In this interview, Robbie Crabtree explains the personal journey that led him to pursue a career in law. He describes an early fascination with understanding how systems work, noting that the U.S. legal framework governs many aspects of society and that lawyers write, interpret, and shape those rules. Initially, family expectations pushed him toward a business path, so he entered Haverford College as an economics major because the school lacked a traditional business program. The math‑heavy economics curriculum proved unsuitable, leaving him unhappy. He switched to his true passion—history—by convincing his parents that a history degree would be a stepping stone to law school, which also appealed to his father’s desire for a graduate credential. He recounts an alternative route he considered: attending the Naval Academy to play baseball, but rejected it because it would have required a long military commitment. Ultimately, his love for law, combined with a dislike for business studies, guided him to transition from economics to history and then to law school, setting the foundation for his current work as a lawyer and entrepreneur.
Chapters
How does a person answer why something happens?
When you look at the findings in different fields,
scant is the part of life in which we live
to attain the highest values.
So what drew me to the field of law originally was this idea that I wanted to know how things work. And I looked at the U.S. system, and everything is governed by laws. Laws are written by lawyers. They're then interpreted by judges who again. Are lawyers, most congresspeople are lawyers, most of our presidents are lawyers. So I said, you know what, there's something here. If I can understand the rules, I can start to figure out how to play the game in a more effective manner. That was really the beginning of what led me down the path of law. Ultimately, what was the big pusher to this field was when I went to college. And because I came from a family where my father was a vice president at a big Fortune 200 company and wanted me to go into business, I decided that I would be an economics major in college.
Mm-hmm.
Because my college was a very small liberal arts college, Haverford College. They didn't have a normal business degree. If you wanted to go into business, you took economics. But economics at Haverford is very math heavy. Math is not my subject. So I quickly realized in my first year that this was a terrible mistake. I was unhappy. I didn't enjoy it. There was no way I was spending the next 4 years focusing on this field. So I made the decision to switch my major to what I always wanted it to be, which was history. And the way that I finally sold my parents on letting me go the history route— because when you're a 19-year-old kid, you're still looking for mom and dad's approval. And I sold them with the understanding that, hey, I've always been interested in the law. What I'm going to do is just go to law school. And so I kind of sold them this idea of, hey, you're finally going to get your child to have a graduate degree, because my dad had 2 credits left to get his MBA and had always kind of regretted it but never really needed to go back. And so it was kind of this idea to him That resonated of, oh, I didn't get the graduate degree, but at least my son is. So it easily sold him on this idea of let me go the history route, let me go to law school, it'll be good for the family, it'll be good for me, and they agreed.
That's super interesting. Was it always part of the plan for you or did you just really want to do history and kind of focused only on that?
I mean, I think when you're 18, 19 years old, you don't really know what you want to do fully. Yeah. Like I said, I love the law side of things. I just didn't know if I wanted to go to law school. Because when I was originally applying to colleges, one of the big ones I was thinking of going to was the Naval Academy. Mm-hmm. I'd been offered a spot to play baseball there, but in talking to them about being a lawyer, it would've ended up being, I would've had to stay in the Navy until I was like 40 years old. And I said, that's not really what I want to do. So I had always kind of had it in mind, But when I started as an econ major, I was like, no, I won't go to law school. I'll just become a business person. I'll do the normal business thing. Life will be great. I'll live the normal, like, you know, middle to upper class American lifestyle. All will be good. But it wasn't until I realized I was miserable, and I always loved history. That was always my subject in high school growing up. I just loved history. So I quickly made that, that pivot because I realized econ and business, those were not the things for me at that time. We obviously see now, and I'm sure we'll get to this, I love the business side of performance speaking and being an entrepreneur and being a creator. But just to go into like a big company was not really appealing to me in that time. And so it was great to transition into this history degree and then ultimately into law school.
Yeah, yeah. Nate Cadillac and I talked about this on the last episode about how you don't You make a series of decisions that when you get to the point that you're at now, you can look back on those and be kind of like, well, I feel a little bit lucky that I made those choices at that point. Because you didn't— there wasn't actually an intent, you know, in that choice to get you where you are now. But it just kind of worked out like that. And I think that's true for most people, right? Yeah.
