Lessons From a Startup with Matt Spiegel 364


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Today on the podcast Jim and Tyson sat down with Matt Spiegel, Co-Founder and CEO of Lawmatics

Lawmatics is a sponsor of MaxLawCon 2021!

Matt is a serial entrepreneur, Attorney and golf enthusiast. Matt was a practicing criminal defense attorney for 6 years. In 2010 he founded MyCase, which went on to become one of the most popular cloud based legal practice management solutions. Matt was also the CEO of MyCase, which was acquired in 2012 by AppFolio, where he remained as GM until 2015.

In 2015, Matt founded ExpoGuru, an event marketing management software. In late 2015, Matt became the CEO of Cammy, a global consumer tech company with headquarters in Sydney, Australia. In 2017, he decided that it was the right time to go back in the legal software industry with the Lawmatics platform.

4:16 what is the market telling you
10:08 maintaining culture through growth
10:47 doubling in a pandemic
11:45 hiring for culture
13:28 lessons from a startup
17:12 the next phase for Lawmatics
19:35 software with open API

Jim’s Hack: Book - The Tao of Leadership Lao Tzu's Tao Te Ching Adapted for a New Age  

Matt’s Tip: Be the Zappos of law. Stop worrying about being a good lawyer and become a good customer service agent.

Tyson’s Tip: Pexels App in Zoom for backgrounds.

Watch the podcast. 

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Run your law firm the right way.

This is The Maximum Lawyer Podcast.

Your hosts, Jim Hacking and Tyson Mutrux.

Let's partner up and maximize your firm.

Welcome to the show.


Jim:                 Welcome back to The Maximum Lawyer Podcast. I'm Jim Hacking.

Tyson:             And I'm Tyson Mutrux. What's up, Jimmy?

Jim:                 Hello, my friend. Glad to see more photos of you flying all around Central Missouri in your little plane. I'm glad you're back on the ground safe and sound and glad you're here to record this podcast with Matt and I.

Tyson:             I appreciate that. Although you told me it was getting too much. But I was telling you, every time I fly over Orlando, the new airport, I'm going to take a picture of it so. It just happens to be a back‑to‑back day. It just seems a little redundant but it's back‑to‑back day so. It'll be spread out a little bit. As I go to a new airport, I'll take a new picture. I'll post it. So, let’s [inaudible 00:56:00].

Jim:                 I mean, they do look sort of the same. It's like that arm holding up the wing and, you know, that same old picture.

Tyson:             This one's a little cooler because I have the sun in the background. It was kind of neat. It was a fun little background.

So, let's get started with our guest today. So, we have Matt Spiegel who actually is, again, a sponsor of the podcast. And--

I want to make sure I'm not mis‑stepping here, Matt, you are the founder of Lawmatics but you're also still the CEO of Lawmatics. To make sure you've not sold it recently or anything else. You are still the founder and CEO of Lawmatics, right?

Matt:               Yeah, still going strong. Yeah, MyCase is the only one that I've sold at this point.

Tyson:             No. That's why I asked that because-- and I want to get into a little bit about your background too because you've already previously built a-- I was kind of teasing a little bit. You've already previously built a very successful practice management software and you sold that. And then, you've moved on to Lawmatics, so.

But before we get into all of that, tell everybody a little bit about your background. Those of you that have met you before probably know a little bit but give people your background and how you got to where you are now.

Matt:               Sure. I mean, the short story, which I like to keep it very short, is I'm a lawyer who was practicing, and I had a problem, and I wanted to find a solution for that problem, and it ended up turning into a product called MyCase, right, which I'm sure most people who are listening to the podcast have heard of MyCase at this point. So, MyCase was a company that just kind of grew out of my own law practice. And we turned it into something, you know, pretty decent size. And I sold that company back in 2012. And I stayed on as the GM until about 2015. And then, I made my graceful exit from MyCase.

