)

4. The boring organizational change that boosted productivity even more than AI tools

5. Why code quality has almost nothing to do with product success

6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily)

7. Lessons from building Google Wave, Google+, and other failed products

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Brought to you by:

Sinch—Build messaging, email, and calling into your product: https://sinch.com/lenny

Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

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Where to find Dhanji R. Prasanna:

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

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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 Dhanji

(05:26) The AI manifesto: convincing Jack Dorsey

(07:33) Transforming into a more AI-native company

(12:05) How engineering teams work differently today

(15:24) Goose: Block’s open-source AI agent

(20:18) Measuring AI productivity gains across teams

(21:38) What Goose is and how it works

(32:15) The future of AI in engineering and productivity

(37:42) The importance of human taste

(40:10) Building vs. buying software

(44:08) How AI is changing hiring and team structure

(53:45) The importance of using AI tools yourself before deploying them

(55:13) How Goose helped solve a personal problem with receipts

(58:01) What makes Goose unique

(59:57) What Dhanji wishes he knew before becoming CTO

(01:01:49) Counterintuitive lessons in product development

(01:04:56) Why controlled chaos can be good for engineering teams

(01:08:07) Core leadership lessons

(01:13:36) Failure corner

(01:15:50) Lightning round and final thoughts

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Referenced:

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

• Block: https://block.xyz/

• Square: https://squareup.com/

• Cash App: https://cash.app/

• What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law#

• Goose: https://github.com/block/goose

• Gosling: https://github.com/block/goose-mobile

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

• Snowflake: https://www.snowflake.com/

• Claude: https://claude.ai/

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• OpenAI: https://openai.com/

• 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

• Llama: https://www.llama.com/

• Cursor: https://cursor.com/

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

• Top Gun: https://www.imdb.com/title/tt0092099/

• Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/

• Afterpay: https://github.com/afterpay

• Bitkey: https://bitkey.world/

• Proto: https://github.com/proto-at-block

• Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/

• Databricks: https://www.databricks.com/

• Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch

• Google Wave: https://en.wikipedia.org/wiki/Google_Wave

• Google Video: https://en.wikipedia.org/wiki/Google_Video

• Secret: https://en.wikipedia.org/wiki/Secret_(app)

• Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M

• Steam Deck OLED display: https://www.steamdeck.com/en/oled

• Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown

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Recommended books:

• The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119

• Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products.

We discuss:

1. What people think makes AI apps better vs. what actually makes AI apps better

2. What pre-training vs. post-training is, and why fine-tuning should be your last resort

3. How RLHF (reinforcement learning from human feedback) actually works

4. Why data quality matters more than which vector database you choose

5. Why high performers are seeing the most gains from AI coding tools

6. Why most AI problems are actually UX issues

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Brought to you by:

Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/

Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

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Where to find Chip Huyen:

• X: https://x.com/chipro

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

• Website: https://huyenchip.com/

• Substack: https://substack.com/@chiphuyen

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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 Chip Huyen

(04:28) Chip’s viral LinkedIn post

(07:05) Understanding AI training: pre-training vs. post-training

(08:50) Language modeling explained

(13:55) The importance of post-training

(15:20) Reinforcement learning and human feedback

(22:23) The importance of evals in AI development

(31:55) Retrieval augmented generation (RAG) explained

(38:50) Challenges in AI tool adoption

(43:19) Challenges in measuring productivity

(45:20) The three-bucket test

(49:10) The future of engineering roles

(55:31) ML Engineers vs. AI engineers

(57:12) Looking forward: the impact of AI

(01:05:48) Model capabilities vs. perceived performance

(01:08:23) Lightning round and final thoughts

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Referenced:

• Chip’s LinkedIn post on what actually improves AI apps: https://www.linkedin.com/posts/chiphuyen_aiapplications-aiengineering-activity-7358971409227792384-y0mf/

• Prediction and Entropy of Printed English: https://www.princeton.edu/~wbialek/rome/refs/shannon_51.pdf

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

•Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord

• First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege

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

• Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill

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

• Stanford webinar—How AI Is Changing Coding and Education, Andrew Ng & Mehran Sahami: https://www.youtube.com/watch?v=J91_npj0Nfw

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

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Lenny’s vibe-coded app made on Lovable: https://gdoc-images-grab.lovable.app/

• Story of Yanxi Palace: https://www.imdb.com/title/tt8865016/

• Steve Jobs’s quote: https://www.goodreads.com/quotes/427317-remembering-that-i-ll-be-dead-soon-is-the-most-important

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Recommended books:

• The Complete Sherlock Holmes: https://www.amazon.com/Complete-Sherlock-Holmes-Volumes/dp/0553328255

• AI Engineering: Building Applications with Foundation Models: https://www.amazon.com/AI-Engineering-Building-Applications-Foundation/dp/1098166302

• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152

• From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google.

We discuss:

1. Why most productivity metrics are a lie

2. Signs that your engineering team could be moving much faster

3. Why AI accelerates coding but developers aren’t speeding up as much as you think

4. AI’s impact on engineers getting into “flow”

5. Her framework for building and scaling a developer experience team

6. The three components of developer experience: flow state, cognitive load, and feedback loops

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Brought to you by:

Mercury—The art of simplified finances: https://mercury.com/

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

Coda—The all-in-one collaborative workspace: https://coda.io/lenny

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Where to find Nicole Forsgren:

• Twitter: https://twitter.com/nicolefv

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

• Website: https://nicolefv.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/

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In this episode, we cover:

(00:00) Introduction to Nicole Forsgren

(05:09) The concept of developer experience (DevEx)

(08:33) Flow state and cognitive load in the age of AI

(12:02) Challenges in measuring productivity with AI

(21:19) The importance of developer experience for business value

(22:20) Common issues and solutions in developer experience

(26:49) Signs your eng team is moving too slow

(29:52) How AI is improving productivity

(33:32) Real examples of productivity improvements

(36:35) Introducing her new book, Frictionless

(43:40) How to get started building a DevEx team

(45:15) The impact of forming developer experience teams

(46:15)  How to measure the impact of DevEx teams

(48:53) Measuring the impact of AI tools on productivity

(55:16) Survey design for developer experience

(57:59) Popular AI tools for developers

(59:08) Bringing a product mindset to DevEx improvements

(01:00:40) AI corner

(01:02:33) Lightning round and final thoughts

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Referenced:

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennysnewsletter.com/p/how-to-measure-and-improve-developer

• DORA: https://dora.dev/

• The SPACE framework: A comprehensive guide to developer productivity: https://getdx.com/blog/space-metrics/

• Measuring developer productivity with the DX Core 4: https://getdx.com/research/measuring-developer-productivity-with-the-dx-core-4/

• Gloria Mark’s website: https://gloriamark.com/

• Taking Flight with Copilot: https://dl.acm.org/doi/10.1145/3589996

• DevEx in Action: https://spawn-queue.acm.org/doi/10.1145/3639443

• CodeX: https://openai.com/codex/

• Devin: https://devin.ai/

• Abi Noda on LinkedIn: https://www.linkedin.com/in/abinoda/

• DX is joining Atlassian: https://getdx.com/blog/dx-is-joining-atlassian/

• GitHub Copilot: https://github.com/features/copilot

• Cursor: https://cursor.com/

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

• Gemini Code Assist: https://codeassist.google/

• Claude Code: https://www.claude.com/product/claude-code

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Love Is Blind on Netflix: https://www.netflix.com/title/80996601

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs

• Ninja Creami: https://www.amazon.com/Ninja-NC301-CREAMi-Containers-Bundle/dp/B0BLGR5JPV/

• Jura coffee maker: https://www.amazon.com/Jura-Nordic-Automatic-Coffee-Machine/dp/B0CF65BFZ1/

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Recommended books:

• Frictionless: https://developerexperiencebook.com/

• DevEx Workbook: https://developerexperiencebook.com/#workbook

• Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599

• Back Mechanic: https://www.amazon.com/Back-Mechanic-Stuart-McGill-2015-09-30/dp/B01FKSGJYC

• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/

• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/dp/B01KBM82M4/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025.

