
Zach Posner reveals the legal tech bets reshaping PI firms—and how to build a future-proof, profitable Law Firm 2.0.
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Most agencies sell promises. Rankings delivers proof. We've taken firms from invisible to number one in the toughest PI markets in the country. And while others are still scrambling to figure out ChatGPT, we're already optimizing for AI search. So your firm is the first answer clients see. Lead the pack, don't get left behind. Visit Rankings IO for aio, also known as AI Search, and start dominating search today. To beat insurance companies, you need the best legal tech in the game.
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The interesting part about legal is historically it's been a decade behind and for the first time I think that we're like right there.
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But legal services are a crowded $1 trillion industry.
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Whatever tech you're using today will be the worst tech that you ever use.
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So let's get insight on the state of legal tech, where the industry is headed and what you can do today to dominate the competition.
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The secret to this space is this.
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Is Personal injury mastermind Pim is powered by Rankings IO. I'm Chris Dreyer. Each week we get tactical about legal marketing intake and operations. Today's guest has backed over 80 legal tech companies. He is the co founder of the only venture capital fund exclusively focused on investing in legal technology companies and has everything you need to understand the legal tech boom. Let's go.
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I'm Zach, co founder of the Legal Tech Fund and our goal is to invest in companies that are transforming the world of law. Most of our companies are early stage technology companies. What we're trying to do is find the best ones in the world, invest in them. Not only financial capital that most people immediately think about, but it's more human capital and it's more saying, hey, this is an interesting vertical that has tons of different business models and we try to provide guidance and relationships to help these entrepreneurs accelerate their journey and really reach their full potential. That's our goal.
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Most of the audience listening are the bootstrapped, right? Or they're, they're coming off a big case and that's kind of how their funding can we kind of break down just before we get into this, like maybe just some of the different types of leverage and what the tech fund is on the venture side.
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So there's tons of different ways to finance a business, arguably the best, and the timeless one is bootstrapping a business. But then there are some businesses where, let's say it's a technology business and you know you're going to need a significant investment over the next couple years before you can really start to generate revenue. If you're an attorney, you can go out and you can find that first case and you can almost leverage that to get started. But imagine if I told you, hey, you're going to need five software engineers and you're going to need millions dollars of infrastructure to even get your idea off the ground, to be able to show it to somebody. So that's where we come in. And we are basically there to say, hey, we'd like to provide these companies some financing and in exchange we buy a little piece of the business, you know, and the theory is that that gets them the leverage they need to almost have explosive growth once they're ready to get going. So you can say that like a bootstrapped entrepreneur expects, you know, a very consistent path. And they may have, you may have some good cases, you may have things on those lines, but we are expecting like zero revenue and then boom, lots of revenue. Got it. We're not playing to a venture fund in general is not playing to invest a dollar and get two back. While that's a great outcome, you know, what we're playing for is to invest a dollar and to get ten plus back and in some cases a hundred plus back.
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Team just launched the Legal Tech Lab. The next evolution in your core thesis of Law Firm 2.0. You've backed 70 + legal tech startups. What do you see? What is Law Firm 2.0?
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We are seeing a cohort of software companies that are trying to come out using AI to perform more and more services. And it's saying there's some, a lot, there's a huge untapped market for legal services where it's just not cost efficient for attorneys to focus on certain areas. But we believe that technology can help in some of these areas. And what we're seeing are entrepreneurs that would historically go build tech companies say, you know what, we're going to go try to build a law firm. So that's what Law Firm 2.0 is. And if you think about it from an evolution on the tech side, we saw a lot of tech historically come out, charge you a monthly subscription fee. We then saw a lot of tech come out and say, you know, we're going to charge you on a per transaction fee mostly, so you guys have a clear way as to expensing that back to a client if it should make sense. And it's an expensible type of item. And now we're seeing some things take that a step further and saying, how can we do more of that work? This is not stuff that necessarily competes against attorneys. This is this is more stuff that attorneys are not necessarily focusing on right now.
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You have a better view than anyone in regards to legal tech ecosystem. I mean, you see which companies there are from a whole mix. There's a lot of competition in the, the medical chronology and demand letter space. I'm excited to talk about a range of things that I'm probably unaware about.
