The Real Lawyer: Daren Stanaway (Part 1)

In this episode, Daren Stanaway reflects on her path from growing up in Billings, Montana, to attending Harvard for both undergrad and law school. Initially drawn to journalism, Daren’s deliberate approach to her career led her to law, where she envisioned “making news” instead of just reporting it. She shares memories of her time at Harvard Law School, from the rigor of 1L year to the camaraderie she built with classmates, and her involvement in the law school a cappella group, The Scales of Justice. Daren’s reflections reveal the discipline, determination, and adaptability that defined her early professional years and positioned her for success in litigation.

Transcript

Joyce Sophia Xu (00:03.726)
Welcome to the Real Lawyer podcast, where we get real about life, working in law, and everything in between. I'm your host, Joyce Sophia Hsu, and our guest this week is Darren Stanaway, Associate General Counsel at Interactive Brokers in Washington, DC.

fortunate enough to work with Darren while we were both at Paul Hastings. I think it's been mentioned before that I myself have been a corporate lawyer for over 24 years. I specialize in derivatives transactions. I started out at Davis Polk in New York and then I went on to run derivatives practices at Simpson Thatcher and Paul Hastings. The thing I really love about my work is that the structures and the products we work on

are constantly evolving. So it's an area that is full of creativity. And new issues come up all the time, and they relate to different areas of the law. It could be capital markets, could be credit, could also be &A, bankruptcy, ERISA, bank regulations, broker dealer regulations, etc. So because of that, I got to work and collaborate with

literally hundreds of lawyers in other departments. And one of these colleagues I worked with very closely was Darren Stanaway. I still remember the day Darren knocked on the door of my new office at the MetLife building at Paul Hastings. I had just joined the firm to start a new practice there in derivatives. And Darren was in New York. She's based in DC. So she was in New York on a business trip.

and she came by to introduce herself. She was enthusiastic and confident and brilliant. And from that day on, we worked on many projects together and I loved every minute of it. So I am beyond delighted to have Darren on the Real Lawyer podcast. In this first part of our conversation, Darren shares a lot of the great memories she had from law school.

Joyce Sophia Xu (02:20.765)
and also from her early years as a young litigation associate. I hope you enjoy.

Joyce Sophia Xu (02:32.237)
Hi, Darren. Welcome. Hi. Thanks, Joyce. I'm happy to be here. Thanks so much for the invitation. Thanks so much for coming on the show. I'm looking forward to having a fun conversation with you. Likewise. Great. So let's get started. I first want to talk about law school. You went to Harvard for both undergrad and law school. I'd love it if you could share with us how you grew up and what led you to law school.

Sure, happy to, Joyce. So I grew up in a very, very Western state, way out in Montana. I was born and raised there, went to public high school in Billings, Montana, my hometown. And growing up, I was always very interested in music and theater and performing arts, and ultimately thought I wanted to go into

broadcast journalism. I watched Barbara Walters and Jane Pauli on Dateline in 2020 every week, even from a very young age, and really admired what they were doing. And that was the path that I originally thought I was going to follow. I even interned in high school as an intern reporter at our local NBC affiliate and really thought I wanted to be a broadcaster.

So going into college, I was looking at colleges and thinking, do I want to make a lifetime commitment now at age 17 to be a broadcast journalist? And I ultimately decided, although I was pretty sure that's what I wanted to do, that perhaps at 17, I shouldn't make such a big life decision and should select a college where I could still go that route, but wouldn't necessarily be wedded to it if I decided during the midst of college to pursue something differently.

So I thought a lot about going to Northwestern or USC, which have tremendous broadcast journalism programs, but ultimately decided to go to Harvard undergrad because I knew that I could still pursue broadcast journalism going there, but I wouldn't necessarily be limited to that if I wanted to do something else. And so about my junior year in college, I started thinking really hard about what I was going to do after college and whether I really wanted to pursue broadcast journalism.

Joyce Sophia Xu (04:47.309)
or something else. And I realized that as much as I loved journalism itself, that there were a lot of factors that made me think maybe that wasn't the best path for me. The first one was that I knew that I really wanted to go to a big urban center. Having grown up in Montana, it was a wonderful place to grow up. But I knew that I wanted to be somewhere.

where there were a lot more professional opportunities both for whatever I decided to go into, but potentially for journalism as well, which would be something like New York or DC, perhaps Los Angeles. And after that point, I thought, well, what else would I want to do if it wasn't journalism? And I decided I wanted to pursue law because...