What you’ll learn:

• How Dylan kept internal morale up after the Adobe acquisition fell through

• His approach to maintaining pace and a sense of urgency 13 years in

• How to systematically develop taste

• How Figma decides which product lines to add

• Why Dylan obsesses over “time to value”

• How AI is making design more valuable

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Brought to you by:

Stripe—Helping companies of all sizes grow revenue

—

Transcript: ⁠https://www.lennysnewsletter.com/p/why-ai-makes-design-craft-and-quality-the-new-moat⁠

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175569466/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Dylan Field:

• X: https://x.com/zoink

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

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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 Dylan Field

(03:58) The Adobe deal fallout

(05:50) Maintaining team morale post-deal

(09:13) Strategies for sustaining high performance

(13:37) Maintaining Figma’s unique company culture

(16:22) Dylan’s leadership evolution

(21:03) How to improve clarity as a leader

(24:40) The controversy behind FigJam

(31:06) Lessons from expanding Figma’s core product line

(39:32) Time-to-value

(45:14) Introduction to Figma Make

(48:26) AI app prototyping and the future of Figma Make

(53:38) Lessons from Figma’s AI product launch

(57:47) The importance of craft

(59:54) Developing good taste

(01:05:35) The future of product development

(01:10:32) Why AI won’t steal your job

(01:14:37) AI corner

(01:18:32) Lightning round and final thoughts

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Referenced:

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

• Figma: https://www.figma.com/

• Adobe: https://www.adobe.com/

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao

• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz

• FigJam: https://www.figma.com/figjam/

• Cursor chat: https://help.figma.com/hc/en-us/articles/4403130802199-Use-cursor-chat-in-Figma-Design

• Figma Slides: https://www.figma.com/slides/

• Figma Sites: https://www.figma.com/sites/

• Figma Buzz: https://www.figma.com/buzz/

• Figma Draw: https://www.figma.com/draw/

• Figma Design: https://www.figma.com/design/

• Dev Mode: https://www.figma.com/dev-mode/

• Figma Make: https://www.figma.com/make/

• Zach Lloyd on X: https://x.com/zachlloydtweets

• Warp: https://www.warp.dev/

• Dylan’s post on X about Figma on an AI product leaderboard: https://x.com/zoink/status/1968588014935801884

• Kurt Cobain: https://en.wikipedia.org/wiki/Kurt_Cobain

• Damien Correll on LinkedIn: https://www.linkedin.com/in/damiencorrell/

• Marcin Wichary on LinkedIn: https://www.linkedin.com/in/mwichary/

• Loredana Crisan on LinkedIn: https://www.linkedin.com/in/loredanacrisan/

• Amber Bravo on LinkedIn: https://www.linkedin.com/in/amberbravo/

• Figma’s 2025 AI report: Perspectives from designers and developers: https://www.figma.com/blog/figma-2025-ai-report-perspectives/

• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox#Energy_conservation_policy

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• Pantheon: https://www.imdb.com/title/tt11680642/

• Retro: https://retro.app/

• Thiel Fellowship: https://thielfellowship.org/

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Recommended books:

• Understanding Comics: The Invisible Art: https://www.amazon.com/Understanding-Comics-Invisible-Scott-McCloud/dp/006097625X

• The Spy and the Traitor: The Greatest Espionage Story of the Cold War: https://www.amazon.com/Spy-Traitor-Greatest-Espionage-Story/dp/1101904216

• Codex Seraphinianus: https://www.amazon.com/Codex-Seraphinianus-Anniversary-Luigi-Serafini/dp/0847871045

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions.

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What you’ll learn:

Why Google’s AI products are suddenly taking off after years of perceived stagnation 

How AI is expanding Search rather than replacing it, contrary to what many predicted 

The three core product principles that have helped Robby build multiple billion-user products 

Inside Instagram’s decision to build its own version of Snapchat Stories 

His mantra of “relentless improvement” 

How Google developed AI Mode from concept to launch in just one year 

Why most teams give up too early on potentially transformative products 

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Brought to you by:

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc

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

—

Transcript: https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Robby Stein:

• X: https://x.com/rmstein

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

—

Referenced:

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

• Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image

• Chat GPT: https://chatgpt.com/

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

• Google Lens: https://lens.google/

• AI Google search: https://www.google.com/ai

• Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour

• Alex Rampell on X: https://x.com/arampell

• A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype): https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products

• Look broader, look closer, think younger: Tony Fadell speaks at TED2015: https://blog.ted.com/look-broader-look-closer-think-younger-tony-fadell-speaks-at-ted2015/

• Jobs to Be Done: https://www.christenseninstitute.org/theory/jobs-to-be-done/

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Rinstagram or Finstagram? The curious duality of the modern Instagram user: https://www.theguardian.com/technology/2016/sep/26/rinstagram-finstagram-instagram-accounts

• V03: https://v03ai.com/

• Pirate GPT: https://www.kickstarter.com/projects/silentmeditation/pirate-gpt/

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Dune on HBO Max: https://www.hbomax.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

• Top Gun: Maverick: https://www.imdb.com/title/tt1745960/

• Purple pillows: https://purple.com/pillows

• Avocado pillow: https://www.avocadogreenmattress.com/products/green-pillow

• Justin Bieber’s website: https://www.justinbiebermusic.com/

• Scooter Braun’s website: https://scooterbraun.com/

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Recommended books:

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612

• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654

• Aurora: https://www.amazon.com/Aurora-High-Stakes-Survival-Navigate-Darkness/dp/0062916475

• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135202

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses.

What you’ll learn:

What actually happened with Meta’s $14 billion investment in Scale AI

Why AI models still need human experts to improve, and how that relationship is evolving

How AI models learn from experts building websites and debugging code

The business lessons from building Uber Eats from zero to $20 billion

Why most enterprise data is useless for AI models today

Why urgent daily problems beat super-valuable occasional problems when building products

How to think independently when building new products and businesses

—

Brought to you by:

Merge—The fastest way to ship 220+ integrations: http://merge.dev/lenny

Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/

Mercury—The art of simplified finances: https://mercury.com/

—

Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation

—

Where to find Jason Droege:

• X: https://x.com/jdroege

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

—

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 Jason Droege

(06:01) Jason’s early career and lessons learned

(10:27) The current state of Scale AI

(12:37) The shift to expert data labeling

(17:02) Challenges and strategies in finding experts

(18:48) Reinforcement learning and AI environments

(28:18) The future of AI and human involvement

(31:21) The role of evals

(35:25) What AI models will look like in the next few years

(41:43) Building Uber Eats and understanding customer needs

(48:19) The importance of independent thinking

(50:45) Setting high standards for new businesses

(53:03) Exploring and selecting business ideas

(57:07) The McDonald’s story

(01:00:13) The role of gross margins in business feasibility

(01:04:49) Why Jason says, “Not losing is a precursor to winning”

(01:09:12) Hiring and building teams

(01:12:11) AI corner

(01:14:47) Lightning round and final thoughts

—

Referenced:

• Travis Kalanick on X: https://x.com/travisk

• Scour: https://en.wikipedia.org/wiki/Scour_Inc.

• Scale: https://scale.com/

• Alexandr Wang on X: https://x.com/alexandr_wang

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

• Brendan Foody’s post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048

• MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/

• Uber Eats: https://www.ubereats.com/

• Stephen Chau on X: https://x.com/thestephenchau

• a16z Podcast: https://a16z.com/podcasts/a16z-podcast/

• F1: The Movie: https://www.imdb.com/title/tt16311594/

• V03: https://v03ai.com/

• Careers at Scale: https://scale.com/careers

—

Recommended books:

• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152

• The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/

• Good to Great: Why Some Companies Make the Leap . . . And Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue.

What you’ll learn:

1. How to use the explore-exploit framework to find new growth opportunities

2. How showing premium features to free users doubled Grammarly’s upgrades to paid plans

3. What good retention looks like for a consumer subscription app

4. Why resurrected users drive 80% of mature product growth

5. Why “reverse trials” work better than time-based trials

6. The three pillars of successful gamification: core loop, metagame, and profile

—

Brought to you by:

Vanta—Automate compliance. Simplify security.

