About this episode

Aaron Levie discusses the current state of enterprise AI, its challenges, and future prospects.

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? (08:51) Tokenmaxxing & why your AI bill is about to explode (11:34) The myth of falling token costs and AI spend escaping IT budgets (17:37) The $5B startup hiding in AI compute…

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