Intro Music

Tyler Finn    

How do you chart a path to general counsel before the age of 35 while staying open to reinvention, learning to navigate different company cultures and managing through massive industry shifts. Today, on the abstract, I am joined by my friend Andrew Epstein, General Counsel of DemandBase, where he leads the company's legal trust governance and ops teams. His career has spanned big law, some big transactions and multiple in-house roles, all grounded in a sort of mindset of curiosity, intention and ownership. We're going to talk today a little bit about some of the career bets that he made early on, how we built credibility quickly, and what it means to lead legal today in a really fast and changing market. Andrew, welcome to this episode of the Abstract.

Andrew Epstein  

Thank you for having me. Tyler, I'm pumped. I've been been listening for a while, so I'm glad to be on.

Tyler Finn  

Yeah. I mean, I know you've got a lot of friends who've been on. Andrew Woods is a great episode as well. We're gonna beat him today though. We'll get more listens, I think.

Andrew Epstein 

That was as Andrew Woods and I have a running competition on another podcast, so he's beating me on that one. So I'm coming for him on the abstract.

Tyler Finn 

Well, I mean, I mean, I can put a little bit of ad spend behind it. yeah, jokes aside. You know, I don't actually start every episode with with folks journeys through law school, but you were really intentional about where you went to law school and the sort of approach that you took then some other decisions while you were there. I think it's useful. I think there are actually some folks who are listening or thinking about if they should, should go into law and trying to make some decisions like that. How did you approach the decision to go to law school, and how do you think that that choice influenced your sort of early trajectory?

Andrew Epstein 

Yeah. I mean, I think when I was at undergrad at Berkeley, I kind of knew pretty early on that I wanted to go to law school. The question was, you know, what would that journey look like for me? And I think I took, I ended up graduating Berkeley a semester early, and so in three and a half years for for personal reasons. Actually, my mom, at the time, had gotten really sick. I grew up in LA, and I went on to take care of my mom, and so I had taken a year and a half kind of between school. I went and worked for a nonprofit, the Avon Walk for breast cancer, actually, where my job was to, like, be a walker coordinator. I was literally signing people up for the San Francisco Walk, helping them on their journey, helping them fundraise, doing a bunch of cold calls, and so that has helped me in my career, like the, you know, working kind of like Avon Walk. I worked at Nordstrom, kind of these, like service industry jobs, but I knew that I wanted to eventually go to law school. And when I was doing that, I knew that I wanted to be on the East Coast for the first part of my career, specifically in New York. And so I was pretty intentional about going to the best law school on the East Coast, which at the time that what I got into was GW. And so I made the decision to go there. I know it's not New York, but I knew that it was that it was a good feeder into the work New York firms and firms and another type of work in New York. And I knew there would be, like unique opportunities there in DC as a law student. So that's kind of what led me on, that on that path,

Tyler Finn 

You did actually take advantage of sort of unique opportunities in DC. I think most folks after their first year, second year, you know, thinking about government, sort of internships, big law, you went inhouse with the Washington Nationals for the summer. That's pretty cool. Tell us about how you got that opportunity, and how it ended up sort of shaping your journey then later in law school?

Andrew Epstein 

yeah. I mean, I think, and that's part of, you know, I think what you and I will talk about in a little bit is kind of taking a risk and taking a non-traditional path. And it's very traditional as a first-year law student to, you know, a couple months in, there's a on campus kind of recruiting thing where you go and mostly go and clerk for a judge, and there's no no knock for people to go and clerk for judging. Like, that's amazing. I knew I didn't want to do that. And so the question was, like, what would I do if you don't sign up for something like that? You kind of have to apply to a bunch of things over time, and you're coming towards your end of your one Oh, year, it's pivotal that you get an internship. And I didn't have anything until weeks before finals, honestly, and my friends had gotten and I knew I was holding out because I had heard of this job kind of like towards the back half of the semester, and I got an opportunity to interview with the GC, this guy, awesome guy named Damon Jones, at the time of the Washington Nationals, and I knew it was going to be really competitive. I went in to the interview, and I just talked about why I wanted to be in the office of a GC in a GCS office. Obviously, being in a baseball team is amazing, but I think a lot of folks before me, and I know this because David told me this, went in and talked about how much they love baseball and like, this guy's batting average and their favorite player, it's like, you're not interviewing to be a scout, like you're interviewing to be a lawyer, right? So, I talked about how I thought in this three-person legal team that I had an opportunity for a lot of impact and to see a lot of unique things that obviously resonated with him. And I got that job, and I was full time, my one all summer, and then my two all year. I basically took a lighter course load and worked Mondays and Fridays at office, which was super cool because the office was at the stadium and so specifically, like for day games, you would go out and watch the last three innings, you know, on the clock, which is a good thing to do.

Tyler Finn  

That's awesome. Do you feel like that experience helped you stand out at all then when you went to interview for sort of, like, big law opportunities, I mean, I imagine there can't be that many folks walking in the door with Office of the GC at a at a baseball team on their resume.

