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Overruled by Data is the podcast for law firms looking to accelerate their data journey without all the pain points.
Hosted by Tom Baldwin and brought to you by Entegrata, each episode shares real-world stories from law firm leaders who’ve tackled the tough stuff—getting data from all the right places, navigating the AI hype, and scaling operations in a way that doesn’t leave you with a mountain of tech debt.
If you're in a leadership role at a law firm, this show offers valuable insights from those who've been there, sharing what works and what to avoid on your data-driven journey.
[00:00:00] Tim Fox: There's so many legal tech solutions out there that are built not with the attorneys in mind or not with adoption in mind.
[00:00:06] Tim Fox: There's a lot of things out there that are just built to say, "Hey, we have this, it does XYZ," but then you ask the question, "Well, is anybody using One of our big focuses on the innovation side at Ogletree is, okay, well, what are our usage stats? Are people actually using this? Because if not let's do something else. Let's pivot, let's move it, or let's cancel that, and, let's see where we can better direct, our resources.
[00:00:39] Tom Baldwin: Today's guest has one of the most distinctive career arcs in legal technology. Tim went from mailman to litigator to AI co-founder, to now the person setting the data and AI strategy from one of the largest labor and employment law firms in the country.
[00:00:57] Tom Baldwin: Tim Fox is the first ever chief and data AI officer at Ogletree Deakins, a firm with more than 1,100 lawyers and 60 offices across the globe. He didn't arrive there in the traditional path that we see today. As I mentioned, he was a mailman, then went into the technology sector, spent seven years practicing as a litigator, then co-founded LegalMation, and now he's at Ogletree since 2020 leading practice intelligence and analytics, and in 2026, just this year, was elevated to the C-suite to lead, the firm's entire AI and data division.
[00:01:30] Tom Baldwin: He also teaches at USC Gould School of Law, my alma mater, and serves on the California Judicial Council's IT Advisory Committee. Today, we'll dig into what he's learned, what's changed, and where he sees data and AI headed next. Tim Fox, welcome to Overruled by Data.
[00:01:48] Tim Fox: Yeah, thank you. Very happy to be here.
[00:01:50] Tom Baldwin: So we mentioned, Tim, your path is a little unique, from being a mailman to getting your computer science degree, working in the Fortune 500, going to law school, being a litigator, founding an AI company, which is pretty cool, and now in the C-suite. What's that through line look like for you?
[00:02:07] Tim Fox: Yeah, right? I wish I could go back in time 30 years ago and plan this whole thing out, but it it really has been much more, I think for me, a focus on technology and then figuring out where to, leverage technology as whatever, career path I was on. So, you know, I was a mailman back in the early 2000s, and I think there's a lot of parallels there because, in the mail back then, email was just getting started and mail volume was way down and people were talking about how this was the end of the profession.
[00:02:36] Tim Fox: And now here we are 26 years later, now the current career that I'm in is having similar conversations, right? About AI coming in and this is the end of the profession. As should be obvious by the fact that we still all get mail, at least for now, it was not the end of that profession and hopefully it's not going to be the end of the legal profession.
[00:02:53] Tim Fox: If anything, I haven't checked stats, but I don't think there's been a significant decrease in the number of mail carriers. As we'll hopefully talk about, there's been no decrease in the number of attorneys over the past few years. We keep churning out more and more from law schools and elsewhere.
[00:03:07] Tom Baldwin: You've written about the moment in 2016 when your managing partner came back from Harvard,panicking about AI, then that panic became Legalmation. What'd you learn from building something from scratch that you couldn't have learned any other way?
[00:03:19] Tim Fox: Uh, I don't think I wanna go back and do a startup again. I'd say that's the, one of the main takeaways there. There's a ton that you learn when you have to build something from scratch, and it was also part of transition, right?
[00:03:29] Tim Fox: Going from litigating every day to building software product is a huge transition, and I think at the time, I don't think any of us understood what we were undertaking then. As an attorney, you feel like you can do anything, right? You become an expert on something for six, 12 months, and you go to trial, and then you learn something new.
[00:03:47] Tim Fox: We approached it, I think, a lot like that, as we were all litigators at the time, that we can learn this, If we've done these multi-million, hundred million dollar trials,of course, we can launch a software company.
[00:03:56] Tim Fox: Back then, AI really wasn't very good. This was using you know, really what I would consider crude methodologies now to get where we are. And we still managed to build, an industry leading product and award-winning product then with the technology that we had.
[00:04:10] Tim Fox: One of the big takeaways that I had from that was thatreally anything is possible. If you have the right people, if you have the right team, if you have the right mindset, you can succeed in areas that are difficult and challenging. That has really helped shape my focus hereat Ogletree and how we've grown is to say, "Okay, well, let's get the right team together and let's get the right tech stack together and then, we can really build."
[00:04:30] Tim Fox: I think it's also, you know, One of the takeaways from that was just learning a lot about how software development works.
[00:04:37] Tim Fox: Being able to speak that language of, here's how you actually build solutions and here's how you build tools, I think that there's a big gap in the current legal environment.
[00:04:45] Tim Fox: Generative AI to a certain extent is making that gap bigger. Now you can go into Claude and you can build a proof of concept. You can build an app in a weekend. You can say, "This is fantastic. I want to deploy this firm-wide." and you can't, right? The, the, the building that proof of concept is stage one, and then being able to scale that to an enterprise-wide application that meets all of your security standards, actually reliable and that somebody can support and all of that, is an order of magnitude more difficult than it is to just go out and vibe code something.
[00:05:10] Tim Fox: and so I think a lot of folks who haven't gone through that sort of boot camp of having to build your own product, deploy it, secure it, scale it, think that it's just as easy as, you know, going in and typing and vibe coding something and then there you go. I think it's great to have that ability to vibe code and build tools because it's great for proof of concepting, it's great for ideation, but you have to be realistic and say, "Okay, what I'm building here is just for me.
