When I Was 17: Nathan Yates

Nathan takes the idea of remote working very seriously, posting up in the street in East Berlin.

Nathan Yates is the co-founder and CEO of We Roam, so one half of the reason I get to write this blog post from sizzling Split, Croatia. Before we started talking, Nathan mentioned that he thought he might be a terrible subject for this series, because he’s a real, live 10-year plan kind of person. But those interviews have been some of my favorites because of how divergent that is from my own experience. Nathan did in fact accomplish his teenage goal of becoming a corporate lawyer in New York. But he also left things open enough that he could jump into an opportunity like We Roam when it came along. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
An attorney. My parents and people in my life and friends had always said, “Oh, you’re definitely going to be an attorney.” I guess I thought critically - as much as a 17-year-old can think critically. A lot of people get told that because they like to argue, but I guess I knew that’s what I wanted.

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As a 17-year-old, I was very ambitious and competitive; I got a certain joy from being good at something. So when I was looking at careers, I looked at my skill set and decided, right or wrong, that I felt like I had the skill set to go to law school, go to a big international law firm in New York, and be at the top of the profession. And that appealed to me.
 
How did you decide to attend Lipscomb University? 
 
I wanted to go to Vanderbilt Law. Vanderbilt is a top 16, 17 law school which is important if you want to end up in New York at a big law firm, which I did. But it also has a reputation for being more collegiate and fun with fewer of the horror stories that you hear about everyone stealing each other’s notes and throwing each other under the bus.
 
I grew up in a very tiny town in the middle of nowhere in Michigan, so I had to hustle really hard to figure out how to get to a good school. Going to Vanderbilt undergrad was looking difficult, but there were certain schools in the area that were known to be good feeder schools to Vanderbilt Law. So I did pick my school based on that. And Nashville is great and I had some relatives in the South.
 
How did you choose your major? 
 
I majored in business management and minored in political science. As much as I knew I always wanted to go to law school, I’ve also always been super entrepreneurial, so I never pictured myself going to New York and working at a law firm for 20 years and becoming a partner. I saw corporate law at a high level as a steppingstone to doing my own thing or getting involved in a start up or an earlier stage company.
 
We didn’t have a lot of money growing up, so if I ever wanted anything extra I had to work for it. My parents definitely encouraged us to hustle, so I was doing two paper routes when I was 11, and I started a landscaping company and hired a bunch of neighbors. We had a mutual fund for college from my grandma, and I convinced my parents to let me use that to buy a house and flip it - I don’t know why my parents let us do that. My twin brother and I did all the manual work on our own, re-shingled the roof, did the plumbing, redid the sheetrock, and we flipped it. I worked at Taco Bell – best job I’ve ever had. I had a stint as a barista as well, which I think is a rite of passage for any millennial.
 
My major changed a number of times my first year. I was very interested in writing and literature and media stuff. There are a lot of history, literature, and philosophy majors who end up going to law school, so I felt like I had some flexibility there. I switched to business once it became more ingrained in my head that I wanted to eventually [work in] business.
 
How did you get from college to where you are now?
 
I’ve always been more interested in the entrepreneurial side of things, but I graduated in 2009 and the economy wasn’t great. People who were hitting the workforce straight out of college were having a rough time. That just reinforced my idea that if I went to graduate school, I could wait out the economy a little bit and get that one more degree. Also, if you do well in law school and you work hard, you kind of know you’re going to end up at a law firm. And once you’re there there’s a little bit of job security for the first three years. I thought I should add stuff to the resume while the economy recovered, and once I came out of it I’d have a somewhat better position. I felt like at the time it would have been hard to jump straight into business and accomplish the kind of things I wanted to accomplish.
 
I took the LSAT, which is a pleasure. I got some books and was self-taught about it, and I took 50, 60 practice tests, a lot. If your LSAT score is good enough you can overcome a lot of things, and if it’s not good enough it doesn’t matter how good everything else is. It’s worse than the bar in a sense of the pressure that you’re under. And at that age you’re not really equipped to deal with that.
 
I really loved law school; it was intense and high pressure and I liked that aspect of it. There are definitely 48 hours straight in the library, and months leading up to a test when you’re just processing so much information that you’re dreaming about it – it’s definitely a grind. But we also had a lot of fun. It was as advertised, a very collegiate experience.
 
After my first semester, I decided I wanted to get my MBA as well because they had a good joint JD/MBA program, and I knew I wanted to go back to business eventually. So I took the GMAT which meant I had to brush up on geometry and trig and algebra and stuff. I got in and ended up doing my program in four years instead of three years.
 