Andrew Epstein  

Yeah, certainly, I think, I absolutely think it did. I did well in school. I was not the best student coming out of GW, but I think I did well enough to get a few interviews at on campus recruiting at the time. And I do think part of that was I had this different thing on my resume that I could talk about. And again, it was like, how do you talk about that? Yes, that got you into the door, but I didn't just like, maybe I talked about baseball for 30 seconds of it or something, but then I actually talked about what I learned and what I did, and it gave me this opportunity to go and get my first, my two summer associate job, which is the job that ended up taking after school at Melbourne Myers, I think in some ways, because my interview stood out, you know, for my background and kind of like, how I the type of work that I had managed, you know, pretty early on in my legal career.

Tyler Finn  

I think you were also pretty intentional about picking a firm like O Melvin, or you had different criteria than maybe other folks. Was it just someone like, How can I pick the firm that has the top starting salary. Tell us about why you chose O’Melveny in New York.

Andrew Epstein  

Yeah, again. So I knew I wanted to be in New York. I knew I grew up in LA I went to undergrad in the bay. I knew I was most likely to head back to California at some point, but I wanted to start my career in New York for a number of reasons. One, I think I was I learned pretty early on in law school that I did not want to be a litigator, and I think that law school really trains you to be a litigator. There's not a lot of classes that you can take or opportunities that you get where you're more of a corporate or a transactional attorney. That certainly was more of the corporate transactional side. Obviously, you can take contracts and some VC classes, and you know, there's, there's, there are business law, there are opportunities like that. But I knew I wanted to start in New York. I knew that I wanted to work for a firm that had offices all over the country, particularly that was LA or West Coast based, which on Melbourne is, and that would give me the chance to work with partners in the LA office and the SF office and the London office and the New York office, so that I can diversify my practice, but also have my hooks into California, kind of when I knew that there was going to be the high likelihood that I'd want to return.

Tyler Finn

What did you end up focusing on in your event a practice around privacy or data? But yeah, what was it like in the early days and there. And how did you sort of diversify the different practice areas you were working on as well?

Andrew Epstein 

Yeah, I actually didn't really start the privacy work until I moved in house that it was at the tail end of Melbourne. I did, but privacy wasn't really a thing, and then, I mean, it was just starting to become a practice in these law firms, and I worked on the privacy front. In the last maybe a year before I left, I worked for this honestly, genius partner who, I think she has since left. She was the GC of a healthcare company for a while. I don't know where she is now. I haven't even probably told her, like how how she was to me at the firm, but she was just so smart, and I loved working on the few projects that she had for me. She came on to help build the privacy practice in 2016 but before that, I was working mostly for the Capital Markets Group and some M and A work. And again, that was somewhat intentional, right? You had 16 people in our summer associate class. And melbony was known, and is known as a litigation powerhouse. They were building out the transactional group and the Capital Markets Group in New York. Specifically, they had coached this kind of rainmakers type partner from Sherman and Sterling, and he was building out the group. And I pitched kind of my wagon to my his name was Mike, to Mike and his team, and I wanted to become in that summer, and then I want to become Mike's guy during that summer and and because he got, kind of like the selection of summer associates. And when I joined Melvin, I was working on his deals. But it also with the nature of transactional practice, capital markets practice, we did a lot of bank side work, some issue or side work. IPOs follow on, secondaries, things like that. But there is, there are these ebbs and flows because you're you're either on a deal or multiple deals, or you're not. And so I knew it would give me the opportunity to say, hey, you know, Hey, Mike, can I go work for so and so partner in the SF office on one of his deals or her deals? Can I work on so and so partner in the LA office? And that, it was great. Sometimes it ended up biting me in the ass, frankly, because, like, I would be on an LA deal, a New York deal and a London deal at the same time, and during that period is challenging, but it also allowed me, you know, to go home LA, to see friends and be in An office, the same with my girlfriend at the time, wife now is from the bay, and so I'd be able to go to San Francisco and kind of do that work. But I kind of centered it around like, what are these smaller practices where I could have an impact and not just be just another person or another kind of cog at the firm, a large firm, and so when I proved myself to Mike and to David, who was another partner there, who's who I'm very much as a mentor and a friend, they allowed me to run deals much earlier on than I think I would have gotten at some of these more traditional transactional powerhouse firms where there's more of a wait your turn type of approach.

Tyler Finn  

What was it that motivated you to want to go in house then, besides the fact that in retrospect, in hindsight, you got to work with Vanessa Wu podcast guest Tuesday, and I'm sure that was an incredible experience. We can talk about that. But what was it that made you think, okay, I want to go in in house and try that side of practicing law?

