Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor.

We discuss:

1. The complete AI workflow that lets non-technical people build real products in Cursor

2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI)

3. Using slash commands to automate prompts

4. Zevi?s ?peer review? technique, which uses different AI models to review each other?s code

5. Why this might be the best time to be a junior in tech, despite the challenging job market

6. How Zevi used AI to prepare for his Meta PM interviews

?

Brought to you by:

10Web?Vibe coding platform as an API

DX?The developer intelligence platform designed by leading researchers

Framer?Build better websites faster

?

Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor

?

Archive of all Lenny's Podcast transcripts:

https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

?

Where to find Zevi Arnovitz

? X: https://x.com/ArnovitzZevi

? LinkedIn: https://www.linkedin.com/in/zev-arnovitz

? Website: https://zeviarnovitz.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 Zevi Arnovitz

(04:48) Zevi?s background and journey into AI

(07:41) Overview of Zevi?s AI workflow

(14:41) Screenshare: Exploring Zevi?s workflow in detail

(17:18) Building a feature live: StudyMate app

(30:52) Executing the plan with Cursor

(38:32) Using multiple AI models for code review

(40:40) Personifying AI models

(43:37) Peer review process

(45:40) The importance of postmortems

(51:05) Integrating AI in large companies

(53:42) How AI has impacted the PM role

(57:02) How to improve AI outputs

(58:15) AI-assisted job interviews

(01:02:57) Failure corner

(01:06:20) Lightning round and final thoughts

?

Referenced:

? Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv

? Wix: https://www.wix.com

? Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w

? Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw

? Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg

? Bolt: https://bolt.new

? 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

? Lovable: https://lovable.dev

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

? StudyMate: https://studymate.live

? Dibur2text: https://dibur2text.app

? Claude: https://claude.ai

? Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code

? Bun: https://bun.com

? Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction

? 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

? Wispr Flow: https://wisprflow.ai

? Linear: https://linear.app

? 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

? Cursor Composer: https://cursor.com/blog/composer

? 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

? 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

? v0: https://v0.app

? 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

? Cursor Browser mode: https://cursor.com/docs/agent/browser

? Google Antigravity: https://antigravity.google

? Grok: https://grok.com

? Zapier: https://zapier.com

? Airtable: https://www.airtable.com

? Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system

? The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81

? AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08

? Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf

? The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD

? Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

? Loom: https://www.loom.com

? Cap: https://cap.so

? Supercut: https://supercut.ai

...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor

?

Recommended books:

? The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153

? Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910

? Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322

?

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

?

Lenny may be an investor in the companies discussed.

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who?s now teaching etiquette to Silicon Valley?s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026?especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to ?show up in a room with a low heart rate? and quickly build trust.

We discuss:

1. Why etiquette matters

2. Sam?s framework for showing up confidently, with a low heart rate, in any room

3. How to navigate introductions, small talk, meetings, and meals like a pro

4. Simple hacks for remembering names and handling awkward social situations

5. 30+ specific etiquette tips

?

Brought to you by:

10Web?Vibe-coding platform as an API

DX?The developer intelligence platform designed by leading researchers

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

?

Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook

?

Archive of all Lenny's Podcast transcripts:

https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

?

Where to find Sam Lessin:

? X: https://x.com/lessin

? LinkedIn: https://www.linkedin.com/in/wlessin

? Website: https://www.wlessin.com

? Podcast: https://moreorlesspod.com

? Lettermeme: https://lettermeme.com/lessin

?

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) Sam?s background

(04:18) The role of etiquette in business success

(09:30) Introductions and entering a room

(16:20) Engaging conversations and building relationships

(23:55) Hygiene and dress code essentials

(33:42) Dining etiquette

(37:15) Tipping etiquette

(41:36) The ?B&D trick?

(43:05) Humor in social settings

(45:18) Self-deprecating humor

(47:42) Winding down conversations

(49:20) Scheduling etiquette

(55:23) Communication and email etiquette

(01:02:28) Meeting etiquette tips

(01:04:03) Virtual meeting best practices

(01:05:15) The importance of cleaning up after yourself

(01:05:58) Exiting and follow-up etiquette

(01:07:24) Final thoughts

(01:09:20) AI corner

(01:11:13) Contrarian corner

(01:16:25) Lightning round

?

Referenced:

? Y Combinator: https://www.ycombinator.com

? Kleiner Perkins: https://www.kleinerperkins.com

? ?Lose Yourself? by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq

? Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik

? Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan

? Bain & Company: https://www.bain.com

? Evernote: https://evernote.com

? Calendly: https://calendly.com

? Morning Brew: https://www.morningbrew.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

? DigitalOcean: https://www.digitalocean.com

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

? SpaceX: https://www.spacex.com

? Marc Andreessen on X: https://x.com/pmarca

? Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD

? Dave Morin on X: https://x.com/davemorin

?

Recommended books:

? Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5

? Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A

? The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048

? Man?s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI

? Area 51: An Uncensored History of America?s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q

? The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X

? The Fish That Ate the Whale: The Life and Times of America?s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314

? The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439

?

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

?

Lenny may be an investor in the companies discussed.

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they?ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering.

We discuss:

1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built

2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle

3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement

4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products

5. Why evals aren?t a cure-all, and the most common misconceptions people have about them

6. The skills that matter most for builders in the AI era

?

Brought to you by:

Merge?The fastest way to ship 220+ integrations: https://merge.dev/lenny

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

Brex?The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs

?

Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced

?

Get 15% off Aishwarya and Kiriti?s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp

?

Where to find Aishwarya Naresh Reganti:

? LinkedIn: https://www.linkedin.com/in/areganti

? GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide

? X: https://x.com/aish_reganti

?

Where to find Kiriti Badam:

? LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam

? X: https://x.com/kiritibadam

?

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 Aishwarya and Kiriti

(05:03) Challenges in AI product development

(07:36) Key differences between AI and traditional software

(13:19) Building AI products: start small and scale

(15:23) The importance of human control in AI systems

(22:38) Avoiding prompt injection and jailbreaking

(25:18) Patterns for successful AI product development

(33:20) The debate on evals and production monitoring

(41:27) Codex team?s approach to evals and customer feedback

(45:41) Continuous calibration, continuous development (CC/CD) framework

(58:07) Emerging patterns and calibration

(01:01:24) Overhyped and under-hyped AI concepts

(01:05:17) The future of AI

(01:08:41) Skills and best practices for building AI products

(01:14:04) Lightning round and final thoughts

?

Referenced:

? LevelUp Labs: https://levelup-labs.ai/

? Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different

? Booking.com: https://www.booking.com

? Research paper on agents in production (by Matei Zaharia?s lab): https://arxiv.org/pdf/2512.04123

? Matei Zaharia?s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en

? The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

? Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah

? Rackspace: https://www.rackspace.com

? 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

? Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html

? LMArena: https://lmarena.ai

? Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers

? Why humans are AI?s biggest bottleneck (and what?s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck

? Airline held liable for its chatbot giving passenger bad advice?what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know

? Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis

? We replaced our sales team with 20 AI agents?here?s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

? Socrates?s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living

? Noah Smith?s newsletter: https://www.noahpinion.blog

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

? Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/

? Wisprflow: https://wisprflow.ai

? Raycast: https://www.raycast.com

? Steve Jobs?s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only

?

Recommended books:

? ?When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X

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

? A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285

?

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

?

Lenny may be an investor in the companies discussed.

Molly Graham has worked for some of tech?s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She?s best known for her ?Give away your Legos? framework and her collection of practical mental models for leading through hypergrowth.

We discuss:

1. ?Give away your Legos?: a framework for scaling yourself as a leader

2. ?J-curves vs. stairs?: the two paths of career growth, and why you should pick the scarier path

3. ?The waterline model? for diagnosing team problems (and why you should ?snorkel before you scuba?)

4. Six rules for creating effective goals (and aligning everyone around them)

5. Rules of thumb for leading through rapid scale and change

6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor

?

