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Ep 114: Building Outside the Box: Monica Zent on Legal Ops, AI, and Bold Bets
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In this episode of The Abstract, Monica Zent, serial entrepreneur, legal tech investor, and legal innovation pioneer, shares her journey of founding ZentLaw and helping shape modern legal operations before the term even existed. She unpacks the founder’s mindset, how to lead through ambiguity, and why taking bold bets early pays off. Monica also shares guidance on embracing AI, identifying scalable legal tech ideas, and forging unconventional paths in a traditionally risk-averse industry.
Read detailed transcript: https://www.spotdraft.com/podcast/episode-114
Topics
Introduction – 00:00
Embracing entrepreneurship from a young age – 02:23
Founding ZentLaw and challenging traditional models – 03:25
The founder paradox: balancing vision and risk – 05:49
Early struggles and inflection point for ZentLaw – 08:36
Overcoming pushback and evolving with client feedback – 10:09
Integrating innovation into legal workflows – 11:52
Handling setbacks and staying agile as a founder – 15:10
Choosing an unconventional legal path – 18:01
Advice for law schools and future legal professionals – 22:11
Becoming a legal tech investor and mentor – 25:55
Signals of a Scalable Legal Tech Startup – 27:14
Legal tech trends: compliance, privacy, and predictive AI – 29:03
AI’s role in reshaping legal teams and workflows – 31:18
Rapid-fire question – 36:18
Connect with us:
Monica Zent •
https://www.linkedin.com/in/monicazent/ •
https://www.monicazent.com/
Venture Legal Newsletter •
https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7302735858552446976
Companies •
https://www.lawinnovationagency.com/ • https://zentlawgroup.com/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
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. #legaltech #foundermindset #theabstractpodcast
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Transcript
00:00:00
Speaker
I've covered this concept that I've kind of coined called the founder paradox. And I believe that a lot of founders will have this sort of yin yang
The Founder Paradox: Balancing Risks and Faith
00:00:07
Speaker
quality to them where there is this ability to Maybe perhaps like in this example, right? Make some calculated risks, look around corners, kind of be able to sort of see out ahead, look a few moves ahead on the chessboard, but at the same time being able to also take a leap of faith, jump off the cliff while you're building the parachute, while you're flying down, right? That common analogy, but it's true.
00:00:30
Speaker
um When you're a founder, being able to sort of be comfortable with risk and ambiguity and be able to move through it. and And so I believe that a lot of founders have this sort of yin yang quality. And I've i certainly have seen that in myself.
00:00:42
Speaker
and But I also, and as I kind of touched on in my writing, and I'll expand on the theme in future writings as well about the founder paradox, but the I do believe it's very accessible for a lot of people. And I believe it's probably more accessible than most people think
00:01:04
Speaker
How do you embrace the founder's mindset, innovating early and leading differently?
Who is Monica Zent?
00:01:12
Speaker
Today on The Abstract, I am joined by Monica Zent.
00:01:16
Speaker
Monica's a serial entrepreneur, investor, pioneer in the legal tech space, and one of the earliest voices out there advocating for innovation and AI in legal.
00:01:31
Speaker
So, Monica's founded several companies that you may have worked with or heard of, Zent Law and and many others that have really helped shape the way that we think about what modern legal ops is and what legal advisory work looks like.
00:01:50
Speaker
She's currently serving as a principal at the Law Innovation Agency, where she's championing enterprise-wide legal innovation strategies. think as we're going to talk about today, your journey has never followed a sort of traditional playbook.
00:02:05
Speaker
Instead, it's really been defined by curiosity, reinvention, and a willingness to to make and take bold bets the future. Monica, thanks so much for joining me for this episode of The Abstract.
00:02:19
Speaker
Thank you, Tyler. I really appreciate it. It's awesome to be here. Okay. So as I mentioned, you founded several companies. You've really been at the forefront of what we would broadly describe as legal innovation.
00:02:33
Speaker
How did you first decide that you wanted to start something on your own? When did you decide, like, this is the moment to embrace being an entrepreneur?
Monica's Entrepreneurial Journey
00:02:42
Speaker
Yeah. Oh, gosh, this goes way back early in my life. I mean, I've been an entrepreneur for as long as I can remember. Starting something, acting on ideas, having ideas, moving on them and trying to create something.
00:02:54
Speaker
I mean, I'm a builder at heart. So it's been something literally always how I've been wired. I mean, from my early teens to kind of creating side hustles, ah summer jobs, weekend jobs, holiday break jobs, working my way through college, having side hustles during college, side hustles during college.
00:03:10
Speaker
law school After law school, I had multiple companies while I was working full time, finishing up at night and then studying for the bar. So it's literally just how I live and breathe. And it's hard to remember a time when I i wasn't quite frankly.
00:03:26
Speaker
Tell us a little bit about like the idea for Zent Law. and And when you launched it, did you feel like you were really like going against the grain, as it were, to to make that business become a reality or change the mindset around how legal services were
Zent Law: Innovating Legal Services
00:03:40
Speaker
delivered?