Andrew Epstein  

Yeah, I knew as much as I liked the work in capital markets. Group capital markets certainly, like during that time, is very much precedent based like, what are other people in the space doing? What other risk factors are companies listening out in this space? Do your research. You know, there's, there's very kind of set rules. I I've always liked to like color outside the lines a little bit. I think it was hard for me to build my practice out of something that was so rigid, and so I kind of knew I wanted to be more creative. I wanted to have this opportunity to impact a business beyond just legal and sort of kind of set, set your own kind of rules. And that's why I started the privacy work with one of the partners there, because it was 2016 - 17. GDPR wasn't even out yet, and this concept of privacy as a company was pretty new at that time. I had been going back and forth to California a bunch, and I knew I wanted to move back to the to the bay, either LA or the bay at the time, and I had asked a Melbourne to transfer me to San Francisco, and they were just the transfer was taking time. At the same time, I was applying to in house roles from New York. I almost worked for another podcast, Adam Greenberg at Warby Parker, super. Love that guy, but that's

Tyler Finn  

a good yeah. That's a good episode, too,

‍

Andrew Epstein 

Yeah, but I interviewed with Vanessa at LiveRamp, be the second attorney under her at LiveRamp. LiveRamp, at the time, was a subsidiary of a public company called axiom, which is a 4050, year old Arkansas based data broker. They had acquired LiveRamp, which is very much the startup tech company based out of San Francisco, run by really smart guy, Travis May at the time, and who had hired Vanessa to be the GC of LiveRamp. And so this was an opportunity to work for her. And so the timing worked as such that, like, I had gotten the offer at live ramp the same day, honestly, or almost the same day as I recalled that my transfer had finally gone through at O Melbourne, and so I had been asking that month, you know, weeks over, where's this transfer going? What's going on with the transfer? How come this isn't going through? Yet another like, Oh, finally we figure it out. I'm like, Oh, just kidding, I actually am leaving. Started this data company and in San Francisco. And I think a couple of the partners, the one who I work for, like, totally got it. He wished, yes, I still keep in touch with them. A couple other partners were like, What are you doing? Like, this is a huge mistake that you're making.

Tyler Finn 

Really interesting.

Andrew Epstein  

yeah. And I said, I appreciate, enjoyed working for you. I want to take a risk here, and I'm, I think it's gonna work. And so, yeah, Francisco and we're got the opportunity for work for Vanessa at this high growth subsidiary of a public company where they really, kind of like, left us alone for for a while.

Tyler Finn  

I know that you ended up working on, and she and I, we danced around this a little bit on RSM, because we mostly focused on, sort of her experience at rippling and some of the acquisitions that LiveRamp had done. But you got to work on some pretty complex transactions while you were there, right? I mean, there's a sort of like delisting from NASDAQ that happens a spin out from axiom. Can you walk us through a little bit about, like, what those deals looked like, and did you feel totally comfortable doing that with the sort of capital markets background, or is it very different in house? Yeah, like, what's the adjustment like to in house life?

Andrew Epstein  

Yeah, I think there's like, Well, I remember the time I'd done a few more, like tuck in M A transactions where we had done smaller, meaning, like up to 150 million acquisitions or more of an Acqui hire type motion, and that I did feel more comfortable with. We worked with a really smart chief strategy officer there, and I did take the reins again, I kind of mostly from Vanessa on that one, where I would work on those, you know, due diligence interviews, kind of the founders and work with the deal team on that. Work with post transition integration was also a huge thing. I think only companies think about acquisition, but not about like the Deal Memo or the deal philosophy and what you're going to do after this deal is closed, and how you were going to integrate this totally different company, including systems, customers, contracts, all these things, and so that I kind of like had a baseline understanding of the transaction where LiveRamp sold axiom, the parent company, I don't think Anyone could have had the like background for that one. It was such a unique deal, in the sense that what ended up is like we were selling our parent but we were sitting under, like my boss's boss, Vanessa boss was that was the work for axiom. So, like, at one point you're negotiating, it's gonna stay at LiveRamp? What's going to go to axiom? And I'm negotiating against my boss's boss, who ultimately had the ability to, I guess, fire me. So, like, that structure doesn't work because I'm like, I'm like, pushing hard for LiveRamp against this person who is in my org. It was just very odd, and I think that

Tyler Finn  

that's so interesting.

