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1:13:48EN
Unsupervised Learning: With Jacob Effron· Jul 16, 2026PodcastCarriers Spend $200 Billion a Year. The Money Went Up the StackHost Jacob EffronBenedict Evans tells Jacob Effron why analogizing AI to past platforms is a dead end, and why looking at how those platforms actually made money is not.
57:37ENUnsupervised Learning: With Jacob Effron· Dec 10, 2025PodcastThe hot-swap era for models is over, OpenAI's enterprise product chief saysHost Jacob EffronOlivier Godement on GPT-5.1, Codex, enterprise harnesses, and the three practices that actually make AI land inside large companies.
44:21ENUnsupervised Learning: With Jacob Effron· Jun 4, 2025PodcastMercor's CEO: Knowledge Work's Next Job Is Writing EvalsHost Jacob EffronBrendan Foody tells Redpoint how Mercor turned AI hiring and expert data into a $100 million round — and why he thinks a huge slice of white-collar work will become creating tests for models.
51:08ENUnsupervised Learning: With Jacob Effron· Apr 15, 2025PodcastThe Transformer Co-Author Who Says Scaling Hit a WallHost Jacob EffronCohere CEO Aidan Gomez tells Redpoint that a $100 million model is still an amnesiac genius, and that enterprise AI money is concentrating in support, research, and the back office.
1:04:54ENUnsupervised Learning: With Jacob Effron· Nov 12, 2024PodcastHe bet company equity that Transformer would last — then drew an AI map for 12,000 companiesHost Jacob EffronDatabricks chief AI scientist Jonathan Frankle tells enterprises when to prompt, fine-tune, or pre-train, and why he still refuses to forecast the next architecture.
56:10ENUnsupervised Learning: With Jacob Effron· Oct 29, 2024PodcastDeepL Beat Google at Translation by Refusing to Be a General ModelHost Jacob EffronOnly 18 percent of the world speaks English—and a Cologne startup turned that fact into a $2 billion language-AI company.
52:41ENUnsupervised Learning: With Jacob Effron· Mar 6, 2024PodcastA 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.
54:44ENUnsupervised Learning: With Jacob EffronPodcastLegal Tech's Step-Function Moment: Why Legora Bet on the Last 20%Host Jacob EffronLegora CEO Max explains the $550M Series D, AI-native legal work, foundation-model competition, and the culture required to keep moving fast.
1:01:47ENUnsupervised Learning: With Jacob EffronPodcastInside Notion AI: Prototypes That Annoy Everyone, Evals Built In-House, and Models Rented from PartnersHost Jacob EffronNotion AI engineer Linus Lee explains how a dozen-person team went from a hotel-room hackathon to Writer, Autofill and workspace Q&A.
51:30ENUnsupervised Learning: With Jacob EffronPodcastLess Email, Better Thinking: Grammarly’s CEO on AI That Augments CommunicationHost Jacob EffronGrammarly CEO Rahul explains how the company is moving from grammar checks to end-to-end communication assistance—and why evals, user data, and measurable outcomes matter.
1:04:25ENUnsupervised Learning: With Jacob EffronPodcastInside GitHub's Copilot Bet: Agents, Open Source, and Why the Developer Job EnduresHost Jacob EffronGitHub CEO Thomas explains how Copilot went from a research bet to 1.3 million developers, and what agents, fine-tuning and a multi-model world mean for the next five years of software.
57:08ENUnsupervised Learning: With Jacob EffronPodcastShipping Finn: Intercom's Product Playbook for the ChatGPT EraHost Jacob EffronDes Traynor explains how Intercom pivoted to AI, shipped Finn, built guardrails, and turned customer support into a product lab for LLMs.
1:09:00ENUnsupervised Learning: With Jacob EffronPodcastThe Meeting Is the Moat: Fireflies.ai’s Path to 16 Million UsersHost Jacob EffronKrish Ramani explains how Fireflies.ai turned AI note-taking into a meeting chief of staff, why he avoids fine-tuning, and how a startup competes with Microsoft, Zoom, and Google.
1:04:35ENUnsupervised Learning: With Jacob EffronPodcastOscar Health's AI Playbook: Translate the Bureaucracy First, Then Reinvent CareHost Jacob EffronMario, Oscar Health's CTO and co-founder, explains how a regulated insurer deploys LLMs today and what stands between healthcare and AI doctors.
54:05ENUnsupervised Learning: With Jacob EffronPodcastServal's Jake Stout on Outbuilding ServiceNow: Mirror the System of Record, Bet on Code, and Ship Before the Incumbent Can Book a MeetingHost Jacob EffronHow an AI-native employee-support startup attacks a legacy ITSM incumbent with velocity, code-generated workflows and a permissions-first architecture.
57:25ENUnsupervised Learning: With Jacob EffronPodcastFrom RAG to Reasoning: Why the Future of AI Is a System, Not a ModelHost Jacob EffronDouwe Kiela explains what OpenAI's o1 reveals about test-time compute, why enterprise AI must be specialized, and where post-training and evaluations are heading.
51:55ENUnsupervised Learning: With Jacob EffronPodcastThe Search Engine Under AI Apps: Why Bigger Context Windows Aren't EnoughHost Jacob EffronTurbopuffer CEO Simon on object-storage databases, vector-search trade-offs, and the AI features that will become SaaS table stakes.
44:53ENUnsupervised Learning: With Jacob EffronPodcastLegora's CEO on Building Legal AI That Survives the Next Model ReleaseHost Jacob EffronMax explains how Legora turns fast-moving model capabilities into end-to-end legal work, enterprise adoption, and a durable product strategy.
51:45ENUnsupervised Learning: With Jacob EffronPodcastCameras Optional: HeyGen's Joshua Xu on Avatars, Orchestration and Building Ahead of the ModelsHost Jacob EffronHeyGen co-founder and CEO Joshua Xu explains how AI avatars are replacing the camera for business video, and how the company handles quality, trust and safety, and capital.
46:48ENUnsupervised Learning: With Jacob EffronPodcastSnowflake's AI Stack: Small Models, the Text-to-SQL Iceberg, and Why Governance Comes FirstHost Jacob EffronSnowflake head of AI Baris Gekken explains how Arctic and Cortex were built, where enterprise AI actually works today, and why precision, governance and evaluation matter more than raw model capability.
45:00ENUnsupervised Learning: With Jacob EffronPodcastAgents Everywhere: OpenAI's Blueprint for Tool Use, Evals, and Computer-Use InfrastructureHost Jacob EffronOpenAI's API platform team explains how agents are moving from deterministic workflows to reasoning-driven tool use, and what developers still lack.
54:52ENUnsupervised Learning: With Jacob EffronPodcastCoding Agents Are Breaking Containment: The 2026 AI Stack, the Coding Wars, and the Next FrontierHost Jacob EffronJacob Effron and Swyx map the state of AI engineering, from agent harnesses and infrastructure churn to coding-market economics, open models, dark factories, and world models.
1:01:13ENUnsupervised Learning: With Jacob EffronPodcastPinecone's Vector Database Bet: Scaling Through the ChatGPT TsunamiHost Jacob EffronEdo Liberty explains how Pinecone scaled through the generative AI boom, why vector search is more than a database add-on, and where he sees the next AI infrastructure shifts.