(0:00:00) Scott: I’m the first one to tell you that I am horrible at building a brand or thinking about the brand, but I’m one of those, you know, great people who can be sitting up in the stands and go, oh, that’s an awful brand, right? But, you know, and I don’t know why, and I can’t quantify it. I can’t, you know, whatever.
(0:00:14) Scott: So so what I do is I lean into folks who are way smarter than me and way better at those things. I mean, let’s be honest, like, we started a company called Urban Airship, for God sakes. Like, it doesn’t exactly roll off your tongue. And the story around how we came up with the name was even crazier.
(0:00:28) Courtney: Hi, my name is Courtney and welcome to how they scaled it. We’re scaling is done with both sides of the brain. Today I’m excited to welcome Scott Covington, a serial entrepreneur and the co-founder and CEO of case Mark. Scott’s career has taken him from working on the wiki team at Amazon to launching and scaling multiple tech startups, most notably Urban Airship, which helped pioneer mobile push notifications.
(0:00:52) Courtney: Now, he’s tackling one of the biggest opportunities in legal tech with case Mark, an AI driven platform that’s helping attorneys process cases more efficiently and at scale. Scott, it is such an honor to have you here today. Welcome to how they scaled it.
(0:01:06) Scott: You are far too kind. Thanks so much for having me, Courtney, I appreciate it. I’m all right. I feel like we’re done here.
(0:01:13) Courtney: I know, I know well, you have such a good story, so it’s kind of fun to summarize it, but that kind of like leads me into my first question, which is your career has been so diverse, like, you’ve been kind of all over the place. You’ve done open source projects, B2B stuff, and now you’re finally in legal tech.
(0:01:31) Courtney: So what is driving those decisions to kind of like, bounce around or like where how do you decide where like when to start something new?
(0:01:39) Scott: You know, it’s funny because I think like a lot of entrepreneurs, you don’t necessarily pick what you’re going to do. It sort of makes you, and, you know, I do a lot of things in my life in threes. And sort of what I mean, there is, you know, you can sort of wrap your mind around three things at once.
(0:01:54) Scott: Like, I’m a fan of, you know, building companies, you know, signing customers, building product in a crawl, walk, run fashion. And then when I start companies, there’s sort of three things that are critical to it. You know, team, tech and timing. Team and tech are relatively simple, especially, you know, I’ve got a co-founder that I’ve worked with now for close to 15 years.
(0:02:14) Scott: And so, so the team in tech is you. The timing is always the really tricky bit. And so we got really lucky with Urban Airship with basically the launch of the iPhone. And then, you know, I sort of equivocated with what’s happening and legal is kind of the iPhone moment with respect to I am legal and so kind of leaning into that a little bit.
(0:02:31) Scott: And so, you know, in terms of how I pick it, it’s really just following the path of what’s interesting, knowing you start with some little simple products, shipping as quickly as possible and then just iterate, iterate, iterate based on customer feedback and then, you know, you sort of, you know, drown out the noise that you hear from investors who don’t get it or, you know, the customers who, who maybe aren’t the right ones at that time that those kinds of things.
(0:02:54) Scott: So, you know, it’s really just I hate to say it, but it’s following your gut a little bit. Yeah. And I think the, the, you know, longer I’ve done this, I think the more trust I put in my gut and I think it’s gotten better. It’s gotten a lot better, for sure.
(0:03:06) Courtney: Yeah. So that’s interesting. I feel like, that’s been one of my biggest learnings, too. Is that, like your gut actually is a really good guide sometimes. And I every mistake I’ve made, I’ve always thought back, like, I did have a gut feeling about this, and I still move forward because it made the most center. I had someone giving me that advice, but that gut feeling is like, it’s so important.
(0:03:29) Courtney: And I and I think that just over time, it gets more and more strong and it’s like, I you even better and better. So it seems.
(0:03:35) Scott: Like it worked. You know, I’ll never forget that back in, I think it was 2009. We just started Urban Air, so it was still really new. And I had gone and pitched an investor and he brought me in for the partner meeting, which is, you know, traditionally a pretty formal meeting. You’re usually meeting with the whole partnership.
(0:03:52) Scott: You’ve got a slide deck, you’re going through all these things, and they ask you the typical questions around, you know, problem, solution, Tam team like all these things. And I remember I put up a slide on the on the Tam and I said, you know, again, the paint was even dry in the company. I mean, we were maybe four months old.
(0:04:10) Scott: And, I had said that the, the Tam for the push notification market in the next five years would be like $1.2 billion or something like that. And, and I’ll never forget as he walked me out of the meeting and, you know, took me to sort of walk me to the elevator to leave. He’s like, you know, I’m just going to give you a little bit of advice.
(0:04:28) Scott: Don’t ever embarrass somebody like that with with a Tam, you know, like that. There’s no way your Tam’s ever going to be that big. That is absolutely crazy. And I was like, oh my God. So I left just defeated, thinking like I am a moron. And I was the moron because guess what, I was five staff by that time and so what I didn’t do is I didn’t trust my gut and just sort of ignore that investor.
(0:04:52) Scott: And I think the other thing too, is I’ve heard, you know, so many times in my career that I just it’s like, okay, great. You know, just get to know quickly with me. That way I can move on to the next person who probably gets it. And, you know, when you do find those folks who say yes, it tends to be it’s not just because they get sort of what you’re doing from a company or from a product perspective.