Jira Product Discovery—Confidence to build the right thing

Miro—A collaborative visual platform where your best work comes to life

—

Where to find Albert Cheng:

• X: https://x.com/albertc248

• LinkedIn: https://www.linkedin.com/in/albertcheng1/

• Chess.com: https://www.chess.com/member/Goniners

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

—

Referenced:

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit

• Grammarly: https://www.grammarly.com/

• Reforge: https://www.reforge.com/

• Chess.com: https://www.chess.com/

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

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

• Figma: https://www.figma.com/

• Cursor: https://cursor.com/

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

• Claude Code: https://www.anthropic.com/claude-code

• GitHub Copilot: https://github.com/features/copilot

• Noam Lovinsky on LinkedIn: https://www.linkedin.com/in/noaml/

• The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack): https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product

• Kyla Siedband on LinkedIn: https://www.linkedin.com/in/kylasiedband/

• The Duolingo handbook: https://blog.duolingo.com/handbook/

• Lenny’s post on X about the Duolingo handbook: https://x.com/lennysan/status/1889008405584683091

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Kasparov vs. Deep Blue | The Match That Changed History: https://www.chess.com/article/view/deep-blue-kasparov-chess

• Magnus Carlsen: https://en.wikipedia.org/wiki/Magnus_Carlsen

• Elo rating system: https://www.chess.com/terms/elo-rating-chess

• Stockfish: https://en.wikipedia.org/wiki/Stockfish_(chess)

• AlphaGo on Prime Video: https://www.primevideo.com/detail/AlphaGo/0KNQHKKDAOE8OCYKQS9WSSDYN0

• Statsig: https://www.statsig.com/

• The State of Product in 2026: Navigating Change, Challenge, and Opportunity: https://www.atlassian.com/blog/announcements/state-of-product-2026

• Erik Allebest on LinkedIn: https://www.linkedin.com/in/erikallebest/

• Daniel Rensch on X: https://x.com/danielrensch

• Chariot: https://en.wikipedia.org/wiki/Chariot_(company)

• San Francisco 49ers: https://www.49ers.com/

• Breville Barista Express: https://www.breville.com/en-us/product/bes870

—

Recommended books:

• Snuggle Puppy!: A Little Love Song: https://www.amazon.com/Snuggle-Puppy-Little-Boynton-Board/dp/1665924985

• Ogilvy on Advertising: https://www.amazon.com/Ogilvy-Advertising-David/dp/039472903X

• Dark Squares: How Chess Saved My Life: https://www.amazon.com/Dark-Squares-Chess-Saved-Life/dp/1541703286

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provides a practical framework for creating products that serve both functional and emotional needs. Based in Paris, she now coaches founders and CPOs on implementing delight strategies in their organizations.

What you’ll learn:

1. Why delight is a business strategy, not just “sprinkling confetti” on top of functionality

2. How to identify emotional motivators that drive product retention

3. The 50-40-10 rule for balancing delight in your roadmap

4. The 4-step delight model

5. The origin story of Spotify’s Discover Weekly

6. Why B2B products need delight just as much as B2C products

7. How to get buy-in from skeptical leaders who think delight is a luxury

—

Brought to you by:

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

Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny

LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174199489/my-biggest-takeaways-from-this-conversation

—

Where to find Nesrine Changuel:

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

• Newsletter: https://nesrinechanguel.substack.com/

• Website: https://nesrine-changuel.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 Nesrine and product delight

(04:56) Why delight matters

(09:17) What makes a feature “delightful”

(12:29) The three pillars of delight

(13:03) Pillar 1: Removing friction (Uber refund example)

(15:07) Pillar 2: Anticipating needs (Revolut eSIM example)

(17:21) Pillar 3: Exceeding expectations (Edge coupon example)

(18:35) The “confetti effect” and when it actually works

(22:02) B2B vs. B2C: Why all products need emotional connection

(29:52) The Delight Model: A 4-step framework

(30:57) Step 1: Identifying user motivators (functional and emotional)

(33:55) Step 2: Converting motivators into product opportunities

(34:46) Step 3: Identifying solutions with the delight grid

(36:46) Step 4: Validating ideas with the delight checklist

(40:22) The Delight Model summarized

(42:18) The importance of familiarity (Spotify Discover Weekly story)

(45:21) Real examples: Chrome’s tab management solution

(51:32) Google Meet’s solution for “Zoom fatigue”

(55:02) Getting buy-in from skeptical leaders

(59:39) Prioritizing delight: The 50-40-10 rule

(1:02:41) Creating a culture of delight in your organization

(1:06:45) The habituation effect

(1:08:15) When delight goes wrong: Apple reactions example

(1:10:21) How delight motivates product teams

(1:12:24) Lightning round and final thoughts

—

Referenced:

• Spotify: https://open.spotify.com/

• Linear: https://linear.app/

• How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product

• Jira: https://www.atlassian.com/software/jira

• Asana: https://asana.com/

• Monday: https://monday.com/

• The Product Delight Model: https://nesrinechanguel.substack.com/p/the-product-delight-model

• Revolut: https://www.revolut.com/

• How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers

• Microsoft Cashback: https://www.microsoft.com/en-us/edge/features/shopping-cashback

• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra

• Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley

• Workday: https://www.workday.com/

• SAP: https://www.sap.com/

• ServiceNow: https://www.servicenow.com/

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

• GitHub: https://github.com/

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

• Snowflake: https://www.snowflake.com/

• Data Superheroes: https://www.snowflake.com/en/data-superheroes/

• Google Meet: https://meet.google.com/

• Andy Nesling on LinkedIn: https://www.linkedin.com/in/andynesling/

• Matic: https://maticrobots.com/

• Diego Sanchez’s (Senior Product Manager at Buffer) post on LinkedIn: https://www.linkedin.com/feed/update/urn:li:activity:7365014292091346945/

• Miro: https://miro.com/

• Arc browser: https://arc.net/

• Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look

• Migros Supermarket: https://www.migros.ch/

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

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

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Suno: https://suno.com

• Snapchat: https://www.snapchat.com/

• Use Reactions, Presenter Overlay, and other effects when videoconferencing on Mac: https://support.apple.com/en-us/105117

• Dr. Lipp: https://drlipp.com/

• How to be the best coach to product people | Petra Wille (Strong Product People): https://www.lennysnewsletter.com/p/how-to-be-the-best-coach-to-product

• The Great American Baking Show: https://www.imdb.com/title/tt21822674/

• Le Meilleur Pâtissier: https://en.wikipedia.org/wiki/Le_Meilleur_P%C3%A2tissier

• The Upside on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.3cb8500f-31af-9f4f-5dec-701e086d58e8

• The Intouchables: https://www.imdb.com/title/tt1675434/

• Yoyo stroller: https://www.stokke.com/USA/en-us/category/strollers/yoyo-strollers

• UppaBaby strollers: https://uppababy.com/strollers/

—

Recommended books:

• Product Delight: How to Make Your Product Stand Out with Emotional Connection: https://www.amazon.com/Product-Delight-Stand-Emotional-Connection-ebook/dp/B0FGZ93D9Y/

• Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think: https://www.amazon.com/Factfulness-Reasons-World-Things-Better/dp/1250107814

• STRONG Product Communities: The Essential Guide to Product Communities of Practice: https://www.amazon.com/STRONG-Product-Communities-Essential-Practice/dp/3982235189/r

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Hamel Husain and Shreya Shankar teach the world’s most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that’ll help you improve your AI product.

What you’ll learn:

1. WTF evals are

2. Why they’ve become the most important new skill for AI product builders

3. A step-by-step walkthrough of how to create an effective eval

4. A deep dive into error analysis, open coding, and axial coding

5. Code-based evals vs. LLM-as-judge

6. The most common pitfalls and how to avoid them

7. Practical tips for implementing evals with minimal time investment (30 minutes per week after initial setup)

8. Insight into the debate between “vibes” and systematic evals

—

Brought to you by:

Fin—The #1 AI agent for customer service

Dscout—The UX platform to capture insights at every stage: from ideation to production

Mercury—The art of simplified finances

—

Where to find Shreya Shankar

• X: https://x.com/sh_reya

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

• Website: https://www.sh-reya.com/

• Maven course: https://bit.ly/4myp27m

—

Where to find Hamel Husain

• X: https://x.com/HamelHusain

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

• Website: https://hamel.dev/

• Maven course: https://bit.ly/4myp27m

—

In this episode, we cover:

(00:00) Introduction to Hamel and Shreya

(04:57) What are evals?

