Talking with Casey Kuhlman, the CEO of Monax, an agreement management platform, at the 2018 Legal Geek Conference.

Kevin O’Keefe: I’m here with Casey Kuhlman. You’re the founder of– what’s the name of the company?

Casey Kuhlman: Monax.

Kevin O’Keefe: Monax. What does Monax do?

Casey Kuhlman: We’re a user interface and integration provider over a soon-to-be-launched blockchain ecosystem called the Agreements Network.

Kevin O’Keefe: And that’s a mouthful. When I go to conferences and people are talking about blockchain, it gives me a headache after a while but I try to understand it. Describe that to a person if you’re sitting in a pub, saying this is what we’re going to be able to do with this solution, For a lawyer that’s really unfamiliar with the concept.

Continue Reading Casey Kuhlman, CEO of Monax, on His Incredible Journey to Founding a Legal Tech Startup

Talking with Garth Watson, the co-founder of Libryo, an online legal compliance software, at the 2018 Legal Geek Conference.

Kevin O’Keefe: You’re the founder of Libryo. What is Libryo?

Garth Watson: Libryo is an online platform typically used by global companies that have diverse operations and they use it to know the specific regulations that they face at each of those distinct operations.

Kevin O’Keefe: How’d you get started doing that?

Garth Watson: That’s a good question. It’s a series of opportunities, really. I co-founded a consultancy that helps companies with management systems and legal compliance, and together with my co-founder and CEO of Libryo Peter Flynn, we developed a web based system which we call the Libryo MVP.

Continue Reading Garth Watson, Co-Founder of Libryo, on the Exhilaration of Launching a Legal Tech Startup

It’s been a busy past few months for LexBlog’s  Legal Tech Founders Series.

Since LexBlog began this journey back at ILTACON, we’ve interviewed many founders throughout the legal technology industry, diving deep into the personal stories. We’re looking forward to continuing our mission to shine a spotlight on the good work legal entrepreneurs are doing around the world.

That being said, we’re excited to move the Legal Tech Founders Series to the Legal Geek conference this Wednesday. We’ll be interviewing several founders from companies both in the US and Europe, including Monax, Kira Systems, and Digitory Legal, to name a few.

Check in throughout Wednesday and Thursday to see individual interviews with these founders and hear their stories. CEO Kevin O’Keefe will also be tweeting his experience throughout the conference – if you’re interested, give him a follow @kevinokeefe or follow the hashtag #LegalTechFounders.

Attending Legal Geek 2018 and interested in doing an interview? Contact Caroline Hess at

Are you a London-based intern or law clerk who is interested in attending the Legal Geek Conference tomorrow – all for free? LexBlog CEO Kevin O’Keefe is in need of someone to assist with conducting LexBlog’s Legal Tech Founders Series interviews during the conference.

If you or someone you know is interested in this fantastic opportunity, contact Caroline Hess at or reach out to her via Twitter (@metskerce) as soon as possible.

Talking with Tom Boyle, co-founder of TrustBooks, trust accounting software for small law firms, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

Tom Boyle: Tom Boyle here, one of the co-founders of TrustBooks.

Kevin O’Keefe: What does TrustBooks do?

Tom Boyle: We’re helping attorneys easily manage their trust account, while staying in compliance with their state bar.

Kevin O’Keefe: When did this all start yet?

Tom Boyle: Really, the conception was my conception. I’m a CPA and had a CPA practice, and was working almost exclusively with law firms and one of the very first questions you get when you go into pitch your service to a law firm, and you’re an accountant, is to say, do you know, trust accounting? So I had to come back with a real strong “absolutely.” Which led to becoming an expert like that. And I was using the products that exist that most small law firms use: Quickbooks, Excel. I was actually using both, to try and get a complete picture for the trust account, and just thought there’s gotta be something better. This is a pain point. These products aren’t built for trust accounting. And so that was the start, that was the conception of TrustBooks.

Continue Reading Tom Boyle, Co-Founder of TrustBooks, on Always “Being On” as an Entrepreneur

Speaking with Keith Lee, founder of LawyerSmack, a private online community for lawyers, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

Keith Lee: I am Keith Lee

Kevin O’Keefe: As far as we know.

Keith Lee: Yes, I have the badge. So it’s official.

Kevin O’Keefe: Keith, what do you do now? I mean, you’ve been a lawyer, maybe you’re still a lawyer, lawyer?

Keith Lee: Lawyer-ish. I have lawyer-like qualities still at this point.

Kevin O’Keefe: And you started something called LawyerSmack?

Keith Lee: Yeah, so years ago, I started Associates Mind blogging years ago. I wrote for Above The Law for a number of years. We know a bunch of the old same old jerk lawyers from back in the day, but about two years ago I started LawyerSmack, which is a private lawyer community.