Brought to you by:

DX?The developer intelligence platform designed by leading researchers

Brex?The banking solution for startups

GoFundMe Giving Funds?Make helping a habit

?

Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation

?

Where to find Molly Graham:

? X: https://x.com/molly_g

? LinkedIn: https://www.linkedin.com/in/mograham

? Substack: https://mollyg.substack.com

? Website: https://glueclub.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 Molly Graham

(04:28) Molly?s background at Google, Facebook, Quip, and CZI

(11:29) The ?Give away your Legos? framework

(16:44) Managing your inner monster

(19:49) When not to give away your Legos

(21:28) Embracing a long career

(23:25) The J-curve vs. stairs approach to career growth

(32:00) The gift of knowing yourself

(34:28) Learning to be a professional idiot

(38:30) The waterline model: snorkel before you scuba

(47:16) Six rules for creating strong alignment around goals

(57:15) Rules of thumb for leading through rapid scale

(01:07:49) Investing in high performers vs. low performers

(01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor

(1:21:15) Pivoting from ambition to purpose

(1:26:32) Finding stability in instability

(01:29:44) Final thoughts

?

Referenced:

? Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

? Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

? Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage

? Quip: https://quip.com

? 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

? Chan Zuckerberg Initiative: https://chanzuckerberg.com

? 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

? ?Give Away Your Legos? and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups

? The Muppets: https://muppets.disney.com

? Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell

? J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve

? Forget the corporate ladder?winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks

? Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath

? Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921

? Joseph Campbell?s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you

? Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz

? Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model

? Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc

? I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about

? Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

? James Clear?s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals

? Founder mode: https://paulgraham.com/foundermode.html

? Stripe: https://stripe.com

? Patrick Collison on X: https://www.linkedin.com/in/patrickcollison

? John Collison on X: https://x.com/collision

? Seth Godin?s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

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

?

Recommended books:

? The Artist?s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252

? Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

? Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

?

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

?

Lenny may be an investor in the companies discussed.

Jason Lemkin is the founder of SaaStr, the world?s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn?t, and how the GTM landscape is quickly being transformed.

We discuss:

1. How AI is fundamentally changing the sales function

2. Why most SDRs and BDRs will be ?extinct? within a year

3. What Jason is observing across his portfolio about AI adoption in GTM

4. How to become ?hyper-employable? in the age of AI

5. The specific AI tools and tactics he?s using that have been working best

6. Practical frameworks for integrating AI into your sales motion without losing what works

7. Jason?s 2026 predictions on where SaaS and GTM are heading next

?

Brought to you by:

DX?The developer intelligence platform designed by leading researchers

Vercel?Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web

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

?

Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation

?

Where to find Jason Lemkin:

? X: https://x.com/jasonlk

? LinkedIn: https://www.linkedin.com/in/jasonmlemkin

? Website: https://www.saastr.com

? Substack: https://substack.com/@cloud

?

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 Lemkin

(04:36) What SaaStr does

(07:13) AI?s impact on sales teams

(10:11) How SaaStr's AI agents work and their performance

(14:18) How go-to-market is changing in the AI era

(19:19) The future of SDRs, BDRs, and AEs in sales

(22:03) Why leadership roles are safe

(23:43) How to be in the 20% who thrive in the AI sales future

(28:40) Why you shouldn't build your own AI tools

(30:10) Specific AI agents and their applications

(36:40) Challenges and learnings in AI deployment

(42:11) Making AI-generated emails good (not just acceptable)

(47:31) When humans still beat AI in sales

(52:39) An overview of SaaStr's org

(53:50) The role of human oversight in AI operations

(58:37) Advice for salespeople and founders in the AI era

(01:05:40) Forward-deployed engineers

(01:08:08) What's changing and what's staying the same in sales

(01:16:21) Why AI is creating more work, not less

(01:19:32) Why Jason says these are magical times

(01:25:25) The "incognito mode test" for finding AI opportunities

(01:27:19) The impact of AI on jobs

(01:30:18) Lightning round and final thoughts

?

Referenced:

? Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

? SaaStr Annual: https://www.saastrannual.com

? Delphi: https://www.delphi.ai/saastr/talk

? Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/

? Vercel: https://vercel.com

? What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently

? 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

? ElevenLabs: 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

? Bolt: https://bolt.new

? Lovable: https://lovable.dev

? Harvey: https://www.harvey.ai

? Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence

? UiPath: https://www.uipath.com

? Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser

? Agentforce: https://www.salesforce.com/form/agentforce

? SaaStr?s AI Agent Playbook: https://saastr.ai/agents

? Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan

? Brian Halligan?s AI: https://www.delphi.ai/minds/bhalligan

? Sierra: https://sierra.ai

? Fin: https://fin.ai

? Deccan: https://www.deccan.ai

? Artisan: https://www.artisan.co

? Qualified: https://www.qualified.com

? Claude: https://claude.ai

? HubSpot: https://www.hubspot.com

? Gamma: https://gamma.app

? Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b

? Brex: https://www.brex.com

? Outreach: https://www.outreach.io

? Gong: https://www.gong.io

? Salesloft: https://www.salesloft.com

? Mixmax: https://www.mixmax.com

? ?Sell the alpha, not the feature?: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr

? Clay: https://www.clay.com

? Owner: https://www.owner.com

? Momentum: https://www.momentum.io

? Attention: https://www.attention.com

? Granola: https://www.granola.ai

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

? Palantir: https://www.palantir.com

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

? Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan

? Rippling: https://www.rippling.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

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

? Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza

? Sora: https://openai.com/sora

? Reve: https://app.reve.com

? Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/

? The Revenue Playbook: Rippling?s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw

? 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

?

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

?

Lenny may be an investor in the companies discussed.

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.

We discuss:

1. Why ?extraordinary results demand extraordinary efforts?

2. Why you should deliberately understaff projects, and how to know when you?ve gone too far

3. Matt?s transition from COO to CPO and what surprised him about leading product

4. The ?high alpha, low beta? framework for evaluating people, processes, and products

5. When founders should quit their startups (hint: much earlier than VCs want you to)

6. How to fight entropy in your organization through relentless energy and intensity

?

Brought to you by:

Google Gemini?Your everyday AI assistant: https://ai.dev/

Datadog?Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

GoFundMe Giving Funds?Make year-end giving easy: http://gofundme.com/lenny

?

Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation

?

Where to find Matt MacInnis:

? X: https://x.com/stanine

? LinkedIn: https://www.linkedin.com/in/macinnis

? Email: [email protected]

?

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 MacInnis and Rippling

(04:38) The importance of extraordinary efforts

(08:37) The challenges and rewards of relentless effort

(10:11) Your job as a leader is to preserve intensity

(12:39) You learn far more from success than failure

(16:34) Transitioning to chief product officer

(19:54) Fixing product management at Rippling

(25:27) The ?high alpha, low beta? framework

(28:55) The PQL framework

(35:16) Hiring frameworks and team dynamics

(36:52) A helpful interview tactic

(40:00) Leading as a COO vs. a CPO

(42:34) The reality of product-market fit

(46:38) The problem with venture capital

(49:29) When founders should quit their startups

(41:48) The immutable market

(54:13) Lessons from Notion?s success

(57:43) Investment strategies and narrative violations

(01:00:42) The power of compounding, power law, and entropy

(01:07:02) Maintaining intensity and fighting entropy

(01:11:33) The importance of feedback and escalations

(01:14:31) Rippling?s vision and success

(01:17:48) AI?s impact on SaaS and business software

(01:23:42) AI corner

(01:26:23) Final thoughts and lightning round

?

