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EP 03: From Punk Rock to General Counsel: Louis Shansky on Building Modern In-House Legal Teams
7 Plays11 days ago
In this episode of Beacon Voices, Akshay Verma sits down with Louis Shansky, General Counsel at global FinTech company Tilt, to explore what modern in-house legal leadership really looks like. From surviving the 2008 financial crisis at a top law firm to building lean legal teams across multiple countries, Louis shares how judgment, operational thinking, and adaptability matter more than rigid legal frameworks. The conversation dives deep into legal operations, AI-driven efficiency, law firm economics, and why today’s lawyers must think like business partners—not just risk spotters.
Read a detailed summary: www.spotdraft.com/podcast/episode-03
Topics
Introduction: 00:00
Louis Shansky on leading the global legal function at Tilt and overseeing multi-jurisdiction operations: 01:07
Early career motivations: music, logic, and choosing law school later than peers: 02:12
Lessons from touring as a punk rock musician and how logistics shaped operational thinking: 04:06
Entering Big Law during the securitization boom and learning structured finance on the fly: 10:24
Experiencing the 2008 financial crisis inside a capital markets practice: 12:35
Surviving Big Law layoffs and carving out value through diligence and adaptability: 16:51
Why success in Big Law led to partnership—but not long-term fulfilment: 25:09
Moving in-house at a FinTech startup and leveraging niche expertise to reduce risk: 30:27
Learning to recalibrate legal advice for business realities and risk tolerance: 33:09
How Louis builds lean in-house legal teams around core business risks: 37:13
Legal operations without headcount: tools, efficiency, and rolling up sleeves: 44:26
AI’s role in automating legal workflows and reshaping law firm value –49:50
Rapid-fire round: 56:40
Connect with us:
Louis Shansky - https://www.linkedin.com/in/louis-shansky-b501246/
Akshay Verma - https://www.linkedin.com/in/akshay-verma-esq/
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
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Transcript
Trust in Professionals
00:00:00
Speaker
I've always thought that lawyers are kind of like doctors in that um like you don't know if you have a good doctor, you just know whether your doctor makes you feel like you have a good doctor. yeah um It's yeah very similar with lawyers. and And I think what gives a client comfort is to hear somebody they trust tell them the thing that they should or shouldn't do or um how to navigate a particular issue.
Introduction to Guest: Louis Shansky
00:00:32
Speaker
Welcome, everybody, to our next episode of Beacon Voices. I'm your host, Akshay Verma. I am the COO at Spot Draft. Really excited today to have a conversation with the general counsel of a fantastic company named Tilt.
00:00:48
Speaker
Louis Shansky. Louis, welcome to the podcast. Really excited to kind of unfold our conversation. I was i was so um impressed with our prep call. There's a lot of similarities that you and I have in our careers in lawyering and doing operational things. So I'm excited to dig into those areas.
Role at Tilt and Company Overview
00:01:06
Speaker
But let's get started with just who you are a little bit and kind of what you do at TILT. Sure. um So first of all, thanks for having me on. I am general counsel at a company called Tilt.
00:01:19
Speaker
Tilt is a global fintech that uses AI power cash flow underwriting to expand access to fair credit. um So we have a suite of financial products um that we offer in the US. We also have subsidiaries offering products in Mexico, the Philippines, and India um with you know aspirations to continue growing globally. And so I oversee the legal function, um not only in the U.S., but across all our geographies as well. And and how big is the company in terms of employees and and how big is the legal function?
00:01:55
Speaker
Globally, the company is around um a little under 400, I think. um And the legal team is currently for globally. okay I was going to say we have ah three three lawyers in the U.S. and then one in the Philippines right now.
00:02:11
Speaker
Got it. got it wellll We'll dig more into kind of your role at Tilt and the company and the challenges that you're up
Early Career and Punk Rock Band Experience
00:02:17
Speaker
against. But um I'd love to start with just talking a little bit about your early career. And you're one of those rare lawyers who've done and seen a lot in that path. But I love this question because I get asked it all the time. People kind of look at my resume and they're like, wow, you've done this and this. ah What made you go to law school in the first place? And and did you find what you were looking for there?
00:02:40
Speaker
um Yeah, so it's kind of funny. um ah Apparently, if you ask my parents when I was 10 years old, um they asked me what I wanted to be when I grew up. And I told them that I wanted to go to DePaul Law School in Chicago and I wanted to be a lawyer.
00:02:56
Speaker
And i have no memory of ever saying that, um but I ended up going to DePaul Law School and becoming a lawyer. um And it's it's kind of funny. I had um ah gone to undergrad and started a ah punk rock band with some buddies that sort of took off at very small scale. And so when I graduated, we tried to do the band thing for a while. And so when that, you know, inevitably fizzled, you know, I said, okay, what's next? And, you know, I sort of started like thinking about law school again. i think what um attracted me to law school is and I'm a very analytical and logical person. You know, there's a um very... sort of um appealing nature of that clean, you know, logicing your way through a decision-making process or analytical process. And the law seemed like the um the neatest fit for that type of personality because, you know, it's in theory how the law works. um And so, you know, decided to take the LSAT, did reasonably well, and, you know, ended up making the jump.
00:04:06
Speaker
<unk>re We're going to have to, i somehow I missed this in our prep call. We're going to have to talk about the punk band. We're going to have talk about the punk rock but rock band for a little bit. Tell me about that. Like what inspired that? is Certainly going on the road, being a musician, fame and singing in front of crowds and playing in front of crowds, I'm sure is allure. But like, talk a little about that. Like what part
Transition from Law School to Job Market
00:04:26
Speaker
of you, because as i would I would argue that being a lawyer and being a punk rock rock star are like on two opposite ends of the spectrum when you think about careers.
00:04:36
Speaker
and And you dabbled in both of them and now you're incredibly successful lawyer. But but tell me a little bit about that journey. ah You know, so I come from sort of a musical family. My dad is a classically trained pianist and, you know, we're, you know, always had music playing in the house. um You know, i was in high school. I sort of, you know, got into punk rock through a friend of mine and, um you know, picked up the guitar. The great thing about punk rock is you.