00:03:40
Speaker
Yes, very much so. um Yeah, it was a distinct use case that came out of that. i had already created a couple of companies and sold those. Those were my earlier startups. I had hired lawyers as well on my own. I had worked in a large law firm, kind of was able to see on the inside how things were operating.
00:03:55
Speaker
Really didn't like the billable hour model, really felt that there was another ah way to do this. Again, the entrepreneur in me came up with that idea of let's figure out another way and let's look at some some other kinds of models. And so I started learning about and studying up on the secondment model. I learned it was a concept that was derived from the military setting. I ended up applying that.
00:04:15
Speaker
I also looked into subscription models. I wondered why subscriptions, which are so common in other areas of our life, whether it was for cable or phone or internet, you know, and internet didn't really exist that much at the time it was new, but um really looking at why, why can't we use subscription concepts for services? And so, and I actually, ah way back then I had written a paper about the concept of managed legal services, the way you have HMOs in healthcare care and sort of that at the time was becoming a big thing.
00:04:44
Speaker
um And I wrote about, you know, would we have an analogous model in legal? And this again was written, i mean, almost 25 years ago. And so a long time ago, way before this idea um has become or evolved to what it is now.
00:04:57
Speaker
And yeah, so I launched it. i started out on my own and started to just get it going and talk to clients. I remember talking with colleagues of mine who worked at firms, some colleagues that I knew that were in-house ah Yes, people thought it was weird. They didn't understand it. They were what are you doing?
00:05:14
Speaker
Just do something else. This doesn't make sense.
Vision and Resilience in Entrepreneurship
00:05:17
Speaker
And, you know, so it was one of those things where, yes, it was a leap of faith. It was a it was a leap of belief in myself, ah but also a leap of faith in terms of believing in this model and being able to look around corners when others can't really see around the same corner.
00:05:31
Speaker
I think that's something that has been a common theme in a lot of my entrepreneurial experiences. pursuits and can tend to be a common theme with most founders is kind of being able to see that vision or look around the corners when others aren't really able to see that and being able to move move forward through a fog in spite of that.
00:05:49
Speaker
I think seeing around corners, maybe especially in relation to risk, is something that a lot of lawyers are really good at. Right. i Taking the leap, though, and like going all in on yourself ah is not something that either law school or the practice of law really like necessarily ingrains in you.
00:06:11
Speaker
and how how do you How do you think about that mindset, right? And like do you think it's a mindset that you' you've learned over time? Why do you think you've been able to embrace it? Talk to us a little more about that. I'm really curious.
00:06:22
Speaker
Yeah, thank you you. know, it's funny. I actually just wrote about this in a ah couple of recent issues ago of my venture legal newsletter on LinkedIn and covered this concept that I've kind of coined called the founder paradox.
00:06:33
Speaker
And I believe that a lot of founders will have this sort of yin-yang quality to them where there is this ability to Maybe perhaps like in this example, right? Make some calculated risks, look around corners, kind of be able to sort of see out ahead, if you look a few moves about ahead on the chessboard, but at the same time being able to also ah take a leap of faith, jump off the cliff while you're building the parachute, while you're flying down, right? That common analogy, but it's true.
00:07:00
Speaker
um When you're a founder, being able to sort of be comfortable with risk and ambiguity and be able to move through it. and And so I believe that a lot of founders have this sort of yin yang quality. And i've I certainly have seen that in myself.
00:07:12
Speaker
and But I also, and as I kind of touched on in my writing, and I'll expand on the theme in future writings as well about the founder paradox, but the I do believe it's very accessible for a lot of people. And I believe it's probably more accessible than most people think. I think that a lot of folks can become founders too, that they will perhaps recognize these qualities in themselves and and being more conscious of it might even help them nurture some of those qualities on ah either side of that yin-yang.
00:07:41
Speaker
They may
Can Anyone Be a Founder?
00:07:42
Speaker
not have certain qualities, but they, again, being conscious of it can nurture that. Some of us, I think, are hardwired certain ways where those qualities are a bit more innate, but then I do believe there's a nurture component, and and I believe that with AI and a lot of what's happening right now in our culture, ah the concept of becoming a founder is a lot more accessible to people, and so and I like to inspire people as well. So I hope that that piece did that, but that's what I would say on that topic.
00:08:07
Speaker
I agree. i mean, you know, I mean, there's two sort of theories, right? I mean, like one ai may lead to like a consolidation in certain parts of the the market, right? But on the other hand, you have all these tools at your fingertips and you're able to do so much more on your own, especially maybe as we enter a sort of like agentic landscape.
00:08:28
Speaker
Yeah. I don't know, that that the cost, like the startup cost is going to fall pretty dramatically off of a cliff. um Take us back to the early days of Zent Law. Like what were those days like of beginning to build the business? And was there an inflection point where you started to think to yourself like, okay, maybe this is really actually going to work?