[00:05:32] Tim Fox: That ability to build, develop software and understand how that works and speak that language is something that has really assisted me in my career and differentiates what we're able to do at the firm than a lot of other firms who don't necessarily have that background and expertise.
[00:05:45] Tom Baldwin: We could probably spend an entire hour talking about the merits of vibe coding, versus the path you went down of learning the hard way what it's like to build software. Having been a CIO and CKO for decades, I thought I knew a lot about technology. is very different running and building a software product than it is being in tech.
[00:06:06] Tom Baldwin: and so I appreciate that perspective quite a bit.
[00:06:09] Tom Baldwin: There's always this pivot, I think, in everyone's journey where data goes from something you just sort of think of in the background to it becoming a, a really strategic asset. Was there a moment where it just sort of clicked that like, okay, we need to harness our data for more than just a report that sits in someone's inbox, but is actually a competitive advantage?
[00:06:28] Tim Fox: so My legal tech career has been largely data-focused, right? At LegalNation, what we were doing, we were extracting data, and then what we were enabling you to do was automate what you could do with that data. But the key piece of that was the data extraction. And At Ogletree, it's similar.
[00:06:42] Tim Fox: When I joined the firm, you know, this was pre-generative AI, this was back in, in 2020, there was a lot of focus on data extraction. What more can we do with the data that we have? And that hasn't necessarily changed. It's gotten actually a lot easier with generative AI because now I don't need a team of, you know, five people to go build me this extraction algorithm and locate the data.
[00:07:02] Tim Fox: We can do that much easier. But still the data isa key piece for everything, and I think we're gonna see more and more emphasis on data and,data-enabled law firms. That's what a lot of people are talking about. There's a couple of examples I can think of where it's really clicked,
[00:07:16] Tim Fox: and a lot of that has to do not so much with me because I, I understand the data, I get the data, but it's when there's that connection where what I think is important in data is what my attorneys also think is important in data. One of the things that we did early on atOgletree was we built a settlement extractor.
[00:07:31] Tim Fox: It extracted 30-plus data points from class action settlement agreements to create a repository of that data, because class action settlement agreements are generally publicly available. It's complicated to locate the data, and you have to extract the data, and then you have to make that data accessible.
[00:07:45] Tim Fox: Each one of those has its own challenges, but the biggest one I would say now, generative AI has simplified the first two, making it easier to locate and extract, but the third is, is making it accessible. How do you make that data accessible to attorneys who aren't data-focused people?
[00:07:58] Tim Fox: Because it's easy to make data accessible to people who understand SQL queries, right? Who can query a database, can go out there and do all of that. You don't have to teach them anything. But for an attorney, you need to make sure that data is intuitive and that it's accessible, and they can answer their questions and even know what questions to ask.
[00:08:15] Tim Fox: As an example, we queried I think 20,000 plus settlement agreements. I think we extracted whatever that is as far as data points, several hundred thousand data points, and then putting those together in a way that our attorney could go in and look up that data. That was somewhat of an eye-opener both for them, but also for us. It's not enough for us to just have the data. If that data is not being used, if it's not being made accessible, it wasn't worth our effort.
[00:08:38] Tim Fox: There's so many legal tech solutions out there that are built not with the attorneys in mind or not with adoption in mind.
[00:08:45] Tim Fox: There's a lot of things out there that are just built to say, "Hey, we have this, it does XYZ," but then you ask the question, "Well, is anybody using it?" Right? a lot of times that's where you can't get answers to that question or that's where, you know, things change. And so one of our big focuses on the innovation side at Ogletree is, okay, well, what are our usage stats? Are people actually using this? Because if not let's do something else. Let's pivot, let's move it, or let's cancel that, and, let's see where we can better direct, our resources.
[00:09:09] Tom Baldwin:
[00:09:09] Tom Baldwin: Pulling on that string a little bit of, of external data, you talked quite a bit about combining firm data with external data. Where do you see that combination creating the most leverage? Is it client service, pricing, risk, or something else?
[00:09:21] Tim Fox: I think it goes for all of those, but from my perspective, where we get the biggest bang for the buck from it is really from a competitive advantage. When our attorneys can go out there and talk to a client and say, "You know, we have all of your data going back X number of years. We've run some analysis on it, potentially run forecasting on it," or, You know, I've had clients come to me and say, "Hey, can you pull this data not just for me, but for my three competitors? Because I wanna be able to go to my board and show that we are actually doing better than them."
[00:09:47] Tim Fox: I've had attorneys do the same that says, "Hey, can you go pull all of their other cases, pull their matters, figure out what we can to give them a report that shows that Ogletree is doing a better job. We're decreasing the number of claims that they have, or the number of charges, or the number of actions that they have against them."
[00:10:01] Tim Fox: That's where we get the biggest, from my perspective, value from the data and,pulling that together, because there's so few ways that we on the data side can impact the bottom line of the firm, right? We're not out there generally billing. You know, we're only tangentially related to bringing in business things like that.
[00:10:18] Tim Fox: But being able to impress a client like that, being able to jump on a pitch call and be able to talk about that or send a report to a client that does that, helps differentiate, that's one of the ways that we can actually help the firm, help the attorneys actually you know, bring in business and, and help the bottom line.
[00:10:32] Tom Baldwin: So speaking of adoption and usage, you've, uh, talked about the four barriers to AI adoption. walk us through those. is there one that you think kills more initiative than the others?
[00:10:42] Tim Fox: It's interesting, when I initially wrote that article, I think it was over a year ago now. It's funny how quickly some things changed, but how other things just stay the same. The four that I talked about is, is one, you know, can I trust the output, right?
[00:10:55] Tim Fox: I think we still hear that from people that, well, it hallucinates. There was just articles this week of the largest fine issued for a hallucination in a case, I think it was over $100,000, and people being referred to their bar organizations, things like that.
