The Rise of Agentic Commerce — Emily Glassberg Sands (Stripe)

Agentic commerce is no longer science fiction — it’s arriving in your browser, your development IDE, and soon, your bank statement. In this episode of The MAD Podcast, Matt Turck sits down with Emily Glassberg Sands, Stripe’s Head of Information, to explore how autonomous “buying bots” and the Model Context Protocol (MCP) are reshaping the very mechanics of online transactions. Emily explains why intent, not clicks, will become the primary interface for shopping and how Stripe’s rails are adapting for tokens, one-time virtual cards, and real-time risk scoring that can tell good bots from bad ones in milliseconds.We also go deep into Stripe's strategic AI choices. Drawing on $1.4 trillion in annual payment flow—1.3 percent of global GDP—Stripe decided to train its own payments foundation model, turning tens of billions of historical charges into embeddings that boost fraud-catch recall from 59 percent to 97 percent. Emily walks us through the tech: why they chose a BERT encoder over GPT-style decoders, how three MLEs in a “research bubble” birthed the model, and what it takes to run it in production with five-nines reliability and tight latency budgets.We zoom out to Stripe’s unique vantage point on the broader AI economy. Their data shows the top AI startups hitting $30 million in ARR three times faster than the fastest SaaS companies did a decade ago, with more than half of that revenue already coming from overseas markets. Emily unpacks the new billing playbook—usage-based pricing today, outcome-based pricing tomorrow—and explains why tiny teams of 20–30 people can now build global, vertically focused AI businesses almost overnight.StripeWebsite - https://stripe.comX/Twitter - https://x.com/stripe?Emily Glassberg SandsLinkedIn - https://www.linkedin.com/in/egsandsX/Twitter - https://x.com/emilygsandsFIRSTMARKWebsite - https://firstmark.comX/Twitter - https://twitter.com/FirstMarkCapMatt Turck (Managing Director)LinkedIn - https://www.linkedin.com/in/turck/X/Twitter - https://twitter.com/mattturck(00:00) Intro (01:45) How Big Is Stripe? Latest Stats Revealed (04:06) What Does “Head of Information” at Stripe Actually Do? (05:43) From Harvard to Stripe: Emily’s Unusual Journey (08:54) Why Stripe Built Its Own Foundation Model (13:19) Cracking the Code: How Stripe Handles Complex Payment Data (16:25) Foundation Model vs. Traditional ML: What’s Winning? (20:09) Inside Stripe’s Foundation Model: How It Was Built (24:35) How Stripe Makes AI Decisions Transparent (28:38) Where Stripe Uses AI (And Where It Doesn’t) (34:10) How Stripe’s AI Drives Revenue for Businesses (41:22) Real-Time Fraud Detection: Stripe’s Secret Sauce (42:51) The Future of Shopping: AI Agents & Agentic Commerce (46:20) How Agentic Commerce Is Changing Stripe (49:36) Stripe’s Vision for a World of AI-Powered Buyers (55:46) What Is MCP? Stripe’s Take on Agent-to-Agent Protocols (59:31) Stripe’s Data on AI Startups Monetizing 3× Faster (01:03:03) How AI Companies Go Global — From Day One (01:07:48) The New Rules: Billing & Pricing for AI Startups (01:10:57) How Stripe Builds AI Literacy Across the Company (01:14:05) Roadmap: Risk-as-a-Service, Order Intent, and Beyond