(0:05:11) Scott: They also get you as an entrepreneur and that you don’t have all the answers, but that you probably you’re going to figure it out because you, you know, can pattern match against sort of history and how you’re going to build your company moving forward. So anyway.
(0:05:23) Courtney: No, no, that’s that’s great answer. You mentioned so team timing and and tech those are the main three. And he said the team and tech are the easiest. Has that always been the case. Because I feel like a lot of entrepreneurs, when they’re first getting started, have a really hard time building their team or like knowing what to look for, knowing when to hire, when to fire has I.
(0:05:43) Scott: Yeah, I mean, I, I think the, the reason I think it’s easy for me is I’ve been lucky enough to have a co-founder for the last, you know, kind of a long. And so, so when it comes to the technology and the team, we’ve always been, we’ve always sort of resonated. I think the other piece is I have a technical background.
(0:05:59) Scott: You know, I did, you know, cut my teeth at Amazon at the turn of the century and I was on the Y2K team. I was literally like a system administrator in the data centers, like, you know, you know, literally shoving machines into racks and stuff like that. So I have I have a little bit of a technical background.
(0:06:14) Scott: I, you know, I used to write software. I actually still have an open source project that is still alive. I haven’t written against it since then, literally the 90s, but I just discovered that it’s still out there. It’s called Apache and it’s this open source, platform for basically hosting your own music. So if you have your own music and you want to sort of put it somewhere, then be able to get to it from anywhere, you can do that anyways.
(0:06:35) Scott: Yeah. But I just, I thought it was really funny that that project is still exists. So anyways. Yeah.
(0:06:42) Courtney: I mean, okay, so you as, you kind of like, have gone through your career since like, Urban Airship was kind of this huge, huge success for you and you scaled it to 50 million. Which is very impressive. And with a brand new thing that people never really even thought of. So as you were going through that process, what were some of those biggest, like lessons that you were learning and the experience that now you’re bringing to your other companies like case, Marc.
(0:07:08) Scott: Yeah, I mean, I think, you know, hindsight’s always 20, 20 and these things, but looking back, I mean, Urban Airship was one of those things that we literally launched it. We had the idea for the company and then went live with the product in 30 days. And, you know, and it was a timing thing, you know, Steve Jobs had announced or Apple was announcing basically that they were going to do these push notifications.
(0:07:29) Scott: It wasn’t public. You were under NDA as a developer if you knew about it. And we happened to be under NDA to know about it. And I had actually gone down and done this, you know, kind of cheesy campaign where I went out in front of Moscone Center and gave out a bunch of donuts and danishes to people because I didn’t know how I was going to launch the company anyways.
(0:07:46) Scott: And everybody was standing there in line to go into the Steve now the keynote address that they did. And we got really lucky on it because, normally they in June they announce a bunch of new features and things, and then they launch them in September. And instead of saying, oh, this is going to be live in September, it was like, no, no, this is going to be live in seven days.
(0:08:08) Scott: And so we had a bunch of competitors who had announced they had big parties. They had all these things happening that week at this event. The one difference is they all had these beautiful websites that were, you know, brilliantly designed and, you know, great stories and all these things, but they just had to enter your email on this and we’ll let you know when it’s available.
(0:08:28) Scott: You can come to our site and download the SDK. You get up and running. And we literally had a 90 day window where we were the only game in town, maybe 60 days, and it’s how we basically won the market. And so and then it was just we were kind of off to the races and then I learned quite a bit, you know, we failed at fundraising a couple times, and then we finally hit, you know, all it takes is that one.
(0:08:49) Scott: Yes. By the way, to make you sound like you’re a genius. And we had some great investors early on, and then it just sort of snowballed from there. And, you know, again, looking back on it, you don’t really realize how much of it was just like we had the tiger by the tail. We were holding on more than us being brilliant about, like what we were doing from a go to market perspective.
(0:09:08) Scott: And, you know, again, hindsight being 2020, I’ll never forget sitting down with Jeff Lawson, who was, was the CEO of Twilio and grew that to almost an $80 billion company and I sat down with him when we were kind of peers at the time. And he’s like, well, we’re doing SMS, you’re doing push notifications. It seems like we should put our two companies together.
(0:09:26) Scott: And I’m like, Jeff, let me tell you, you’re doing old school stuff. We’re doing the new, we’re going to, you know, and sure enough, he was way more precious than I ever was. And, you know, the thing that stuck to me that I still to this day will never forget is he said, you know, I said, well, SMS is going to be a kind of a dying, you know, way to send messages, push notifications are, you know, such a much more, you know, brilliant and elegant way to do this.
(0:09:52) Scott: And he’s like, yeah, SMS may go away. But man, I’m making half a penny all the way down to the bottom. And I was like for every message that they send and when you do the math on it, he was able to grow his top line revenue. Even if his margins weren’t killer. It didn’t matter. That allowed him to then, you know, raise money and grow the business so that he could consolidate.
(0:10:12) Scott: And guess what? They got into push notifications. They did all those things too. And so, you know, again, you kind of learn those things as you go. But you know, never, never a dull moment. So anyway, you know, and, you know, we’re seeing the same thing with case Mark now, like, it’s this we really feel like we have the tiger by the tail.
(0:10:28) Scott: Yeah. On the. And it’s just been it’s been a wild ride already, and we’re just we’re barely, you know, again, the paint’s barely drying on this thing, so.
(0:10:35) Courtney: Yeah, we’ll also sounds like you’re one thing that you have been really consistently is just scrappy. Just like do it, get it done. Like before the we don’t need like a big fancy website. We just need to we need people to be able to use the product and that focus on tech and like the product, it seems like a very product.