(09:56) Demo: Examining real traces from a property management AI assistant

(16:51) Writing notes on errors

(23:54) Why LLMs can’t replace humans in the initial error analysis

(25:16) The concept of a “benevolent dictator” in the eval process

(28:07) Theoretical saturation: when to stop

(31:39) Using axial codes to help categorize and synthesize error notes

(44:39) The results

(46:06) Building an LLM-as-judge to evaluate specific failure modes

(48:31) The difference between code-based evals and LLM-as-judge

(52:10) Example: LLM-as-judge

(54:45) Testing your LLM judge against human judgment

(01:00:51) Why evals are the new PRDs for AI products

(01:05:09) How many evals you actually need

(01:07:41) What comes after evals

(01:09:57) The great evals debate

(1:15:15) Why dogfooding isn’t enough for most AI products

(01:18:23) OpenAI’s Statsig acquisition

(1:23:02) The Claude Code controversy and the importance of context

(01:24:13) Common misconceptions around evals

(1:22:28) Tips and tricks for implementing evals effectively

(1:30:37) The time investment

(1:33:38) Overview of their comprehensive evals course

(1:37:57) Lightning round and final thoughts

—

LLM Log Open Codes Analysis Prompt:

Please analyze the following CSV file. There is a metadata field which has an nested field called z_note that contains open codes for analysis of LLM logs that we are conducting. Please extract all of the different open codes. From the _note field, propose 5-6 categories that we can create axial codes from.

—

Referenced:

• Building eval systems that improve your AI product: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve

• Mercor: https://mercor.com/

• Brendan Foody on LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b

• Nurture Boss: https://nurtureboss.io/

• Braintrust: https://www.braintrust.dev/

• Andrew Ng on X: https://x.com/andrewyng

• Carrying Out Error Analysis: https://www.youtube.com/watch?v=JoAxZsdw_3w

• Julius AI: https://julius.ai/

• Brendan Foody on X—“evals are the new PRDs”: https://x.com/BrendanFoody/status/1939764763485171948

• Who Validates the Validators? Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences: https://dl.acm.org/doi/abs/10.1145/3654777.3676450

• Lenny’s post on X about evals: https://x.com/lennysan/status/1909636749103599729

• Statsig: https://statsig.com/

• Claude Code: https://www.anthropic.com/claude-code

• Cursor: https://cursor.com/

• Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor

• Frozen: https://www.imdb.com/title/tt2294629/

• The Wire on HBO: https://en.wikipedia.org/wiki/The_Wire

—

Recommended books:

• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935

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

• Machine Learning: https://www.amazon.com/Machine-Learning-Tom-M-Mitchell/dp/1259096955

• Artificial Intelligence: A Modern Approach: https://www.amazon.com/Artificial-Intelligence-Modern-Approach-Global/dp/1292401133/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago!

In our conversation, we discuss:

1. The three core manager skills that translate directly to managing AI agents

2. How her team uses AI to learn new skills 10x faster

3. The “diagnose with data, treat with design” framework for balancing gut and data

4. Why hypergrowth AI companies have terrible data infrastructure (and why it doesn’t matter)

5. How to give feedback that actually lands—including Julie’s exact script for difficult conversations

6. What Julie’s teaching her kids about an AI future (hint: it’s not coding or STEM)

—

Brought to you by:

Mercury — The art of simplified finances

DX — The developer intelligence platform designed by leading researchers

PostHog—How developers build successful products

—

Transcript: https://www.lennysnewsletter.com/p/from-managing-people-to-managing-ai-julie-zhuo

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172723725/my-biggest-takeaways-from-this-conversation

—

Where to find Julie Zhuo:

• X: https://x.com/joulee

• LinkedIn: https://www.linkedin.com/in/julie-zhuo/

• Website: https://www.juliezhuo.com/

• Newsletter: https://lg.substack.com/

• Sundial: https://sundial.so/

—

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) Welcome back, Julie!

(05:18) The success of The Making of a Manager

(08:41) Why AI will make everyone a manager

(11:38) The future of management roles

(14:00) Empowering teams with AI

(21:30) Specific roles being accelerated by AI

(26:53) Data analysis in AI companies

(32:02) The role of data in design

(37:21) The evolving role of managers in the AI era

(40:22) Embracing change and uncertainty

(42:14) Timeless lessons for managers

(49:03) Balancing strengths and weaknesses

(57:49) Building a feedback culture

(01:05:33) Creating win-win situations

(01:09:27) Being aware of your own energy and conviction

(01:12:12) Navigating disagreements with higher-ups

(01:15:57) AI corner

(01:20:08) Contrarian corner

(01:23:14) Lightning round and final thoughts

—

Referenced:

• Julie Zhuo on accelerating your career, impostor syndrome, writing, building product sense, using intuition vs. data, hiring designers, and moving into management: https://www.lennysnewsletter.com/p/episode-2-julie-zhuo

• Waymo: https://waymo.com/

• How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO): https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai

• Cursor: https://cursor.com/

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

• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• 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

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

• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop

• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/

• Methaphone: https://methaphone.com/

• Replit: https://replit.com/

• “Baby” by Justin Bieber on Spotify: https://open.spotify.com/track/6epn3r7S14KUqlReYr77hA

• Kingdom Rush: https://www.kingdomrush.com/

• Dr. Becky on TikTok: https://www.tiktok.com/@drbeckyatgoodinside

• Emily Oster on TikTok: https://www.tiktok.com/@profemilyoster

• La La Land on Netflix: https://www.netflix.com/title/80095365

• Granola: https://www.granola.ai/

• Matic robots: https://maticrobots.com/

• Limitless pendant: https://www.limitless.ai/

• How I AI: https://www.youtube.com/@howiaipodcast

—

Recommended books:

• The Making of a Manager: What to Do when Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0525540423

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

• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0061673730

• Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020

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

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve their models. In this conversation, Brendan explains why evals have become the critical bottleneck for AI progress, how he discovered this massive opportunity, and what the future of work might look like in an AI-driven economy.

What you’ll learn:

1. Why evals are becoming the primary bottleneck for AI progress and what this means for AI startups

2. How Mercor grew to $500M revenue in 17 months (fastest in history)

3. Brendan’s meeting with xAI that changed his company’s trajectory

4. Which skills and jobs will remain most valuable as AI continues to advance (hint: jobs with “elastic” demand)

5. Why Brendan believes AGI and superintelligence are not happening anytime soon

6. The three unique core values that drove Mercor’s success

7. How Harvard Lampoon writers are making Claude funnier

—

Brought to you by:

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

Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams

Enterpret—Transform customer feedback into product growth

—

Transcript: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/173303790/my-biggest-takeaways-from-this-conversation

—

Where to find Brendan Foody:

• X: https://x.com/BrendanFoody

• LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b/

—

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 Brendan Foody and Mercor

(05:38) The “era of evals”

(09:26) Understanding the AI training landscape

(17:10) The future of work and AI

(25:54) The evolution of labor markets

(29:55) Understanding how AI models are trained

(38:58) Building Mercor

(53:27) Lessons from past ventures

(56:55) The future of AI and model improvement

(01:00:41) His personal use of AI and final thoughts

—

References: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity.

In our conversation, we discuss:

1. His 7-step playbook to rank #1 in ChatGPT

2. Why ChatGPT traffic converts 6x better than Google

3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years)

4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments

5. Why help-center content can suddenly be your highest-ROI investment

6. The specific Reddit strategy that works (spoiler: be authentic)

7. Why AI-generated content doesn’t work

—

Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Vanta—Automate compliance. Simplify security.

Great Question—Empower everyone to run great research

—

Where to find Ethan Smith:

• Twitter: https://twitter.com/ethan_l_s

• LinkedIn: https://bit.ly/ethans-linkedin

• Graphite: https://graphite.io/

• Graphite Research Papers: https://bit.ly/graphite-five-percent

—

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) Welcome back, Ethan

(04:34) The changing landscape of SEO

(06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization)

(08:13) The impact of AEO

(11:51) How early-stage startups can win at AEO

(14:34) The quality of AEO leads

(15:35) On-site vs. off-site traffic

(16:32) Reddit’s role in AEO and avoiding spam

(20:11) How AI models use citations (RAG)

(21:41) Key principles for winning at AEO

(25:00) Avoiding hyper-SEOed content, and the importance of originality

(28:55) Actionable AEO playbook: steps and experiments

(33:35) Tracking, measuring, and share of voice

(38:34) Adapting AEO for B2B, commerce, and early-stage companies

(41:11) Is letting AI index your content good?

(43:06) Experimentation, control groups, and measuring results

(46:15) The future of AEO, SEO, and search channels

(51:35) AI-generated content: what works and what doesn’t

(55:25) The dangers of infinite AI derivatives

(58:44) The future: convergence of LLMs and search

(01:00:40) Help-center optimization and the long tail

(01:03:18) Lightning round and final thoughts

—

Resources and episode mentions: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom.

