Box’s Big AI Leap: Aaron Levie on Agents & the Future of Work
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How does Aaron Levie navigate uncertainty as a public‑company CEO?
I would argue that probably for 95% of our data, people have things that they would love to be able to do with that data that they just don't ever do. The thing that I get excited about agents is is the expansion of now what people can do with software and start to solve the use cases that we just never ended up prioritizing in most of these categories.
Welcome back to the Matt Podcast. Today we have a really fun conversation with Aaron Levy, the CEO of Box, a leading content and collaboration platform that powers over 100,000 organizations, and also a really insightful commentator on tech with over 2.5 million followers on X. In this conversation, we go deep into Box's AI efforts. Aaron shares how Box is layering agents, RAG, and model orchestration. We also talk about real AI adoption in the
Enterprise, I would say, is kind of crossing the chasm framework. We're in the ascent on the early pragmatist to the pragmatist side. Agents
to agents architecture. Why box is staying out of the model wars entirely? That is just a war that you want to ride the tailwinds of that, not play in that. And how to drive true AI culture inside.
A 2,000 person company. We have told everybody in the company that we want to use AI to be as productive as possible and aggressively use it across the business.
We also go into a bunch of fun stuff outside of AI, including Aaron's candid perspective on navigating volatile public markets. I
don't think we made it too hard to go public. Actually, it's good to have a heightened degree of scrutiny and regulatory pressure on being a public company. And we rewind
to the scrappy, improbable box.
Mark's origin story. We had like three or four meetings, rejected by everybody, complete with
Mark Cuban's
crucial early belief. I had emailed Mark Cuban. He got back to us in like 10 minutes. Please enjoy this great chat with
Aaron Levy. Aaron, welcome. Hello. So we we're going to dive into all things AI at box. Uh but before we do that, so we're recording this on April 8th. Yes. We need like a newspaper hostage
uh okay. This is when
this
happened, yeah.
A little bit of a of a crazy time and who knows what's gonna happen, you know, between now and the time we publish this. There's no chance this will be relevant by the time this gets published. I'm curious, um, as a public company CEO, uh not just uh, you know, uh tariffs, but um how do you navigate uncertainty and volatility in public markets? You've you've you've been a public company CEO for ten years now. Yeah. Do do you worry about uh the ups and downs of the stock price, or do you have such a long term view that it matters less?
Well, uh, depends on if I can decouple the stock price from s uh a more technical uh uh you know, actual issue that that we're dealing with. And so I would say I'm less worried about the stock price in the sense of moving because of of Wall Street trading up or down and any particular uh you know, for any p kind of particular reason, but uh very worried about about the embedded issue. That that might be related to that. So, you know, let's say sometimes it's self-caused. So we have to execute better in a particular area. And the stock price in those situations is just a another it's a symptom of the of the actual thing that you're dealing with. And it's your kind of like, you know, real-time KPI of of that problem.
And then in the case of tariffs, the thing that that you know scares the living, you know, heck out of me is just actually. The economic impact that this would this would have. So I don't really care about the stock price, you know, it per se. I care about the health of the country economically. And then obviously there's lots of follow-through that that would happen and ripple effect that would happen if if as of you know Tuesday uh afternoon, you know, the the tariffs that have been proposed, if those roll through, um uh, you know, this is gonna be a total disaster. So hopefully. Hopefully whenever this airs, we'll be able to look back in this and and you know, laugh and say, Ah, it was just an incredible negotiation gambit and it worked out and you know, we're all you know, trying to
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Chapters
8 chapters
1
How does Aaron Levie navigate uncertainty as a public‑company CEO?
0:00–10:58
2
What’s the story behind Box’s founding – dorm‑room experiments, cold‑emailing Mark Cuban and dropping out of college?
10:58–21:46
3
How does Box’s AI journey differ from the earlier cloud transformation?
21:46–31:15
4
What’s the reality of AI adoption in the enterprise – proof‑of‑concept vs production deployment?
31:15–40:39
5
What are the main components of Box’s AI platform – hubs, agents, RAG and model orchestration?
40:39–53:57
6
Why does Box stay out of the model‑training wars and avoid fine‑tuning its own model?
53:57–1:06:47
7
What’s working and what’s still broken with AI agents at Box?
1:06:47–1:15:14
8
What does success look like for Box’s AI roadmap and the future of enterprise software?
1:15:14–1:15:39
Speakers
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