Ep 250: CEO Ross Guberman On How BriefCatch Is Expanding Its Mission to Help Legal Professionals Improve their Writing

Ross Guberman
We want to be a sort of one stop shop for everything related to legal writing, not just improving documents, not just enhancing documents, not just fixing documents, but generating documents, getting models of paragraphs or provisions, having all the pedagogical, educational training content that I own, that I've written in there too, really would be sort of cradle to grave for law students on up through the career trajectory. It'd be kind of a one stop shop for all the above.

Bob Ambrogi
Today on Ross Guberman, the founder and CEO of Briefcatch software to improve your legal writing it's been a notable year for Briefcatch, starting with its raise nine months ago of a $3.5 million seed round, its launch of new products and features, and its formation of a legal writing advisory panel of judges, advocates, and academics. Culminating the year was Briefcatch's announcement last week of its hires of three legal tech veterans into key executive roles in marketing, sales, and product management, all to help lead the company into its next stage of growth and development, which will include the launch of a suite of AI enabled products. Founder Guberman is my guest today to discuss the company's history, growth, recent news and future plans.

A former practicing lawyer, he was a legal writing coach and speaker when he conceived a brief catch, which he formally launched in 2018.

This is Bob Ambrogi, and you're listening to Law next, the podcast that features the innovators and entrepreneurs who are driving what's next in law.

Before we get to that conversation, please take this moment to learn about the sponsors whose generosity supports this podcast.

Don't waste your time and resources on generic law practice management software. Choose Meriscase, the ultimate law practice management software built exclusively for workers compensation, employment and labor and insurance defense firms. With extensive features like document management, time tracking, billing, and reconciling online payments, meriscase provides tailored solutions to support your firm's success.

See how firms are reducing their administrative workload@maristcase.com. dot one more thing before we get to today's episode, I have a favor to ask. If you enjoy law next, please take a moment to leave us a review on Apple Podcasts or wherever you listen to the show. Your reviews help others hear about us, and we appreciate it.

Now on to today's conversation.

Ross, welcome to Lawnext.

Ross Guberman
Great to see you, and thanks for having me.

Bob Ambrogi
So I learned something I never knew about you today, and I've known you for quite a bit now. But in reading up on your background in preparation for today's talk, I don't think I ever knew that you were a journalist before you got into all the law business stuff that you're doing?

Ross Guberman
Yeah, it's kind of, it was kind of a funny detour, actually, after I was an associate and before I got into training in tech, worked as a kind of investigative reporter for, for a time and got, got a lot out of it. I think you might have a little bit of journalism background, too, if I remember correctly.

Bob Ambrogi
Well, I keep trying to keep plug, plug away at it a little bit, but, you know, I did not know that. I didn't realize it was after you were already a lawyer. I was assuming it must have been before you went to law school. But was it just your interest in writing or what brought about that detour?

Ross Guberman
Well, you know, like I said, it was after I was an associate, and I was sort of trying to find my, find my way, and I did a number of things, and this one just sort of, kind of fell in my lap. There was a, a really, really interesting story in the DC area about a lawyer who accidentally killed someone while driving, and there were all sorts of interesting dimensions. And I ended up getting a deal with the washingtonian magazine to write about it, and it was a big piece. Got optioned for tv rights, and I had a blast. So I kept up with that for about a year and a half or so before moving on to more serious, serious matters.

Bob Ambrogi
Well, it's pretty serious stuff.

I guess the legal world is fortunate that you moved on from journalism into other endeavors.

Ross Guberman
It's good training, though.

Bob Ambrogi
Yeah, I would think it's very good training. And it's interesting to me only because I know that a lot of journalists end up going to law school after working for a time as journalists. And I've also, over the course of my career, met a number of lawyers who went into journalism after having been a lawyer. And there certainly are a lot of parallels between the two professions and in the work that you do. And, you know, it's, it's, you know, kind of often comes down to gathering facts and synthesizing facts and being able to present a good story around those facts. Very similar kind of work.