Kevin O’Keefe: What made you do that? I mean, it’s not like you’re sitting there going, okay, I got to go create something. What motivated you to do it?

Keith Lee: From having a blog, a popular blog, for years, it was fun having an audience, and I appreciated the conversation. The back and forth you get, particularly back in the day when blogs were initially there and everyone was really interactive, it was really cool. Social media sucked the air out of that in a big way, and I wanted to continue to reach people, but I kind of realized my limitations in that I only have so much spectrum of output. I can’t be talking all the time and I thought, you know what, there’s probably an opportunity to create a cool space to foster good communications between lawyers to talk shop, or just have a social media space, because I guess the thing is lawyers can’t talk shop on social media. You’re not going to like actually be vulnerable in public. Right? You’re like, oh, I don’t know how to do that. As a lawyer, a lot of marketing yourself is confidence.

Kevin O’Keefe: Well, most lawyers will not. Some of the better lawyers will do it.

Keith Lee: We did a million messages last year we’re at like 730,000 messages this year, people are really eager to talk about their practices and what they’re doing, but they want a private space. Bar associations have existed for years.

Kevin O’Keefe: And, and the simplicity of what you did – you did it on what platform?

Keith Lee: Slack.

Kevin O’Keefe: Yeah. So you’ve got slack and it exists already, and you go out and do it. How did people hear about this thing?

Keith Lee: I’ve done nothing. We’ve talked about it in January of this year, where we were at Legal Week and that was when I was kind of initially doing it. And I think it’s just been. I guess I have the benefit of having a reputation. I’ve been in and around the industry for 10 years now, so that helped put it forward. I’m very big on Twitter. Like I do a lot on Twitter. That’s my thing. I don’t like Facebook. Not that it’s bad, but it’s just not where my people are. And I just used that and it’s just organically grown.

Kevin O’Keefe: What’s the business model for it now? Because now you’re, you’re developing a business around it, or you’re testing what it could be.

Keith Lee: Yeah, so there’s a membership fee to join. So lawyers pay to join. It’s a very nominal fee. It’s on sale right now during the conference for $80 but it’s $139 a year. So it’s just this flat fee to get in. Everyone can communicate, but then yes, there are also vendors who we partner with, so they can then provide deals and discounts and services to members.

Kevin O’Keefe: And so they’re sponsored members?

Keith Lee: Yeah, they’re sponsoring members, so they pay an increased fee.

Kevin O’Keefe: So what do you envision, fo where this thing could go?

Keith Lee: I don’t know yet. You know, there is a desperate need for lawyers to communicate and connect. Particularly in two areas: there’s lots of solo and small firm people because they are by themselves somewhere and they don’t have a water cooler, right? They want to talk to people and their bar associations are not serving their needs. I’m sorry, I mean as someone who’s been in leadership positions with the ABA and with my state bar and everything, they’re just not nimble enough and they’re not meeting the needs, particularly of the younger lawyers, of how they want to collaborate and communicate. So I mean, I think it’s just going to continue to grow into this group of lawyers. I have members from all around the world – we have members from Japan, Australia.

Kevin O’Keefe: Do you envision at some point in time that you knew would have sub-groups of people if they want to or different things like that?

Keith Lee: Oh sure. Yeah, I mean there’s like 100 channels. There are people who don’t leave – I know there are a bunch of IP lawyers who only hang out in IP channel and that’s it. They don’t go anywhere else, or there are people who hang out in just the solo group and then, like, sports.

Kevin O’Keefe: This is almost like the old listserv days where somebody goes in and puts in a comment, it goes out to everybody and people can carry on a conversation.

Keith Lee: Yeah, except it’s much more organized, way more structured. The thing is, listservs were actually a really poor way to facilitate conversation. It worked, but there’s a way better way to do it. And that’s what we’ve done.

Kevin O’Keefe: How many people do you have participating now?

Keith Lee: Just over 300.

Kevin O’Keefe: And when you started it, how long ago?

Keith Lee: I started it right at the beginning of 2017 for free, totally open. And we ended 2017 with about 800 members, and we had done about a million messages and then I kicked everyone out and I said, “no, we’re doing this over again.” A real name, real face, no secret identities, have to have skin in the game, ie pay, just to try and elevate the whole conversation. And then since January we’re 50 percent back know almost halfway through the year and at the same volume of messages, so less people, but same amount of engagement and much higher quality conversations.

Kevin O’Keefe: What you’re forming is an online community of people that begin to trust each other.

Keith Lee: Yes.

Kevin O’Keefe: And with that communication, that town hall across the world. I can see where sponsors are going to look at that and realize it’s a good audience, and they trust Keith enough to appreciate what he set out. We can go to him and we’ll see what happens by sponsoring different things. And then you’re giving them shout-outs, I assume.