In our conversation, Ben shares:

1. Why “founder mode” is half right and half dangerously wrong

2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger

3. Where the biggest AI startup opportunities remain

4. Why you need to run toward fear, never away

5. The one trait that predicts that a founder will fail as CEO

6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists

—

Brought to you by:

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

Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny

Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation

—

Where to find Ben Horowitz:

• X: https://x.com/bhorowitz

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

• Website: https://benhorowitz.com/

• Andreessen Horowitz’s website: https://a16z.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 Ben Horowitz

(04:09) Important leadership lessons from Shaka Senghor

(10:15) Running toward fear and why hesitation kills companies

(19:35) Who shouldn’t start a company

(22:36) The Databricks story: thinking bigger

(24:54) Managerial leverage and CEO psychology

(28:06) When founders should be replaced as CEOs

(31:20) Normalizing failure for CEOs

(37:57) Counterintuitive lessons about building companies

(42:31) “Good Product Manager/Bad Product Manager”

(48:21) Product managers as leaders

(51:16) Why a16z invested in Adam Neumann after WeWork

(56:23) Is AI in a bubble?

(01:02:43) The biggest opportunities in AI

(01:12:51) Why U.S. leadership in AI matters

(01:18:53) The Paid in Full Foundation for hip-hop pioneers

(01:23:18) Lightning round: book recommendations, products, and life mottos

—

References: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they’ve learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology.

What you’ll learn:

1. The “shipyard” framework: why the best AI teams embrace controlled chaos

2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years

3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency

4. How to identify “sharp problems”

5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products

6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck

7. Their biggest product lesson from 50 combined years

—

Brought to you by:

Mercury—The art of simplified finances

Vanta—Automate compliance. Simplify security.

Coda—The all-in-one collaborative workspace

—

Where to find Oji and Ezinne:

• ProductMind on Substack: https://substack.com/@ojiudezue

• ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco

• ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos

• ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ

• ProductMind website: https://www.productmind.co/

• Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/

• Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/

—

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 Oji and Ezinne

(04:14) The evolving role of product managers

(08:01) Challenges and opportunities in product management

(10:34) Sharp problems

(12:37) The shipyard model for product development

(17:02) Hiring PMs in the AI era

(24:55) The importance of staying humble

(27:16) Hands-on learning and personal projects

(39:10) Companies succeeding with AI adoption

(46:25) Lessons from 50 years in product

(49:22) Simplicity in design

(51:24) The role of communication in strategy

(55:17) Career intentions and personal growth

(01:00:00) Ethics and responsibility in product management

(01:03:09) Introducing Building Rocketships

(01:06:42) Lightning round and final thoughts

—

Referenced:

• How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft): https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma

• Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian): https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing

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

• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/

• Brownian motion: https://en.wikipedia.org/wiki/Brownian_motion

• Calendly: https://calendly.com/

• Women in Product: https://womenpm.org/

• Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley

• Home Assistant: https://www.home-assistant.io/

• What people are vibe coding (and actually using): https://www.lennysnewsletter.com/p/what-people-are-vibe-coding-and-actually

• How many layers should I wear today?: https://layers.today/

• Typeform: https://www.typeform.com/

• David Okuniev on X: https://x.com/okuiux

• Clay: https://www.clay.com/

• Martin Eriksson on LinkedIn: https://www.linkedin.com/in/martineriksson/

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• Dave Mendlen on LinkedIn: https://www.linkedin.com/in/davemendlen/

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

• How to kickstart and scale a marketplace business: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace

• Forever on Netflix: https://www.netflix.com/title/81418639

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

• Sinners: https://www.imdb.com/title/tt31193180/

• Claude: https://claude.ai/

• Nespresso Vertuo: https://www.nespresso.com/us/en/vertuo-coffee-machines

• Gamma: https://gamma.app/

• Framer: https://www.framer.com/

• Lovable: https://lovable.dev/

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

• Llama: https://www.llama.com/

—

Recommended books:

• Building Rocketships: Product Management for High-Growth Companies: https://www.amazon.com/Building-Rocketships-Management-High-Growth-Companies/dp/1962339068

• Coda version of Building Rocketships: https://www.productmind.co/brpro

• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

• The Let Them Theory: A Life-Changing Tool That Millions of People Can’t Stop Talking About: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.

What you’ll learn:

1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)

2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally

3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)

4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment

5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era

6. Why evals can kill innovation (and when to use “vibes” instead)

—

Brought to you by:

LucidLink—Real-time cloud storage for teams

DX—The developer intelligence platform designed by leading researchers

Claude.ai—The AI for problem solvers and enterprise

—

Where to find Howie Liu

• X: https://x.com/howietl

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

• Email: howie@airtable.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 Howie Liu and Airtable

(04:05) The “Airtable is dead” viral tweet controversy

(08:07) The rise of IC CEOs

(10:57) AI’s paradigm shift in product development

(16:27) Specific changes Airtable has made

(21:38) Fast- and slow-thinking teams

(32:57) The emergence of new form factors in AI models

(34:48) Airtable’s vision and philosophy

(40:20) Empowering teams with AI tools

(46:50) Encouraging experimentation and play

(50:55) Cross-functional skills in product teams

(01:03:35) The importance of evals and open-ended testing

(01:08:06) Key strategies for AI-driven success

(01:12:43) Counterintuitive startup wisdom

(01:22:21) Don't step away from the details that you love

(01:25:50) Advice for aspiring engineers and designers

(01:30:00) Lightning round and final thoughts

—

Referenced:

• Airtable: https://www.airtable.com/

• All In podcast: https://allin.com/

• Nikita Bier on X: https://x.com/nikitabier

• Figma: https://www.figma.com/

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Every: https://every.to/

• Cursor: https://cursor.com/

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

• Windsurf: https://windsurf.com/

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Rippling: https://www.rippling.com/

• Omni: https://www.airtable.com/lp/ai-psu-plp

• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Palantir: https://www.palantir.com/

• Harvey: https://www.harvey.ai/

• v0: https://v0.dev/

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

• Replit: https://replit.com/

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

• Lovable: https://lovable.dev/

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

• Runway Game Worlds: https://play.runwayml.com/login

• Sesame: https://www.sesame.com

• NotebookLM: https://notebooklm.google

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

• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/

• Stripe: https://stripe.com/

• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair

• 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

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

• IDEO design thinking: https://designthinking.ideo.com/

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

• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52

• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d

• Self Edge: https://www.selfedge.com/

• Studio D’Artisan: https://www.selfedge.com/studio-dartisan

• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/

• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health

—

Recommended books:

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032

• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger.

What you’ll learn:

1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders

2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era

3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle

4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning

5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company

6. The three-phase pattern every successful AI company follows (and why most fail at phase one)

7. The rise of code-native interfaces and why GUIs might be going the way of the desktop

8. What Asha learned from Satya Nadella about optimism

—

Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

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

Fin—The #1 AI agent for customer service: https://fin.ai/lenny

—

Transcript: ⁠https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Asha Sharma:

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

• Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/

—

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 Asha Sharma

(04:18) From “product as artifact” to “product as organism”

(06:20) The rise of post-training and the future of AI product development

(09:10) Successful AI companies: patterns and pitfalls

(12:01) The evolution of full-stack builders

(14:15) “The loop, not the lane”—the new organizing principle

(16:24) The future of user interfaces: from GUI to code-native

(19:34) The rise of the agentic society

(22:58) The “work chart” vs. the “org chart”

(26:24) How Microsoft is using agents

(28:23) Planning and strategy in the AI landscape

(35:38) The importance of platform fundamentals

(39:31) Lessons from industry giants

(42:10) What’s driving Asha

(44:30) Reinforcement learning (RL) and optimization loops

(49:19) Lightning round and final thoughts

—

Referenced:

• Copilot: https://copilot.microsoft.com/

• Cursor: https://cursor.com/

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

• Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• GitHub: https://github.com

• Dragon Medical One: https://www.microsoft.com/en-us/health-solutions/clinical-workflow/dragon-medical-one

• Windsurf: https://windsurf.com/

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Lovable: https://lovable.dev/

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

• Bolt: http://bolt.com

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Replit: https://replit.com/

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

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

• Sierra: https://sierra.ai/

• Spark: https://github.com/features/spark

• Peter Yang on X: https://x.com/petergyang

• How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management

• Instacart: http://instacart.com/

• Terminator: https://en.wikipedia.org/wiki/Terminator_(franchise)