[00:11:08] Tim Fox: The second is, you know, I'm gonna lose billable hours, right? This takes away my billable time. Uh, Third, I don't have time to learn this. Then fourth, my work is too specialized. There's no way an AI could, can replicate what I can do. You know, for folks who have been in the space, there are responses to each of those arguments, right?
[00:11:23] Tim Fox: I mean, can I trust the output? Like, well, you're supposed to verify. Everything's supposed to be human in the loop, right? You're supposed to be reading that. You're supposed to check all of those citations there. Um, but you know, uh, you know, as I, I said then, oftentimes when people are saying, "Well, I don't trust the output," it's much more that there's something else going on, and it's figuring out what is that actual underlying objection to it.
[00:11:43] Tim Fox: We've had,I'd say, a lot of success in overcoming a lot of these objections. That's not to say that they're not there and that some attorneys aren't present, but you know, when I look at our adoption stats and I look at the attorneys that are using it, we're in the 70 to 80%, monthly, active users across our attorneys across our platforms.
[00:12:00] Tim Fox: That for me is a huge, accomplishment for us as a group, as a team. I'm not taking credit for that 'cause I have a team that is responsible for that. I think that really shows that we've addressed a lot of those because now what we have left to get to our late adopters and our laggards, right?
[00:12:14] Tim Fox: When you're looking at those adoption curves. That's a great place for us to be, and it's a much different place than we were, you know, 18 months ago when we were rolling out some of our first tools and trying to convince people to get there. From my perspective, what I see, as firms that are further along in the, I'd say the maturation their AI, is that really where I see a lot of focus now is less so on can I trust the output?
[00:12:35] Tim Fox: Like That's still there, but that's really, like I was saying, more of a catch-all for other concerns. It's a lot we're seeing, I think concerns around billable hours, like what is the impact on the firm here? We've all been moving so fast to get this technology adopted that now it's somewhat looking back and saying, "Okay, how does this impact us now?
[00:12:53] Tim Fox: Where are we gonna be in twenty-thirty? And is this going to have a significant impact on our revenue going forward, and how do we plan for that? How do we get ahead of that?"
[00:13:02] Tim Fox: Because for us, From my perspective, where I think we are isin a better position than a lot of firms because we have such broad adoption, we can start taking a look at, well, where is this actually impacting it?
[00:13:12] Tim Fox: Initially it was attorneys who were using these tools were attorneys who had too much work, and so they didn't care, right? They're like, " Well, I don't care that this saves me five hours here that I could bill because I have five hours more work over here that I can slot that right in."
[00:13:24] Tim Fox: I think we still see a lot of that because, like most firms, our attorneys have lots of work, and they're able to reprioritize and do other work there.
[00:13:31] Tim Fox: But I think that's gonna be an interesting conversation. It's things that we're starting to talk about and I think other firms are talking about. The other one that I think is interesting is, you know, the, " My work is too specialized, like there's no way
[00:13:42] Tom Baldwin: Yeah. See, I, I would have thought that would have been the one that has the greatest attachment to firms not seeing
[00:13:48] Tim Fox: uh, well, I think it depends. So, you know, at Ogletree, we're, I would say, lucky when it comes to AI adoption in that we have a pretty narrow focus, right? We primarily do labor and employment, and we do immigration. And then we have some other you know, some specialties in there. But we don't have as wide of a breadth as some of your general practice firms.
[00:14:05] Tim Fox: We don't have to deal with transactional work for the most part. We don't have, you know, all these other different litigation practice groups out there that we're focused on. So, we still have a lot of specialization. We have a lot of really, really good attorneys who've been practicing for a long time.
[00:14:19] Tim Fox: But I think the technology has gotten a lot better. When ChatGPT launched back in twenty-twenty-two, right, into twenty-twenty-two, you couldn't use that for anything reliable. It was great for, like, some things. You could do summarization, you could do basic things. But, you know, it was, it would give you back a few hundred words.
[00:14:34] Tim Fox: It would hallucinate half of the time. The technology now is just so much better, so much more accurate. Even I get impressed now when I put you know, couple thousand documents into a vault and I'm asking questions, and it's actually giving me responsive answers, and it's not running out of context, and it's not repeating itself or forgetting or, you know, going in a loop.
[00:14:53] Tim Fox: so I think it's come a long way. But also, as people use the technology more, they realize where it should be used and where it shouldn't be used. Definitely do not use any of our tools to draft a motion for summary judgment. It's not gonna go well for you. But use our tools to help you draft portions of it. Use our tools to help you locate evidence. Use our tools to help you do, you know, chronologies and things like that, that are, tasks that you can offload to it and review and have some confidence in it.
[00:15:17] Tim Fox: And so I think that's where it'scome from, is that my work is too specialized has more come to, well, my work is specialized, but you can help out with these individual pieces here, where I may not necessarily have the time I want to dedicate to them and they're lower risk, opportunities.
[00:15:30] Tom Baldwin: Interesting.
[00:15:31] Tom Baldwin: Kind of threading the needle on adoption, you mentioned, and I, I know you've done some internal training programs and hackathons with Summers. What do you think for a firm that maybe doesn't have someone in your role or, or is finally getting on the bandwagon, what's the minimum investment a firm needs to make in AI literacy before tools actually start getting used?
[00:15:52] Tom Baldwin: Or is that something you should do in parallel? Or h-how do you think firms should approach it?
[00:15:57] Tim Fox: for us, it's been really interesting to see how these adoption curves play out what we've been able to do looking back now going on two or three years when we started our journey here.
[00:16:06] Tim Fox: The first thing I would say is that AI requires people.
[00:16:10] Tim Fox: You can't run a serious AI program without staffing it. If you think you can just go out and license a platform and deploy it, you're not gonna be anywhere as successful as you would be if you actually had dedicated headcount to help run that. And that was one of the big takeaways we had because, when you look at typical software deployments at a law firm, you buy the software, you have your training department develop training sessions, you go out, you deploy it to everybody, you have remote sessions, you have in-person sessions, and then everybody's off on their own because the software is intuitive, they know how to use it or, they weren't gonna use it anyway.