(0:10:52) Courtney: First, orientation with your company, which seems to have paid off pretty well for you. And what an exciting time to be like during these iPhone releases. Are you like, yeah, we do. We’ll do all the push notifications. And that’s I mean Amazon so exciting. Yeah.
(0:11:08) Scott: It was that was that was really that was really fun. I mean that was that was such a crazy time. And, you know, every new release of, of iOS that came out, we were like crossing our fingers that we weren’t going to be obsolete, you know, obsolete because like, you know, Apple, because that was always a concern from investors is that Apple will just launch something that does this.
(0:11:27) Scott: And thankfully, they never did because they said, no, we’re in the we’re in this sort of, you know, the network layer of this thing. We’re going to let people build services on top of that. And so we got, you know, we got really lucky in that sense. Yeah. Same thing is kind of true, you know, here what’s happening with AI and legal tech, too.
(0:11:44) Courtney: Yeah. So you’ve sold a couple of different companies across a couple of different industries. So, what made you decide that legal tech was the next frontier? It sounds like partially gut. What was there another thing that was telling you this?
(0:11:57) Scott: Oh, yeah. I mean, of course. Yeah. Again, you know, leave it to me every every time I start a new company, I do it a new vertical, which. Yeah, none of the network effects that I’ve built up with the networks that I built in. But, you know, at the same time, I just, I think I enjoy disruptive, disruptive technologies that are changing, you know, industries or remaking things.
(0:12:18) Scott: And to me, it’s that disruption or that that technology shift that is exciting. And it also just creates such huge opportunities. But the reason we picked legal tech is really, really simple. It’s because I’m married to an attorney. My wife, is an insurance defense attorney here in Oregon. She runs a practice. You know, they do Oregon, Washington and Idaho.
(0:12:37) Scott: So think like, you know, she’s got big retailers and she’s got, you know, like, Uber is one of her big customer or one of her big clients and all that kind of stuff. So, you know, she kind of jokingly said to us, you know, hey, if you’re going to start something new, why don’t you solve medical chronologies?
(0:12:52) Scott: And it’s it’s a hard it’s a hard problem in the sense that you get this big pile of medical records and, you know, you have somebody who’s suing you for potentially millions of dollars, and you need to make sense of that. So now they usually what they do is by hand, they’ll have an associate or a paralegal go through and sort all those and organize them.
(0:13:08) Scott: And then you have basically this work product that’s a word document that tells you, here’s the, you know, day by day, you know, what the treatment they had not only before any incident, but like after ongoing all of that and that can take you like, you know, weeks to do. I’ve seen some met crowns that people have invested, you know, close to, you know, three, 4 or 5 months and, and tens of thousands of dollars.
(0:13:31) Scott: If not more of paralegal time to do it. And so, so that was a big problem for us to kind of tackle. So instead what we did is we started with simpler solutions like deposition summaries, trial hearing and arbitration summaries, tax return summaries, police report summaries, those kinds of things. Again, really being work product driven because in this early, early stage, we knew that attorneys always have a hard time adopting technology.
(0:13:56) Scott: We’ve got 30 years of, you know, lack of technology adoption to show that. So how can we just make it ridiculously drop that simple and again, do this crawl, walk, run into what you know will ultimately be full case automation for us. And starting with the easy buttons was a great way to do it. In other words, they know how to upload a file, they know how to hit a button, and they they understand work product that is in a format that they are used to using.
(0:14:21) Scott: So let’s start there. And that’s kind of where that was the seed for it. That was we started that in June of 2023. And then, you know, really kind of hit our stride last year about, about this time actually about April, and that’s when we raised our pre-seed round from, gradient Cambridge and a couple other angels.
(0:14:39) Scott: And then we’ve just been kind of off to the races ever since.
(0:14:42) Courtney: Yeah. Well, so the your approach was not I’m going to solve this entire problem because I’m not going to solve every single element of this. But you kind of just picked like 1 or 2 things and then started gaining trust with lawyers and getting feedback. So like you said, just pick like one small problem and fix it. Well, is that kind of the approach that you’ve been taking?
(0:15:01) Scott: Yeah, 100%. And I think that’s that’s always a good way to approach it. I think the other thing that happens in these disruptive technology times, I mean, I think Bill gates kind of said it best, which is, you know, any time there’s a disruptive technology, no matter the vertical, we overestimate what will happen in the first two years.
(0:15:19) Scott: And we, we, you know, underestimate what will happen in ten years. And so I think I think that’s no more true than in legal tech. And everybody’s been saying, well, our AI is going to like replace all these attorneys. And and yet what we’re realizing is, wow, this is actually a great tool that augments what you do. It’s not about reducing headcount or lowering the billable hour or reducing your total billable hours.
(0:15:42) Scott: Really what it is, is how can you remove or reduce the tedium? How can you make it so that the backbone of these firms, the paralegals, the associates, the junior partners, how can you make it to those folks are moving to kind of this air traffic controller role where they can manage instead of 60 or 75 cases, let’s get them to 300 cases, but still give them this ability to like drive down from a granularity, you know, perspective to generate work product.
(0:16:07) Scott: Because so many of these AI solutions are kind of opaque, it’s like, yeah, upload your files. And then like, if you can navigate this complex, beautiful product, you might be able to do something with it. But you have to learn all those things. And instead we said, no, let’s, let’s solve from a work product standpoint and work our way up from there.