Keith Lee: Yeah. There’s this whole package, but like here at the conference, people I don’t know, companies I don’t know they’re like, “hey, you’re Keith, right?” And I’m like, “yeah,” they’re like, “we want to talk about being a partner with you,” because obviously I have this group of lawyers who are heavily engaged, they’re technologically savvy, they’re first mover type lawyers.

Kevin O’Keefe: They’re more likely to be the receptive to new ideas, new products. Are you still practicing law?

Keith Lee: Less and less. This is eating up a lot of my time at this point. At the beginning of this year I was there doing it more.

Kevin O’Keefe: When do you think it’s going to tip to the point where you go, “okay, this can support me.”

Keith Lee: It might not be much longer, realistically. I mean it’s getting pretty close to there. I mean, I love it. I love lawyers. I mean, that’s why I started writing blogs. It’s like I just love being around other lawyers. I love hearing about how well you practice, what they do and I have a real soft spot for having conversations and helping and interacting with lawyers and this is kind of, I feel like everything I’ve done up to this point, not in my pure legal career, but the blogging, the writing books, leadership stuff, this is the culmination. Like, oh, this is what I was supposed to do actually, is to make this place for lawyers. And it’s not about me, I just need to create the space, and then let everyone get together and help each other.

Kevin O’Keefe: You’re opening up the hall. And allowing that to happen, empowering the conversation. What do you tell lawyers that are practicing, they’re here, they’re somewhat innovative and at Clio and they’re hearing an awful lot about people that quit their job and went out and started something.

Keith Lee: And there’s a lot of that going around here.

Kevin O’Keefe: I mean, it’s in the water, like amongst people here, and they’re trying to figure out should I do that, or chase that down? And then you’ve seen a lot of those lawyers over the years. What do you tell lawyers who got this idea? What do you tell them?

Keith Lee: Don’t quit your day job. I mean, I think particularly there is this idea now, not just here, but kind of in the general ether, of the world of having side hustles and diversifying your portfolio of your life. Are you all eggs in one basket or should you try different things? To take it way back, a decade ago, that’s why I started my blog initially. I was like okay, I need to have some ways to try and build and develop a reputation and connect with other people outside of just where I live and practice as a lawyer. I wasn’t like, “Oh, I’m going to go start a blog and make lots of money.” But people should try things. I mean, look, you’ve got a limited amount of time in your life. You know, why not take risks? I mean, this is not a rehearsal, right? If you have an interest in something, go after it. Be smart, make smart decisions, take smart risks, you know, don’t burn everything, don’t burn your bridges and quit your job and do everything and just try and dive in, but, you know, test the waters. I mean, that’s okay.

Speaking with Nicole Bradick, founder of Theory and Principle, which works with clients globally to build web and mobile applications designed to change the legal industry., at Clio Cloud Conference 2018.

Kevin O’Keefe: So who am I talking with?

Nicole Bradick: I’m Nicole Bradick. I’m a former attorney and I own a company called Theory and Principle and we build, we design and build digital products for the legal industry. Web, or mobile applications, that sort of thing.

Kevin O’Keefe: How’d you get the idea to go off and do that? How long have you been doing it?

Nicole Bradick: So this is my third company in the legal technology, legal innovation space. So I’ve been around the block and I think when you pay a lot of attention to this industry, you naturally see the open opportunities and this one was pretty clear one because there was no shop that was focused on the legal space and this space is desperately in need of good design and good user experience and good user interface for our products. So that’s sort of the opening that we see to help people build better, more usable products.

Kevin O’Keefe: How’d you get started when you were out there doing other stuff, you’ve got another company you’re working with, and got this idea: How’d you get it off the ground and just get it started?

Nicole Bradick: The barrier of entry to starting a company right now is very low, because you need to have an idea, you need to have a voice, you need to have business acumen, but you don’t really need a lot of money. Like, I didn’t need to go out and fundraise to start this company. I didn’t need to go out and, and find clients because I already had a name in this space. So we started day one and our biggest challenge was that we already had clients and were working from day one on products, and still had to sort of build the rest of the company: all the processes and all of our strategy work had to be built around actual work that we’re doing for clients.

Kevin O’Keefe: The type of work you guys are doing right now is development of products for law firms? Development of apps for law firms? What is it?

Nicole Bradick: Yes. And so our clients range is pretty broad, so we’re legal industry specific, but there’s so many corners of legal industry. So we work with large law firms, typically they’re trying to build apps to get to their clients as value add products or as lead generation products. That could be a native app, that could be a mobile app, that could be a web application. We work with other legal tech companies who have existing products to help them improve their user experience design, their user interface design. We can re-skin products that are fully functional on the back end, but just need a refresh on the front end. And then we work with foundations on the justice side. So there’s a lot of products being built that are aimed to bring access to justice, or help us to leverage technology to make the law more accessible. So we’ll work with foundations to build these end-to-end products. But we also do early workshops with law firms who are just thinking like, alright, so we have a new innovation team –

Kevin O’Keefe: Who is we?