[00:16:44] Tim Fox: But with AI, it's, it's different. One, there's a use case for literally everyone at your firm. Like, no matter what you're doing, you can find something where you can leverage. If you just draft emails all day, you can use AI to help you draft those emails and make them better and faster andsound nicer,
[00:16:58] Tim Fox: but you need to customize that to meet the people where they are and where the attorneys are and figure out those use cases, and they're not gonna do that on their own because they have too much work, and the learning curve is just, it's a little too steep. You're gonna have maybe 10, 20, 30% your early adopters who are gonna be the ones who figure it out, who find the value in it. And you may get organic growth from that, you may get word of mouth growth from that, and you may eventually get there, to a 50, 60, 70% adoption rate, but it's gonna take you years.
[00:17:26] Tim Fox: If you have the dedicated people to do it, you can move much more quickly. and you know, One of the things that I think about, is if I have a dedicated person who can get me to widespread adoption, let's say two months earlier, right? And in that two months, I've generated 100,000 additional prompts or 100,000 additional queries.
[00:17:44] Tim Fox: If each one of those prompts or queries saves me just one minute for my attorneys, that's 1,600 hours of time. And so if you think about it like that, that's almost a full year of an attorney billing. I don't have to pay this person an attorney salary because they're not practicing law. When you think about it like that, it starts making sense. You can make those arguments that it kind of pays for itself.
[00:18:04] Tim Fox: One of the things that we've pivoted to is dedicating to awareness and adoption, right? We still have people, we're still hiring people and have people to develop the tools and locate the tools, but now every conversation we have really starts with, "Okay, well, how are we gonna drive adoption of this tool?"
[00:18:18] Tim Fox: Because going back to what we were talking about earlier, if you don't have people using the tool, it's not worth your effort. It's just as important that you have the person to help people use the tool as having the tool itself. And so,at Ogletree, I've had a lot of success in, in being able to make that argument and being able to grow our team, grow our innovation team, to be able to support that type of adoption.
[00:18:39] Tim Fox: And so,that would be what I would say is probably the most important thing is to think through how can you get help to do this. Because if you're just one person, you're gonna be really limited in how you're able to drive change at your organization because you just don't have the capacity to do, multiple things.
[00:18:55] Tom Baldwin: Kind of going down the path here of building the team, buy versus build. You spoke about this back in October at the Legal Tech Connect conference, being a false binary. Can you unpack that a little bit? What really is the question that firms should be asking themselves or the vendor community?
[00:19:11] Tim Fox: It's never buy versus build. The false dichotomy there is it's buy and build. Nobody is going out there and only buying and only building.Neither one of those is gonna be a successful strategy because if you're only buying, you aren't able to serve your smaller communities within your firm.
[00:19:27] Tim Fox: All you have are big, broad solutions that you can sell off the shelf. And so,building needs to come in to fill in the gaps. And even if you are buying, you still need somebody to come in and build and customize it, right? If you've got Harvey, if you've got Legora, if you've got CoCounsel, if you've got any of these big legal broad solutions, you still need somebody to come in and, you know, build out your workflows or your agents or figure out how to, use it andcustomize it and fine-tune it and come up with, you know,your prompts and other things there help you build something that actually works there.
[00:19:57] Tim Fox: And so I think, you know, It's really important that every firm out there considers, well, how would we go out and how would we build something? obviously you're not gonna go out and build a big replacement for Westlaw or Lexis or Harvey or any of those, but you can build smaller solutions. You can build smaller tools, or you can figure out how you adapt these tools to build your own custom applications, within them.
[00:20:19] Tim Fox: I think it's important that people really think about what can be built? Because it really empowers you to have more freedom and have more capability to do that. I'm lucky, right? I have a development team. I have experience with software development and all that makes it easier.
[00:20:33] Tim Fox: You can just go into Claude, like I was saying, and build out your own apps, right? You can build them out, you can build out those proof of concepts, and then you don't necessarily have to build that yourself. You could take that to a vendor and partner with a vendor and locate a trusted vendor and say, "Okay, here's what I've built.
[00:20:45] Tim Fox: I've already shown it to my firm. They love it. We wanna scale this. Can you take my app I've built here and scale it?" That way you don't necessarily have to have, you know, an entire dev team. AI has made building much easier for law firms.
[00:20:58] Tim Fox: You just have to recognize that what you build still needs to be deployed and that there's real cost associated, with that, and that you set those expectations from the beginning.
[00:21:08] Tom Baldwin: I want to make a mental note that we circle back to this and the comment you made earlier about, lawyers are trained to become experts almost overnight on a topic and then dig into that for six months and then do that again. And there's a little bit of hubris that comes with that.
[00:21:22] Tom Baldwin: Those two things collide, and now we see kind of vibe coding and I won't say who, but there's people on LinkedIn talking about trying to do this at scale. But before we do that, have a few more questions on this topic about buy versus build.
[00:21:33] Tom Baldwin: So you do have a very unique perspective having been at LegalMation, you were the builder, and now at Ogletree you are the buyer and orchestrator and, builder as well. For someone who hasn't been on the vendor side, who has a role like yours, what would you coach them on in terms of, what you know now having been a vendor?
[00:21:51] Tom Baldwin: How do you evaluate vendors now, and what would you tell someone who's never been a vendor that they might not naturally think of as they're going through that evaluation process?
[00:21:59] Tim Fox: I think it does give me a good perspective, and I try and be sympathetic to our vendors because I've been on the other side of those phone calls. I think one, maybe I should apologize on this, podcast to all of the vendors that I've worked with because, think I hold them to a higher standard.
