Podcast Highlights: The Culture and Founding of Lawmatics | Legal Mastermind

Lawmatics CEO Matt Spiegel recently joined the Legal Mastermind Podcast, hosted by Ryan Klein and Chase Williams. They discussed the history and culture of Lawmatics, and the everyday legal problems that led to its founding.

The founder's journey

Matt’s arc from practicing criminal defense attorney to serial legal tech entrepreneur is an unusual one. He dives into how his experiences have led him to founding the #1 CRM and automation platform for law firms, including:

• How a bar complaint led to Matt becoming an entrepreneur
• His path from MyCase, to venturing outside legal tech, to Lawmatics

Inside Lawmatics

Ryan and Chase ask about the things that make Lawmatics stand out from the pack. 

• The values and culture that make Lawmatics one of the best places to work
• Growth goals for Lawmatics this year

Stay tuned for some insights on how technology like AI and predictive analytics will shape the legal landscape. Listen to the audio player above, or read the transcript below.

Podcast transcript

Matt Spiegel:

Our culture is everything to us. One of the things that we've been very fortunate is everyone's getting rid of offices, we just moved from 4,000 square feet to 12,500 square feet. We more than tripled the size of our office because people are coming in. We have this amazing culture. That's the part that I'm most proud of. It's what makes me get up every day is the team that we've built.

Speaker 2:

You're listening to the Legal Mastermind podcast with your host, Ryan Klein and Chase Williams, the go-to podcast for learning from the experts in the legal community about effective ways to grow and manage your law firm

Chase Williams:

Today, on the Legal Mastermind podcast, we have Matt Spiegel. He's the founder and CEO of Lawmatics. He actually founded another company you might be familiar with called My Case and back in the day he started off as a lawyer and so there's lots to talk about today, Matt. So welcome to the Legal Mastermind podcast.

Matt Spiegel:

Yeah, thank you guys for having me. Super excited for the conversation today.

Chase Williams:

For sure. And we were riffing so hard beforehand just about one, how your experience was wake surfing for the first time with the CEO of Clio and how fun that was. And then just started talking about you were a lawyer and you found a need, I assume for your firm, which we'll talk about in a minute. And then you started my case and then you're one of the few entrepreneurs that I've ever spoken to that's found two successful tech companies or SaaS products. That's where I guess the sexy slogan would be for what you guys do.

Matt Spiegel:

I guess. Yeah.

Chase Williams:

So how did that story start? I mean, you graduated law school and then worked for an attorney's office for a couple years and then started your own firm. So take us from starting the firm to your first-

Matt Spiegel:

That's right. I mean, I guess it goes back earlier than that too because I don't really think I ever wanted to be a lawyer if I really think about it. I think I just wanted to own a business and I guess somewhere in my... Well, parents actually made me go to law school. This is my senior year of college and I'm getting ready to go on spring break. I'm sitting at home and I'm leaving the next day for this awesome spring break trip senior year, which is the most epic year. And they're like, we don't want you to go into real estate. You need to go to law school. And that was literally the first I ever thought about it. And this was March of my senior year of college. And so I kind of shotgun took the LSAT and then went to law school.

So it's not like I ever was like, oh my God, I have this dream of being a lawyer. It definitely was not romantic for me, but I thought it could be a good business to run. And then during law school I decided that of all the types of law firms to have, criminal defense would probably be the easiest to run a business. I could build a repeatable process. I think I could advertise and actually attract customers. So basically I thought that I could start a law firm without much experience and probably get people in the door.

So after law school, I ended up going and working for a kind of notorious firm in San Diego for four years. Really, really high volume criminal defense practice. And then I had enough experience, I had helped hundreds of clients at that point. And so I'm like, all right, time to do my own thing. So I left to do my own thing and within two weeks I think I got a bar complaint. And so what was funny was that bar complaint is ultimately what led me down this whole road. So if it wasn't for that bar complaint, I probably would not be here talking to you guys. I would not have started My Case and then certainly would not have started on with Lawmatics.

Chase Williams:

I'm surprised you didn't start your own AVO competitor since you had that great AVO score after that bar complaint, I'm sure.

Matt Spiegel:

Well, you want to talk about AVO, that's a whole different story. We can talk about that. Because somehow, as I make the money sign, I maintained my 10.0 score. But no, it was a complaint about client communication. Basically they were just like, my lawyer didn't call me back quick enough. So I started thinking, I'm like, how do I... This guy called me at like 9:00 in the morning and I called him back at six. And that wasn't quick enough for him. But I was in court all day. I'm a criminal defense lawyer. I'm in trial. I can't answer the phone when I'm in judge's chambers or when I'm talking to a jury. I got back to him as quick as I could and I have other clients and I started hearing the same thing from other clients, although they didn't make bar complaints. And the issue, it's not like they had something critically important to talk to me about. They wanted to know when was their next court date and where's my police report? I want to see my police report.

