Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.

We discuss:

1. How AI is fundamentally changing the sales function

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

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

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

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

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

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

—

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

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

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

—

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

—

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

—

Where to find Jason Lemkin:

• X: https://x.com/jasonlk

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

• Website: https://www.saastr.com

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Jason Lemkin

(04:36) What SaaStr does

(07:13) AI’s impact on sales teams

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

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

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

(22:03) Why leadership roles are safe

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

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

(30:10) Specific AI agents and their applications

(36:40) Challenges and learnings in AI deployment

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

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

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

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

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

(01:05:40) Forward-deployed engineers

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

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

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

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

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

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

—

Referenced:

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

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

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

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

• Vercel: https://vercel.com

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

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

• Replit: https://replit.com

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

• ElevenLabs: https://elevenlabs.io

• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack

• Bolt: https://bolt.new

• Lovable: https://lovable.dev

• Harvey: https://www.harvey.ai

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

• UiPath: https://www.uipath.com

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

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

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

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

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

• Sierra: https://sierra.ai

• Fin: https://fin.ai

• Deccan: https://www.deccan.ai

• Artisan: https://www.artisan.co

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

• Claude: https://claude.ai

• HubSpot: https://www.hubspot.com

• Gamma: https://gamma.app

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

• Brex: https://www.brex.com

• Outreach: https://www.outreach.io

• Gong: https://www.gong.io

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

• Mixmax: https://www.mixmax.com

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

• Clay: https://www.clay.com

• Owner: https://www.owner.com

• Momentum: https://www.momentum.io

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

• Granola: https://www.granola.ai

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

• Palantir: https://www.palantir.com

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

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

• Rippling: https://www.rippling.com

• Cursor: https://cursor.com

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

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

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

• Sora: https://openai.com/sora

• Reve: https://app.reve.com

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

1. Why “extraordinary results demand extraordinary efforts”

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

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

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Matt MacInnis:

• X: https://x.com/stanine

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

• Email: [email protected]

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Matt MacInnis and Rippling

(04:38) The importance of extraordinary efforts

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

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

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

(16:34) Transitioning to chief product officer

(19:54) Fixing product management at Rippling

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

(28:55) The PQL framework

(35:16) Hiring frameworks and team dynamics

(36:52) A helpful interview tactic

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

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

(46:38) The problem with venture capital

(49:29) When founders should quit their startups

(41:48) The immutable market

(54:13) Lessons from Notion’s success

(57:43) Investment strategies and narrative violations

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

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

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

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

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

(01:23:42) AI corner

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

—

Referenced:

• Rippling: https://www.rippling.com

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

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

• Carvana: https://www.carvana.com

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

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

• Inkling: https://www.inkling.com

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

• Notion: https://www.notion.com

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

• Seeking Alpha: https://seekingalpha.com

• Dennis Rodman’s website: https://dennisrodman.com

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

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

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

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

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

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

• Workday: https://www.workday.com

• Matic robots: https://maticrobots.com

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

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

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

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

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

• Gemini: https://gemini.google.com

• ChatGPT: https://chatgpt.com

• Claude: https://claude.ai

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

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

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.

We discuss:

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

2. Why AI guardrails don’t work

3. Why we haven’t seen major AI security incidents yet (but soon will)

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Sander Schulhoff:

• X: https://x.com/sanderschulhoff

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

• Website: https://sanderschulhoff.com

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Sander Schulhoff and AI security

(05:14) Understanding AI vulnerabilities

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

(17:55) The impact of intelligent agents

(19:44) The rise of AI security solutions

(21:09) Red teaming and guardrails

(23:44) Adversarial robustness

(27:52) Why guardrails fail

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

(44:44) Practical advice for addressing AI security

(55:49) Why you shouldn’t spend your time on guardrails

(59:06) Prompt injection and agentic systems

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

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

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

(01:21:57) Final thoughts and recommendations

—

Referenced:

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

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

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

• OpenAI: https://openai.com

• Scale: https://scale.com

• Hugging Face: https://huggingface.co

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

• Simon Willison’s Weblog: https://simonwillison.net

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

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

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

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

• MathGPT: https://math-gpt.org

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

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

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

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

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

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

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

• Trustible: https://trustible.ai

• Repello: https://repello.ai

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

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

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

—

Brought to you by:

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

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

Persona—A global leader in digital identity verification

—

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

—

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

—

Where to find Elena Verna:

• X: https://x.com/elenaverna

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Elena Verna

(05:19) The scale and growth of Lovable

(08:55) Confidence in Lovable as a business

(12:17) Retention at Lovable

(15:02) Lovable’s unique growth levers

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

(38:09) Launching new features

(40:59) Hiring and team dynamics

(43:17) The value of vibe coding

(49:46) The importance of community

(51:47) Giving away your product for free

(56:26) Tripling their company size

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

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

(01:12:00) Work-life balance

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

(01:19:45) Women in tech

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

—

Referenced:

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

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

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

• Lovable: https://lovable.dev

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

• Stripe: https://stripe.com

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

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

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

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

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

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

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

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

• Cursor: https://cursor.com

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

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

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

• Granola: https://www.granola.ai

• Wispr Flow: https://wisprflow.ai

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Alexander Embiricos:

• X: https://x.com/embirico

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Alexander Embiricos 

(05:13) The speed and ambition at OpenAI

(11:34) Codex: OpenAI’s coding agent

(15:43) Codex’s explosive growth

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

(33:11) The impact of AI on engineering

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

(45:40) Throwaway code and ubiquitous coding

(47:10) Shipping the Sora Android app

(49:01) Building the Atlas browser

(53:34) Codex’s impact on productivity

(55:35) Measuring progress on Codex

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

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

(01:02:53) Codex’s capabilities

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

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

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

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

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

—

Referenced:

• OpenAI: https://openai.com

• Codex: https://openai.com/codex

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

• Dropbox: http://dropbox.com

• Datadog: https://www.datadoghq.com

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

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

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

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

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

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

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

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

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

• Compiling: https://3d.xkcd.com/303

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

• Tesla: https://www.tesla.com

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

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

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

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

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

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

—

Brought to you by:

Vanta—Automate compliance. Simplify security.

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

Coda—The all-in-one collaborative workspace

—

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

—

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

—

Where to find Edwin Chen:

• X: https://x.com/echen

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

• Surge’s blog: https://surgehq.ai/blog

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Edwin Chen

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

(07:08) Building a contrarian company

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

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

(13:31) How Claude Code has stayed ahead

(17:37) Edwin’s skepticism toward benchmarks

(21:54) AGI timelines and industry trends

(28:33) The Silicon Valley machine

(33:07) Reinforcement learning and future AI training

(39:37) Understanding model trajectories

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

(42:55) Adapting to industry needs

(44:39) Surge’s research approach

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

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

(52:55) The story of founding Surge AI

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

—

Referenced:

• Surge: https://surgehq.ai

• Surge’s product page: https://surgehq.ai/products

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

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

• Sora: https://openai.com/sora

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

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

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

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

• Grok: https://grok.com

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

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

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

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

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

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

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

• Waymo: https://waymo.com

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

3. The Full Stack Builder model

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

5. Building specialized agents that critique ideas and find vulnerabilities

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Tomer Cohen:

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Tomer Cohen

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

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

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

(19:17) Building and customizing AI tools

(27:51) The timeline to launch

(31:46) Pilot program and early results

(37:04) Feedback from top talent

(39:48) Change management and adoption

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

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

(48:00) Challenges and specialization

(50:05) Finding talent

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

(56:43) Lightning round and final thoughts

—

Referenced:

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

• LinkedIn: https://www.linkedin.com

• Cursor: https://cursor.com

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

• Devin: https://devin.ai

• Figma: https://www.figma.com

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

• Windsurf: https://windsurf.com

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

• Lovable: https://lovable.dev

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

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

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

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

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

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

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

—

Recommended books:

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

2. The rise of the GTM engineer

3. A primer on segmentation

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Jeanne DeWitt Grosser:

• X: https://x.com/jdewitt29

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Jeanne DeWitt Grosser

(05:26) Defining go-to-market

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

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

(14:21) Implementing AI in sales processes

(15:28) Optimizing sales with AI agents

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

(26:04) When to hire a GTM engineer

(29:04) Hiring and scaling sales teams

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

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

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

(44:34) Vercel’s unfair advantage

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

(47:04) Innovative sales tactics at Stripe

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

(01:00:37) Segmentation strategies

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

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

(01:16:44) Sales compensation and hiring

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

—

Referenced:

• Vercel: https://vercel.com

• Stripe: https://stripe.com

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

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

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

• Gong: https://www.gong.io

• Lyft: https://www.lyft.com

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

• DoorDash: https://www.instacart.com

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

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

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

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

• Atlassian: atlassian.com

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

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

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

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

Also on Spotify and Apple Podcasts

Brought to you by:

Stripe—Helping companies of all sizes grow revenue

Vanta—Automate compliance. Simplify security.

Persona—A global leader in digital identity verification

Where to find Rachel Lockett:

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

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

Referenced:

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

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

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

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

• Coinbase: https://www.coinbase.com

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

• Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to

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

• Stripe: https://stripe.com

• Remind: https://www.remind.com

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

• Brex: https://www.brex.com

• Bridge: https://www.bridge.xyz

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

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

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

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

• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna

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

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

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

• Granola: https://www.granola.ai

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

• Loom: https://www.loom.com

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

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

Recommended books:

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

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

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

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

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

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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

We discuss:

1. Hyper-realistic work-like activities

2. The owner’s delusion

3. Utility curves

4. “Don’t make me think”

5. “We don’t sell saddles here”

6. Tilting your umbrella

7. When to pivot

—

Brought to you by:

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

Metronome—Monetization infrastructure for modern software companies

Lovable—Build apps by simply chatting with AI

—

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

—

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

—

Where to find Stewart Butterfield:

• X: https://x.com/stewart

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Stewart Butterfield

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

(06:44) Understanding utility curves

(10:13) The concept of divine discontent

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

(19:03) Tilting your umbrella

(28:32) Balancing friction and comprehension

(45:07) The value of constant dissatisfaction

(47:06) Embracing continuous improvement

(50:03) The complexity of making things work

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

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

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

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

(01:26:34) The owner’s delusion

—

Referenced:

• Slack: https://slack.com

• Flickr: https://www.flickr.com

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

• Blok: https://blok.so

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

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

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

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

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

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

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

• Six Sigma: https://www.6sigma.us

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

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

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

• We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d

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

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

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

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

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

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

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

• Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224

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Recommended books:

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

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

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

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

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

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Lenny may be an investor in the companies discussed.