00:05:01
Speaker
you don't have to be particularly skilled as a musician to play it. So, you know, you learn a couple of chords on electric guitar and yeah you can play like half of the punk albums that are out there and um ah just started making noise, you know, with some buddies in a basement and that turned into, you know,
00:05:18
Speaker
playing a couple house shows when I was in college, and then that turned into playing some local clubs, and that turned into playing you know some nearby cities, and that turned into getting offered a you know very small record contract.
00:05:33
Speaker
Recording an album and then, you know, we did some touring, you know, three guys in a very old van, you know, driving, you know, for days on end. um ah Coast to coast a couple times. Wow. um And it was it was a lot of fun. You know, we met a lot of people, saw a lot of things that we never would have seen otherwise. um You
Surviving the 2008 Financial Crisis
00:05:55
Speaker
know, got to play our music in front of, you know, thousands of people, um you know, over the course of our career. um And, ah yeah, it was it was a great time. it was not particularly lucrative. ah You know, it the the classic, like, you know, you're you're making enough money at the show to pay for your gas to get to the next show yeah kind of thing. um
00:06:17
Speaker
but But it was great. Yeah, it was it was a lot of fun. And, um yeah, would would never have given up those those years. I think that was one of those, like, unique formative experiences that ah not a lot of folks are are fortunate enough to get.
00:06:30
Speaker
No, and it's just so your your point around learning a few chords for a punk rock actually resonate. I just picked up guitar about a year ago. And it was one of those things for me where it was like, you know, I'm probably, i don't know,
00:06:47
Speaker
a little closer to retirement than I was five years ago or 10 years ago. And so for me, there's ah there's a big drive to learn new things and keep your mind you know growing and and and all of that. And so I picked it up and and my guitar teacher was very, very adamant. He said, I want you to learn on the acoustic first and you're gonna learn chords and you learn all it and it's gonna be really hard.
00:07:13
Speaker
It's gonna be really, really hard for you. And if we get through that, And if you stick with it, for he's like, give me six to eight months, then I will allow you to play the electric guitar. And then you will see how much easier and more fun guitar playing can be. So we are just now starting songs from the Nirvana age and some of the others. I just learned a ah car ah ah car song all the way through, which is like,
00:07:39
Speaker
six chords, they're all power chords and I can play the whole song all the way through and it's a lot of fun. But that that one particular comment around you know being able to pick it up really resonated. and And here's the other thing, I mean, this is not a garage band story for you. Like you guys were on the road a little bit and you were you were you were really learning and and kind of being out there. um I'll ask you this one follow up and then move away from from punk rock playing, but What was it your biggest learning lesson from that experience that helped you ah in terms of being a lawyer? And you can obviously see say that you can answer this with the benefit of hand of hindsight.
00:08:18
Speaker
I think um I don't even know if it's like, strictly speaking, a lesson as a lawyer, although definitely has some applicability in an in-house context.
00:08:30
Speaker
is um just planning and logistics. You know, in you're one of the things about playing in um punk rock at the time, at least, i you know, it wasn't quite as big as it as it got eventually, um is, you know, you play a lot of, like,
00:08:47
Speaker
small clubs and basement shows where, you know, you'd walk in and somebody would realize like there's, there's no microphone, they have a PA set up, but there's no microphone or, um you know, or the inverse, right? You know, there's, there's no speakers and, or um somebody forgot to bring the cables for everything, you know, and, and um taking it a step further, like on, on the band's end,
00:09:10
Speaker
you know having to plan for, hey, how are we going to get from a to B? Do we have enough time? or can we fit all our equipment? If we need to bring our own PA for this show, does that fit in you the van? um You have enough like um missteps where you show up and things aren't thought of that you realize the importance of like thinking about the details and the planning. and so um In circumstances where I've been in-house and, like for example, we're talking about launching a new product, yeah I'm usually the one in the room saying, okay, so that's that sounds great on paper, but like how are we actually going to do this thing? If a consumer wants to you know yeah use this feature, like how's that going to work on the back end? Is that going to be manual? Who's going to be pushing the buttons? Is it going to be automated? So that's definitely keyed lot of forward-thinking instincts that that I have.
00:10:03
Speaker
It has to be operational in nature. and And we'll get into this a little bit as well. it's just how much more operational today's in-house lawyer needs to be than even just a few years ago. It's such a demand of the job and the role and certainly legal operations and legal technology play a significant role in that. But we'll get to that in just a minute. all right, so you gave up your punk rock days.
Career Shift to In-House Counsel
00:10:27
Speaker
I'm sure you still play. I'm sure you still dabble. it's's it's so much The music is so fun. But you go to law school, you come out.
00:10:34
Speaker
ah What are you thinking at this point? Like, are you are you thinking i am going to big law and I'm going to go make partner? Are you thinking this is a stepping stone, something else? Like, what's your thought process? Like, is there one?
00:10:46
Speaker
I was thinking I need a job. um So, you know, i I went to law school because of the band years. i went to law school, ah you know, a few years later than um a lot of folks do. And so, you know, I i graduated when I was 30 years old with, you know, six figures in law school debt. And, it you know, I just knew I need to be able, at minimum, I need to be able to like pay my student loans. Right. And, you know, and everything else we'll figure out after. you I had a very tough time finding job. I did very well in law school, but for you know whatever reason, um you know I probably sent out about 100 resumes between you know sometime in my second year and you know when I eventually got a job.
00:11:29
Speaker
yeah And, you yeah know, so I was i was ready to to do anything, like, you know, any place that would have me. And um so when I got an opportunity ah to interview at ah Mayor Brown, um they were hiring for their structured finance securitization practice. And the recruiter called me up and said, you know, hey, we saw your resume.
00:11:48
Speaker
um I think I'd applied for a corporate, a spot in the corporate um group. and And they said, we actually... you we don't need anybody in corporate, but we do need somebody in securitization. Would you be interested in um interviewing for that role? And I said, absolutely. And then I got off the phone and I i Googled securitization. I had no idea what it even meant, you know, but didn't matter. i was, ah you know, just looking for a place to land at that point.
00:12:13
Speaker
Very cool. And where did you end up landing? I ended up landing in Mayor Brown's securitization group, and i I ended up landing there in ah the fall of 2007, which, if you remember your history, is sort of an interesting time to have been entering a capital markets-centered practice.