Ross Guberman
Yeah, it's such a great point because I think it's one reason I appreciate the struggle people have when they try to try to take complex legal matters and put them into a narrative form, because I had the same problem putting these stories together where you just have so many snippets and factoids, and it actually is quite challenging to make them congeal into something streamlined and coherent.

Bob Ambrogi
We're here today to talk mostly about Briefcatch, but I know you're also the president of legal writing pro and the founder of Briefcatch. I think legal writing pro came first, if I have that right. I mean, how did you kind of get into this whole area of coaching lawyers around legal writing?

Ross Guberman
So also a little bit happenstance, a little bit like the journalism work. So I also, in order to make some actual money, as you know, journalism doesn't really pay. So to make some actual money, I edited appellate briefs for a firm here in DC, kind of an early, early on, remote arrangement. And at one point, the main partner I worked for at the firm asked me if I would just put together kind of a casual weekend CLe on brief writing for the associates. And of course I said yes, because she was giving me all this great editing work. And I went and did it. And next thing you knew, I had this big, big training business. So it wasn't even really my idea. I have to give all the credit to this partner.

Bob Ambrogi
So the business expanded from the firm where you were working into training. Training across firms.

Ross Guberman
Yeah, I mean, it was. You know, I started. I kind of started with summer associates because I was also teaching at a law school, so that was a good fit. And then I kind of went up the ranks, new associates, real regular associates of different practice areas. And I started doing work with judges and the courts and the circuit courts and. Yeah, then it just sort of mushroomed from there.

Bob Ambrogi
Yeah.

Isn't law school supposed to teach us how to write well?

Ross Guberman
Well, that was always something, you know, that I had to worry about. Right. People would say, you know, why the heck do I need writing training?

Why do I need coaching? Even back then, many associates didn't think the partners should be messing with their pros. But actually, if you frame it the right way, and I feel like I did, and make it more aspirational, instead of making people feel like they're getting some sort of remedial instruction. But at the same time, I think the profession seems to have agreed that for whatever reason, law school is not churning out young lawyers with super strong writing skills.

So I had that a little bit as a tailwind.

Bob Ambrogi
I know that. Again, going back to that conversation about journalists becoming lawyers, from the journalists I've talked to who have become lawyers, there's this feeling that law school actually corrupts your ability to write well, or at least to write clearly and concisely.

Do you think that's true?

Ross Guberman
You know, I have to. I know it's very unfashionable to defend law schools, but I actually do not think that's true. I think that writing well as a lawyer is very difficult, and I think that the standard. The standard, the stakes are different from what they are in journalism, for example, or other backgrounds people come to law school with, from poli Sci, you know, what have you. I think it's easy to kind of blame the law school experience or the legal writing course in particular, but I really don't. I have never seen any evidence that any reputable law school LRW program is teaching students to write in a convoluted, unclear way. Maybe they're not doing a good enough job doing the opposite. But it's kind of a myth that there are these legal writing experts out there, or professors out there, though, who are trying to make things worse.

Bob Ambrogi
Yeah, well, you know, part of it is maybe just the stuff like having to, like, repeat everything in a parenthetical or, you know, just some of the conventions of legal writing, I think that make it seem more clumsier or awkward than other kinds of writing.

Ross Guberman
Well, that I think that you might be onto something. So perhaps the biggest influence on law students writing is not the LRW class, but all the crap you have to read for three years, which is not chosen, as, you know, for its writing prowess. Right. It's chosen because doctrinally it's an important case. So that might be the real culprit is the past or the profession's writing style itself.

Bob Ambrogi
Yeah. So are you now?

We'll get to briefcatch, but now that you've founded Briefcatch, and Briefcatch is obviously growing, and we'll be talking about that. But are you still doing the coaching and the teaching and all of that around writing?

Ross Guberman
We definitely offer it to some briefcatch from the bigger briefcatch clients. I did a program for about 150 district court judges, federal district court judges, a couple weeks ago. I'm not going to turn that down, of course, something like that. But legal tech, as you well know, it's sort of all consuming and takes up a lot of your energies and thoughts and passions. So there's just no, like, physically, it's not possible for me to do workshops, but not that many years ago, I was doing 200 plus a year, and during a day, I was bored. During the pandemic, I counted up. I ended up doing 2850 workshops back in the day. So I think that's probably enough.