Andrew Epstein  

And I think that at one point we, like, had this other lawyer come from axiom to live room to help the LiveRamp side, and he we were on a call together, and we would be advocating for LiveRamp, and he would be saying, like, no, like, on the on the call with others like Andrew has no idea was talking about this. And I, like you, what he's talking about. And then he would mute and be like, you're totally right. I totally agree with you, but I gotta, I gotta take the other side. But we ended up basically selling, selling our parent and a lot of what was really interesting about the deal was, how do we build the systems and infrastructure at LiveRamp in a really short period of time, like this deal was closing in October, and that's Vanessa was out in the beginning of it, and then, and then back to help close the deal. And she, she was instrumental. We worked a ton together during that time to to close the deal in October of 2018 we got the opportunity to go to the New York Stock Exchange because we had delisted from NASDAQ, we had listed on nicey, and be there for the bell ringing, which was so cool. And so that's like the glamor of it. But the behind the scenes of it is like we had no contract management system at LiveRamp because we relied on our parent. There was contracts that were coming over that were 10 years old, that were in PDF, that were not readable. We had which customers went, where actually ended up being one of our biggest customers at the time, because of how the deal works. So a lot of what I was doing was this, like inter company agreement work, what's going to stay, what's going to leave. How are we going to sign up our own contract management system and be able to run as an Independent Business come October 2018 when we signed the close, and then it was like team building, because we had to bring over, we had to figure out some folks from axiom side, on the legal side, were gonna go to IPG, which is where we sold axiom to, and some folks were gonna come to LiveRamp to work for us. And so just like the team dynamic, how we separated that out, and how we became an independent business during that time, was super unique, really interesting transaction, and something I feel like, very thankful to be a part of.

Tyler Finn  

Where was it in this journey? Also, I guess that you started to pick up privacy expertise, or that you felt like this is a place that I should I should really lean in, because I know that ends up becoming huge part of what you do at demand base as well. Curious to hear about that.

Andrew Epstein  

Yeah. I mean, I think truly, like at the outset of joining LiveRamp, that was just so core to the business, like I had joined 2016 I thing and 2017 and that was right before GDPR. We needed to make very material changes to the business through GDPR, through CCPA, just based on what LiveRamp does. And the privacy team was run separately, and so it didn't roll up to Vanessa at the time. And I think that I've taken some learnings from that and building my own team at DemandBase from a structure standpoint, but we worked quite a bit with the privacy team, just given the nature of the business. So I feel like I don't, I did not, and I do not hold myself out to be a privacy expert, but I think you really have to understand privacy in the ad tech space, and currently in the in the go to market, or the martech space, just given the type of work that we do. So you always have to be kind of like, have enough knowledge to be dangerous, but I think you also have to understand, where are your Where do you need to help someone to come in and help you, kind of like, bolster that knowledge so that you who's gonna, who's gonna compliment you, so that you know that you have built out the right team and the right foundation for the work that you're doing.

Tyler Finn  

One of the other areas. And you can help me a little bit on the timeline if I don't get it perfectly right. That I thought was interesting was, you know, Vanessa eventually leaves live ramp, so for a period of time you're reporting into the axiom GC. I mean, I'm curious, like, you know, how does that change the team dynamic? I know Vanessa has a particular leadership style. It's one that I really admire. I'm curious, you know, how do you how do you manage having a different GC as your boss? It's not something that happens, I guess, to folks all that often. Maybe because once you're in the GCC, folks tend to stick around for at least a little while.

Andrew Epstein  

Yeah. So So started, I think not that much. Long after the transaction, Vanessa left to go join rippling and obviously see what she's doing there. But I was working for what was the axiom GC. Now the live RAM GC, the library parent, hold code, GC, axiom. Axiom was an IPG company and he was, you know, a Arkansas based, truly like powerhouse, Arkansas attorney, you know, knew him. He's, you know, good friends with Bill Clinton type of guy and he had that type of, like Southern drawl, the way talk that people wanted to listen and just, I think you can pick up things from different leaders that you want to take on and emulate. They're things that you learn that you want to do differently. And so I think I always tell folks like when they when they're moving on, or when you know if your boss leaves and someone else is coming in, it's an opportunity to learn a totally new set of skills from a new leader, and also learn like what you may want to do differently if you are given the opportunity to lead right, and so you learn structure, for example. Like when I went over to demand base, I knew that I wanted the privacy team to be working more closely with, like the commercial legal team that we had than we had been doing previously at LiveRamp, and that was something that I was really intentional about. But it's really just kind of like understanding, okay, this is a very different business that had purchased us. This was a very different or that the executives had come over from axiom are not much more involved, and their styles were going to be much different. And so how do you navigate that? And still, you know, get budget and hire and build out a team and get technology like some of the technology asks were, were challenging. The beginning, I really had to show why we needed a specific tool and how important it was, or why we needed a new head, like we had done a bunch of work on a ticketing system, for example, on how quickly we pick up agreements, what our response time is, what our turn time is, how many turns it takes to close a deal. We had built all that out, and I use that to be able to say, like, hey, we used to be able to pick things up in X amount of days or hours, and now it takes Y amount of days or hours because our business is growing that's impacting cost time to close. And so I'm another one on my team to be able to get back to what I believe is the right ratio of time to close. And so those are some of the ways that you're able to kind of convince someone who may not be as used to that type of thinking initially on how to get something that you're really driving for.

Tyler Finn  

When did the opportunity to lead legal at Demandbase come around for you, and how did that ultimately, you were able to convince me to hire you and jump into jump into the GCU role.