I wanted to be the one sort of making news headlines, so to speak, as opposed to reporting on what other people were doing, which is fascinating, but I wanted to be the one making those things that got reported. So that was kind of what ultimately catalyzed my decision to take the LSAT and go to law school in the first place. So I took it quite early. I took the LSAT my junior year. And then when I...

got into Harvard Law School. I loved my time there and was thrilled that I got to stay for another three years. So as they say, I was on the seven year plan. I spent seven straight years at Harvard, went straight through and haven't looked back since. So that was how I decided to land on law school. You know what's funny? I also had an interest in music and wanted to get into broadcast journalism when I was like a little girl.

but then I had to come to the States and learn a new language. And I thought, you know, no way I could be a journalist now. It sounds like for you, you were just very thoughtful and deliberate with your choices. so I'm curious, did you also seek out people to talk to, to get advice from, was there any particular conversation with someone that helped you make the decision?

Joyce Sophia Xu (06:51.178)
I think for the most part, I had a pretty good sense that that was what I wanted to do. I of course talked to some other then law students when I was an undergraduate and got their insights and thoughts on what law school was like. And I thought it sounded like a great opportunity. And also just you have a clear career path, right? Coming out of law school, you get to be a lawyer straight off. Yeah.

And did you know, did you have an idea as far as the kind of law that you wanted to get into? Or did you have any idea about corporate versus litigation or public interest versus private sector? I had only a vague idea. I knew that I wanted to do so as it was presented to me at the time when I was interviewing for law firms, most of the law firms had a bifurcation between corporate

and litigation. Now I subsequently learned that those are two very overly large buckets that many, different facets. But of the two, I thought litigation sounded very fascinating. Being in the courtroom writing legal briefs, that was certainly the law that I was just generally more familiar with. And I do not enjoy particularly writing contracts. So that was sort of the but.

sort of high level idea of what corporate law was. Now, again, this is someone who had no idea at the time what it was to actually be a lawyer, but I thought writing briefs sounds a lot more fun than writing contracts. So I think I'm interested in litigation. And that's why I went into litigation. Wow. Yeah, you know, there's, I think there's something to that. Whether one loves contracts or not could be kind of the deciding factor.

in whether someone goes into corporate or litigation because I for one definitely loved contracts. That was my favorite class my first year of law school. And you know, of course, I ended up in corporate and you ended up in litigation. I always had great admiration for people who wanted to write contracts. I thought that was I thought that was tremendous. They only came to me when there were problems with them and we had to litigate them. Right.

Joyce Sophia Xu (09:12.818)
I mean, the goal for every good corporate lawyer is to write clear, well thought out contracts that would not lead to disputes. Okay. So you decided to go to law school and had an interest in litigation. And what was law school like for you? Was it what you had expected going in?

So I will say that until I got to law school, and I worked very, very hard during high school, during college, I studied extremely hard to do well, but until I got to law school, I had never worked as hard as I worked my 1L year of law school. Our class schedule began at eight in the morning and was five days a week, 8 a.m. I can remember going to class until whenever it ended, two or three p.m.

and then going directly to the library from the end of class and being there until 11 p.m. or midnight studying and working. And that was pretty much my daily routine all the way through from for one L year. So I think that it was a lot more work and challenging than I had ever encountered in anything prior to that. Now, I will say that was an asterisk because once I joined a big law firm, that was no longer.

the hardest that I had ever worked. But up until that time it was, I will say that I was pleasantly surprised at the people that I met and my classmates. Several of my law school classmates and section mates are still some of my very best friends, even to this day. And going into law school, you hear about the horror stories, like the paper chase, right, of people trying to undercut one another. I certainly didn't see that at all.

There was great camaraderie and just frankly, the tremendous intellect and intellectual curiosity among my peers. It was really, really wonderful. It was different than undergrad because obviously everyone there is interested in the law as opposed to undergrad where you have classmates who have very, very diverse interests and career paths. But I would say even among my law school classmates, there were still diverse interests within the law.

Joyce Sophia Xu (11:29.23)
And some of the things they had done, a number of my classmates had taken time off between college and law school. And it was just unbelievable to hear what they'd done in a year or two even between them. So I think that was certainly a pleasant but unexpected part of law school. Yeah, well, that's great because it's so important to have, especially during the first year of law school, when that kind of connection and support network is just incredibly valuable.

absolutely. Knowing you're all in it together, I think is really valuable. Yeah. So at that time, did you live in Cambridge? I did. I did. I lived in Harvard affiliated housing. They had a number of different grad student housing, but I actually lived very close to an ice cream store, which I made a rule that I could not go there by myself or I would have been there every day. Nice. Yeah, this is

making me miss Cambridge. I lived there for a little bit. There are definitely a lot of good ice cream places there. I don't know how that came about, but I remember going to quite a few when I was living there. There's a market with the college campus for sure. So it sounds like you really loved law school. Lots of interesting people around you and great friendships being formed.