Bob Ambrogi
Yeah, that sounds like a lot. When you do these workshops, is there one big, overarching kind of lesson for legal professionals about effective writing. Is there one top secret that you share about how to be a better legal writer?

Ross Guberman
So the one thing that really has driven my whole career, I'd say, is the idea that there's a group of outstanding legal and judicial writers out there. People generally agree on the names. The whole secret is to figure out exactly what they do differently at the word level and beyond from the average lawyer or judge. And that's something I've stuck to from the early days. And I think it's one reason I don't get a lot of resistance, because people like that idea that it's empirical, and they like that idea that, hey, there is a gold standard out there. It's not all subjective. And my job as the so called expert is to help people figure out, practically how to get closer to the Scalias and Kagans. So that's what I would say is the secret, if there is one. And then to the extent that there is one kind of maybe lack or failing in the way legal writing is conceived in law school, it's probably that, right? There's not enough attention on this idea that there really is outstanding writing out there, and you can figure out how to mirror it or mimic it.

Bob Ambrogi
So that sounds like the genesis of brief catch. I mean, that idea that there is an empirical basis for how to write well and effectively in the legal space, and load that all up into some.

Ross Guberman
Technology and make it available 100%, so. Exactly. It's like a repository for all the lessons and little tips that I picked up on and imparted over the years. And because it is technology, it's easier to enhance and improve the underlying data set than it was back in the day when I was writing books and delivering workshops. Right. It wasn't as systematic back then. So we're able to really, as the days and weeks and months go on, we're able to really, really dig in deep into this question of what exactly happens in great legal writing and a.

Bob Ambrogi
Lot of that work you have done yourself. I mean, I remember having a conversation with you a couple of years ago. I think it was when you came out with the version three, I think, of brief catch, and we were on a Zoom call. It might have been sold during COVID or something, and you were sharing your screen, showing me the spreadsheet that you, I think you personally had pretty much compiled of all of these empirical, you know, bits and pieces of tidbits of evidence about what makes or breaks legal writing.

Ross Guberman
Yeah. And it's funny, I remember that, and I can see the spreadsheet in my mind's eye right now. And, you know, I'm sure this is true. I know this is true of other legal tech founders, too, is we don't want to think about all the struggles we had before these chat, GPT, and other tools were around that could have made all that work a million times faster, but too late now. So the answer is yes. I did kind of manually do a lot of analysis early on. I don't want to make it sound too much of a struggle, like walking up the snow to school in both directions, but I did, of course, have some data, data tools. But right now is kind of the golden age of data analysis. So things have really, really changed and gotten much more efficient.

Bob Ambrogi
So the spreadsheet is gone off onto a storage drive somewhere or something, or not an active component of the product anymore.

Ross Guberman
Yes. Yeah. Like a sort of mini museum, I guess, of struggles past.

Bob Ambrogi
Yeah. So if I have it right, you founded Briefcatch in 2018. I mean, how did you actually go about founding it? I mean, why? Why did you go from being, you know, a coach to being a legal tech CEO?

Ross Guberman
So there was actually an intermediate step where I wanted to kind of dip my toe in the water. So I probably around 2017 that I was hearing a lot of my travels about clms and e discovery. I mean, you would know much better than I would what companies were big back then, but I just remember hearing a lot more about tech suddenly. And then I was also noticing that a lot of the people who read my books or came to my workshops would ask about consolidating all these tips, or how do I remember everything? So I decided just with the very small company I had, I had one guy who's really good at coding who worked for me, so we actually made a kind of prototype for contracts called contract catch. That's kind of the genesis of briefcatch's name. You know, it was okay. I'd give it, like, a b minus. Even though I'm the one who made it, it was okay. But it was definitely a confidence booster in the sense that I saw, hey, you know, if I hire the right people, I can probably pull this off. Then I ended up doing more of an exhaustive search to find a great developer, and that's when briefcatch was sort of born. So, yeah, I think you kind of need that first project, just even if it's not that great, just to reassure yourself that it's possible.

