Brittany Green: Hey Ryan, how's it going today?

Ryan McKeen: Going well, Brittany, how are you?

Brittany Green: Can't complain, can't complain.

Ryan McKeen: Well, welcome to episode number whatever of the way podcast. I'm Ryan McKeen.

Brittany Green: And I'm Brittany Green.

Ryan McKeen: So Brittany, what is it that we're gonna talk about today?

Brittany Green: Well, we've got, finally usually, right, we're like five minutes beforehand, we come up with one topic. We actually came up with multiple today. So at least now we have some in the barrel for next time, but I'm excited for what we have to talk about today. ⁓ But did want to tease one of them, right? One of the topics that we're not maybe going to touch on as much today, but ⁓ we'll do it maybe next week.

Ryan McKeen: Yeah, so, know, one of the things I get asked a lot about is my UConn law class. ⁓ it's awesome. And I love teaching my legal entrepreneurship, my legal entrepreneur, I don't know why they gave me that word. ⁓ I

Brittany Green: I know, gotta find a better, this why we ⁓ are best era. We need very short, easy words to say. We are definitely not calling it anything with entrepreneurship in the name.

Ryan McKeen: You know, I had some other title for the class then it went through committee at Yukon and they were like, no, we like legal entrepreneurship. And I was like, you're me a word that I definitely can't spell will struggle to say. But OK, like you like I have to be professorial and level up. But I teach legal anyhow, regardless of how I spell or misspell it.

Brittany Green: You did.

Ryan McKeen: When I post about it on LinkedIn, I get a lot of people who are like, I wish I could take your class. I want to take your class. Well, I mean, I only teach at UConn in the fall to 18 students the hours of 1030 and 1230 on Wednesday mornings. UConn Law is a very beautiful campus. I think one of the most beautiful campuses of any law school in this country. but I in a small room with 18 people, right? So it sort of limits what it is that I can do. so I've taught it for two years and I'll be teaching it again in the fall, it'll be my third year. And so my first year, I assigned a bunch of books and I didn't know what I was doing. I some feedback and they're like, professor, we love your energy, we love your guests. They always love my guests more than they love me. And, but like too many books, right? So I'm like, okay, I'm going to scrap all the books and assign some and assign some I think I just assigned Will Gordara's Unreasonable Hospitality and the E-Myth Revisited, but I started generating a bunch of materials that were essentially in the books that I had read that I had wanted to assign to sort of condense it. I also used my plot AI to go out and record my lectures and the material and... with the idea of turning it into a actual textbook that I could use for my third year. So I created a bunch of stuff actually the materials I created served dual purpose because we use them for our consulting clients, for our community and for UConn, but being to pull it all together and I'm pulling it all together in a book that will come this summer or later spring. And as we celebrate release of the book, we're like, you know what, let's teach, right? ⁓ Suffolk is going to host us. ⁓ We're at some dates in July, almost confirmed. I haven't signed the contract just yet, I think reasonable assumption, July, a day of teaching in a ⁓ of, in a night seeing the Boston Red Sox. And yeah, so I mean, that is pretty exciting, but we're not going to talk about that. We're not talking about that. That was not the topic.

Brittany Green: No, no, no, although, you know, some of it kind of leans into a little bit of it. This is almost a subtopic of some of the things that law firm owners or lawyers that are looking to become law firm owners certainly need to be aware of, right? And to start thinking about. So yeah, so today, instead, we're going to focus on talking about AI tools law firms are actually using right now. And I mean, we get this conversation going in our community all the time.