• Porch Group: https://porchgroup.com/

• WhatsApp: https://www.whatsapp.com/

• Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html

• Satya Nadella on X: https://x.com/satyanadella

• Perfect Match 360°: Artificial intelligence to find the perfect donor match: https://ivi-fertility.com/blog/perfect-match-360-artificial-intelligence-to-find-the-perfect-donor-match/

• OpenAI’s GPT-5 shows potential in healthcare with early cancer detection capabilities: https://economictimes.indiatimes.com/news/international/us/openais-gpt-5-shows-potential-in-healthcare-with-early-cancer-detection-capabilities/articleshow/123173952.cms

• F1: The Movie: https://www.imdb.com/title/tt16311594/

• For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7

• The Home Depot: https://www.homedepot.com/

• Dewalt Powerstack: https://www.dewalt.com/powerstack

• Regret Minimization Framework: https://s3.amazonaws.com/kajabi-storefronts-production/sites/2147500522/themes/2148012322/downloads/rLuObc2QuOwjLrinx5Yu_regret-minimization-framework.pdf

—

Recommended books:

• The Thinking Machine: Jensen Huang, Nvidia, and the World’s Most Coveted Microchip: https://www.amazon.com/Thinking-Machine-Jensen-Coveted-Microchip/dp/0593832698

• Tomorrow, and Tomorrow, and Tomorrow: https://www.amazon.com/dp/0593466497

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months.

What you’ll learn:

1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months

2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves

3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter

4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything

5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity

6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive

—

Brought to you by:

CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny

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

Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/

—

Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation

—

Where to find Garrett Lord:

• X: https://x.com/garrettlord

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

• Email: Garrett@joinhandshake.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 Garrett Lord

(05:00) Understanding data labeling and its importance

(13:08) The role of experts in AI model training

(15:35) The future of AI and human collaboration

(24:17) Why AI won’t eliminate entry-level jobs

(27:58) The continuous improvement of AI models

(33:05) The emergence of Handshake’s new business model

(37:07) Incubating new ideas in established companies

(40:42) Handshake's competitive advantage

(45:43) Scaling up and meeting market demand

(48:38) Overcoming challenges and adapting

(53:08) The importance of separate teams and ownership

(57:26) The future of job matching with AI

(01:00:30) The biggest bottlenecks to advancing models further

(01:02:37) Lightning round and final thoughts

—

Referenced:

• GPQA: https://github.com/idavidrein/gpqa

• Handshake: https://joinhandshake.com/

• 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

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• Goldman Sachs: https://www.goldmansachs.com/

• General Motors: https://www.gm.com/

• Google: https://about.google/

• Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/

• Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/

• Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/

• Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac

• SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet

• Careers at Handshake: https://joinhandshake.com/careers/

—

Recommended books:

• Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296

• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies.

We discuss:

1. Why Eoghan believes most late-stage companies won’t survive the AI transition

2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction

3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail)

4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+

5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket

6. The cultural transformation required to compete with AI-native startups

7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach

—

Brought to you by:

Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny

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

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

—

Transcript: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation

—

Where to find Eoghan McCabe:

• X: https://x.com/eoghan

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

• Website: https://eoghanmccabe.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 Eoghan

(05:00) The state of Intercom

(09:53) The decision to pivot to AI

(12:33) Why Eoghan is "anti-bot" in customer service

(16:19) Pricing strategy evolution

(19:26) Implementing the AI transformation

(26:11) Cultural and organizational changes

(31:18) Surviving a coup attempt

(40:05) The future of AI and business

(45:11) AI's impact on jobs

(48:44) AI and human creativity

(50:26) The importance of young AI talent

(55:00) The cultural shift in AI adoption

(58:00) Personal growth and leadership

(01:04:34) Intercom’s success in producing product leaders

(01:11:05) Intercom’s unique company culture

(01:14:11) Lightning round and final thoughts

—

Referenced:

• Intercom: https://www.intercom.com/

• Fin: https://fin.ai/

• Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

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

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• Fergal Reid on LinkedIn: https://www.linkedin.com/in/fergalreid/

• How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product

• Yosi Amram’s website: https://yamram.com/

• (Nathaniel Russell) Ego Death Now: https://heythereprojects.shop/products/copy-of-nathaniel-russell-space-is-a-place

• Daniel Kahneman: https://en.wikipedia.org/wiki/Daniel_Kahneman

• Palantir: https://www.palantir.com/

• Stripe: https://stripe.com/

• Revolut: https://www.revolut.com/en-US/

• Paul Adams on LinkedIn: https://www.linkedin.com/in/pauladams

• What AI means for your product strategy | Paul Adams (CPO of Intercom): https://www.lennysnewsletter.com/p/what-ai-means-for-your-product-strategy

• Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm

• N26: https://n26.com/en-eu

• Notion: https://www.notion.so/

• Coinbase: https://www.coinbase.com/

• True Detective on Max: https://www.hbomax.com/shows/true-detective/9a4a3645-74e0-4e4d-9f35-31464b402357

• 28 Years Later: https://www.imdb.com/title/tt10548174/

• Trainspotting: https://www.imdb.com/title/tt0117951/

• 28 Days Later: https://www.imdb.com/title/tt0289043/

• Fellow: https://fellowproducts.com/

• Porsche 911: https://www.porsche.com/usa/models/911/

• Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto

—

Recommended book:

• Nuclear War: A Scenario: https://www.amazon.com/Nuclear-War-Scenario-Annie-Jacobsen/dp/0593476093

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.

Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT.

In this conversation, you’ll learn:

1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2)

2. Why ChatGPT’s platform launch could be bigger than Facebook’s early platform

3. The exact signals that ChatGPT will launch a third-party platform within six months

4. Why you have six months (not years) to make your platform bet

5. Why companies that don’t integrate with ChatGPT will lose to competitors that do

6. How Zynga grew to $1B by betting on Facebook’s platform early (before it was obvious)

7. Why so few companies are actually doing what they need to be doing right now

—

Brought to you by:

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

Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny

Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation

—

Where to find Brian Balfour:

• X: https://twitter.com/bbalfour

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

• Website: https://brianbalfour.com/

• Substack: https://blog.brianbalfour.com/

• Podcast: https://www.reforge.com/podcast/unsolicited-feedback

—

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) Welcome back, Brian!

(04:13) The changing landscape of product growth

(05:09) The importance of distribution

(08:14) The role of new distribution platforms

(09:45) The four-step cycle of distribution platforms

(17:38) Examples of platform cycles

(30:01) The rise of ChatGPT

(44:47) The future of AI agents

(46:01) Preferred partners and platform credibility

(47:18) Monetization mechanisms and free tiers

(48:14) Betting strategies for startups

(01:04:34) Adopting AI tools: challenges and strategies

(01:08:41) The importance of hard constraints

(01:14:23) Effective AI adoption in companies

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

—

Referenced:

• The Next Great Distribution Shift: https://blog.brianbalfour.com/p/the-next-great-distribution-shift

• Brian Balfour: 10 lessons on career, growth, and life: https://www.lennysnewsletter.com/p/brian-balfour-10-lessons-on-career

• This Week #9: Breaking into growth, leading with influence, and (not) stepping on toes: https://www.lennysnewsletter.com/p/this-week-9-breaking-into-growth

• Distribution vs. Innovation: https://a16z.com/distribution-vs-innovation/

• On Platform Shifts and AI: https://caseyaccidental.com/on-platform-shifts-and-ai/

• How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within

• Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey

• ChatGPT: https://chatgpt.com/

• Claude: https://claude.ai/

• Gemini: https://gemini.google.com/

• Vine: https://en.wikipedia.org/wiki/Vine_(service)

• Periscope: https://en.wikipedia.org/wiki/Periscope_(service)

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

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

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

• Lycos: https://www.lycos.com/

• HubSpot: https://www.hubspot.com/

• Zynga: https://www.zynga.com/

• TBPN: https://www.tbpn.com/

• Deedy Das on LinkedIn: https://www.linkedin.com/in/debarghyadas/

• ChatGPT’s product retention curves are a product manager's wet dream: https://www.linkedin.com/posts/debarghyadas_chatgpts-product-retention-curves-are-a-activity-7338384752393035776-ice1/