And then, you know, it was a couple of years of doing some things that were not legal related. And then, to use the cliche, it just pulled me back in, right? So, I really-- I was doing something. I was running a company as CEO, but it was not a company that I owned. And it was not a company I started. And I think I really wanted to go back to building something myself because it's the part that I love the most. And it's just so exciting and so fun.

And, you know, there was no space that I knew better than legal, obviously. And so, this opportunity for Lawmatics is something that we had identified many years before we started, like when I was still at MyCase. And so, in 2017, I decided to come back into legal. We took on a really big problem to build a product that we knew was going to be really, really massive and take a while to get right to get product market fit. And we were right. It did take a while but now here we are. And, you know, Lawmatics is a pretty well built out product at this point.

Jim:                 Matt, talk to us about that day where you said to yourself, you know, “I've solved this problem for myself and I think I might be able to turn this into something that people would buy,” talking about MyCase. So, what goes on in your mind when you're having those conversations?

Matt:               Yeah. Well, what went on in my mind was like complete disappointment because, at first, what I tried to sell to other lawyers was terrible and they didn't want it. I was like, “What do you mean? Like, this is a great solution for me.” And, really, what it was, was like just getting some feedback from colleagues at first, right? It was like, “Hey, I did this thing for my own customers that they seemed to like. Do you think you guys want to use the same thing?” And the feedback was like, “Yeah, that sounds really cool.” And so, then. we tried to put it out in the market, and we just get-- you know, we fall flat on our face, right? It's just, “This is not anything that we need.” But the feedback was that, “Hey, it would be something really useful, but it needs to be like mounted inside of a bigger piece of software.” That was the feedback that we initially got with this like-- you know, the initial problem that we were trying to solve. And so, then, we said, “Hmm. Okay.”

So, we started off with just this really small little problem that we were trying to fix. And then, the market told us that that's a good problem to fix, but it needs to be part of a bigger solution. And so, we pivoted and ended up building out a full practice management system which is what MyCase is today. You know, then then, obviously, it turned into something more successful. But, in that beginning, it was like taking that little feedback, getting a bunch of, you know, constructive criticism on it and then turning it into a product that that would have some market fit.

Tyson:             So, MyCase and Lawmatics, they're different products. They do - I wouldn't say completely different things but extremely different things.

Matt:               Yeah.

Tyson:             [inaudible 00:05:06] built. I mean, I'm extremely impressed with Lawmatics, just the all the things that you-- all the different features are really, really cool.

But what was it like? It had to have been sort of like a roller coaster - building a company, growing a company, selling a company, and then starting all over again. What was that roller coaster like?

Matt:               Look, it's-- I feel like-- obviously, there are a lot of peaks and valleys. Like kind of with anything, it's the same thing starting a law firm, right? You're going to have a lot of peaks and valleys in doing that. It's like any business, right? It's no different.

For me, it was-- you know, all of MyCase was a pretty big peak. I've got to be honest with you. You know, we started strong. We kept going strong. And, you know-- and then we were acquired. And after the acquisition, we got even bigger, right?

And so, maybe the only down part is then seeing it get re‑traded, just a year ago for, you know, around $200 million and not still being there, right? So, maybe that was the downturn of the roller coaster. But it was a pretty-- you know, a pretty big climb to the top, a pretty consistent climb to the top.

And then, you know, with Lawmatics, there's definitely a lot more peaks and valleys, right? And I think it's just a nature of timing of the market, the type of product that we are, that it's a little hard-- you know, just because of how big and wide Lawmatics goes, it's harder to get product market fit.

So, I think what we saw in the first year and a half, where we're building the product, is just a lot of, you know, constant, you know, push and pull with attorneys trying to, you know, understand like, “Hey, we're not like trying to give you this product yet. We're just trying to really-- or give you something that is really going to be a solution. We're trying to get feedback here, from you, to build a better product, right? And so, that always comes with a lot of peaks and valleys, right, because you have a lot of really great moments where you figure something out and, you know, it clicks. And the feedback from the customer will show you that. And then, there's a lot of times where you completely swing and miss, right? And you've got to go, you know, back into batting practice like you're off the field. You know, that was a lot of the first couple years of Lawmatics.