Ryan McKeen: We really do. you know, I mean, look, everything in, you know, look, I've been around legal technology for 20 years, really, I've had a very big interest in it throughout my career. And, you know, it's really interesting to see adoption curves, right? And say, like, sort of like the first big adoption curve was sort of about 2010 to I'll say really about 2020, which was the idea that we could move our documents to the cloud off of servers, off of paper. And there was a lot of resistance with that, which was, is this unethical? What if it gets hacked? What if Google is reading my emails? And all these sorts of questions. And look, they're frankly great questions for lawyers to be asking. We have ethical obligations, and we have to understand them. But that whole curve was a very long period of time where it was clear to me in 2010 that the cloud was going to win for very reasons that look obvious, I think, in retrospect. But it took a very long time. And it wasn't really actually until 2020 when things get shut down during the pandemic that that really accelerated that and finished that life cycle. Otherwise, like people would still using a lot of paper and not and not using Zoom and not using Slack and technology like know, AI was very interesting right? Where ChatGPT really comes out in November of 22. I mean, like we're talking not even over three years ago, right? and people play with it and they're like, ⁓ my gosh, it can write things and it can do things, but still somewhat limited and illegal. have a huge conversation about hallucinations because lawyers don't know how to do it and no, chat, you can not just write a brief for you. But what I found more recently ⁓ that there is a real recognition this is way of the future. ⁓ actually the way of the present, right? things are changing and this technology is incredibly ⁓ and are rushing to ⁓ adopt They want AI, they want to use AI and like the from like, you know, Harvard Business Review does not lie, Brittany, like everybody is using AI. ⁓ Like the, you know, they are. the question, know, I for

Brittany Green: ⁓ yeah.

Ryan McKeen: lawyers and for legal a complicated question. It's one that we get asked a lot, ⁓ is like, what AI should I be using? How should I be using it? And, you know, where should I be using it? What are the uses of you know, one of things, mean, Brittany, in your consulting, in our channels, look, there are legal tech products. Like there was Legal Week last week in New York where I mean Harvey and Leguera and gosh, I mean there's probably like a Britney AI booth there. I mean like just, you know, just rampant amounts of companies in this space. You know, when you talk to firms and you see chat, like who do you see them using?

Brittany Green: For marketing though, you're talking about or ⁓ ⁓ legal work? Yeah, I mean, you know, I think most people are still using legal specific stuff, right? You know, you've got the big players that because they still they trust them, right? The Filevine, Clio, know, lead docket, status, right? You know, if you want to sort of call it case status.

Ryan McKeen: For everything. For...

Brittany Green: AI, obviously they have AI. Same with all the Filevine and Clio, they weren't ⁓ AI tools, but obviously we're talking about they all have their AI products, which are obviously the most important to them. So yeah, I mean, I feel like we're still seeing a lot of people that they want know what the legal specific AI tools are that are out there. Especially because they're the tools that are likely already implemented in some way in their firm, right? And so they want to make sure that they're going to be implementing tools that, you know, their people are already familiar with, you know, they've already got their system sort of in place with these types of tools. So yeah, so I mean, I'm seeing that and then of course, there's like on the opposite end, right of the people that are, you just want to start finding out like, how can I implement Claude, right? And things like those tools into our firms now, or can we?

Ryan McKeen: Yeah, and think it's interesting because there's a lot of conversations that are happening in legal. And one level, you have highly regulated firms who are, maybe they're handling security secrets or they're representing people who, big, big companies who have audit in different kinds of And so certainly like, those firms are drifting to very established tech products. And that makes sense. They have to. You cannot be a company like the Hartford or Travelers and vibe coding your way through life that's not going to really work. yeah, a lot of lawyers, the most popular products out there for lawyers certainly. you know, whether it's native AI into their, you know, existing case management software, it is, you co-counsel is very popular with ⁓ Westlaw. but in my conversations with lawyers, like ⁓ on, ⁓ the low, and I'm not, and I'm not talking about operational stuff. I'm not talking about, you know, marketing or all the other things we love to talk about at Pastera.

Brittany Green: Like actual legal work we're talking about.

Ryan McKeen: are using the LLMs are widely available, particularly at point, Gemini and Claude. They are buying pro plans or plans enterprise plans, and they are bypassing the legal of ecosphere a lot. you know, especially, and I about this, right? And I think about this because always interested in what the pioneers are doing, because the pioneers always, they things. They're out there and they're the ones who move into the neighborhood before it gentrifies. Where are people going? And those people are going straight to Clod Cod. They're straight to they are, they are bypassing these things because they are so cheap. They are so efficient and they're frankly able to push features ⁓ so faster than a company like even as large as Thompson Reuters, right? And yeah, are security trade-offs. and there are all sorts of maybe, maybe trade-offs that, that happen. And I think about and I think about like, look, Right now we're best era, we're four people we a lot of AI for various things. And ⁓ yeah, use Claude and we use Gemini ⁓ in to do a whole of things for us. But I was Connecticut trial firm and we're 40 people, right? And I'm running a legal team, ⁓ then you've got to about like how people are using it. There needs to be a reliability to it and a real audit log and it needs to be structured in a way, right? Because I know how to use things, but I can't assume that everybody on my team does. So I was at Connecticut trial firm right now, I would still be very into Eve or or Filevine AI.