• Windsurf: https://windsurf.com/

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

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

• Udemy: https://www.udemy.com/

• Cursor: https://cursor.com/

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

• Notion: https://www.notion.com/

• Airtable: https://www.airtable.com/

• Monday: monday.com

• Sierra: http://sierra.ai

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

• Introducing ChatGPT agent: bridging research and action: https://openai.com/index/introducing-chatgpt-agent/

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• Marc Andreessen on Why Optimism Is the Safest Bet: https://nymag.com/marc-andressen-2014-10-20/

• Reforge: https://www.reforge.com

• Reforge Insights: https://www.reforge.com/insights

• Shopify: https://www.shopify.com/

• 25 proven tactics to accelerate AI adoption at your company: https://www.lennysnewsletter.com/p/25-proven-tactics-to-accelerate-ai

• Clouded Judgement: https://cloudedjudgement.substack.com/

• NFX: https://www.nfx.com/news

• James Currier: https://www.nfx.com/team/james-currier

• Hallway Chat: https://www.hallwaychat.co/

• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/

• Silicon Valley on HBO: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d

• Stick: https://tv.apple.com/us/show/stick/umc.cmc.52w04zy67tiv11p8xvbc57wmc

• Ergonofis standing desks: https://ergonofis.com/en-us/collections/standing-desks

• Coping with the loss of a child and protecting your time | Brian Balfour (father of 2, CEO and founder Reforge, venture partner): https://www.startupdadpod.com/coping-with-the-loss-of-a-child-and-protecting-your-time-brian-balfour-father-of-2-ceo-and-found/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things.

In this conversation, you’ll learn:

1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it)

2. Why following product “best practices” perfectly can actually accelerate your path to unemployment

3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant

4. How to push back on executives without saying “no” (the options, plus a recommendation framework)

5. The counterintuitive reason why the happiest PMs are also the most commercially minded

6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management

—

Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny

Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/

—

Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation

—

Where to find Matt LeMay:

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

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

• Website: https://mattlemay.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 Matt LeMay

(04:23) Matt’s background and transition to product management

(06:47) The goal of Matt's new book

(12:00) How to stress test your thinking as a PM

(15:32) Thinking like the CEO

(17:33) The role of a product manager

(23:36) The low-impact PM death spiral

(27:47) Case study: Mailchimp’s transition to a platform company

(32:53) Radical acceptance

(41:24) Embracing constraints in product management

(44:23) Steps to become an impact-first product team

(49:38) Setting effective goals

(01:02:15) Prioritization and impact estimation

(01:07:58) Navigating stakeholder management

(01:12:35) Summarizing the 3 steps

(01:16:36) Lightning round and final thoughts

—

Referenced:

• Pitchfork: https://pitchfork.com/

• Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/

• How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy

• Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri

• Mailchimp: https://mailchimp.com/

• Intuit: https://www.intuit.com/

• Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/

• The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina

• Miro: https://miro.com/

• Prioritizing: https://www.lennysnewsletter.com/p/prioritizing

• Temptation Island on Netflix: https://www.netflix.com/title/81744518

• Mark L. Walberg’s website: https://markwalbergtv.com/about

• Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/

• Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp

• Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/

• Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/

• RedMonk: https://redmonk.com/

—

Recommended books:

• Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r

• Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ

• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/

• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028

• The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched.

We discuss:

1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”)

2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied

3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity

4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more

5. The accidental decisions that changed history, including not having a waitlist

6. The impact ChatGPT will have on SEO and product growth

7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection

8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown

9. How TikTok comments became a primary user research channel early on

—

Brought to you by:

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

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

PostHog—How developers build successful products: https://posthog.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation

—

Where to find Nick Turley

• X: https://x.com/nickaturley

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

• Website: https://nickturley.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 Nick Turley

(04:52) GPT-5 launch

(09:13) The vision for ChatGPT and AI assistants

(13:52) The early days of ChatGPT

(17:14) The success and impact of ChatGPT

(20:44) Product development and iteration

(23:11) Maximally accelerated: the OpenAI approach

(26:17) Retention and user engagement

(33:42) The future of chat interfaces

(36:31) The evolution of ChatGPT

(38:52) Subscription model and pricing strategies

(42:10) Enterprise adoption and challenges

(44:10) Balancing multiple product lines

(52:13) Emergent use cases and user feedback

(01:02:15) OpenAI’s unique product development approach

(01:05:07) The importance of team composition

(01:08:50) Balancing speed and quality in AI development

(01:14:23) The role of evals in product development

(01:16:13) The future of AI-driven content and GPTs

(01:21:51) Philosophy and product leadership

(01:23:47) Career journey and advice

(01:27:49) Lightning round and final thoughts

—

References: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact.

In this conversation, we discuss:

1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful

2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s

3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner

4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence)

5. His framework for navigating midlife transitions and finding meaning after 40

6. Specific tactics for older professionals to thrive in tech companies

7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond

8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes)

—

Brought to you by:

Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

Coda—The all-in-one collaborative workspace: https://coda.io/lenny

—

Transcript: https://www.lennysnewsletter.com/p/chip-conley

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation

—

Where to find Chip Conley:

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

• Website: https://chipconley.com/

• Modern Elder Academy: https://www.meawisdom.com/

• Podcast: https://www.meawisdom.com/podcast/

—

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 Chip Conley

(04:09) Chip’s journey with Airbnb

(10:35) Insights on working with Brian Chesky

(19:56) The value of intergenerational collaboration

(25:57) Addressing ageism in tech

(41:33) Chip’s early career and founding Joie de Vivre

(43:54) A life-changing near-death experience

(46:39) The importance of company culture

(55:57) The Modern Elder Academy

(59:21) The upside of aging

(01:06:53) AI in daily life

(01:09:14) Lightning round and final thoughts

—

Referenced:

• Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/

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

• Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/

• Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/

• How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making

• George Tenet: https://en.wikipedia.org/wiki/George_Tenet

• Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US

• Fest300: https://en.wikipedia.org/wiki/Fest300

• John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/

•Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html

• Burning Man: https://burningman.org/

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter)

• Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs

• Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile

• Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/

• Becca Levy’s website: https://becca-levy.com/

• Kabuki Springs & Spa: https://kabukisprings.com/

• How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca

• The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/

• The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/

• Four Seasons: https://www.fourseasons.com/

• Blue Zones: https://www.bluezones.com/

• The Esalen Institute: https://www.esalen.org/

• Wisdom Well blog: https://www.meawisdom.com/wisdom-well/

• Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius

• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

• I’ll Push You: https://www.illpushyou.com/

• Vuori shorts: https://vuoriclothing.com/collections/shorts

• Fly Ranch: https://flyranch.burningman.org/

—

Recommended books:

• Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902

• Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484

• Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618

• Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027

• Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/

• Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/

• Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member.

In this conversation, you’ll learn:

1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps

2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role

3. The three AI market segments that matter

4. Why AI agents will replace SaaS products

5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama

6. The counterintuitive go-to-market strategy most AI startups get wrong

7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it)

8. What he’s teaching his kids about AI that every parent should know

—

Brought to you by:

CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny

Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny

Vanta—Automate compliance. Simplify security: https://vanta.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation

—

Where to find Bret Taylor:

• X: https://x.com/btaylor

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

—

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 Bret Taylor

(04:10) Bret’s early career and first major mistake

(08:24) The birth of Google Maps

(11:57) Lessons from FriendFeed and the importance of honest feedback

(31:30) The future of coding and AI’s role

(45:26) Preparing the next generation for an AI-driven world

(48:46) AI in education

(52:05) Business strategies in the AI market

(01:04:38) Outcome-based pricing in AI

(01:09:15) Productivity gains and AI

(01:17:35) Go-to-market strategies for AI products

(01:21:49) Lightning round and final thoughts

—

Referenced:

• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/

• “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98

• Quip: https://quip.com/

• Sierra: https://sierra.ai/

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

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/

• Paul Buchheit on X: https://x.com/paultoo

• Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/

• Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama

• Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey

• Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher

• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia

• Sam Altman on X: https://x.com/sama

• Warren Buffett on X: https://x.com/warrenbuffett

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

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

• C: https://en.wikipedia.org/wiki/C_(programming_language)

• Python: https://www.python.org/

• Perl: https://www.perl.org/

• Rust: https://www.rust-lang.org/

• Eleven Labs: https://elevenlabs.io/

• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack

• Confluent: https://www.confluent.io/

• Databricks: https://www.databricks.com/

• Snowflake: https://www.snowflake.com

• Harvey: https://www.harvey.ai/

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Larry Summers’s website: https://larrysummers.com/

• AutoCAD: https://www.autodesk.com/products/autocad/overview

• Revit: https://www.autodesk.com/products/revit/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

• Cursor: https://cursor.com/

• CodeX: https://openai.com/codex/

• Claude Code: https://www.anthropic.com/claude-code

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

• DirecTV: https://www.directv.com/

• SiriusXM: https://www.siriusxm.com/

• Wayfair: https://www.wayfair.com/

• Akai: https://www.akaipro.com/

• Chubbies Shorts: https://www.chubbiesshorts.com/

• Weight Watchers: https://www.weightwatchers.com/

• CLEAR: https://www.clearme.com/

• Stripe: https://stripe.com/

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

• Twilio: https://www.twilio.com/

• ServiceNow: https://www.servicenow.com/

• Adobe: https://www.adobe.com/

• Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Inception: https://www.imdb.com/title/tt1375666/

• Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831

• Jobs at Sierra: https://sierra.ai/careers

—

Recommended books:

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612

• Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies.

