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/

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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

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

Lenny may be an investor in the companies discussed.