These are two very basic things that if I could just provide them with that information, they wouldn't need to call me all the time. And so I'm like, well, wait a second, can't I just add this to my website so that my clients can log in and they could just see their calendar. I could upload their court documentation and police report. And so my cousin who was building my website, he was just a basic website builder. I'm like, "Dude, can you build something on the back end of my site so that my clients could get this stuff?" And he's like, "I mean, I can try." He's like, "I have no idea how to do that though." So we kind of hacked it together and I'm talking to my friends and my friends are like, hey, can you build that for us? I'm like, no.

Chase Williams:

Was there anything out there that was similar to-

Matt Spiegel:

No. So we were using a couple products. I think I was using Clio at the time. I also had tried Rocket Matter and those are brand new, just online practice management solutions for billing and stuff like that. But they really didn't have any sort of client... There was no client portal. That wasn't a thing really. And so I hired on a buddy to come basically found My Case with me alongside of my cousin and I'm like, hey, you're an engineer. Can you build this? I think other lawyers would want this portal. And so we invented the client portal and that's all that My Case was. And we were like, other lawyers are going to want this. And we started trying to show other lawyers and other lawyers were like, hey, this is really cool, but we don't want to use it on its own. It needs to be part of this big solution. And so we went back and we just built our own practice management system and that's how My Case got started.

Chase Williams:

How long did it take?

Matt Spiegel:

I mean, it's never done. My Case just sold to LawPay. Big transaction worth a billion dollars now. And it's still not done. The software is never finished, but it took like six months to build a version that we could go out to people with, really a year before we really went to market. And then it was a year and a half later that we had grown pretty big and we sold to a company called AppFolio. So it was a pretty quick run before acquisition. And then I stayed with that company for years after that still running My Case. But I did it alongside. I mean, I started my law firm in 2009. I had the idea for My Case at the very end of 2009. Also had my first kid or found out that we were pregnant with our first kid right in there too. Just a whirlwind. And then I still had my law firm. My law firm was just getting started. So the first year and a half, almost two years of building My Case, I also had my law firm. It was crazy.

Ryan Klein:

The story about your cousin building the website, it sounds like when Chase and I were starting an agency, we'd be pitching lawyers and at the end of the day they'd be like, you know what? My cousin's just going to build the website, he's going to get me a deal. So maybe we were talking to you for all we know back in the day. So when you're going through this process, and obviously you're a busy lawyer and you're kind of assembling this dream team to launch this new software, how are you coordinating it? Were you essentially leading it or someone else or are you arranging for time on weekends or late evenings?

Matt Spiegel:

Yeah. No, I mean that was the trick was I had this law firm and the law firm was... I was having a kid, a law firm is what's putting food on the table and a roof over our head. This pie in the sky idea of building a software company, it's just a dream at that point. I had like four offices in my law firm and one of the offices was my cousin and my other co-founder who were working on building My Case. And so everyone was just sort of moonlighting. It was one of those things where it's like, you have this idea, you have something that you think could be really cool, but everyone needs to work. Everyone needs to still make money. And we weren't raising millions of dollars from a venture capital at that point, things like that. It's a side hustle. It was totally a side hustle at that point. And what we really figured out how to do was to leverage the law firm to help us build My Case.

One of the biggest things, one of the toughest things was creating conviction amongst my co-founders that this was worth it. That was the first hurdle was like, you're going to do something like this where everyone's going to work on nights and weekends, they're going to give up a lot of their life in order to do this. And unfortunately, I couldn't really code, so there wasn't all that much for me to do. I can sit alongside of them and watch them do it, but at the end of the day, in the beginning, the early days, it's really all them writing code. You've got to convince them that this is worth it. And I think doing that was a bit of a challenge, and so we ended up just trying to figure out ways to make it fun. When you're doing a side hustle like that, I feel like you've got to make it fun. It can't feel like work.

Chase Williams:

Was there a point where you built it out and you would try to go to market and you're just like, man, nobody wants this. Did we waste our time? Did you have that feeling or were you pretty much like, this is going to work, no doubts.