Bob Ambrogi
Yeah. And why did you want to take kind of the work that you were doing the work you're doing, the coach, the lessons you were learning, and put that into a technology product. I mean, what did you see as the need out there or the opportunity out there?

Ross Guberman
I could see how hard it was, even for incredibly talented, ambitious lawyers and judges to, you know, kind of take all the things they might want to do in writing or the kinds of things that I would share that, you know, like a Roberts would do or Clement would do. And the question was always, okay, this is awesome, but how the heck do I do all this while I have deadlines and dockets? So the idea that you could take all those learnings and make them really easy to access was pretty exciting to me. I also felt like, given that I'd done the workshop and book business for a while, that it would be a good way for me to kind of consolidate my own learnings and my own analysis, too. So, yeah, and then it's also, like, frankly, really exciting. It's, like, really fun to be part of. I mean, obviously, this was before the AI revolution, but even back then, it was quite exciting to see this process where I'd have some half baked idea and I would try to explain it, and then the coders come in and they try to make it happen, and then you go back and forth. It's really quite, you know, I don't want to say it's exciting and stimulating 24 hours a day, but it is. It is actually really fun and challenging to get into tech, maybe even. Especially when you don't have a tech background.

Bob Ambrogi
So here we are 15 minutes into our conversation, and I've never yet asked you, what is Briefcatch? How do you describe it to people who maybe haven't heard of it or aren't that familiar with the product.

Ross Guberman
So briefcatch lets you, at any point in the writing process, just click a button and have all sorts of words, phrases, and sentences flagged with suggestions. So the suggestions can be anything from this looks like a blue book citation.

It's misformatted. This is actually the right abbreviation for the party.

Up to things like, you've used this transition many times, maybe you want to try this one and be more precise. Or here's a more interesting verb. So going back to this idea that there are so many different issues to spot in writing, all the way from kind of spelling up to higher level flow and elegance challenges, the idea is you can get not just all these opportunities flagged, but suggestions, like a menu of suggestions to choose from. And then in the current version, we also have examples from big names in the profession. So you can see exactly how they did whatever the software is suggesting. So it's a little bit like Grammarly and the way it feels, right? So you have the UI and you have the menu, you have the suggestions. If you click on something, it's made for you and track changes, but it's obviously very much tailored to our professional.

Bob Ambrogi
A little bit like Grammarly. But for legal, there are other products out there. For legal, there is a product word rake that some people might know. You differentiate yourself from that product?

Ross Guberman
Well, we have multiple suggestions. So, for example, we flag something like indicate or indicated. You're going to see show, signal, suggest, states, say. And then it will also look at the context of the sentence in our own kind of underlying data analysis to put those in an order that makes sense given the sentence. So we have that. We have also, we have an incredibly broad array of flags. So again, everything from, you know, de minimis spelled incorrectly all the way up to this particular sentence. Analyzing case law could be more streamlined and more focused if you did x, y, z. And then I'd say the third thing is this idea that you have explanations of what's going on. So you're not just expected to take someone's word for it. And then these examples. Right? So you might, maybe someone says, hey, why don't you start a sense with even so. And you thought, wow, can you do that? And then you see, well, Scalia did it, right, Kagan did it, Paul Clement did it. So that's another unique benefit.

Bob Ambrogi
Right? And all this happens right in word or now in outlook, also right in word.

Ross Guberman
And then we now have an outlook version because one of the most common requests we've gotten from our users is, hey, emails are hot now for substantive legal analysis. They're not just for setting up lunches like they used to be. So people want to be able to edit their emails without having to copy and paste them into a word document.

Bob Ambrogi
You have told me in the past that among your customers are at least some of the people sitting on the bench at the US Supreme Court. I don't know if you're going to name names there. Probably not. But who are your customers generally?

Ross Guberman
Well, yeah, I mean, I won't confirm or deny what you just said. We definitely have a lot of prominent judges and justices all over the country.

Bob Ambrogi
I think it says it on your website somewhere.

Ross Guberman
So you can, it could be not going to beat you on that one. Yeah, we have a lot of prominent judges.