00:12:35
Speaker
i' I mean, I'd go so far as to say anything related to banking globally, real estate markets, capital markets, and all the legal support that goes along with that, which tended to, for the most part, go to these very large firms.
00:12:51
Speaker
um Did you
Differences Between In-House and Law Firm Work
00:12:52
Speaker
know there was a tidal wave that was going to hit the financial markets? like Did you have a sense of that at all? you know I was so unsophisticated at the time. like I'd read the headlines about rising you know mortgage delinquencies and you know that some of the early warning signs that banks were calling out. But I don't think I really like put two and two together that, you know, um if there's this like massive impact on credit and balance sheets of banks, like what that's going to mean for, you know, a securitization program at, you know any of the major issuers and what that's going to do to the market for those securities.
00:13:29
Speaker
um You know, and in this sort of naive way, I thought, well, you know, they wouldn't have hired me, you know, if if if they thought there was going to be some, you know, massive dry up in the market, right? So everything's going to be fine.
00:13:48
Speaker
ah That's, that's you you actually raise a really interesting point. So i i graduated in 2006. So it's just a year before you. And um my first job was at Pillsbury in the environmental group.
00:14:01
Speaker
I got an offer letter in april March, April of 2006, which had a very nice number in a base salary associated with it. And then within about
Building Effective Legal Teams
00:14:14
Speaker
three months, so this must have been during the time that I was studying for the bar, um I got another offer letter where ah the baseline had been increased by 10K.
00:14:25
Speaker
And I had no idea what was going on. But already this kind of race for talent in these big law firms had started. no yeah And I remember feeling a little bit like, wait a minute, like, you know, I obviously am very happy with my initial offer, like so excited. I've never made this kind of money before. I'm so excited to do this.
00:14:45
Speaker
And this firm, which has thousands of associates, is going to be increasing their pays significantly. I was like, can they afford this? I had no idea what law firm revenues were like. I didn't i didn't know any of those kinds of things. But I do remember having that feeling.
00:15:02
Speaker
um And then, so I started, you know, ah October of 2006. In December, they went up, or maybe it was January, February, they went up 10K again.
00:15:14
Speaker
Because one firm, and I can't remember which firm it was, had decided that in order for in order for that firm to fight for the top talent, they had to pay a little bit more than everybody else. And so all of a sudden you just had this race to the top. I'm not going to call it a race to the bottom, but you had this race to the top. And within a year, actually less than that, within six months of my start date, my starting salary had already increased by 20K and I hadn't even learned how to be a lawyer yet. no and so So we were really kind of like, okay, yeah the the junior associates were like what's going on? Like what's, you know, where is this? I had no clue. I had even less of a clue in my practice, which was an environmental practice.
00:15:55
Speaker
about capital markets or the real estate bubble or anything like that than you did. Yeah. now those Those were, I mean, you maybe it still is, but those those were wild times at the big firms. I think I i got a $15,000 raise. I signed my offer letter in like June or July. i think it was July. And I started that September and I got a $15,000 raise in between those two events. So by the time I started, i was already making 15K more. It was kind of nutty.
00:16:24
Speaker
Yeah. i mean, especially in your first couple of years of practice, it's so easy to move firms. And, you know, if an associate's like, oh, this firm's offering me 15K more, you've got six figure law school debt.
00:16:39
Speaker
I'll be like, yeah, I'll go there. It's the same work. Let's all be honest. I'm going to be doing the same work. Maybe I even like the people more. I don't know. Yeah. It was an interesting dynamic that took it. Okay. Then, you know, 2008 happens.
00:16:54
Speaker
um What are you thinking? Like, how how are things flowing around you? What's that like at Mayor Brown in in the late fall, early winter of 2008? I
Impact of AI on Legal Operations
00:17:04
Speaker
mean, it was um it was actually ah prior to then because, you know, the um I think the the activity in the mortgage markets and um the the securities, mortgage-backed securities that were starting to show those indicators was,
00:17:23
Speaker
I think that kind of started to spook the capital markets sooner than you saw the the big headlines. And so um i and this might be like a a slight exaggeration, but i don't I'm not sure I'd build a single hour in that stub when I started in September through the end of 2007. I don't think I'd build a single hour.
00:17:50
Speaker
um i I think I shadowed one securitization that was, you know, going on at the time and, you know, might have like re reviewed a closing list or something like that. But, you know, there was no deal work um or very little.
00:18:05
Speaker
i sort of spent most of my days just like doing voluntary CLEs and trying to do some proactive reading about securitization. So I would not be a you know, complete novice when I actually got billable work to do.
00:18:20
Speaker
um But by the end of the year, yeah I'm like leaving the office 5 o'clock every day, and I'm only even staying that long because I don't want to be the guy who leaves too early. But you know um but by the end of the year, I was like, okay, you know this is weird. like it feels like i feels like I should be doing something. And then um I think, you know, the the messaging around what was happening became a little more clear and overt, like into, you know, I call it the spring of 2008. And so, you know, there were still some deals going on, but most of them were ah were non-US deals. And, you know, so they weren't really coming to to our group or my group. And, you know, quickly what we began to be asked to spend time on were actually diligence projects. And so you'd have a bank that had, you know, big portfolio of CDO exposure or MBS exposure, and they'd want to know, like,
00:19:24
Speaker
hey, when can I call it default? What are my rights when you know I call a default? um you know What are the threshold, the performance thresholds that can trigger default?
00:19:35
Speaker
And so you know in in an effort to just... do something, you know I kind of raised my hand and said, hey, you know if like there's anything I can do, and I said, well, actually, you know and if two want to start coordinating this this you know massive diligence effort for you one of the banks that had all these CDOs?
00:19:53
Speaker
um And so I'd say there were a couple projects like that. I'd say most of the billable work I did in 2008 was of that nature. it was
Advice for Young Lawyers and Mentorship
00:20:05
Speaker
It was not active deal work. It was just sort of deal um document analysis for you know various banks that were trying to figure out what would happen if it all hit the fan, when it all hit the fan kind of thing.
