The Evolution of the Legal-Tech space with Nick Rishwain

Made with speech-to-text software, so a few words may be off.

0:00You're listening to the Contract Heroes Podcast, your one-stop shop for all things contract management. And now here are your hosts, Marc and Pepe. Hello, everyone, and welcome to another episode of Contract Heroes, where we're not the heroes, our guests are. Uh, today, from LegalTech Live, we've got Nick Rishwain joining us. Hey, before I th- flip things over to Pepe, Nick, uh, to give us a little bit of a background on what we're gonna be chatting about today, I would love if you could just give the listeners a, a quick overview of, uh, what LegalTech Live is, and, uh, from there, we'll get things kicked off. Thanks for joining us. Yeah, thanks for having me, guys. Uh, appreciate it. Always, always enjoy, uh, meeting other podcasters in our very select, uh, uh, very niche space of legal technology. But yeah, uh, LegalTech Live, uh, was a podcast and video, uh, live streaming show that I started with a buddy back in about 2015, uh, and, uh, started off just kinda interviewing, uh, others who were in legal technology. After about 30 episodes, I think we focused more in on legal tech startups. Uh, that buddy had, uh, taken off.

1:20We, we had basically gotten involved in it 'cause we were both involved in social media pretty heavily. Uh, and live streaming had sorta taken off at the time, or it had become much more active and, and, uh, neither of us, uh, wanted to write a blog. Uh, but we were both interested in legal technology. And, uh, and so the best way to, I found, a best way to do, uh, learn more about... I was in legal technology, uh, at experts.com. Uh, had been there for five or six years at the time. Uh, and I decided I, you know, there were some exciting things happening i- in the space, or early stages with AI and blockchain and so forth, uh, and I wanted to know more about what was going on there, and I wanted to see what people were building and, and, uh, talk to people. I enjoyed talking to people. And, uh, that's pretty much how it got started. And so we've done about 130 episodes or, or something now, Hun, uh, where we've talked, uh, predominantly with legal tech founders.

2:23And, uh, and the space has been growing in that time. And we're on hiatus right now. Every once in a while I get bored and take a break. Uh, and, uh, that's, that's kinda the benefit of it, uh, being, being a hobby, uh, uh, is that, uh, I can take the time off when I want to. That's great, Nick. And I think that was one of the main things that we wanted to talk with you in these episodes. You know, like, we, we actually focus a lot on CLMs right now because we consider this, like one of the hottest, uh, legal tech tools, but we want to do this a, a little bit different. Mm-hmm. We already did it with Alex Hsu in, in couple of our other episode, and it's how have you built your own community? Because this is impressive. You've been here for seven years, and maybe this doesn't sound that much, but I would say that for legal tech, that's a lot, right? Because there was just, like recently everybody was involved in legal tech. Now, uh, I would say since three or two years ago, if you go to LinkedIn, now you can see a lot of profiles that says legal tech expert. Right. Right. Right? Yeah.

3:27And, and it's been a lot of things, and we totally agree with you that the best way to learn about this kind of market or industry is talk with other peoples. And podcasting or blogging, I think it's, like the best ways on, on, on how you can learn from the experience and the path that a lot of people have taken to do their legal career or to just, uh, quit working in the big law or as an in-house, you know? Or, uh, and I think you, you have done it great, and I would say that Nick Rishwain is, like some of these guys that everybody knows inside the legal tech. So congratulations on that, Nick. Oh, thank you. Thank you. And was there, was there a question there, Pepe? I'm not sure if I- ... I- if I caught the, what the question was. It was very, very flattering. I appreciate that. But yeah, pl- uh, was there a specific question on that? There was no specific question. There were, there was something that I wa- wanted to, uh, just, just like a little int- introduction on that.

