In this episode, we sit down with Aaron Levie, CEO and co-founder of Box, for a wide-ranging conversation that’s equal parts insightful, technical, and fun. We kick things off with a candid discussion about what it’s like to be a public company CEO during times of volatility, and then rewind to the early days of Box — from dorm room experiments to cold emailing Mark Cuban and dropping out of college.

From there, we dive deep into how AI is transforming the enterprise. Aaron shares how Box is layering AI agents, RAG systems, and model orchestration on top of decades of enterprise content infrastructure — and why “95% of enterprise data is underutilized.”

We explore what’s actually working with AI in production, what’s still breaking, and how companies can avoid common pitfalls. From building hubs for document-specific RAG to thinking through agent-to-agent interoperability, Aaron unpacks the architecture of Box’s AI platform — and why they’re staying out of the model training wars entirely. We also dig into AI culture inside large organizations, the trade-offs of going public, and why Levie believes every enterprise interface is about to change.

Whether you're a founder, engineer, enterprise buyer, or just trying to figure out how AI agents will reshape knowledge work, this conversation is full of practical insights and candid takes from one of the sharpest minds in tech.

Box

Website - https://www.box.com

X/Twitter - https://twitter.com/Box

Aaron Levie

LinkedIn - https://www.linkedin.com/in/boxaaron

X/Twitter - https://x.com/levie

FIRSTMARK

Website - https://firstmark.com

X/Twitter - https://twitter.com/FirstMarkCap

Matt Turck (Managing Director)

LinkedIn - https://www.linkedin.com/in/turck/

X/Twitter - https://twitter.com/mattturck

(00:00) Intro

(01:51) Navigating uncertainty as a public company CEO

(14:48) The Box origin story: college, cold emails, and Mark Cuban

(23:39) Cloud transformation vs. the AI wave

(30:15) The reality of AI in the enterprise: proof of concept vs. deployment

(34:37) Inside Box’s AI platform: Hubs, agents, and more

(44:15) Why Box won’t build its own model (and the dangers of fine-tuning)

(51:51) What’s working — and what’s not — with AI agents

(1:04:42) Building an AI culture at Box

(1:13:22) The future of enterprise software and Box’s roadmap

Box’s Big AI Leap: Aaron Levie on Agents & the Future of Work

The MAD Podcast with Matt Turck