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We're tracking about 2,800 companies, you know, on a monthly basis. We're getting connected to about 100 new companies every month at this stage. So the explosion here, as I'm sure you're all aware of from your inboxes, is really unprecedented. You know, I know your crowd's a big plaintiff for PI types of folks. You know, this is affecting everything. This is affecting the traditional corporate or transactional lawyers that bill on an hourly basis. This is affecting corporate legal groups, the general counsel's office. This is affecting legal operations within corporates. This even goes all the way down the SMBs and even down the consumers. We're seeing lots of interesting things.
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You know, it's also a mindset shift that you have and I think a lot of people need to have is it's not to be afraid of AI and tech and think of it like, you know, from the pessimist side, it's like, what can it do for me from the optimist side, like the, you know, I think there's a lot of opportunity, you know, you might be one of these firms that can shave off some expenses and get some more margin to let you do more exciting things.
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We think there's going to be a significant amount of expenses that you can save. And really it's almost about freeing folks up to take on more high level work. Something that I think about a lot is the advent of the ATM happened in about the 1970s and people said that's the end of the bank branch. And from basically 1970 until today, I don't have the number, but I think directionally we're talking about the number of bank branches increased by 3x now some of the roles, there may be less tellers, but every bank branch now has consumer loan officers, it has business loan officers. So the roles shift a little bit. But overall, like, you know, the application of technology, I think there's, you know, some people have deep concerns about it, but we think it's going to create more opportunities for everybody to do more meaningful work.
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So I guess, and I'm, I don't want to ask this next question from a, like a negative side. Maybe you can help wrap My head around this because, you know, like, Jack from Clio was on the podcast, you know, amazing company, and they're like series F, right? Like, so at what point? And I don't know what their valuation was like $2 billion. Like, like, so, so keep going. Okay. Yeah, okay. Way, way higher. Yeah, way higher. Twenty billion, maybe. I don't know, more. It's like, I guess because their vision and their ceiling of what's possible is just more extreme than what I'm thinking. Like, I guess they're, they're doing it for acquisitions to supplement their existing infrastructure because they're already, I guess, generating revenue. But, you know, at what point do you start taking the revenue versus continuing to build the infrastructure?
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Well, you know, that really depends on the opportunity ahead of you. Like, when you think that there's a massive opportunity ahead of you and the kind of the competitive landscape, then sometimes it makes sense to just continuously be taking capital to get market share, you know, because if the flip side is, hey, we can be profitable and grow very slow, that's fine in a world where there's no other competitors, but if there are other people biting against you, then somebody's going to go sign up that customer. And do you want the capital to have the extra marketing resources? And then there's also places where the capital just makes sense. Like, a lot of this stuff comes down to a construct that we think of. It's called unit economics. And it's just saying, hey, I'm going to have to put out X amount of dollars to go acquire a customer. But I know that that customer is worth Y, which is hopefully significantly larger than X. So it makes sense to go out of pocket negative $100 if I think I'm going to make $1,000 on that customer. And the more that you refine that customer, it's the same thing you think about when you, when you use, you know, for an SEO campaign or, you know, or an SEM campaign, hey, we're going to spend X amount of dollars and we believe we're going to get this return back.
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I'm excited to talk about the companies too. And like, you know, the PI firms listening, you know, starting with the attraction, the acquisition side, you know, what are some of the, you know, exciting, you know, new tech, tech enabled AI things that help on the lead generation, the marketing or sales side in your world.
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We've invested in a company called Lexamica. And I'm not sure if you've come across Gabriel before, but what, what they are doing is basically saying hey, we want to be a marketplace for people to come and get referrals and at the same time put their referrals up there. And how do you match the case with the best possible practitioner to execute and go work against that case? So for us, we think referrals is a pretty big, you know, we think it's a multibillion dollar per year opportunity. And we think that a lot of this stuff, you know, not only the, the acquisition of them is done in old fashioned ways, but then how do you report on them? How do payments change hands? So we get really excited about something like that, if that makes sense.
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Yeah. You know, and we've had Bob Simon on it. He's got attorney share and you've got, it looks like, I think those are the only two companies that I'm aware of that are in that space. And a lot of times you see two winners. Right.
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I think that's a learning is that like this space is big enough, you're going to see multiple winners.
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Yeah.
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Like I've been investing in this vertical for directionally 10 years and then with a fund and day in and day out since 20, 19, 20. And it's like a lot of the companies that we've looked at have been successful.