(0:16:24) Scott: And then and then ideally have this be a tool that, that makes it ridiculously easy for folks to, to handle more cases, because the one thing that isn’t covered in the mainstream media is about AI is I actually think it’s going to increase the amount of litigation. It’s so much easier for plaintiffs to be able to just ingest a bunch of data, spit out a demand letter, and then fired off than it was, you know, even two years ago.
(0:16:47) Scott: And what that means is there’s going to be an increase in the amount of litigation out there. So if you’re on the defense side, you’re going to have to have solutions for for doing that. And the way we see ourselves is, is we’re kind of arming both sides in this. It’s sort of like way back in the day.
(0:17:01) Scott: I’m dating myself, but the same company that made the radar guns for police also made radar detectors for. Yeah, like duh. Right. So. Right. So that was you know, we’re kind of doing the same thing here for, for folks. Yeah. It’s been good.
(0:17:17) Courtney: Interesting. Well, so in addition to like, you know, you’re making like, making these paralegals like, air traffic controllers, I feel like this also is probably reducing the human error, because if you’re just having someone, like, go through all of this information and then, like, translate it into a word doc, there’s no way that that’s like 100% accurate all the time.
(0:17:37) Courtney: So I imagine that’s also really helpful for these like attorneys and lawyers that you’re working with. But I also want to point out, like how smart it is to start with like something very simple and easy because legal, tech or legal, the legal industry is so slow to adopt technology. It’s almost kind of like giving them just like, just dip your toe and try this one little thing and see how it works, and then, you know, start to believe in it and see how useful it is before having them, like learning entire platform, like it’s exhausting, for sure.
(0:18:10) Scott: And I think, you know, early on the press kind of seized on, you know, some, some attorneys and some situations where folks had, you know, either I had hallucinated or the attorneys had, like, forgotten to remove, you know, simple things. Like, as an AI bot, I’m not like you. That’s an a pleading that was submitted to a court.
(0:18:29) Scott: Well, it doesn’t matter if I was involved in that, that attorney, those attorneys probably were doing all kinds of other shitty things without AI. Right. And so, you know, that ethical component is critical no matter what. Now, I will say the the you know, the solution is it’s a lot like self-driving cars in the sense that, you know, humans are actually more accident prone than most self-driving cars.
(0:18:52) Scott: Yeah, but the story is much more interesting if it’s a, you know, AI powered car that gets in an accident, unfortunately. Right. It just is. And so those stories around, you know, bad things happening with AI and legal are definitely there. And again, the way we frame it is we always tell our customers, look, you should still review this.
(0:19:09) Scott: The goal with this is to create a essentially a shortcut or streamline this. And then we give tools to help them trust in and verify the output. In other words, you know, for an example, if we do a deposition summary we’ll give you this page line output that explains each section that you see. But you have a little link there that allows you to like jump to the actual testimony so you can actually see the transcript and say, oh, cool, it actually does match up.
(0:19:33) Scott: That’s great. So they’ll spot check it and feel much better about it. But giving them that tool allows us to sort of bide our time as the industry, you know, really learns to trust these tools as they go through. And again, it doesn’t happen overnight. And so, you know, to the point that I said before around Jeff, Jeff Lawson and Twilio and, making money half a penny for every message that you know, is going out of style.
(0:19:58) Scott: Our thought was, well, if work product is, you know, going to be a thing of the past, why not make money every single time? Wallet. While we phase it out? And by the way, while we’re facing that out, we can ease people into using our solution this sort of full case automation component. So again, you know, it’s it’s to me it’s about not just solving the how do you get folks to adopt this, but how do you build a proper go to market motion such that you can sort of outcompete everybody else in the space?
(0:20:25) Scott: And I think that’s another one of the little challenges in this space that folks don’t talk about. It’s rarely has anything to do with product. Because we’re all working with the same tools. We all have access to the same labs. Yeah.
(0:20:38) Courtney: So I guess I kind of brings you back to your point about, you know, case mark is the iPhone moment for legal. So what do you feel like needs to happen for that to really, like, take off? Like what? What are we waiting for? Like, is there a light bulb moment for all these lawyers or is it a technology thing?
(0:20:56) Courtney: What do you think needs to happen?
(0:20:59) Scott: You know, honestly, it’s just it’s just going to be, it’s just going to be it’s going to take time. It’s literally going to take time for it. And these things take a long time to adopt. I mean, it’s really interesting because I when I, you know, I, I go and actually do trainings at offices, especially for firms that are, you know, larger firms.
(0:21:17) Scott: We’ll go in and do the training itself, especially if we’re close to them or if we’re in town. And it’s really fascinating to see the paralegals sit in front of a new tool and then when you see them actually use the tool, you’re like, oh, wow, we need to remove more features. And I literally had a session this morning with my, my product team and, our product designer talking about how we’re going to further simplify what we’re building because we need to always make sure that we can surface an easy button.
(0:21:46) Scott: Yes, there’s a way to drill down and get more features and functionality and optionality in there. But really, I got to be able to upload a file, click a button and get an output, and it’s got to be quick and it’s got to be understandable. No matter how many of those easy buttons that we have, we’re now getting to the point where you’ll be able to just drag in a file and we’ll suggest it, because we can look at the file with a high degree of accuracy will determine, oh, this is a deposition transcript view of some medical records.
(0:22:10) Scott: These are some billing records that just we can solve that and then just surface the button for them. And now oh great. I just hit that button. Awesome. That’s really worth seeing.