Matt Spiegel:

I'm a super competitive guy. I think you kind of have to be competitive if you're in this world. And so losing was never really an option for me. But when we went to market, we went to this conference, this is going to date me I guess a little bit, but there was a legal... There's a big conference in New York called Legal Week. It used to be called Legal Tech, and they used to have one on the West Coast, they used to have one in LA. So this was like 2010. And we took the My Case client portal, we took it there and that's where we got the feedback from people like we're not going to use this. We might use it if it's part of a bigger practice management system, which could be cool, but we're not going to use it. And that was a moment where it was like, these guys had built this thing and I told them that other lawyers were going to want this, and now other lawyers are telling us that they're not going to use it.

And so it's a little bit of a challenge I think at that point for myself too to sort of regroup and be like, guys, now I'm saying that we need to go and build this massive product. This was something pretty easy to build, this client portal, but now we need to go build something really big and this is going to take a lot of time and a lot of effort. And rallying behind a negative experience because being told that no one's going to use your product is a negative experience, rallying around that was definitely... We did it over a lot of beers, that's for sure.

Chase Williams:

Were you guys all at the conference hearing this news or was it just you and then you had to relay?

Matt Spiegel:

No, no, no. We were all there. We were all experiencing it. And I think what's cool is that lawyers were really great at this point. The feedback was, yeah, we're not going to use it, but it was like, we want to. We want to use it, you've just got to give it to us alongside of other tools because we just don't want this other thing that we have to use.

Ryan Klein:

Yeah, that's true. I mean, even today it's hard enough to get anyone to adopt one piece of technology. We have people that you could talk until you're blue in the face about the benefits of implementing this and showing the before and after, like you're using Excel spreadsheets or PDFs or handwriting things and this technology is going to solve it, but it's just going to take a little bit of dedication in the beginning, and they won't do it. So I can imagine 10 years ago.

Matt Spiegel:

Yeah, I mean, look at what's going on in the market right now, right? The idea of all in one solutions is still prominent, it's still what a lot of companies, big companies out there, Clio, My Case, File Vine, Smokeball, RocketLink, these companies are all trying to sort of strive for that all in one field. It's still the mentality and it was very much the mentality back then.

Ryan Klein:

So how do you get people to really start adopting new technology and giving it a shot, especially when law firms especially can be so averse? Did you have a breakthrough moment or have to do some sort of clever positioning?

Matt Spiegel:

No, I mean, I think at that point my strategy has always been very simple and it is just always listen to the customer, never listen to me basically. I'm a product junkie. At my companies where I spend most of my day to day beyond just basic CEO duties is in product. That's where I focus my time. And I made the mistake early on of building what I thought lawyers... I was a lawyer, so I was building stuff and maybe very early on that worked to build stuff that would basically scratch my own itch. But as we started to build and put a product out to market, you realize you cannot do that. You just have to listen to what your customers are telling you. And if you let your customers drive you and drive your product roadmap, it's been very successful for us.

So that's where, to me, the breakthrough moment is really just deciding that we're going to listen 100% to our customers. And honestly as a law firm, you kind of should do the same thing. Our discussion today is really fun and may seem completely unrelated to law firms, but I actually think it's very related to law firms too. If you're treating your law firm like a startup, you're building this business, it's not just about how you practice law, it's also about the service that you provide and the experience that you provide and you need to listen to your customers in order to figure out how to make your experience better. And so when we started doing that as a product department at our company at My Case, and we've done that since day one at Lawmatics, that's when we really saw, okay, now lawyers, they're very happy to adopt our technology because we're building stuff that they are telling us to build.

Chase Williams:

So I assume you received some success at My Case and then it got to a point where you sold the company. So what happened next? You worked for the company some more I believe you said, and then you exited at one point.

Matt Spiegel:

Yeah, so we exited. I sold the company in 2012 and it was a great experience. I loved the company that we sold it to. We IPOed in 2015 and then that's when I left. So I was there about three years, almost three years after the acquisition, and incredible experience. And then I ended up going and messing around for a little while. I got brought on to a totally non-legal tech company. It's actually owned by a guy in Australia who owns a lot of legal tech companies, but I wasn't allowed to go work for a legal tech company at that time. So I went and worked for his non-legal tech company. I ended up taking that company over as CEO for a couple years and I was going back and forth to Sydney, Australia all the time, which was cool in the beginning, and then at that point now I had two little girls, and so traveling over there for a couple weeks at a time every two months got to be a lot.