I'm like pleasantly surprised, frankly, how easy it's been to sell to the courts, sometimes easier, frankly, than selling to law firms. So we have lots and lots of courts, mostly in the United States, but definitely some abroad as well.

And then on the lawyer front, we have some of the absolute biggest firms, you know, Latham Whiton case all the way down to two, three, four person firms. And then we have a lot of individual users. And then maybe a little bit, because I live in Washington and have a good history with the federal government, with training. We have a lot of government, DOJ, SEc and the like, and then a smattering of law schools.

Bob Ambrogi
As I said in the introduction, this has been an eventful year for Briefcatch, starting with its raise of a $3.5 million seed round nine months ago and culminating in its announcement last week of three key executive hires to lead its sales, marketing and product development.

In just a moment, ill ask Ross Guberman about all of that. But first, please take this opportunity to learn about the sponsors who so generously support this podcast.

Simplify payment processing for your law firm with the seamless and compliant payments processor built right into Mira's case. Accept online payments effortlessly with the same system you use to handle your workers compensation, employment and labor or insurance defense cases. Stop dealing with exhaustive processes and start accepting online payments. Discover how meritscase can enhance your practice and streamline your payment workflows@meriscase.com.

welcome back. My guest today, Ross Guberman, has big plans for Briefcatch, the company he founded in 2018, to help lawyers improve their writing.

Those plans include new features and new products, including AI driven products, to help legal professionals communicate more effectively. As we return to our conversation, we talk about where the company is today and its plans for the future. Let's get back to that.

Ross, as I said at the outset, you announced some news this week. But even leading up to that, maybe before we even get to that, you've had an eventful year or two years, really. I mean, in my mind, maybe it goes back to 2022, because that is when you came out with the latest version of your software and expanded it to compatibility with Max, if I recall correctly. Then last year, almost just about a year ago, you raised a seed round three and a half million dollars after having bootstrapped this company up until that point and talked about why you did that and what it might mean. So just for the benefit of our listeners, why did you want to raise that, that money after having bootstrapped the company? And what were some of the plans, and what are some of the plans now in terms of how you're investing.

Ross Guberman
That, yeah, it's a huge decision for a founder whether to remain bootstrapped or to seek funding, and you do the best you can. But I will say one thing. Once you get on that fundraise train, it's hard to stop.

It's exciting and it's fast moving. And I would guess there aren't that many people who end up being offered funding and then at the last minute turn it down and decide to go back to being bootstrapped. Because, as you know, since you're the one who like, publicizes these things, you have the big celebratory press release, but it's really, really hard to get funding. It's very time consuming, and nobody talks about that part. So as far as the decision, I could have stayed as is right, as you say, we were doing very well bootstrapped, but especially with what's going on in AI and just the nature of that, the client base that we just discussed, and we have a lot of constituencies with a lot of requests and, you know, a lot of requests on the, on the micro front. Like, can you have this rule, that rule, a lot of big ambitious requests. It just wasn't really possible. I mean, I had a choice. I could have had a very nice life just kind of coasting and continuing to sell the product with a very small team, or I could go big. So now I could have gone really big and taken a lot more money. So I guess I picked, you know, the porridge temperature in the middle so.

Bob Ambrogi
The, there's still time to take more.

Ross Guberman
That's right. Oh, believe me, people, you know, that's the thing. It's, you always get what you don't want, right? So as soon as you get funding, then everybody wants to give you money the next day and you have to kind of fend people off. So, you know, the basic vision was to have in the product roadmap to have lots of different variations on briefcats for patents and for contracts and for non native speakers and for the British and for the Canadians, that was the thrust on the product roadmap, but also, of course, to have AI products. And then on the sales and marketing front, I had really, frankly, done nothing. You know, we had one sales rep for a little while at that point, no marketing budget. So that was another big piece of the proposal for the fundraise.

Bob Ambrogi
So all of that ties into the news that you announced as this episode is airing. You will have announced it a couple of days ago. Do you want to sum it up for us, or do you want me to sum it up for you? But you announced some key hires. Why don't you tell us about that?