Brittany Green: What are they sharing?

Ryan McKeen: because of what they have built out because of the ecosystem. And yeah, am I going to pay for that? 100%. But I think the trade off is worth it for a firm that has sort of scaled up, right? When we're sort of ragtag at best era, it's like, no, let's do this. And I think you see a lot of smaller firms now really that sort of ⁓ ⁓ my gosh, let's build this, let's build that. And so what it, what it's doing, I think is creating a real force multiplier for people. you know, lot of talk goes on and I think this is how is going to play out, which is like a barbell shaped, ⁓ curve in, in legal at the top, you have very big, very established things, right? And at the bottom, you also have, you also have people who are doing a whole bunch of things.

Brittany Green: Mm-hmm.

Ryan McKeen: in the middle is what gets squeezed. And I think, yeah, at the bottom right now, you if I'm starting a law firm right now, I am going all AI native. am getting SQL database, like air table or something like that. I am hooking up the clod. ⁓ I am, I going full in on, ⁓ on, on, on way. Right. And yeah, I would the outputs of. a team of probably 10 people, in various things, by, by some basic understanding of what Claude code can do. So I think it's like, I don't know. just think we're in this really interesting where there's interesting AI era where, where people are getting the are getting good and easy enough that it's, it's really

Brittany Green: Where, Mm-hmm.

Ryan McKeen: blurring a lot of lines and I think it's driving a lot of consumer choices. And I think you know, for AI specific companies, like they're not selling against, you know, it's not Filevine AI selling against Clio AI. It's really like they're competing with Gemini, Cloud and ChatGPT. ⁓

Brittany Green: Yeah, no, absolutely. And I think completely right about that, that squeezing in the middle. think we're going to start seeing a lot of law firm owners who either intentionally small and yes, use this technology to their advantage. and, and yeah, it's you know, get their success with the size that they prefer using these tools. then. if there are law firm owners that achieve that success and they kind of realize the only next sort of step potential growth pattern is going to have to be to get bigger, but it's going to need to ⁓ to bigger to a size that makes sense, So I'm thinking the people may have to scale their law firms, ⁓ if ⁓ they to to sort of that next level of success is... is probably going to have to be faster, right? that middle is squeezing out so that the competition's harder in that middle gray area now. So it'll be interesting to see how things shift in the because of that how we think about marketing these firms now going forward. Does the demand ever shift as well, right? Like, are we always going to have the same level of demand as we do now? You know, and how is that going to play into things? Are we going to find that, you know, somehow demand for more legal shifts in a way that middle doesn't get squeezed as much anymore? It's going to be very interesting. And it's again, it's since it's all happening so fast, like you said, it's not a ⁓ problem. It's a we're actively trying to figure all this out in the present. As going here. So yeah, it'll be interesting.

Ryan McKeen: yet. Yeah, you know, I think the demand for legal increases, I think society gets more complicated. And I also think allows you to unlock latent markets, maybe people you couldn't serve before, maybe who didn't have access before, because so much time in a law firm was taken up by trying to get information, trying to process information, and very time was spent on like, well, okay, what do I do with this information? Okay. And

Brittany Green: Yeah.