00:20:20
Speaker
All right, but you survived, ah like many of us. says it I mean, there were many of my colleagues and friends who unfortunately did not. you know they were They were laid off with the massive layoffs that kind of cascaded down from the banks going under to the to the law firms because many law firms had large practice areas and uh, and lawyers and partners dedicated to that work. And if that work is gone, that's it's tough to survive that, but you did, and you came out on the backside of that. And and so what was that survivor feeling like? and And did it, did it change the way that you were thinking about being a lawyer?
00:20:54
Speaker
Yeah. I mean, you know, during that period, I think to your point, I think that fall, um, my timing is right. The fall of 2008, I think we laid off, Mayor Brown laid off 33 associates in the structured finance group. wow Um, one group.
00:21:11
Speaker
Yeah. Just, just in structured finance. Yeah. And, um, this is, that you know, Mayor Brown is a massive structured finance practice. They're one of the, um, you know, leaders there and, So they they were shedding a lot of people. um I think um we had started, they'd started to lay off like a few members of my starting class. You know, once they hit that one year mark, everybody was, you know, everybody's on the table. um And it really was a like,
00:21:38
Speaker
you know, keep me away from the chopping block. I'll, I'll do, I'll do anything. I'll do anything. And so there was a lot of, like i said, diligence work, but I would also volunteer to help other groups, you know, like our tax controversy group would have big document review projects that they needed help with and say, hey I've got time, you know, if you need another body, yeah um because it it really was about just like staying busy, like doing whatever you could to stay busy.
00:22:03
Speaker
And then by, I don't know, maybe like the spring of 2009, things had started to obviously, we were you know still amidst the recession, but the capital markets had started to show signs of opening up at least for um some of the you know well-known kind of blue chip ABS issuers, you know the um you know, capital ones and, uh, uh, city banks and, you know, the folks who would securitize their, um, consumer receivables.
00:22:35
Speaker
And so, but what had happened was, know, number one, we'd laid off a bunch of the junior associates in the group. Number two, um, at that time, law firms were deferring their starting classes. So there like was, don't think there was a class of 2009,
00:22:51
Speaker
um And so you're left with like a handful of associates, myself included, junior associates who are available, you know, to do the, you know, the junior associate work on these very paper intensive deals.
00:23:05
Speaker
And um no class immediately behind me, you know, to sort of compete with. And so it sort of created a moat where, you know, um i was one of a few people left in the group who was available to do the deals.
00:23:20
Speaker
um And that was the case for year and a half to two years. yeah And so it gave me a good head start to not only like learn the deals, but build relationships with the clients um and sort of get sticky, you know, in those in those spaces so that, you know, I became a third, fourth year lawyer. Like I had client relationships and I had, you know, a niche that I'd carved out for myself. And I think that was very important um and a sort of lucky break. You know, it's sort of a theme throughout my career. I think I'm better to be lucky than good, you know. Absolutely.
00:23:59
Speaker
And, and i you know, I think that um being around, you know, being being the one who had who had hung on, um you know, when people were getting, ah you know, shoved left and right um actually put me in a, you know very fortunate position when deals started to flow again, for sure. Yeah.
00:24:19
Speaker
um And so at this point, are you thinking, yes, it's time for me to kind of stick it out here and make partner? Anything else kind of going through your mind in terms of where you're going take your career and why?
00:24:31
Speaker
No, I mean, you know, at the time, I think that was very much the um that was very much my my mentality. You know, I i enjoyed the practice. I enjoyed the clients. um I worked on a bunch of very interesting deals um and you know i was I was successful at it. I seemed to be doing good job. People like me, the clients like me. um And so, yeah, it seemed natural that you know I would continue on that path and you know until I made partner or or didn't, right? It's up or out at the big firms. So I figured I'd you know ride that out for my yeah know seven years or whatever it is and then ne see see what happens.
00:25:08
Speaker
Yeah. I wonder if it's still a seven-year journey. My guess is it's ah it's quite a bit longer now. But you did. You went and you became partner at Mayor Brown, and yet you are not still a partner at Mayor Brown. You are a general counsel at TILT. In fact, this is your fourth or fifth or maybe even more in house roles.
00:25:28
Speaker
um Many, if not everyone who goes into the law firm world intentionally sees making partner as kind of one of the ultimate goals in lawyering. And yet you decided at some point after becoming partner that it was no longer going to be for you and that you were going to try the in-house world.
00:25:48
Speaker
Talk to us a little bit about that decision making process. What really drew you into that? What about the law firm life made you say, you know, thanks, but no thanks. I've kind of.
00:26:00
Speaker
I've seen this all and it's not, not at all what I thought it was going to be, or it's exactly what I thought it was going to be, but I'm not going to go forward. Like tell tell us a little bit about that story. Sure. You know, I think, um, I, so I've never been maybe a slight digression, but I've never been somebody for whom, um, like money or financial reward is the primary motivator.
00:26:25
Speaker
And so, you know, it's always about enjoying the way that I'm spending my days. You know, if if I'm doing a job, I want to enjoy it. i don want to enjoy the people that i work with. I want to enjoy what I'm doing. I want to find it stimulating and engaging.
00:26:40
Speaker
And that was very much the case as an associate um at Mirror Brown, doing deal work, right? um But what happens when you become a partner is that that shift um between being ah um a like a deal worker and ah a true lawyer versus suddenly becoming a revenue generator and a business developer um becomes very important because, you know, as you escalate through the ranks of of partnership, it's not quite an eat what you kill model at most of the big firms, but, you know, there's a few degrees away from that. And so there's very much, you know, an expectation that you're you're going to go out and do pitches and you're going to take clients to dinner and you're going to do presentations and you're going to write articles and you're going to do all these things that,
00:27:32
Speaker
you know, are not the thing that you just spent the first seven years of your career doing. um They're really focused more on business development. um And then, you know, other kind of ancillary law firm related um ah tasks like, you know, mentoring junior associates, engaging in recruiting and engaging with summer associates. all All the big firms love to have young partners to trot out you know, to the summer associate classes so they could, you know, feel kind of hip and cool.
00:28:03
Speaker
um And so what what ended up happening is I found myself like a couple years into partnership. Yeah. spending, you know, 50% of my time doing real lawyering and 50% of my time doing all this other stuff and firm administration stuff. And, um and it's, it just wasn't fun for me. It wasn't what I enjoyed. And I think, um so that was like, you know, my first inkling that, you know, maybe this wasn't for me.
