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The AI paradox: More automation, more humans, more work | Dan Shipper
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.—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—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
Latest Episodes
Why we’re at the beginning of the AI hardware boom | Caitlin Kalinowski (ex–OpenAI, Meta, Apple)
Caitlin Kalinowski was most recently at OpenAI helping build their robotics and hardware teams from scratch. Prior to that, she was head of AR glasses and VR hardware at Meta, where she led the teams building every generation of the Quest, Rift, and Orion, and was Meta’s first consumer electronics hire. Before this, she was technical lead on MacBook Air and Mac Pro at Apple, and helped engineer the original unibody MacBook Pro. She’s designed and engineered some of the hardest and most beloved consumer hardware products in history and is now focused on the next frontier: robotics.In our in-depth conversation, we discuss:1. VR—what happened?2. The coming memory price shock and why she’s telling startups to pre-buy now3. How the technologies built for VR became the foundation of modern warfare4. Why humanoid robots are still just prototypes, and what’s actually gating mass deployment5. Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman6. Why she left OpenAI—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Caitlin Kalinowski:• X: https://x.com/kalinowski007• LinkedIn: https://www.linkedin.com/in/ckalinowski• Website: https://www.caitlinkalinowski.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 Caitlin Kalinowski(02:32) Why VR didn’t take off despite incredible hardware(04:55) The future of AR glasses and physical AI(08:45) Why robotics and hardware are suddenly hot(13:33) Why humanoid robots aren’t ready yet(16:13) Supply chain bottlenecks threatening robotics(17:31) Why magnets and actuators are critical dependencies(20:51) The geopolitical implications of hardware supply chains(24:48) AI safety concerns with physical robots(26:50) Apple’s approach to hardware excellence(30:10) Building a hardware program from scratch at Meta(31:39) The Quest 2 cost reduction story(33:07) Critical principles for hardware development(39:58) The MacBook Air manila envelope moment(41:01) The butterfly keyboard situation(41:43) Lessons from Apple on customer feedback(44:46) The memory price crisis coming for hardware(49:31) How many components go into a robot(52:53) When to use off-the-shelf vs. custom components(55:02) How AI is changing hardware engineering(1:00:27) Why humanoids aren’t the answer for most use cases(1:03:05) When robots will build other robots(1:06:23) What makes a robot feel human and connected(1:09:15) Robots in the home(1:12:00) What the next five years look like(1:15:38) Why she left OpenAI(1:18:09) How to hire exceptional hardware teams(1:23:42) Lessons from Steve Jobs, Mark Zuckerberg, and Sam Altman(1:27:27) Failure corner(1:32:33) Lightning round—References: https://www.lennysnewsletter.com/p/why-were-at-the-beginning-of-the—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
How to build a company that withstands any era | Eric Ries, Lean Startup author
Eric Ries is the author of The Lean Startup, a book that reshaped how a generation of founders think about building companies. His new book, Incorruptible, explains how successful companies are destroyed by failing to protect what makes them valuable, and how to change it.In our in-depth conversation, we discuss:1. Why 80% of venture-backed founders are ousted within three years of going public2. The governance structures that protect companies like Anthropic, Costco, and Novo Nordisk3. The simple legal filing that takes two pages and could save your company4. Financial gravity: why successful companies predictably get corrupted into mediocrity5. Why mission-aligned companies like Anthropic reap major benefits from protecting their mission through governance6. Why success won’t protect you—it instead makes you a bigger target—Brought to you by:WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Eric Ries:• X: https://x.com/ericries• LinkedIn: https://www.linkedin.com/in/eries• Website: https://www.incorruptible.co• Newsletter: https://news.theleanstartup.com/• Podcast: https://ericriesshow.com• YouTube: https://www.youtube.com/@theericriesshow—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 Eric Ries(02:26) Introducing Incorruptible(06:26) Protecting what you’ve built(11:35) Why founders get ousted(14:58) Too early, too late(19:32) The blueprint: ethos plus integrity(20:49) Novo Nordisk’s 100-year governance fortress(26:41) The Vectura Group and Philip Morris(33:16) The “harder is easier” principle(37:22) Cloudflare’s