So I'm sure you've got tons of great memories from these years. What are some of your most favorite ones? That's a tough question because you're right, there are so many good ones. It's really difficult to select just one or two. But I think one of my favorite anecdotes from law school, which dovetails with my musical interests, I was in the law school a cappella group. We were called the Scales of Justice, very aptly named.

I think they're still around actually. I think they're still going strong if I'm not mistaken. But I sang all the way growing up and that was something I really wanted to continue in law school. And our acapella group had a tradition of singing at the beginning of each semester for each incoming 1L contracts class. We had a song called A Stopple, which was written.

Joyce Sophia Xu (13:53.754)
of course, by law students at the time, and it was a parody on contracts law. And the professors were very wonderful about letting us sing, you know, for three minutes at the beginning of each class. But at the time, one of the contracts professors who I did not have, but some of my good friends did in subsequent years was Elizabeth Warren. And Elizabeth Warren, historically had not

permitted the Scales of Justice to sing in her contracts classes. She very much valued every second of her time. We respected that, but for some reason, finally, my 2L year, I think it was, she decided that she wanted us to sing. And I will never forget when we walked into the classroom, and we went before her class, so we did not infringe on any of the class time. We wanted to make sure we did not waste any of her...

of her minutes, but I had the solo on Estoppel and I remember singing it in front of her class and she was so excited that she asked for an encore, which we were not prepared to sing, but since Elizabeth Warren asked, you know, we definitely did it and pulled one of our other songs out of the hat that was called Don't Call on Me. And from that point forward, I ran into her a couple more times on campus and she would always smile and wave and say hello.

It was just a fascinating experience. That was my sort of one encounter with Elizabeth Warren, but it was through singing. Wow. You all must have been so psyched and so proud. That's amazing. Wonderful. Can we get a link to you singing these songs?

gosh, I don't even know if we have recordings of those. I have recordings of other songs I've done, but I don't think that... Remember, these were the days before smartphones and things for the most part, so I don't think for better or worse videos of those exist, but that was certainly a great memory. And then I think the others are just, again, the sort of casual times that you had with section mates and classmates getting to...

Joyce Sophia Xu (16:00.552)
meet in Widener Library and have study sessions and then afterwards just really getting to know all of my great classmates pretty broadly. So great memories. Wonderful. And when you look back on these years, were there classes or projects that you worked on that really helped shape you and help you become a better lawyer?

Sure, I think that the times actually really helped shape that experience. So I was in law school from 2007 to 2010, which was right in the midst of the US financial crisis. So my 1L year was relatively normal and straightforward. And shortly after that is when all of the big banks went down and the world was, especially the US was in a financial crisis. And I think that

That certainly shaped my approach because I knew how important it was to be dedicated and focused and do well in law school because so many law firms and other employers simply stopped hiring and in fact were terminating people at a time when my class was trying to get jobs. it was a time where going to Harvard, you had great job opportunities. And even for people

schools like Harvard, it was very challenging because the jobs just weren't there as they had been. So I think that there was a seriousness to my class and certainly the class after mine that I think, and focus on really trying to get to the next phase that I think had not been there historically, just because again, there were so many fewer jobs to be had.

So that certainly influenced a lot of my approach. And I was very grateful to get a summer position for people who don't know. Typically for big law firms, the way it works is they give you an offer as a summer associate for your 2L summer. And then if all goes well, you get a job offer for a permanent position at the end of that summer. And both of those things were extremely rare or at least rarer than they had been.

Joyce Sophia Xu (18:22.288)
A lot of the big law firms either didn't have summer associate programs or capped them or they were already full. By the time the employers got to Harvard, we historically had been at the end of the interview cycle for on-campus interviewing and a lot of the big law firms stopped hiring. And those that did hire summer associates, many of them hired permanently only a handful of their summers, if any. And it was simply, it wasn't a reflection.

of the performance of the summer associates, it was that the firms did not have the bandwidth to hire. So I was very grateful to get a summer associate position and then a job offer because the times were so uncertain. We didn't know what the economy was going to be doing and how long it would last and what the job market would look like in a year or two from the time of graduation. Yeah, exactly.