Referenced:

? Rippling: https://www.rippling.com

? Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman

? Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill

? Carvana: https://www.carvana.com

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

? Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad

? Inkling: https://www.inkling.com

? Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari

? Notion: https://www.notion.com

? Conway?s law: https://en.wikipedia.org/wiki/Conway%27s_law

? Seeking Alpha: https://seekingalpha.com

? Dennis Rodman?s website: https://dennisrodman.com

? Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle

? Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick

? SPOTAK: The Six Traits I Look for When I?m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html

? Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1

? Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits

? New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling

? Workday: https://www.workday.com

? Matic robots: https://maticrobots.com

? Wall-E: https://www.imdb.com/title/tt0910970

? Conviction: https://www.conviction.com

? Mike Vernal on X: https://x.com/mvernal

? Sarah Guo on X: https://x.com/saranormous

? No Priors: https://linktr.ee/nopriors

? Gemini: https://gemini.google.com

? ChatGPT: https://chatgpt.com

? Claude: https://claude.ai

? Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier

? Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c

? Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker

?

Recommended books:

? Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595

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

? Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

? The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459

?

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

?

Lenny may be an investor in the companies discussed.

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he?s spent more time than anyone alive studying how attackers break AI systems, and what he?s found isn?t reassuring: the guardrails companies are buying don?t actually work, and we?ve been lucky we haven?t seen more harm so far, only because AI agents aren?t capable enough yet to do real damage.

We discuss:

1. The difference between jailbreaking and prompt injection attacks on AI systems

2. Why AI guardrails don?t work

3. Why we haven?t seen major AI security incidents yet (but soon will)

4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages

5. The practical steps organizations should take instead of buying ineffective security tools

6. Why solving this requires merging classical cybersecurity expertise with AI knowledge

?

Brought to you by:

Datadog?Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

Metronome?Monetization infrastructure for modern software companies: https://metronome.com/

GoFundMe Giving Funds?Make year-end giving easy: http://gofundme.com/lenny

?

Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation

?

Where to find Sander Schulhoff:

? X: https://x.com/sanderschulhoff

? LinkedIn: https://www.linkedin.com/in/sander-schulhoff

? Website: https://sanderschulhoff.com

? AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC

?

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 Sander Schulhoff and AI security

(05:14) Understanding AI vulnerabilities

(11:42) Real-world examples of AI security breaches

(17:55) The impact of intelligent agents

(19:44) The rise of AI security solutions

(21:09) Red teaming and guardrails

(23:44) Adversarial robustness

(27:52) Why guardrails fail

(38:22) The lack of resources addressing this problem

(44:44) Practical advice for addressing AI security

(55:49) Why you shouldn?t spend your time on guardrails

(59:06) Prompt injection and agentic systems

(01:09:15) Education and awareness in AI security

(01:11:47) Challenges and future directions in AI security

(01:17:52) Companies that are doing this well

(01:21:57) Final thoughts and recommendations

?

Referenced:

? 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

? The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit

? The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

? OpenAI: https://openai.com

? Scale: https://scale.com

? Hugging Face: https://huggingface.co

? Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642

? Simon Willison?s Weblog: https://simonwillison.net

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

? ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html

? Alex Komoroske on X: https://x.com/komorama

? Twitter pranksters derail GPT-3 bot with newly discovered ?prompt injection? hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack

? MathGPT: https://math-gpt.org

? 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion

? Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage

? Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

? Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133

? MATS Research: https://substack.com/@matsresearch

? CBRN: https://en.wikipedia.org/wiki/CBRN_defense

? CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel

? Trustible: https://trustible.ai

? Repello: https://repello.ai

? Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks

?

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

?

Lenny may be an investor in the companies discussed.

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they?ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy.

We discuss:

1. Why 60% to 70% of traditional growth tactics no longer apply in AI

2. Why you have to re-find product-market fit every 3 months

3. The specific growth tactics driving Lovable?s unprecedented growth

4. Why giving away product is a growth strategy that beats paid ads

5. ?Minimum lovable product? as the new standard (not minimum viable product)

6. Why activation now belongs to product teams, not growth teams

7. Whether you should join an AI startup (honest tradeoffs)

?

Brought to you by:

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

Vercel?Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web

Persona?A global leader in digital identity verification

?

Transcript: ?https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna?

?

My biggest takeaways (for paid newsletter subscribers): ?https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation?

?

Where to find Elena Verna:

? X: https://x.com/elenaverna

? LinkedIn: https://www.linkedin.com/in/elenaverna

? Newsletter: https://www.elenaverna.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 Elena Verna

(05:19) The scale and growth of Lovable

(08:55) Confidence in Lovable as a business

(12:17) Retention at Lovable

(15:02) Lovable?s unique growth levers

(28:13) The role of marketing in Lovable?s success

(38:09) Launching new features

(40:59) Hiring and team dynamics

(43:17) The value of vibe coding

(49:46) The importance of community

(51:47) Giving away your product for free

(56:26) Tripling their company size

(01:00:23) Product-market-fit challenges

(01:08:50) Advice for joining AI companies

(01:12:00) Work-life balance

(01:15:20) What it?s like to work at Lovable

(01:19:45) Women in tech

(01:25:29) Final thoughts and lightning round

?

Referenced:

? Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company

? The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led

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

? Lovable: https://lovable.dev

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

? Stripe: https://stripe.com

? What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing

? How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can?t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

? ?Dumbest idea I?ve heard? to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn

? Eric Ries on LinkedIn: https://www.linkedin.com/in/eries

? Elena?s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e

? SheBuilds: https://shebuilds.lovable.app

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

? The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill

? 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

? Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba

? The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user

? Granola: https://www.granola.ai

? Wispr Flow: https://wisprflow.ai

? I?m worried about women in tech: https://www.elenaverna.com/p/im-worried-about-women-in-tech

? Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

?

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

?

Lenny may be an investor in the companies discussed.

Alexander Embiricos leads product on Codex, OpenAI?s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate?an AI agent designed to participate across the entire development lifecycle.

We discuss:

1. Why Codex has grown 20x since launch and what product decisions unlocked this growth

2. How OpenAI built the Sora Android app in just 18 days using Codex

3. Why the real bottleneck to AGI-level productivity isn?t model capability?it?s human typing speed

4. The vision of AI as a proactive teammate, not just a tool you prompt

5. The bottleneck shifting from building to reviewing AI-generated work

6. Why coding will be a core competency for every AI agent?because writing code is how agents use computers best

?

Brought to you by:

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

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

?

Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation

?

Where to find Alexander Embiricos:

? X: https://x.com/embirico

? LinkedIn: https://www.linkedin.com/in/embirico

?

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 Alexander Embiricos 

(05:13) The speed and ambition at OpenAI

(11:34) Codex: OpenAI?s coding agent

(15:43) Codex?s explosive growth

(24:59) The future of AI and coding agents

(33:11) The impact of AI on engineering

(44:08) How Codex has impacted the way PMs operate

(45:40) Throwaway code and ubiquitous coding

(47:10) Shipping the Sora Android app

(49:01) Building the Atlas browser

(53:34) Codex?s impact on productivity

(55:35) Measuring progress on Codex

(58:09) Why they are building a web browser

(01:01:58) Non-engineering use cases for Codex

(01:02:53) Codex?s capabilities

(01:04:49) Tips for getting started with Codex

(01:05:37) Skills to lean into in the AI age

(01:10:36) How far are we from a human version of AI?

(01:13:31) Hiring and team growth at Codex

(01:15:47) Lightning round and final thoughts

?

Referenced:

? OpenAI: https://openai.com

? Codex: https://openai.com/codex

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

? Dropbox: http://dropbox.com

? Datadog: https://www.datadoghq.com

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

? 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

? Atlas: https://openai.com/index/introducing-chatgpt-atlas

? How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native

? Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose

? Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense

? Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1

? The OpenAI Podcast?ChatGPT Atlas and the next era of web browsing: https://www.youtube.com/watch?v=WdbgNC80PMw&list=PLOXw6I10VTv9GAOCZjUAAkSVyW2cDXs4u&index=2

? How to measure AI developer productivity in 2025 | Nicole Forsgren: https://www.lennysnewsletter.com/p/how-to-measure-ai-developer-productivity

? Compiling: https://3d.xkcd.com/303

? Jujutsu Kaisen on Netflix: https://www.netflix.com/title/81278456

? Tesla: https://www.tesla.com

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

? Andreas Embirikos: https://en.wikipedia.org/wiki/Andreas_Embirikos

? George Embiricos: https://en.wikipedia.org/wiki/George_Embiricos: https://en.wikipedia.org/wiki/George_Embiricos

?