mission emergence story(42:43) Groupon’s email frequency death spiral(45:37) How to define your purpose(51:09) Mission-driven vs. mission-hopeful companies(54:46) Integrity: structural and personal(57:47) Shareholder primacy: the 40-year-old “natural law”(01:00:04) Public benefit corporations: the easiest protection(01:04:24) Downsides and objections(01:06:08) The Anthropic example: fastest-growing company ever(01:08:39) The torchbearers in every organization(01:10:37) The culture bank: deposits and withdrawals(01:12:28) OpenAI and Anthropic governance(01:16:21) Mission guardians explained(01:18:29) Spiritual holding companies(01:21:53) The founder control trap(01:25:25) Three things to do this week(01:30:10) AI alignment and human alignment(01:34:00) Conway’s law: org charts in architecture(01:37:31) Book resources and farewell—References: https://www.lennysnewsletter.com/p/how-to-build-a-company-that-withstands—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
Why cultivating agency matters more than cultivating skills in the AI era | Max Schoening (Head of Product, Notion)
Max Schoening is head of product at Notion, where he’s been especially effective at getting designers and PMs to ship code, prototype in the terminal, and launch extremely successful AI products. He was previously a PM at Google, ran design at Heroku, was VP of Design (and a part-time engineer) at GitHub, and is a two-time founder. He’s one of the most AI-forward product leaders out there and one of the deepest thinkers on how AI changes how we build and use software.We discuss:1. What’s most worked in getting designers and PMs to embrace AI2. Why agency—not skills—is the thing that separates people who thrive from those who fall behind3. How the first 10% of every project is now “free,” and what that means for product development4. Max’s “tiny core” theory of great products: iPhone multitouch, the GitHub pull request, Notion blocks, Dropbox’s menu bar icon5. Why the SaaSpocalypse is overstated6. Why the amount of software has exploded but the quality hasn’t, and why that gap creates opportunity—Brought to you by:WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Max Schoening:• X: https://x.com/mschoening• LinkedIn: https://www.linkedin.com/in/max-schoening• Website: https://max.dev—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 Max Schoening(01:55) The origin story of designers coding at Notion(06:30) How much designers and PMs are shipping today(08:24) The balance between shipping code and strategic work(10:32) Why agency will help you thrive in the AI era(11:49) Examples of high agency at Notion(13:52) What we might lose as roles merge(15:56) Advice for developing agency(17:42) Malleable software explained(20:43) The Dieter Rams video and design philosophy(24:00) The SaaS apocalypse debate(28:25) How product building has changed in the past two years(30:27) What’s next in how we build products(34:16) Token spend and ROI conversations(37:39) Getting people to change how they work(39:04) Max’s AI stack(41:41) Which roles AI will transform next(44:26) When companies will start caring about ROI(48:38) Why Notion AI is so successful(51:47) How to ship more quickly while maintaining quality(56:40) Building taste through iterations(1:00:09) What matters most in building successful products(1:05:06) Using the jobs-to-be-done framework(1:07:28) Hot take on universal basic income(1:09:26) What Max would do with AGI(1:10:53) Contrarian corner(1:13:14) Failure corner(1:16:20) Advice for young people in Silicon Valley(1:19:20) Lightning round and final thoughts—Referenced: https://www.lennysnewsletter.com/p/why-cultivating-agency-matters-more—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
Snapchat CEO: Why distribution has become the most important moat | Evan Spiegel
Evan Spiegel, the co-founder and CEO of Snap, is one of the very few people in the world who has successfully built and scaled a lasting consumer social product. Snapchat has nearly 1 billion MAUs, and Evan and his team invented some of the most important consumer products and features, including Stories, AR glasses, swipe-based navigation, the camera as the primary UX, and a lot more.In our in-depth conversation, we discuss:1. Why distribution is now the biggest challenge for creating a consumer technology business2. How Snap innovates at scale with a 9-to-12-person design team: no titles, no hierarchy, hundreds of ideas reviewed weekly with the CEO3. Why a pure software business is no longer a moat, and what actually creates durable competitive advantages today4. How AI is changing the way designers work and why they’re now shipping code5. Why every major Snap feature was copied and how that forced the company to work differently6. Evan’s prediction that humanity’s comfort with AI will be a bigger bottleneck than the technology itself7. This year’s crucible moment for Snap—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyVanta—Automate compliance, manage risk, and accelerate trust with AI: https://vanta.com/lenny—Episode transcript: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Evan Spiegel:• X: https://x.com/evanspiegel• Snapchat: https://www.snapchat.com/@evan• LinkedIn: https://www.linkedin.com/in/evan-spiegel• Website: https://www.spiegelfamilyfund.