And then, once we have that product market fit, it's a really special moment, at any sort of business, right, especially a software business. When you achieve that product market fit and you're now providing this tremendous value to customers and the thing starts to grow organically because of the value that you're providing, that's a really special moment and things start to just go up. And that's really been the last, you know, year and a half - two years for us, kind of coming just before the pandemic. And so, we're still trying to ride that upswing.

Jim:                 Matt, you don't know about this but Tyson and I really started this podcast because we were in love with this piece of software called Infusionsoft--

Matt:               Yeah.

Jim:                 --which was a sales software. And we actually thought that we could build our law firms on the back of Infusionsoft. And, you know, through fits and starts, we eventually realized, both of us, that you couldn't just run a law firm on sales software. But it was really powerful and we really loved it. And we were big fanboys. We went to their conference. And Tyson got an Infusionsoft tattoo on his ass. We really liked it. But then, they took the venture capital money and things really changed. I wonder if you could talk just real briefly about what happens when that money comes in when you get acquired. Like, what shift sort of happen and what--

Matt:               Yeah. Yeah. So, there's a big-- I mean, so, first of all, there's a big difference between getting acquired and taking venture money, right? And like, for us, venture money can do-- well, it can do one of many things, right? But like the kind of binary things that it can do is it can help you go really fast. Well, it's going to help you go really fast no matter what, right? But it can help you go really fast in the direction that you’ve really wanted to go or you could go really fast in the direction that the VCs think that you should go. And so, it really depends on like there's really good venture money and there's really bad venture money, right?

So, like we took venture money. We did our first round of venture money about actually almost exactly a year ago. It's like we signed our term sheet around this time last year. We closed in like beginning of September. So, we're not even a year removed from doing our first venture round but we’ve got great partners. And we have great partners who completely let us do exactly what we want to do. The vision that we sold them on is the vision that they want and the vision that they-- you know. And even if it doesn't work, right? Even if it's like, “Hey, we're having-- like, we're struggling here or like this is going really well, but this is going bad.” It's not, “Okay. Well, then, change what you're doing,” right? There's none of that from the partners that we have. And good partners will be that way.

Bad partners could really steer a product in what could be the wrong direction, right? And I think you do see that a lot. Kind of to your point, Jim, it’s like, you know, a company brings in a ton of money and then they get pushed in a certain direction. Or, it looks like they did a venture round but really what they did was take private equity money and, you know, sell out a large portion of it. Private equity comes in and actually ends up controlling the company and then forget about it, right, because now you're in a completely different world.

And so, it really just depends on your partner. It's not necessarily a bad thing. It's definitely a necessary piece if you're trying to grow fast for a company like us. But it's really about finding the right partner.

Tyson:             So, let's talk a little bit about growth because you are-- it seems like, at least from the outside looking in, that you are seeing quite a bit of growth. How do you maintain that culture in the company, because it does seem like you all have a pretty good culture? So how do you maintain that as you continue to grow?

Matt:               Yeah. Great question. When I get you the answer, I can report back because I have no idea. I mean, we've been really lucky to have a great culture. And I think we've been really lucky to keep a good culture for the last year and a half, right? That's been the biggest challenge.

What's interesting is, at the start of the pandemic, Lawmatics had like-- I think we had eight employees or nine employees. And we have-- as of two days ago, we have 21, right? So, we've more than doubled during the pandemic. And so, what that means is, you have all these new people who are starting, who don't even know what your culture is because there's no office to go to, right? That everyone's remote. You're doing it on Zoom.