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Yeah.
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And it's, it seems like there's just like one thing we talk about internally. Is this space just so big and growing so quickly that everybody can do well.
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Regulatory changes are making room for new players and they're moving fast. Some of the most interesting tools are finding value in cases you've already earned. Here's how these companies are using the data to surface opportunities that give forward thinking firms a real edge.
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With everything that's happening with the ABs in Arizona and the different laws that are changing, there's companies that are trying to mine data in innovative ways to generate leads. You know, there's companies that are going back into attorney's files to say is there things that were missed? Are there other opportunities that come from our clients? There's companies that are scanning the dark web to find data breaches. You know that in some cases are informing the companies before they're even aware of some of these things. So what we're really just seeing and all of these are tools that like without technology it's almost impossible to do. So I think that we're in this like V1 where people are saying, hey, there's a lot of expansive opportunities that technology can help with. How do we try to take, take advantage of some of these and build Businesses around them.
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Yeah. And I think that's, I think that's excellent. And I think there's so many advantages of doing the co, you know, doing it, you know, kind of the, the old school with labor, you know, getting your leverage from that manner. We've seen people try to take advantage from labor from a nearshore perspective, but then you got the tech advantaged.
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I mean, I'm curious your thoughts. We're seeing a big rise right now. We've probably seen 15 effectively automated call centers using automated LLMs to interact with clients. To me this sounded a little bit crazy. I mean, you guys spend a lot of money to generate leads and to turn that over to a robot. But you know, I'm watching, we're watching the technology improve and the user experience get better. I'm curious like what you think about.
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Things like that, you know, transparently I'm an investor in capture now, so. So I think positively of it.
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I think we're big fans of those folks.
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Yeah, I think first of all, I think what they're doing is amazing. You can, you can barely tell, you know, if you have the medical, you know, the hospitals, the banks, they all do some type of tech enabled intake and it's very common. Like we're familiar with it, it's just less common, I guess in the legal space. But I think it could be more. Not as taboo or more natural in the future. I do like it just when you do a comparison versus cost of the manual, even if they're doing the nearshore. Right. Some of these call centers, the costs are just so prohibitive, you know, especially if it's an overflow scenario. So I think there's some advantage there. One of the things that I think I just had David Haskins on and he's developing this, where the agent is listening to all the calls and flagging missed opportunities and like grading the intake reps. And you think about it from a quality assurance perspective. Like if you had a great quality assurance rep, like how many calls can they listen to versus the AI agent listens to all of them.
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So a couple fascinating things there is. Like we've heard people saying, hey, if you rely on this stuff too much, that can be borderline malpractice. Like two years ago I was hearing that could be malpractice. Now I'm hearing, well, if you don't use some of this stuff, is that not, you know, and then the other thing, look, a lot of the companies we see out there, like what you just described, that kind of came out A year and a half ago for general sales folks, not in the legal industry, just generalist sales teams literally watching the transcript as it goes by, giving a flag saying, you should mention this or you should mention that. The evolution of software where things start out general and then they get tailored for a specific vertical. I mean, the interesting part about legal is historically it's been a decade behind and for the first time I think that we're like right there. I mean, we are maybe six months behind and there is a whole cohort of entrepreneurs that are trying to attack this vertical that we've never seen before. The engineers from Google, from Meta, from Netflix, which has its strengths and weaknesses.
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It's so interesting. Like even myself, we're trying to use more of the LLMs and try to do our custom GPTs and things per client, right on a client level. And then there's some hallucination and some do this and that. One of the things I was excited about was we have an AI hooked up to our HubSpot that basically looks at the communication and does sentiment analysis to help with retention. So if it identifies any things like, hey, we're not getting enough cases or any negative sentiment, it goes to Slack and it's like, okay, we can address this. And it's like just wild some of the capabilities. And I was thinking like, you know, we've had HONA on that would be an amazing thing for those tools to do sentiment analysis for the clients so they can kind of optimize for those five star reviews. And it's just, it's wild. AI search is changing the signals and paid media is tightening every week. The firms that adjust early will be the ones out front. I'm Chris Schreier. Stephen Willie and I will walk you through what actually leads to visibility in sign cases in 2026. Sign up for the webinar now and take the edge your competitor leaves on the table. Performance Marketing in 2026 December 16th at 3pm Central. Free registration at Rankings IO Webinars. Don't leave your boy hanging. Me and Stephen Willie are going to crush it. We're going to show you how to sign cases in 2026 with performance marketing. That's the name of the game. Let's make that money.