4:24But before we start talking about on, on, on how you started with the legal tech and how was back in the days and now how you've seen it right now, uh, can you tell us a little bit on your role or on experts.com so people can know a, a little bit- Sure... about the company? Yeah. So experts.com is a, uh, marketing platform for expert witnesses and, and business consultants. So it's, uh, so if you, if legal tech is niche, uh, experts.com is also a niche. More of a l- uh, litigation support aspect, uh, of, uh, of the l- uh, of the legal industry. Probably a Web 1.0, uh, it- initially a Web 1.0 company, still a Web 2 company. Uh, and, uh, so we are, uh, it used to be what you would call a directory. We think we offer more than what a directory is, uh, today. And it's, uh, primarily for experts to market themselves, uh, to attorneys who are looking... Attorneys, businesses, industry. Um, it, it, it's really more broadly, uh, m- more broad than, than just, uh, litigation experts, but that is the primary, uh, bread and butter of the company, is, uh, marketing the expert witnesses.

5:38Uh, and attorneys can come to the site, search the site, and contact the experts directly. We, we will do, uh, a flat fee search if they need us to, if, if they don't wanna do it themselves, and, uh, been doing that for about 12 years. So I was in that, uh, in that, uh, in the industry, legal technology industry, which we were- Right... uh, you know, a sliver of. And, and in about 2015, I saw that, uh- You know, I was, I had been spending time in the industry. Uh, I'm, I'm in the Central Valley of California, which was a little more isolated. It wasn't in San Francisco. Okay. I'm about 90, about 90 minutes from San Francisco, where I saw a lot of, uh, lot of stuff was, um, taking place, and so that, that's, uh... I thought, "All right, well, how do I get to know other people who are in this industry with me?"

6:27Uh, and, uh, the podcast, uh, started as a hobby, and, and that's really what it, uh, what it has remained, uh, as a way to kind of network. And one of the best ways to network and get to know people is by, uh, promoting what they're working in, you know, what they're, or promoting what they're doing. So that's, that's sort of what I did. Yeah. And Nick, I think, you know, our, our experience has been, uh, very similar, right? You know, Pepe and I were, were, well, at least Pe- myself. Pepe's, you know, a lawyer and, and definitely played in this space a lot more than I did. But, you know, m- moving from, from, um, selling IT software and, and help desk and service desk solutions and coming into- Mm-hmm... to contract management, you know, we were kind of scratching our heads, and we, we really didn't know what, uh, what we were doing and, and figured a great way to learn and network would be to, to have people on and chat about what they're up to and what they're doing. So, um, you know, I, I think, uh, we're coming at this from a similar angle, and it's definitely remained a hobby for us as well.

7:25Uh, but I, I think the relationships that we've been able to build through the podcast have been invaluable, like you said. And, you know, with that said, I, I think we also do focus on, on similar types of guests that come on the show, you know, maybe more so when it, it comes to the, the types of folks that you're specifically interviewing, which are more the startups, right? Mm-hmm. The technology providers. With those folks that are coming on, on the show, how, how have you seen the space evolve and the technology evolve, uh, since you, you started interviewing these, these, uh, organizations and, and their leaders? Uh, so I think, uh, seeing the space evolve, you know, in 2015, I guess when I started, it was, uh, you know, I've primarily focused on, uh, SaaS products rather than, um, you know, there's, there's a lot of service-oriented, uh, companies in the legal space. Uh, but generally a service, service company is, is not as scalable as SaaS, and I, I wanted to see, uh, greatest impact. Uh, and usually the greatest way to do, to have an impact was, was scalability.

8:34Probably, you know, when I, even when I started, it was probably predominantly, certainly in the 2010s, it w- you know, legal technology felt like it was primarily e-discovery and maybe law practice management or, or case management, uh, CRM kind of, uh, tools. They were certainly the, the most notable. And it's, it's broadened significantly since then. Uh, certainly some legal research tools were, were getting some AI-based legal research tools, were getting some, uh, some attention back in 2015, 2016. Um, and, and so it's, it's, it, it's, it's broadened and narrowed, right? Uh, almost it's, there's, there's a wider variety that now include probably areas of, uh, fintech and regtech, compliance related, uh, that, that I probably consider, and now, and now justice tech or, or those access to justice types of startups, um, who are, who are, some of them are trying to have more of a direct to consumer, uh, approach.