So, we've tried really hard to instill a culture through things like this, through Zoom meetings and like we will get together as a team at like coffeeshops over the last year, so. And, now, we're transitioning back into the office. So, we're actually going back into the office next week, I think, for the first time. And it will be interesting, right? Like, I think it would be an interesting conversation to have in another few months to see how those employees who got introduced to our culture virtually can then like assimilate into our culture in an in‑person environment and I wonder if it changes, right?

But, to me, it's like if you get the right people, if you're really good about hiring, then you get the culture, right? Like we hire for culture at Lawmatics. So, you know, if we think that the person’s not going to be a good fit, culturally, and bring that kind of aspect to the team then they probably won't make it through our process. So, like we're not just looking for, you know, smart and driven and, you know, good experienced. We're really looking for that person who's going to-- you know, kind of one of our core values is like friend over colleague, meaning like we want everybody-- you don't have to be best friends with everybody you work with. We want everybody to be somebody who you could think of as a friend. Before, you just think of them as someone that you work with. And so, we hire for that. And like that's kind of been our strategy for building a culture.


Tyson:             The Guild is an insanely productive community of lawyer‑entrepreneurs with a growth mindset who share their collective genius and hold each other accountable to take their careers and businesses to the next level. But in 2021, we are upping the game. In addition to exclusive access to the group, FaceTime with the two of us, discounted pricing for live events, and front‑seat exposure to live recording of podcasts and video, we are mapping out, for members, the exact growth playbook with our new program, Maximum Lawyer in Minimum Time.

Jim:                 As a Guild member, you'll build relationships and experience content specifically designed to complement your plan for growth. For a limited time only, The Maximum Lawyer in Minimum Time program will be offered for free to all new Guild members. Join us by going to maxlawguild.com.


Jim:                 Talking with Matt Spiegel. He's an actual serial entrepreneur. We hear that phrase thrown around a lot, but he actually has started more than one business so, by definition, he's a serial entrepreneur. And we're talking to him today about Lawmatics and their sponsorship of MaxLawCon 2021 which we're very grateful for.

Matt, what can fast‑growing law firms learn from the startup community? What lessons are there from startups that can transfer to companies like mine or others that are growing really, really quickly?

Matt:               So, my biggest thing and like kind of the big thing that I've been-- I'm not going to say, you know, preaching about, but like any of the conferences I've done over the last, you know, year which have been really awesome to do the virtual conferences. They've been really fun. I'm very ready to go back in‑person, thanks to you guys. And I hope that doesn't change. But, yeah, you guys will be our first in‑person conference since the pandemic and I'm just stoked. I'm going to be there personally.

But one of the things I've been kind of bringing up, which I think stems from our experience at, you know, software companies and startups is like the number one thing that we care about, above all else, right? Product is important. And, you know, engineering is important. What we care about more than anything else is the customer experience, right? Flat out. What we care about is giving them an amazing experience whether that's through the product, whether that's through the service. It doesn't matter what it is, right? But, at every step of the way, it's giving them an incredible-- you know, delighting them.

And I think that that's something that's pretty unique. It has traditionally been pretty unique to startups. If you talk to most startups, there is an obsession with customer service, right, with customer success. And it permeates through everything that we do. And that's something that I think lawyers can really learn from.

And so, like this idea, this concept that I've been trying to share with law firms is this idea of like, you know, I call it the path to delightenment. And it's, you know, this idea that like the client goes through a journey with your law firm, right? And you think about it-- we think about everything just in terms of the client. We don't even think about it in terms of the law firm. We think about in terms of the client. And this client goes through a journey with your law firm. And, you know, at every step of the way, and there's very different-- like, there's very specific phases of this journey that that we break it down into. But at every step of the way is an opportunity for you to delight your customer, right, to provide like that extra layer. And it's very important that you do that as a business, right? It's very important to take that advice, you know, from a startup, you know, who obsesses over customer service and bring that into your law firm, right?