And honestly, I was the CEO, but I was still working for somebody. I had a chairman and I decided I needed my own thing again. I wanted to build my own company and be able to control the product, build a software product because the company I was working for was not really a software company. And then Lawmatics was what happened. We really saw this need in the market. We identified this need for our CRM back at My Case in 2014, and then in 2017 when I was going to start another company and we're like, man, this is still this massive hole in the market. And so we set out to solve it.

Chase Williams:

So I bet your experience starting Lawmatics was a little bit different. Did you call your cousin again or how did that work?

Matt Spiegel:

No, definitely did not call my cousin. My cousins was off doing other things, enjoying life a little bit more. I had another engineer who was working with me at My Case who I had brought along to my companies that I had done after I left My Case. And so I brought him on to kind of be our founding CTO. The beauty is this time around, one thing that I realized is I had a lot more access to great people the second time, and so I was able to build a team around me. Also had a little bit more access to capital the second time around, so I was able to build a little bit of a bigger team earlier on to go and build this thing. Lawmatics is a freaking beast, I mean, we've been building this thing for five years and we're just getting started. It is a massive piece of product. And so it took a while to build something that we could really be comfortable going to market with that had some product market fit.

And then it's just been a wild ride ever since and much different path though, whereas My Case, we never really raised money for it. We sort of built it as a side hustle and then ended up getting acquired pretty early on. We're two or three rounds into venture funding now. We've raised almost $20 million, built a big company and been doing it for five years and are really pushing hard down the path of doing it ourselves without hitching our wagon to anybody. It's a very different approach.

Ryan Klein:

What do you think is different about your day-to-day leading this versus My Case? Is the day comprised of different responsibilities and types of meetings?

Matt Spiegel:

Totally. It couldn't be any different. When the company gets to a certain size, your day-to-day as a CEO becomes about the people and not about the product. My issues are managing people and people problems and not as much the product. I try to focus as much time on the product as I can, but we have a big team and that big team requires lots of different attention points, whether it's career path and promotions or hiring, firing, performance. All that becomes really important at a company our size. And that's a big difference. And in My Case, when we sold My Case, it was me and two other people, well technically three other people. We were four people at the company. That was it. And we definitely grew pretty quickly under AppFolio. I had a lot of help there because AppFolio had some incredible executives who were there to help me learn how to lead the company at scale.

But here at Lawmatics, it's just me. We're doing it on our own. It's a very different experience, but it's so much fun. Our culture is everything to us. One of the things that we've been very fortunate is we just moved offices, everyone's getting rid of offices, we just moved from 4,000 square feet to 12,500 square feet. We more than tripled the size of our office because people are coming in. We have this amazing culture. That's the part that I'm most proud of. It's what makes me get up every day is the team that we've built.

Chase Williams:

What do you think makes the culture so amazing?

Matt Spiegel:

Man, that's a good question. So we have this super cheesy value, but I think it plays into why our culture is so great, and that is friend before colleague. Obviously you're not going to be best friends with everyone that you work with, but it's that we want everybody to treat each other as a friend before just a colleague. And that means just a different level. A colleague is someone you just work with and so the relationship is work centric, right? But a friend is someone you're going to have different compassion for and you're going to understand them on a different level and have sometimes a deeper connection with, and we strive for that and it's been incredible.

Chase Williams:

Is that a core value of the company? If you find somebody that doesn't follow that mantra, are they gone or is it more-

Matt Spiegel:

Yeah, I mean, we've never had to fire somebody for lack of fit culturally. So we've done a good job of hiring. I think we look for that. We look for a good fit. I mean, I think we've had people leave, they weren't fired, but they left who maybe weren't the best culture fit. So I think that they just don't assimilate as well. It's not as fun for them to be on the team. But it is definitely one of our core values and something that is very important to us. We're not hiring 100% remote people. We are hiring people in San Diego who are going to be excited about coming into the office and being around people. And we do it three days a week, Monday, Tuesday, Wednesday. Thursday and Friday are remote days. But if I were to show you our office right now, you would see a whole bunch of people still here who even on the day where they can be remote are choosing to come in. It's really cool.

Ryan Klein:

That's cool. Yeah. I like what you were saying about the core values. I agree. I think that once they're established and people really own them, it kind of works itself out. It permeates the organization and people either kind of start to adhere to it or they start to naturally make their way out as it's observed more and more. So what are you all looking forward to the most this year? It's January, we're just getting started. Do you have any initiatives that everyone's really rallying around right now?