Ryan McKeen: you know, for first, those first parts of the equation to be automated and done well, you know, it leaves time to more. Right. And so I think lawyers are essentially faced with like sort of two choices, right. Which is you have these tools and are working still maybe a 40 hour week or are you you know what, ⁓ I can work hours a week and I can do what I could do in 40. And I'm cool with that. Right? I think that that is like, are choices that can be intentional with what is going on. you know, look, for me, I don't come for money. Sorry, mom and dad. But I don't come for money. And always the hardest thing in business for me was getting leverage. Right. It wasn't that I didn't have the idea or the drive to work hard or anything. It was like, I didn't have the money to get the things that I wanted or to get the people. And when you start playing with Claude code, you understand that it's a leveling technology. Suddenly, like I don't need a massive marketing department. need to understand how marketing works. I need to know what my goals are I can get. you know, agents who go out and analyze all of our data and say, here's what's performing best. Here's what's not performing. Here are some messages that you may want to, you know, tap into in your newsletters and social media. Right. And all of that is valuable insight that is available to me, like in an email in the morning without me doing anything. so think it's like, I think we're in an age where it's like, You know, people really have to think through this. They have to be intentional about their vision. They have to be very aware of what is going on, what is out there. I think I would be skeptical about signing long-term contracts into any legal AI. but I also think like there's a definite space for it. Like I was talking to a firm this morning and it was like, Hey, I ⁓ see Slack channel and your community and all that's going on in cloud code. ⁓ And yeah, it's, it's freaking amazing, but you know, I don't know if I should sign on with like a Cleo or a file vine. was like, no, you, really should, uh, because you need that single source of truth to pull your data to under, so, uh, the AI can understand your data. And, you know, that brings us back to like what we did after our first AI era event, which was, I'll let you tell the story, Brittany, uh, about. You know, we took Mary Lyon's talk from Filevine and said, yeah, you know what? We need to do better.

Brittany Green: Yeah, exactly. And that sort of almost brings it back full circle where we started of like what tools are people still using? And it is, it is the big ones, right? Clio and Filevine for that reason, because, and you just said it too, right? The reason, you know, this is a tools like Cloud Code level, the playing field is because of the ease of access to and what you can, you know, garner, you know, have it help you garner from it. But you said it yourself, like it was able to take data. from somewhere, right? But where was that data living? wasn't just in the ether, like, it was from a single source of truth. So yeah, after, AI era ⁓ we realized, you know, we had never really at best era, had a single source of truth, you know, we had our Google Docs, and we had our Tetra, and we had just things sort of living all over the place, we had our payments that happened in Stripe. But yeah, we realized we needed a central hub, a place where ⁓ we could finally create and store that impactful data that we knew would serve us long-term if were going to be intentional about the vision we had laid out in our growth that we were hoping for not in size our company, but in ⁓ revenue size. So yeah, of that said, we chose HubSpot as our single source of truth. made most sense for. You know, our company as more of a sales forward type of company, obviously, you know, we didn't need something legal specific. Clearly, we needed something that was more sales based. So HubSpot makes a lot of sense for us. And exactly what we, you know, connects to our cloud code and what we have it dig through constantly for us. And it's been great, right? Because, it did level that playing field where we knew based on our Our next best step was potentially going to have to be some sort of sales hire, right? Someone that could, you know, our hotspot for what it was really, you the purpose of it, which is to drive sales. None of us are great at that. We're also really busy, right? With the clients we have now and what we're currently doing in our roles at BestSara. But you know, but ⁓ we're small, we're We don't have the budget to bring on that necessary hire. So being able to have HubSpot invest in that as a tool and then invest in learning Cloud Code, that was our for us, which was we can now use Cloud Code to be our sales higher, at least for right now. And that's been huge for us. And I think that's what we'll be from a lot of firms who understand, yes, you need that one single source of truth. where you're keeping all of your legal data, your marketing data. And that's where you can bring in these adjacent tools like Cloud Code and Gemini and level up your playing field even more from it.