9:48Whereas, you know, when I, when I started, it was probably, they were predominantly serving in-house and in big law and, and there's still huge value in, in creating tools that sell to those, right? Your enterprise, your enterprise level, um, tools. Uh, CLM certainly, best I can remember, uh, was not, wa- was not a phrase that was used in, in, uh, 2015. I think it was a couple more years before that really became, uh, a more, a more utilized phrase or, or even now more saturated type of phrase. Uh, but yeah, so it was e-discovery, uh, it was sites like experts.com. You know, it was fairly, fairly distributed in, in, you know, Bob Ambrogi would probably have a different take on this 'cause he's been doing, uh, legal technology for about 30 years.

10:47But, you know, uh, you're talking legal research and, and IT solutions for offices, uh, seemed to be the, the big ones, and there wasn't, uh, a very vibrant startup economy when I, or, or startup, uh, space when I started, and that seems to have changed pretty significantly. Now there are a lot more tools coming up, whether it is the, you know, manage- managing text communications between the lawyer and client. Um, their court reporting has seen some innovations. Um, legal intelligence is seeing some, some pretty significant, uh, innovations. Uh, there, there's just, there-- So more things probably fall under the AI, under the concept of legal technology and than, than they did in 2015 when I started. Probably more things fall under legal technology or it's touching, uh, legal aspects of the work. Uh, it, but, but what companies are focusing on seems to have become more, uh, narrow in, in scope.

11:54So, uh, I don't know if that's a good answer for you, but that's I guess what I've seen. Right. And that's something that we've been also discussing, uh, with other of our guests like Jason Smith and also with Eric Laughlin, the CEO of Agiloft, that back in the day These kind of softwares were trying to be classified as legal tech, right? So tools that can be used by lawyer. But right now, what they've seen and what the market have, how we have changed, is like these tools are not just for legal. They're like, uh, enterprise softwares, right? Right. Because such as CLMs, they're not tools just owned by the legal team. If they're tools that procurement needs or sales team need- Right... compliance needs, because they need some business process automations that serve to the whole company. Uh, so we need- so in these seven years that you've been doing this, uh, uh, interviews, is there any, any, any story that you can remember of, of any kind of a startup that was just starting back then and, and now they are, they- they've been keep growing? Yeah. Uh, who did, who did I interview that has kept growing pretty significantly? Mm, in the last, I don't know, three years, Trellis, uh- Oh, yeah...

13:06Trellis Law is, uh, or trellis.law is their, uh, Trellis Legal Intelligence is the name of the company, but website's trellis.law. Uh, they- they've grown pretty significantly in the last three years. They've had, I think, uh, I think they're onto a Series B now. Um, certainly in the seven years that I've been doing it, uh, Clio has grown from, from, uh, uh, I don't know where they were at when, when I had, uh, when I had known about them, but now they're, I think, beyond a Series D. They've grown significantly. Certainly Ironclad was a more recent interview I did with Jason Bomig, and, and they've just grown, uh, grown like wildfire. Uh, uh- Right. They're both new unicorns right now. Y- yeah, yeah. They're, they're the unicorns and, and that's awesome to see in legal technology because it used to be pretty rare, right? Like, we had Thomson Reuters and LexisNexis seem to be the two publicly traded.

14:06Uh, I haven't done, I haven't done an interview with LegalZoom, but they're now publicly traded, so there's been- Right... some, uh, been some pretty, uh, pretty major change, uh, pretty, pretty major advancements. Hopefully what we'll see is those companies now, the, those that are in the later stages, 'cause I generally focus, uh, focused on, uh, early stage, uh, seed, pre-seed, uh, maybe, maybe, uh, Series A. Uh, those are, have been primarily the ones that I focused on, because I wanted to talk to peop- I, I wanted to talk to the founders before they became a big deal, uh, was kinda my, that was kinda my goal. Um, so there have been several who have blown up and, and, uh, we see that in the news stories on legal tech, uh, all the time now. Uh, so which I'm hoping, uh, uh, I think, I, we may have discussed this, Pepe, that, uh, I'm kinda hoping it'd be really great if, uh, those who are now going public are also really successful when they're public, because hopefully that will allow, uh, more investment to, to come to the space.