(0:22:19) Courtney: Yeah. Like I feel like, that it’s just the power of editing it because in tech you’re like, oh, I want to I want to be able to do all these amazing things and to to narrow it down to, okay, what how will this person actually use this thing? Like, let’s actually focus on that. And editing is like the hardest thing I think for, especially for like product developers when you want to make the coolest product possible.
(0:22:43) Courtney: So that’s really neat. And so it’s always kind of always up to how after you updating the product.
(0:22:49) Scott: Oh, constantly. We have a big release. We have product releases every Tuesday. But then we’re continuously iterating it, you know, sort of through our staging infrastructure and getting customers in front of it. And then, you know, just each of the easy buttons themselves or iterating in a different pace. And then, you know, we have all kinds of different versions of those as well.
(0:23:09) Scott: But I think the way that we’ve architected the platform allows us to be really nimble in that respect. We can spin up a new easy button really, really fast actually. And that’s actually been a huge advantage for us. And we have some things coming here, you know, towards the fall that I think are really going to accelerate that, you know, being able to generate a medical chronology for, you know, 25,000 pages of medical records and do that in under ten minutes.
(0:23:32) Scott: Like, that’s a huge game changer for folks. And, you know, it’s one that that we’re super, super excited about, mainly because we have so many that we have to do through, you know, our partners and law firms that are looking to do this, you know, looking to do, you know, thousands of these a month. And so, for us it’s a unique challenge, but it’s also one that, you know, shows us that we’re on, on the path towards product market fit.
(0:23:54) Courtney: Yeah. Well, and so you’re mostly in personal injury law, and obviously inspired by your way, which is lovely. But, is there any other reason for that focus is you just feel like, oh, this has the most opportunity, the fastest, or was there something else that kind of drew you there?
(0:24:11) Scott: No, I think it was really, having the subject matter expert, that’s my wife meant she was able to give us insights into what direction is coming and our first deposition summary. You know, she in the first couple versions, she absolutely eviscerated us on, and rightfully so, because they were they were subpar. And so once we started to learn from her, that helped us kind of move things forward.
(0:24:33) Scott: And again, you know, there are probably the sort of richer paths that we could go down. You know, some say, like just focusing on plaintiffs would make a lot more sense or in-house corporate counsel. But unless you have that subject matter expert and some path towards, you know, how you can drive momentum, it doesn’t matter if you’re sort of going after those big pieces.
(0:24:53) Scott: My take is if we can get momentum on the path that we’re on, then continue to augment and build the platform for both plaintiffs and defense, then we’ll start to see overlapping, you know, options for whether it’s employment law or, real estate or, you know, you name it. Like there’s a bunch of overlapping things that we can build these easy buttons for, that, you know, tell that story.
(0:25:14) Scott: And ultimately, what we’ll find that, that, you know, ideal path forward for us. But to me, again, having that, you know, that’s a team component. Having somebody who’s a subject matter expert was just such a huge differentiator for us. And so that’s why we followed that for sure.
(0:25:28) Courtney: Yeah. No, that’s I think that’s really good advice for anyone building a product for like a very niche area that they might not have direct experience in is pulling those people in early on so that you do get on the right track faster. That seems to have been like pretty impactful for you guys and the way that you develop the product.
(0:25:48) Scott: Well, yeah, without a doubt. I mean, she’s she’s been instrumental in everything we’ve done and even the Macrons that we generate now in the medical narratives. Those were instrumental, based on how she has built them for her and her team. We do those very similarly. And it turns out like a lot of the insurance carriers like that way as well.
(0:26:07) Scott: And so, you know, having those kinds of insight is, is just so critical. In the early stages of a company like this, it’s what just helps you get that flywheel going and then really, you know, sort of grow the business as fast as you can.
(0:26:20) Courtney: Me as well. So if we look ahead five years, which in tech language is like 30 years, I guess. Really? Where do you see case Mark going? Like what? What do you think is going to happen with case Mark and like, legal tech in general?
(0:26:34) Scott: I mean, I think I think in legal tech in general, what we’re seeing with AI and this is, you know, just thinking even more broader than just legal, you know, when I came out, everybody was like, oh my gosh, let’s slap AI on everything, right? So you’ve got AI customer support, you’ve got AI, you know, sales development reps, you’ve got AI, you know, website builders and all, like all these different things.
(0:26:55) Scott: And that’s phase one of this. Phase two to me is realizing, oh wait a minute, we can collab some of these operations into a single place now that I can handle it, because I is actually a core function. Those other things are just elements of what the core function should do. You know, a great example is, is, one of our friends, Amanda Carla, who runs, one mines.
(0:27:19) Scott: She’s got a really killer, AI basically, you know, avatar SDR that allows you to basically mine the long tail of your, your sales pipeline so you can now have somebody schedule a call. This I SDR can answer questions. It’s like a person, they can spin up a VM and you, they can do a demo of the product, the whole nine yards and it’s for those folks who just, you know, maybe you have 20,000 customers that are it just doesn’t make sense to throw a human at you can do it that way.
(0:27:47) Scott: And what they’re finding is, in addition to closing the sale, they’re also finding, oh, I can ask customer, you know, support questions. I can ask about my renewal. I can, like all these things kind of collapse into the single person or the single sort of technology. And so that’s, that’s really, really powerful. So I think the same thing is going to happen in legal tech.