Basically your grades and where you fit in your overall class after your first year is the most important thing because then you apply for summer internships at places you hope to get an offer from after law school. I got a summer internship at a firm called Allen & Overy which is a big international firm. The summer before I graduated, I was there; I went to New York, fell in love with New York, and got an offer to stay. So my last year I knew where I was going to be, and it was a great feeling. I let myself relax and enjoy things a little bit for the first time. Played some golf, did some traveling, and just tried to let loose before starting the whole bar process.
 
Statistically it’s not hard to pass the bar on the first try if you go to a decent school. I think that the passage rate for people from Vanderbilt in New York is something like 88%. If you do the preparation and you don’t have a meltdown in your 6-hour handwritten test, then you’re fine. But getting yourself to a place where you can do that and not have a breakdown is hard. There was a girl next to me who was crying the entire time. And she finished her test. People are sprinting out because they’re getting sick, and a lot of people just don’t show up. They put a lot of mental strain on you.
 
Then the waiting. You prep, you get through it, you know you passed statistically, but you have to wait. Everyone always remembers where they were when they got their results. You don’t even know when they’re going to start coming out, and then all of a sudden people start texting, “Hey, did you get your results?” And then there’s this whole etiquette of whether you ask if someone passed, because it’s devastating if you don’t pass; it can change your whole career. Most firms give a second chance but some firms don’t, and you’re done, you’re fired after that. So it’s a lot of pressure. I don’t know that I’ve ever had a feeling of relief like when I found out I had passed.
 
I was doing corporate M&A [mergers and acquisitions], so the law firm I worked for had clients who are these big corporations, and they’re always buying and selling parts of companies. The lawyers are in charge of running that process. Our clients were huge, so these were $500 million and above transactions, so it’s a lot of paperwork. And you also have to do due diligence, so it’s a lot of reading through contracts and flagging things and then writing reports about it to the associates above you, so they can take it up.
 
I actually didn’t hate it. At first, anyway. It was exciting, there’s a lot of pressure, it’s very competitive between associates, you’re working crazy hours. And for someone like me that can be stimulating for six months, so I was loving it for a little bit. And then I started to not love it. There was some group dynamic stuff and culture stuff that I wasn’t really into. The beginning of the end is I started to get bored, which is a weird thing to say because I was working a ton, it’s high-pressure, but I always felt like I had this creative side and these management skills that I just wasn’t able to use, being a more junior person. Someone like me if I’m not engaged and I start getting bored, I worry about doing bad work. It would be really troubling for me to think that I was missing something important. Because if you miss something important, there are real dollar values. I didn’t feel sharp, so I thought, “I’ve gotta get out of here.”
 
Sean [We Roam co-founder and COO] moved to New York and we hit it off; we have a lot in common with hip-hop and sneakers and streetwear. So we would hang out and he kept mentioning to me, “Hey, I want to run a business idea by you.” It wasn’t a secret in our group of friends that I was looking for something, and people assumed that I probably brought something to a startup with the finance and law background, which I hope is true.
 
We talked about [We Roam] and I was very intrigued from the very beginning. I did some research and I thought it was a real opportunity. I loved that the whole industry was at such an early stage, so the idea of being able to shape it from the start and be a voice in an industry that I thought was going to be a movement was super appealing to me. So I said I wanted to get involved. To Sean’s credit, when you come up with an idea it’s very hard to give up any of that idea. But he saw that it would be valuable to bring me on and we became equal partners within 30 seconds of having that conversation, and the rest is history. I’m not sure, if roles were reversed, if I could have made the same decision.
 
I’ll be doing this as long as it’s there to do, and it probably won’t be in the same form, but I think We Roam has a lot more to do and a lot more to say. I’m trying to live in the moment. If something shifts, I feel like I’m a pretty flexible guy and I’ll adjust but I’d love for this to be it.
 
Looking back, what seems clear to you now? 
 
I was one of those people who put a lot of thought into college, and I focused on internships my entire college [career], I didn’t take any summers off. For me, I wanted to work for a big international law firm in New York at the highest level of the industry, and if you want something like that you have to plan ahead and you have to get those internships and you have to get those grades. If your goal is to start a business one day, you should be doing something to prepare yourself for that. Think about where you stand in the competitive landscape, and figure out how you can give yourself an edge. Think about what will make you a more compelling candidate, what skills you can pick up, and be strategic about it. You don’t have to figure out everything now, but you should be thinking about it.