Trae Stephens: Why No Company is Successful Because of their VC | E1135

We don't have Monday partner meetings. Everything is super difficult to get through the investment team, and this is on purpose. The more process you have, the easier that it is to game the process to get to some mediocre outcome. The worst deals are the most competitive deals. They're the ones that are super consensus. It's very easy in retrospect to say, "Wow, we really let that get out of hand," but we're doing the same stupid stuff all over again.

Ready to go? Trey, I am so excited for this. So you've helped me with countless schedules for this show. I've wanted to make this one happen for a long time. So thank you so much for joining me today, Trey.

It's a pleasure to be here.

I would love to start with a bit of a weird one, but I wanna start childhood, and parents and teachers see a lot. How would your parents and teachers have described a young Trey?

(laughs) Oh, man. Uh, yeah, I- I mean, I grew up in the country. Like I, you know, lived in the woods in a log cabin that my dad literally built with his bare hands. Um, and I was kind of always this kind of misfit, I would say. Um, I- I love where I came from. I love Ohio. You know, it's- it's a wonderful place to be from. Um, and, you know, there was always this like tension that was like pulling me to escape. Um, and my- my... I have an older brother, he's 18 months older than me, and my mom used to say that she had one son that's like, you know, 18 going on 12, uh, being my older brother, and I was like, uh, 16 going on 40. Like I had this kind of old soul from the very beginning. Um, and, you know, I think that it's like I was the British version of an American teenager. Like I- I like-

(laughs)

... was like a 60-year-old in a, in a 16-year-old skin. Um, and, uh, I- I think like I just loved hanging out with adults. I loved sitting around and reading books. I loved like, you know, thinking about philosophy. Um, so I was... I- I would not say that I was like a super cool teenager (laughs) .

I mean, I... That has to be my favorite like phrase to enter, which is that the American teenager in a British body. Um, I- I- I do have to ask, I heard your entry to Georgetown, in particular, is a rather unique story of persistence. So how did you get into Georgetown, Trey?

You know, I was, uh, uh... I had, you know, great grades, great test scores. Like, you know, for all intents and purposes, it seemed like I was going to be able to kind of write my story for what I was going to do. But the problem was is I went to a rural public school in the middle of the country, and so it- it's like we don't really talk about this very much as a country, we're focused on other kind of social demographic problems. Um, but it turns out that like you just... it's basically impossible to get into good schools if your guidance counselor doesn't know all of the admissions officers at the Ivy League schools or whatever. Um, and so I sent out a bunch of applications. I think I applied to nine schools, and I got a lot of skinny envelopes back (laughs) . And, uh, I remember on the day that I got the skinny envelope back from five of the nine schools that I had applied to, uh, I went over to my high school girlfriend's house, and I was like, "Well, you know, at least the school that I got, I did get into is next to where you're going to go to school." And she was like, "Yeah, about that," and broke up with me the same day that, uh, that I had gotten rejected at all these schools. So I like went home and just laid on the couch with my face down, and my mom, uh, came over and she's like, "What do you wanna do? Where- where do you actually really wanna go?" And I said, "I wanna go to the School of Foreign Service at Georgetown." And she said, "Well then you're gonna go to the School of Foreign Service at Georgetown," and she put me on a flight and sent me to Washington DC and said, "Go convince the admissions office in person that they should let you in." And so I sat on the doorstep of the admissions office, demanding to see the dean, and eventually the dean came out and he's like, "Who is this crazy person that's loitering on my doorstep?" And I had a backpack full of recommendation letters, admittedly from people that I know now it's like they're probably not even reading these recommendation letters. It's like my, you know, high school cross country coach and things like that (laughs) . They basically just said like, "This is crazy that you flew out here with no plan other than to like demand to speak to me, um, and we're gonna put you on the top of the waiting list, and as soon as we like get the final decisions back from everyone about whether they're going to attend or not, you'll be the first person off the list." And so to my surprise, you know, like a couple of weeks later, I got a call from Georgetown and they were like, "All right. You're in. That was, that was a crazy stunt that you pulled." Um, the funniest part about this whole story though is that the... in my first week at Georgetown, I got, uh, invited to, uh, the president's office to have a meeting. And I thought like, "Wow, the president of the university is crazy," like he meets with every incoming freshman. Um, and so I go and meet with him and he's like, "No, I don't meet with every incoming freshman. I just heard your story from the dean of admissions" (laughs) . And he was like, "I needed to meet you. Obviously, you came from like a, you know, a- a middle class, lower middle class background. What's the financial situation here given your story?" And, uh, I said, "I'm taking a ton of debt." He said, "You know, I can't help you with financial aid, but I can give you a job in the president's office." And so I ended up working for the university (laughs) president all four years that I was in college. It was kind of like a crazy... It went from a bad situation like getting rejected to a situation where I was really set up to, you know, have a completely transformational life experience, uh, in very, very short order.