I dropped out of college and built a $3.6B company from scratch

**Sam Parr** (0:00)
Do you know what you're getting into here?

**Aaron Levie** (0:01)
Nope.

**Shaan Puri** (0:02)
Let me give you the simplest explanation. You know how on Twitter, you're funnier than the smart guys and then smarter than the actual funny guys? We did that in the business podcasting space.
By the way, I was supposed to be prepping for this podcast, and in the last hour, actually all I did was watch Millionaire Matchmaker Season 3 Episode 11, which, Aaron, if you remember, is when your co-founder went on Millionaire Matchmaker. And so, I don't have a whole lot of prep, but that was a great episode. Do you remember when he did that?

**Aaron Levie** (0:37)
I do, yes.

**Shaan Puri** (0:39)
Were you in support of that?

**Aaron Levie** (0:41)
Not exactly. So, we took a flyer on that one. They actually, well, the weirder story was they asked for both of us to do it. Somehow, I had better judgment, so.

**Shaan Puri** (0:51)
Sam, have you seen this episode?

**Sam Parr** (0:53)
Yeah, so I actually met your co-founder, Dylan, when I was starting my first company in San Francisco, I didn't have a lot of money, and we weren't making any money, and I did part-time work at a scavenger hunt company, and Box was a client one time, and so I got to hang out with him, and he had told me about being on the show.

**Aaron Levie** (1:10)
Wow, really?

**Sam Parr** (1:11)
By the way, we were at this bar at the end of the scavenger hunt at 7 p.m., and he pulled up his laptop and went to the back table and was working, and he couldn't enjoy the scavenger hunt.

**Shaan Puri** (1:22)
Well, I think that's one of the crazier things about y'all's story. You've been there for 20 years. It's kind of like four friends started in college type of deal.
Are all four still there now 20 years later?

**Aaron Levie** (1:35)
So three of us went to middle school and high school together, then four of us went to high school together. And we had tried lots of different ideas throughout middle school and high school. And then finally, as we went to college, kind of people split off to different schools. And then this idea kind of emerged, and we all kind of got back together on it, and then dropped out of college in kind of two parts in 2005 and 2006 And so we've just been working together for, I mean, honestly, like almost 30 years on different things, which is kind of crazy to think about at this point. So right now we have Dylan is CFO, he runs a bunch of functions in the company. He was famous for Millionaire Matchmaker, apparently, definitely his main claim to fame at this point. And then Jeff and Sam, Jeff has a bit of a farm.
He's kind of getting into the farm world. And then Sam is at Anthropic and on Claude, Claude Code. And he now is a constant thorn in my side because every three days, somebody says the CTO of Box left Box to go to Anthropic. But he actually retired from Box like six years ago.
But it causes unending viral fodder on that one.

**Sam Parr** (2:55)
That's pretty incredible that you can found a company, take it public, and then you go and work at Anthropic. Isn't the Instagram founder another founder?

**Aaron Levie** (3:04)
I mean, to their credit, they've done obviously an insane job on recruiting. So I think it might literally be a requirement to have been a CTO of a public company to work there at this point. But there's a list of like 10 of these people. Mike's over there, obviously now with Andre.
Sam, on our end, built some of the most important software and infrastructure that we run on to this day. So he's obviously a huge asset for them. But they've done an incredible job at recruiting.

**Shaan Puri** (3:37)
Dude, is it true, you, so you've been doing this for a long time. And the idea for Box, I think, was pretty simple. It's like, hey, you should be able to access your files wherever you are, not just on one computer. I think you guys started Consumer. And then, is it true there was sort of this like fork in the road moment where you guys went Enterprise and like, you know, kind of the co-founders had to debate it out. Is that how that went down?

**Aaron Levie** (4:01)
Yeah, I mean, it's always sounds way more dramatic, you know, in when we kind of compress it into the brief story. But it was a multi-month period of kind of like your classic wandering period that all startups kind of deal with where you don't know if you're going to pivot, you don't know if the business model is going to work, you don't know if you're going to get your next round of funding. Like, some things are clicking and working, some things aren't. And we had started, I would say, not even as a consumer or enterprise, we kind of started as agnostic to who the user would be. We just said, hey, you know, it should be, there should be a secure way to access your files from anywhere. Like, it was an obvious idea to us. And then what happened was it started growing, but consumers, we had this kind of, you know, very straightforward fork in the road. Consumers wanted to pay as little as possible, and they wanted a certain set of features that you'd have to go and build. Enterprises wanted to pay a lot more, but they would need like a hundred times more features. And as we kind of like thought about like, well, who do you focus on? We did eventually kind of conclude, you know, something really obvious in retrospect, and I can't like unsee it as they look at other people's strategies over time. These were just like totally different markets, like the enterprise needing to securely manage their most important data as an organization would require just a completely different set of functionality than what a consumer would need to back up their photos and access their music from anywhere. And those were just different markets, and there was different business models. One would pay like $5 a month, the other would pay maybe $5 million a year. And like completely different business models, different markets, different teams you'd have to build, different products you'd create. So we did eventually run into, you know, effectively a fork in the road, and after a few months of kind of debating it out and assessing the opportunities and, you know, people kind of having pretty different views on what to do, we eventually pivoted, you know, kind of very forcefully into the enterprise.