Andrew Epstein  

Yeah, I joined Demandbase in September of 2021 and so at that time, I had spent about four and a half years at LiveRamp, two and a half of which as the subsidiary, and two of which as the public, standalone company. And I think you know, the opportunity came about honestly because someone who I had supported as a commercial attorney at LiveRamp went on to be at the time. She's no longer here now, but the CRO at the time of demand base, and I think that she said, Look, I'm like, here's this attorney that I worked with a bunch and we navigated partnership deals. We had, we had entered into the TV space during that time, and she led some of that. And these were not going back to what I said way earlier around, kind of like following very specific rules. This was the Wild West, so we had to be really creative on what we were thinking. And so I think if you can establish yourself as a business first, creative attorney who's looking to help the business get the deal done or the job done, then that will pay dividends later on. This was years later where, you know, demand, this was looking for a GC, and I know she put a good word in for me, because she said, Look, this is someone that I worked with before, and I think that he would be good.

Tyler Finn  

That's great. Yeah, I think, you know, of course, there's times where you have to hold a line with sales or product or others, but having, like, a really friendly relationship with those cross functional stakeholders. I mean, it's not only good for the day to day, but it's also maybe for your long term, right? Some of these folks go on to become CEOs or found their own companies, or, yeah, I'm curious. When you joined the team was pretty small. You inherited a couple of attorneys compliance. How did you evaluate what you thought the company was going to need as it as it scaled? And, yeah, let's we started the conversation there, and then maybe talk a little bit more about scaling the org.

Andrew Epstein  

Yeah, I think I was a couple of things. One is I was really transparent in the interview process around my vision on what the team would need. And I think part of it is timing. I was fortunate to be joining in September of 2021 like, as you know, in September of 2021 early 2022 there was, like, a million IPOs going on everything was like, the market was really firing, and I should have demand based. Was like, we need to become public ready. We want to fit the profile one of these types of companies. And so I was able to come in and say, Okay, you're like, 650 people or something at the time, how many people do you have on legal? Two, one person in compliance? Well, that's not a public company. That's not what a public company looks like. And so if you want me to come in and lead this team, I need to have some leeway and some budget and some bandwidth to hire the team that we would need to have in place to be the company that we want to be and so I was really honest around here's the things that I think I'm good at, and here's areas where I would need help. And so privacy is one of them. I said, Look, I worked at a company that privacy was core to the business. So I know, I know what it takes. I know how important privacy is going to be to this company. And at the time, right before I joined demand base, had made acquisitions, one one of Bucha with of a data company. And so privacy was even more important for our business now going forward. And so I said, we cannot be this profile of a company without a true privacy leader. So that's going to be my first hire. I also said I am a really big believer in legal operations, because I've seen tangibly how much it impacts the business. Without legal ops, I would not have been able to make the argument around headcount and ticketing and now AI, but that wasn't even really a thing then, that that it's just core to this accepting, knowledge management, training, all that stuff starts with legal ops. There's way more than legal ops does. And so those were two things that I said at the outset, that we need privacy. The team got it. They understood legal ops. I had to convince them. And once they understood the pitch, they got it. Once you brought in a legal ops person, they really got it. But then I was also able to, kind of like right size the org, to say you can't have a compliance team of one. We need to have more folks than that. And so I was able to build up and make these hires in a fairly short period of time to right size the team for where we wanted to be as a company. So yeah,

Tyler Finn  

I guess, along with that, sort of like scaling of the team, I guess there's almost like a little bit of self that maybe you have as well as you're stepping into what is like your first full GC role, how did you think about that and trying to be sort of self aware and think about how you might need to grow as as a leader in a in a new leadership role.

Andrew Epstein  

Yeah, I think there's two things that I think about there. One is that you have, again, to be honest with yourself around areas where you don't have as much experience and where you need to grow that experience, then you have to say, Who can help me do that. And so I think a lot about in my career, this concept of like peer group or mentorship, and like mentors are not always like, Hey, will you know, I think that, like I said, even back at the term, there was folks who I really learned from who I felt like I want to get as much work or attach myself to this person as much as possible, because I want to sponge up, soak up what they're what they're telling me. And so things like employment we had an employment attorney at LiveRamp. I never dealt with employee issues before. Now I run that here at DemandBase. It's something that I think is challenging and interesting. But I asked a peer group, I joined a peer group, and I joined dinners and conferences and things like that where I could meet people. And my mindset was like, go to these things and meet one more new person, right, who you can build a relationship with. And it's not a transactional relationship. It's not what can you do? For me, it's like a true relationship. And then once you have that core group, you're able to say, like, has anyone ever seen this before? I don't know what I'm doing here, like, you have to be honest, I don't I haven't seen this. I don't know what to do. Have you seen it? Can you help me through it? And that's a lot of my kind of like, go to initially, before I reach out to outside counsel or someone who I'm having to pay for. It's building up this strong network, like, like you said, many of a few of whom have been on this podcast or other podcasts, right? It's like these are folks who are super smart, have been have unique experiences themselves, and you stay in touch with them, and you say, Hey, this is an issue that I'm dealing with. Have you seen this report? And maybe they say no, but I have a buddy of this other, you know, two guys. Let me go ping her or ping him, and that's a that's a new relationship.