[00:22:13] Tim Fox: And usually when I'm on the call with them, it's because something's gone wrong and I get to, you know, be the, the bad cop or play the heavy to try and, get things going well. but what I would say for vendors, the number one thing that you can do is make us look good, right? We're on your side.
[00:22:29] Tim Fox: When I bring you into a pitch, I have brought you into that pitch because I think you have a good product. And if you come into that pitch and I've got, you know, our stakeholders. I've got our innovation council or I've got, our COO or, orother people who are the real decision makers. If you come in and don't make us look good, there's nothing I can do for you, right?
[00:22:49] Tim Fox: I can't help you with that. So when you're going into these, it's not necessarily an adversarial sales pitch. When people try and do the hard sell on me, or they try and ask me all the questions to try and, before they even show me the product, to try and convince me of why I need the product before they've shown it to me, that just doesn't go well.
[00:23:05] Tim Fox: You have to assume when people in the innovation space are having these conversations and demos with you, we want to like your product, right? If your product works, we both look good. We both win here. And so it's in your best interest to figure out what it is that, you can do to make us both look good to the people that we're trying to sell it to because we're both selling it.
[00:23:24] Tim Fox: I'm a salesperson inside the firm. Now, I don't necessarily get paid a commission, right? I, I, my, evaluation is different, but when I launch a product or want to build a product, I still have to go through that, that sales exercise there. And so I think that would be the number one thing to do is to think about how you can partner together, to figure out what the best way is to present that so you put your best foot forward.
[00:23:44] Tim Fox: I also would say, one of my, I guess pet peeves is when I don- I can't see your product, right? I, being a vendor, having been on the vendor side, I can tell so much more about a product and if it's gonna work seeing a demo of it than a PowerPoint. So if you give me a 30-minute PowerPoint presentation, all I'm gonna ask is, "I wanna see the product," and we're gonna have to schedule another call to see it.
[00:24:05] Tim Fox: So just for me, in particular, and maybe that's just, my nuance, I definitely want to see the product early. and the last thing I would say goes back to that first part, that we're on the same team, is that if I tell you no, it's not a good fit, it's not a whatever for it, it's not because I need to be sold more, right?
[00:24:21] Tim Fox: I don't need to get 20 emails from you explaining all the new features and try and have calls. I'll tell you, I'll be like, "Let's touch base in three months. Let's touch base in six months." That's my way of preserving the relationship and seeing, because things can change on, on both sides. You may have new features.
[00:24:34] Tim Fox: You may have other things. But it's not me being the gatekeeper. It's me saying, "It's just not worth the time to try it, to waste your time when it's ultimately not gonna be successful, at the firm." So,I think with all of the, VC funding and all the money coming in and all of that with legal tech now, I think a lot of those sales tactics from outside that, that may work with other companies are starting to infiltrate, certain vendors, where they are much pushier, they are much more aggressive, they are doing all these things.
[00:25:00] Tim Fox: From my perspective, that's not how I like to be sold, I like to have a conversation. I like to, see the product and maybe I don't know, maybe that's, that's, uh, I'm too old school in that space. But those would be my recommendations for folks, is try and have that relationship, show your product,work as a partnership, and recognize it's a long-term relationship.
[00:25:17] Tim Fox: People move around a lot. You don't want to burn any bridges. and so just, try and, um, be professional in those, interactions that you have.
[00:25:26] Tom Baldwin: Thank you for that. You answered the second question I was gonna ask is where does some of these relationships go wrong? And I think you just hit the nail on the head from a sales standpoint, not being overly aggressive, which I think is fair.
[00:25:36] Tom Baldwin: So when we look at the,ecosystem and, you look at the legal tech hub map, it's like size .5 font now because there's so many, logos and icons.
[00:25:45] Tom Baldwin: It's absolutely mind-boggling. and there's, vertical point solutions that span all ranges of practice areas. from where you sit in evaluating all of it, is that model sustainable, or does it start to create a sprawl problem?
[00:25:59] Tim Fox: It's crazy, right? I think, Legal Tech Hub reported there's like800 new legal tech companies in 2025. We just got stats. I saw an article today that they're, we're on track for more investment in legal tech in 2026 than 2025, which I thought was way you know, back in 2026, '27, when we were starting LegalNation, I wish we could have had funding, uh, like they're doing now.
[00:26:20] Tim Fox: That would've been a, a whole different ballgame. I don't think anybody would tell you it's sustainable. it's so hard to differentiate, a legal tech product now, and you also have, the specter hanging over everyone of the frontier models, right? You have Claude, who just released their Word plugin.
[00:26:35] Tim Fox: You know OpenAI is, is trying to recapture to be the front runner in all space. And then you have, Gemini out there, plus other companies that are working on their own tools there. So, I think, it's both a great time to start a legal tech company because there's a lot of easy money out there, but it's also a very difficult time because how are you gonna differentiate your product from all of these?
[00:26:55] Tim Fox: You know, it used to be Two years ago, all you needed to do was slap a custom front end on ChatGPT, add some custom prompting instruction, all of that, maybe a few features, and you go out and sell but now, more sophisticated firms are like, "Well, I can just build that," right? "I, I don't need you to do that.
[00:27:10] Tim Fox: I don't even actually need that because, um, we, you know, I'm just gonna deploy Claude to more users, and I'm gonna give Claude maybe a skill, or I'm gonna give Claude an artifact, and I'm gonna deploy that and do it that way." So, I do think that we will see I hope to see some consolidation. I think it is growing too fast.
[00:27:26] Tim Fox: I think also it's hard to stay on top of it. Earlier in the process, you know, three years ago, when all of this really kicked off, we had a tracker. We would track every single company that was out there, which ones we've talked to, what we thought about their product, who the contact was, all of that.
[00:27:39] Tim Fox: That's not possible right now. And so it's also hard for us to find the, really the diamonds in the rough. what are the products that would actually be valuable for us to have and for us to use? Because we're always, interested in those and the what is the, what's next for us and what's the hot new thing out there that we'd be interested in.