Ryan McKeen: Right. And so for those who don't understand what HubSpot is, like HubSpot is a CRM, but it's a very powerful We've used other CRMs for, we use Lead Docket for our law firm. ⁓ wouldn't be appropriate for what we were doing in personal injury. Like it just wouldn't in ⁓ Docket wouldn't be appropriate for what we're doing at Best Era. But know, what HubSpot does is it takes all of data. So we have a pretty sizable list of people who have engaged with us and are on our newsletter or our clients or in our community. And so it indexes all those people, gives us all their contacts, all that basic stuff. And it shows emails they've opened, what content that they've engaged in. If we have meetings with them now, those go right into the meetings. It shows deals, what's stalled, what's in process. It allows us to draft contracts. And it just does take payments. And so it really connects and it connects our marketing because it monitors all of our social accounts. It ⁓ us create landing pages ⁓ we can get some real deep insights into what is going on, what is working. We can get some, make some and it's all a very sort of structured way. And so when we it to Claude code, it really allows Claude code to go in and say, okay, no, no. This is the person you want to reach out to. This is their pain point. This is the message to send to them. This is how to follow up or, you know, Hey, we have an idea. What are some good, you know, here are three ideas that we have on something to do based upon the engagement and what we're doing. What is the ideas that are most likely to hit and how do I create a sequence for that? And then Claude can go in, look at our HubSpot data, create sequencing, create landing pages. and really do that. And I think it's so powerful when you combine those two things. I think if you're just in a sort of HubSpot world, and HubSpot has its Breeze AI, which is, it's okay. It's But I think what I'm seeing that's sort of interesting is you're seeing ⁓ announce really at Legal Week that they're really going after the enterprise market.

Brittany Green: Mm-hmm. It's okay.

Ryan McKeen: know, Filevine has been very big into the enterprise market and getting government agencies and people like that signed up. So I wonder if those companies aren't doing that because they're, they're feeling that, right? They're feeling the, ⁓ my gosh, like, you know, are smaller firms going to go away from us? You know, if we're in the, are we appealing to the middle? Do want to appeal to the top and not ⁓ in bottom? Right. And I that that's ⁓ the shift is going. So I think at sort of like a top level, yeah, you're living all in Clio or Thomson West or Supio or Eve or one of these products, AI. And a bottom level, you have access to almost their base product, right? ⁓ But interfacing with quad and you're interfacing with other things. And I think where... going to be very interesting to see, I think, maybe the on ⁓ those markets, I think ultimately driven by consumer demand. Because if they don't do this, there's going to be out there who's going to build a very basic file line. It's going to have contact ⁓ some document storage, and some things, some very basic a system and they're gonna say, hey, look, you can run cloud code in this and you can at it however it that you want. And that may be appealing to some folks. So, I think it's ⁓ a real interesting time for ⁓ legal technology, but think it's really in part driven by the consumer demand. And I'll say this, Brittany, I'm old enough to remember when... ⁓ law firms were like, you can't use an iPhone. Like you can't do that. It had to be Blackberry and it had to be on Blackberry server. So what was happening was lawyers would have Blackberries for their work phone and then they would have iPhones for their personal phone. initially it was like, ⁓ no, I really like this little iPhone QWERTY keyboard. And, or no, this Blackberry QWERTY keyboard. And then they... They eventually like the iPhone just way more. now like firms adopted to that and adopted to that. And I, and I think that it's like, yeah, if you're, if I'm using like breeze and hubspots AI, I'm like, this is kind of way boring compared to what Claude does.

Brittany Green: Right. Well, it's not even that it's boring. It's just that it's subpar. Like the information that is now is subpar. mean, and that's I think truly the only way that yeah, these, you know, the Clio's and the and the file vines and stuff. The only way they're going to get people ⁓ you know, us little guys here that are supplementing with with the standard LLMs. The only way they're going to get us back into fully only being in their products is

Ryan McKeen: Right.

Brittany Green: like improving those AI products essentially, you know, going to have some work cut out for them to compete something like that. And then like you said, especially for the price that people can pay for a to cloud or Gemini versus of course what the tech companies, you know, charge for their AI tools. That's going to be the difference maker for these companies if they're going to still be able to keep up with demand of the, yes, the consumers in that level that we're talking about. If want to keep them as just fully, you know, one place integrated customer, all of their products are what they use and they don't have to go anywhere else, one stop shop kind of thing. Yeah, they're just going to have to get better. you know, which I get it. hard. mean, it's hard to be good at multiple things, So, which is sort of why we are sort of seeing some of these other legal tools, right? That are, have become like really good at one specific thing, right? know, Supio, the EVEs where they're, they niche down into certain things, ⁓ know, speed with intake. So we've got all these different pieces where they've honed in and figured out the one really thing they can do well in the process. But now again, it's becoming harder because people still want that one single, one ring to rule them all. That's, ⁓ someone else was talking about in our Slack other day too. Like, is there a way have all of the that I am going to want in the process of running a firm and doing the legal work? Is there something that can do it all really, really well, you know?

