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You're Fine: AI, Anxiety, and the Future of Law Firms

54m 39s

You're Fine: AI, Anxiety, and the Future of Law Firms

Ari Kaplan, principal of Ari Kaplan Advisors, joins the Mostly Legal Podcast to share his unconventional journey from lawyer to legal industry analyst. He practiced law for nearly nine years, starting as a managing editor of his law school newspaper, which led to writing opportunities with his first firm’s partner. His passion for writing about technology, particularly the internet, grew alongside his legal career, eventually leading to paid freelance work and a decision to leave law practice despite skepticism from colleagues. His wife’s support was pivotal, and he has since built a 20-year career as a market researcher and analyst, studying both corporate legal departments and law firms, and producing over 70 reports. During the pandemic, he created the Virtual Lunch, an informal Zoom networking event that began with a small group and evolved into a weekly tradition with over 1,350 episodes, featuring guest speakers and tech demos. The community has also driven charitable efforts, raising nearly $13,000 for the Apostles House in Newark. Ari emphasizes his humility regarding AI expertise, noting that his knowledge is practical rather than exceptional, and highlights the importance of mentorship and community throughout his career, reflecting a sitcom-like life filled with serendipity and meaningful connections.

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(upbeat music) - Welcome to the Mostly Legal Podcast. I'm Amanda Coplas, Chief Operating Officer Ashuffield Lomin and Wilson, a midsize law firm based in Central Florida. - And I'm Rob Joiner, Senior Vice President of the Assistant Development Center Base. - So Rob, today we're speaking with Ari Kaplan, who is the principal of Ari Kaplan Advisors, and he is the person to know in the legal text space. He is the speaker and he leads a virtual lunch. - She's just all over the place. - I was actually on that virtual lunch, but the more exciting thing about this episode is I got a new uncle. - Okay, you are ridiculous. I think I just disassociated during that entire section. - Forget it, let's just jump in. - All right, today we are joined by Ari Kaplan, and Ari, I'll let you tell us a little bit about your background, but before I do, I need to just warn Rob, like Ari is a professional, and you really need to be on your best behavior today. Like, notion and against, A game, like, you know, he's the real deal. - We've done 10 minutes of pre-call. - All right, where we gonna go? - So just to make you feel comfortable, I'm very palsy with my nephew, who can be mischievous, and but not as mischievous as Uncle Ari, and we'll go out to dinner and we'll sit next to each other and wanna do something mischievous, and I joke that we're the only members of the best behavior club. So now you get to be a third member of our best behavior club, because of the mischievous. - Just to send the tele. - If I get to call you Uncle Ari for the rest of the hour. (laughing) - The shenanigans begin already. - All right guys. - Okay, but jump into your background, Ari. - Sure. - Yeah, thanks so much for having me. I've seen many of these, and I feel lucky to be part of now this community. So I'm an analyst that covers the legal industry, which is a kind of a made up title. I've practiced for nearly nine years and have been on my own for, it'll be 20 years in a few weeks, and so after price. So when I practiced, I published nearly 125 articles over the nine years that I practiced, and so I felt like I was sort of a writer and a lawyer walking this road simultaneously, and at some point I just started walking on the writer road. I would joke with people that I was a lawyer on the side, which obviously wasn't possible, but I would write in the middle of the night, I mean, I'm feeling like Rob, who's way more successful than I am as a writer, as a painter, and as an artist can appreciate that. And so I started out, thinking I would write freelance, like articles about technology, 'cause I had been writing for all these different technology magazines about the internet. I practiced between 1997 and 2006, and so when I first started writing, I was writing about technology and very cool stuff. And in the early days, you could write for a lot of really impressive places, 'cause they just weren't a lot of people writing about the intersection of law and technology. So I wrote for Wired, and for, I had a column in E-Week magazine, and I was writing the cover story for computer years, and all these other stuff, it was really a very, and then of course I wrote a lot about legal tech, and then I started ghost writing when I went on my own, which because I have a sort of a unique look at what legal tech and legal services are doing with technology, at least back then, 20 years ago. And that kind of led me into doing market research. I was doing a lot of white papers, and someone approached me and said, would you consider interviewing a whole group of in-house counsel, and then putting that together into a report? And I thought, sure, except nobody is going to take my call. Like there is not one person that's going to take my call. And actually, this is actually, I should give credit to Debbie Caldwell, who's now a platform, but she was at FIOS at the time, and she said, I think people will talk to you, and we'd like to structure it in a way that would make you feel comfortable, but we're confident that this is going to work. And to her credit, as many people as we wanted to, we're considering taking my call. I put that together into my first report, which was for FIOS, and I've done over 70 of those now. So I sort of think of myself as a market researcher, but really I've sort of grown into this role as an analyst, because I'm studying both the corporate side and the law firm side. So the buyers and the sellers, and in fact, do a lot of research on the technology companies, and also do research both here in the US and abroad. So I occupy this wonderfully unique and fun position that gives me a lot of opportunity to do exciting things and talk to really, really extraordinary individuals. - Well, you're like the person to know, right? Like if somebody knows you, they're a big deal. Like we're big deals just being used in the room. - You're so rich. - You're rich. (laughing) - You're rich. - She stands alone in this office by himself, you. I'm the guy to know, no matter. - Our status was immediately elevated the second you said yes for us. Okay, so tell us a little bit. You've a background in journalism though, also in addition to going to law school, right? And so you started kind of working for this newsletter and it kind of snowballed from there, right? When you were at the law firm. - Actually, I don't really have a background in journalism. - So Rob got the note wrong, okay, great. - Well, I'll tell you the story. I'm fine with all of my history. I think it's, you know, because when I think of a background in journalism, I think of someone extraordinary like Bob Embrojie or David Hargan, you know. - I thought you had a journalism, your degree, your undergrad was in journalism. - Nope, my undergraduate degree is, I did a double major in political science and economics. - You just doubled down on being told you were wrong. I don't