Tyler Finn  

You kind of create your own community over time. Yeah, you mentioned, you know, joining in 20 the market being in place, right, obviously, and we'll see what happens. I don't think anybody knows what happens, even with the market, when this episode gets released, what it'll look like, but the market around, like taking companies public, what investors expectations are, etc, have all really shifted since that point in time, what did that mean for your work, your ability to keep sort of growing the legal org? How did you have to recalibrate maybe some of your own expectations?

Andrew Epstein  

Yeah, it's a good question. I think I was fortunate. I think that not that I could have planned for what was happening in 22 or 23 and certainly not that anyone can plan for what's happening today at all. I haven't even looked at the market today, but

Tyler Finn  

don't it doesn't,

Andrew Epstein  

Yeah, it's doesn’t going to help or hurt either way. But I think that there are things that you can do to be a little bit intentional about how you structure a team that could help you withstand a lot of things that may or may not occur right and so, for example, on the commercial side, there's two things that we do here at DemandBase. One is that a strong kind of VP of commercial legal, lawyer who leads that function, underneath him is a contracts manager. It's not a lawyer. I'm a believer in that. I've been a believer in that. I led a team of contracts managers for some time at LiveRamp. You don't need to be a lawyer to be doing that work. Another thing is like, okay, that team is small. What can you take off that team's plate, right? And so we do. We negotiate all of our NDAs through our clms ai function. And so I've said this on kind of other talks before. But part of doing that is you, you as the GC, or me as the GC, has to say, the way we structured it is basically like, there's a few things that we look out for in these NDAs, and they're there. It will get kicked to a lawyer. If it's picked up by the AI, will get kicked to lawyer. If not, it gets auto signed, basically. And so that requires me, as a GC, to say, I think I'm comfortable with whatever that risk may be, that some things may slip through the cracks, and we don't have a quote, unquote human loop there. And what is the true risk? What's the practical risk? I think that is outweighed by the fact that we don't have lawyers or contract managers dealing with that work, and we have them dealing with the things that are more are more important. And those things that are more important are actual client, customer work, but also like what the next thing we're going to train our AI tool to do is it order forms, essays, whatever it may be. And other than I do is I stretch folks in a way where there's someone on my team who's super smart, and he does some privacy work and some GRC work, he has a background and an interest in both, and straddles both of those teams. That has been really successful. I will say it isn't always successful. I had someone doing some legal ops work and some commercial work, contract manager work. What ended up happening there was this person who is great, has lasted a year. She left her company because she said, like, I'm really passionate about these legal ops projects. But what ends up happening is, I get down the road with them, and then I have to stop everything that I'm doing, because I have to start towards the end of the quarter, yeah, dealing with all the commercial stuff, and it's too hard for me to balance that. And I'm, like, I kind of thought that might have been the case going in. I wanted to try it. I get it. It, in fact, didn't work. And now, like, I'm gonna re split those roles again. So you kind of have to, like, test out these things and what works and what doesn't. But the theme is you keep the team fairly lean, to give folks both an opportunity to grow, but also to hopefully keep your cost down, so that when you are in these environments where you have to cut, you can insulate your team.

Tyler Finn  

So that's great advice. Yeah, maybe a last sort of substantive question for you on your time at Demandbase before we get to some fun ones, some closing questions. And I ask this also because, you know, you came to our spot dress summit and spoke on one of the panels, how you're thinking about, sort of the evolution of your team and the evolution of your function as AI becomes more and more what you're doing. I know that you're a very forward thinker on that, as you like, with contracts managers, as opposed to needing to have an army of commercial lawyers in house.

