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

We discuss:

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

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

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

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Alexander Embiricos:

• X: https://x.com/embirico

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Alexander Embiricos 

(05:13) The speed and ambition at OpenAI

(11:34) Codex: OpenAI’s coding agent

(15:43) Codex’s explosive growth

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

(33:11) The impact of AI on engineering

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

(45:40) Throwaway code and ubiquitous coding

(47:10) Shipping the Sora Android app

(49:01) Building the Atlas browser

(53:34) Codex’s impact on productivity

(55:35) Measuring progress on Codex

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

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

(01:02:53) Codex’s capabilities

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

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

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

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

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

—

Referenced:

• OpenAI: https://openai.com

• Codex: https://openai.com/codex

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

• Dropbox: http://dropbox.com

• Datadog: https://www.datadoghq.com

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

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

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

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

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

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

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

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

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

• Compiling: https://3d.xkcd.com/303

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

• Tesla: https://www.tesla.com

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

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

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

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

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

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

—

Brought to you by:

Vanta—Automate compliance. Simplify security.

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

Coda—The all-in-one collaborative workspace

—

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

—

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

—

Where to find Edwin Chen:

• X: https://x.com/echen

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Edwin Chen

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

(07:08) Building a contrarian company

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

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

(13:31) How Claude Code has stayed ahead

(17:37) Edwin’s skepticism toward benchmarks

(21:54) AGI timelines and industry trends

(28:33) The Silicon Valley machine

(33:07) Reinforcement learning and future AI training

(39:37) Understanding model trajectories

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

(42:55) Adapting to industry needs

(44:39) Surge’s research approach

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

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

(52:55) The story of founding Surge AI

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

—

Referenced:

• Surge: https://surgehq.ai

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

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

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

• Sora: https://openai.com/sora

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

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

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

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

• Grok: https://grok.com

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

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

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

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

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

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

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

• Waymo: https://waymo.com

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

3. The Full Stack Builder model

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

5. Building specialized agents that critique ideas and find vulnerabilities

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Tomer Cohen:

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Tomer Cohen

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

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

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

(19:17) Building and customizing AI tools

(27:51) The timeline to launch

(31:46) Pilot program and early results

(37:04) Feedback from top talent

(39:48) Change management and adoption

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

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

(48:00) Challenges and specialization

(50:05) Finding talent

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

(56:43) Lightning round and final thoughts

—

Referenced:

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

• LinkedIn: https://www.linkedin.com

• Cursor: https://cursor.com

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

• Devin: https://devin.ai

• Figma: https://www.figma.com

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

• Windsurf: https://windsurf.com

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

• Lovable: https://lovable.dev

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

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

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

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

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

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

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

—

Recommended books:

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

2. The rise of the GTM engineer

3. A primer on segmentation

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Jeanne DeWitt Grosser:

• X: https://x.com/jdewitt29

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Jeanne DeWitt Grosser

(05:26) Defining go-to-market

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

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

(14:21) Implementing AI in sales processes

(15:28) Optimizing sales with AI agents

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

(26:04) When to hire a GTM engineer

(29:04) Hiring and scaling sales teams

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

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

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

(44:34) Vercel’s unfair advantage

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

(47:04) Innovative sales tactics at Stripe

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

(01:00:37) Segmentation strategies

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

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

(01:16:44) Sales compensation and hiring

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

—

Referenced:

• Vercel: https://vercel.com

• Stripe: https://stripe.com

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

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

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

• Gong: https://www.gong.io

• Lyft: https://www.lyft.com

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

• DoorDash: https://www.instacart.com

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

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

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

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

• Atlassian: atlassian.com

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

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

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

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

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

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

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

Also on Spotify and Apple Podcasts

Brought to you by:

Stripe—Helping companies of all sizes grow revenue

Vanta—Automate compliance. Simplify security.