00:28:33
Speaker
And I didn't know whether that was the product of being at a big firm or, the you know, product of being a partner altogether. Um, and, but I think the other thing that started to become apparent to me is, you know, I'd had a handful of, um,
00:28:48
Speaker
ABS issuer clients that I'd been working with for years. I did a lot of work in auto loan securitization, so I worked a lot with the, you know Nissans and Volkswagens and, you know, so-and-so of the world.
00:29:01
Speaker
And um I really loved those clients. You know, I'd had good relationships with the people um at those companies, but what would happen is, you know, They call you up and say, hey, we're going to do a deal. Here's our timeline.
00:29:16
Speaker
And yeah you draft the documents and you negotiate the documents and yeah you launch the deal and you close the deal. um And then client disappears you know for four to six months. And then they come back with the next deal. But like...
00:29:32
Speaker
they're telling you all this stuff that has happened to them between the last deal and this one. And it's this very transactional relationship you have with, you know, the company where you, you help them do this very significant thing in their kind of growth trajectory.
00:29:50
Speaker
then you don't get to see what happens as a result of it. You don't get to see how they figured out how to comply with the covenants or, you know, how the deal is performing or, you know, why they're making these changes between deal A and deal B. And so there was something like a little bit unsatisfying about, you know, just getting these glimpses.
00:30:10
Speaker
And I thought, well, you know, it's sort of be fun to be there. You know, it's sort of be fun to, you know, like see how this deal fits in to running their business and, you know, how they're evolving, you know, year over year. And so those two ah insights together, I think, led me to start thinking about going in-house.
00:30:27
Speaker
Okay. And where did you step in first? What was your, you know, was it intentional? Was it something that came across your desk? Was it a client who said, Hey, Louie, come on in. Like we need you here. And and can you step into these shoes and and help us run from the company from the inside?
00:30:42
Speaker
You know, um again, ah better to be lucky than good. So i um you know, I think i had maybe applied for one in-house role, but it was sort of half-hearted. I wasn't i wasn't convinced that that's what I wanted to do. I sort of put a resume and see what happens and nothing happened.
00:30:59
Speaker
And then um ah one day i got a just random LinkedIn message from one of the co-founders of a company called Upgrade. They're a um fintech lending platform.
00:31:12
Speaker
um And they they were nothing at that point. um And ah the co-founder had said, hey, um i am I ran Capital Markets at Lending Club for a number of years. um I am ah co-founding a new company with ah Renault Laplanche, who's been the founder of Lending Club and a couple other Lending Club ah vets.
00:31:35
Speaker
um It's going to be a Capital Markets sort of dependent a company, and so we need some in-house Capital Markets expertise. yeah I got your name from you know mutual acquaintance. Would you be interested in talking to us?
00:31:51
Speaker
And um I think what made it intriguing was, you know number one, in-house opportunity. Number two, like this was 2017. This is like right in the thick of you know seeing tech companies explode and yeah all these fintechs going public. Lending club had gone public. A few others had gone public. And I thought this is like the ground floor of, you know, maybe the next multi-billion dollar company.
00:32:19
Speaker
And they need this niche skill that I happen to have. Right. It's a, you know, it a very, um, cause that's the thing which, you know, maybe we can talk about at some point is, you know,
00:32:32
Speaker
When you go in-house, I think the yeah the skill set, the expectation of your skill set is often more broad than you know um like having this particular expertise that a lot of law enforcement lawyers do. yeah And so there is some, um it can be a little bit intimidating to think, you know oh geez, I'm a securitization lawyer and now I'm going to become a general counsel somewhere. like that That leap can be intimidating. And so the idea that I wouldn't really be expected to do much that I couldn't already do.
00:33:03
Speaker
You know, it sort of made it a no brainer um when when that opportunity came along. Yeah. Look, I think in addition to kind of the um the specific issue of your level, your your type, level and depth of expertise as an outside counsel,
00:33:22
Speaker
The transition just on that issue going in-house is difficult. But there's also a reason that that many outside lawyers do not succeed in-house. There's a mental shift that goes along with with transitioning to being in-house world. There's a way of operating. There's a way of thinking. There's a recalibration of the concept of risk and looking at things from a business perspective more than anything else, rather than really kind of putting your lawyer hat on and and diving deep into a legal issue. What was, and it sounds like you navigated that pretty well. A, would you agree with that statement? Like, is is that something that you would agree with? And B, if if that was a challenge for you, how did you overcome that?
00:34:06
Speaker
Yeah, I mean, I think um I'll leave to others to say whether I i navigated it well, but, um you know, navigated, I did one way or the other. And, um you know, I think there's a steep learning curve, right? Because i think what happens, at you know, at a law firm, you your For most law firm lawyers, your um sort of convention is to give like the the academically correct answer or advice. Like, well, the law says this, you know so you can't do A, you must do B. And um you know sometimes when you're in-house, you yeah say that to your colleague you know on the business side, and they go...
00:34:49
Speaker
we we literally cannot do B. Like it's not, there's we have no way of doing B. So yeah, yeah tell me something else. yeah And you know, you, you have to learn to then like risk adjust your advice at that point. Right. Because you, you have to sort of understand the business. You have to understand like how the different aspects of the business function, what they can and can't do, what things are important to them and you know, what things they don't really care about. Yeah.
00:35:19
Speaker
And then you have to figure out for that specific issue, like, how big of a fire is it if we get this wrong? You know, is this just an annoyance that we'll have to clean up in a few months? Or is this like, you know, an existential threat if we get it wrong?
00:35:35
Speaker
And you you have to quickly calibrate on where where do you, you know, sort of put up a stink and say, no, no, no, we got to figure out how to do B.
00:35:46
Speaker
Versus saying, okay, we can't do B, let's do like you know a A-, minus you know some somewhere close to B, and yeah see if we can create like the you know the best story around why we're doing not quite B.
00:36:02
Speaker
um But it took a couple of months and a few exchanges with you know my business partners at Upgrade, I think, to get to that point where I could give you know um ah in the cliche term actionable advice, know practical actionable advice.
00:36:20
Speaker
ah to I mean, it has to be actionable. Otherwise, on paper, it's really not going to help anybody. Yeah, but it's um but yeah, it was it was definitely a learning curve. And I think, um you know, what helped me out a lot was i was fortunate to be surrounded by um experienced business operators. You know, that the team had come from another successful company.