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So yeah, my guess is all of them are adding this stuff. And I think that's the other thing that's interesting is it's. This stuff is easy to layer on. So people ask us how many of our companies are thinking about AI and it's, it's like 100%. Now that may not be like AI first, but it may be there's nobody we have. One of our early investments that we couldn't be more proud of is a company called Proof. And it's effectively Uber for process serving. But they are doing things now with affidavits with the way that you set up a serve with LLMs to make these to just like take all of the work away from apparel, make it so much easier for them. Take a half hour process and make this a 30 second process. And at the end of the day if you just take, if you just break down any process one step at a time. We're now seeing LLM tools or AI tools that can help with almost everything.
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You know, I've heard you say this in another interview. You've mentioned, you know, the shift from solutions to infrastructure. Could you kind of explain what you mean by that in regards to maybe how a PI firm is built?
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If you think about all the work that a PI firm has. Right. It's a series of small steps that collectively get you to an end goal. And the more you can break down those small steps, the more you can pinpoint places where technology can slide right in. And I think that the answer is not to boil the ocean and replace every. It's just like, how do you start with like one little piece here? One little piece here. One of our companies foundation AI is just thinking about the incoming mail that comes into you every day.
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Yeah. I think Sweet James uses that.
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Yes. How do, how do you organize that? How do you immediately get that into the right client file? How do you do things along those lines? Literally one step at a time. How do you think about these things? And I think that there's a lot out there right now and you're about to see a lot more.
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What are some of the merging ones that you've invested in and that are just doing things that specifically catered to where PI could potentially find some real advantage that maybe we haven't talked about.
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A little bit more. On the, on the mass tort side, there's a company called Pattern Data and there's a lot of things out there for medical record retrieval and things along those lines. But what they're doing is like they're structuring all the data from the medical record and they're synthesizing that against the profile of a tort and they're basically telling you how effectively good of a case you have and what level of damages that your client may qualify for. This is as an alternative to Hiring a bunch of offshore nurses and flipping pages. You know, of hiring a football field with a nurse and flipping millions of pages and not understanding what the characteristics of the inventory that you're working with have. And then what happens when something changes or you want to run a scenario? What happens if we include this group? What happens if people were damaged by this and it wasn't included? Instead of going back through everything, you just run a query and this stuff's available on a real time basis. Absolute game changer. I mean there's some stats that come out of that company that say some of their users are in this for north of four hours a day. And that's really the test of what we think about like how often are you logging into some set of software and the more often you log into it, the probably more impactful it is to your life. Like what software are you in for four hours a day?
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What about the CRM or like any of the project management or are basically the big companies your. Your file vol lines and cleos and little are they already kind of hitting that space?
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We've intentionally stayed away from some of them as a function of I mentioned we started our fund in 2020 and those were. That category was kind of established. You know we're super curious some categories that make sense that they feel like they're wide open and some feel like, well there have already been a couple winners and and it makes sense for those winners to continuously keep going. Like Clio just made a brilliant acquisition. They're in the billions of dollars as you Jack's extraordinarily strategic. But it is interesting that now we're seeing things. We're looking at a lot of timekeeping softwares right now. But the interesting part is if somebody puts a little widget on your desktop and they track everything you do with the purpose of keeping time and trying to understand what matter you're working on. One theory, they know every file you've ever touched associated with that. So we're like saying hey, could there be a completely different paradigm of practice management solutions? You know then the other stuff that like we're really thinking about is like you mentioned all these categories and all these different software. We think this trend of more and more software companies happening is just going to continue. Well where's like the middleware that lets this software communicate with each other. We're really interested in some payment stuff, you know, how distributions are, how disbursements are made, credit card processing things along those lines. We invest in a company called Confido There's a company called JuriSpay which is starting to help finance some of the case costs that attorneys have where there's a big litigation finance market. But there's not necessarily, you know, there's a lot of money laid out for every single one of these.
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There's like a monopoly on that one side. But yeah.
