A $4B founder on the one thing holding back every AI agent

Aaron Levie (Co-Founder & CEO of Box) has run Box through three platform shifts: cloud, mobile, and now AI. In this episode of Navigator, Paul sits down with him in Redwood City to talk about what's actually changing as agents take over knowledge work. Aaron makes the case that most "AI problems" are actually context problems. Agents need access to the 90%+ of enterprise data that's unstructured, and giving them the right information in a tiny window of time and space is the real unsolved challenge. He also breaks down why there's a growing gap between model capability and real-world adoption, why the applied layer will stay valuable even as frontier models get more powerful, and why founders building today need to treat go-to-market as the new scarce resource now that building software is cheap. CHAPTERS: 00:00 — Cold open: agents use data like people do 01:00 — Welcome to Navigator, intro to Aaron Levie and Box 01:53 — Redwood City as the new AI hub 02:20 — 20 years of Box, three tech shifts, and the throughline 04:07 — Data vs. context: why this plays into Box's hand 05:18 — Unstructured data is 90% of the enterprise and was the hardest to automate 06:36 — The real bottleneck: context engineering in a tiny window of time and space 07:46 — The model overhang: capability is outpacing real-world adoption 09:14 — Why diffusion doesn't speed up just because models get better 10:35 — Why coding got the fastest AI takeoff, and what the real world is missing 11:45 — Silicon Valley vs. the real economy: a divide that may never close 14:01 — How Box customers are actually using AI: speed vs. net-new capability 16:24 — Rebuilding Box's own operating model around agents 19:15 — Headless SaaS and what happens when agents outnumber human users 21:39 — Frontier labs vs. the applied layer: lessons from the hyperscaler era 25:41 — Token costs, model routing, and why the applied layer is positioned to win 27:45 — Advice for founders starting a company today: go-to-market is the new moat Browserbase gives AI agents a browser to operate in. Navigator is our series of conversations with the people building the agentic future.