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56:07ENBox Holds 100 Billion Files. Its CEO Says Enterprises Only Move for a 10xHost Nathan LabenzAaron Levie tells Nathan Labenz why AI excitement in the enterprise already outruns the early cloud — and why 98% reliability, seat-based SaaS, and incremental savings still will not ship.
1:24:48ENCanva's AI Features Have Been Used 10 Billion Times. The Playbook Is Not a Chat BoxHost Nathan LabenzJohn Milinovich, Canva's generative-AI product lead, walks Nathan Labenz through automation versus augmentation, concept-level interfaces, evals without a design arena, and why application-layer companies still have a decade of room.
54:45ENA Few Megabytes of Doom and a Few Gigabytes of Model: Why Runway Bets on GeneralizationHost Nathan LabenzCTO Anastasis Germanidis tells The Cognitive Revolution why video is a fuller record of the world than text, why physics shows up without being programmed in, and how a small lab competes with unlimited compute.
55:05EN400,000 Customers, 100 Million AI Tasks: Zapier’s CEO on Making Computers Do More WorkHost Nathan LabenzWade Foster tells Nathan Labenz how a no-code automation company absorbed LLMs, cloned its CEO with a prompt, and is trying to turn a DIY toolkit into packaged solutions.
2:03:55ENThe More You Constrain an Agent, the More You Can Trust ItHost Nathan LabenzAgent.ai engineering lead Andrei Oprisan tells Nathan Labenz why narrow, highly prescribed workflows beat open-ended autonomy — and how a 12-person team shipped a free agent network past 40,000 users in a few months.
1:50:08ENWaymo's Injury Rate Is Five Times Lower. It Still Loses to a Lyft.Host Nathan LabenzHuman drivers average one fatal crash per 100 million miles — and that bar still defines the self-driving debate.
46:47ENEditing Video Like a Document: How Descript Puts AI in the Copilot SeatHost Nathan LabenzDescript CEO Andrew Mason on Underlord, why the timeline had to die, and what a ten-times-more-expensive editor would look like.
1:03:22ENA 40-person team at $35 million ARR: HeyGen made AI avatars a business, not a demoHost Nathan LabenzJoshua Xu and Benchmark’s Victor Lazarte tell Nathan Labenz how a camera-replacement product grew past 40,000 business customers — and why half the faces on this episode are fake.
1:16:11ENScooping Food Into Boxes Is 70 Percent of Plant LaborHost Nathan LabenzChef Robotics CEO Rajat Bhageria on 20 million plated meals, a foundation model for food, and why the kitchen may leave the house.
1:12:41ENThe CEO Who Laid Himself Off Is Building a Business Operating SystemHost Nathan LabenzSiqi Chen of Runway tells Nathan Labenz why finance is a company-wide simulation, why chat boxes fail, and how a 100-person cap plus ambient intelligence is the real product strategy.
35:24ENScott Belsky: Models Are Commoditizing. Controls, Data, and Taste Are the MoatHost Jacob EffronAdobe’s chief product officer tells Unsupervised Learning why Project Neo leaking into Firefly, a three-second Premiere extend, and Superhuman-priced software all point to the same shift.
1:10:07ENSame Intelligence, 1% of the Price: Logan Kilpatrick on Gemini FlashHost Nathan LabenzA former OpenAI developer-relations lead, now the product manager for Google AI Studio, walks through what Gemini 1.5 Flash actually changes for builders.
58:28ENFrom Jailbreaking ChatGPT to Anthropic’s First Prompt Engineer: How Alex Albert Ships Claude 3Host Nathan LabenzA year after building jailbreakchat.com, Alex Albert walks Nathan Labenz through Claude 3’s writing, orchestration, character work, and the guardrails app developers still skip.
1:28:37ENTwelve Hours After a GPT-4 Demo, He Turned a Decade-Old Legal Startup AroundHost Nathan LabenzPablo Arredondo, co-founder of CaseText and now VP of CoCounsel at Thomson Reuters, traces legal research from 19th-century citators to a retrieval-anchored GPT-4 product that law firms treat more like a colleague than a search box.
52:41ENA Broken Belt Buckle Turned Gucci's Call Center Into a Sales FloorHost Jacob EffronSalesforce AI CEO Clara Shih on Service GPT, Einstein Copilot, and why trust—not cost—is the real bar to enterprise scale.
2:00:03ENPatients Rated GPT-4 More Empathetic Than DoctorsHost Nathan LabenzAzeem Azhar of Exponential View maps the AI S-curve for Nathan Labenz: why the past always looks flat, why empathy went first, and what a million times more compute would actually change.
1:12:40EN3% of Users Said an AI Friend Ended Their Suicidal Thoughts. Then Replika Made the Model Smarter.Host Nathan LabenzReplika founder Eugenia Kuyda on a Stanford study, why a smarter model felt like a stolen partner, and why relationship may be the real moat in consumer AI.
1:01:53ENCompanion Apps Open Twice as Often as TikTok. a16z Only Funds Weird but WorkingHost Nathan Labenza16z consumer partners Anish Acharya and Justine Moore walk Nathan Labenz through their Abundance Agenda for AI-native consumer apps.
4:56ENIf the Mind Is a Tool, AI Looks Less Like a ThreatHost Nathan LabenzYohei Nakajima and Nathan Labenz pause a TED AI talk to connect agent-building habits with East–West ideas of identity.
1:21:28ENThe Prompt Is a Bug: Suhail Doshi’s Bet on Control Over PixelsHost Nathan LabenzThe Mixpanel founder tells Nathan Labenz how a cloud browser, a canceled tweet, and a Thursday weight drop shaped Playground AI’s bet on images.
1:22:43ENFive billion minutes of calls: why Dialpad trained its own business LLMHost Nathan LabenzDan O’Connell on real-time speech, verticalizing the stack, and why he and Nathan Labenz disagree about when AI employees show up.
1:18:39ENThe GPT-4 Red-Teamer Who Got Unstuck by a Mediocre OutlineHost Nathan LabenzDan Shipper shows Nathan Labenz how to use ChatGPT as a copilot for thinking, not as a ghostwriter for his own voice.
1:15:39ENAfter 20 Years of Frontend, v0 Wrote Better Code Than Guillermo Rauch DidHost Nathan LabenzThe Vercel CEO tells Nathan Labenz why every product needs ghost text, why Software 2.0 will ossify the old stack, and why betting against open source is still the expensive mistake.
1:14:48ENDevDay Probably Created Thousands of Startups, Says OpenAI's Logan KilpatrickHost Nathan LabenzThe day after OpenAI's first developer conference, Dev Relations lead Logan Kilpatrick tells Nathan Labenz why thin wrappers were never companies, why agents were deliberately not shipped fully autonomous, and what $2 million custom models are for.
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