[00:27:56] Tim Fox: So yeah, I think we'll see more, more-- I hope we'll see more of this, um, consolidation of the market. But I also do wonder because, there's just not enough spend in legal to match, all of the investments that's going on there. And that's another thing that we wonder about as well is, well, is this company gonna be around in three years?
[00:28:16] Tim Fox: Like, what's gonna happen? Um, because it could get acquired, which may or may not be good. We've seen acquisitions go well where the product improves, but we've also seen acquisitions go poorly where the product has not done well. and in that case, you have made a big investment in it. And so that's a concern that we have when we look at a product is, well, you know, it's great to be early in the stage and get in when they're new, and you can be one of their first customers, and you can, capitalize on all that and the hype and the marketing.
[00:28:41] Tim Fox: But it also sets you up that you're stuck potentially with this vendor, because after I get 100 attorneys, 200 attorneys, 300 attorneys using a product, the difficulty in pivoting them to a new product is substantial, especially if we've uploaded data into that, if we've got, tens of thousands, hundreds of thousands of documents in a platform, we've got hundreds of thousands of prompts or queries in that.
[00:29:04] Tim Fox: How do I migrate that to a-another platform? And so those are all things that we're thinking about now when we have these conversations is, what does the future of this company look like? And is that something that we should be concerned about? because we don't have control necessarily over that.
[00:29:18] Tim Fox: And, I think some of the valuations of these companies require them to basically have every single Am Law 200 firm paying them multi-million dollars, for their valuation to actually stack up. And you have, like, 10 companies with that valuation. So they can't all have all of the Am Law 200 there.
[00:29:36] Tim Fox: And so it does make me wonder, it's like everything with AI. Is it a bubble? I don't think it's a bubble, but at some point there is gonna be, I think, some reckoning and realization, and especially with these companies that are able to just keep raising and increasing their valuation. At some point, somebody's got to run the numbers and be like, law firms are notoriously, um, frugal when it comes to spending, especially on technology.
[00:29:56] Tim Fox: And so I think we will start to see some pulling back as the market matures, as more firms really start reaching that next level of maturation in their AI journey.
[00:30:05] Tom Baldwin: Gr
[00:30:09] Tom Baldwin: eat segue because Tim, the thing we're starting to see now more, and this, I'm not gonna say this is every firm in the,the Am Law 200 or even the Am Law 50, but we are seeing firms that are making bigger bets, go to foundational models like Claude. That's seems to be the one people are talking about most these days, really asa horizontal layer that they can control and own.
[00:30:27] Tom Baldwin: And then as you get those niche, use cases that, oh, I've got the five lawyers in my ERISA practice that need something really unique, and I could either spend six months going and demoing and going through a POC and InfoSec and contract review, or I just go build something on top of Claude that meets that vertical need as we go.
[00:30:44] Tom Baldwin: how do you see that play out versus, without naming names, the big AI vendors that we see today? Is there a world where both can s- coexist, or do you see a future where eventually some firms own their own destiny and start to build everything themselves?
[00:30:59] Tim Fox: You know, it's a question I think that a lot of firms, to your point, are, are looking at. You know, us, Us as well. We have big legal, specific providers, and then we also have, you know, frontier models, available. I think it's still too early, to see how exactly that's going to play out.
[00:31:15] Tim Fox: I also, going back to my earlier point, like, legal is a relatively niche market when it comes to tech spend. it's more than it's ever been, but, historically, it hasn't been super attractive. When, when we started LegalNation 10 years ago, we learned that lesson the hard way, that, just 'cause you have a great idea and you say, "Oh, I-- if I just get 1%", right?
[00:31:32] Tim Fox: 1% of the legal spend, that's a billion-dollar company. but that's-- every legal tech company says, "I just need 1%." Uh, and getting there is far harder than you think. So, I think what we're seeing with Claude is, is super interesting. You know, CoWork, the plugin, the legal plugin they have, they just announced the Word plugin.
[00:31:49] Tim Fox: They have all of these other things that are there. But, we have, Claude at the firm. We're currently piloting it, and there are some... it's a great tool. It is a great platform, but it doesn't replace everything that we can do with our legal specific tools. and we have attorneys who say, I actually like what we have over here more than what we have in Claude."
[00:32:07] Tim Fox: And Claude has other limitations. I think also they're figuring it out. right now, CoWork was a huge thing, and I think there were all these LinkedIn posts about CoWork. And going back to your other thing, about, people posting on LinkedIn, "Oh, I vibe-coded a replacement for Harvey and Ligori over the weekend.
[00:32:22] Tim Fox: It's so easy to do," right? That really misses the mark, because the value of the platforms isthe governance, the security, the structure, all of those unsexy things that you need to feel secure in a regulated environment like legal, that your data's safe, that your clients will allow you to use it, that it's gonna be around, that you can integrate it, that you can do all of those things.
[00:32:41] Tim Fox: And so CoWork, for example, is a super useful platform, but I don't know of any firm that can safely deploy that and comply with their governance obligations outside of like a sandbox environment because, there's no audit trails for it. It still can do things that you don't want it to do, even if you put safeguards and limit it, you don't have complete control over it.
[00:33:02] Tim Fox: And so from my perspective, it's super interesting, but that's probably where we'll be in a couple years. I don't think we're there yet. There are other things that you can do that are very powerful with the platform and other things like that. But I also just don't know how much it's worth for these frontier models to spend a lot of time in legal, because it's a very competitive market.
[00:33:21] Tim Fox: There's a lot there and, OpenAI was an initial big investor in Harvey. So if they come and try and go after the legal market, they're kind of cannibalizing what they invested in for Harvey and what Harvey was supposed to do for them. When you look at Harvey and you look at Lagora and you look at CoCounsel, there's not a lot of room left in the market to say, "Okay, well let's try and replace..."