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 Evan Spiegel(02:28) Why consumer social products are so hard to build(04:31) How Snapchat cracked distribution with close friends, not network size(05:50) Why distribution is the new moat in the AI era(08:39) Snapchat’s innovation track record (and why software isn’t a moat)(11:39) Why Snap is betting on two of the hardest businesses: consumer social and hardware(16:00) Specs use cases(17:56) The innovation process(21:34) The velocity of design work at Snapchat(25:07) Why Evan says you must talk to customers(26:06) The origin story of Stories(28:25) How screenshot detection saved early Snapchat(31:03) Why they waited to hire PMs—and what role they play now(34:41) How AI is shifting the designer-PM-engineer triad(36:10) Design as an intentional bottleneck for product cohesion(37:24) Why staying close to customers matters for any leader(39:39) What Evan looks for when hiring designers(41:57) How to develop young design talent(44:16) Designers shipping code with AI—and the guardrails needed at scale(47:20) Using jobs-to-be-done to organize AI transformation(48:50) How the CEO job has changed over 15 years(51:30) Learning to communicate(54:08) Why this year is Snapchat’s “crucible moment”(56:22) Being the “middle child” in tech(57:51) Screen-time philosophy with four kids (ages 2 to 15)(1:01:08) AI Corner(1:04:02) Contrarian Corner(1:06:04) Lightning round and final thoughts—References: https://www.lennysnewsletter.com/p/snapchat-ceo-why-distribution-is—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
How Anthropic’s product team moves faster than anyone else | Cat Wu (Head of Product, Claude Code)
Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind.We discuss:1. How Anthropic’s shipping cadence went from months to weeks to days2. The emerging skills PMs need to develop right now3. Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap4. Cat’s most underrated AI skill: asking the model to introspect on its own mistakes5. Why Claude’s personality is core to its success6. Why Anthropic’s mission alignment eliminates the friction that slows most large organizations7. Why “just do things” is the most important principle for working at AI-native companies—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVanta—Automate compliance, manage risk, and accelerate trust with AI—Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble—Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0—Where to find Cat Wu:• X: https://x.com/_catwu• LinkedIn: linkedin.com/in/cat-wu• Newsletter: https://catwu.substack.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 Cat Wu(01:29) Working with Boris Cherny(04:29) What Anthropic looks for when hiring PMs(06:18) How to help your teams move fast(08:58) How PRDs and roadmaps have evolved at Anthropic(10:28) The Mythos model and Anthropic’s shipping velocity(11:54) What happened with the Claude Code source code leak(12:53) Integrating with OpenClaw(14:19) How the PM team is structured at Anthropic(15:42) How engineer and PM roles are merging(17:54) Why product taste is the most valuable skill(20:10) Where human brains will continue to be useful(22:23) How to stay sane in constant chaos(24:16) What gets sacrificed when you ship so fast(27:47) The /powerup command(28:32) Why Anthropic has been so successful(32:28) When to use Claude Code vs. Desktop vs. Cowork(35:58) Tips for getting started with Cowork(38:44) Demo: Using Cowork to build slide decks overnight(41:48) Cat’s PM tech stack and internal tools(46:47) Which teams use the most tokens(51:15) The emerging skills PMs need for AI companies(55:00) Why building evals is underappreciated(58:44) Why Claude’s character and personality matter so much(1:00:44) How new models force product changes(1:05:11) The vision for Claude Code and Cowork(1:07:22) Advice for thriving in an AI-driven world(1:09:18) Why 95% automation isn’t good enough(1:11:58) Build apps you use every day, not prototypes(1:13:41) The divide between AI skeptics and believers(1:15:19) Lightning round—Referenced: https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves—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