understand what you did. (laughing) - We all have a place. - You guys are crazy. - Essentially what happened was when I was in law school, a friend of mine was the editor in chief of our law school's newspaper. And he said, listen, we need somebody to lay out the newspaper. - Oh, that's right, okay. - And I said, what does that mean? He said, it means you need to learn how to use page maker at the time. - Oh, wow. - I think people use that anymore. - Yeah. - And that actually is a paying job. The school pays for that and also includes a substantial scholarship. And I thought, I'm your guy. That's it, I'm the guy. And so I taught myself how to use page maker. And it was great, 'cause I could listen to music. There was nobody in the office. I would lay out this paper and I was called the Managing Editor. And it was great. And every once in a while I would write something. Maybe I remember once one of the civil procedure professors had a baby and I wrote a profile of him as a new dad teaching. And I think that no like hard hitting extraordinary news. But it gave me some practice, lucky for me, the person who interviewed me for my first job saw that I was the Managing Editor of the newspaper and asked me about it in the interview. And I said, well, I'm the Managing Editor and I do some writing and I showed him the clips that I had. I wasn't like, oh no, I'm this extraordinary journalist. And part of the reason he hired me was 'cause he wrote a column for a publication. And when I started on day one, he said, hey, I write this column, which means we write this column. And to his credit, he gave me a co-bialign on every single article that we wrote. And so by the end of my first year of practice, I probably had 10 bialigned pieces. And that was really what I found passionate. I was really excited. And then at some point, I think this was 1997, 1988. I said, we've been writing about-- 'cause at the time I was doing international trade and customs work. And he said, we've been writing about the importation of Chinese wood. And that's really-- Or what would constitute a feather that was important that you could put on a blouse. And I said, but I think we should write about the internet. The internet seems like a thing. And I understand that this is our practice, but this is very cool. A lot of cool stuff is happening. It was really funny. He was like, you know what? I'm going to keep writing about my thing, because he was extremely successful, the industry standard. And he said, but if you can get your work done, bill your time, do our article. You can write about as much as you want. And I'd support you. And he did. And that really set the foundation for what I've been doing for actually much more of my career than practicing the law. Writing about the internet. Start-- Well, started, right. So Ari, just going to that point. So you get your bachelor's degree in journalism, you get your JD, then you end up working in law for writing. Writing on the side. When did you make that actual jump? Like, what did you even say to that partner if they were still around when you made that jump? It's a great question. So I had been practicing for nearly nine years at this point. And I talked to my wife, and I said, listen, I think that I could do this. I think I could make a career out of this, because over the years, what had happened was originally I was writing and obviously not being paid. Most lawyers write for visibility to highlight their expertise, which is totally appropriate. But at some point, I started getting paid. You know, people would say this article pays $2,000. or $3,000 or $500. or something like that. It was actually, it's funny because it sort of comes full circle. The very first publication that ever offered to pay me was a website called Prairie Law. And Prairie Law was started by Kevin O'Keefe of Lex Blogfame. And everybody knows Kevin O'Keefe. He's sort of a really an all-star in legal and a wonderful mentor of mine, a wonderful supporter of my career. But the very first publication that ever offered to pay me was this website called Prairie Law. And because I had pitched them an article about something, maybe FTC standards on something. And they said, "What are you thinking of in terms of compensation?" And I was like, "Compensation." And I was just like, "I don't know, 20 bucks." Like I couldn't even think of like, "What's the right number to be paid for something I would do for nothing?" And they said, "We pay people $250." And I said, "$250" sounds like a nice, great. That's great. And then that became a thing. And I was like, "Oh, maybe I get paid for stuff." And it really, once you start writing for mainstream publications or I had this column, when I had this column, they brought me into the studio that took headshots because they put a headshot with my column. It was very exciting. And so I've been doing this for really awhile then for many years, I guess, and getting paid. And it could have been tens of. I'm trying to think of like, "What the number ended up turning out?" It wasn't a livable wage, but it was a substantial kind of bonus that was helpful and fun. And I said to my wife, I was like, "I think I can do this." And my wife, it's funny because I said to other people and they were like, "You're crazy." You should stay being a lawyer and trying to go the full distance. And I liked the law. I'm still very close to my mentor who is my mentor in the early 2000s. We have such a close relationship that my mentor, who was extraordinary, was recently honored and asked me to introduce her at this ceremony honoring her leadership and accomplishments. And I felt very proud. And I think it spoke volumes about our relationship and what an extraordinary mentor she was and continues to be that I had worked for 20 years. And still she felt like I should introduce her. And so the firm was great. I was lucky to get really, really good experience. You know, for a big firm, I took to positions. I had argued motions in court. I had read teams of people. It was lucky work, which is sort of a theme that I use a lot in my career. And. But anyway, I asked all these people. They said, "That's a stupid idea. Do not leave the firm. Do not leave the law." And my wife to her credit said, "I think you should do what you think is going to make you happy and trust that you'll figure it out." And she was right. And she. I mean, she, several years before that, she had started her own law firm when our son was born. And 23 years later, that's still a thriving firm. And she's, you know, she's in herself at just a incredibly gifted lawyer. I don't think she would have said, "Ari, start your own firm." But she thought, "Ari, you do you." And. But this is like, you would be greater writing. We did talk about a lot of ideas. And we still today, joke, even to this day, it comes up. She's like, "Member, you're going to get an office on whatever avenue." And she's like, "That would have been a terrible idea." And I'm like, "You're right." And I have heard that message. I heard it 20 years ago. I heard it now. I know that that would have been a bad idea. But so far, so good. You know, it's like, we have a little bit of a fun banter. You can imagine. It's like a sitcom. My life is a little like a sitcom. Can I ask you, so during COVID, you shifted to your lunch. And I can't remember what I think it's called, your lunch bunter or something. Can