Recommended books:

? Culture series: https://www.amazon.com/dp/B07WLZZ9WV

? The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411

? A Fire Upon the Deep (Zones of Thought series Book 1): https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/1250237750

? Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

?

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

?

Lenny may be an investor in the companies discussed.

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what?s good vs. what?s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped?the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT.

We discuss:

1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality

2. The story behind how Claude Code got so good at coding and writing

3. The problems with AI benchmarks and why they?re pushing AI in the wrong direction

4. How RL environments are the next frontier in AI training

5. Why Edwin believes we?re still a decade away from AGI

6. Why taste and human judgment shape which AI models become industry leaders

7. His contrarian approach to company building that rejects Silicon Valley?s ?pivot and blitzscale? playbook

8. How AI models will become increasingly differentiated based on the values of the companies building them

?

Brought to you by:

Vanta?Automate compliance. Simplify security.

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

Coda?The all-in-one collaborative workspace

?

Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation

?

Where to find Edwin Chen:

? X: https://x.com/echen

? LinkedIn: https://www.linkedin.com/in/edwinzchen

? Surge?s blog: https://surgehq.ai/blog

?

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 Edwin Chen

(04:48) AI?s role in business efficiency

(07:08) Building a contrarian company

(08:55) An explanation of what Surge AI does

(09:36) The importance of high-quality data

(13:31) How Claude Code has stayed ahead

(17:37) Edwin?s skepticism toward benchmarks

(21:54) AGI timelines and industry trends

(28:33) The Silicon Valley machine

(33:07) Reinforcement learning and future AI training

(39:37) Understanding model trajectories

(41:11) How models have advanced and will continue to advance

(42:55) Adapting to industry needs

(44:39) Surge?s research approach

(48:07) Predictions for the next few years in AI

(50:43) What?s underhyped and overhyped in AI

(52:55) The story of founding Surge AI

(01:02:18) Lightning round and final thoughts

?

Referenced:

? Surge: https://surgehq.ai

? Surge?s product page: https://surgehq.ai/products

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

? Gemini 3: https://aistudio.google.com/models/gemini-3

? Sora: https://openai.com/sora

? Terrence Rohan on LinkedIn: https://www.linkedin.com/in/terrencerohan

? Richard Sutton?Father of RL thinks LLMs are a dead end: https://www.dwarkesh.com/p/richard-sutton

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

? Reinforcement learning: https://en.wikipedia.org/wiki/Reinforcement_learning

? Grok: https://grok.com

? Warren Buffett on X: https://x.com/WarrenBuffett

? 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

? Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong

? Interstellar on Prime Video: https://www.amazon.com/Interstellar-Matthew-McConaughey/dp/B00TU9UFTS

? Arrival on Prime Video: https://www.amazon.com/Arrival-Amy-Adams/dp/B01M2C4NP8

? Travelers on Netflix: https://www.netflix.com/title/80105699

? Waymo: https://waymo.com

? Soda versus pop: https://flowingdata.com/2012/07/09/soda-versus-pop-on-twitter

?

Recommended books:

? Stories of Your Life and Others: https://www.amazon.com/Stories-Your-Life-Others-Chiang/dp/1101972122

? The Myth of Sisyphus: https://www.amazon.com/Myth-Sisyphus-Vintage-International/dp/0525564454

? Le Ton Beau de Marot: In Praise of the Music of Language: https://www.amazon.com/dp/0465086454

? Gödel, Escher, Bach: An Eternal Golden Braid: https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567

?

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

?

Lenny may be an investor in the companies discussed.

Tomer Cohen is the longtime chief product officer at LinkedIn, where he?s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He?s also introduced a formal ?Full Stack Builder? title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less.

We discuss:

1. How 70% of the skills needed for jobs will change by 2030

2. The broken traditional model: organizational bloat slows features to a six-month cycle

3. The Full Stack Builder model

4. Three pillars of making FSB work: platform, agents, and culture (culture matters most)

5. Building specialized agents that critique ideas and find vulnerabilities

6. Why off-the-shelf AI tools never work on enterprise code without customization

7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects

8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews

?

Brought to you by:

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

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

Miro?The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny

?

Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation

?

Where to find Tomer Cohen:

? LinkedIn: https://www.linkedin.com/in/tomercohen

? Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498

?

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 Tomer Cohen

(04:42) The need for change in product development

(11:52) The full-stack builder model explained

(16:03) Implementing AI and automation in product development

(19:17) Building and customizing AI tools

(27:51) The timeline to launch

(31:46) Pilot program and early results

(37:04) Feedback from top talent

(39:48) Change management and adoption

(46:53) Encouraging people to play with AI tools

(41:21) Performance reviews and full-stack builders

(48:00) Challenges and specialization

(50:05) Finding talent

(52:46) Tips for implementing in your own company

(56:43) Lightning round and final thoughts

?

Referenced:

? How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

? LinkedIn: https://www.linkedin.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

? Devin: https://devin.ai

? Figma: https://www.figma.com

? Microsoft Copilot: https://copilot.microsoft.com

? 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 (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

? APB program at LinkedIn: https://careers.linkedin.com/pathways-programs/entry-level/apb

? Naval Ravikant on X: https://x.com/naval

? One Song podcast: https://podcasts.apple.com/us/podcast/%D7%A9%D7%99%D7%A8-%D7%90%D7%97%D7%93-one-song/id1201883177

? Song Exploder podcast: https://songexploder.net

? Grok on Tesla: https://www.tesla.com/support/grok

? Reid Hoffman on X: https://x.com/reidhoffman

?

Recommended books:

? Why Nations Fail: The Origins of Power, Prosperity, and Poverty: https://www.amazon.com/Why-Nations-Fail-Origins-Prosperity/dp/0307719227

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

? The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/Beginning-Infinity-Explanations-Transform-World/dp/0143121359

?

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

?

Lenny may be an investor in the companies discussed.

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe?s early sales organization from the ground up and advises founders on GTM strategy.

We discuss:

1. Why GTM is becoming more strategically important in the AI era

2. The rise of the GTM engineer

3. A primer on segmentation

4. How to build a sales org that engineers and product teams respect

5. The changing calculus of build vs. buy for go-to-market tools in the AI era

6. Why most customers buy to avoid pain rather than to gain upside

?

Brought to you by:

Datadog?Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny

Lovable?Build apps by simply chatting with AI: https://lovable.dev/

Stripe?Helping companies of all sizes grow revenue: https://stripe.com/

?

Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation

?

Where to find Jeanne DeWitt Grosser:

? X: https://x.com/jdewitt29

? LinkedIn: https://www.linkedin.com/in/jeannedewitt

?

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 Jeanne DeWitt Grosser

(05:26) Defining go-to-market

(08:43) The evolution of go-to-market roles

(11:23) The rise of the go-to-market engineer

(14:21) Implementing AI in sales processes

(15:28) Optimizing sales with AI agents

(23:47) Defining sales roles: SDRs and AEs

(26:04) When to hire a GTM engineer

(29:04) Hiring and scaling sales teams

(30:50) The ideal go-to-market engineer

(34:24) The go-to-market tool stack

(40:39) Advice on building a great sales bot

(44:34) Vercel?s unfair advantage

(46:37) Go-to-market as a product

(47:04) Innovative sales tactics at Stripe

(52:38) Effective go-to-market tactics

(01:00:37) Segmentation strategies

(01:09:31) Building a sales org that engineers love

(01:14:00) Thoughts on PLG and pricing

(01:16:44) Sales compensation and hiring

(01:19:24) Lightning round and final thoughts

?

Referenced:

? Vercel: https://vercel.com

? Stripe: https://stripe.com

? Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin

? Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman

? SDK: https://ai-sdk.dev/docs/introduction

? Gong: https://www.gong.io

? Lyft: https://www.lyft.com

? Instacart: https://www.instacart.com

? DoorDash: https://www.instacart.com

? ?Sell the alpha, not the feature?: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr

? A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

? Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle

? Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

? Atlassian: atlassian.com

?