Andrew Epstein  

Yeah, I think that, I don't know, I hope that I'm a forward thinker on that. I think it's so hard to keep up with everything. And I think that I get, I, like probably a lot of other folks in my seat or similar seats, get pitched on a new AI redlining tool tool or AI sure intake tool, or whatever, weekly, daily, and whatever it might be. And so I think part of it is trying to block out the noise a little bit like you do. I heard someone say, I can't remember where it was. I heard another GC say that she takes, I don't do this now, but I think I should it takes, like, I think a week on a new vendor that's pitching her to just like, see a demo, so that she sees what's out there. Like, that's an interesting thing to do. What I try to do is, yeah, I think it's really smart. What I try to do is think about, maybe less around, kind of like, what new tools are out there. Although we do. We have tried a couple we brought something in house for intake, for example, that we're testing to show kind of like, what type of work does a legal was it does a GC or do outside of commercial? Because people think a lot about contract metrics, and it's like we do so much more than that. We're getting asked all these things, from compliance and privacy and risk. You know, where else can we show that work? So that's one space that I think is interesting, but, but a lot of it is, how do you give permission and challenge your team to use the tools that perhaps your company already has? So we have, like many companies, a chat GPT, enterprise license, And so that's key, because we don't train on the it doesn't train on the data we put in. We don't train on the customer data that we that may be part of that. But so how do you use it? Right? Like someone asked you to analyze an agreement because there's a dispute of that agreement, load the contract into chat, GPT and say, here and write a good prompt, go and take the prompting class, like I have now taken to Chili's GCA, I 101 and 201 prompting classes because I really key, awesome, like, that's going to be really key to the success of the function. How do you prompt appropriately? What are things that I got asked by an auditor to write a memo? Like, okay, here's all the things that I want to go into the memo. And I like, maybe I shouldn't say this, but like, it loaded into our enterprise license, and it gave me the first draft of the memo. Like, why? Because I don't want to spend my time writing a memo, and I don't like, and I think that, like, that's not necessary anymore, so it's less about like, what new shiny tool can you sign up for? But how do you convey to your team that you want the team to be using these tools? And there's ways to use these tools, and how are we going to delete it in through our OKR process, I check on in on the team, like, what have you done today? Or what have you done this week around AI, work that can be interesting, that you can tell others about. Wow. So it's just like building for curiosity and giving permission to explore different ways to it in which we can use the tools that we're doing. I don't know what's gonna I mean, I think in the in the long run there, I still get pitched, and I advise, actually, for a company that's doing like this, AI an AI redlining tool. And I think that if that space is really, really interesting, I don't I haven't seen something yet that really blows me away, where it says I don't need lawyers anymore, you know, or contract managers anymore at my company. And so it's funny, because I opened up a role for a contracts manager role, and one of these companies took my posting, anonymized it, put it on or pseudonymized it, as my privacy leader would say, put it on LinkedIn, and said, these companies are hiring for contract managers when you could just do you could use our tool to do the same thing, and it costs way less, like something like that. I'm like, making fun of like me and our posting, and I'm like, okay, like, I get that, like, creative, thank you for not using my company's name, but I just don't know for there.

Tyler Finn 

Yeah, I Well, I'm proud of what we're building. I'm proud of the tool that we have and what it does. It's very much been designed with the eagle professional. And I don't think that we have an expectation. I don't have an expectation that that's going to be changing anytime in the next 12 months, 18 months, broadly speaking, I think most, I think most sort of folks would agree also that you know lawyers who leverage AI, I love that you're asking your teams about how they're using this on like, almost a weekly basis. Or more lawyers and legal professionals who leverage AI are going to be massively advantaged in the job market. But it doesn't mean that all the jobs are going to go away either, right? So, yeah, all right, as we come up on on time, um, I've got some closing questions for you. The closing questions that I like to ask, yes. The first Andrew is, if you have a favorite part of your day to day,

Andrew Epstein  

yeah, um, I think that what I really like about my job, honestly, is that there isn't each day could be very different, and so maybe, like, the diversity of work is my favorite part of my day to day. That's kind of like a cop out answer, but

Tyler Finn  

you are a lawyer. It depends.

Andrew Epstein 

Like hardly back to firm days, I think that being in a position where one day you're working on a very strategic partnership, one day you're doing product work, one day you're dealing with an employee issue, one day you're dealing with, you know, fundraise like that, litigation, you know, like being able to have a day where your days or have a job or not, where your days aren't the same, is really interesting to me. I think that we've been doing a lot of work around what's also interesting is like the things that fall outside of the legal so I think that having the opportunity to be viewed as not just a legal leader, but as a leader at the company, is interesting. And so, you know, we're managing through culture shift and high-performance culture, and what does that mean, and how do you say your OKRs to that? And how do you inspire the next line of leaders at your company? That's not a lead problem, but it's a problem that needs to be addressed for our company to be successful. And so I really enjoy doing thinking about that type of work.

Tyler Finn  

Absolutely. Okay. I think this one's kind of a funny one, and I have no idea what your answer is going to be. Do you have a professional pet peeve?

Andrew Epstein  

Yeah,I have kind of, like a silly one, and I have more of a real one. I think, like the sillier one is. And folks, my team know this, I hate weather talk, and so you get on, like, a zoom, particularly, like, with people who don't work a lot together, and it's like, oh, man, looks beautiful out there. Yeah, it's 75 like, how about you? It's super cool here in Chicago. I hate, like, it just feels like, if we're gonna do the small talk with small talk, something else,

Tyler Finn 

I am guilty of that all the time,

Andrew Epstein 

but, but I think, like, I tend to go the flip side of that is when I get on calls, I get my Zoom personality, I think is a little bit different, like, I go straight to the point, and I've been given feedback that, like, sometimes you have a little bit of like, chit chat and small talk in the beginning, and whether talk is a good way to Fill that just, I think the thing that's more real is I, I take, I took a lot of pride, and I take a lot of pride as when someone asked me to do something, and I say, I got this, that I'm gonna do it. And so my professional pet peeve is when I'm asking that of others cross functionally on my team. Whatever is, like, I have faith that when you say, I got this, I'm going to handle it. You got it. And so it's great when I don't have to follow up. But if I follow up more than one time, like, that is actually, I'm like, oh, maybe you don't got it right. Like, like you said, got it like, I believe that you are going to do that, because that's something that I try to live by.