you tell us a little bit about that? "Ari's lunch bunter." It's called the "Current Lunch." Oh, God. So you know what's funny about that? It's so funny that I started this. It's funny that I started this because there's a connection to the pandemic. So when my niece and nephew were homeschool, they were all on remote school. They were going to be 13. So you can go back and they were like, I don't know what that is. First grade or something. They were very young. And they had to do school on Zoom. And they just wanted to have a call with Uncle Ari. They wanted to do Zoom call with Uncle Ari. Zoom call with Uncle Ari. And I was like, great. So my sister-in-law sets it up. We have the Zoom call with Uncle Ari. And my nephew and I have this call. And as soon as he gets on, he immediately puts me in like a breakout room. But it's only the two of us on this call. So he like relegates me to the breakout room. And then he goes, that's lunch or something. And I am sitting in this breakout room doing nothing. And I'm like, you know what? He's now the president of the Best Behavior Club because that was awesome. I cannot believe the mischief in this guy. It was so funny. I was like, this guy and I, we have a connection. It was very cute. Anyway, so what happened was on Monday March 16, 2020, we were all, you know, going to be home. And so on the weekend, I think it was Sunday. I posted something to LinkedIn. And I just said, hey, looks like we're going to be home for a while. Like, I think I wrote two weeks actually. And that was me optimistically thinking, this is going to be two weeks and we're back. But as long as you're home, I said, I'm going to open up a Zoom link. And if you want to join, great. I'll see you, you know, give you a little networking in the middle of the day. I don't know who's going to pop on. But if you want, great. And I got a zillion kind of comments, direct messages and likes and stuff. Like, this is a great idea. We need this. People like, we need this in Italy. And we need this here, you know, various connections that I had, you know, in different places. And so I pop on the next day. And there are, I think there were 10 people, like all people I was really happy to see, not that they're ever people. I'm not happy to see. But I was like, oh my gosh, I can't believe so and so from Amsterdam or so and so in the UK or so and so. And I was just like, this is so cool. Like, I'm so happy to chat with you. How is it going? We were like sharing information. Like, what's going on by you? And can you go out? And what are you doing? And you know, in the early days, we'd start, we'd talk about mask. Where are you getting masks? Or how are you organizing your calls? Or, you know, do you go on camera? If you go on camera, what should the lighting be? You know, it's like, all of you remember all of these interesting things. And then at some point, someone suggested, I'm pretty sure it was my colleague, Sharing Clark, who said, we should have a guest. And I was like, is that a statement about how boring this is or how chaotic this random call is? And she's like, no, but I think that would be fun. And I'm pretty sure our first guest was Jordan Furlong. And I asked Jordan if he would come on and chat with us. And he did. And we got a great crowd. And I was like, wow, guest. And so it ended up being that we would have these random people would show up. And then on Fridays, we'd have a guest. And then we started. And Rob, of course, honored us. In the early days, I think of your art career. And showed us, Rob was amazing. Showed us what he was doing, what he was working on. It was really, really exciting for us and very, very cool. And then we'd have a day for people to show a demo. We'd have technology companies show a demo. And it has lasted. I, it has lasted for over six years now. What's it actually on? It's not the lunch. It's called the virtual lunch. It's called the, and I, and I changed the signs, you know, like every month I have a different sign. And it says virtual lunch on it. We have a theme. And so I have since moved it to Fridays only. So after the sixth anniversary, which just took place. And we're on something like episode 1350 something or something like that. I, I moved it to Fridays. But I, I would like to say that for the different milestones, you know, the virtual lunch community is a wonderful group of people. And they would want to have a celebration of the hundredth episode, a 200th episode, the thousandth episode, or something like that. And so for the six, and so then I realized, you know, people are really interested in this. Maybe I could use this for good somehow. And for the sixth, and I've done this over the years. But for the sixth anniversary, I made a $600 donation. And I reached out to a bunch of companies in the, in the space. And I said, oh, you know, would you consider matching my donation as a sponsorship of the virtual lunch? And it ended up raising almost $13,000. Wow. It was really very cool. There were so many companies from all over the world who were, you know, just like immediately like, yes, great. Whatever you need. And that money, I should say, went directly to a place called the Apostles House, which is a, I serve on the board of trustees proudly of this organization that empowers homeless women and children in Newark, New Jersey. And so that donation wasn't to me. It went directly to the Apostles House. And as all those donations do. And I've tried to use the virtual lunch for that purpose in a lot of ways to just let people know about important causes or issues. And just, you know, giving smaller organizations in need, visibility beyond their local region can be very helpful for them. We'd like to take a moment to thank our sponsor, Cinterbase, legal practice and management software designed to deliver optimal efficiency, profitability, and business growth for your mid-size law firm. Learn more about how Cinterbase helps you practice, manage, and grow your law firm with modern technology at Cinterbase.com. That's awesome. I enjoy participating. I enjoy following along with that. It's incredible to keep anything going for six years, especially with an audience with events, but then to turn it into something where you're getting back to really neat. So all those launches you heard from tons of people, you understood trends around masks and all this fun stuff during COVID. Now you're an expert on AI, right? And you're hearing tons about AI. I am just such an expert on AI. I have, I've used, I've used Claude and I'm the same expert everybody else's. I just have the benefit of getting to learn from and speak to incredibly smart people. I will tell you that I had the really incredible career privilege of interviewing the General Council of Anthropic yesterday. Oh. Or an event I participated in with Lexus Nexus. They had an AI symposium with the Harvard Club and Jeff Bliche, the General Council of Anthropic, agreed to be the keynote in our fireside chat and I was lucky to be asked to do the interview with him. It was just incredible, like a wonderful conversation and to be able to sit side by side with someone of that caliber, it was really an honor. Rob is an early clonid doctor. A doctor. Yeah, my question totally changes already. What were like the top three things that you learned during that session? I think the biggest takeaway was the element of humanity, right? This