Nicole Bradick: It’s my company, but I have a team of designers, a team of engineers, I have project managers. We’re sort of a full service product team.

Kevin O’Keefe: You’re based in Portland. Is the whole team based in Portland?

Nicole Bradick: Yeah, everybody’s in Portland and we do have some people, we have one engineer who lives in the mountains and he comes in once a week, but we’re all in Portland so we do a lot of traveling. We don’t have clients where we are, so we travel.

Kevin O’Keefe: How important is it for you now, or was it when you came up with the idea to start this, that people knew you?

Nicole Bradick: It’s extremely important because this is a trust business. It truly is because a lot of our clients, it’s the first time they’re building a product or it’s a bet the farm type, like, you know, we’re a smaller firm, but we’re going to dump a lot of money because building products is really expensive. So it’s a trust-based business and I think the fact that people know me, I think they know that I’m legitimate and I understand what I’m doing and I’m competent and I know this space very well. I think that’s been huge both for pipeline building, but then also for actually servicing our clients.

Kevin O’Keefe: It’s a trust business, it’s huge. Lawyers are paid to be suspect of other people, it’s what we do for clients, so that trust factor is huge. Your business is off and running pretty well right now. Did you know right away that this was going to work for sure?

Nicole Bradick: I got very early validation on this concept. I had been building products on my own, at my last company too, and so I knew the market, but very early on I was having conversations. I’m doing a lot of market interviews and I was hearing people say back to me our value proposition. Like, before I even explained the value proposition, people were saying, “Oh yeah, I would love to use you because you have this industry expertise, I don’t have to explain things to you, you can help better with strategy because you know the market.” You know, people are really finding a lot of value in the design side, but they don’t have the design resources. So we had almost instant validation.

Kevin O’Keefe: One question I wanted to ask you, and it’s a society issue, the number of women leading legal tech companies is… How many?

Nicole Bradick: We have a group, and we all support each other, and there’s only maybe a dozen of us.

Kevin O’Keefe: I would’ve guessed five or something. Maybe it’s obvious with the way the law has functioned, etc. but why do you believe that’s the case? What do you see needing to happen? Maybe it’s obvious. Why do you believe that’s the case? What do you see happening?

Nicole Bradick: The biggest challenge, I think the biggest thing that needs to happen is that law firms, legal tech companies, people in this space need to start buying products or hiring companies that are women-led. And I think that’s very hard because most of the clients we’re dealing with are men, and it’s just more comfortable for them to hire another man. It’s foundation psychology, right? Like you’re more comfortable with somebody who looks like you, and I think that’s a business development challenge for me, because I am the face of our company and I think that, you know, even if it’s not explicitly, “I don’t want to work with a woman,” I think it’s much easier for them to hire a man. And so I think that the buyers need to take a leap and they need to be willing to buy from women, so that other women can see that you can really be successful doing this. Because it’s rough. I’m not going to sugarcoat it. We have a support group, because we need a support group, because we see some ugly stuff. We need success stories is what we need.

Kevin O’Keefe: A lot of it I feel is the same lip service from law firms, because if it came down to it it’d be like 2 or 3% of women are leading major law firms. But inside the tech industry, how important is it for companies to hire women and get women in leadership positions? Just like we would be pushing law firms to do the same thing?

Nicole Bradick: Yeah, I mean I think it’s very important. And I think if we look right now at some of the legal tech companies, like the SAaS companies with the biggest trajectory, their leadership is mostly men, and a lot of them have zero women on their leadership team. And so we’re not going to build leaders. We’re not going to build people to then branch off and start their own companies and that’s how these leaders are built, so it’s absolutely critical and it’s just not happening.

Kevin O’Keefe: What has to happen? The leaders of the company have to get outside of their comfort zone and hire women, as opposed to another person who’s like them, or as opposed to someone who’s already on their leadership team.

Nicole Bradick: Yeah. And my wish is that we can get beyond the point where we’re always talking about this. I feel like I have to be an advocate for women in this space, and so I have to be out talking about it, but really what I want to be talking about is my company and our products, and it’s so hard to get there because there’s so much other work to be done.

Kevin O’Keefe: We talked about it in the 70s, we talked about it in the 80s. And everybody’s talking about making progress, and I used to wonder whether we should be talking about it or not, because that’s highlighting something that should be behind us. I hope people won’t do this forever. I know it sounds stupid, but I’m sitting here thinking, who are legal tech founders who are women? I’ve got to make sure that I reach out to interview them. Maybe that’s stupid that I’m even thinking of that.

Nicole Bradick: Yeah, but that’s better than not acknowledging it, because it’s easy to forget.