Ross Guberman
I'm really excited, and I think you're the first to hear about this. So, yeah, I mean, we had three unbelievable hires, all starting very recently.

So we have Lydia as our CMO has just an absolutely incredible background. Thompson, Reuters, Lex Mackinaw. Just like all around Rockstar and awesome person. And we're having a lot of fun already, even though we're on opposite coast. I'll see her live, I think, next week. So we have Lydia.

Bob Ambrogi
I've known Lydia for a number of years, and she's great. So that's a great hire.

Ross Guberman
Yeah, I remember that. And yeah, she speaks fondly of you, too. Then we got Darren, who actually used to work with Lydia. So Darren also comes from Lex Machina, where he was pretty widely considered, I heard, multiple times, perhaps like the greatest legal tech salesperson in the country, or one of them. He just started in the last week, but he's knocking it out of the park already, as you would expect. And then we also have Kyle, Kyle Barr, who actually, going back to our earlier conversation, had me when he was a summer associate at White and case. So the years, you know, it's kind of funny. It's like full circle now. The years have gone on. We're both a little older now.

So Kyle is kind of a jack of all trades. I mean, he was a big law. He clerked for a district court judge, a couple big law tours of duty, and then he became kind of a legal officer, legal ops pro. So he's kind of leading up our new AI products. So, yeah, we have all three of them new to the company. It's a nice burst of energy.

Bob Ambrogi
Something else that you did over the last year was to announce the launch of two months ago. Where am I? It's May, the launch of a legal writing advisory panel.

What does that mean for briefcatch and for the customers?

Ross Guberman
Yeah, that's also a lot of fun. And I think, I think or hope something that will really benefit the profession. So it kind of goes back to our earlier discussion of being empirical. So what I did is I assembled, as you said, 35 of the biggest names in writing. So big name lawyers and judges alike, especially retired judges. What we're doing is we're about. Actually, we're about to start one of these surveys. I'm going to essentially let them weigh in on all the major writing controversies anonymously, but as a group. And then I'm going to share the aggregate results with the public, including law, the law schools, all the way up to profession. So we're going to have, for the first time, kind of an official. You know, it won't have any power. It won't be like the academie francaise in France telling people what words they can use, but it will have, I think, a lot of influence because of the breadth and depth of the people in my panel. So we're going to do that, and then we're also going to have a sort of, like we're doing now a series of interviews with me or podcasts where I'm going to have some of these big names go through a section of a recent brief or a recent opinion.

We're going to analyze it together and hopefully impart all sorts of tips to the audience.

Bob Ambrogi
Interesting. That'll be good.

As you say, you've just had these three hires, and one of them you mentioned is Kyle, who's going to be in charge of new product development, I guess, and particularly AI product development.

How do you see Briefcatch as incorporating AI into its products?

Ross Guberman
So we have kind of our first AI product called client catch, which generates client alerts based on input. So that was our first step on the AI.

Bob Ambrogi
It's kind of in a beta right now, right? Is that.

Ross Guberman
Yeah, you know, people like me want things to be in beta forever, but, yeah, so, yeah, it's been in beta for, you know, it's been beta for a couple months now.

But, you know, we're getting a lot of interest from law firm partners, but also from this, the marketing departments of big law firms who have to deal with hundreds of these alerts and want to try to distinguish their firm from the rest. So that that's kind of.

Bob Ambrogi
How does that generate, how does that generate alerts?

What kinds of alerts? Or where does it draw from to do that?

Ross Guberman
Yeah, so what we'd let people do is upload the source material. So let's say there's a new proposed regulation or a new case or something from the SEC. So you upload it. You don't need to say anything about it. You just upload it. And then you type a couple of words about your audience. So, you know, publicly traded companies concerned about regulation of ESG, whatever it is, and then it will actually take all that plus, you know, the secret sauce, the magic, and the actual assistant, and then it generates a client alert with, you know, like the catchy, the catchy headline and the, you know, the next steps and things to look for in the form that law firms tend to, tend to use.