In this conversation, we discuss:

1. The 2x2 framework that identifies your optimal pricing model

2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products

3. Why popular AI coding tools may have already doomed themselves with underpricing

4. The “give-and-get” framework top negotiators use to extract maximum value from every deal

5. The negotiation strategy that helped one founder 4x their deal size overnight

6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)

7. Why AI companies must get monetization right from day one—not “figure it out later”

8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)

9. The single question that reveals if your pricing is too complex

—

Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation

—

Where to find Madhavan Ramanujam:

• X: https://x.com/madhavansf

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

• Promo email for Scaling Innovation: promo@49palmsvc.com — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle.

—

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 Madhavan and his work

(04:30) The core thesis of Scaling Innovation

(09:20) Common traps founders fall into

(12:06) Beautifully simple pricing

(15:00) Mastering negotiations

(26:51) Other strategies for effective pricing and monetization

(27:35) How AI pricing is different

(31:33) Handling POCs

(36:25) The importance of mastering monetization

(38:58) Choosing the right AI pricing model

(43:13) Current trends in AI pricing

(44:48) Strategizing for outcome-based models

(50:23) Packaging strategies for scaling

(51:37) Adapting pricing strategies over time

(53:40) Key axioms for pricing success

(58:00) Takeaways for founders

(01:01:33) Lightning round and final thoughts

—

Referenced:

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Cursor: https://www.cursor.com/

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

• Sierra Finn: http://www.sierrafinn.com/

• Chargeflow: https://www.chargeflow.io/

• GitHub: https://github.com/

• Intercom: https://www.intercom.com/

• Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing

• Sierra: https://sierra.ai/

• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/

• Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/

• Delphi: https://www.delphi.ai/

• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/

• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/

• Lennybot: https://www.lennybot.com/

• Granola: https://www.granola.ai/

• Simon-Kucher: https://www.simon-kucher.com/

• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/

—

Recommended books:

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060

• Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417

• Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

• Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly.

In this conversation, we discuss:

1. The inside story of leaving OpenAI with the entire safety team to start Anthropic

2. How Meta’s $100M offers reveal the true market price of top AI talent

3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential

4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028

5. Why he believes 20% unemployment is inevitable

6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them

7. How focusing on AI safety created Claude’s beloved personality

8. What three skills he’s teaching his kids instead of traditional academics

—

Brought to you by:

Sauce—Turn customer pain into product revenue: https://sauce.app/lenny

LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny

Fin—The #1 AI agent for customer service: https://fin.ai/lenny

—

Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation

—

Where to find Ben Mann:

• X: https://x.com/8enmann

• LinkedIn: https://www.linkedin.com/in/benjamin-mann/

• Website: https://benjmann.net/

—

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 Benjamin

(04:43) The AI talent war

(06:28) AI progress and scaling laws

(10:50) Defining AGI and the economic Turing test

(12:26) The impact of AI on jobs

(17:45) Preparing for an AI future

(24:05) Founding Anthropic

(27:06) Balancing AI safety and progress

(29:10) Constitutional AI and model alignment

(34:21) The importance of AI safety

(43:40) The risks of autonomous agents

(45:40) Forecasting superintelligence

(48:36) How hard is it to align AI?

(53:19) Reinforcement learning from AI feedback (RLAIF)

(57:03) AI's biggest bottlenecks

(01:00:11) Personal reflections on responsibilities

(01:02:36) Anthropic’s growth and innovations

(01:07:48) Lightning round and final thoughts

—

Referenced:

• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/

• Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs

• Alexa+: https://www.amazon.com/dp/B0DCCNHWV5

• Azure: https://azure.microsoft.com/

• Sam Altman on X: https://x.com/sama

• Opus 3: https://www.anthropic.com/news/claude-3-family

• Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution

• Greg Brockman on X: https://x.com/gdb

• Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy

• Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment

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

• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff

• Unitree: https://www.unitree.com/

• Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke

• How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works

• RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback

• Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/

• Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law

• Machine Intelligence Research Institute: https://intelligence.org/

• Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/

• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question

• Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/

• “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question

• Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard

• Pantheon on Netflix: https://www.netflix.com/title/81937398

• Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy

• Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q

• 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651

—

Recommended books:

• Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834

• The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551

• Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q

• Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239

• The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work.

Learn:

1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S.

2. The most underrated AI tool for non-programmers

3. An inside look at Every’s AI-first workflow

4. Why every company needs an “AI operations lead”

5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths

6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools

7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools

—

Brought to you by:

CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny

DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny

PostHog—How developers build successful products: https://posthog.com/lenny

—

Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper

—

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation

—

Where to find Dan Shipper:

• X: https://x.com/danshipper

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

• Podcast: https://every.to/podcast

—

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) Welcome and introduction

(04:04) Hot takes on AI and job reshoring

(07:06) The power of Claude Code for non-coders

(14:35) The future of AI in business operations

(18:45) AI’s role in enhancing human skills

(22:26) The evolution of AI tools and their applications

(25:40) Building an AI-first company

(29:50) Innovative AI operations and team dynamics

(35:35) Dan's AI stack

(41:26) Compounding engineering

(48:29) The impact of AI on learning and development

(50:10) Accelerating career growth with AI

(51:36) Revolutionizing code review and workflow

(53:07) The importance of coding knowledge

(57:26) Building AI-driven products

(01:02:01) Innovative fundraising strategies

(01:08:45) Consulting and AI adoption in companies

(01:17:01) The allocation economy and future skills

(01:20:12) The value of generalists in the AI age

(01:24:07) Lightning round and final thoughts

—

Referenced:

• Claude Code: https://www.anthropic.com/claude-code

• Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/

• Microsoft Copilot: https://copilot.microsoft.com/

• Cursor: https://www.cursor.com/

• Base44: https://base44.com/

• Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo

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

• Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/

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

• Granola: https://www.granola.ai/

• Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• Every: https://every.to/

• Cora: https://www.cora.computer/

• Sparkle: https://makeitsparkle.co/

• Spiral: https://spiral.computer/

• Lex: https://lex.page/

• Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/

• Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/

• Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/

• Animalz: https://www.animalz.co/

• Rachel Woods on X: https://x.com/rachel_l_woods

• Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga

• Claude Opus 4: https://www.anthropic.com/claude/opus

• Codex: https://openai.com/index/introducing-codex/

• Superwhisper: https://superwhisper.com/

• Wispr Flow: https://wisprflow.ai/

• Notion: https://www.notion.com/

• Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/

• Friday: https://www.friday.run/

• Charlie: https://www.gocharlie.ai/product/ai-agents/

• Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe)

• Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/

• Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/

• Dia: https://www.diabrowser.com/

• Reid Hoffman’s website: https://www.reidhoffman.org/

• Starting Line VC: https://www.startingline.vc/

• Walleye Capital: https://walleyecapital.com/

• At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory

• Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514

• Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/

• The Pin Factory: https://www.adamsmithworks.org/pin_factory.html

• Deadwood on HBO: https://www.hbo.com/deadwood

• Joel Spolsky on X: https://x.com/spolsky

• Jason Fried’s website: https://world.hey.com/jason

• Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking

• Sam Harris’s website: https://www.samharris.org/

• Bill Simmons on X: https://x.com/billsimmons

—

Recommended books:

• War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985

• Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002

• Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464

• The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315

• A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022

• The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.