Kevin O’Keefe: We’re here at Clio, and you’ve been out doing stuff, founding things, being a part of initiatives. You have a strong name for that, but for the lawyers who haven’t got outside of practicing law but are looking at breaking some type of wall at one of these companies, what do you tell them?

Nicole Bradick: So I think that that leap is a big leap for a lot of people to make. I’m a big advocate of the lean startup methodology of taking baby steps. So at any time I talked to somebody who’s thinking about starting a company, it’s always, “make a baby, baby prototype, and go out and talk to people about it.” And not only will you get customer value evaluation and find out if there’s a product market fit, but also you’ll find out if it’s a fit for you. Do you want to be out there hustling and pounding the pavement, selling software? It’s a very different life than selling legal services, where there’s an existing demand, but a lot of times in software we’re creating demand. It’s a fundamentally different lifestyle. It’s an exhausting lifestyle. And so I think if you can sort of make a baby prototype and go out and test it and live that lifestyle for a little bit, then I think it’ll be to decide if that’s the path to go down.

Kevin O’Keefe: You’re the first person to mention the side of “what if it isn’t right for you.” And you’re right. Would I feel comfortable going out and selling my service? Would I be comfortable getting critiques on prototypes and being vulnerable on these types of things.

Nicole Bradick: And there’s a tremendous learning curve, right? When I started my first company after practicing law, people would always be like, “oh, you’re learning how to code?” No, I need to learn how to run a business and that’s not something I ever learned in law school. So with my first company, I spent that whole company making basic business mistakes and backfilling knowledge and filling that knowledge gap of how to run a company.

Kevin O’Keefe: What made you say, “okay, I’ve got to figure out, how to run a company?”

Nicole Bradick: It was interesting. In the design discipline, we talk a lot about constraints and the benefits of constraints. So I live in Portland, Maine, which is not a hotbed of activity, and I was not happy practicing law anymore. I didn’t have very many options. So that made me start to think creatively about what I could do there, what gapsI could fill in the space? Then I can run from here, but still have a national company. So I was forced into it and I’m really glad I was. So that constraint was a blessing.

Kevin O’Keefe: How long ago was that?

Nicole Bradick: It was my first company, which started in 2011, 2010, something like that.

Kevin O’Keefe: Pretty good amount of years. I’m sure it feels like a long time now. When you think about what you’ve accomplished and running a successful that’s based on your name and trust, that’s impressive.

Nicole Bradick: I’m very grateful and I think I have the best job and I work with the best people I could ever imagine.

Chatting with Kristin Tyler, co-founder of LAWCLERK, a nationwide market for legal services, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

Kristin Tyler: Kristin Tyler.

Kevin O’Keefe: You do what?

Kristin Tyler: I am one of the co-founders of LAWCLERK.

Kevin O’Keefe: And what does LAWCLERK do?

Kristin Tyler: I’m so glad you asked. LAWCLERK helps connect busy attorneys with our nationwide network of freelance lawyers that we call law clerks that the busy attorneys can hire on demand, when they need an extra set of hands around the office.

Kevin O’Keefe: How’d you come up with that idea?

Kristin Tyler: Great question. So the idea for LAWCLERK came out about three years ago after myself and two of my fellow co-founders, who are also partners at my law firm. We had left a larger regional firm where we had 50 plus attorneys with all different areas of expertise and skill level, and we loved the ability to walk down the hall and ask an employment law attorney a question that came up on a different litigation matter, and be able to tap into their knowledge bank and get instant answers. And so when we left and went to the smaller firm, the idea came about, well, you know, isn’t there a way with technology that we can do something similar to still tap into that subject matter expertise and make it easier for all attorneys to find experts, or to find help in general, when they need it?

Kevin O’Keefe: So are you still practicing law or not?

Kristin Tyler: A teeny, tiny bit, yes. I love being a lawyer. I’m an estate and trust lawyer. I love my clients and it’s a pleasure to get to help them.

Kevin O’Keefe: So you’re practicing law, but are your other two co-founders still practicing law too?

Kristin Tyler: A little bit, yes. LAWCLERK just launched in January.

Kevin O’Keefe: Now I get it. The idea came around earlier, but just launched.

Kristin Tyler: Yes.

Kevin O’Keefe: What did it take to get it launched? So you’re sitting there practicing law, and obviously it’s not going to be done on a legal pad. What did you have to do to get it launched?

Kristin Tyler: So, after I had the idea, I spent a considerable amount of time reviewing each state’s ethics rules and the ABA model rules to figure out a way to build the system to be fully compliant with the rules. Because that’s, obviously, the number one question we get off the bat – how is this compliant? And we love to tell people the answer and if you want to know more, we have a 105-page white paper on the site that goes through it in nitty gritty detail. So that took about a year to really think it through, how it could work to be compliant. Once that was done, the next task was defining the right technology partner, the right developer, to help us build it. And so we spent at least another six months trying to find that person. And we did. We found a great team.