Tyler Finn  

Absolutely. Is there a book that you'd recommend for the audience?

Andrew Epstein  

Yeah, so I was, I saw that you asked that earlier. I was thinking about it. I There's a few. They're not great. I can't either not like tech necessarily. I have one sort of techie book, but two books that I really liked recently, one is that a lot of folks have read is ‘Anxious Generation’ by Jonathan Hayden. I have three little kids. I have a five and a half year old and I have two and a half year old twins, and so it's not as much about my children's generation. It's a lot about like Gen Z, but it's about how devices and the use of device. It's basically a juxtaposition of how we have vastly under regulated devices for our kids and over regulated the real world in the sense that, like, kids aren't just like walking around, going to town by themselves, or being they're being monitored and tracked. And I think he that he sets this in like a very like Malcolm Gladwell kind of Eden data driven way to show kind of those juxtapositions and what we could do about it. And I just find it really fascinating. And it's something that kind of like young parents of my generation, I think, are talking about, how are we going to do something differently for kids our age? That's one another one on a more personal level, is this book called Crying in H Mark.

Tyler Finn 

I haven't read it, but I've seen it in the bookstore, and I've seen it on friends’ bookshelves, and it gets all sorts of accolades.

Andrew Epstein 

Yeah, so the author is, I'll just make sure I know her name before. This is Michelle. I think it's Zauner. She happens to be also the lead singer of a band called Japanese Breakfast, which is an awesome band, really great band. I really love them, but she basically writes this book about losing her mom to cancer, and how she dealt with it, and how it kind of structured her childhood, her relationship with her family, how she thinks about her own about around time and her own passions. And yeah, it's a book that really resonated with me. I when I was in my early 20s, saying earlier I left school to take care of her. And so I think that like it, it's something that has definitely, obviously defined my life, but defined the way in which I think about time and how I want to spend my time. And so I it's a thread that has played out through my whole, certainly life, but career too, in a sense that, like even going back to that old me interview I was asked, like, something along the lines of, like, how important is this job for you? Like, and I think my answer was, like, look, this is a really important job and an opportunity, but I've been through a bunch of other stuff in my life that is actually important. So like, I want this, but if I don't get it, it's okay, type of thing. And so I think it just helps, it helps set your foundation, so that I think it's really great book, the last one on a more techie one is I just finished Elon Musk by Walter Isaacson. And I am not a like musk super fan or anything like that, but I do think that, I do think that his this concept of first principles, challenging everything to requirement, asking, like, why is this this way? And specifically, like, who made this this way? And it's not just that the legal department made it this way. It's Andrew when the legal department made it this way. Okay, go talk to Andrew. Why did you say this thing? I think is a really interesting way of thinking, and particularly around like the SpaceX and Tesla stuff, all of these things that he is challenging.

It's just like, really amazing to see how what has come from that. So those are three books that I think are worth reading.

Tyler Finn  

Those are great recommendations. All of you back for just more book recommendations together. Who knows if I'll even have to ask this question after the second book recommendation that you gave, but this is my traditional closing question for my guests, and I want to ask it to you too, Andrew, it's if you could look back on your days as a young lawyer, maybe just joining O’Melveny, something that you know now, that you wish that you'd known back then.

Andrew Epstein 

Yeah, I think it's getting out of comparison. I'll call it comparison culture. And I am still guilty, and I need I get something constantly having to work on, which is, you, you don't know where your career you can shape. You can shape your career in a lot of ways, like this is what I'm looking for. I want to be the small team i to be a small team. I want to do because I want a big impact. I want to do this and that. But I think that if you spend a lot of time looking around law school or the firm or whatever, and say, This person is more successful for me than me, or this person has got this, and I don't have this, it's a lot of noise, honestly. And so I think that if you can, like, acknowledge it as something maybe to drive you because you're but not spend a lot of your time thinking about, How do I look more like this person, or get this, or compare yourself to that, and just focus on, what are the things that you really want to get out of your career or work while still, like I said, like having people to be somewhat of like a North Star, I think that that is a healthier way to go about this career and frankly, life.

Tyler Finn  

That's a great sentiment to end on. Andrew, this has been a lot of fun. Thank you so much for joining me for this episode of the abstract.

Andrew Epstein  

Yeah, thank you. It's been it's been great. I really appreciate it.

Tyler Finn  

And to all of our listeners, thank you so much for tuning In, and we hope to see you next time.

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