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

?

Lenny may be an investor in the companies discussed.

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me.

We discuss:

* When to coach and when to just tell people what to do [09:00]

* The GROW technique for helping people figure out a solution for themselves [18:37]

* Techniques for making difficult conversations less difficult [01:20:28]

* Avoiding burnout and designing a more energizing career [41:55]

* Building and sustaining a healthy co-founder relationship [01:06:50]

* Creating a one-page plan that aligns your entire company [01:31:47]

* Practical ways AI is transforming executive coaching and leadership development [01:36:50]

* Why you should ask, ?Would I enthusiastically rehire this person?? to clarify talent decisions [23:55]

Also on Spotify and Apple Podcasts

Brought to you by:

Stripe?Helping companies of all sizes grow revenue

Vanta?Automate compliance. Simplify security.

Persona?A global leader in digital identity verification

Where to find Rachel Lockett:

? LinkedIn: https://www.linkedin.com/in/rhlockett/

? Website: https://www.lockettcoaching.com

Referenced:

? One-page plan template: https://www.lockettcoaching.com/#resources

? Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0

? Renew Your Co-Founder Vows?and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/

? First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0

? Coinbase: https://www.coinbase.com

? Management Time: Who?s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

? Chuck Palahniuk?s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to

? Patrick Collison on X: https://x.com/patrickc

? Stripe: https://stripe.com

? Remind: https://www.remind.com

? Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams

? Brex: https://www.brex.com

? Bridge: https://www.bridge.xyz

? 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

? 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

? The Enneagram Institute: https://www.enneagraminstitute.com

? How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, ?Touchy Feely?): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

? How have I been complicit in creating the conditions I say I don?t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna

? How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

? What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst

? How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver

? Granola: https://www.granola.ai

? KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621

? Loom: https://www.loom.com

? Joseph Campbell?s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front

? Wes Anderson?s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-films

Recommended books:

? Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X

? The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904

? Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321

? Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293

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

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech?s biggest acquisitions, he?s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From ?utility curves? to ?the owner?s delusion? to ?hyper-realistic work-like activities,? his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams.

We discuss:

1. Hyper-realistic work-like activities

2. The owner?s delusion

3. Utility curves

4. ?Don?t make me think?

5. ?We don?t sell saddles here?

6. Tilting your umbrella

7. When to pivot

?

Brought to you by:

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

Metronome?Monetization infrastructure for modern software companies

Lovable?Build apps by simply chatting with AI

?

Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation

?

Where to find Stewart Butterfield:

? X: https://x.com/stewart

? LinkedIn: https://www.linkedin.com/in/butterfield

?

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 Stewart Butterfield

(04:58) Stewart?s current life and reflections

(06:44) Understanding utility curves

(10:13) The concept of divine discontent

(15:11) The importance of taste in product design

(19:03) Tilting your umbrella

(28:32) Balancing friction and comprehension

(45:07) The value of constant dissatisfaction

(47:06) Embracing continuous improvement

(50:03) The complexity of making things work

(54:27) Parkinson?s law and organizational growth

(01:03:17) Hyper-realistic work-like activities

(01:13:23) Advice on when to pivot

(01:18:36) The importance of generosity in leadership

(01:26:34) The owner?s delusion

?

Referenced:

? Slack: https://slack.com

? Flickr: https://www.flickr.com

? Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal

? Blok: https://blok.so

? Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b

? Magic Link: https://en.wikipedia.org/wiki/Magic_Link

? Ticketmaster: https://www.ticketmaster.com

? John Collison on X: https://x.com/collision

? Patrick Collison on X: https://x.com/patrickc

? Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai

? Three Questions with Slack?s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo

? Six Sigma: https://www.6sigma.us

? What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system

? John Collison?s post on X about passion projects: https://x.com/collision/status/1529452415346302976

? Parkinson?s law: https://www.economist.com/news/1955/11/19/parkinsons-law

? We Don?t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d

? Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game)

? IRC: https://en.wikipedia.org/wiki/IRC

? This will make you a better decision-maker | Annie Duke (author of ?Thinking in Bets? and ?Quit,? former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke

? The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva

? Prisoner?s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma

? Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little

? Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg

? Stewart?s post on X referencing ?the owner?s delusion?: https://x.com/stewart/status/1223286626991796224

?

Recommended books:

? Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021

? Why Nothing Works: Who Killed Progress?and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X

? Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586

? Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996

?

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

?

Lenny may be an investor in the companies discussed.

Dr. Fei-Fei Li is known as the ?godmother of AI.? She?s been at the center of AI?s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we?re living right now, served as Google Cloud?s Chief AI Scientist, directed Stanford?s Artificial Intelligence Lab, and co-founded Stanford?s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely told history of how we got here?including the wild fact that just nine years ago, calling yourself an AI company was basically a death sentence.

We discuss:

1. How ImageNet helped spark the AI explosion we?re living through

2. Why world models and spatial intelligence represent the next frontier in AI, beyond large language models

3. Why Fei-Fei believes AI won?t replace humans but will require us to take responsibility for ourselves

4. The surprising applications of Marble, from movie production to psychological research

5. Why robotics faces unique challenges compared with language models and what?s needed to overcome them

6. How to participate in AI regardless of your role

?

Brought to you by:

Figma Make?A prompt-to-code tool for making ideas real

Justworks?The all-in-one HR solution for managing your small business with confidence

Sinch?Build messaging, email, and calling into your product

?

Transcript: https://www.lennysnewsletter.com/p/the-godmother-of-ai

?

My biggest takeaways (for paid newsletter subscribers):

https://www.lennysnewsletter.com/i/178223233/my-biggest-takeaways-from-this-conversation

?

Where to find Dr. Fei-Fei Li

? X: https://x.com/drfeifei

? LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247

? World Labs: https://www.worldlabs.ai

?

Where to find Lenny:

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

? X: https://twitter.com/lennysan

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

?

In this episode, we cover:

(00:00) Introduction to Dr. Fei-Fei Li

(05:31) The evolution of AI

(09:37) The birth of ImageNet

(17:25) The rise of deep learning

(23:53) The future of AI and AGI

(29:51) Introduction to world models

(40:45) The bitter lesson in AI and robotics

(48:02) Introducing Marble, a revolutionary product

(51:00) Applications and use cases of Marble

(01:01:01) The founder?s journey and insights

(01:10:05) Human-centered AI at Stanford

(01:14:24) The role of AI in various professions

(01:18:16) Conclusion and final thoughts

?

References: https://www.lennysnewsletter.com/p/the-godmother-of-ai

?

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

?

Lenny may be an investor in the companies discussed.

Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that?s one of the hottest and most interesting AI startups in the world right now. They?re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive business in a category most investors dismissed. In fact, one investor told Grant his idea was ?the dumbest idea he had ever heard.?

We discuss:

? How Gamma found product-market fit by rethinking their onboarding

? Their process for building a ?word-of-mouth machine?

? How they leveraged more than 1,000 micro-influencers instead of big names

? Why focusing on the ?first 30 seconds? transformed their business

? Their approach to pricing that led to profitability within months

? How Grant thinks about building a durable ?GPT wrapper? business

?

Brought to you by:

Vanta?Automate compliance. Simplify security.

Justworks?The all-in-one HR solution for managing your small business with confidence

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

?

Where to find Grant Lee:

? X: https://x.com/thisisgrantlee

? LinkedIn: https://www.linkedin.com/in/grantslee

?