Bob Ambrogi
Yeah. Oh, interesting. I kind of cut you off, but what else? Are there other products that you're looking at or other ways that you're looking at incorporating genai into your lineup?

Ross Guberman
100%. So we're also about to launch a product that will let people ask pretty much any imaginable question related to legal writing, like grammar questions, formatting questions, strategy questions, and, you know, kind of one of these carefully controlled chat bots. So the answer they'll get, though, comes 100% of the time from me. So it's never, like, hallucinating. It's not searching the web. It's always from something that I've written about or something that I've endorsed or podcast transcript. So that's coming out. And then a really ambitious project or product, I should say. It's a project and a product. I'll just describe it generally for now. So we're like, the next level with, with writing is, you know, even beyond what briefcatch already does, is to really look at the entire section, the entire document, and get into structure and organization and logic and flow and give tips on all that. So, you know, with all the latest AI tools, we're already delving into that very ambitious project.

Bob Ambrogi
Yeah, I'm curious. I mean, you're probably giving your background somewhat of a perfectionist around writing. I can sometimes be try to be somewhat of a perfectionist around my own writing, and some of my experiments with generative AI to create content haven't been all that thrilled with what I've gotten out of it. I mean, it's good, it's fine, but it's not me. It's not something I'd want to publish under my name or put up on my blog or something like that.

So, I mean, what's your experience around that?

Do you think that this is really going to become a significant tool in terms of helping to either generate content for lawyers or help improve content that lawyers themselves generate?

Ross Guberman
Yeah, I mean, it's a fascinating question, and I think in any one day I might answer the question differently, depending on the hour, based on whatever I'm doing. To your larger point, I would say that there was a lot of exuberance a few months ago about the idea that it can kind of imitate your style. Right. So you would upload your blog posts, or I would upload my Twitter. Twitter post. Sorry, x posts. These are called no. And then it would be able to imitate your style. So that isn't really, really happening. Right. Like, it's not really able to imitate people's styles. Now, I will say, though, I've had a lot of luck. I've even done this publicly, like with these judges a couple weeks ago. I'll take something, I'll say write it in the style of Justice Scalia. So somebody really famous with a large body of writing out there, I've noticed it does a better job than it does in general. So that's probably like still a work in progress. Now, where I think the profession is underrating AI, though, even if this goes against my interests, I'll say it anyway. Where I think the profession is underrating AI is in its ability to simply take kind of average rambling pros and tighten it up. I think that in that respect, it's usually quite incredible. So if you don't, if you don't really need to make sure that all the edits are good and you don't need to know why the edits are being made, 95% of the time is going to give you a better version than you input it. So for many people, including, especially, you know, students and, you know, high school students, middle school students, of course, that's more than enough.

Bob Ambrogi
Yeah.

Ross Guberman
Yeah.

Bob Ambrogi
Do you foresee the day when generative AI puts you out of business?

I mean, you know, right now, brief catch is more of, more essentially a line by line editor in a sense. I mean, it's going to, it's going to make very specific suggestions about changing phrasing or words or whatever else, whereas Genai tends to be a press a button and you got a whole new block of text there.

Is that the future of legal editing?

Ross Guberman
So because we're harnessing all the power of Claude and Chachi PT 40 and the like, the answer is no. Now, if we were not, if we were just trying to put our heads in the sand and say we're just going to keep on going like we have been, I'd say I'd be concerned. Right. So the best, the best marriage is the power, the kind of the engine of these generative AI tools, which is mind boggling, the power that they have with all the subject matter, expertise and guidance that, you know, that I, my team are trying to provide. So I don't think you, especially in the legal profession, you're never going to have just the first right. People are not going to have chat, GPT, decide strategy, or even like, what causes of action to have in a complaint. They're not ever going to do that, nor should they. So you need the two, though. You definitely need the two. So the legal tech people also need to harness these tools, I think, to be, to remain relevant.

Bob Ambrogi
So now that you're building out your staff, you're bringing in some money, you're looking ahead to incorporating generative AI. How do you see your company evolving over the next five years or so?

What's briefcatch look like down the road a bit?

