Lenny's Podcast: Product | Career | Growth

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year. In our in-depth discussion, Amol shares: 1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger 2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”) 3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive 4. Why activation is the single highest-leverage growth problem in AI 5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams) 6. How he uses Cowork to detect team misalignment in Slack 7. How the company’s focus on AI coding created a research flywheel that accelerated their models — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Amol Avasare: • X: https://x.com/TheAmolAvasare • LinkedIn: https://www.linkedin.com/in/amolavasare — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Amol and Anthropic’s growth (03:15) The story of cold emailing Mike Krieger to get the job (08:28) What it’s like leading growth at the fastest-growing company ever (10:46) What the growth team actually does at Anthropic (12:16) The concept of “success disasters” (13:55) Why activation is the biggest challenge in AI products (18:05) Improving Mercury’s onboarding experience (20:57) The importance of adding the right kind of friction (25:10) Anthropic’s org structure (27:06) Why Anthropic focuses on big bets over micro-optimizations (33:34) Automating growth experiments with Claude (CASH) (38:20) How AI is starting to identify what experiments to run (41:07) The future of PM, engineering, and design roles (47:19) Why you might need more PMs as engineers get more productive (51:13) How Amol uses AI to prototype ideas and skip PRDs (58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically (1:03:31) Getting coaching from an AI version of your manager (1:06:27) How Anthropic’s focus on coding and B2B drove their success (1:12:10) Balancing growth with AI safety as a core mission (1:18:09) Advice for thriving in an AI-first future (1:22:53) Anthropic’s culture and the “notebook channels” on Slack (1:35:12) Failure corner: Shutting down his startup after raising money (1:38:25) The traumatic brain injury that changed everything (1:46:49) Lightning round — References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net. In our in-depth conversation, Simon shares: 1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works” 2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m. 3. Why mid-career engineers (not juniors) are most at risk right now 4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding) 5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA 6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster 7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Simon Willison: • X: https://x.com/simonw • LinkedIn: https://www.linkedin.com/in/simonwillison • Website: https://simonwillison.net • Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Simon Willison (02:40) The November 2025 inflection point (08:01) What’s possible now with AI coding (10:42) Vibe coding vs. agentic engineering (13:57) The dark-factory pattern (20:41) Where bottlenecks have shifted (23:36) Where human brains will continue to be valuable (25:32) Defending of software engineers (29:12) Why experienced engineers get better results (30:48) Advice for avoiding the permanent underclass (33:52) Leaning into AI to amplify your skills (35:12) Why Simon says he’s working harder than ever (37:23) The market for pre-2022 human-written code (40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026 (44:34) The impact of cheap code (48:27) Simon’s AI stack (54:08) Using AI for research (55:12) The pelican-riding-a-bicycle benchmark (59:01) The inherent ridiculousness of AI (1:00:52) Hoarding things you know how to do (1:08:21) Red/green TDD pattern for better AI code (1:14:43) Starting projects with good templates (1:16:31) The lethal trifecta and prompt injection (1:21:53) Why 97% effectiveness is a failing grade (1:25:19) The normalization of deviance (1:28:32) OpenClaw: the security nightmare everyone is looking past (1:34:22) What’s next for Simon (1:36:47) Zero-deliverable consulting (1:38:05) Good news about Kakapo parrots — References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process. We discuss: 1. Why great ideas often don’t get buy-in 2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much 3. Why executives are usually optimizing for a global maximum while you are often optimizing locally 4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?” 5. Why you should go in to learn, not to convince 6. Why showing only one option is a mistake 7. Why AI will make influence more important, not less — Brought to you by: Omni—AI analytics your customers can trust Lovable—Build apps by simply chatting with AI Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jessica Fain: • LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jessica Fain (03:53) Why influence is the highest-leverage skill in product (04:47) Why great ideas fail without executive buy-in (06:00) How executives actually think (09:05) The fundamentals: context-setting, communication, and empathy (10:22) Stop pitching for approval—start co-creating with execs (12:59) Influence vs. politics (and why people get it wrong) (15:44) How to disagree with execs without losing trust (17:20) Going in to learn, not to convince (19:08) How to present ideas (26:05) The Minto-style approach and tailoring your communication to each exec (28:22) Why Jessica doesn’t like the question “What’s top of mind for you?” (30:24) Understanding incentives to unlock buy-in (32:10) Aligning product work with company strategy (35:10) Quick summary (37:31) Disarming the executive (40:49) Speed matters: why fast follow-up builds momentum (43:32) How to run high-impact meetings (the 60-second rule) (47:00) Why influencing execs is part of your job (49:15) Asking for more resources and thinking in 10x bets (52:23) What to do when your idea gets rejected (54:18) Clarifying information (56:50) How to build trust and make ideas stick (58:30) Shrinking big ideas into experiments (01:02:27) Common mistakes people make when influencing leaders (01:06:00) How to grow into your next role (01:09:32) How AI is changing influence and product work (01:17:55) Using AI to simulate exec feedback and improve pitches (01:21:15) Protecting our brains from overwhelm (01:22:44) Lightning round and final thoughts — Referenced: • Box: https://www.box.com • Slack: https://slack.com • Brightwheel: https://mybrightwheel.com • Webflow: https://webflow.com • April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood • Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua • Atlassian: https://www.atlassian.com • Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid • Calendly: https://calendly.com • Glassdoor: https://www.glassdoor.co.in/index.htm • The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai • Ethan Eismann on X: https://x.com/eeismann • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield • Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank • Checkr: https://checkr.com • Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl • Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan • How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief • Barbara Minto’s website: https://www.barbaraminto.com • How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2 • Casa: https://getcasa.com • Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix • Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles) — Recommended books: • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061 • A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243 • The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes. We discuss: 1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump 2. Why Jacob sees 40% average movement when negotiations are run well 3. When negotiation actually starts (hint: it’s much earlier than you think) 4. Why information + timing create power 5. The biggest mistakes people make when negotiating 6. How to navigate the important “What’s your comp expectation?” question without anchoring too low 7. Why the best interviews feel more like discovery calls than interrogations — Brought to you by: Orkes—The enterprise platform for reliable applications and agentic workflows Mercury—Radically different banking Omni—AI analytics your customers can trust — Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jacob Warwick: • Substack: https://www.execsandthecity.com • YouTube: https://www.youtube.com/@ExecsandtheCity • Website: https://www.thinkwarwick.com • Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jacob Warwick (04:12) How much comp people leave on the table (07:52) Why you shouldn’t feel greedy asking for more (09:45) What founders should know about negotiation (13:03) How Jacob works behind the scenes (15:35) The biggest mistakes people make when negotiating (19:30) Home-field advantage and controlling the conversation (23:02) The step-by-step approach to negotiating an offer (30:17) Jacob’s passion and why these tips don’t work on kids (32:04) Who should speak first about compensation (35:36) Understanding power (39:52) Breaking out of salary bands by focusing on pain points (45:45) Brief summary (47:20) Selling the vacation: How to visualize success (50:07) Controlling the narrative and planting seeds (59:01) Jacob’s role as hype man (01:01:05) Positioning yourself like a product (01:02:49) Making the process frictionless for hiring managers (01:06:20) Flipping the interview to extract information (01:12:17) Five tactical tips for negotiating comp (01:21:45) What to do when negotiations fall apart (01:25:05) Why negotiation is different for every individual (01:28:55) Why outcomes aren’t predetermined (01:32:52) Wild Hollywood negotiation stories (01:37:35) The first step you should take after getting an offer (01:40:30) Jacob’s personal mission (01:44:42) Lightning round and final thoughts — Referenced: • The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating • Sam Altman on X: https://x.com/sama • Tom Brady on X: https://x.com/TomBrady • Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8 • Salesforce: https://www.salesforce.com • Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts • Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon • Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that • Chris Voss on X: https://x.com/fbinegotiator • Werewolf: https://playwerewolf.co • Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion • How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy • ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation • Marvel: https://www.marvel.com • Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030 • Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0 • Minuscule: https://www.youtube.com/user/Minuscule • Claude Cowork: https://claude.com/product/cowork • Macrofactor: https://macrofactor.com • Whoop: https://www.whoop.com • Gemini: https://gemini.google.com/app • The Cody Dieruf Foundation: https://breathinisbelievin.org • Cystic Fibrosis Foundation: https://www.cff.org — Recommended books: • Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941 • Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X • You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229 • Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com