Persona—A global leader in digital identity verification

Where to find Rachel Lockett:

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

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

Referenced:

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

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

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

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

• Coinbase: https://www.coinbase.com

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

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

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

• Stripe: https://stripe.com

• Remind: https://www.remind.com

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

• Brex: https://www.brex.com

• Bridge: https://www.bridge.xyz

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

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

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

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

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

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

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

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

• Granola: https://www.granola.ai

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

• Loom: https://www.loom.com

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

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

Recommended books:

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

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

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

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

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

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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

We discuss:

1. Hyper-realistic work-like activities

2. The owner’s delusion

3. Utility curves

4. “Don’t make me think”

5. “We don’t sell saddles here”

6. Tilting your umbrella

7. When to pivot

—

Brought to you by:

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

Metronome—Monetization infrastructure for modern software companies

Lovable—Build apps by simply chatting with AI

—

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

—

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

—

Where to find Stewart Butterfield:

• X: https://x.com/stewart

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Stewart Butterfield

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

(06:44) Understanding utility curves

(10:13) The concept of divine discontent

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

(19:03) Tilting your umbrella

(28:32) Balancing friction and comprehension

(45:07) The value of constant dissatisfaction

(47:06) Embracing continuous improvement

(50:03) The complexity of making things work

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

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

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

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

(01:26:34) The owner’s delusion

—

Referenced:

• Slack: https://slack.com

• Flickr: https://www.flickr.com

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

• Blok: https://blok.so

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

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

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

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

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

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

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

• Six Sigma: https://www.6sigma.us

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

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

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

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

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

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

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

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

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

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

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

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

—

Recommended books:

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

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

3. Why Fei-Fei believes AI won’t replace humans but will require us to take responsibility for ourselves

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

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

6. How to participate in AI regardless of your role

—

Brought to you by:

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

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

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

—

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

—

My biggest takeaways (for paid newsletter subscribers):

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

—

Where to find Dr. Fei-Fei Li

• X: https://x.com/drfeifei

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

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

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

(05:31) The evolution of AI

(09:37) The birth of ImageNet

(17:25) The rise of deep learning

(23:53) The future of AI and AGI

(29:51) Introduction to world models

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

(48:02) Introducing Marble, a revolutionary product

(51:00) Applications and use cases of Marble

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

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

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

(01:18:16) Conclusion and final thoughts

—

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

• Their process for building a “word-of-mouth machine”

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

• Why focusing on the “first 30 seconds” transformed their business

• Their approach to pricing that led to profitability within months

• How Grant thinks about building a durable “GPT wrapper” business

—

Brought to you by:

Vanta—Automate compliance. Simplify security.

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

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

—

Where to find Grant Lee:

• X: https://x.com/thisisgrantlee

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Grant Lee and Gamma

(05:59) The founding story of Gamma

(09:52) Achieving product-market fit

(15:43) Self-awareness as a founder

(17:17) The power of onboarding

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

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

(29:20) Sharing online

(37:40) Getting to $100M ARR

(41:19) Influencer marketing as a growth strategy

(54:08) Virality is not an accident

(58:30) Investing in brand before paid ads

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

(01:04:49) Prototyping and user feedback

(01:16:12) Adapting and moving quickly

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

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

(01:29:06) Pricing strategies

(01:34:53) Hiring philosophy and practices

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

1. Why the “mid-market” doesn’t exist

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

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

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

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

6. How to find and work with design partners

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

—

Brought to you by:

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

Lovable—Build apps by simply chatting with AI

Coda—The all-in-one collaborative workspace

—

Where to find Jen Abel:

• X: https://x.com/jjen_abel

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

• Website: https://www.jjellyfish.com

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Welcome back, Jen!

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

(08:08) Targeting tier-one logos

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

(15:35) The importance of high ACVs

(20:45)  Don’t play the small business game with an enterprise company

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

(28:11) Finding the right company

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

(43:21) The problem with channel partnerships

(44:41) Quick summary

(50:24) Hiring the right enterprise salespeople

(56:49) Structuring sales compensation

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

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

(01:07:31) Outbound tooling and AI

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

—

Referenced:

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

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

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

• Cursor: https://cursor.com

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

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

• Stripe: https://stripe.com

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

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

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

• Linear: https://linear.app

• Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu

• Gemini: https://gemini.google.com

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

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

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

• Deloitte: https://www.deloitte.com

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

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

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

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

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

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

• Clay: https://www.clay.com

• Apollo: https://www.apollo.io

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

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

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

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

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

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

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

—

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

—

Lenny may be an investor in the companies discussed.