Early Challenges and Breakthroughs at Zent Law
00:08:51
Speaker
Yes, there was. um But yeah, the early days were really rough, um as you can imagine. It was a lot of educating the marketplace, just out there pounding the pavement, literally just trying to get people to sort of see see this opportunity, see what I saw, see that this is there's a better way of doing things and there's an alternative out there that's reliable, cost effective and worth trying.
00:09:13
Speaker
And so, uh, yeah, the early days were rough, especially when you're launching a business in a sector that, you you're a little early to market or the market isn't quite there yet. And so, uh, I, I won't sugarcoat it. It was very rough at times. Um, and, uh, but then, yeah, you you hit this inflection point. I mean, I'm,
00:09:31
Speaker
you tend to kind of not give up that easily. So kind of, I knew that there was this opportunity there. And so you hit the inflection point and there was, there was an inflection point a couple of years in where just really started to kind of be able to build on the client base and one client led to another client to another client and so forth.
00:09:48
Speaker
And then it really starts to validate the model, but also really started to, build upon itself. And, and yeah, i mean, a couple of years in nowadays, that would be too long. But back then, it was not uncommon, because again, this was sort of a newer model for an traditionally wasn't, you know very receptive to change.
00:10:09
Speaker
What did that pushback look like? I'm actually i'm curious because i think I think it might be interesting for us to reflect on what pushback looked like back then. And maybe we look at that today and we're like, oh my God, that's par for the course. Everybody uses this nowadays, right?
00:10:25
Speaker
Yeah, great question. I mean, pushback. Yeah. i mean, what did it look like then? I mean, it looks like probably what you see nowadays in terms of pushback. I mean, there's sort of the resistance, the status quo. It's very hard to get people to unstick from the status quo. So back then it was really this, why is it better? Why should I try this? Why should I take this leap of faith? How do I know I can trust this?
00:10:45
Speaker
Yeah. Again, you know, it's a change from the status quo. So really trying to kind of deal with some of those objections. So a lot of sort of the objections around that and kind of dealing with that in in the the discovery process or the exploratory conversation process.
00:11:02
Speaker
ah sometimes kind of the outright just ghosting, you know, not like getting back, you know, wanting to have a meeting or any of that. so that that type of thing, typical, right? And and then, of course, ah other situations of of trying something and then being able to sort of say, hey, how can we kind of expand on this? or yeah and And working with the client in terms of how to make something work for their their needs. And so that also helped in some ways the business model to evolve a little bit too, because a lot of times I think with any company, any technology or services business or combo of both, ah taking feedback from your clients, taking feedback from your customers and looking at how can I morph or evolve or adjust this slightly to be able to meet their needs.
00:11:46
Speaker
And that feedback is always really
Client-Centric Service Adaptation
00:11:48
Speaker
important. So learning as well from client feedback is super important. I mean, legal is slightly more risk averse inherently, right? um How do you maintain the sort of conviction that you're going to be able to like sort of change hearts and minds and and really like convince folks to accept doing things in a different way than than they've historically done or that they're very comfortable with?
00:12:14
Speaker
Yeah, well, I think there are different ways to approach that. I mean, one, I mean, first of all, like as with any industry, and I believe legal and it even tech companies, legal tech companies that I advise or mentor not or invest in, I talk about this, that you can't really get people to change how they work necessarily. It's really important to sort of slot into their existing workflow. So you have to sort of figure out a way that whatever service or product you're delivering, it's it's porting into the way that they are already accustomed to working.
00:12:43
Speaker
So at least with Zetlaw and anecdotally, the services industry, they were already accustomed to working with outside counsel. They were already accustomed to bringing resources to the table to help them. What they were not accustomed to was the different model in which they could do that and a different delivery model and a deliverance different pricing models and so forth. So it was educating them on, you can get the same kind of output, you can get the same resourcing.
00:13:06
Speaker
but through a different different channel and different method and why that could be better and more effective. It's the same thing similarly with technology or legal tech, ah being able to sort of help educate that customer on you can get the same output, you can get to the same destination,
00:13:21
Speaker
ah perhaps maybe a little faster or maybe a little more effectively, or maybe with a few more data points or resources that you might need, whatever the tech is delivering, but asking them to fundamentally change how they work can be a bit challenging.
00:13:35
Speaker
and but But again, some of that has to has to be integrated. and so there's it's a it's a balance, I would say, right? I mean, for instance, even the idea around electronic signatures. I remember, I mean, some of us remember when that was, it was not a thing and it was this big deal in the legal industry around electronic signatures. Are they enforceable? Should we use them? Can we use the software? It's a safe, even SAS, going to SAS, know, all this talk about SAS and, and, and, you know, can we go to SAS? And so a lot of us that have lived through these evolutions in the legal industry, ah these were discussions that people were having. And,
00:14:10
Speaker
and For some of us that are technologists, it's kind of ridiculous because we're like, well, it's totally fine. like It shouldn't be an issue, but it was an issue. it was a real issue. And there were people writing white papers on it and everything.