Matt Spiegel:

Yeah, we do. We really do. This is actually a huge year for us. We're really, really excited. What I'm most excited about is conferences are in full swing again this year. We love going out face to face with our customers. We love traveling to these different places where conferences are. I know we were talking earlier, I think you, Chase, met some of our team at a conference just a month or two ago. We love doing that. I'm really excited because we have a full slate of conferences set up. I'm actually going to New York next week. These are things I really love to do personally and our team loves the opportunity to do it as well.

But we're really focused on scaling the business, the infrastructure of the business as we start to really hit pretty massive milestones inside of our application, like the volume of things getting processed and just our general infrastructure. We're really focusing on the reliability of our platform in 2023 and making sure that it is scalable for the future. That's a big focus of ours. We're also starting to attract bigger law firms. That's a big focus for us is we've always been there for the solo and small firms. That's been our bread and butter, but the product has really evolved to be very suitable for a bigger firm, and that's a big focus for us too is moving upstream a little bit this year.

Chase Williams:

I'm very curious about what are your thoughts on... The buzz topic right now obviously is AI. So are you guys thinking about integrating any sort of AI into Lawmatics? I could see there's possibilities there. I just want to get your opinion there.

Matt Spiegel:

We've always had a little bit of our own AI. It's not really AI, but it's more like predictive analytics around your leads. And I think it could be really valuable there. It can sort of take a look and say, this lead has the potential to be worth this much to your law firm, given all of the different data points of a particular lead, the type of case, maybe everything about the person. AI can take a look at that and compare it to all the leads you've gotten and the cases that you've handled and see could this be a good fit for your law firm? I think that there's some value there. Where everyone likes to talk about it now is around actual legal work like contract review and contract generation and ChatGPT and building things for you. And I don't know that the question is... I definitely think it can be useful for certain things, but I definitely don't think it's going to...

First of all, lawyers aren't going to let AI replace them. It's a big enough union that the institution won't let it happen. And I think that there's going to be a lot of hairy issues around it too. If you start to use AI to do things that a lawyer would've normally done and you don't have a lawyer at least review that, I think there's going to be some rocky roads down the way. But there are a lot of things that AI can be really useful for. And so I look at it as like things that are relatively harmless, low impact. So one of the things about Lawmatics that's really a feature that is value proposition that is extraordinarily powerful is the marketing side of it.

Lawmatics does all of your marketing, all of your email marketing, your newsletter campaigns, birthday emails, drip campaigns, anything you want to do in Lawmatics. You guys as marketers, you're going to have all these amazing ideas and best practices, and Lawmatics is what actually helps you execute them. Lawyers who are out there, small law firms who maybe can't afford to have a good agency, help them with experimenting with content or managing their campaigns, they can maybe go to AI and get content for an email that might work really well. I think that those are areas where it can help. But the other areas, I'm a little skeptical.

Chase Williams:

For sure. Yeah, I mean there's basic, I don't even want to call it AI, but if you had a preset document, you just type in this new client running through this process, and all that really is is stuff that you could do in Excel, essentially, but they can call it AI.

Matt Spiegel:

That's why I say, we have a little bit... Like Lawmatics, you're building your own AI a lot of times because you're building these automations, right? But as far as real AI that is consuming data and making decisions about what content to give you or decisions about something, it's scary for some parts of legal when you start talking about replacing the work lawyers do. But when you're talking about ancillary things, whether it's, hey, I want to put an ad out there, I want to do a banner ad on a website, or I want to do a paper click campaign and I need a catchy headline, I think AI could be a great place to start for that. I think that it's not the place to end, but it's a good place to start.

Chase Williams:

No more writer's block.

Matt Spiegel:

Yeah, right. It's good inspiration if nothing else. Right?

Chase Williams:

Well, Matt, thank you so much for your time. If any of our listeners want to learn more about Lawmatics or you personally, what's the best way to reach out?

Matt Spiegel:

So I'm always excited and happy to get emails directly from anybody. My email address is Matt, M-A-T-T, @lawmatics.com. Our website is lawmatics.com. Anyone can feel free and go there if you're interested and in the business side of your law firm and managing the business side, Lawmatics is really the only [inaudible 00:29:34] out there for you. Go check it out. But if you have any questions just about... If you're someone who's looking to start a side hustle on top of your law firm, I'm happy to chat about it. Reach out.

Speaker 2:

Thanks for listening to the Legal Mastermind podcast. If you're interested in working with Ryan and Chase, please email mastermind@marketmymarket.com. Make sure to join the free mastermind group for growing and managing your firm a lawfirmmastermind.com. Ryan Klein and Chase Williams are the managing partners at Market My Market, one of the top legal marketing companies in the United States.