AI Powered Insights from Lenny's Podcast

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: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/172703231/my-biggest-takeaways-from-this-conversation *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 *Referenced:* • AEO Tools: https://bit.ly/graphite-aeo-tool • The ultimate guide to SEO | Ethan Smith (Graphite): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-seo-ethan-smith • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Webflow: https://webflow.com/ • YouTube: https://youtube.com/ • Reddit: https://www.reddit.com/ • Quora: https://www.quora.com/ • An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth): https://www.lennysnewsletter.com/p/an-inside-look-at-deels-unprecedented • Dotdash Meredith: https://www.people.inc/ • Forbes: https://www.forbes.com/ • Vimeo: https://vimeo.com/ • Perplexity: https://www.perplexity.ai/ • Gemini: https://gemini.google.com/ • ChatGPT: https://chatgpt.com/ • Claude: https://claude.ai/ • TechRadar: https://www.techradar.com/ • Yelp: https://www.yelp.com • Tripadvisor: https://www.tripadvisor.com/ • TikTok: https://www.tiktok.com/ • 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 • AI SEO: Latest Market Intelligence & Landscape Analysis—Summer Sessions: https://www.youtube.com/watch?v=cm589PmhIOY • AI Content Study: https://bit.ly/ai-content-white-paper • Free AI detector: https://surferseo.com/ai-content-detector/ • Common Crawl: https://commoncrawl.org/ • AI models collapse when trained on recursively generated data: https://www.nature.com/articles/s41586-024-07566-y • Looker: https://cloud.google.com/looker/ ...References continued at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom. *In our conversation, Ben shares:* 1. Why “founder mode” is half right and half dangerously wrong 2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger 3. Where the biggest AI startup opportunities remain 4. Why you need to run toward fear, never away 5. The one trait that predicts that a founder will fail as CEO 6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists *Brought to you by:* DX—The developer intelligence platform designed by leading researchers: https://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 *Referenced:* • Shaka Senghor on The Joe Rogan Experience: https://open.spotify.com/episode/79neOSawKbrxY6Tl2wV1Kx • 1999 Martha’s Vineyard plane crash: https://en.wikipedia.org/wiki/1999_Martha%27s_Vineyard_plane_crash • John Reed: https://en.wikipedia.org/wiki/John_S._Reed# • LoudCrowd: https://loudcrowd.com/ • Marc Andreessen on X: https://x.com/pmarca • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/ • Databricks: https://www.databricks.com/ • Ion Stoica on LinkedIn: https://www.linkedin.com/in/ionstoica/ • Hadoop: https://hadoop.apache.org/ • The Sad Truth About Developing Executives: https://a16z.com/the-sad-truth-about-developing-executives/ • Mark Zuckerberg on Facebook: https://www.facebook.com/zuck/ • Sam Altman on X: https://x.com/sama • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Brian Chesky—Founder Mode & The Art of Hiring: https://www.youtube.com/watch?v=aFOGlNL39xs • Bob Iger: https://en.wikipedia.org/wiki/Bob_Iger • Larry Page: https://en.wikipedia.org/wiki/Larry_Page • Kanye West: https://en.wikipedia.org/wiki/Kanye_West • Diddy: https://en.wikipedia.org/wiki/Sean_Combs • Arsalan Tavakoli on LinkedIn: https://www.linkedin.com/in/arsalantavakoli/ • Good Product Manager/Bad Product Manager: https://a16z.com/good-product-manager-bad-product-manager/ • Netscape: https://en.wikipedia.org/wiki/Netscape • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/ • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden/ • Raghu Raghuram on LinkedIn: https://www.linkedin.com/in/raghuraghuram/ • Adam Neumann on X: https://en.wikipedia.org/wiki/Adam_Neumann • WeWork: https://www.wework.com/ • Cluely: https://cluely.com/ ...References continued at: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

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: https://www.lucidlink.com/lenny DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ *Transcript:* ⁠⁠⁠https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai *My biggest takeaways (for paid newsletter subscribers):* ⁠https://www.lennysnewsletter.com/i/171904193/my-biggest-takeaways-from-this-conversation *Where to find Howie Liu* • X: https://x.com/howietl • LinkedIn: https://www.linkedin.com/in/howieliu/ • Email: howie@airtable.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Howie Liu and Airtable (04:05) The “Airtable is dead” viral tweet controversy (08:07) The rise of IC CEOs (10:57) AI’s paradigm shift in product development (16:27) Specific changes Airtable has made (21:38) Fast- and slow-thinking teams (32:57) The emergence of new form factors in AI models (34:48) Airtable’s vision and philosophy (40:20) Empowering teams with AI tools (46:50) Encouraging experimentation and play (50:55) Cross-functional skills in product teams (01:03:35) The importance of evals and open-ended testing (01:08:06) Key strategies for AI-driven success (01:12:43) Counterintuitive startup wisdom (01:22:21) Don't step away from the details that you love (01:25:50) Advice for aspiring engineers and designers (01:30:00) Lightning round and final thoughts *Referenced:* • Airtable: https://www.airtable.com/ • All In podcast: https://allin.com/ • Nikita Bier on X: https://x.com/nikitabier • Figma: https://www.figma.com/ • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Every: https://every.to/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Rippling: https://www.rippling.com/ • Omni: https://www.airtable.com/lp/ai-psu-plp • How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Palantir: https://www.palantir.com/ • Harvey: https://www.harvey.ai/ • v0: https://v0.dev/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Replit: https://replit.com/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika ...References continued at: https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger. *What you’ll learn:* 1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders 2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era 3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle 4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning 5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company 6. The three-phase pattern every successful AI company follows (and why most fail at phase one) 7. The rise of code-native interfaces and why GUIs might be going the way of the desktop 8. What Asha learned from Satya Nadella about optimism *Brought to you by:* Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—The developer intelligence platform designed by leading researchers: https://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 ...References continued at: https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma _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.

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: https://www.claude.ai/lenny *Transcript:* https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation *Where to find Garrett Lord:* • X: https://x.com/garrettlord • LinkedIn: https://www.linkedin.com/in/garrettlord/ • Email: Garrett@joinhandshake.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Garrett Lord (05:00) Understanding data labeling and its importance (13:08) The role of experts in AI model training (15:35) The future of AI and human collaboration (24:17) Why AI won’t eliminate entry-level jobs (27:58) The continuous improvement of AI models (33:05) The emergence of Handshake’s new business model (37:07) Incubating new ideas in established companies (40:42) Handshake's competitive advantage (45:43) Scaling up and meeting market demand (48:38) Overcoming challenges and adapting (53:08) The importance of separate teams and ownership (57:26) The future of job matching with AI (01:00:30) The biggest bottlenecks to advancing models further (01:02:37) Lightning round and final thoughts *Referenced:* • GPQA: https://github.com/idavidrein/gpqa • Handshake: https://joinhandshake.com/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Goldman Sachs: https://www.goldmansachs.com/ • General Motors: https://www.gm.com/ • Google: https://about.google/ • Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/ • Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/ • Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/ • Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac • SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet • Careers at Handshake: https://joinhandshake.com/careers/ *Recommended books:* • Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296 • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies. *We discuss:* 1. Why Eoghan believes most late-stage companies won’t survive the AI transition 2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction 3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail) 4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+ 5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket 6. The cultural transformation required to compete with AI-native startups 7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach *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 *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: https://getdx.com/lenny *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 ...References continued at: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe⁠ _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.