00:14:22
Speaker
And so I think, again, going back to these tools aren't necessarily changing how people work. They were still going to be able to do the work, but just do it faster or more reliably or more conveniently.
00:14:35
Speaker
SAS makes things more convenient. It it made work. people It unshackled people from their offices. Electronic signatures, it kind of removed the conventional process of having to send physical documents back and forth and and all that. So again, it was not changing necessarily how they worked, but making it or enhancing it in such a way that it could be more effective effective or efficient.
00:14:58
Speaker
And I believe that's kind of some of the key messaging around some of the legal tech today is looking at how can you enhance ah the work that's being done. Super interesting. um I want to explore the sort of like journey that you've been on as a founder, ah because I've gotten to talk to some folks.
00:15:17
Speaker
i But, you know, i mean, a lot of people that we've had on have had slightly more traditional careers. Can you, you know, take us through, right, like how you handle when things don't go to plan, right? Or when you encounter setbacks or or sort of like inevitable periods of slow growth?
00:15:37
Speaker
And you've got people working for you, right? You've got your vision that you want to realize. You may have investors, right? I mean, there's a whole host of stakeholders that you're accountable to or trying to think about or or trying to manage. Like, how have you as a founder um been able to, right, sort of like find the wherewithal to lead through those really difficult moments?
00:16:01
Speaker
Yeah, thank you. it's It's a great question. And I mean, it's definitely something that's part of the founder journey. Step-up part of life, right? They're part of startups, they're part of business, they are part of life.
00:16:12
Speaker
That is the bottom line. And I would say first and foremost is getting really comfortable as a founder, business leader with the fact that they are going to happen and ah really totally bracing yourself. ah mentally, psychologically, for the fact that that's going to happen. And so what are you going to do when that happens?
00:16:28
Speaker
ah So I think that's the first step. and The second step is really ah powering through. i mean, setbacks cannot set you back. They have to be, you have to power through them. You have to figure out a way to work through them, either work around them, ah come up with an alternative Maybe path. Maybe it's a pivot. Maybe it's something else that needs to be done.
00:16:47
Speaker
Maybe it's streamlining operations. Maybe it's cutting costs. Maybe it's looking at another market to enter. There are a lot of different ways to solve some of these setbacks to depending on what the setback is.
00:16:57
Speaker
But I would say being nimble, being agile and being able to move through. a setback. ah And again, i believe these are sort of founder, founder, innate founder traits. I know that I have them and ah and many people do have them. And sometimes people don't realize they have them and until they're tested as well. And so once they're sort of tested in life or in business, then they realize that they actually had these traits all along or they cultivated them through that experience. But yes, I mean, I would say setbacks are never fun.
00:17:25
Speaker
ah They're never easy. But they are part of life, they're inevitable, and they're going to happen in any business. So it's really looking at how can you maneuver around them. And then also, ah there are times where sometimes you can sort of foresee a setback coming, you can sort of look around those corners and and get a sense of what might be coming out coming down on the horizon or what might be happening.
00:17:45
Speaker
There might be ripples in the in the pond that will give you kind of breadcrumbs around what those setbacks might be.
Anticipating Setbacks in Business
00:17:52
Speaker
And so being able to look at those clues and act upon them or take action early or preempt whatever is going on That can also be effective.
00:18:01
Speaker
I also think founders are better than most at dealing with uncertainty or or ambiguity. It's something that I've tried to, in my own life, right become a lot more comfortable with, or my own career become more comfortable with over time. I'm curious if there are habits or ways that you approach like keeping yourself grounded when there's a lot of uncertainty about what might happen. Maybe you don't have those ripples.
00:18:30
Speaker
Yeah, I know. yeah Well, and you're right, you know, in the legal industry, or like most professions, right, there is a lot of certainty, and people expect that degree of certainty. They yeah are often drawn to the professions, in fact, whether it's law or medicine, or science, or sometimes even engineering, being able to be drawn to some of these professions because of the fact that there are certain degrees of certainty, and certain things can be binary. And so being able to sort of have that buttoned up.
00:18:55
Speaker
And there's definitely a strong component of my personality where I like things orderly buttoned up, very organized. ah So there's a strong component of my personality, but then there's also another component of my personality where I am, I am very comfortable with the unknown and ambiguity and narrowing my way through it. And again, I think that's sort of the founder paradox that I've written about this idea of this yin and yang, being able to be comfortable in both um seeking out for me, it's seeking out, uh,
00:19:22
Speaker
order and logic and organization in my life and in systems and in things that I'm doing or working on, but also being comfortable with the uncertainty and ambiguity. And and and perhaps it's the yin and yang itself or the balance that keeps me grounded, I would say.
00:19:39
Speaker
i think some of that balance, like a lot of things in nature, is inherently... healthy. And so believe that perhaps that balance in my own thought process and how I approach the world ah perhaps is what keeps me grounded.