00:36:43
Speaker
had similar model. They knew like what they could and couldn't do largely. So it wasn't like, you know, i was presented with, you know, wild scenarios of, you know, something crazy they wanted to do. It was usually matters of degree and saying, okay, well, yeah, I think we can get there if we do it this, this slightly different way. And, um but yeah, there was a lot of, a lot of iterating, ah you know, in those, those first few projects I did with them for sure. Yeah.
00:37:13
Speaker
Like, yeah you know, being in-house is is monumentally different, obviously, for for a variety of different reasons. I'd like to focus in on two of them for the next part of our conversation. The first one is around people.
00:37:25
Speaker
We'd love to get your thoughts around what you think works well with legal teams, what you look for as you think about building out legal teams and and kind of your little bit little a little bit of your thought process on that.
00:37:38
Speaker
And then we'll switch gears after that to talk a little bit about the role of legal operations and legal technology in your in-house world. Like, let's let's start with that. but let's start with the people side first. And you you you you get into your first in-house role. I'm not sure if you got a chance to build out the legal team in some fashion or not. But like, how do you think about those things as an in-house lawyer?
00:37:57
Speaker
So, um, Sort of in typical lawyer fashion, I'm going to answer your question about building a team by starting with talking about myself. um i I always, to to that first comment about joining Upgrade, you know I always find, like when I'm looking at any job opportunity, I always think about what expertise do I have today that will be applicable and useful in this new role because i never want to walk into a role where everything is foreign and i'm I'm learning, you know, every aspect of my job on the job, right?
00:38:39
Speaker
I don't think it brings much value to a role like that, number one. But number two, from a confidence perspective, you know, i think it helps with your self-confidence to come in saying, hey, this thing I'm going to be doing, i know cold.
00:38:53
Speaker
And you can ask me any question about capital markets, securitization, and I'm going nail it. And so number one, that helps me sort of continue to feel like I'm a good lawyer. I can do this. And number two, um it gives me some credibility with the team for those moments where I say, i actually don't know, you know, this area of the law. You know, I need a minute to like go get smart before I give you an answer. And so that's been sort of like a guiding principle for roles that I've considered taking.
00:39:26
Speaker
So what does that have to do with building a team? That is also a guiding principle for how I build teams. um And what I mean by that is, you know, at a startup in particular, you don't have the resources to hire like subject matter expertise, expert for every, you know, area of the business. You can't walk in on day one, series A company and say, okay, I'm going to need a corporate lawyer, an HR lawyer, you a regulatory lawyer, they're going to say no. Nor would you get one even if you asked for it. Yeah, exactly. They're going to say, you know, you you get one, you get one, you get one lawyer, you know, figure out who you want. um And so,
00:40:08
Speaker
the The first thing I do, um you know, in that context is make sure I have a very strong understanding of the business. Like I think the you know first step to building a team is you have to really thoroughly understand the business you're in. Yeah.
00:40:23
Speaker
where the legal issues come from and which ones are the most important ones. So, you know, I've spent a lot of my time at consumer or financial services companies. So that means a very heavy focus on, you know, consumer protection law, um making sure that, you know, from product perspective, like giving the right disclosures, presenting things in a clear, and transparent way, operationally, where, you know, you know, handling consumer accounts the way that they expect them to be handled.
00:40:51
Speaker
um And so that's like a critical aspect of that business, that sort of business. And so you start with something like that and you say, okay, so I need the consumer regulatory side to be covered.
00:41:07
Speaker
And there's going to be more legal work to do than just, you know, consumer finance. Yeah. But, Who do I hire?
00:41:18
Speaker
you know, ah you don't hire somebody who has no experience in consumer finance. you You need somebody who feels like they can do that piece of the job very well. Right. who You know, so I have some experience and expertise. Right.
00:41:34
Speaker
And who you think has enough of a nimble mind that if you say, hey by the way, here's a commercial agreement that needs reviewed or there's a random ah HR issue that the people team needs help with, that they can flex into it and not be intimidated intimidated by it and you know get up to speed relatively quickly. And so...
00:41:54
Speaker
um Sort of expanding on that, like if you if you cover off like the most important aspect of your business, so for us, you know, consumer protection, then you go, well, what else what else is there that drives a lot of risk and legal work? And so, you know maybe depending on the business that's capital markets or maybe it's on the commercial side, maybe you have a lot of partnerships that you're constantly negotiating um But I take that same lens as I sort of um stack rank the needs. You know, OK, we got consumer finance covered. Next issue we need covered is capital markets. So I want somebody who can do capital markets plus, you know, um and I'm going to expect them to do some more things. But I want them to come in with this core competency that they're going to be able to exercise on a daily basis while flexing into some other things.
00:42:48
Speaker
um And I just sort of keep, you know, um adding to the team on that principle, if that makes sense. Yeah. and And also, I mean, I think the the thing that I'm hearing from you on that is that it's not just the lawyer, but the person.
00:43:02
Speaker
um i have I don't know if I stick to this 100% of the time, but to me, irrespective of the kind of role that I'm looking at hiring for lawyer, legal professional, something else, I think resilience and growth mindset set you up for success.
00:43:23
Speaker
To your point, particularly as a lawyer, if you're brought in to do capital markets work, restructured finance, you should have some experience in those areas. I think that's probably table stakes.
00:43:34
Speaker
But then especially in the in-house world, having having the ability the mental um curiosity and drive to learn new things, which are going to be needed. um Everybody in-house needs to be a little bit of a privacy expert, a little bit of a privacy and this in this day and age. yep And we'll get to this part in a minute.
00:43:55
Speaker
ai everyone's got every lawyer and legal professional and really every human being on the planet is going to need to learn something about AI, how to use it, how it works and things of that nature. So having that resilience and growth mindset, I think are critical, irrespective of the of the kind of role that you're that you're hiring for. And I think if you can do that with the the subject matter expertise to some level in depth being table stakes, I think you've set yourself up very nicely for whatever whatever team that you're thinking about building. um All right, so let's let's switch gears a little bit. So we've talked about the people side of the equation, but obviously operational expertise, operational know-how, um you know coming out of the financial crisis, as we were we were talking about earlier, one of the things that became incredibly different post-2010, I would say, was that ah in-house lawyers, GCs, CLOs, no longer had the kind of carte blanche that they had
00:44:53
Speaker
pre-2008 to spend and hire the way that they wanted to. There were some significant screws that remain today that gave birth to the rise of legal operations to a great extent. And now in the last seven, eight years, legal technology has played a prominent role in all of that.
