The MAD Podcast with Matt Turck · 2026-05-28 · 1h 13m
Aaron Levie, co-founder and CEO of Box, returns to the MAD Podcast with the clearest read in tech on what AI is actually doing inside the world's largest enterprises right now - not the hype version, the real one. After hundreds of Fortune 500 CIO conversations this year, Aaron explains why we're still in "day one" of the agent era, why one badly written agent run can now cost $1,000 in compute, and why progress at the AI labs is paradoxically slowing enterprise deployment. We get into the token cost shock now reshaping IT budgets, why coding agents have reached escape velocity while the rest of knowledge work hasn't, the rise of headless software and what replaces per-seat pricing, the emergence of the forward-deployed engineer as the hottest job in tech, why Aaron thinks the AI doomers are wrong about jobs, and where startups can still win as the labs move up the stack. (00:00) Intro (01:18) Silicon Valley engineering vs. everyone else (05:35) Are enterprise CIOs actually bullish on AI?
Why NVIDIA Is Giving Away AI Models | Bryan Catanzaro81 / 100Cloudflare CEO: The Internet's Business Model Is DeadThe GPU Myth: State of AI Compute 2026 | Stephen BalabanOpenAI's Dan Roberts: Why AI Can Now Make DiscoveriesOpenAI's Yann Dubois: Why AI Progress Suddenly Feels Real