00:19:54
Speaker
ah And then just being a grounded, steady person is important. And i I believe that I am, and most founders probably are. But again, yeah we can also be passionate and headstrong and all of that. So there's there's that component too.
00:20:08
Speaker
Did you ever feel at any stage pressure to like go back to or to have a more traditional legal career? ah Yeah, i'm I'm just curious about that.
00:20:21
Speaker
Yeah, probably early on. I mean, I would say probably the the most stark example was early on when I was in law school because I had, again, been had sort of some entrepreneurial pursuits already. And then I was in law school and then hadn't pursued some of my larger entrepreneurial endeavors until while I was in law school and then beyond.
00:20:38
Speaker
But yeah, I do remember distinctly in law school, a lot of folks were just there are very much on a traditional path. And this is ah long time ago. So back then, there were really only ah a couple of paths. I mean, it was just, you go clerk for a judge, you work at a large firm and that's what you do. And then from there you move on.
00:20:54
Speaker
And even in-house practice way back when I was in law school, wasn't viewed as like a destination until much, much later on. So it was a very different mindset back then. And people um in school that I was with, you know, had a very kind of strict mindset.
00:21:09
Speaker
design on what they were going to be doing. i did not. I finished law school the first year with flying colors, scored really high and on my in my classes. And so I went to the dean and said, look, i'd I'd like to move to Los Angeles. I want to get into the music and entertainment industry. I want to work in that space and explore what's there for me.
00:21:26
Speaker
And because I had high grades, the dean was like, OK, we'll let you do independent studies. So I was already on my own path by the second year of law school, wanting to kind of do something a little different. And I remember friends in school at the time were like, what are you doing? And this makes no sense. like Why would you do this?
00:21:43
Speaker
And I was just like, well, I i want to do something different. So, so I did that. So I've i've been usually following my own path and creating my own path, uh, in spite of what others may be doing at the time.
00:21:56
Speaker
But yeah, it was it was unusual. It was a leap of faith. It was a bit scary at the time. And many of my classmates were absolutely not doing that at all. And so, so yeah. So, I mean, this it is something I've encountered ah from time to time throughout my life and career.
00:22:11
Speaker
Are there things that that law schools you think can do to encourage more diversity and sort of like outcomes, like career outcomes that might be more aligned to what folks actually want to be doing with their time or or maybe more aligned to like who people are and the problems they like to solve. And, and I guess along with that, you know, you've really helped usher in, or you've helped, yeah you've you've been able to watch legal ops really grow up too, right? Which I think is one great outlet for, for people who, you know, may have legal training and may be very good at talking to lawyers, but, but also want to be more operationally minded and program building, et cetera.
00:22:56
Speaker
Yeah. Talk, talk to us a little bit about, Advice you give to people around um pursuing slightly different career paths within the law. Yeah, exactly. Well, in law schools, I do believe. ah Yes, I mean, I kind of created or forced my own unique.
00:23:13
Speaker
approach to how I wanted to do this. And I i did not want to just sit in a classroom all day at the same law school campus. I wanted to go, I wanted to work full time, get experience in an industry I wanted to break into and continue to go to school, which I did. And I did at night on independent study. And then I took some other courses through a kind of a sister school.
00:23:33
Speaker
And ah so I was able to design this path. And had I not had that opportunity, at least by convincing the dean to allow me to do that, I might not have done it, but or found another way. But I do believe law schools can look at defining a few different paths. And now they're so much more accessible than there was when I was in law school. I mean, in terms of just the technology and virtual learning. I mean we didn't have any of that. So I believe there's a lot of opportunities to create some different pathways for people that want to be able to learn the law and um perhaps even go that path of, of I mean, I i did you know pass the bar and all that and practice too.
00:24:09
Speaker
So if people want to go that route, if they want to go into legal ops, they want to go into legal tech. I do believe that there are a lot of different opportunities for law schools to create some pathways for learning and ensuring that people are still, they're maintaining the integrity of the program while still giving people some alternate paths.
00:24:26
Speaker
And then to your second question about alternate career paths. Yeah, I mean, absolutely. I think the law is as a wonderful subject area to study. I think it's a great kind of so something to have in your back pocket, if you will, but it can augment so many different career paths. So you exactly if someone is operationally minded or they're more drawn to business and process and operations, then having a legal ops pathway or even a degree or certification program could be really good.
00:24:52
Speaker
um I believe eventually we might even have something that's legal tech, like a legal tech certification type of program. It may be a non-degree program, but something like
How Can Law Schools Foster Innovation?
00:25:01
Speaker
that. Of course, being able to integrate some of these other disciplines in the law school curriculum and being able to sort of produce people that are coming into the legal profession that have some familiarity with, of course, the legal tech as well as legal tech and AI, but also legal operations.
00:25:19
Speaker
And so being able to kind of bridge their entry into the market. And then lastly, I would say experience. I mean, for me, innately, because also perhaps I had early jobs and many work experiences, even leading up to law school, I was more inclined to develop experience. I wanted to get work experience. I want to be doing things.