00:45:12
Speaker
Talk to me a little bit and our listeners little bit about the role that legal technology has played for you. And if to any extent you've dabbled in legal operations or worked with strong legal operators, we'd love to hear about that as well.
00:45:25
Speaker
um So it's funny, at um other than ah my brief stint at Robinhood when my last company was acquired, um I've always been at relatively early stage startups where, you know, to your point, you know, legal headcount is, you know, at premium and, you know, um at most of the places I've been, dedicated like legal ops person has been, you know, a non-starter. It's like, don't, you know, don't need a human to do that. That's just, you know, rolling up your sleeves and, you know, doing some of the grunt work yourself and dah, dah, dah.
00:46:08
Speaker
And so I think like ah what's been important is to, to make, um the legal operations within the company as efficient as possible and finding you know tools and methods that enable that. right and yeah i I would not characterize myself as somebody who has like aced it and figured out the perfect system. I think I'm always learning and every company operates a little bit differently and it forces you to to tweak you know the style of legal operations a little bit. Right?
00:46:41
Speaker
Um, so I definitely think you have to be a little bit adaptive with it. You have to understand the context you're, you're working in, you know, how that business runs. Like for example, my last two companies have been fully remote, um, which, you know, obviously adds its own wrinkle to the operation side and coordination side. Um, but it's, it's definitely a, it's definitely a puzzle.
00:47:03
Speaker
In terms of tooling, I think, you know, to your point about AI, I think one of the most, um you know, we've I've tried at different stops a variety of tools, um you know, on the operation side, on the contract management side, and contract generation side. I think um what's really intriguing right now, and you mentioned the buzzword of the year, AI, right? What's really intriguing right now is um the number of new tools that are emerging that have like really fantastic potential use cases in legal operations, um even though they're not necessarily designed with lawyers in mind, right? um And so you know when you think about...
00:47:53
Speaker
um platforms like that facilitate workflow automation where you can say, hey, you know, when a um complaint hits my inbox, send it to chat GPT to parse it and identify the claim and identify the name of the consumer making the claim and then send that information to our database to pull the account records for that individual And then send all of that back to LLM to determine based on the account history and the claim, like, does their claim have merit? Did we do what they say we did?
00:48:33
Speaker
And then produce a summary of the merits of the claim in the background. and then spit that back into my inbox as a memo. yeah And so, you know, without ever touching the thing, you can have a summary of the complaint and its validity and, you know, any sort of bad facts that, you know, you might have created in the handling of the account or, you know, ah but you can more quickly dispose of, like, triage and dispose of those things in your inbox without doing all of the intervening manual steps of, like,
00:49:07
Speaker
pulling the account data, looking at the, you know, the customer support exchange history and all that other stuff. And so um I think things like that are um really exciting. you know, there are some places where it's not like quite there yet, but you can see the the frameworks in which those things can be built um and and just, you know, streamline the legal function incredibly.
00:49:33
Speaker
Yeah. As a profession and and and to some extent, you know ah i have to blame law firms for this because that's where we were all trained and that's where all legal work was done for so long before the in-house department was even created.
00:49:47
Speaker
um So much manual effort goes into every little thing. You said something earlier in your deal days um that you worked on these incredibly large paper intensive deals.
00:49:59
Speaker
Okay. Now, Large law firms are particularly well-suited to carry out that work because of their scale. So here's a spicy question for you.
00:50:12
Speaker
That has, to a great extent, been the bedrock and the foundational revenue generator for law firms for a long time. Large swaths of humans doing tasks that are billed out at exorbitant rates that i won't even get into in this one, but doing these big litigation matters and deals and things of that nature.
00:50:33
Speaker
AI has the potential to really change all of that for the one particular reason that we were just talking about, which is that there are so many manual tasks that are involved in doing a great portion of the of that work.
00:50:45
Speaker
Now, if those can be automated with some level of check, and let's let's say it works well, Do you fundamentally see law firms changing the way that they deliver work or do you see it going kind of business as usual? And I'll also remind our listeners that we're not talking to somebody who was a associate for six or seven years. We're talking with somebody who went on to become a partner at Mayor Brown and fully understands the economics of the law firm model.
00:51:11
Speaker
What are your thoughts on that one? Yeah, look, I mean, I think um I'll give you a real life example. So our our company um rebranded earlier this year and, you know, changed our name. And so, as you can imagine, on the consumer facing side, you know, agreements, disclosures, terms, you know, yada, yada, yada. We had probably...
00:51:35
Speaker
40 or 50 different consumer-facing pieces of paper that needed to be updated just to change our our name and, you know a couple other details.
00:51:48
Speaker
And that's the sort of thing that a human would have had to sit down and go through each each of them at some point. Today, it's possible for us to just take all those documents, upload them to an LLM and say, in every instance of this phrase, replace it with this phrase. In every instance of this phone number, replace it with this phone number. know, whatever other changes, spit them back out.
00:52:12
Speaker
You know, maybe a human eyeballs them or a sample of them to make sure it got it right. um But that that process happens in, you know, 15 minutes, right? Instead of the, you know few hours it would take somebody to go through and do all that manually.
00:52:27
Speaker
And so um now, whether you like it or not, That's possible and clients know it's possible. And so if you're a law firm and you're generating, you know, 60 documents for the latest securitization, know, of some repeat issuer and most of what you're doing in those documents, I know this from experience, is updating the deal name and some dates and things like that.