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On the lower side, we're not seeing anything. And you know, we're looking and saying, well, wait a second. If an attorney is using some of these digital tools, like we think we're about to come up with some data saying they may have a higher probability of winning their case. So maybe it's like a really smart move to help them finance some of these until their case ends up settling or they win their case. So that's a company called JuriSpay that we're excited about.
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What about on the trial side? Right. Anything to help. Maybe you're the type of story that you're going to tell or what the amount that you should be asking for and those types of things.
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So, yeah, we're seeing some interesting things pop up. One where I hope to have more good news shortly about. But what we're seeing is like they're looking at transcripts and trying to understand what expert witnesses have done in the past, what they're going to say. We saw a cohort of stuff a couple years ago where it's about judges and their sentiment. We have not seen any of those really take off. But even down to the word, hey, what are the words that you don't want to use in front of a judge? Because we've seen them get upset about those words before for. So we're seeing on the expert witnesses, we're seeing it on the prediction of what a case is worth, what the value is. That's almost the holy grail that we have not seen.
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The reverse colossus.
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Yeah, exactly. You know, but that requires a lot of data to get there and we just haven't seen that quite yet.
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Yeah, I've always wondered if some of these companies, if that's their end goal. It kind of looks like it, but I'm not going to name names. But it is.
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But you have to. I mean, you have to think about who has the data at scale.
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There are certain cases ssdi, maybe there's just low value fees. Has AI or tech been able to open up maybe practice areas that are potentially monetizable now that weren't before, maybe opened up the tam. Is there anything on that side?
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That's what this Law Firm 2.0 concept is we've seen two or three entrepreneurs trying to tackle the Social Security in the last couple months. At the end of the day, it's a, you know, a lot of this stuff that's if then analysis and it's lower value creates big opportunities. And for that one specifically, the threshold's not as high where I don't believe you need to be an attorney. I believe if you have like some, there's some qualifying level of knowledge where you can represent people in and around Social Security. So I think that that, that scenario you'll definitely see and that's. We've seen things like criminal record expunctions, like things along those lines, like, pop up for this Law Firm 2.0 stuff, you know, and on the consumer side, we just, we think it's infinite. We think like when somebody is going to rent an apartment on Zillow, like, why doesn't Zillow say, you know, can you look at this lease and review this lease for us? Or this morning we actually, it was announced we invested in a company called hello Prenup. And it literally walks a couple through the steps to engage in a prenup. At any given stage, anybody can off board from that software and talk directly to a lawyer. And you know, and then in the meantime, there, there's a lot of fun stuff that can come from that. It's the, it's the start of a family coming together with disclosing all their finances. Well, maybe there's wealth managers that would be interested in that cohort or maybe there's other services that can be. Maybe there's trust in estate services that can be provided. So like, that's the neat part with the legal stuff is like, if you help people with their legal problems, there's a lot of like exhaust data that comes out that can create additional opportunities for these companies.
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Very cool, Very cool. I think it's interesting from your vantage point, you're looking at it at a higher, like, bigger picture. Like, where do you see the PI space? And particularly I'd like you to maybe give your thoughts on the auto because now we got the Robo taxis, the waymos the Bill Gates has a famous.
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Quote that says, people overestimate the progress that technology will have in two years and they underestimate the impact that it will have intent. And if you actually think about the entire Uber story for a second, like if you start with Uber 2008, 2009, they say we're going to replace a black car and we're going to like connect people for black car services. And people said, wow, interesting little market. Then they said they're going to do UberX, which five years later, which turned into replacing effectively a taxicab. But what they didn't realize at the time was it effectively became a car ownership replacement. So the market was much bigger than anybody ever dreamed. And then that had like second order of magnitude effects where like kidney donations were or DUIs were down because people wouldn't drive drunk. And then kidney donations and organ donations ended up going down significantly because who donated their organs? People that are killed in car crashes, you know. And now to your point, then you take that one step further and say we're two or three years away from Waymo. What happens to an $800 billion like insurance industry? What happens to auto people that think about it. So we think all that, we think this is going to be an interesting 10 years. Not exactly sure how this is going to play out. I would just say that, you know, one thing that I do feel confident about is every, every advancement of technology. People have said this is the end of jobs. And that has never happened. You know, it has just been a little bit of a changing role.