00:25:38
Speaker
And And part of that's the entrepreneur in me. The other part is just wanting to be practical. And so I do believe law schools you know could could work on how they can integrate those opportunities to get real life experience for their students. So that way, when they enter the market, they're ready to go.
00:25:55
Speaker
You're also an investor in ah in a variety of legal tech companies. i mean, I've seen a trend of of ah GCs. I've had a few of them on the podcast who've gone off and and started their own ah tech companies or their own businesses.
00:26:09
Speaker
um what do you think of What do you think of that? And then I've got a few more questions for you on sort of like how you think about investing and and ah mentoring other founders. Yeah. Yeah. Yeah, yeah. Well, I was a legal tech founder as well. Founded some early legal tech companies. I've been around legal tech for a really long time. It's a space I've always been very bullish on and excited about and involved with. So, yes, I mean, mentoring legal tech founders, investing in legal tech founders. I've been a legal tech investor for almost 14 years.
00:26:39
Speaker
So have been around since the very early days of legal tech as we know it today. And it's an area that excites me. It's interesting. Obviously, I'm very involved with it. I write and speak on this topic a lot.
00:26:50
Speaker
ah But yeah, I mean, in terms of being an investor or like other folks that you mentioned on your on your show that have been general counsels and then gone off and started companies. Yeah, I mean, I think that's great. that'ss That's wonderful to be able to draw from the domain expertise and be able to create something that solves a real problem that perhaps they've been encountered or experienced. I think that's a great ah great great formula, basically, for success.
00:27:14
Speaker
What are some of the other signals that you look for if you're thinking about investing in a founder or or in an idea? Yeah, well, a couple things. I mean, first of all, the idea, because ideas can be a dime dozen. So it's really like what makes this idea unique, but also what makes it actionable? Is it actually solving a real problem? Is it solving a real problem today?
00:27:34
Speaker
ah Many of us who have been founders, and we've we've had our share of different types of mistakes. I know for me, some of the early legal tech companies, a couple of them were a little too early to the market or one in particular. And so sometimes it's going back and looking at, okay, is this a problem that needs to be solved? Is it, does it need to be solved today?
00:27:52
Speaker
Is it a problem at scale? Uh, in other words, is it a problem that's just going to solve for just a very small sub sub segment or very small group of people, but is, or is this something that's going to solve and, and is worth solving at scale, um, to sort of, uh,
00:28:07
Speaker
make a difference from in in terms of market opportunity and and investment opportunity. Of course, on the founder side, i look for sort of that founder archetype or many times in my case, sort of the founder paradox type of qualities.
00:28:20
Speaker
i sort of look for those types of things. I think they're important. It doesn't necessarily mean if you're missing everything, if you're not a good founder, not at all. As I said, i believe there can be a lot of nurture in some of those traits as well.
00:28:33
Speaker
But there are certain things that I sort of look for and in a founder that I'd like to see that hit the mark on some of those areas. And then, of course, that combined with domain expertise is always helpful or expertise in whatever their background is ah in terms of what they're contributing. So let's say if they're the CTO, then do they have the relevant background in AI and and so forth, for example.
00:28:56
Speaker
um So looking at that the relevant skill set, background, domain expertise, founder traits, as well as the idea itself. What are some of the ah problems that you think are most interesting to solve in legal right now?
00:29:10
Speaker
or Or what do you see out there you're like, that's a really, really compelling idea. ah I'm glad that someone's pursuing it. Or maybe you're pursuing it yourself. so Exactly.
00:29:21
Speaker
Yeah, maybe. Yeah, there are some really interesting ones out there. I've been really interested in kind of the whole compliance realm for a little while this year and kind of looking at just managing that beast. ah Compliance is is is a beast in most organizations. And it's one of these things that is kind of the not very fun back office. you know Somebody's doing this kind of work and and nobody's really able to put a lot of systems or process around it. So we've seen that on the legal ops front, but being able to look at it from a tech standpoint and make it accessible real time, leveraging AI and kind of helping to manage these compliance functions. And there are a lot of different compliance functions across different parts of an organization.
00:30:02
Speaker
um So that that compliance realm and tech that sort of addresses that is really interesting to me. um Technology that addresses area things around data and data privacy are really interesting to me as well.
00:30:15
Speaker
I believe privacy, security, and and all of that is deeply intertwined with legal, of course, as we know, and and also with compliance. And they're all kind of interrelated, interconnected. Yeah.
00:30:26
Speaker
With AI, um' obviously I'm a huge fan of AI and and everything, but there's also sort of the the privacy and security components. So that there's some interesting opportunities there around data and data being used in AI and what can be done around that. So those are interesting um areas that I'm kind of looking at too.
00:30:44
Speaker
And then lastly, I would say the predictive capabilities of AI also really excite me. So things that are drawing on the predictive capabilities of ai in a lot of different environments. I mean, of course, in legal tech, we have we have litigation. And so looking at and kind of tapping into or unleashing predictive capabilities in that setting, ah looking at other predictive capabilities in other areas to get in front of risk and de-risk certain ah things that could be happening in a corporate organization or public entity. Those are interesting to me as well.