I was by that time, I had already been with big law firms for a while and I was with Simpson at that point. And I really saw the other side of what was happening, and definitely a lot of fear, like you said, a lot of uncertainty. And the firms were also completely in the dark as to how long this financial crisis was going to last.

when the activity levels were going to pick back up. everyone was just scrambling to adjust their hiring budgets. I remember a lot of firms, like you said, reduced their summer programs and also even rescinded or postponed a lot of the offers that had already been given out.

So how did all of that impact your choices on what classes to take? Did you think about, okay, I need to take this class instead of the others so that I could better position myself in the job market? I tried to take classes that I thought would be important in terms of practicing law. So a lot of the courses that

Joyce Sophia Xu (20:41.125)
I, and again, this is not having ever worked at a law firm before. So I think in retrospect, knowing what I know now had I known then, I may have selected differently, but I took courses that sort of seemed to me to be the.

core courses, things like bankruptcy. a second, I think I took a second administrative law class because there was a lot of that. had a pretty good sense that I wanted to be in the DC area. So I thought, well, administrative law would be a good one to take. So I really tried to focus on what I thought would be core courses. I think I took a tax course that would make me marketable as a junior associate.

What I subsequently learned is so much of being a lawyer, learn on the job and the knowledge that you gain. There's not really a great way to prepare to be a lawyer other than hitting the ground running and learning as you go and actually doing it. So then right after law school, you started at Binnum McCutcheon? Yes.

And that was your first job out of law school? That was my first job, yes. And how did you like that experience? So it was super exciting for me because again, coming from way out west, know, small town girl, for the first time, I had a full time job in a big city, in a big metropolitan area. I finished school and it was just so exciting to be in that environment.

And one of the first cases that I worked on, which is a public case so I can mention it, was the Gulf oil spill when the Deepwater Horizon Mobile Offshore Drilling Unit, if I remember the acronym correctly, had the big oil explosion in the Gulf in 2010. And it was just so exciting to be working on something that had made news headlines. It was all over the news. I'd read about it when it happened at the end of my

Joyce Sophia Xu (22:50.031)
third year of law school and had never in my wildest dreams did I imagine that I would be doing work on that matter. And it was really, really exciting. Years later when the movie came out about it, I thought they really should have extended it past the actual incident and shown all of the legal stuff that came afterwards. shockingly, must not have had a great appeal for non-lawyers in Hollywood. I'm thinking back to what you had said before the very beginning.

about switching from wanting to be in journalism to wanting to go to law school. And your thought was that you'd rather be making the news than reporting the news. And it sounds like you got your wish right out of law school. It's true. It was really...

It was really fascinating to be working on a case that was in the headlines. I think just in terms of numbers, I think that's probably, that certainly is the largest case I've ever worked on, just the numbers of people and parties involved. And to be able to do that sort of right out of the box was really exciting. It was really exciting. And that's not to say I have lost my desire to go into journalism entirely. I still love journalism. So it's not to say

Never say never, maybe legal journalism someday. Right, exactly. I could definitely see that. Tell me a little bit more about how the firm was organized. Did you have any kind of rotation system or did you just go straight into litigation? I just went straight into litigation. So the structure of Bingham at the time, and that goes back to what I mentioned earlier about the bifurcation, was very much there was the corporate group and there was the litigation group.

And that's how, and certainly within those that were much many, many other groups, but broadly speaking, as a first year associate, you went into one or the other. So I was just in litigation. And again, my, the biggest chunk of my time that full year, first year was, was the Gulf oil spill case. And then I kind of organically transitioned into more of the white collar team there when the deep water horizon matter wrapped up.

Joyce Sophia Xu (25:07.076)
The white collar group was very busy, as you can imagine. By that point, there was a lot of fallout from the financial crisis, lots of litigation happening in relation to that. And our white collar team was extremely busy. And I got picked up by that team and that was also life-changing. I worked with three tremendous partners. I think Joyce, you met at least one of them, Mike, and...

of course. Yes. That was when I first met Mike and two other partners on his team. And I really fell in love with the work that they were doing. It was really exciting. They did more government investigations and government litigation as opposed to private civil litigation. And I really liked that aspect of it and the securities laws, commodities laws. And that was my sort of happenstance introduction into

white collar, is ultimately what I ended up doing for the bulk of my career in private practice.

Joyce Sophia Xu (26:18.062)
Thanks so much for listening. Did you enjoy listening to Darren's favorite memories about law school? Do you have a few of your own to share? If so, please do drop us a line in the comment section or send us a text. And please do tune in on Wednesday for part two of my conversation with Darren, where she shares more about her approach to work, growth, and mentorship. Darren will also tell us what it was like for her changing jobs during the pandemic.

Until then, be well and be happy.