15:19Certainly one of the harder parts, one of the reasons that investment stay, seems to stay out of legal is if you're trying to go direct to consumer or, or somehow serve, uh, those who are looking for justice, uh, accessing justice or accessing legal services, uh, regulations have made it harder. So, uh- Right... harder to accomplish that because of the unauthorized practice of law and attorney fee sharing and so forth. So, so those, those are more difficult. Hopefully regulations will one day change, uh, on that and allow for, uh, for some greater direct to consumer or, or B2C type of, uh, type of, uh, we, we've seen some successes, uh- Right... online divorce and so forth that have had, uh, some, some success, but it's a slower road if you're, if you're not selling to the enterprise. Right. And I would say that one of the good things about working with technology is that you're not limited by any country regulation, right?

16:22I mean, of course, the big ones have focused a lot on the US because it, it's, it's the biggest market- Huge market... in the world. Of course, most of those companies, they, they just don't care about going elsewhere. There, there's a lot of business there. But the good thing is that if they expand to other countries where the regulations are not as strict, right? That you need to pass a bar on every state to practice there, right? Right. And you can just go to, into another country, even if it's, uh, Europe, Latin America, Asia, right? So that's one of the, of the good things about working with technology, right? So, uh, and a- a- and one other thing that I was thinking about, so when you start building this community, right? Mm-hmm. So let's say sev- seven years ago, how did you start, uh, like looking for people to interview? Did you just, like, text them, look for companies? Was there any directory or somewhere or, or how did you learn about these new companies? Just so, I mean, I'm reading, I was reading about legal technology, right? So I was, uh, looking to see what ABA and, and Legal Rebels and Fastcase 50 and those types of things were, were reporting and what people were doing.

17:38And I, uh, you know, I even think I was using Google Alerts fairly, uh, regularly back then, although it feels inefficient to even look in that folder anymore. But it was, uh, I would, I would find somebody, uh, and I'd go over and check out their LinkedIn or their Twitter profile and connect with them, uh, and then say, "Hey, you know, I'd like to interview you about what you're building." And that, that was primarily how I did it for, uh, it's still how I do it, although a lot more people will come to me now, as I'm sure you guys e- experience now that you're, uh, I don't know how many episodes you're in, but, you know, everybody who's looking for any, you know, any press that they can get that might, might help them while they're building something, uh, they, they s- tend to start reaching out after a while. Uh, and, and that's how I did it, and then I kept promoting people. Like, uh, you know, i- if I have a superpower, which I'm not sure- ...

18:33if I have a superpower, I'm, it's probably I'm pretty good at making friends. Uh, and, uh, and I like helping others to succeed, so, uh, that, that has been how I did it. "Hey, would you like to come on the show?" And then, you know, continuously promoting what they're working on as best I can, uh, especially if they, if they kept in touch. You know, some people don't keep in touch after the interview. That's fine. They move on. Maybe their company is successful. Others who have stayed in touch and, and, and communicated and helped share the, share the show, like, you, you build a relationship with those people. And, uh, uh, and so I think that's probably the best way that I found people. Uh, I go on Twitter, follow the legal tech hashtag, uh, see if it was interesting. Uh, and I was always looking for something more unique in there, uh, and, and this'll come back to, to your, your CLM topic.

19:28But I'm generally looking for something that's a little more unique that I hadn't seen a, a thousand times, um, or that wasn't a very saturated area. I wanted somebody who had a, a really interesting idea, um, that, that m- it's probably most of these ideas are already existing. Pro- Marc, you probably have experienced this if you were in IT. Most of these services existed outside of the legal space, but we had to add legal to it, uh, in order to sell it to attorneys, uh, even though the tech is probably, you know, efficient, sufficient somewhere else. So I saw some that, uh, that were like Asanas and Trello boards and, and things like that, that, uh, you know, they did it for attorney workflow. So it's very similar, but we, we had to start it for attorneys specifically, uh, or, or legal services specifically.

