Lenny's Podcast: Product | Career | Growth

Fiona Fung leads the teams behind Claude Code and Cowork at Anthropic (overseeing Boris Cherny and the entire engineering and PM team). Before Anthropic, she spent 11 years at Microsoft building Visual Studio and TypeScript and then moved to Meta, where she started Facebook Marketplace (now generating over $100 billion in GMV annually), worked on Meta’s first smart glasses and AR glasses, and led infrastructure, growth, integrity, and safety teams at Instagram. She’s been an engineer for over 25 years and has a unique perspective on how the role of building software is changing.

In our in-depth conversation, we discuss:
1. What she’s learned about running a team that’s shipping 8x more code than before
2. Which roles AI will transform next
3. Specific ways her team uses AI
4. How Claude “routines” have changed how she operates as a manager
5. The context-switching problem no one has solved yet
6. The biggest unsolved problem in AI
7. What keeps her up at night
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
Mercury—Radically different banking, now with Command: https://mercury.com/
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Where to find Fiona Fung:
• LinkedIn: linkedin.com/in/fionafung
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Fiona Fung
(02:31) How the engineering role has transformed over 25 years
(09:28) What an AI-pilled software team looks like in 2026
(12:26) Using Claude to manage and review team output
(14:40) The evolution of code review and verification
(16:55) Who to hire: creative builders and deep systems experts
(18:18) The shift to ambitious thinking
(19:40) The growth mindset required to thrive in AI-native teams
(25:52) Helping small businesses adopt AI tools
(31:46) How Anthropic spots latent demand and builds for it
(35:08) The next frontier: asynchronous work with AI routines
(38:06) Agency and accountability in AI-native teams
(39:40) The vibe shift from token-maxing to ROI measurement
(44:24) The “bad vs. sad” quality framework
(49:34) Why all managers start as ICs at Anthropic
(55:24) Preventing skill atrophy
(58:43) Managing context switching with 20 AI agents running
(1:00:08) How PM and data science roles are transforming
(1:03:40) The importance of dogfooding and using your own product
(1:08:36) Outstanding questions
(1:12:48) The future of engineering jobs and education
(1:17:59) What keeps Fiona up at night: team culture at scale
(1:22:53) From six-month roadmaps to JIT (just-in-time) monthly planning
(1:27:03) Lightning round
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References: https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Mark Pincus founded Zynga—the company behind Words With Friends, FarmVille, and Zynga Poker—and has arguably created more hit consumer products than anyone in history. At Zynga, eight of 10 major game launches became massive hits, reaching over a billion players. Over the past five years, Mark has been synthesizing everything he’s learned about building successful consumer products and turning it into a book, Life at the Speed of Play, which comes out on June 23. This is the first interview he’s done about the book.