Every opportunity, whether it's during the first phase which is-- we break it down into three phases - the intake phase, the active case phase, and then the post case phase, right, which is just as important as any of the other two phases. And at every opportunity, like whether it's, you know, an immediate engagement and like an easy way for them to book an appointment. And then, you know, just like nurturing during that intake process is an opportunity to delight them at your first impression. Or whether it's during the case, just overly communicating, you know, client portal access. Just, you know, making sure that they're fully aware of everything to the end, when you're following up with them for a year after their case is over, right, with a nurture campaign.

Like, these are all opportunities to delight your client. And it's really critical to do so. Like what I always say right now is you could be a great lawyer who delivers incredible outcomes but, if your customer service sucks, that person might not refer you business. Whereas, you could be a mediocre lawyer, and-- I mean, you probably can't be a god‑awful lawyer. I think you can get away with being a mediocre, an average lawyer, but provide exceptional customer service throughout the way and that will be a customer for life, right?

Tyson:             I love it. I was going to wrap things up because that was such a great way of ending it. But I do want to ask you this because you provide so much with Lawmatics. I encourage anyone listening to this to actually go on the website and just look at all the things that you all provide. It's really amazing. But what's the next phase for Lawmatics? Like where are you all headed? Because I know you’ve thought about this before or you had to. But where are you headed?

Matt:               Yeah. I've thought about this a lot. And I think like, for us, we still have a lot of depth that we need to explore with our current set of-- I mean, like you said, we do a lot. Everything we do kind of has this nexus though to being, you know, intake and marketing automation, right, and this idea of automating everything. And so, you know, we have all these modules. It’s like, you know, we have like our own calendaring system. We have our own document, you know, automation and signature system that we’ve built. And like we've gone pretty deep on these things, but we need to go deeper, right?

So instead of like going horizontal, we are focusing a lot of time which is doing what we do even better and enhancing our integrations is a really big part of what we're doing. We have, you know, great relationships and integrations with a lot of the practice management companies out there because Lawmatics needs to hand off the case for that portion, right? And then, we take it back when the case is over. And so, we have great relationships with them. We want to make our integrations with those products even better. And then, there's lots of other solutions that customers are asking for integrations with.

And, you know, at MyCase, I made the decision very early. This is kind of like an infamous decision now where MyCase was going to be a closed environment. We were going to do everything ourselves. There was going to be no integration with anything, right? And I'm, you know, more than happy to admit that that was the wrong decision, right. Like we see what Clio has been able to do, you know, by having so many integrations and having an open API. Incredible things have been built, right, that couldn't have been built if there wasn’t access.

So, for us, we took that same approach where we have an open API and we're going to lean on a lot of integrations. And some of the stuff we will build ourselves but some of the stuff we will integrate. And I think that there's a lot of integrations we want to explore over the next six months to a year. So, that's what we'll see. Stay tuned. There might be some surprises along the way but that's the current way of thinking around here.

Jim:                 Well, that's a great segue into what was going to be my last question. And we talked to a lot of law firm owners and we have many in The Guild who really like Lawmatics. Then, we talked to some other people who use those closed environments. And, you know, I've really been preaching that if a piece of software doesn't have an open API, if it doesn't talk to other software, and you're doing double or triple data entry, you know, that's for the birds and you’ve got to get rid of that. Can you talk to us about why it's important for law firms to have software that is open?

Matt:               Yeah, because, look-- I mean, no matter what solution you have that claims to be an all‑in‑one, it will not be an all in one, right? Like, it's just not going to happen. There is going to be something that is critical to your practice. Maybe some like nuanced little tool that you use that like is not going to integrate with your all‑in‑one platform, right? It's not going to be a tool that can be executed by something inside of the platform that you're using. And so, the best way to make sure that you don't have that interruption in your business and that you can continue doing the certain things, the way that you really like to do them. And that is the most efficient for you is to have a platform that can build an integration.

Like especially lawyers, there are so many sort of like obscure little tools, right? Software companies that were built like 20 years ago that are still around that, like, you know, a hundred lawyers use, right? And so, you're not going to find like a native integration built into a lot of the platforms for a lot of the tools out there. And then, a lot of the non‑legal tools that people use, you might not find integration.