Kevin O’Keefe: How’d you find them? Because everybody has that question, because they’re lawyers, business people, accountants, not tech people, but they’re going to start something that’s founded on legal technology.

Kristin Tyler: So, luckily one of my cofounders had had some experience with a couple of different tech companies, through some bankruptcy cases and learned some do’s and don’ts. And so we applied that in our own search. We’re an outsourcing company, so we outsource, we work with people remotely all the time, but we did require a developer that would be in our office, in person, at least two days a week to talk about it and monitor the build process. That was a key factor. So once we found that person, we raised some money and built the site. Luckily we had our own test kitchen, with our firm, where we could test out some issues and work out some kinks. We obviously had some moments where it was like, oh my gosh, why didn’t we think of that? So we’d go in and improve it. We’re constantly adding features to try to improve it and make it a more streamlined process.

Kevin O’Keefe: Who funded it?

Kristin Tyler: Self-funded – friends and family.

Kevin O’Keefe: What do you like about that? Or what do you dislike about that? Or maybe you have no feelings about it, just had to get done.

Kristin Tyler: I think it’s really exciting that the people that invested in it, they said they believed in us, they believe in the idea. That of course was very humbling and also gives you a tremendous sense of responsibility of “we got to work really hard to make this thing become a real company,” and that’s what we are doing every day.

Kevin O’Keefe: So you just launched in January, but you’ve been working on it for a period of time before that. What were the high points for you? Was there a moment where you go, this is gonna work for sure?

Kristin Tyler: Our big official launch was kind of at the ABA TechShow in Chicago in March and I will never forget – we had a ton of attorneys sign up and register because there’s no sign up fee, there’s no monthly fee, so it’s super easy to become a part of our system. But we had one attorney in particular, he immediately on his own proceeded to post a project from the floor, from our booth in the middle of ABA TechShow, and we were like, oh my gosh, this is so cool. And that was one of those moments where it was like, this is gonna work.

Kevin O’Keefe: Have there been times when you’ve had that low point, and wondered if you were going to be able to pull it off?

Kristin Tyler: Oh sure. I think every company goes through those those days where you’re just like, oh my gosh, you know, we never thought of this challenge. I mean we have a really good success rate on our projects – over 98 percent, but you have a handful that go wrong because life happens, and a freelancer gets sick, or a freelancer has a death in the family, and you’ve got to hustle and scramble at those. And those are stressful times because we’re committed to getting good work product for our attorneys.

Kevin O’Keefe: What are your responsibilities? Obviously life has changed from being a practicing lawyer.

Kristin Tyler: Yeah. Yeah. So I get to do a lot of super creative work. I kind of help oversee the, I guess you’d call it marketing and sales functions, so for me, my number one favorite thing is to go out and talk to lawyers about LAWCLERK, and so I love being at these events. I love meeting new lawyers, helping introduce them to a new way to practice law, and get things done, and it’s super exciting for me.

Kevin O’Keefe: So you’re handling the marketing and business development side?

Kristin Tyler: Yeah, that is my responsibility, yes.

Kevin O’Keefe: What is your hope? Where do you envision yourself two years from now, three years from now, four years from now? What’s your hope? What’s your vision?

Kristin Tyler: I guess my non-financial hope is that we really can help a lot of lawyers, you know, this is a tough profession. It’s stressful. And by helping build our lawyers, I mean both sides of the spectrum. So the people who maybe, for whatever reason, need to pick up some extra work. We have people that are government lawyers or work for nonprofits and they need to pick up some extra money to pay for kids’ braces or something. This is another way they can moonlight, pick up some extra work to do those things. I mean, unless a lawyer wants to go drive Uber, what else are they going to do? I love that we can help people who are maybe stay at home parents or are caring for elderly parents that are sick, or are military spouses. We have a lot of amazing freelancers that have extra capacity to do work and we’re helping connect them with people they would otherwise never meet, to get that done. On the flip side, the busy attorneys who are staying up working until two, three in the morning, burning the candle at both ends. Some people want to live life that way. I don’t. And so we’re trying to give them more resources

Kevin O’Keefe: What’s the business model? So the lawyers can come in, sign up, put in a description of what they do, what their availability is, and that costs them nothing?

Kristin Tyler: Correct. No fee to be a part of the marketplace, and put yourself out there and market yourself being available for work.

Kevin O’Keefe: Like you said, what are your alternatives for doing other part time work? The last study that came out said that the number of lawyers doing part time work in Chicago was about a third. Now with LAWCLERK they can be called upon to do various types things.