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I'm sure you're in the mix of this because a lot of these companies that you invest in are like overlays of the core model of your anthropics and things like that. You know, we had Grok 4.0 come out and I don't know if you saw all of its testing and knowledge capabilities. It blows Chat, GPT and, and Gemini and all them out of the water. I mean, it's like, I think it's like it's, it's supposed to be the most intelligent, you know, but then OpenAI, you know, releases their next version, you know, so it's, it's this concept. But what's your thoughts on that space?
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First off is whatever tech you, you're using today will be the worst tech that you ever use. So like, if you just go in with that assumption and look, the secret to this space and a lot of this software is spectacular user experiences, you know, so we don't look at these things. We don't try to assess the best tech in the world. We are just trying to assess over some threshold that says, yeah, they know what they're doing on the tech side. What we're looking for is the best user experience. How do you feel at home with that software? How is that software talking to you as a plaintiff attorney with these specific goals? If you see that you're going to end up buying that and you're going to end up using that. Now at the same time, the tech is going to get better. So what we're looking for are the companies that can consistently be swapping out the plumbing behind the scenes. But if you said to me, am I okay with 99% accuracy or 99.6% accuracy, but the 99% fits your workflow and the 99.6, you're using a generic tool by yourself and you're not leveraging the know how and the, you know, like we're back in the companies that are waking up every day and there's 20 engineers and all they're thinking about is how can they make this software incrementally better to solve your next pain point.
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Thank you for that. I don't want to hire. That's like, look when you're choosing your CRM and it's like, I don't want a salesforce engineer.
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Yeah.
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I just want the tool to work.
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Yeah. And work in your way. Like. Yeah.
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Like.
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One of our first investments was software for venture capital funds. And it was extracting information from documents the same way you need extraction done. But the difference was all of the fields that this company had said things like does this go and fund one or fund what fund? Is this a part of that that would never exist in any of. In any file. You ever use the concept of a, like a venture fund. But for us, that's how we think. Is this the accelerator? Is this fund one? Like, where does this fit? I mentioned a company at the single event stuff that does that's Law Pro. I mentioned something at the Mass Tort that that's for pattern data. There's ones for malpractice, there's ones for all of these different sub verticals. But I think they actually all need to exist because the job is different for each one. You know, it's not the same like looking at a car accident versus looking at a, you know, a challenge with a drug manufacturer for 10,000 folks. Like, they're very different workflows. So whoever nails that workflow and makes your life a lot easier, they're the ones that start signing up the customers. And that's kind of what we're looking for.
A
Fantastic. Yeah. And I mean, I put myself in those shoes. Like I'm the same way. That's how I think of them is like the adoption rate, especially when you have a big team that you're trying to get them to adopt as well. You know, we just went through a scenario and I'll just behind the curtains it's like we were using Rank Ranger, a really great tool, very customizable. Then we went to you know, all custom looker studio, feeding in everything got and then it's like, you know, but agency analytics is here, it's been around and it's got all, all these integrations. Natural, very intuitive. And it does. Maybe it's not 95%, maybe it's 90. So that's kind of, I think the user will invest more than 90% if it's intuitive.
B
Yeah. And that's the like, hey, integrations. Are you working with Filvine? Are you working with Clio? Are you like these things, Matt, like you can press one button on this software and it just works. But that's an example of something that like, you know, the chat GPT is not going to focus on day one. You know the thing that still blows my mind is like Microsoft Word could have solved half of the legal tech out there, but they chose not to. And there's a multi billion dollar industry of people that have Word plugins and that's where a lot of attorneys live in. And that's the argument for verticalization. Hey, create a better user experience and they will come.
A
Fantastic. Zach, this has been a ton of fun. I could chop it up with you. We talked about a lot of exciting tools, you know, where can go to the people to connect with you and if they have any questions and they want to touch base, Please check out.
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Legaltech.Com we also put on an amazing event called the TLTF Summit that is designed to showcase all of this technology. Legal Tech.com is great. Look at us on LinkedIn as well and you know we'd be thrilled to say hello to anybody.
A
Yeah, and I'll be going to the summit guys, so if you're heading there, please say hi to me too. And Zach, thank you so much for coming on the show. Technology changes market shifts. What doesn't change is the need for a clear, dependable plan to bring in more cases you want. That's what we do@ Rankings IO. We help personal injury firms create sustainable, measurable growth. To learn more, visit Rankings IO. Thanks for joining me, I'm Chris Dreyer and I'll see you on the next episode.
