I dropped out of college and built a $3.6B company from scratch
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How did Box get started and why did the founders drop out of college?
Do you know what you're getting into here?
Nope. 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. Exactly.
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 three, 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? I do. Yes. Were you in support of that?
Yeah.
Not exactly. We took a flyer on that one. The weird story was they asked for both of us to do it. Somehow I had better judgment.
Sam, have you seen this episode?
Yeah. 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. I did part-time work at a scavenger hunt company and Box was a client one time. I got to hang out with him. and he had told me about being on the show wow really and by the way we were like at this bar at like the end of the scavenger hunt at like 7 p.m and he pulled up his laptop and went to the back table and was like working and uh he couldn't enjoy the scavenger hunt 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 you know started in college type of deal and are all four still there now 20 years later
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, 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 on 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 like, you know, sort of unending viral fodder on that one.
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?
I mean, they have, 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 they have this, there's a list of 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, you know, he's obviously a huge asset for them. But, you know, they've done an incredible job at recruiting.
Dude, is it true? 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?
Yeah, I mean, it always sounds way more dramatic, you know, 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.
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