20:24So, but yeah, uh, it was a long way of saying, Pepe, that, uh, that it was mostly by reading and, and, uh, and checking out, uh, Twitter and seeing what people were, were building and sharing about. That's a good strategy. And you were also last week on the Future Law Conference, right? Mm-hmm. On Stanford. Yep. Uh, well, Marc was, well, not, it's, not, well, I would say, uh, it- it's also another l- big legal tech conference, which is the Legalweek, uh, New York. But what do you think about, uh, going and getting involved in this conference, like, to, uh, to know more about technology? Yeah. I think it's great. Uh, I think attending, uh, you c- you cannot, uh, the, you cannot replace meeting people in person. You just can't replace that, I don't think, uh, for actual connections. The closest thing I've found to that was what we're doing right now, which is why I started off with live video, uh, streaming video, uh, interviews, where it was much more authentic because you're seeing each other digital eyeball to digital, digital eyeball.

21:29Uh, it's the closest thing I'd found to in-person meetings. But yeah, I try to make it, work permitting, I try to make it to a couple of conferences a year because you just really cannot beat those meeting people in person. Going to the sessions oftentimes are totally useless. Uh, I found, uh, those are, uh, very little value. I d- not at, at Future Law. I actually enjoyed the sessions at Future Law, but again, that's a little bit more, um, theoretical in nature or, or maybe more cutting edge than, than other trade association, uh, conferences. Uh, so most sessions, uh, the only ones I end up, uh, going to are if I've got a friend who's ch- who's, uh, who, who's presenting at the session. But almost all the real activity either happens, uh, where the vendors are at or in the hallways, and you can't beat being around, uh, being around people.

22:29Then eventually you've got friends in the space, and you just wanna go, you wanna go to a conference and see your friend. That's great. And any other conference that you recommend or that, that you've been involved? Yeah. So I've still never been to ABA TECHSHOW. Uh- Yeah. The one in Chicago, right? What's that? I, I, I think it's in Chicago, right? It's in Chicago. I've still never been to that one 'cause it, for work purposes, it's not really, uh, it's not really, uh, doesn't, doesn't target who our, uh, who our customers are. Um, but, uh, I do really, I, I always followed the list of the, uh, always follow their list for their Startup Alley, uh, because I always wanted to, if I saw something good on there that I wanted to interview, that, that's, you know, I would then reach out to the founders of those companies and, and see if they could be interviewed, uh, if they'd be willing to be interviewed. Uh, so ABA TECHSHOW, I think, is probably a great, uh, probably a great-... conference to attend. Hopefully, I'll attend it one year, maybe next year. Uh, Cleo's always been good. Uh, I enjoy that conference.

23:37Uh, it certainly it is more targeted to, uh, our customers or one- Right... one part of our customers, uh, which is the, the lawyers are there. So th- that is more helpful for us. Great. So Nick, before we close with this great episode, and after 12 years working in expert.com and, and, and working with legal tech, have you, do you have any tip on how to sell to a lawyer? Like, what are your best tip on this? Yeah. Uh, so the best tips on this, uh, are if you can avoid it, find somebody other than a lawyer to sell to. So- ... that would be the number one tip. Um, there's really, I mean, we can go in a lot more depth here. It's up to you guys how lo- I don't know how long you normally do this.

24:28Uh, if you can find somebody else to sell to in the, in the firm or in the company, uh, sell to them rather than to the lawyer. Uh, that would be the primary idea. The probably second idea on that is don't, don't try and get them on the phone. I would try and, uh, I would try and butter them up with, uh, you know, maybe have them on your email drip campaign, ri- and, and keep top of mind as best you can because chances are when they go, when they're gonna make a decision, uh, they're gonna do that in their time. And if, uh, if they're not in a buying mode at the time, then you're, you're wasting their time and you're just gonna make them angry, especially if you're selling to practitioners. Um, in-house, I, I anticipate is a little different, which is probably where you guys are selling.