Kristin Tyler: Doc review – I mean, any lawyer can do that – general research, any lawyer can dig into an issue, and research it, and give you a memo, and analyze the issue.

Kevin O’Keefe: Now on the other side a lawyer that’s working until two in the morning, or the firm with 100 lawyers, but they need some particular expertise. So they come into the system. What’s the business model and the relationship with you and them?

Kristin Tyler: So they sign up, create their account. Again, no fee, no monthly fee. Let’s say they post that they need a motion for summary judgment and they’re willing to pay a thousand dollars. They pay that flat fee price, because it’s all done on a flat fee, and the hiring attorney names the price. We take a commission on the transaction as our payment, and the net amount goes to the freelancer.

Kevin O’Keefe: You don’t have the bars go out and hate you, too. I mean along the way as I’ve watched this, once the bar decides to take somebody down, they’ll take them down with any reason that they can. So if I charged a fee to do that, I was Avvo, and said, okay, we charged a marketing fee for that transaction but we don’t participate in the fee, the bar shuts them down on it. How were you able to do it where you’re taking a commission on that?

Kristin Tyler: Because it’s an attorney to attorney transaction. It’s not attorney to client. That’s a big, big factor of how we haven’t had the same issues as others. And sign. Trying to play a big factor. An unofficial. Exactly. How do you keep doing those work?

Kevin O’Keefe: Does LAWCLERK keep a lawyer relationship, because you’re getting that fee? Because you’re earning a commission, and I’m just curious.

Kristin Tyler: You are the marketplace, and we really are just the facilitator between it.

Kevin O’Keefe: But LAWCLERK gets a percentage of the fee as a corporation, not as a lawyer.

Kristin Tyler: Exactly.

Kevin O’Keefe: It should absolutely be done and it’s a great idea. I mean years ago when I was practicing law, and AOL came about, and I realized that I could find law students on the message boards in AOL, and I would hire them. If you were a third year student, you got $15 an hour, for a second year student you got $13 an hour, so then I terminated our legal research at the firm, because the students had free legal research through their law schools. So if it was a large project, yeah, we handled it, but if it was a motion hearing, or jury instructions or something, students handled that and I kept thinking, this is the coolest thing in the world. And you’ve taken that to a much, much greater level, where people can do all that. How many lawyers do you have who have signed up to be the clerks?

Kristin Tyler: We have over a thousand. More and more every day, and they have the most diverse backgrounds. You know, I love the story of the one guy who is a litigator in a small town in Alabama and he had done a federal clerkship, he went to Birmingham, worked in a big firm, then moved back home to a small town. And he’s got his practice there, but he’s not always busy and so he is just a phenomenal litigator, great writer, people rave about him, say he does great work. How would you ever otherwise connect with some guy in a small town in Alabama? Or this other guy we have in the San Francisco area, he’s actually retired or semi-retired. He’s a 30 year lawyer, bankruptcy litigator, Harvard Law Grad, and once he heard about us, he’s like, this is great because I don’t want to run my practice full time, but I also don’t want to golf every day. And so he comes in, and he picks up one or two projects a month, and I’m sure he doesn’t do it for the money, he just does it because he enjoys the law that much and he wants to keep his mind sharp and help out.

Kevin O’Keefe: How many people are on the other side?

Kristin Tyler: Around 400 now, and that’s a good scale, and that’s something we’re mindful of. We don’t want it to explode on one end and not the other and so we’ve been very mindful as we grow and market to new areas, to try to keep those skills in balance.

Kevin O’Keefe: That’s very cool. You’ve been at it for awhile, because you’re thinking about the idea and you guys have been talking about it for a while. There’s other lawyers here, who are thinking about starting things. If they got to ask you, what would you tell me? What’s your advice, based on what you’ve done so far to tell other lawyers?

Kristin Tyler: I would say, life is short and if you don’t do it, you’re gonna kick yourself, so you might as well go for it. And if you don’t think you alone have the skill set to do it, then find yourself a team – whether it’s one other person, two, three, four, whatever. Find a team where your skill sets compliment each other, and work together well. And I’m a firm believer that every day is a gift and you’ve got to live it to the fullest. So go for it.

Kevin O’Keefe: If I went back to my hometown, where I practiced law in Wisconsin, that ain’t going on. They’re doing their thing as a lawyer, they’re stressed about things, and all that. Why is it these lawyers are doing it though? From everyone I’ve heard from, the last few days, the thing is: just do it. You’ve got to make the decision, because life is too short.

Kristin Tyler: Start small, you know? Find an hour a day. Everybody hopefully can find an hour a day. Get up an hour earlier, block it out on your calendar, just take an hour to work on the idea, work on the business, and move it forward bit by bit. Those little bits of effort will snowball and propel you towards hopefully achieving your goal.

Kevin O’Keefe: Thank you very much.