is an individual, his background is so remarkable. He was the US ambassador to Australia. He had clerked for Chief Justice Renquist. He had served as a partner in several firms. He's been the General Council of different companies. All of the boxes of extraordinary and legal in society, he has certainly checked. He really spoke very eloquently about the importance of balance, but the importance of character and not losing that in the face of technology. He also talked a lot about the value of making kind of calculated mistakes when you're trying to drive innovation. And I know, man, do you know this? It's running a law firm. There's a really important element as we evolve in our profession of recognizing that although we are heavily reliant on past practice and precedent and managing risk and being really conservative and it comes to certain types of decisions, it's also important to reach as a profession, reach in our careers. And he really spoke about those points about managing his team, which has grown substantially since he joined the company and obviously never a dull moment in an organization like that and in an industry like that. And you're right, though, I have been lucky to do several different types of research looking at AI since over the last couple of years, but obviously very recently. It's a focus. You can't really get away from it. I started including questions about it in the last couple of years, but now I'm producing research that specifically focuses on use cases or value propositions or transformation. So, are you in your research when you put the terms AI and ROI together? Where does it lead you? It's a great question and I was lucky to do a report that came out probably a five or six weeks ago with LaGora. And LaGora asked me to interview their clients in 14 countries and ask not only about what they think of LaGora and incidentally they love LaGora. Their clients love them and they would recommend them. There were all those different metrics that I captured that are in the report, but also to try to understand the impact of usage. And you could extrapolate. I was asking specifically clients of one company, but to their credit what they were trying to do was also explain what this does industry-wide. And so we were really trying to look at this from the impact on revenue, the impact on work quality and then the overall impact on the greater business of law. What does that transformation look like? And so we asked questions like what does your response time or what does the quality of your work look like and people said, oh, you know, 94% said they can respond faster to their clients and to stakeholders within the organization. When I asked about work quality, one of the key things that comes out all the time is that gosh, these tools help me identify things I might not have thought of or might not have seen and that's especially true of people at different levels. And so over 70% said that LaGora identifies issues that otherwise would have been missed. And then of course I asked about what's the impact on the business of law? What does this look like from a transformational standpoint? And almost two thirds I think talked about this idea of having a transformation of impact on their use of AI and what that looks like from an infrastructure standpoint of their firms. So when you're talking about like from the associate attorney level, like where are they really seeing the biggest gains? So you know, the benefits, we know the benefits, but where are attorneys really seeing the biggest gains? So in my research, what I tried to do was to give something of a roadmap to help firms take data that they already have, financial data, business development data, recruiting data, peer reviews of different things. And in fact, yesterday at this AI symposium that I participated in, I also was lucky to moderate a panel discussion with a CFO of a big firm, the chairman of a big firm, and the general counsel of a large company. And my panel discussion was about reimagining legal economics. You know, what does the law firm of the future look like? What is the relationship between corporate legal departments and law firms? And right now there is a tremendous benefit towards efficiency. And efficiency isn't the best metric just being able to do something more quickly or getting an answer more quickly. Isn't really the, in isolation, what we're looking for. In many ways, what you're trying to figure out is what is the result of greater efficiency. And for a number of people that I spoke with, the result is that they can now maybe take work they wouldn't have been able to take. Maybe they can scale their organization in a way that's more effective. Maybe there's work they would have declined because they didn't have the people that didn't have the resources. They couldn't kind of handle the timeframe. But now, in this case, Laura, they were able to look across a spectrum of a huge volume of documents, get answers quickly, and make a proposal that would be beneficial to the client and also allow the firm to operate maybe on a leaner team, which also then gives the experience to people they might not have gotten. So I was very lucky because my mentor, when I was practicing, would at any moment, I would say, you know what, I've been reviewing these documents for a long time. I know the material. Could I take the next position or could I defend in the next position? And she would always say, great. And she'd immediately pull out her account and she'd be like, Tuesday in Toledo, there's a year-it book, your flight. And she, I'm telling you, that was exactly how it went. And then I'd say, you know, I took the deposition, I reviewed the documents, could I argue the motion? And she'd be like, there's a motion on a month from now, on a Wednesday, a New York Supreme you're on. And you don't get that. That's just not often how it works. It certainly at a junior level, I mean, I mean, I was maybe a junior almost mid-level, but I was pretty young and inexperienced. And she knew that she's always say, if you don't take the lead, the view never changes. And so she was, she lived that. And I think that she continues to do that now. And I think that that helps. And that's the benefit. Although you're seeing different benefits at different levels. I spoke to people at different levels, and I do different kinds of reports for different groups. And so the perspectives change. For junior people, there's a question of judgment, as you know, there's a question of trust. And as a result, the tools may not be as beneficial to someone who can't judge the results as well as someone who's more senior. You know, they say that, "Hey, I work best for people who already know the answer." And because of that, there's a distinction in who gets the benefit. Lots of people talked about mid-levels being in a sweet spot or senior associates. And I would agree, however, I think there's a great opportunity for junior people who are willing to spend some more time and upskill. You know, I love the stories about Rob painting. off hours and squeezing it in, I used to call that stealing time. In between, my children, I'm super proud of them. They're adults now, but when they were little, it was like life of the cat in the hat, where my wife is running back from court and I'm trying to get to a game and I have to drop my daughter off and then I was like, I