Ross Guberman
So we want to be a sort of one stop shop for everything related to legal writing. So not just improving documents, not just enhancing documents, not just fixing documents, but generating documents, getting models of paragraphs or provisions, having all the kind of pedagogical, educational training content that I, that I own, that I've written in there, too. So it really would be sort of cradle to grave, you know, for law students on up through the career trajectory. It'd be kind of a one stop shop for all the above, which is a pretty grand ambition, but doable because we're already working toward that. Never as fast as I would like, but we're working toward that. And one thing I'm lucky about is, again, I have a lot of content already. It's already there.

We're just trying to figure out the best ways to integrate it into technology.

Bob Ambrogi
Right. And although the company's name is brief catch, there's absolutely no reason to limit the application of the product to briefs. It applies to all sorts of legal writing. Does it even extend back to contract catch? I mean, is this a tool now, or do you see this becoming a tool for helping to improve contract drafting as well?

Ross Guberman
So, yeah, so I can tell you that one big, big thing on the product roadmap, which will happen soon, is there'll be a drop down menu that will ask you. It will already by then know whether it's a contract. You won't have to say, but just in case you want to put it in, it will ask you those kinds of things, and then the rule sets will be adjusted accordingly. So it's kind of funny because, you know, I made these kinds of mistakes in my workshop business, too. You make a decision, like, I don't remember exactly when I decided to call it brief catch, but it wasn't something I pondered, you know, just seemed like I did. Contract catch. Why not brief catch?

But as you say, it's. Although a lot of people think it's only for briefs.

Not true. People use it for all sorts of documents, including non legal documents.

Bob Ambrogi
Yeah. Well, I've been plastering you with questions for the last 45 minutes. Is there anything else that you would like to say about the company that I haven't asked you about or about yourself?

Ross Guberman
Well, I mean, I'd say that this really is kind of a thrilling time, I think, for legal tech founders or really anyone in legal tech. I also sense, certainly in many ways, day to day, that there's a lot of anxiety in the profession, you know, with our, with our clients, with our prospects. So, yeah, I mean, I feel, I feel lucky to be a part of all this. But I also realize that when you or I think about five years down the road, or frankly, five months down the road, there's still a lot of unknown. We just don't know. We don't know what's going to be next. We don't know what, how these products are going to evolve. We don't know what's going to happen with legal tech companies. So, yeah, I mean, it's, that's what I'd say is it's, you know, I definitely am exhausted sometimes and I definitely need to sleep a lot more. But this is, this is a heck of a heck of a lot of fun. And I'm, you know, really, really happy to be part of it.

Bob Ambrogi
See, if I'd written out this interview in advance, a briefcatch might have told me I wasn't plastering you with questions, but peppering you with questions. I don't know. We're plastering you with questions. That's a very not a good image right now. Well, Ross, congratulations on all of the stuff that's been happening and especially on the recent news and these hires. It looks like a great team of people and appreciate so much you're taking the time to share all this with me today.

Ross Guberman
Well, thanks so much. I love the questions and thanks for all you do to keep the rest of us in line and to let us know all the latest gossip on legal tech. We all appreciate it. I think the profession as a whole does, too.

Bob Ambrogi
Thanks.

Big thanks to Ross Guberman for joining me today to talk about Briefcatch. And congratulations to all three of the executives who joined the company last week.

I hope you enjoyed the conversation. If you'd like to share your own thoughts or comments on today's show, please do so by messaging us on LinkedIn or X or wherever you find us online or email me directly, ambrosiamail.com.

and if you're a fan of Lawnext, please leave us a review wherever you get your podcasts.

Lawnext is a production of law. Next media I'm your host, Bob Ambrogi. I hope you'll join us again next time for another episode of Law. Next.

Ep 250: CEO Ross Guberman On How BriefCatch Is Expanding Its Mission to Help Legal Professionals Improve their Writing

Primary Topic

Episode Summary

Main Takeaways

Episode Chapters

1: Introduction

2: Background and Development

3: BriefCatch’s Evolution

4: Future Plans

Actionable Advice

About This Episode

People

Companies

Books

Guest Name(s):

Content Warnings:

Transcript