Ryan McKeen: Right, right. And I think it's like to bring it full circle, like those tech companies are in the same sort of position, right? The middle gets squeezed. you know, the top is okay, the bottom is okay, but the middle is sort of like what gets squeezed. yeah, it's gonna be really interesting to see how it plays out. But yeah, I mean, it's a good time, I think, to be a consumer because you have...

Brittany Green: Mm-hmm.

Ryan McKeen: More options than ever. I, and I do think like that is like, I mean, I've played around with Zapier for like 10 years and tried to build things and inadequately built things. And it's like cloud code just like takes all that away and does it for you. and that's really, sort of, like a, ⁓ a real. Like watershed moment in all of, of legal tech, is. you know, no matter what, I know no firm that lived in one sandbox, right? They have Outlook, they have Workspace, they have QuickBooks, have And Code is kind of that operating system that can operate all over those things, right? And yeah, I mean, it'll also be interesting to see like, you know, companies like Clio and FileMent, do they like wall off more or do they open up more? ⁓

Brittany Green: Right.

Ryan McKeen: You know, and just ultimately look, it's going to be driven by consumers. you know, what do the consumers actually ⁓ or, know, they too will start losing a client base. So. ⁓

Brittany Green: Exactly. quickly, but I think this leads into another thing we're starting to see, which is ⁓ firms understanding the possible value ⁓ in team that's sort of solely dedicated to understanding tech, implementing tech, creating new tech or systems for firms. That doesn't have to be a legal background. So when we're seeing that with, you know, some of our clients are already starting to hire for that. I think that'll be a really interesting as well to pay to.

Ryan McKeen: Zero question. definite hire for us. ⁓ And would hire early because under, you know, like, look, this, ⁓ just so fast. And I do that there is a first mover because. I told you like the to the cloud was like over 10 years. You know, right now, like I think about it. And I like, if I really wanted to build, say, ⁓ like an automated estate planning firm. I mean, marketing operations, tech. I feel like I could get that done in like a weekend and maybe I'm not the best and maybe I'm not the highest level, but I'm going to, I'm going to assume maybe I, I'm going to assume I, I do know estate planning very well. Right. So I have, I have the expertise because I think that that does matter. Like, I think I could, you know, really scale. could really run a lean firm quickly, you know, do PPC research. get up a website that delivers, figure out pricing points, automate the documents, and do these things. And I think that you're going to see people who move in very small firms very, very quickly. And I think that they will, and I'm not talking like five years from now, I'm talking like this year, start gobbling up market share because they can deliver a very good product at a very reasonable price with not a ton of their time.

Brittany Green: Yeah, absolutely. think things are changing fast. We'll see how goes.

Ryan McKeen: So, Brittany, what is it that you are watching, listening to?

Brittany Green: Let's see, so I finished House of Guinness. I know I mentioned I had started watching that last time we talked. Such a good show. I cannot wait for season two. I don't know when it's coming out or I it will be because they left me on a huge cliffhanger. So really excited for that. And it fit right in because yesterday was St. Patrick's Day. So it got me really into the Irish spirit. Noah Cahn, of course, released newest single last Friday too, so. listening to that one.

Ryan McKeen: Yeah, I mean, you know, last year for me it was Wu Tang was my big concert. This year, Noah Khan's my big concert and I've been going through his back catalog and I have really been enjoying Busyhead by Noah Khan and listening to that. think it's, you know, it's in contrast with his more recent stuff. This is a little bit more upbeat, but very good.

Brittany Green: Well, and I like it because you say upbeat. Meanwhile, the actual themes of what he's singing about are still very, ⁓ but I hear, yeah, it's the banjo. It's banjo and the guitar. It gives it that upbeat. Yeah. Yes. Yes. Yes.

Ryan McKeen: Correct, no, correct, no, the lyric, no, but... It's a little bit more poppy. Like, it's not happy, but it's more... It's poppier. Like, that's it. So, well, thank you, Brittany.

Brittany Green: Thank you, we'll see you next time.