have to finish something, I have a deadline, but the deadline is actually fungible because it's not really work deadline, it's this deadline. You want to get it all done and you have this juggling act and you're balancing on a ball with a rake and a cup and a fish and the whole thing, I think that if junior professionals are willing to take on a little, add a little of that manic to their life, they will find opportunities that their peers don't because they will prove more quickly that they can use their judgment to make decisions about these tools because we're not going back. The tools are here and they're only getting better as we continue to use them. The question is, are we getting better at using them? And that's where we are in the moment. And how does that reframe what the associate does and how many associates are hired for firms too? I mean, I think the stat last year was, the associate hiring was down 15% on Wednesday. This just came up this morning only because I'm speaking at the corporate legal operations consortium conference next week. And I'm moderating a panel, someone from a corporation and someone from a law firm, both very focused on pricing and this conversation about what does that mean? If the funny part of that question was that the corporate person was very eager to hear from the law firm person because they're all kind of in it together. That was the thing that came out of my panel yesterday, which was the leader of the law firm and the leader of the law department, both all stars, really well recognized, just exceptional leaders in their space, very well known, were commenting about trying to get to equilibrium. The law firms obviously are trying to figure this out. They're investing tremendous amounts of time and capital in getting to a point where they can use these tools in a way that doesn't disrupts but doesn't catastrophically change the business model. And the law departments recognize that they need the law firms. They're the person that's going to validate and is going to provide ultimate guidance. So they don't want to get rid of them. They're just trying to figure out what that rebalancing looks like. And we've had disruptive forces in legal before, whether it's external situations like the pandemic or the financial crisis or technology like this that is transforming things. You can go all the way back to the use of computers and email and cloud, et cetera. But we've had this before, my sense is that legal research. Well, that came up, obviously. It's a really interesting point. I mean, I will say that in the conversation yesterday, there was a really interesting discussion about having legal research that's of the caliber of Lexus Nexus, because that was the sponsor of the event. But of that caliber that you can inherently rely on because it's designed to be the end point. And using your AI tools that relies on trusted and gated and verifiable information in the same way that humans will need to build trust and validate everything that they're using these tools for, but the tools are getting substantially better. So we need to grow with the ability to use it. I think that's a really important point that's come out of a lot of my work. Can I shift gears a minute and ask you about the mid-sized law firm report that you did? Yep. And so that while AI was a portion of that, it also touched on a lot of other trends. We talked, you know, for that report as well. So some of the things you talked about was like some of the strategic challenges that mid-sized firms are having. Can you talk about some of that you found for that report? Yeah. So I've been doing this report for several years. And I have also been lucky to just directly engage with mid-sized firms in particular through my work with the ALA, speaking to ALA chapters. I've been lucky to be invited to speak it over a dozen chapters and several conferences. And I've been doing this report for several years. Last year's report, I did it with our friends at Affinity Consulting, of course, at I Manage and at Sure Point. I know you know them all. And I think what's important about the trends and the strategies there is that you're seeing an interesting realignment of the competitive advantage that technology provides to mid-sized firms. So in the same way that I mentioned, you can take a massive volume of documents. You can review it quickly and firms could all of a sudden provide work that they otherwise would have turned down or wouldn't have had the scale or the individuals in the manpower to deal with. And in fact, on the manpower point, I spoke to a leader in a corporation recently and they said we used to use law firms for manpower. We don't need their manpower as much anymore, but we need their judgment far more. And that was a really interesting description of the shift that's taking place. And so for mid-sized firms, I think what has come out of the report year after year is that if firms can replace fear of emerging technology or digital transformation, if they could be more methodical about leadership shifts, about succession planning, if they could really identify new markets, if they could use their financial data more effectively to determine what's truly profitable, then they can compete in ways they may not have been able to even just a few years ago. And those themes really resonate. I hope to do the research again this year and to try to verify some of those conclusions. But I'm actually so honored when I get to talk to the mid-sized law firm leaders that I speak to because they're kind of operating in this really interesting universe where they have fewer resources than their larger peers, but the same caliber of talent, the same objectives and the same clients. That's right, that's right. And so they are seeing, many of them are seeing that there's the technology gives them a promise they didn't have before. And so the landscapes are shifting. Of course, the landscapes are shifting from behind them as well. Like smaller entities are able to compete in ways they weren't able to. So you're seeing this come from the back and in the front, just from a side standpoint. And I think that that's a really important area to be mindful of. Well, tech is really what's helping us get our hands around financial data, right? Because for so long, and I've been in firms now for 21 years, and so we've always collected the same data. You just haven't been able to get it out and analyze it. And you're restricted to what your financial system reporting system can give you. If you want to run this by this, if that report isn't native, if you can't pay to have it built, the data isn't coming out. If you don't have a way to interact or to chat with your data for lack of a better term, if you don't have that ability, you can't make decisions based off of it. So one of the benefits we are saying is technology allowing us to actually get our hands around it without having to buy these huge power BI products and things like our native platforms are doing this now. And I think that's really going to help taking advantage of data from our side. You're also seeing people able to teach themselves how to do certain things and how to deliver certain data much more quickly because the tools are more user friendly, but people realize now that there are ways to teach themselves. I'm a little bit of a fix it guy. So I've disassembled my washing