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

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—

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.

Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products.

We discuss:

1. What people think makes AI apps better vs. what actually makes AI apps better

2. What pre-training vs. post-training is, and why fine-tuning should be your last resort

3. How RLHF (reinforcement learning from human feedback) actually works

4. Why data quality matters more than which vector database you choose

5. Why high performers are seeing the most gains from AI coding tools

6. Why most AI problems are actually UX issues

—

Brought to you by:

Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/

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

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

—

Where to find Chip Huyen:

• X: https://x.com/chipro

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

• Website: https://huyenchip.com/

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

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction to Chip Huyen

(04:28) Chip’s viral LinkedIn post

(07:05) Understanding AI training: pre-training vs. post-training

(08:50) Language modeling explained

(13:55) The importance of post-training

(15:20) Reinforcement learning and human feedback

(22:23) The importance of evals in AI development

(31:55) Retrieval augmented generation (RAG) explained

(38:50) Challenges in AI tool adoption

(43:19) Challenges in measuring productivity

(45:20) The three-bucket test

(49:10) The future of engineering roles

(55:31) ML Engineers vs. AI engineers

(57:12) Looking forward: the impact of AI

(01:05:48) Model capabilities vs. perceived performance

(01:08:23) Lightning round and final thoughts

—

Referenced:

• Chip’s LinkedIn post on what actually improves AI apps: https://www.linkedin.com/posts/chiphuyen_aiapplications-aiengineering-activity-7358971409227792384-y0mf/

• Prediction and Entropy of Printed English: https://www.princeton.edu/~wbialek/rome/refs/shannon_51.pdf

• Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody

•Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord

• First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege

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

• Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill

• 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

• Stanford webinar—How AI Is Changing Coding and Education, Andrew Ng & Mehran Sahami: https://www.youtube.com/watch?v=J91_npj0Nfw

• 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

• 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

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

• Story of Yanxi Palace: https://www.imdb.com/title/tt8865016/

• Steve Jobs’s quote: https://www.goodreads.com/quotes/427317-remembering-that-i-ll-be-dead-soon-is-the-most-important

—

Recommended books:

• The Complete Sherlock Holmes: https://www.amazon.com/Complete-Sherlock-Holmes-Volumes/dp/0553328255

• AI Engineering: Building Applications with Foundation Models: https://www.amazon.com/AI-Engineering-Building-Applications-Foundation/dp/1098166302

• The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152

• From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765

—

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.

Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google.

We discuss:

1. Why most productivity metrics are a lie

2. Signs that your engineering team could be moving much faster

3. Why AI accelerates coding but developers aren’t speeding up as much as you think

4. AI’s impact on engineers getting into “flow”

5. Her framework for building and scaling a developer experience team

6. The three components of developer experience: flow state, cognitive load, and feedback loops

—

Brought to you by:

Mercury—The art of simplified finances: https://mercury.com/

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

Coda—The all-in-one collaborative workspace: https://coda.io/lenny

—

Where to find Nicole Forsgren:

• Twitter: https://twitter.com/nicolefv

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

• Website: https://nicolefv.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 Nicole Forsgren

(05:09) The concept of developer experience (DevEx)

(08:33) Flow state and cognitive load in the age of AI

(12:02) Challenges in measuring productivity with AI

(21:19) The importance of developer experience for business value

(22:20) Common issues and solutions in developer experience

(26:49) Signs your eng team is moving too slow

(29:52) How AI is improving productivity

(33:32) Real examples of productivity improvements

(36:35) Introducing her new book, Frictionless

(43:40) How to get started building a DevEx team

(45:15) The impact of forming developer experience teams

(46:15)  How to measure the impact of DevEx teams

(48:53) Measuring the impact of AI tools on productivity

(55:16) Survey design for developer experience

(57:59) Popular AI tools for developers

(59:08) Bringing a product mindset to DevEx improvements

(01:00:40) AI corner

(01:02:33) Lightning round and final thoughts

—

Referenced:

• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennysnewsletter.com/p/how-to-measure-and-improve-developer

• DORA: https://dora.dev/

• The SPACE framework: A comprehensive guide to developer productivity: https://getdx.com/blog/space-metrics/

• Measuring developer productivity with the DX Core 4: https://getdx.com/research/measuring-developer-productivity-with-the-dx-core-4/

• Gloria Mark’s website: https://gloriamark.com/

• Taking Flight with Copilot: https://dl.acm.org/doi/10.1145/3589996

• DevEx in Action: https://spawn-queue.acm.org/doi/10.1145/3639443

• CodeX: https://openai.com/codex/

• Devin: https://devin.ai/

• Abi Noda on LinkedIn: https://www.linkedin.com/in/abinoda/

• DX is joining Atlassian: https://getdx.com/blog/dx-is-joining-atlassian/

• GitHub Copilot: https://github.com/features/copilot

• 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

• Gemini Code Assist: https://codeassist.google/

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

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Love Is Blind on Netflix: https://www.netflix.com/title/80996601

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs

• Ninja Creami: https://www.amazon.com/Ninja-NC301-CREAMi-Containers-Bundle/dp/B0BLGR5JPV/

• Jura coffee maker: https://www.amazon.com/Jura-Nordic-Automatic-Coffee-Machine/dp/B0CF65BFZ1/

—

Recommended books:

• Frictionless: https://developerexperiencebook.com/

• DevEx Workbook: https://developerexperiencebook.com/#workbook

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

• Back Mechanic: https://www.amazon.com/Back-Mechanic-Stuart-McGill-2015-09-30/dp/B01FKSGJYC

• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/

• The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/dp/B01KBM82M4/

—

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.

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025.