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

We discuss:

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

2. The power of setting “crazy big goals”

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

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

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

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

—

Brought to you by:

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

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

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

—

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

—

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

—

Where to find Melanie Perkins:

• X: https://x.com/melaniecanva

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Melanie Perkins and Canva

(04:44) Building a “column B” company

(06:36) Operationalizing big visions

(13:13) Crazy big goals and celebrations

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

(26:30) Fundraising and investor rejections

(29:36) Leadership and growth lessons

(34:38) Canva’s goal-driven structure

(35:46) Balancing work and personal life

(38:02) Community-driven product development

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

(45:04) Canva’s biggest launch yet

(48:10) How Canva approaches product expansion

(52:37) AI integration in Canva

(53:56) AI corner

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

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

—

Referenced:

• Canva: https://www.canva.com/

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

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

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

• Figma: https://www.figma.com/

• Adobe: https://www.adobe.com/

• Calm: https://www.calm.com/

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

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

—

Recommended books:

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

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

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

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

—

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

Lenny may be an investor in the companies discussed.

Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO).

We discuss:

1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly

2. How the company measures AI productivity gains across technical and non-technical teams

3. Which teams are benefiting most from AI (it’s not engineering)

4. The boring organizational change that boosted productivity even more than AI tools

5. Why code quality has almost nothing to do with product success

6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily)

7. Lessons from building Google Wave, Google+, and other failed products

—

Brought to you by:

Sinch—Build messaging, email, and calling into your product: https://sinch.com/lenny

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

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

—

Where to find Dhanji R. Prasanna:

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Dhanji

(05:26) The AI manifesto: convincing Jack Dorsey

(07:33) Transforming into a more AI-native company

(12:05) How engineering teams work differently today

(15:24) Goose: Block’s open-source AI agent

(20:18) Measuring AI productivity gains across teams

(21:38) What Goose is and how it works

(32:15) The future of AI in engineering and productivity

(37:42) The importance of human taste

(40:10) Building vs. buying software

(44:08) How AI is changing hiring and team structure

(53:45) The importance of using AI tools yourself before deploying them

(55:13) How Goose helped solve a personal problem with receipts

(58:01) What makes Goose unique

(59:57) What Dhanji wishes he knew before becoming CTO

(01:01:49) Counterintuitive lessons in product development

(01:04:56) Why controlled chaos can be good for engineering teams

(01:08:07) Core leadership lessons

(01:13:36) Failure corner

(01:15:50) Lightning round and final thoughts

—

Referenced:

• Jack Dorsey on X: https://x.com/jack

• Block: https://block.xyz/

• Square: https://squareup.com/

• Cash App: https://cash.app/

• What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law#

• Goose: https://github.com/block/goose

• Gosling: https://github.com/block/goose-mobile

• Salesforce: https://www.salesforce.com/

• Snowflake: https://www.snowflake.com/

• Claude: https://claude.ai/

• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann

• OpenAI: https://openai.com/

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

• Llama: https://www.llama.com/

• Cursor: https://cursor.com/

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

• Top Gun: https://www.imdb.com/title/tt0092099/

• Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/

• Afterpay: https://github.com/afterpay

• Bitkey: https://bitkey.world/

• Proto: https://github.com/proto-at-block

• Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/

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

• Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch

• Google Wave: https://en.wikipedia.org/wiki/Google_Wave

• Google Video: https://en.wikipedia.org/wiki/Google_Video

• Secret: https://en.wikipedia.org/wiki/Secret_(app)

• Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth

• Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

• Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M

• Steam Deck OLED display: https://www.steamdeck.com/en/oled

• Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown

—

Recommended books:

• The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119

• Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/

—

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

—

Lenny may be an investor in the companies discussed.