machine, my refrigerator, my dryer, my printer. I call somebody for that. My dad was incredibly handy, and so thankfully he passed that down to me. I was joke that when I was a kid, my dad used to always make me hold the flashlight and it used to drive me crazy and be like, I need to hold the flashlight and I hold the flashlight, stand there forever. And he'd be like, I need to focus on this, focus on the red wire, focus on the copper piping or whatever. And sometimes he'd have me do it outside when there was light already. And so as a teenager, it took me a long time to figure this out, but as a teenager I was like, I'm out of here, dad. I'm not holding the light for you on the garden. And I realized this adult, he never needed the light. He just wanted me to learn and pay attention to what he was doing and I did and I'm grateful to him every day. And so I think that people realize, if my washing machine breaks, my wife's like, oh, there's an OE error. And I'm like, go on to you to, OE error means there's a valve. It's like one of three things. I tried the things that are easy. It's never the easy things and I'm like all right I looked at it says you got to take off the top and you know remove this and she's like what do you? How are you? I was like there's a guy he an or a woman they said this is how you fix it And I was like I'm just gonna follow them. It's junk anyway if I can't fix it so we're good and Rob is your washer has a OZ air are you a lying a new one or be buying a new one? Let me tell you something Amanda last night the kids were taking a shower trying to and the little stopper broke and so The to go from back to shower. Yeah, yes, so so I Took it all apart Took a picture of it gave it to a clawed clawed actually diagrammed it for me Then I figured out the piece was actually broken so I ordered new parts and I'll be fixing it this weekend of Anna I am on video he's here that oh, I will be on video now Yes, Amanda I will tell you all about it as I'm fasting and as I'm thinking about a couple of time right Oh my god That's it actually a great a great point because I had to take off like a move a television You know off of off the wall or something and there's it's screwed on with a special kind of screw and I was like I've never seen this before I guess I didn't put the TV on the first place And I took a picture of it. I put into chat you tell you what is this and what tool do you need to remove this? And it's like oh, it's a security hex something you need this tool and I was like can you find me the link on Amazon Got me the link Crazy thing and like this Rob said that you order a part comes in two seconds Then you just I was like I took it off, you know, it was uh, I even looked for the part. It gave me a link You know anyways, I'm incredibly handy and fix everything around my house, so But I'm a youtuber said I guess I have never used claw maybe I'll do that next time, but Hey, are you I have so many directions I could go with it The conversation I I like to think of you know at the end of the year the dictionary comes out with The word of the year right the Webster comes out with the word of the year In legal tech if you if you were to you jump to the end of the year Around legal tech and AI. What do you think the word of the theme is gonna be for 2026? Wow You say I just use it You know, it's it's so it's so interesting that you said that because I always tell my kids to try to Enjoy the adventure You know, especially as they've gotten older. I'm like, you know, I know you're concerned about this or you're thinking about that But imagine this all is it like one big adventure like Then how exciting is it what is that what does that feel like what does that look like? I feel like there's something about that in legal this year, but If I would have picked a word I don't want to use like something uh so common like transformative, but I feel like Uh Pivotal, you know, I feel like this is the this is the crossover year and This is when you're you're not even just seeing Use cases of stuff you're seeing people very thoughtfully consider what They could do to If their business was disrupted in a really material way What would that be and why don't we do it to ourselves and actually the general council was on my panel Yes, what he said we try to disrupt ourselves before Anyone else does in her in that in her company's business and My one of the very first articles I wrote to try to develop a portfolio of technology related Pieces was a book review of Clay chrischenson's the innovator's dilemma which is the foundational book about disruption in in You know technological disruption and disruption in business and so Who just meaningful to me that she brought that up and so my my sense is that this this is sort of the pivotal year Law firms are always so far behind so it would make complete sense to me that we were three to four years behind The rollout of generative AI. We're actually starting to do something with it So that that makes sense to me. Well, but I I think that law firms shouldn't give themselves such a bad rap in the sense that it it's not like There are giant enter like a huge number of giant enterprises have completely transformed how they work because of AI They've bought a tool they've rolled that tool out enterprise-wide and then Some people are really productive at that tool I think that people should be realistic about where they are in the journey and they're not So far behind it feel like I feel lucky in my work to conduct I don't know hundreds of interviews every year about this and so For example, I'll do an annual I do an annual general council report with FTI and relativity and then every Once in a while like a group of general counsel will invite me to speak To their groups about you know, they have a local groups of GCs and The question will always come up like how are we doing you know? Where are we relative and I'm like you're fine You're actually be the word of the year because there's so much you're fine Yeah, like there's so much fear we're all like for mid-sized firms and us Rob We're all freaking out like are we gonna be behind are we picking the right tool are we Using governance correctly. Are we getting the right guard rails in place? It's are we are we are we are we so it's like okay You're fine my word is governance I mean that's that's what I've thought about But to your point Amanda. I mean I woke up first thing this morning. I woke up check my email first email is so-and-so invests and An AI first law firm not a legal tech company law firm and into your point. It's it coming at us also fast And it is hard to keep up with but for the most part you're fine Here just be fine. Maybe that's the the title of the episode already Kaplan you're fine Well, I also think that there are fundamental aspects of what we do that matter More than the technology we're using right what is your what is how are you approaching client service? Can you do that better? Can you be more responsive? Can you be more thoughtful? Can you be more proactive in the business of your client Rather than hey, we applied a tool and saved us an hour I think that if you were somehow so deeply embedded in the business of your client and you could provide them with A level of guidance that speaks directly to how they could succeed you would Give yourself a competitive advantage far more than any piece of