What you’ll learn:

• How Dylan kept internal morale up after the Adobe acquisition fell through

• His approach to maintaining pace and a sense of urgency 13 years in

• How to systematically develop taste

• How Figma decides which product lines to add

• Why Dylan obsesses over “time to value”

• How AI is making design more valuable

—

Brought to you by:

Stripe—Helping companies of all sizes grow revenue

—

Transcript: ⁠https://www.lennysnewsletter.com/p/why-ai-makes-design-craft-and-quality-the-new-moat⁠

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175569466/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Dylan Field:

• X: https://x.com/zoink

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

—

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 Dylan Field

(03:58) The Adobe deal fallout

(05:50) Maintaining team morale post-deal

(09:13) Strategies for sustaining high performance

(13:37) Maintaining Figma’s unique company culture

(16:22) Dylan’s leadership evolution

(21:03) How to improve clarity as a leader

(24:40) The controversy behind FigJam

(31:06) Lessons from expanding Figma’s core product line

(39:32) Time-to-value

(45:14) Introduction to Figma Make

(48:26) AI app prototyping and the future of Figma Make

(53:38) Lessons from Figma’s AI product launch

(57:47) The importance of craft

(59:54) Developing good taste

(01:05:35) The future of product development

(01:10:32) Why AI won’t steal your job

(01:14:37) AI corner

(01:18:32) Lightning round and final thoughts

—

Referenced:

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

• Figma: https://www.figma.com/

• Adobe: https://www.adobe.com/

• Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor

• Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao

• $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz

• FigJam: https://www.figma.com/figjam/

• Cursor chat: https://help.figma.com/hc/en-us/articles/4403130802199-Use-cursor-chat-in-Figma-Design

• Figma Slides: https://www.figma.com/slides/

• Figma Sites: https://www.figma.com/sites/

• Figma Buzz: https://www.figma.com/buzz/

• Figma Draw: https://www.figma.com/draw/

• Figma Design: https://www.figma.com/design/

• Dev Mode: https://www.figma.com/dev-mode/

• Figma Make: https://www.figma.com/make/

• Zach Lloyd on X: https://x.com/zachlloydtweets

• Warp: https://www.warp.dev/

• Dylan’s post on X about Figma on an AI product leaderboard: https://x.com/zoink/status/1968588014935801884

• Kurt Cobain: https://en.wikipedia.org/wiki/Kurt_Cobain

• Damien Correll on LinkedIn: https://www.linkedin.com/in/damiencorrell/

• Marcin Wichary on LinkedIn: https://www.linkedin.com/in/mwichary/

• Loredana Crisan on LinkedIn: https://www.linkedin.com/in/loredanacrisan/

• Amber Bravo on LinkedIn: https://www.linkedin.com/in/amberbravo/

• Figma’s 2025 AI report: Perspectives from designers and developers: https://www.figma.com/blog/figma-2025-ai-report-perspectives/

• Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox#Energy_conservation_policy

• 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

• Pantheon: https://www.imdb.com/title/tt11680642/

• Retro: https://retro.app/

• Thiel Fellowship: https://thielfellowship.org/

—

Recommended books:

• Understanding Comics: The Invisible Art: https://www.amazon.com/Understanding-Comics-Invisible-Scott-McCloud/dp/006097625X

• The Spy and the Traitor: The Greatest Espionage Story of the Cold War: https://www.amazon.com/Spy-Traitor-Greatest-Espionage-Story/dp/1101904216

• Codex Seraphinianus: https://www.amazon.com/Codex-Seraphinianus-Anniversary-Luigi-Serafini/dp/0847871045

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:

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions.

—

What you’ll learn:

Why Google’s AI products are suddenly taking off after years of perceived stagnation 

How AI is expanding Search rather than replacing it, contrary to what many predicted 

The three core product principles that have helped Robby build multiple billion-user products 

Inside Instagram’s decision to build its own version of Snapchat Stories 

His mantra of “relentless improvement” 

How Google developed AI Mode from concept to launch in just one year 

Why most teams give up too early on potentially transformative products 

—

Brought to you by:

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

Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/

—

Transcript: https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year

—

My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation⁠

—

Where to find Robby Stein:

• X: https://x.com/rmstein

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

—

Referenced:

• Google Gemini: https://gemini.google.com/app

• Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image

• Chat GPT: https://chatgpt.com/

• Perplexity: https://www.perplexity.ai/

• Google Lens: https://lens.google/

• AI Google search: https://www.google.com/ai

• Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour

• Alex Rampell on X: https://x.com/arampell

• A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype): https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products

• Look broader, look closer, think younger: Tony Fadell speaks at TED2015: https://blog.ted.com/look-broader-look-closer-think-younger-tony-fadell-speaks-at-ted2015/

• Jobs to Be Done: https://www.christenseninstitute.org/theory/jobs-to-be-done/

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Rinstagram or Finstagram? The curious duality of the modern Instagram user: https://www.theguardian.com/technology/2016/sep/26/rinstagram-finstagram-instagram-accounts

• V03: https://v03ai.com/

• Pirate GPT: https://www.kickstarter.com/projects/silentmeditation/pirate-gpt/

• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f

• Dune on HBO Max: https://www.hbomax.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7

• Top Gun: Maverick: https://www.imdb.com/title/tt1745960/

• Purple pillows: https://purple.com/pillows

• Avocado pillow: https://www.avocadogreenmattress.com/products/green-pillow

• Justin Bieber’s website: https://www.justinbiebermusic.com/

• Scooter Braun’s website: https://scooterbraun.com/

—

Recommended books:

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612

• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654

• Aurora: https://www.amazon.com/Aurora-High-Stakes-Survival-Navigate-Darkness/dp/0062916475

• Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135202

—

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.