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 Grant Lee and Gamma

(05:59) The founding story of Gamma

(09:52) Achieving product-market fit

(15:43) Self-awareness as a founder

(17:17) The power of onboarding

(20:41) The original insight that led to Gamma

(22:42) Founder-led marketing and growth tactics

(29:20) Sharing online

(37:40) Getting to $100M ARR

(41:19) Influencer marketing as a growth strategy

(54:08) Virality is not an accident

(58:30) Investing in brand before paid ads

(01:02:04) Tips for getting started with performance marketing

(01:04:49) Prototyping and user feedback

(01:16:12) Adapting and moving quickly

(01:19:21) The concept of GPT wrapper companies

(01:22:16) Deep dive into workflow and model utilization

(01:29:06) Pricing strategies

(01:34:53) Hiring philosophy and practices

(01:43:24) Betting big on high performers

(01:45:03) Final thoughts and lightning round

?

References: https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn

?

Lenny may be an investor in the companies discussed.

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She?s one of the smartest people I?ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR.

We discuss:

1. Why the ?mid-market? doesn?t exist

2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers

3. The dangers of pricing your product at $10K-$20K

4. Why you need to vision-cast instead of problem-solve to win enterprise deals

5. Why services are the fastest way to get your foot in the door with enterprises

6. How to find and work with design partners

7. When to hire your first salesperson and what profile to look for

?

Brought to you by:

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

Lovable?Build apps by simply chatting with AI

Coda?The all-in-one collaborative workspace

?

Where to find Jen Abel:

? X: https://x.com/jjen_abel

? LinkedIn: https://www.linkedin.com/in/earlystagesales

? Website: https://www.jjellyfish.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) Welcome back, Jen!

(04:38) The myth of the mid-market

(08:08) Targeting tier-one logos

(10:50) Vision-casting vs. problem-selling

(15:35) The importance of high ACVs

(20:45) ?Don?t play the small business game with an enterprise company

(25:09) Design partners: the double-edged sword

(28:11) Finding the right company

(36:55) Enterprise sales: the art of the deal

(43:21) The problem with channel partnerships

(44:41) Quick summary

(50:24) Hiring the right enterprise salespeople

(56:49) Structuring sales compensation

(01:01:01) Building relationships in enterprise sales

(01:02:07) The art of cold outreach

(01:07:31) Outbound tooling and AI

(01:14:08) Lightning round and final thoughts

?

Referenced:

? The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

? Mario meme: https://www.linkedin.com/pulse/missing-meme-led-me-woman-johann-van-tonder-im6df

? Kathy Sierra: https://en.wikipedia.org/wiki/Kathy_Sierra

? 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

? Justin Lawson on X: https://x.com/jjustin_lawson

? 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

? 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

? 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

? Linear: https://linear.app

? 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

? Gemini: https://gemini.google.com

? Microsoft Copilot: https://copilot.microsoft.com

? How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi

? McKinsey & Company: https://www.mckinsey.com

? Deloitte: https://www.deloitte.com

? Accenture: https://www.accenture.com

? Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

? Peter Dedene on X: https://x.com/peterdedene

? Hang Huang on X: https://x.com/HH_HangHuang

? Hugo Alves on X: https://x.com/Ugo_alves

? A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

? Clay: https://www.clay.com

? Apollo: https://www.apollo.io

? Jason Lemkin on X: https://x.com/jasonlk

? Gavin Baker on X: https://x.com/GavinSBaker

? Jason Cohen on X: https://x.com/asmartbear

? Baywatch on Prime Video: https://www.primevideo.com/detail/Baywatch/0NU9YS8WWRNQO1NZD5DOQ3I8W6

? Playground: https://www.tryplayground.com

? ClassDojo: https://www.classdojo.com

? Jason Lemkin?s post about Replit: https://x.com/jasonlk/status/1946069562723897802

?

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

?

Lenny may be an investor in the companies discussed.

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls ?column B? thinking: building toward a dream future rather than just using the bricks around you.

We discuss:

1. How ?column B? thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints

2. The power of setting ?crazy big goals?

3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase

4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch

5. Canva?s ?two-step plan?: build one of the world?s most valuable companies, then do the most good possible

6. Melanie?s vision for 2050 and why she believes imagination is the first step toward a better world

?

Brought to you by:

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

Stripe?Helping companies of all sizes grow revenue: https://stripe.com/

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

?

Transcript: ?https://www.lennysnewsletter.com/p/the-making-of-canva??

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation

?

Where to find Melanie Perkins:

? X: https://x.com/melaniecanva

? LinkedIn: https://www.linkedin.com/in/melanieperkins/

?

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 Melanie Perkins and Canva

(04:44) Building a ?column B? company

(06:36) Operationalizing big visions

(13:13) Crazy big goals and celebrations

(22:00) Challenges and setbacks in Canva?s journey

(26:30) Fundraising and investor rejections

(29:36) Leadership and growth lessons

(34:38) Canva?s goal-driven structure

(35:46) Balancing work and personal life

(38:02) Community-driven product development

(40:37) The two-step plan for global impact

(45:04) Canva?s biggest launch yet

(48:10) How Canva approaches product expansion

(52:37) AI integration in Canva

(53:56) AI corner

(55:22) Melanie?s vision for 2050 and beyond

(01:00:07) Lightning round and final thoughts

?

Referenced:

? Canva: https://www.canva.com/

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

? Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa

? UserTesting: https://www.usertesting.com/

? Figma: https://www.figma.com/

? Adobe: https://www.adobe.com/

? Calm: https://www.calm.com/

? Gandhi?s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593

? Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/

?

Recommended books:

? Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/

? The Lean Startup: How Today?s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/

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

? Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855

?

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

Lenny may be an investor in the companies discussed.

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

?

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

?

Where to find Dhanji R. Prasanna:

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

?

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 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

?

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

?

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/

?

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

?

Lenny may be an investor in the companies discussed.

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

?

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

?

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

?

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 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

?

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

?

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

?

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

Lenny may be an investor in the companies discussed.

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

?

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

?

Where to find Nicole Forsgren:

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

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

? Website: https://nicolefv.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 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

?

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/

?

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/

?

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

Lenny may be an investor in the companies discussed.

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

?

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/

?

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 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

?

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/

?

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 [email protected].

?

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.

?

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 

?

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/

?

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 [email protected].

?

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 [email protected].

?

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 [email protected].

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 [email protected].

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 [email protected].

?

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 [email protected].

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 [email protected].

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 [email protected].

?

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 [email protected].

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 [email protected].

?

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: [email protected]

?

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 [email protected].

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 [email protected].

?

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: [email protected]

?

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 [email protected].

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 [email protected].

?

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 [email protected].

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 [email protected].

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 [email protected].

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 [email protected].

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 [email protected].

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: [email protected] ? 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 [email protected].

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 [email protected].

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 [email protected].

Lenny may be an investor in the companies discussed.

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can?t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days.

What you?ll learn:

1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days?including templates you can use immediately

2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team)

3. The three fundamental questions every founder should answer before writing a line of code

4. The ?note and vote? technique that eliminates groupthink and gets honest answers from your colleagues

5. The seven ?magic lenses? for choosing between multiple product ideas

6. The biggest mistake engineers make when building with AI tools

7. The paradox of speed: why ?building nothing first? can get you to product-market fit faster

?

Brought to you by:

Brex?The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs

Paragon?Ship every SaaS integration your customers want: https://www.useparagon.com/lenny

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

?

Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky

?

My biggest takeaways (for paid newsletter subscribers):

https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation

?

Where to find Jake Knapp:

? X: https://twitter.com/jakek

? LinkedIn: https://www.linkedin.com/in/jake-knapp/

? Website: https://jakeknapp.com/

?

Where to find John Zeratsky:

? X: https://twitter.com/jazer

? LinkedIn: https://www.linkedin.com/in/johnzeratsky/

? Website: https://johnzeratsky.com/

?

In this episode, we cover:

(00:00) Introduction to Jake Knapp and John Zeratsky

(04:41) Origins of the Design Sprint

(11:06) The Foundation Sprint process

(14:40) Phase one: The basics

(16:57) Case study: Latchet

(28:50) Phase two: Differentiation

(36:24) The importance of differentiation

(40:15) Thoughts on price differentiation

(43:37) Case study: Mellow

(46:04) Custom differentiators

(49:30) The mini manifesto

(52:02) Phase three: Approach to the project

(54:50) Magic lenses activity

(01:02:39) Prototyping and testing

(01:10:00) Real-world examples and success stories

(01:15:15) Motivation behind The Foundation Sprint

(01:17:15) The outcome of the sprint: The founding hypothesis

(01:19:28) The Design Sprint

(01:28:19) The role of AI in prototyping

(01:36:50) Final thoughts and resources

?