technology now if you could leverage a great piece of technology to do that even better That's the kind of the combination that people are really hoping for so when they're thinking of are we this are we that the first question should be How good are we at what people expect us to be doing? Could technology make us better what would delight our clients that kind of conversation isn't happening as much as Should we license this should we buy this which tool is going to make us faster or something and people kind of Miss the point we are in a service business and In in a service business you want to serve and I think that that element tends to get lost But when you speak to leaders who are really attuned to what that ultimate objective is they really start to map out a strategy that keeps that Front and center and I think that's a really and I try to so I host a breakfast series called the legal tech mafia and I do it in Typically every other month in New York City and typically hosted at a large law firm and but I When I travel I'll do it. I just recently did it in Dallas. I'll Do one and I think San Francisco Chicago do one in London and Amsterdam wherever I'm happened to be going I try to do a breakfast and try to bring people together and anyone is invited You know if you're you're a law firm your corporation you're with a vendor you're a consultant. I'm I'm Want all voices everyone is is heard and I think that's kind of how community is built and We talk about these issues like you know what does client service look like and and you know what what's what's great technology? What what have you been using? Let's share some ideas kind of like hey where did you find a mask? You know it goes back to that it's sort of a theme in terms of what I've been trying to do It's you know sort of like now I'm the guy holding the flashlight and I think that that's an important part of you know my career. It's fun now. So now everybody's I looked at the time Amanda I know we can do a five-part series on this yes everybody sitting in their car waiting to get out and going into the office Yes, yes, they are we're at that point in the episode. So, yeah, it's a lot of transition. Yeah, so thank you, Ari We fit we finished all of our episodes with a little section we called Pitch your passion and you briefly mentioned an organization earlier And you could talk about that a little bit more or really anything else your passion in about four years Well Yeah, so I service a member of the Board of Trustees for an organization called the Apostles House, and I think that it's really important to be thoughtful about how we can empower others. And I think that's a real theme of my work. You know, I'm trying to empower people with data, with information, with perspectives, with community, and I think it's consistent through all the things that I do, just in terms of my work, and got involved with the Apostles House, actually, because my daughter and I, my daughter, is now almost 21, but when she was six, I asked her, I'd read about somebody in Tucson, Arizona, who had this campaign of asking his neighbors if they would leave a single can of food on their front steps, and his promise to them was, if you leave a can of food, I'll pick it up, and I'll deliver to a food bank. And kind of made it easy for people to do good by doing something very simple, but in the aggregate turns out to be incredible. And so I asked some of my neighbors as an experiment, and my daughter and I were home on a Sunday morning, and I said, "Hey, you want to go outside? I asked some people to leave some cans of food on their front steps. I'm curious to see if they left it. Do you want to come with me?" She was adorable, and she's like, "Yeah, yeah, yeah, great." And she runs upstairs, and she gets like a baseball cap. She's always wear these fun baseball caps, and she got a notepad and a pencil. And I was like, "What's the notepad and the pencil for?" I said, "I want to write down what we get, you know, like to keep inventory." And so we started walking around our neighborhood, and sure enough, we found a can. A little bunch of cans of people in front of our house, and I thought, "This is great. My daughter's writing down, you know, vegetables." She's like, "Daddy, how do you write? What is green? Is green two ease?" And we're like, "Right, green beans and carrots." And it was like a really fun experiment. We started doing spelling and counting and writing. I didn't really have all of a sudden, I had this great way of teaching my daughter. And we did this for many years, and we would collect over time, we'd collected thousands and thousands of cans. Like every single week, like the virtual lunch, just like every just chipping away at something, and just seeing what happens. And I think your career is like that, frankly. And so anyway, I'm a point because I'm sort of looking out on the street. And we'd collected that, you know, my daughter was like, I guess at like seven or eight, we were invited to speak at a school. So here's this eight-year-old telling other four-year-olds, you know, what she doing with cans. And just the whole thing was very good. And at some point we got to the point where she started driving us to deliver the cans, because we'd bring it to a food bank, and you know, just sort of became full circle. I couldn't be proud of her. And of course, became a family affair. Obviously, my wife was very involved, my son became very involved, and we were sort of the canned people. And you know, that's how we would deliver to the apostles' house, and then over time, they had given us an award for all of the work that we had done, and then I got involved in the leadership, and I just think that in a lot of the things I do, you know, I do a, I host a run at almost all the legal conference. Actually, every legal conference I go to, I kind of put together a run, or I participate in the run, or lead the run, depending on what the conference allows me to do, or asks me to do. And I always tell people, I make a donation to lung cancer research in memory of a buddy of mine who was young man and got lung cancer and never smoked, and I always make a donation to lung cancer research. And it's funny, because the lung cancer foundation, it's called lung cancer foundation of America, you know, has reached out to me, like, who are you telling about this? We just got all these donations, and I was like, amazing, I love it. People want to run, and I always say to them, and I'm maybe I'll leave you with this, but every time we start, it's usually like a beautiful morning, sometimes it's not, but it's a morning we're there. And I always say that, you know, no matter what, we're just so lucky to be together. Like, we're out here, it's beautiful, we're capable of running or walking, we should be grateful. And it's like a great way to start that, you know, activity, and I think that I try to keep that in mind for everything I do. That's beautiful. Well, you don't even have a journalism degree. Yeah. Uncle Ari, thanks for joining us today. Thank you so much. You guys are great. That was a lot of fun. Thank you. Thanks for listening to this episode of the Mosielegal podcast. If you like what you heard, make sure you like and subscribe so you don't miss a single episode. Stay tuned as we uncover more behind-the-scenes stories of law firms with the best minds in the business. And Rob. Thanks.