In this episode, Vercel CEO Guillermo Rauch goes deep on how V0, their text-to-app platform, has already generated over 100 million applications and doubled Vercel’s user base in under a year.Guillermo reveals how a tiny SWAT team inside Vercel built V0 from scratch, why “vibe coding” is making software creation accessible to everyone (not just engineers), and how the AI Cloud is automating DevOps, making cloud infrastructure self-healing, and letting companies expose their data to AI agents in just five lines of code.You’ll hear why “every company will have to rethink itself as a token factory,” how Vercel’s Next.js went from a conference joke to powering Walmart, Nike, and Midjourney, and why the next billion app creators might not write a single line of code. Guillermo breaks down the difference between vibe coding and agentic engineering, shares wild stories of users building apps from napkin sketches, and explains how Vercel is infusing “taste” and best practices directly into their AI models.We also dig into the business side: how Vercel’s AI-powered products are driving explosive growth, why retention and margins are strong, and how the company is adapting to a new wave of non-technical users. Plus: the future of MCP servers, the security challenges of agent-to-agent communication, and why prompting and AI literacy are now must-have skills.VercelWebsite - https://vercel.comX/Twitter - https://x.com/vercelGuillermo RauchLinkedIn - https://www.linkedin.com/in/rauchgX/Twitter - https://x.com/rauchgFIRSTMARKWebsite - https://firstmark.comX/Twitter - https://twitter.com/FirstMarkCapMatt Turck (Managing Director)LinkedIn - https://www.linkedin.com/in/turck/X/Twitter - https://twitter.com/mattturck(00:00) Intro (02:08) What Is V0 and Why Did It Take Off So Fast? (04:10) How Did a Tiny Team Build V0 So Quickly? (07:51) V0 vs Other AI Coding Tools (10:35) What is Vibe Coding? (17:05) Is V0 Just Frontend? Moving Toward Full Stack and Integrations (19:40) What Skills Make a Great Vibe Coder? (23:35) Vibe Coding as the GUI for AI: The Future of Interfaces (29:46) Developer Love = Agent Love (33:41) Having Taste as Developer (39:10) MCP Servers: The New Protocol for AI-to-AI Communication (43:11) Security, Observability, and the Risks of Agentic Web (45:25) Are Enterprises Ready for the Agentic Future? (49:42) Closing the Feedback Loop: Customer Service and Product Evolution (56:06) The Vercel AI Cloud: From Pixels to Tokens (01:10:14) How Vercel Adapts to the ICP Change? (01:13:47) Retention, Margins, and the Business of AI Products (01:16:51) The Secret Behind Vercel Last Year Growth (01:24:15) The Importance of Online Presence (01:30:49) Everything, Everywhere, All at Once: Being CEO 101 (01:34:59) Guillermo's Advice to Younger Self

Canva just announced $3 billion in ARR, 230 million monthly active users, and 24 million paying subscribers—including 95% of the Fortune 500. Even more impressive? They’ve been profitable for seven years while growing at 40–50% per year. In this episode, Canva’s Head of Engineering, Brendan Humphreys, reveals how he went from employee #12 to leading 2,300 engineers across continents, and why Canva’s “pragmatic excellence” lets them ship AI features at breakneck speed—like launching Canva Code to 100 million users in just three months.Brendan shares the story of Canva’s AI journey: building an in-house ML team back in 2017, acquiring visual AI startups like Kaleido and Leonardo AI, and why they use a hybrid of OpenAI, Anthropic, Google, and their own foundation models. He explains how Canva’s App Store gives niche AI startups instant access to millions, and why their $200M Creator Fund is designed to reward contributors in the AI era. You’ll also hear how AI tools like Copilot are making Canva’s senior engineers 30% more productive, why “vibe coding” isn’t ready for prime time, and the unique challenges of onboarding junior engineers in an AI-driven world.We also dig into Canva’s approach to technical debt, scaling from 12 to 5,000 employees, and why empathy is a core engineering skill at Canva. CanvaWebsite - https://www.canva.comX/Twitter - https://x.com/canvaBrendan HumphreysLinkedIn - https://www.linkedin.com/in/brendanhumphreysX/Twitter - https://x.com/brendanhFIRSTMARKWebsite - https://firstmark.comX/Twitter - https://twitter.com/FirstMarkCapMatt Turck (Managing Director)LinkedIn - https://www.linkedin.com/in/turck/X/Twitter - https://twitter.com/mattturck(00:00) Intro (01:14) Canva’s Mind-Blowing Growth and Profitable Journey (03:41) Why Brendan Left Atlassian to Join a Tiny Startup (06:17) What Being a Founder Taught Brendan About Leadership (07:24) Growing with Canva: From 12 Employees to 2,300 Engineers (10:02) How Canva Runs a Global Team from Sydney to Europe (13:16) Is AI a Threat or a Superpower for Canva? (15:22) The Real Story Behind Canva’s AI and Machine Learning Team (17:23) How Canva Ships New AI Features So Fast (19:19) A Tour of Canva’s Latest AI-Powered Products (21:03) From Design Tool to All-in-One Productivity Platform (26:21) Keeping Up the Pace: How Canva Moves So Quickly (30:22) The Future: AI Agents, Copilots, and Smarter Workflows (33:14) How AI Tools Are Changing the Way Engineers Work (35:47) Rethinking Hiring and Training in the Age of AI (37:01) Why Empathy Matters in Engineering at Canva (39:41) Building vs. Buying: How Canva Chooses Its AI Tech (41:23) Lessons Learned: Technical Debt and Scaling Pains (51:18) Shipping Fast Without Breaking Things (53:08) What’s Next: AI Video, New Features, and Big Ambitions