Referenced:

? Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint

? Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake

? Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/

? Character Capital: https://www.character.vc/

? Character Labs: https://www.character.vc/labs

? Etsy: https://www.etsy.com/

? Shopify: https://www.shopify.com/

? Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek

? Sonos: https://www.sonos.com/

? Vercel: https://vercel.com/

? Windsurf: https://windsurf.com/

? April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning

? Positioning: https://www.lennysnewsletter.com/p/positioning

? 10 things we know to be true: https://about.google/company-info/philosophy/

? Gandalf: https://en.wikipedia.org/wiki/Gandalf

? Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins

? Mordor: https://en.wikipedia.org/wiki/Mordor

? 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley

? The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas

? 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

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

? Blue Bottle Coffee: https://bluebottlecoffee.com

? Reclaim: https://reclaim.ai/

? The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template

? Rippling: https://www.rippling.com/

? Latchet: https://latchet.com/

? Mellow: http://getmellow.com/

? AxionOrbital: https://axionorbital.space/

?

Recommended books:

? Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY

? Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

? Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114

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

?

Lenny may be an investor in the companies discussed.

Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding.

What you?ll learn:

1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing

2. How he hasn?t written a single line of front-end code in three months?and how to structure your code repository to make it easier for AI to write your code

3. His AI productivity stack that allowed him to compete against heavily funded competitors

4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business)

5. The story of signing the $80M acquisition deal while war broke out with Iran

6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable)

7. The counterintuitive product decision that tripled activation by removing a ?helpful? feature

8. How building in public on LinkedIn drove more growth than any paid channel

?

Brought to you by:

Sauce?Turn customer pain into product revenue: https://sauce.app/lenny

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

Contentsquare?Create better digital experiences: https://contentsquare.com/lenny/

?

Transcript: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo

?

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation

?

Where to find Maor Shlomo:

? X: https://x.com/ms_base44

? LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/

?

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 Maor and Base44

(08:16) The origin story: how Base44 came to be

(14:55) Bootstrapping and solo founding: challenges and insights

(22:52) Productivity hacks and tech stack for solo founders

(27:23) How to get started using Base44

(28:47) Thoughts on raising money

(34:05) Distribution in the age of AI

(36:09) Ambition and goals

(40:05) Growth strategies: from first users to thousands

(51:32) Building in public

(57:42) The solo founder journey

(01:00:23) Community support

(01:03:23) Hackathons and partnerships

(01:06:42) The importance of velocity in product development

(01:08:20) Technical stack and infrastructure insights

(01:15:24) Activation lessons

(01:18:19) The acquisition journey with Wix

(01:25:14) Final thoughts and advice for founders

?

Referenced:

? Base44: https://base44.com/

? Retool: https://retool.com/

? Tzofim: https://www.israelscouts.org/

? Y Combinator: https://www.ycombinator.com/

? RescueTime: https://www.rescuetime.com/

? Cursor: https://www.cursor.com/

? Wix: https://www.wix.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

? 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

? 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

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

? 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

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

? Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72

? WhatsApp: https://www.whatsapp.com/

? Amazon: https://www.amazon.com/

? Google: https://about.google/

? MongoDB: https://www.mongodb.com/

? Deloitte: https://www.deloitte.com/

? Render: Render.com

? Claude 4: https://www.anthropic.com/news/claude-4

? Gemini: https://gemini.google.com/app

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

?

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

Lenny may be an investor in the companies discussed.

Andrew Wilkinson is the co?founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he?s created a portfolio approaching $300?million in yearly sales (and he was personally worth over $1 billion at one point)?all without ever raising venture capital.

In this conversation, you?ll learn:

1. The ?fish where the fish are? framework for spotting high?margin niches no one else notices

2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew?s day-to-day productivity (and has replaced his assistant)

3. How Andrew evaluates companies in less than 15?minutes using Buffett?style moats and ?lazy leadership?

4. Telltale signs you should shut down (or never start) that startup idea

5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication

6. His prediction that most knowledge work will be automated?and the skills to teach your kids now

?

Brought to you by:

Sauce?Turn customer pain into product revenue

Enterpret?Transform customer feedback into product growth

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

?

Where to find Andrew Wilkinson:

? X: https://x.com/awilkinson

? LinkedIn: https://www.linkedin.com/in/awilkinson/

?

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 Andrew Wilkinson

(04:07) Finding the right business idea

(07:18) Avoiding common business pitfalls

(11:58) Finding your unfair advantage

(17:08) Fish where the fish are

(20:08) Why boring is good

(25:30) Bootstrapping vs. venture capital

(31:20) Lessons from acquiring and managing businesses

(36:47) Avoiding people problems

(42:39) Leveraging AI in business and life

(49:30) The Limitless device

(53:13) Job displacement and AI?s future impact

(58:20) Advice for new grads

(01:02:50) Parenting in the age of AI

(01:05:26) The pursuit of happiness beyond wealth

(01:10:10) Mental health and medication

(01:16:45) Lightning round and final thoughts

?

Referenced:

? Andrew?s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182

? Metalab: https://www.metalab.com/

? Letterboxd: https://letterboxd.com/

? AeroPress: https://aeropress.com/

? Brian Armstrong on X: https://x.com/brian_armstrong

? Warren Buffett?s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman

? Flow: https://www.getflow.com/

? Instacart: https://www.instacart.com/

? Things: https://culturedcode.com/things/

? Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/

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

? Serato: https://serato.com/

? Chris Sparling on X: https://x.com/_sparling_

? Lindy: https://www.lindy.ai/

? 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

? David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman)

? Malcolm Gladwell?s website: https://www.gladwellbooks.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

? 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

? Limitless: https://www.limitless.ai/

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

? Claude: https://claude.ai/

? ChatGPT: https://chatgpt.com/

? Gemini: https://gemini.google.com/app

? William Gibson?s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly

? Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo

? Sam Altman on X: https://x.com/sama

? Dario Amodei on X: https://x.com/darioamodei

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

? Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc

? Matic vacuum: https://maticrobots.com/

? Jerzy Gregorek?s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life

? Tiny: https://www.tiny.com/

? Dribbble: https://dribbble.com/

?

Recommended books:

? The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143

? How to Get Rich: One of the World?s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719

?

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

?

Lenny may be an investor in the companies discussed.

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft?s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel?s Pentium, Apple?s PowerBook, and Swiffer. Over 40 years, David?s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation.

What you?ll learn:

1. The three-step process that generated names like Windsurf and Vercel

2. How a name can give you the edge that no marketing budget can buy

3. Why you won?t ?know it when you see it?

4. Why Microsoft called Azure ?a dumb name? before it became their billion-dollar cloud platform

5. Why polarizing opinions are the strongest signal that you?ve found the right name

6. How every letter of the alphabet creates a specific psychological vibration

7. The diamond framework: a 4-step process any founder can use to find their perfect name

8. Why domain names don?t matter anymore in the age of AI

?

Brought to you by:

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

Stripe?Helping companies of all sizes grow revenue

OneSchema?Import CSV data 10x faster

?

Where to find David Placek:

? LinkedIn: https://www.linkedin.com/in/david-placek-05a82/

? Website: https://www.lexiconbranding.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 David and Lexicon Branding

(04:44) The story of Sonos

(09:27) The psychology of naming

(11:33) The initial resistance to Microsoft's Azure

(14:35) The importance of a great brand name

(18:11) The three steps of naming: create, invent, implement

(28:23) Qualities of great brand name creators

(31:24) How long the naming process takes

(32:12) The Windsurf case study

(36:10) Naming in the AI era

(39:37) When to change your name

(43:10) The role of linguists

(45:54) The power of letters in branding

(48:15) The Vercel case study

(50:12) The implementation phase

(52:52) Client management and market success

(55:16) The diamond exercise

(01:04:23) Suspending judgment

(01:07:31) Polarization and boldness

(01:11:01) Domain names

(01:12:48) Final thoughts and lightning round

?