[00:33:40] Tim Fox: As I was saying earlier, to get off one of those platforms after you've had it for years is a huge transition cost. It's never gonna have the exact same features. You're gonna have upset attorneys, all of that. And the last thing I would say is, not everybody needs the latest and the greatest, right?
[00:33:53] Tim Fox: This is something that we used to talk about when I practiced is like, well, does the motion have to be perfect, right? Do we need to spend another 20 hours on it, or are we gonna win on the basis that we have here and let's save the client money? or do we need to retain this expert? Do we need to do this deposition?
[00:34:06] Tim Fox: You're always having those kind of conversations in your mind to figure out, how do we win this case most economically. And I think it's the same with AI. If you can get with a current tool to 80%, and 80% is enough to win your case, you don't need to spend that extra time and that money to get to 100%.
[00:34:21] Tim Fox: We see that all the time. We have attorneys who don't necessarily need to have the latest and the greatest. They're happy with what they have, and that's what they know how to use, and that's where they get the benefit from. So trying to get everybody up onto the latest model and the latest this is just going to lead to a lot of frustration on your part, but also on your user's part, because once you have something that works well, you just wanna keep it.
[00:34:41] Tim Fox: I get annoyed anytime, you know, some app automatically updates, and now I have to find, figure out where these new features are and do all this new stuff. And I'm like, "No, it was fine how it was. I liked it how it was. Even if you've made it better, you haven't necessarily made it better for me." We'll see how all this plays out.
[00:34:56] Tim Fox: you know, I could be wrong and all of a sudden, you know, we have Gemini and Claude and OpenAI is what everybody's using. But I don't think we're gonna see that. I, I think that there's too much of a, a barrier to entry that's already been set up, and other concerns in security where, the vendors we have now are also much more customized.
[00:35:11] Tim Fox: You can't get somebody on the phone at Anthropic unless you're paying them, I think, close to half a million dollars. and so What do you do in that scenario? and the same goes for all these other vendors, these other frontier models where I just don't think we're big enough fish for them to wanna jump into our, our pond here.
[00:35:26] Tom Baldwin: You know, Tim, I heard something else adjacent to this where, you get the big three, Harvey, Ligori co-counsel. And I was talking with a friend of mine at a firm and they said, "Hey, look, there's some really cool technology coming out and vendors that I'm really interested in. But at the end of the day, if I were to pick one of them over one of those three and there was a problem, I'm gonna be in a lot of hot water because there's some safety in buying one of those three products that if it does make a mistake, no one got fired for buying IBM.
[00:35:54] Tom Baldwin: No one got fired for buying one of those three. And if I go down the path with a newer company, and they could, it could yield the same problem or, you know, lose, say, a case just like Harvey Ligori could, but because it's not a name brand, it puts me in hot water." So now all of a sudden, and I'm not trying to dissuade anybody from starting any software companies or AI companies.
[00:36:15] Tom Baldwin: but there's almost this, Safety in numbers that people that are in the space are looking at saying, "I really don't know that I want to stick my neck out," and be, to your point, on the bleeding edge. so it's, it's just an interesting place we find ourselves in.
[00:36:27] Tom Baldwin: being at Ogletree, labor and employment laws, heavily driven by regulatory data.
[00:36:32] Tom Baldwin: You got OSHA, DOL sta-statistics, lots of other things. how do you see, all of that changing the way firms like Ogletree or your competitors or big firms with large labor and employment practices counsel, proactively rather than reactively?
[00:36:46] Tim Fox: Yeah, I think this goes back to what we were talking about earlier, the impact that data can have for our attorneys and for our clients. so I think the regulatory data, and this also ties into earlier topic, regulatory data is one piece of it, and what you can get from the government and what's available there is huge because that's really gonna be, cross-industry, cross everything.
[00:37:04] Tim Fox: The other piece of that is we have our own internal data, right? If we've been representing a client for an extended period of time and we've been handling a significant amount of their work, you know, if you put those two together, you can start answering some interesting questions. and previously it was just too much work to do it.
[00:37:18] Tim Fox: If you wanted to do it, it would have to be a manual process to do it, you know, one client at a time, one customer at a time and, and figure out, how to pull that data. Now with, with AI, it's gotten a lot easier because a lot of this data, even though it's you know, quantitative, it should be numerical data.
[00:37:33] Tim Fox: It's stored in a qualitative fashion. Um, and To be able to merge the two of those to say, "Okay, well, what were the causes of action asserted in the, you know, these complaints and these, let's say, 5,000 complaints across this industry that we represented, and what are we able to pull from court dockets across this?"
[00:37:48] Tim Fox: All of that data is gonna be textual. You previously would have to develop your own taxonomy, you'd have to develop your own extraction algorithms. You'd have to figure out how you can pull it from APIs or other ways. You'd have to OCR. All of that middle piece is now, that extraction piece is, is done by AI in, in a fraction of the time.
[00:38:03] Tim Fox: And so I think that makes the data be a lot more accessible. But going back to what I was saying earlier, like I'm a data person. I understand data. I know how to talk about it and use it, but I'm not the one talking to clients. I'm not the one trying to sell them on things, and I don't know what a particular client cares about because not every client is, data-driven, right?
[00:38:23] Tim Fox: You could go to a client and say, "Oh, I can predict your litigation spend over the next three to five years," blah, blah, blah, and they say, "I... That doesn't matter to me. What I'm actually focused on is the same thing as you are. I need to drive AI adoption. I have all this, advice that I need to give to the board on how we prepare our people.
[00:38:38] Tim Fox: I need to lay off XYZ number of people because of this." And so there can be a disconnect for us as data people to focus too much on the data and think the data is, the most important thing, when a lot of times it's figuring out when and where that data actually adds value. And that's, I think, the important thing.