In our in-depth conversation, we discuss:
1. His “Proven, Better, New” framework: copy what’s proven, make it better so that 10 out of 10 people say “f*ck yes, I’ll use this”—then add something new
2. Why being less ambitious is the path to the most ambitious ideas
3. His rule of thumb that your instincts are right 95% of the time, but your ideas are wrong 75% of the time
4. “Kill hope before hope kills you”
5. How to raise kids in the age of AI
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Vanta—Automate compliance, manage risk, and accelerate trust with AI
—
Episode transcript: https://www.lennysnewsletter.com/p/the-common-pattern-behind-successful
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Mark Pincus:
• X: https://x.com/markpinc
• LinkedIn: https://www.linkedin.com/in/markpincus
• Website: https://www.lifeatthespeedofplay.com
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Mark Pincus
(02:46) The Proven Better New framework overview
(07:29) Earning the right to innovate
(08:30) What “better” really means
(12:03) Quick summary of the framework
(12:40) Examples of the framework in action
(13:30) How to use proven correctly on your platform
(15:13) The moral arbitrage of copying
(23:55) Be less ambitious
(28:25) The Bolt.new story and staying humble
(33:15) Kill hope before hope kills you
(37:00) Using AI as a failure machine
(40:08) Why Zynga’s games succeeded (it wasn’t virality)
(48:36) The future of consumer social apps
(57:05) How to know if your product is a B+
(1:01:25) Distribution in the age of AI
(1:15:39) Make everyone a CEO
(1:18:18) Stay close to the metal
(1:21:35) Why Mark says micromanagement is beautiful
(1:23:35) The expert witness
(1:25:05) The number one job of a CEO is to be right
(1:26:35) What Mark is teaching his five kids
(1:35:14) Mark’s “why”
(1:37:08) Mark’s new book: Life at The Speed of Play
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Referenced:
• Tribe.net: https://en.wikipedia.org/wiki/Tribe.net
• Zynga: https://www.zynga.com
• Sid Meier: https://en.wikipedia.org/wiki/Sid_Meier
• Electronic Arts: https://www.ea.com
• CityVille: https://en.wikipedia.org/wiki/CityVille
• Words With Friends: https://wordswithfriends.com/
• Scrabble: https://playscrabble.com
• Reddit: https://www.reddit.com
• TED Radio Hour, MIT Media Lab founder, 1984 TED talk.: https://www.ted.com/talks/nicholas_negroponte_5_predictions_from_1984
• Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel
• FarmVille: https://en.wikipedia.org/wiki/FarmVille
• Craig Newmark: https://en.wikipedia.org/wiki/Craig_Newmark
• How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier
• Angry Birds: https://www.angrybirds.com/
• OMGPop: https://en.wikipedia.org/wiki/OMGPop
• Draw Something: https://en.wikipedia.org/wiki/Draw_Something
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield
• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach
• Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan
• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong
• Jason Citron on X: https://x.com/jasoncitron
• Stanislav Vishnevskiy on LinkedIn: https://www.linkedin.com/in/svishnevskiy
• Jeff Bezos on X: https://x.com/JeffBezos
• Andy Jassy on X: https://x.com/ajassy
• Niantic: https://nianticlabs.com
• Pokémon Go: https://pokemongo.com
• Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon
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Recommended book:
• Life at the Speed of Play: Launch Products People Love!: https://www.amazon.com/Life-Speed-Play-Launch-Products/dp/0063352575/ref=tmm_hrd_swatch_0
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Tony Fadell created the iPod, co-created the iPhone, and founded Nest (which he sold to Google for $3.2 billion). He’s co-authored over 300 patents, was part of the legendary team at General Magic, and wrote one of the most important and inspiring books for builders, called Build.

In our in-depth conversation, we discuss:
1. The heated internal debates about whether the iPhone should have a physical keyboard
2. Why opinion-based decisions are essential for v1 products
3. Why marketing matters as much as the product itself, and how the iPod almost failed
4. Why voice will eventually become the primary interface with AI
5. Why cognitive surrender to AI is the biggest risk facing product builders today
—
Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny
—
Episode transcript: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Tony Fadell:
• X: https://x.com/tfadell
• LinkedIn: https://www.linkedin.com/in/tonyfadell
• Website: https://www.buildc.com
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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 Tony Fadell
(02:23) The Blackberry vs. iPhone keyboard debate
(07:50) Micromanaging vs. kind lies: what great products actually need
(15:57) The Nest thermostat and smoke alarm story
(21:22) How to decide what’s worth building: pain plus new technology
(27:36) The three-generation rule: why nothing works the first time
(34:20) The full customer journey: why marketing defines your product
(40:53) The power of storytelling and the press-release-first approach
(48:37) The evolution of product management and the builder role
(50:27) Why AI-generated code creates brittle, unmaintainable products
(58:00) Storytelling techniques
(1:05:45) The next iPhone
(1:13:15) Hardware is back
(1:17:01) What Tony is most excited about
(1:21:38) Working with Tony
(1:25:36) Ethics, morals, and the responsibility of product builders
(1:32:40) How to connect with Tony and Build Collective
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References: https://www.lennysnewsletter.com/p/father-of-the-ipod-and-iphone-on
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Benedict Evans is an independent analyst and former partner at Andreessen Horowitz, where he spent years as their in-house “thinker” tracking the most important technology trends. For the past six years, he’s been publishing deeply researched presentations on where tech is heading, most recently focused on AI’s transformation of the economy. His work is read by founders, investors, and operators trying to make sense of a noisy field. His most controversial opinion: AI is as big a deal as the internet or mobile—and only as big.