Referenced:

? PowerBook: https://en.wikipedia.org/wiki/PowerBook

? Pentium: https://en.wikipedia.org/wiki/Pentium

? BlackBerry: https://en.wikipedia.org/wiki/BlackBerry

? Swiffer: https://www.swiffer.com/

? Impossible Burger: https://impossiblefoods.com/

? Vercel: https://vercel.com/

? Windsurf: https://windsurf.com/

? CapCut: https://www.capcut.com/

? Azure: https://azure.microsoft.com/

? Sonos: https://www.sonos.com/

? John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/

? Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series)

? The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild

? 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

? Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism

? Anduril: https://www.anduril.com/

? Anthropic: https://www.anthropic.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

? 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 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

? Y Combinator: https://www.ycombinator.com/

? Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette

? Viagra: https://www.viagra.com/

? In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas

? Infoseek: https://en.wikipedia.org/wiki/Infoseek

? Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove

? Churchill at War on Netflix: https://www.netflix.com/title/81609374

? Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z

? 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW

? 1923 on Paramount+: https://www.paramountplus.com/shows/1923/

? Taylor Sheridan on X: https://x.com/taylorSheridan

? Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods

? T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by

? Lawrence of Arabia: https://www.imdb.com/title/tt0056172/

? DreamWorks: https://www.dreamworks.com/

?

Recommended books:

? Thucydides? Melian Dialogue: Commentary, Text, and Vocabulary: https://www.amazon.com/Thucydides-Melian-Dialogue-Commentary-Vocabulary/dp/0692772367

? Resilience: Hard-Won Wisdom for Living a Better Life: https://www.amazon.com/Resilience-Hard-Won-Wisdom-Living-Better/dp/054432398X/

? Churchill: Walking with Destiny: https://www.amazon.com/Churchill-Walking-Destiny-Andrew-Roberts/dp/1101980990

?

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

?

Lenny may be an investor in the companies discussed.

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions?including Facebook?s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he?s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech?s most iconic products and companies.

What you?ll learn:

1. Peter?s one?sentence test for hiring superstars

2. Why your product (probably) doesn?t matter

3. Why you don?t need a tech breakthrough to build a huge business

4. The five PM archetypes, and how to build a team of Avengers

5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 100

6. The importance of data flywheels and workflows

?

Brought to you by:

Paragon?Ship every SaaS integration your customers want

Pragmatic Institute?Industry?recognized product, marketing, and AI training and certifications

Contentsquare?Create better digital experiences

?

Where to find Peter Deng:

? X: https://x.com/pxd

? LinkedIn: https://www.linkedin.com/in/peterxdeng/

?

In this episode, we cover:

(00:00) Introduction to Peter Deng

(05:41) AI and AGI insights

(11:35) The future of education with AI

(16:53) The power of language in leadership

(21:01) Building iconic products

(36:44) Scaling from zero to 100

(41:56) Balancing short- and long-term goals

(47:12) Creating a healthy tension in teams

(50:02) The five archetypes of product managers

(55:39) Primary and secondary archetypes

(58:47) Hiring for growth mindset and autonomy

(01:15:52) Effective management and communication strategies

(01:19:23) Presentation advice and self-advocacy

(01:25:50) Balancing craft and practicality in product management

(01:30:40) The importance of empathy in design thinking

(01:35:45) Career decisions and learning opportunities

(01:42:05) Lessons from product failures

(01:45:42) Lightning round and final thoughts

?

Referenced:

? OpenAI: https://openai.com/

? Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence

? Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire?s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw

? Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What

? Herbert H. Clark: https://web.stanford.edu/~clark/

? Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/

? Ilya Sutskever (OpenAI Chief Scientist)?Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever

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

? Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/

? 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

? Microsoft CPO: If you aren?t prototyping with AI, you?re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai

? 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

? Granola: https://www.granola.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

? 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

? Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/

? Airtable: https://www.airtable.com/

? George Lee on LinkedIn: https://www.linkedin.com/in/geolee/

? Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/

? Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/

? Twilio: https://www.twilio.com/

? Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/

? Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/

? Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/

? Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/

? Ryan O?Rourke?s website: https://www.rourkery.com/

? Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/

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

? Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/

? Guy Kawasaki?s website: https://guykawasaki.com/

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

? Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/

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

? The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process

? 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

? Jeff Bezos?s quote: https://news.ycombinator.com/item?id=27778175

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

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

? How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen

? ?Smile? by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1

? The Wire on HBO: https://www.hbo.com/the-wire

? Felicis: https://www.felicis.com/

?

Recommended books:

? Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095

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

? The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375

?

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

?

Lenny may be an investor in the companies discussed.

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT?s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn?t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques.

In this episode, you?ll learn:

1. The 5 most effective prompt engineering techniques

2. Why ?role prompting? and threatening the AI no longer works?and what to do instead

3. The two types of prompt engineering: conversational and product/system prompts

4. A primer on prompt injection and AI red teaming?including real jailbreak tactics that are still fooling top models

5. Why AI agents and robots will be the next major security threat

6. How to get started in AI red teaming and prompt engineering

7. Practical defense to put in place for your AI products

?

Brought to you by:

Eppo?Run reliable, impactful experiments

Stripe?Helping companies of all sizes grow revenue

Vanta?Automate compliance. Simplify security

?

Where to find Sander Schulhoff:

? X: https://x.com/sanderschulhoff

? LinkedIn: https://www.linkedin.com/in/sander-schulhoff/

? Website: https://sanderschulhoff.com/

? AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC

? Free Lightning Lesson ?How to Secure Your AI System? on 6/24: https://bit.ly/4ld9vZL

?

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 Sander Schulhoff

(04:29) The importance of prompt engineering

(06:30) Real-world applications and examples

(10:54) Basic prompt engineering techniques

(23:46) Advanced prompt engineering techniques

(29:00) The role of context and additional information

(39:24) Ensembling techniques and thought generation

(49:48) Conversational techniques for better results

(50:46) Introduction to prompt injection

(52:27) AI red teaming and competitions

(54:23) The growing importance of AI security

(01:02:45) Techniques to bypass AI safeguards

(01:05:21) Challenges in AI security and future outlook

(01:18:33) Misalignment and AI's potential risks

(01:25:03) Final thoughts and lightning round

?

Referenced:

? Reid Hoffman?s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822

? AI Engineer World?s Fair: https://www.ai.engineer/

? What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi

? Devin: https://devin.ai/

? Cursor: https://www.cursor.com/

? Inside Devin: The world?s first autonomous AI engineer that?s set to write 50% of its company?s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu

? 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

? Granola: https://www.granola.ai/

? 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

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

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

? 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

? Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv

? The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0

? State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo

? Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags

? Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7

? Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn

? Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI

? LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval

? Philip Resnik on X: https://x.com/psresnik

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

? Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh

? Random forest: https://en.wikipedia.org/wiki/Random_forest

? Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx

? Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn

? Announcing HackAPrompt 2.0: The World?s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp

? Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment

? 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

? Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX

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

? Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction

? Sam Altman on X: https://x.com/sama

? Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics

? Anthropic?s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/

? Palisade Research: https://palisaderesearch.org/

? When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/

? A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html

? 1883 on Paramount+: https://www.paramountplus.com/shows/1883/

? Black Mirror on Netflix: https://www.netflix.com/title/70264888

? Daylight Computer: https://daylightcomputer.com/

? Theodore Roosevelt?s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease

? HackAPrompt 2.0: https://www.hackaprompt.com/

?

Recommended books:

? Ender?s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706

? The River of Doubt: Theodore Roosevelt?s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736

?

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

?

Lenny may be an investor in the companies discussed.