00:31:18
Speaker
ah Let's talk a little bit about AI. i have i have a follow-up there. I'm curious. ah And I think I put a similar question maybe to David Cowan at one point. I don't love the question like, is AI overhyped or underhyped? But I do think it's interesting to to think about, is the impact going to be on legal and otherwise a lot greater than we might anticipate or be able to envision today, you know whatever, three years, five years down the road?
00:31:46
Speaker
Or i don't know is it is it not going to realize its sort of potential or or what we think it might be? ah Which of those camps do you do you fit in into and and why?
00:31:58
Speaker
Well, yeah, I fit into the, it's absolutely going to have a massive effect. yeah I fit into that i camp. I am a huge proponent of AI. I love the technology. i I'm a technologist myself. I was playing around with early versions of AI and machine learning and natural language processing in the earlier companies that I created in legal tech.
00:32:18
Speaker
And so it's been a space that I've been around for a long time and I enjoy it a lot. I strongly believe that we are going to see AI be an absolutely ubiquitous part of day-to-day law practice and how consumers, as well as sophisticated business clients, interact with legal services. ah I built a legal services model that was ahead of its time at the time, along with my contemporaries in the ALSP space.
00:32:45
Speaker
And I'm looking at now, okay, legal services 2.0, and that's obviously heavily AI driven. So um to me, i do believe that there we're going to see opportunities where AI can fully deliver upon certain things that we were using human capital to do before.
00:33:02
Speaker
I also believe that the lawyers, there's still absolutely a place for lawyers and and that lawyers will work hand in hand and side by side with AI and super agents and so forth. So yes, I believe it's going to become absolutely part of the fabric of business life as well as legal practice and law legal work.
AI's Role in the Future of Legal Practice
00:33:22
Speaker
And it it will be something that people will become accustomed to in the same way that they're accustomed to using the internet or tools, things like that. If you were to advise, and and you may be doing this right now, ah GCs, legal operations leaders, et cetera, on you know how do we create a culture that embraces AI?
00:33:48
Speaker
Where are places that we should be looking at it today? in in our you know day-to-day work? I mean, how do you answer those sorts of questions, right? When someone comes to you and says, Monica, I really want my team to start leveraging this, but but where do I get started?
00:34:04
Speaker
Yeah, great question, Tyler. And we do some of this through Law Innovation Agency, which I'm affiliated with as well. This is sort of the digital transformation agency kind of bringing AI in this consultancy to law law firms in terms of law firms, legal departments, public entity, government legal teams.
00:34:21
Speaker
And so really talking with them about this and and we're having these discussions real time, as you can imagine. ah But yeah, I mean, absolutely. I would say the first component and it goes back to some of these early legal ops principles, too, I've talked about and many of my colleagues in legal ops have talked about as well.
00:34:36
Speaker
for many years is so sort of that people process technology piece, but it does really start with the people. And it starts with the people in terms of, I would say, beginning with education and training, really educating folks on what AI can do for them, where it can be supportive, what what makes sense in their particular organization and workflow, and educating them on how to think about ai Again, i mean, I think a lot of folks have been afraid of AI completely taking their jobs and whatnot. and Yeah, I mean, we're going to see some of that in the larger economy. I believe in the at the macro level, we're going to definitely see ai take away certain levels of of of work um at lower ends just because that's what's going to happen. It's no different than, for instance, ATM machines replacing a certain degree of bank activity in banks, right? you you know it's Or it's no different than um certain other technologies that have that have come onto the scene in a lot of other consumer environments replacing
00:35:32
Speaker
certain jobs that people actually used to do.
Will AI Replace Lawyers?
00:35:35
Speaker
So I believe we're going to see some of that in law. But I also believe that there is still a tremendous opportunity for lawyers, paralegals, contracts managers, and legal ops professionals to interact with the technology and to, again, be these human experts working alongside these human or these kind of AI agents, if you will.
00:35:54
Speaker
and And that's going to be something that they're going to be doing. And the AI is essentially going to be almost like a coworker in many ways. And so being able to understand that, and understand that it's not a threat. It's sort of like your your coworker, your helpful kind of resource that you're using.
00:36:09
Speaker
and And also understanding the pitfalls around ah what to use, where do you use technology and how it can help. But yeah, there's a lot of education to start and then training. Monica, this has been a really interesting conversation. i like to ask all of my guests the same sort of set of of closing questions think it's fun to compare across across conversations.
00:36:32
Speaker
My first one for you is what your favorite part of your day-to-day work is these days. Oh, okay. i I would say favorite part of my work. I mean, it's probably something similar to what has always been my favorite part of my work, perhaps as an entrepreneur, which is that every day is a little different.