In our in-depth conversation, we discuss:
1. Why we’re in “1997” for AI—early, exciting, and deeply uncertain about what comes next
2. Where value will actually accrue in the AI stack
3. The anti-AI backlash, and where it may lead
4. The surprising boom in consulting and professional services at AI companies
5. Why distribution is becoming the ultimate moat as software gets easier to build
6. Why the right question about your job isn’t “What percent can AI do?” but “Is this a task or a job?”
7. Why things will probably be okay—and what you need to do to prepare
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny
—
Episode transcript: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Benedict Evans:
• LinkedIn: https://www.linkedin.com/in/benedictevans
• Newsletter: https://www.ben-evans.com/newsletter
• Website: https://www.ben-evans.com
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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 Benedict Evans
(02:19) What people aren’t pricing in about AI’s impact
(06:24) Why we’re in the 1997 moment of AI
(09:44) The unexpected boom in professional services and consultants
(17:44) Why distribution is becoming the ultimate moat
(23:17) The coming job transformation: what’s real vs. panic
(27:33) Why AGI definitions keep shifting
(38:11) Where value will accrue: models vs. applications
(42:55) Distribution wars: Google, Meta, Apple, and OpenAI
(48:12) The anti-AI sentiment and backlash
(53:11) How to raise kids in an AI future
(58:27) What jobs to steer toward or away from
(59:20) The question nobody’s asking about AI
(1:06:25) How to be successful in this coming future
(1:08:43) AI corner
(1:11:43) Lightning round
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Referenced: https://www.lennysnewsletter.com/p/a-rational-conversation-on-where
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com

Dan Shipper is the co-founder and CEO of Every, a media and software company that’s become a living laboratory for the future of work. Everyone at his company of about 30 people is an AI early adopter; from editors to ops people, they use AI to do much of their work, giving Every a unique lens into where the world is heading. A year ago on this show, Dan predicted that people were sleeping on Claude Code for nontechnical work, which proved to be remarkably prescient. Today he’s back with another set of calls: the SaaS apocalypse is dumb, CLIs are over, the forward deployed engineer is the most valuable new hire, and the only thing you need to do to stay employed is ride the models.

Dan’s predictions:
1. The future of work will happen inside Codex or Claude Code.
2. Every company will have one “super-agent” inside their Slack that every employee talks to regularly.
3. SaaS is not dead—in fact, Dan is bullish on SaaS stocks. His contrarian take: “I would buy SaaS stocks right now.”
4. SaaS economics will shift: users will bring their own AI tokens into apps, which actually improves SaaS margins.
5. PMs will thrive in the AI era.
6. Full-stack designers will become superheroes.
7. The AI job apocalypse is not happening.
8. Forward deployed engineer is the new most essential role.
9. CLIs are over.
10. Automation is a lie.
11. We will read way more AI-generated writing and we will like it.
12. We’ll be building software for humans and agents to use together.
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Brought to you by:
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny
Vanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny
—
Episode transcript: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
—
Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
—
Where to find Dan Shipper:
• X: https://x.com/danshipper
• LinkedIn: https://www.linkedin.com/in/danshipper/
• Podcast: https://every.to/podcast
• Website: https://danshipper.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 Dan Shipper
(02:56) Dan’s unique position living in the AI future
(09:17) How the way we work will change in the coming year
(16:39) The case for general agents
(18:08) Codex and Claude Code as the new operating system for work
(25:39) How Cursor fits in
(27:42) How this changes what SaaS companies should build
(31:13) Why CLI is already over
(33:34) Two agents are better than one
(36:22) Why Dan is bullish on SaaS stocks
(39:01) Why automation doesn’t reduce human work
(47:00) The value of human-written code
(48:36) Quick recap
(50:15) How work is changing
(56:17) Why data scientists are drowning in bad analysis
(58:24) Which product/tech roles are least changed by AI
(1:02:17) We will read way more AI-generated writing and we will like it
(1:08:28) Why product managers will dominate the AI era
(1:11:05) Full-stack designers are the other big winners
(1:13:11) The AI job apocalypse won’t happen
(1:16:00) How to “ride the models” to stay relevant
(1:21:02) Final predictions and advice
(1:25:24) Lightning round
—
References: https://www.lennysnewsletter.com/p/the-ai-paradox-dan-shipper
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
—
Lenny may be an investor in the companies discussed.


To hear more, visit www.lennysnewsletter.com