(0:28:08) Scott: In other words, today a lot of people think about it from the technology standpoint. I have file sharing, I have case management, I have time tracking. The attorneys. Just look at it as I have a pile of data that involves this case. I need to generate work product and I need to answer questions. I need to do it at scale.
(0:28:27) Scott: Go right. They don’t care about it. Where is it? You know, where’s the file sharing? You know, how am I tracking the time? All those things. I mean, obviously they care about tracking time, but. Right. But the point is, the point is that that AI is going to condense a lot of these things such that, I think that you’re going to have or, you know, you’ll have a player that emerges in this space that will be, you know, just like when retail, print, TV, movies all sort of digitized out came on Amazon and Netflix, you know, those kinds of things.
(0:28:56) Scott: And I think there’s an opportunity for that next. You know, I think, a defining company of this category to actually emerge that’s in a, you know, sort of post digitized world. And I use the term digitized because legal never really digitized. It’s been fighting it tooth and nail for, for who knows how long. And again, that iPhone moment is AI and its impact on legal for sure.
(0:29:18) Courtney: Yeah I don’t think there’s like skipping over to the next like before they digitize everything that’s going straight to AI. Straight to case Mark. That’s I think that’s really interesting. And it’s almost like it’s too good of a deal for them to pass up. Like, it, it it will improve everything. Allow them to take on more. And like you said, that’s such a good point about there being more litigation with AI because it’s easier to be a plaintiff.
(0:29:46) Courtney: So that’ll be really interesting thing to, to watch for sure. Yeah.
(0:29:50) Scott: Yeah.
(0:29:51) Courtney: So kind of going back more to like your overall leadership style because you’ve built and sold so many successful companies. How is your leadership style evolved since you first started?
(0:30:04) Scott: Yeah. It’s interesting, I, I think I spent a lot of time trying to, figure out how everybody else was doing it and then try to do it like them. Yeah. Versus how do I want to do it? Or what do I think this is effective? Or what do I think resonates with my my team. And I think, you know, I’ll say because of my experience, not my age, that, that I’ve started to refine that more and more.
(0:30:27) Scott: And it’s interesting because we just went through this exercise, instead of doing a mission, vision and values exercise, we sort of tried something different. It’s actually one of our investors gave us the idea and helped us kind of lead through the, the process. And actually the results me was just phenomenal. And what did we do? We boiled down to basically what we call three operating principles.
(0:30:49) Scott: And it just it’s what helps us, you know, build a company that isn’t a family. It’s a team. In other words, we all depend on each other and we all have to be high performing. Otherwise we have to make changes, right? Just like any high performing team. But this, you know, these concepts around bias towards action, you know, being truly customer first and really passionate about those customers and so actually just threw up our new operating principles.
(0:31:12) Scott: I actually did a post about it today on LinkedIn. You know, I’ll probably end up on LinkedIn lunatics or something, but but I actually believe it. And, you know, I think the other testament, too, is, you know, we’ve got six folks of the 15 folks who work here at, case Mark now used to work for me at Urban Airship.
(0:31:28) Scott: And so me, it says that I’m doing something right to, you know, people wanting to work with me again. And but I’m always trying to refine that, too. It’s the same reason that, you know, I have I have, you know, three advisors that I check in with, you know, at least on a every other week basis or, you know, maybe monthly for some of them.
(0:31:44) Scott: But folks that help me stay focused and, you know, in touch with what I’m trying to build here, because it’s really easy to get into your own little mind space and think, oh, man, I’m brilliant, you know? And you know, you’re just not you’re you’re you’re kind of lucky and you’ve got a team that you’ve got to kind of shepherd through this thing.
(0:32:02) Scott: And, so it’s, it’s been kind of trying to navigate those things, but, you know, getting those operating principles and really focusing on that. I think it’s been really exciting. And I can’t believe I’m saying, wow, this is exciting, that we have operating principles, but, it just it, it resonates with us because it’s so pragmatic and it’s not like this.
(0:32:20) Scott: You know, I spent I don’t know how many hours trying to think through mission vision values for other companies, trying to, like, have this epiphany when, you know, really we just have a bunch of work to get done. Yeah. And, you know, honestly, people want to align on that. And that’s okay. So, you know, I think that’s kind of how I a little bit about how my, my, sort of leadership styles evolved over time.
(0:32:40) Scott: And, and it will continue to evolve for sure.
(0:32:42) Courtney: Yeah. Well, I like that. You’re like mission vision values, all that stuff. It works really well for some companies. But I think for, for high performers, which it sounds like that’s like the type of person that you hire. It’s like sometimes you need something different, maybe like that fluffy nice language doesn’t really inspire. But if I can, like, look at these, these, these operating principles and customer first.
(0:33:07) Courtney: Okay. Like that is something that I can apply in my job right now. And also that is like a feel good thing to be customer first. Not every company is. So I we did a similar thing where we kind of like we’re really trying to figure out like culture, values, mission, vision, all these different things we ended up doing even over statements, which was really helpful because that’s how you make it even over as like pursuing better, even over safe routine.
(0:33:32) Courtney: So we always know we want to be pushing for better. You’re never going to be punished for pushing for better learning more. And I think that it’s just it’s different for each company. So operating principles, that’s a good, good note probably for a lot of tech companies to.
(0:33:48) Scott: But I mean, honestly, a lot of it is, you know, I, I do, you know, a bunch of reading on, oh, we’re listening to podcasts and hear about ways that people are doing things. And I just sort of run it through my own filter. And sometimes I pick up little nuggets here and there that make a lot of sense for it.