00:36:49
Speaker
I really like that. I like the i like the variety. i like that every day is a little bit different. And I really enjoy that. it's It's fun. It's interesting. It keeps me mentally engaged. And I really appreciate kind of that aspect of my day-to-day life. And then, of course, the other piece is is meeting great and interesting people like yourself, really getting connected. with people. I really enjoy meeting meeting people and I get to come across and and interact with so many different interesting people ah on ah on a weekly basis. And I really enjoy that as well.
00:37:19
Speaker
Flattery does work on podcast hosts, but you know you can do it at the start of the recording. and then No, this is a friendly shout. Do you have a professional pet peeve?
00:37:32
Speaker
ah Professional pet peeve. ah Well, let's see. I don't know. I mean, I'm i'm i'm pretty easygoing in some ways, I would say. I mean, ah lawyers, you know, we we tend not to like typos and all that, you know, and and writing errors, but that's that's a lawyer thing. ah I would say definitely professional pet peeve.
00:37:50
Speaker
I don't know. I mean, it might just, I'm a communicator by nature. So I like communication. I like the response. I like to engage. I would say perhaps ghosting is sort of a pet peeve of mine and in a professional setting, it's not like it happens a lot, but I always, personally, I always try to respond to messages. Even if they're DMs, people that I don't know, they've taken a minute to message me, I'll always try to respond where I can, even if it's something like, if I'm not going to have any interaction with them or,
00:38:16
Speaker
It doesn't make sense for paths to cross. I always try to kind of provide the courtesy of that. So yes, and I know everyone is busy. We're all busy. It's not possible to get to messages. But yeah, I think that getting a chance to respond is always really important or connect in some way. And I try to make make an opportunity or time to do that.
00:38:34
Speaker
So i I don't know. I don't I don't know if there's any other professional pet peeves I have. That's a good one. That's actually not one that I've heard before, I don't think on on this, you know, for as long as I've been asking that question.
00:38:47
Speaker
Is there a book that you would recommend to our listeners? And I mean, this can be something fun that you're reading right now, or it could be, you know, a book that's been really important to you in your career.
00:38:59
Speaker
ah yeah a book you'd recommend. Oh, gosh, I don't know. um i like there's a lot of different books that I enjoy. and I have been into sort audio books for some time as well. So kind of into those.
00:39:11
Speaker
I'm trying to think what would be a good one. There's so many good ones. I mean, ah umm trying to think what, I just finished Bill Gates' biography. I enjoyed that.
00:39:22
Speaker
um Yeah, that was kind of interesting. um i read Shoe Dog by Phil Knight about the founding of Nike. And again, like a lot of these founder type stories, I've always enjoyed ah the journey, the struggles, the ups and downs. Some of that came out of in Bill Gates' biography too. So I really enjoy these sort of stories of um how some of these companies were created and what's going on and in terms of what was happening at the time and what did they have to do and how they deal with the setbacks and how they get through it. And so I always i find those those human experience stories really interesting and fun.
00:39:56
Speaker
Shoe Dog's a good one. i really enjoyed that as well. Yeah. yeah Last question for you, Monica, my traditional closing question for guests. It's if you could look back on your days as a young lawyer just getting started, one thing that you know now that you wish that you'd known back then? That's a great question.
00:40:20
Speaker
i would say perhaps... perhaps Knowing that's going to be okay, that you're not going to follow a traditional path, but that's it's going to be okay. It's going to work out. And and it's just continue to move forward with your vision. ah so that Because there was a lot of sort of thought in my mind at the time about what I was doing and should I do that, should I not, what am I doing?
00:40:41
Speaker
So I would say that. I guess the other piece of it is, yeah, you know sort of any founder founder wisdom when you're building ah team or you're building businesses to really look at casting those roles right, making sure that you get the right people in the right roles. And that really makes a difference. And sometimes when you're early founder or young founder, you don't really know this. You're kind of doing, again, building the parachute as you fly down the cliff. you You're kind of learning some of these things as you go.
00:41:07
Speaker
and um and and people are probably the most complex um machines out there, right? I mean, in terms of understanding how people operate and how they think and how they work and what they're capable of.
00:41:18
Speaker
So ah I've always believed that many businesses, and even if you're in tech, there's a heavy component of of people that you need to really understand. And so um some of that is learning along the way. And and I would say, yeah a piece of founder wisdom might be ah really think hard about the people that you hire, the people you bring on.
00:41:37
Speaker
Or if you're co-founding a company, ah think hard about you're co-founding with. Do you sync with that person? Do you have complementary skills? you get along well? they somebody you like? Do you enjoy working with them? So really thinking about the people on your team or if you're co-founding with somebody, thinking about that too.
00:41:52
Speaker
ah Well, Monica, this has been a really engaging conversation. Thank you so much for joining me for this episode of The Abstract. Thank you, Tyler. It was awesome. I really enjoyed talking with you and I really appreciate you taking time to visit with me on the show.
00:42:06
Speaker
Absolutely. And to all of our listeners, thank you so much for tuning in and we hope to see you next time.