So, a good open API is going to give you a couple of options, right? If they don't integrate with them themselves, it's going to give you the ability to have somebody build a little integration for you, right, if possible. But it's also going to give you the ability to use something like Zapier, right? If they go in with Zapier, right, which is like-- I like it if-- you know, just for anybody who doesn't know, it’s like an aggregator, right? It's an app that allows you to connect a million different apps together.

And so, for us, we put a lot of effort into our integration with Zapier so that we can get those little one‑off, you know, companies that that is going to be hard for us to build an integration with. And they're not going to put the resources to build an integration with us either. And so, they can just use it with Zapier, right?

So having that open API just gives you so much flexibility and a little bit more opportunity to not completely blow up your business processes.

Tyson:             I love it. That's great. I love that you integrate with Zapier. That makes things so great. So, very cool.

Matt:               Yeah.

Tyson:             All right. I do need to wrap things up. Before we do, I want to remind everyone to join us in the big group, Facebook group, if you want to mingle with other people that are like‑minded like you. If you want a more elevated conversation, go to maxlawguild.com and you can join us in The Guild.

By the time you're listening to this, we may have sold out. But maxlawcon.com, we're very, very close to selling out, so it may have been too late. If not, go ahead and get your tickets.

Jimmy, what's your hack of the week?

Jim:                 So, about twice a year, I get invited to come down to the US District Court and give a talk to the people that are becoming US citizens. And I always include that quote from Lao Tzu called, you know, “The journey of a thousand miles begins with a single step.” And I love that quote. And it helped me to find this book which is my hack of the week called The Tao of Leadership. And it's a bunch of his wisdom adapted for where we are now. And I just tried to read like one or two each day. It's really a wise book and it gets my mindset right. So, it's a good one.

Tyson:             Very cool. Very, very cool.

I'll have to borrow that from you whenever you're done with it. So, let me know when you're done.

All right, Matt. So, we always ask our guests to give a tip or a hack of the week. And I think you actually were a previous guest, so you may have remembered that. But do you have a tip or a hack for us?

Matt:               A tip or a hack. Oh, man, that's a good one. And I don't remember that from the first time. So, let's see. My tip-- I mean, like, I'm just going to piggyback off of kind of what I preached a little bit already, but my tip is going to be like, you know, be the Zappos of law, right? Like don't worry. Stop worrying completely about being a good lawyer and go to being a good like customer service agent, right? That's it. Super simple. And just watch what happens.

Tyson:             I think that's a phenomenal tip, especially off the top of your head, so that's really good. I love that. That's one of my favorite tips that anyone's ever given, actually. So, very good.

Mine is going to be-- it's funny because, before we got on the show, I was having problems removing my background. And I still can't figure it out. However, we're using something called pexels, P‑E‑X‑E‑L‑S. It's in the apps in Zoom. It’s actually really cool. I like the fact that I can choose pretty much any background I want because it's all built in. The only problem is I can't figure out how to turn it off, but I still do recommend it because it is really cool because you can choose pretty much anything. So, pexels P‑E‑X‑E‑L‑S. You can find it in the apps part of Zoom. Just go to zoom.us. You can find it there.

So, Matt, thank you so much for coming on. This has actually been-- it's been a lot of fun. To be honest with you, these can be sometimes hard to do with vendors but you do a great interview and you have a great product. And so, we just like hearing about your story when it comes to, you know, creating and selling companies. It's a really cool story, so thanks so much for coming on.

Matt:               Yeah, I appreciate it. I love hanging out with you guys. And I look forward to seeing you guys in person in just a couple months.

Jim:                 Thanks, Matt.

Matt:               All right. Cheers.

Jim:                 See you, buddy.


Thanks for listening to The Maximum Lawyer Podcast.

To stay in contact with your hosts and to access more content, go to maximumlawyer.com.

Have a great week and catch you next time.


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