(0:34:03) Scott: And so I try to grab those as best I can and then and then iterate on them. You know, the bias towards action that we lean into. That actually was something that came from Jacob Kaplan Moss, who was one of the founders of Django, which is a big open source, CMS and, and that just stuck with both Stephen and I, my co-founder.
(0:34:21) Scott: And it’s just been it’s been really good.
(0:34:24) Courtney: So building a product is one thing. That’s something that you’ve proven that you can do very well, but building a brand is a whole other ballgame. And I think this is where a lot of tech companies who are or product focused stumble. How do you think about the branding and the type of content that you should be creating for these companies to have, like a really strong go to market strategy?
(0:34:46) Scott: Yeah. That’s interesting. I, I, I’m the first one to tell you that I am horrible at building a brand or thinking about the brand, but I’m one of those, you know, great people who can be sitting up in the stands and go, oh, that’s an awful brand. Yeah, right. But, you know, and I don’t know why and I can’t quantify it.
(0:35:03) Scott: I can’t, you know, whatever. So so what I do is I, I lean into folks who are way smarter than me and way better at those things. I mean, let’s be honest, like we started a company called Urban Airship, for God’s sakes. It doesn’t exactly roll off your tongue. And the story around how we came up with the name is even crazier.
(0:35:19) Scott: We basically entered, you know, airship into a web 2.0 name generator, and the domain was available and we’re like, oh, that’s it. That’s the name of the company would like to do that. And but, you know, I kind of I try to lean into folks who are, you know, far more sort of brilliant than I am on it.
(0:35:37) Scott: And you can kind of see behind me this, this long board that’s hanging up on the wall. That’s an example of one of the urban airship, campaigns that we did. And we created these custom branded urban airship longboards. And at the time, Urban Airship was, you know, it was still early push was still early, but mobile was a big deal and everybody was talking about it.
(0:35:56) Scott: So getting in front of CMO was actually really hard, and they tended to be the ones with the buying power. And so, my CMO at the time, this guy named Brendan Gilkey, he came up with this idea of, let’s, let’s do this longboard and we’ll, we’ll make it custom. We’ll build a box for it, and we’ll put this wrapper on that says, your journey through mobile can be tricky.
(0:36:15) Scott: Let us be your ride. And then you open it up and there’s this really cool little, little car that says, hey, we scheduled a meeting with you next week, we’d love to catch up, blah, blah, blah. And I think we did 100 of those to start. And I think, you know, all in the camp, it was like 11,000 bucks.
(0:36:29) Scott: And I think it generated over a million an RR for us in the first year. And it was just one of those little things that like, was, you know, was a moment for us. And, and that helped us kind of build this brand around. And we sort of, you know, did some really fun things with that. And so I just try to lean into those things and, you know, we knew the term case mark itself from a company perspective.
(0:36:48) Scott: We were case mark. I and very quickly we realized, oh, wait a minute, this is going to actually be bigger than I. And that’s why we went and got the grant. Tom, I think the secondary, fact is that a lot of, a lot of law firm firewalls, filter out eye domains. So having a.com is actually really critical, especially one that isn’t, you know, it hasn’t been used as a spam, domain.
(0:37:13) Scott: Anyways. So so we ended up doing that. But but I mean, to me, it’s sort of the point is that we’re aspirational about what we’re thinking about this brand. You know, we ultimately want to become a verb as far as attorneys are thinking. In other words, wow, we got a new matter at Let’s Case Market. And what I mean there is point us at that folder.
(0:37:31) Scott: We’ll surface the transcripts, the pleadings, the medical records, the tax returns, you name it, we’ll give you that, you know, set of easy buttons that all the cards, set of easy buttons to generate work product. But we’ll also give you that case chronology. Well identify gaps in discovery and then give you a list of deadlines. Again, that allows these, you know, folks to move into that air traffic controller role.
(0:37:51) Scott: And that’s what, you know, gets me really, really excited about this. And we’re not there yet. But that’s the sort of the vision for the business moving forward.
(0:37:58) Courtney: Yeah. Amazing. Well, it sounds like you guys, when you approach your branding, it’s like thinking a little bit bigger, thinking a little bit further along. And I love doing kind of unexpected branding moments or marketing moments like sending along boards like that’s it’s just so cool because it’s something that they cannot ignore. That’s the thing is, like, you have to be uninsurable.
(0:38:19) Courtney: You have to just not be someone who’s sending 100 cold emails or, you know, just calling constantly because that’s what everyone is doing. So just doing something different, because your company is different, bigger. It’s interesting. It’s it’s different than anything else. So you might as well make your marketing different as well. I also I think you kind of talked a lot about making sure that your product is really usable.
(0:38:44) Courtney: So when you think about legal tech and making it really relatable, what is some advice that you would give to other founders in the legal tech industry about breaking in and making their tech more relatable for their consumer?
(0:38:59) Scott: I mean, I think, one of the one of the biggest things I see is so many people building product and not actually being in front of attorneys or building something they think attorneys want. But when you actually watch the sessions, especially if you’re not looking over their shoulder. Yeah. You’ll notice, like these angry clicks and people are confused.
(0:39:20) Scott: And, you know, you also have to put yourself in the seat of these folks. If I’m a paralegal and it’s Friday afternoon, I just want to get out of the office. I’m there, you know, I’m I’m trying to get done. And so how can you streamline that and make it really, really easy for them? And it’s not with some, you know, beautiful product that, you know, solves all these things.