Podcast Summary

Key Points:

  1. Ari Kaplan is an analyst covering the legal industry, with nearly nine years of legal practice and 20 years running his own advisory firm, Ari Kaplan Advisors.
  2. His career began with writing about law and technology, including columns for publications like Wired and E-Week, which evolved into market research and over 70 reports for clients like FIOS.
  3. He transitioned from law practice to full-time writing and research after encouragement from his wife, despite warnings from colleagues, and has maintained strong ties to his legal mentors.
  4. During COVID-19, he launched the "Virtual Lunch," a Zoom-based networking event that started with 10 people and grew to over 1,350 episodes, featuring guests, demos, and a global community.
  5. The Virtual Lunch has been used for philanthropy, raising nearly $13,000 for the Apostles House, a Newark-based organization supporting homeless women and children.
  6. Ari describes himself as an "expert" on AI only in the sense that he uses tools like Claude, acknowledging the widespread, evolving nature of AI expertise in the legal field.

Summary:

Ari Kaplan, principal of Ari Kaplan Advisors, joins the Mostly Legal Podcast to share his unconventional journey from lawyer to legal industry analyst. He practiced law for nearly nine years, starting as a managing editor of his law school newspaper, which led to writing opportunities with his first firm’s partner. His passion for writing about technology, particularly the internet, grew alongside his legal career, eventually leading to paid freelance work and a decision to leave law practice despite skepticism from colleagues.

His wife’s support was pivotal, and he has since built a 20-year career as a market researcher and analyst, studying both corporate legal departments and law firms, and producing over 70 reports. During the pandemic, he created the Virtual Lunch, an informal Zoom networking event that began with a small group and evolved into a weekly tradition with over 1,350 episodes, featuring guest speakers and tech demos. The community has also driven charitable efforts, raising nearly $13,000 for the Apostles House in Newark.

Ari emphasizes his humility regarding AI expertise, noting that his knowledge is practical rather than exceptional, and highlights the importance of mentorship and community throughout his career, reflecting a sitcom-like life filled with serendipity and meaningful connections.

FAQs

Ari Kaplan is the principal of Ari Kaplan Advisors, an analyst covering the legal industry. He practiced law for nearly nine years and has been on his own for almost 20 years.

He has a double major in political science and economics, and a JD. He started writing about law and technology during his legal practice, which led to a career in market research and analysis.

He began writing articles, including paid pieces, while practicing. With his wife's support, he left the firm to pursue writing and research full-time, eventually becoming a market researcher and analyst.

The Virtual Lunch is a recurring Zoom networking event started by Ari Kaplan during the COVID-19 pandemic. It features guests, demos, and discussions, and has run for over six years with thousands of episodes.

Ari Kaplan posted on LinkedIn in March 2020, inviting people to join a Zoom call for networking during lockdown. It grew from 10 attendees to a regular event with guests and demos.

For its sixth anniversary, Ari Kaplan raised nearly $13,000 through donations and sponsorships, which went directly to the Apostles House, a nonprofit empowering homeless women and children in Newark, New Jersey.

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