00:52:58
Speaker
And you're charging, you know, a dozen hours of associate time to do that. When I know full well an LLM could do it in a matter of minutes, like you're just not going to keep the business for that long, right? I mean, I think law firms have to adapt and and have to find ways to themselves leverage that technology um Because i do think there will continue to be a human element to lawyering, right? i mean like Absolutely. you know Putting ethical and and privilege issues to one side, which there are you know when it comes to using ah legal AI. um I think there's, you know, for the foreseeable future, always going to be a um a human element that the client is looking for. You know, they they want to hear somebody that they trust. It's an old analogy that is probably not perfect, but... I always thought that lawyers are kind of like doctors in that um like you don't know if you have a good doctor. You just know whether your doctor makes you feel like you have a good doctor. yeah um It's yeah very similar with lawyers. and And I think what gives a client comfort is to hear
00:54:10
Speaker
Somebody they trust tell them the thing that they should or shouldn't do or um how to navigate a particular issue. And so that substantive advice giving, I think, is, a you know, again, for the time being, is going to be a very human thing.
00:54:25
Speaker
But the more rote and mechanical tasks that law firms have traditionally done, they've got to find a way to make more efficient um to maintain that billing credibility. and yeah and And it also, I think, will help law firms emphasize the real value they do provide.
00:54:45
Speaker
in that advisory context, if that makes sense. Absolutely. That's why we went to law school. that's i mean that's That's the reason that we went to we at the law schools to become counselors, to provide our expertise and our judgment and our advice to our customers and our clients. By the way, I also want to point out in-house world, the in-house world is not immune to this whatsoever. I don't worry about it all. The dad's on the podcast.
00:55:13
Speaker
But very true of the in-house world. um you know So much manual work goes through, and this is why legal teams are really struggling. They really struggle with keeping up the pace for the business.
00:55:27
Speaker
um Almost, you know, I don't know, 98% of legal teams in-house are made up of lawyers who came from the law firm world. So until they get a feel for how they need to be more effective and efficient in-house and and automate tasks, stop doing tasks by prioritizing them, things of that nature, which is not something that we are trained to do in the law firm world, it'll continue to be an issue there as well.
00:55:52
Speaker
All right. Yeah, go ahead. maybe maybe Just maybe one quick thought on that. I mean, it you know in in agreement, um that's one of the things that I talked about with my team at our last onsite. And you know we brainstormed ways that we could use um a whole AI tooling to improve efficiency or, you know automate tasks that we're currently doing manually.
00:56:17
Speaker
And then everybody sort of took ownership of an idea and has to sort of flesh it out, you know, and see if we can build it into something before our next onset. And so we just always want to be thinking about how to how to keep up exactly. Yeah. Little mini hackathon and legal always ah always makes for good for good advice and for good outcomes. Yeah.
00:56:40
Speaker
All right, I promised you at the beginning, I've got three questions that I'm probably going to asking all of our guests. We'll see how they turn out over time. So here's the first question. What advice would you give to your law school self?
00:56:55
Speaker
So if there' is if you go back go back and talk to your law school self, let's say... I don't know, let's say in your 3L year, let's say you've you're almost to the end and now and you're going to be able to give this advice, obviously, with the benefit of hindsight. What would that piece of advice be?
00:57:14
Speaker
um I think it would I would probably just try to give myself a better... a better characterization of what's happening in law school. um ah You know, everybody, ah the thing you always heard was, you know, you don't go go to law school um to to be a lawyer, you go to law school to learn how to think like a lawyer. And, you know, there's some truth to that. But um the analogy I would use is like,
00:57:43
Speaker
you're To put it into a cooking context, you're not going to law school to learn how to make food. You're you're going to learn techniques. You're going to learn knife skills and sauce skills and you know whatever else. But the way in which you apply those skills can vary wildly from what you learn and the context you see in law school, right? you know law school is very litigation heavy ah context because you're generally reading case law.
00:58:17
Speaker
um And it doesn't give you any context for the you know, myriad paths that a lawyer can take. And so like, I don't think, I don't think something like securization ever occurred to me in law school because, know,
00:58:32
Speaker
Law school doesn't teach you that that sort of thing exists and the legal issues that go into you know structuring a deal and you know creating a bankruptcy remote entity, all these things. so um I think just like having a better understanding of you know what I'm actually learning and what's what's important to take away from law school and and what is you know really not necessarily what I'm going to see on the other side yeah um would have been helpful. so Would you reduce law school down to a year then?
00:59:02
Speaker
ah You know, everybody's got a different take on this. You know, for i'll I'll be blunt. Yeah, I would. For for me, I don't know that i that I added much to my skill set but in my second or third years. You know, I think the bulk of the...
00:59:18
Speaker
Yeah, the analytical honing happened in that first year. i think that's right. then And then just like most other professions, you can do an apprenticeship and get your hands on experience. OK, shifting the audience of this advice to law students and maybe even early legal professionals today, would your advice change at all or would it be the same?
00:59:41
Speaker
It's good question.
00:59:47
Speaker
i think I think maybe the only, ah you know, as far as law school itself, maybe it'd be the same. But I think in general, um what i would what I would say to like young lawyers as an audience is stay open and stay nimble. You know, there's a lot of different paths you can take. um There's a lot of different contexts in which you can apply your skills.
01:00:10
Speaker
um And they're all very, very different. The environments are very different. And there's sort of like a, I think for everybody, there's sort of like a magical set of circumstances that creates like a wonderful job for them.
01:00:25
Speaker
and you never know what that is unless you stay open to have something else that might come along, unless you feel like you've got your dream job, know, stay open, stay nimble. Yeah, I like that one.
01:00:36
Speaker
All right, last question. Looking ahead for yourself 10 years from now, ah what's the kind of path that you hope you've taken, not just in title, but also in the kind of work that you do?
01:00:49
Speaker
um You know, 10 years. That's either not that long or a very long time, depending on your fair anying under ah context. um I think, you know, i think that um what I'd like to be doing, whether it's my full time job or, you know, just something I do on the side, um I think that I think that I enjoy mentoring and helping other lawyers, younger lawyers, ah find their way, navigate their careers, navigate situations that they come across in their jobs.
01:01:26
Speaker
um And I'd i'd love for ah to have found a way to spend more meaningful time doing that, being a resource for for younger lawyers in some capacity. Awesome.
01:01:37
Speaker
Yeah, I love it. I love the aspect of giving back to this profession that has given us so much. Louis, thank you so much for joining me today. for our listeners, as a reminder, my guest today was Louis Shansky, General Counsel at TILT, our newest beacon voice.
01:01:54
Speaker
Thanks a lot. Thanks for having me.