(0:39:37) Scott: I mean, what’s really interesting is, is one of the big advantages for our platform is we deliver work product in the form of a word doc or a PDF. And that may sound really silly for folks, but the reality is that’s what a lot of these attorneys live in. So this idea that oh no no no, we could add a feature that inside of our web interface allows you to filter and do it.
(0:39:56) Scott: No no no no no no no no I don’t want that. Because here’s the deal I gotta take this deposition summary, print it out, put it in a binder. So this attorney over here can take a highlighter to it. Right. And we may not work like that, but guess what? That’s how they work. And that’s the most important thing.
(0:40:10) Scott: And I think people miss that when they’re building products. And so I think we’ll always try to lean into how can we delight the customer not only with how easy it is, but with how easy it is to get in touch with us, not just the AI, but like talk to a person. In that case, Marc and I think, you know, that’s a differentiator in the, in the market.
(0:40:30) Scott: And so, you know, advice wise, I would say talk to some actual attorneys separately, some people practicing who are going through this. And honestly, it’s the folks who are, you know, I I’ll say the the I want to say the bottom rung of the ladder because that sounds bad. But people who are new into, you know, law are grinding and learning like crazy.
(0:40:51) Scott: They’re the ones who sort of have the capacity or willingness to want to sort of share if they can. And then I think, you know, longer term, we’re going to see a, this evolution of the law firm itself. I think it’s going to change over the next decade. I don’t know where it’s going to go, but it’s definitely going to be an opportunity for younger attorneys to be able to build and carve out their own, you know, practices much easier and faster than it is, like trying to fight tooth and nail to get that partnership that, at a law firm, you know, over the long haul.
(0:41:18) Courtney: Yeah. Well, you’re kind of talking a little bit about behavior. And asking someone to change behavior is like getting people to change their general behaviors so hard. So what you’re saying is, instead of asking them to change every element of their behavior of like how they use these documents is like, let’s let’s let them highlight sell, because that’s not going to be something they’re going to want to change.
(0:41:38) Courtney: Let’s just like do this, this one little thing of how they actually process the data. And then everything else can stay the same. And that’s really smart, because I don’t think that you’re going to get some of these attorneys who have been, you know, doing law for 40 or 50 years to to put their highlighters down and like, log in to an account.
(0:41:58) Courtney: Yeah, that’s pretty good advice. Well, if you were going back to look at, to give yourself advice when you were just starting case. Marc, is there anything that you would do differently or is there anything that you wish you could have told yourself when you were starting out?
(0:42:12) Scott: I mean, not really. I mean, the reality is every company I’ve started, if I had known what I know now, what I knew, then, I probably wouldn’t have started it. I think that probably one of the reasons why most people don’t start companies is they think they, or I shouldn’t say they think they know too much. They they think they know that they know so much about the space, that they think that it’d be really, really hard to do.
(0:42:33) Scott: And it and it is hard, don’t get me wrong. But if you can just find that one thing, that one little beach head that one little hook, like in our case with depositions, summaries, you know, when I took that out and started, you know, trying to raise money on a seed round, you know, our pre-seed last year at this time, you know, folks are like.
(0:42:51) Scott: Yeah, but deposition summaries aren’t a big business. So I’m like, yeah, I know, absolutely. But what we’re proving are these easy buttons, and we’ll figure it out from there. But what we do have is people are clicking that easy button a lot for deposition summary. So can we make them click more across this entire litigation lifecycle. And so, you know, I mean, that’s that’s the leap that I think a lot of folks don’t make.
(0:43:12) Scott: And then we’ve just kind of been, you know, building this sort of, you know, vision for the, for the, you know, where we get with full case automation, over time. And then the question is cool, you have this vision out here. The magic is in how you get from here. They sort of crawl to the walk and then to the run, and it’s this big, crazy, long, circuitous path to get there.
(0:43:32) Scott: Although, you know, unfortunately, the way that it’s always, you know, painted in the, in the media is like, oh, brilliance every step of the way. And it’s like, no, really. Harvard, and we kind of tripped over ourselves, you know, trying to trying to figure this stuff out. But, you know, sometimes you get lucky and sometimes you don’t.
(0:43:48) Scott: But even can you take the times that you step backwards as a chance to potentially move the business forward because a step backwards, you know, could be because you read the market wrong, and that’s actually a good sign. So now you can tweak and rethink what you’re doing.
(0:44:01) Courtney: Right? Right. The obstacle is the way right. Like that’s the there’s always a there is always a solution to every problem is always some kind of solution. Well, thank you so much for coming on the show, Scott. It’s been really great speaking with you. Can you tell people where to find casework and where to find you online?
(0:44:19) Scott: Absolutely. So we’re just case mark com we did get that.com domain and you and, and then I’m just, you know, Scott at or. Sorry Scott at case mark.com. Feel free to reach out if you have any questions or you know, want to learn more.
(0:44:35) Courtney: Amazing. Well, definitely follow Scott on LinkedIn because it sounds like he’s posting some crazy stuff these days. And thank you to everyone at home or on the go for listening. And if you enjoyed today’s episode, please make sure to subscribe, share it with a friend or leave us a review. And if there’s anything you’d like to hear on an upcoming episode, just let us know.
(0:44:54) Courtney: For more insights and stories, please follow us on LinkedIn or visit Right Left agency.com and we’ll be back next time with more stories of success, innovation and marketing strategies to help you grow. See you on the next one.
