I dropped out of college and built a $3.6B company from scratch
My First Million
Hubspot
4.7 • 2.9K Ratings
🗓️ 2 July 2026
⏱️ 58 minutes
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| 0:00.0 | Do you know what you're getting into here? |
| 0:01.5 | 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. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel. By the way, I was supposed to be prepping for this podcast, |
| 0:23.6 | and in the last hour, actually all I did was watch Millionaire Matchmaker's season three, episode 11, |
| 0:29.0 | which Aaron, if you remember, is when your co-founder went on Millionaire Matchmaker. |
| 0:33.1 | And so I don't have a whole lot of prep, but that was a great episode. |
| 0:36.1 | Do you remember when he did that? |
| 1:34.4 | I do. Yes. Were you in support of that? Not exactly. So it was, we took a flyer on that one. They actually, well, the weird story was they asked for both of us to do it. Somehow I had better judgment, so. Sam, have you seen this episode? Yeah, but 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. 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 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? |
| 1:49.6 | So, three of us went to middle school and high school together, and 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 |
| 1:56.3 | back together on it and then dropped out of college in kind of two parts in 2005 and 2006. |
| 2:03.6 | And so we've just been working together for, I mean, honestly, like almost 30 years on different things, |
| 2:10.6 | which is kind of crazy to think about it at this point. |
| 2:13.6 | So right now we have, Dylan is CFO. |
| 2:16.6 | He runs a bunch of functions in the company. |
| 2:19.7 | He was famous for Millionaire Matchmaker. |
| 2:22.0 | Apparently, definitely his main claim to fame at this point. |
| 2:25.8 | And then Jeff and Sam, Jeff has a bit of a farm. |
| 2:29.1 | He's kind of getting into the farm world. |
| 2:31.0 | And then Sam is at Anthropic and on Claude, Claude code. And we, he now is a |
| 2:39.1 | constant thorn on my side because every, every three days somebody says the CTO of Box left |
| 2:44.0 | Box to go to Anthropic, but he actually, he actually retired from Box like six years ago. |
| 2:49.0 | And, but it causes like, you know, sort of unending viral fodder on that one. |
| 2:55.7 | That's pretty incredible that you can found a company, take it public, |
... |
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