25:22Uh, the probably, the n- the next thing that I would do i- i- what I, what I've seen be the most successful sadly, uh, I think, uh, in legal technology is that if you build right into the Microsoft ecosystem, that helps you along a l- you know. So if it's an add-in for, for Word and Outlook, that's going to make your life selling to legal communities much easier. Uh, the s- the point solutions or the standalone solutions are even harder. If, if you can build it into their existing workflow, that will help you, uh, sell to, uh, lawyers. But, but certainly, be better to find, uh, a better influencer in the, uh, or, or a better stakeholder within a firm, uh, even at the paralegal or legal assistant level who's more likely to be the ones who are using the technology. Uh, that, that would be my recommendation. Yeah.

26:20And, and Nick, I think that that's definitely something, you know, that, that we've seen, um, is even though that the lawyers are, are definitely power users of, of the tool, uh, you know, you need to get other departments involved. Um, for the most part, I... And I think this is changing, but I, you know, for the most part in the past, um, the, the law department has always been looked at as a cost center. Um, and, and they, you know, they really don't, or used to not have too, too much budget to, to work with to, to go out there and try to find tools to use. Um, so you know, we're always trying to get sales involved and procurement involved. Mm-hmm. Um, and, and I think that goes a long way too in, in showing that a lot of these tools that we call legal tech really aren't just legal tech software. Uh, you know, they're, they're more enterprise-wide. And, and if you want to succeed with these types of applications, you do need to incorporate other departments into these journeys that you're taking because that's truly how we see organizations be successful, i- is by becoming one enterprise and not looking at it as a segmented by departments. Right. And I think that's fair. I mean, uh, if the, the, if it is an enterprise-level solution. Now, of course, there's some solutions that are primarily like litigator solution, right? Or the- Yeah...

27:32transactional attorney solution. That, that's different. That's, that's pretty much strict legal tech right there. Um, but certainly, if you're building a solution that's gonna be on everybody's computer, this is again, why I say Outlook and, and, and Microsoft Word where, uh, legal assistants and others are doing it. If you're building into that workflow, it's more, more likelihood they're gonna actually u- the end user's actually gonna use your product because it's already where, where they wanna be. Yeah. Um, but yeah, if you can make it an enterprise-wide solution, you know, cybersecurity had, i- it's great for this, right? 'Cause everybody has to use that. So they've, they've got that kind of entry level, and, and they're usually working with the CTL or somebody like, somebody to that effect. So, uh, but if it's gonna be installed on every computer, uh, you know, that, that is definitely better. Uh, a lot of legal technology can be very segmented.

28:30Uh, and if you can avoid that, if you can make it, look, this is an editing specific tool for the legal community, and build that right into their existing, uh, workflow, y- y- you know, you stand a much better chance than, than somebody else, than, than another, uh, another startup in the space. Yeah. Yeah. I, I definitely agree with that. Uh, well, Nick, this is, hey, this has been, uh, a great conversation. It's always a pleasure to meet, uh, somebody else that's doing this, been doing this a, a bit longer than we have and, and be able to learn from them. And hopefully, our audience has some takeaways here. Uh, if folks wanna check out, you know, the show, uh, where's the, the best place to, to do that at? Oh, yeah. Uh, Apple Podcasts, uh, Spotify podcasts, legaltechlive.com. Uh, they can check it on, on any of those, uh, whichever one you, whichever one you prefer. If you like watching, the videos are on the website.

29:25If you want the unedited, uh, unscripted, that's, the full interviews are there. So you can check it on YouTube as well. Uh, but yeah, LegalTech Live or on Twitter @LegalTechLive. Great. Fantastic. And we'll, we'll make sure folks that those are in the show notes as well so you can check those out. Well, Nick, we appreciate you coming on. Thanks everybody for listening to another episode of Contract Heroes, and we hope to have you here, back here real soon. Thank you. Thank you, Nick. Thanks, guys.