Episode 373: Understand the Legal Tech Boom: A VC’s Guide to Winning the Future of PI w/ Zach Posner
Date: December 16, 2025
Guest: Zach Posner, Co-Founder, The Legal Tech Fund
In this episode, Chris Dreyer sits down with Zach Posner, co-founder of The Legal Tech Fund, the only venture capital fund exclusively focused on legal technology companies. The central theme is understanding the explosive growth in legal tech—dubbed the “Legal Tech Boom”—and what it means for personal injury firms seeking an edge in an ever-evolving market. The discussion flows from law firm funding models, the impact of AI, VC investment priorities, to the granular ways technology is re-shaping everything from intake to case management and even expanding practice possibilities for PI firms.
Legal Tech Catches Up:
“Historically it's been a decade behind and for the first time I think that we're like right there.” – Zach Posner [00:29]
Legal as an industry is no longer lagging a decade behind—emerging tech and AI are pushing legal into a new era of parity with other sectors.
Industry Size is Massive:
“Legal services are a crowded $1 trillion industry.” – Chris Dreyer [00:36]
The size and fragmentation of the industry means vast, untapped markets for new tech entrants.
Mindset Shift is Required:
“It's not to be afraid of AI and tech...from the pessimist side, it's like, what can it do for me from the optimist side, I think there's a lot of opportunity.” – Chris Dreyer [05:36]
Both hosts emphasize accepting and leveraging tech rather than resisting it.
Multiple Funding Routes:
“Arguably the best, and the timeless one, is bootstrapping a business. But...if you’re going to need millions dollars of infrastructure...that’s where we come in.” – Zach Posner [02:07]
Not all innovations can get off the ground bootstrapped, especially tech-centric solutions requiring upfront investment.
Venture Capital’s Role:
“A bootstrapped entrepreneur expects a very consistent path...We are expecting zero revenue and then boom, lots of revenue.” – Zach Posner [02:24]
Venture capital is for scale and explosive growth—with expectations to return multiples, not mere doubles.
Law Firms as Tech-Driven Businesses:
“Entrepreneurs that would historically go build tech companies say, you know what, we're going to try to build a law firm. That’s what Law Firm 2.0 is.” – Zach Posner [03:40]
The new wave: tech-first law firms leveraging AI to deliver services and capture markets previously inaccessible due to costs or efficiencies.
Tech Evolution: From Subscription to Transactions to Service:
Tech business models are evolving: from SaaS to per-transaction, now to handling segments of legal work itself.
Tracking the Market:
“We're tracking about 2,800 companies...getting connected to about 100 new companies every month at this stage.” – Zach Posner [05:00]
Legal tech is currently experiencing unparalleled growth, affecting all layers of the legal ecosystem.
Room for Many Winners:
“This space is big enough, you're going to see multiple winners.” – Zach Posner [09:52]
The market is so large and fragmented that several strong performers can coexist.
AI in Intake, QA, and Sentiment:
AI as a Compliance Issue:
“If you rely on this stuff too much, that can be borderline malpractice. Now I'm hearing, well, if you don't use some of this stuff, is that not?” – Zach Posner [13:11]
The expectations around tech use are shifting—from caution to it becoming potentially obligatory best practice.
Impact on Work:
AI and automation are depicted as role-changing, not job-destroying—freeing legal professionals for higher-level tasks.
Referrals and Marketplaces:
Process Serving:
Document and Intake Automation:
Case Financing and Payments:
Consumer-Facing Innovations:
From Solutions to Integration:
“The answer is not to boil the ocean and replace every[thing]. It's just like...start with one little piece here.” – Zach Posner [16:51]
Success is in incremental tech adoption and solving specific workflow steps.
The Need for Middleware and Interoperability:
The real opportunity for new startups lies in middleware—letting the expanding array of specialty legal tech tools work together [19:18].
Best Tech ≠ Best User Experience:
“We don’t look at these things...to assess the best tech in the world...what we’re looking for is the best user experience.” – Zach Posner [26:34]
Verticalization is Key:
Each legal sub-vertical has special workflows; success will come from narrowly focused, deeply integrated tools rather than “one size fits all” [28:09].
For PI firms: The future will belong to those who embrace change, adopt intelligently, and keep workflow at the center of their tech decisions.