[00:38:53] Tim Fox: And that's really where you need the attorneys. You need them to come in and to help. They have the relationship with the client. They know what's going on, and they can tell you, like, this is where that, matters, and this is where it's not gonna matter. Because if it's not gonna matter, it doesn't really justify, spending the time to, to provide all of that insight and data to them.
[00:39:10] Tom Baldwin: We like to end these sessions, Tim, and, and I think a lot of firms, maybe not so much with AI because, some firms feel this is the first time in thirty years that I've been in the, the space where, the lawyers are driving adoption more than IT forcing tools on lawyers, right? The tables have turned a little bit.
[00:39:29] Tom Baldwin: but from a data standpoint, you mentioned, you're a data guy, which I, I, I know you are. and if we were to go back and look at that sort of unsexy, back end of, of AI or, or analytics in general, we like to kind of give folks that are maybe just starting their journey with data, some practical tips and advice.
[00:39:47] Tom Baldwin: You've gone down this path. You kind of know what this looks like. for firms that feel like, "Hey, before I go down the path of getting my data all sorted out, I really need a data strategy. I need to get data governance.
[00:39:57] Tom Baldwin: I should have a data council or data committee, before I do anything else." How would you, counsel firms to sequence events? Should they do that before they start getting their data in a central data platform? Should they do those things in parallel? Should you flip the order? What have you seen be effective?
[00:40:13] Tim Fox: That's a tough question. It's kind of chicken and the egg, right? Where-- Which, Which should come first? What I would recommend is, is probably a dual track approach, doing two things concurrently. Because I think the two most important things you can do, on the one hand, are start showing the value of your data.
[00:40:28] Tim Fox: And you don't need a committee, you don't need an expert, you don't need anything other than some data that you want to answer questions about available to you, and then what you wanna show with that data. Because that's gonna really help you sell the value of this to people who may not understand it, who aren't data people.
[00:40:43] Tim Fox: But on the other side, you need, Some sort of group. You need a working group, you need a steering committee, you need something else because no single person in any firm of any reasonable size can drive an initiative forward. If you're on the attorney side, to your point, you probably don't have IT on your side.
[00:40:58] Tim Fox: And if you're on the IT or the innovation side, you probably don't have the attorneys on your side. And so, you need to have a group that contains both of those people to say, "Yes, this is a good idea. Yes, let's go to firm leadership. Yes, you have support for this." And so to get that group to support it, you also need the da- you need that data, you need that initial thing that you've built to show them the value of it.
[00:41:17] Tim Fox: And so that's really where I would start. If you start trying to come up with a comprehensive data strategy or drafting policies or governance or any of that, you're gonna get bogged down. You need to have something that's exciting, that gets people interested in it. And then all of that can come later.
[00:41:31] Tim Fox: It will come. At a law firm in particular, you're gonna come up with governance, you're gonna come up with policies, you're gonna come up with that strategy, but save that for when you are ready to do that because if you can't get buy-in from firm leadership at the beginning for what you wanna do, then there's no point in drafting all those governance and all those policies 'cause they're not gonna go anywhere.
[00:41:49] Tim Fox: The other thing I would say on top of that, as we've been discussing, is AI has made it so much easier. Now, all you need to really be able to do is ask the question, and then the AI tool can go out and tell you how to get that data. It can even write the API calls for you to go pull the data, or it can write the scraper for you, or it can tell, draft the email for you to send off to your DBA team to say, "Hey, can you pull these tables?
[00:42:10] Tim Fox: Can you pull this data for me? Here's some draft SQL code that may or may not be, helpful for that." And so I think AI has made it much, much easier for people to get into the data because all you have to do now is be able to ask the question. You don't necessarily need to understand the structure of it and, and how it all relates.
[00:42:26] Tom Baldwin: One last thing. So, um, if, If you were trying convey a message to the leaders of law firms, what mindset do you think law firm leaders need to develop the most to see the shift from where we are now to where things are headed in the next few years?
[00:42:42] Tim Fox: I think what would be most helpful and what I've seen for law firm leaders is to go spend a few hours using the AI tools that are out there. Just go sign, sign up for, Claude personal account or a ChatGPT personal or Gemini, or if you have platforms available at your firm, just commit to actually spending time to use that tool how you would in your practice.
[00:43:05] Tim Fox: In general, that's gonna give you that sort of aha moment, that epiphany of, oh, this is different. This does have the potential to impact how we practice law. And once you have that mindset, I think it starts flowing down to your discussions, to your decisions to say, we do need to actually think about this because it's not going away.
[00:43:22] Tim Fox: It's only getting better." It's been, three and a half years now, and it's only grown in adoption and usage. I do think that, most firm leaders are aware of that conceptually. They know that this is coming, but until they actually see how it would ch- change how they practice law, it's a little difficult to articulate that.
[00:43:41] Tim Fox: but if they do that and then they have all of their practice group leaders or other senior, uh, attorneys at the firm, and even on, like, the administrative side of the house, having your directors, that's a big portion. Every firm has just as many admins side as they usually have legal side. And so having them go through that exercise as well to really think about it helps figure out where the firm's gonna go, what you should be doing, what tools are there.
[00:44:04] Tim Fox: And it also is really helpful because the more you use AI, the less you worry about it taking your job, Because you understand its limitations, you recognize that this is not a agentic AGI. This still requires human in the loop for almost everything. That also gives more confidence in them to say, "Okay, we're not losing our jobs.
[00:44:22] Tim Fox: Let's figure out how we adopt this. Let's figure out how we move forward." So that would be the biggest piece of advice I have is spend a day doing all of your work with an AI assistant of your choice, and then when you come away from that, I think that will really help guide your decision-making process and, and where you want to take, direct your firm to go.
[00:44:39] Tom Baldwin: That's awesome. Tim, we're at time. Thank you so much for sharing your journey and insights with us today. Um, that's it for this episode. And if you enjoyed the conversation, hit the subscribe button so you'll never miss the next episode. Thanks for listening and, uh, we'll see you next time on Overruled by Data.