Speaking with James Pittman, co-founder of Docketwise, fast, intelligent and intuitive immigration software for preparing your immigration forms, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

James Pittman: I’m James Pittman co-founder at Docketwise

Kevin O’Keefe: And what is Docketwise?

James Pittman: Docketwise is a web-based platform for preparing immigration cases. So an attorney creates an account on Docketwise, and then we have a system of online questionnaires for collecting biographical data from the lawyer’s clients, and then seamlessly populating that into government immigration forms, creating tremendous efficiency for an immigration lawyer.

Kevin O’Keefe: So as opposed to a lawyer coming in and getting a legal pad and jotting down all types of stuff, or going on word documents, or filling in blanks form after form. You’re asking the types of questions that will be needed to complete a whole series of documents that could all ultimately decide the track of what forms should even be needed.

James Pittman: Well, we have our bundled questionnaires which have some decision-making features within that, and we had those for family immigration and for US citizenship cases which we call naturalization. And the idea is to dispense with a paper questionnaire. Right. And the idea is to dispense with a paper questionnaire. So you know, the attorney staff can either be entering the information into the database or you could send the client a link, and they can enter it remotely on their side. Data goes into the account, it’s recognized by the account, and then when you create a form that asks for those bits of data, it’s populated into the form.

Kevin O’Keefe: When did this start up?

James Pittman: We’ve been around for about four years.

Kevin O’Keefe: What were you doing before?

James Pittman: I was an immigration lawyer, practicing immigration lawyer, at my own firm. I did that for about 15 years. And with various types of cases I had a lot of family immigration, removal defense, humanitarian cases, business immigration.

Kevin O’Keefe: Did you ever see yourself, when you started being an immigration lawyer, that you’d be starting a legal tech company at some point?

James Pittman: What I was interested in was going to the next level, after helping hundreds of individuals with their own cases, I was looking to take it to the next level, and whether that was going to be in the policy realm, I wasn’t sure. What had happened was a former client of mine came to me after his case was completed and said, “you know, I’m a tech entrepreneur, I have an idea for a company, a new startup around immigration. Do you want to be part of it?” And I thought this is an amazing opportunity. Here it is, this is the answer, right? So now I have a chance to have an impact on the field as a whole, which is just amazing

Kevin O’Keefe: So when you started this thing, how’d you guys get it off the ground? You have a former client come to you, you look at this and go, well, it’s really cool.

James Pittman: There was about a year of solid backroom planning of the logic and doing the development of the aesthetics of the site, the basic coding involved, before it actually went live. And then ultimately it went live, and first it was reaching out to lawyers that I knew, to sort of get them on board, to have them try it out. And we beta tested it with some immigration lawyers that I knew, and then after that the next step was to just start selling and go around to conferences, lawyer conferences, and other events. And then, you know, marketing.

Kevin O’Keefe: Who did that, who went out to the conferences and did the selling?

James Pittman: I did. Sometimes my partner, Jeremy Peskin, who’s our CEO, would come to the conferences as well, but mostly it was me.

Kevin O’Keefe: Was Jeremy the coder side, or the tech side?

James Pittman: He is, yes. He is the head of the development team and, coordinates all of our software developers. We’ve got people in a couple different parts of the world working on it. And he keeps that altogether and plans their priorities.

Kevin O’Keefe: So you’re out there and just said, “okay, now I’ve got to go out to conferences.” How did you take to that?

James Pittman: I liked it. I mean, I like interacting with colleagues, especially immigration law colleagues. I really do. And I used to go to a lot of conferences back when I was practicing, so they were events that I was already familiar with, so I was in a position to really know how to capitalize on that, so I quite liked it.

Kevin O’Keefe: When was the point during this process where you said, “I think we’re going to pull this off, this is really going to work. This could be a business.” Or maybe you knew it from day one?

James Pittman: I kind of had the feeling we were on the right track right from the beginning. And that’s because I knew the technology that was out there for immigration law – most of it had not been updated for quite a long time and some of it was pretty old fashioned, let’s put it that way. The field itself is due for an upgrade. Making the aesthetics more modern, making things more intuitive, easier to use. So I knew there was space for us and then, when my colleagues were interested in trying it out, when we were in Beta, we just had a very easy time acquiring users. So I thought well, we are actually filling a need here. So from the beginning I was optimistic.

Kevin O’Keefe: That’s cool. Was there ever a time when you thought maybe we won’t be able to overcome this hurdle? Or you got thrown a curve ball, and you didn’t expect it?

James Pittman: One of the things that happened was that the government occasionally updates it’s form versions and when they do that then sometimes we have to update our questionnaires. And if it’s minor changes, that’s not a big deal. If it’s major revamping of the information that they’re asking for, then that’s a lot of work for our team. So some of the forms had not been updated for years and then there was a slew, there was this period where they were just issuing new versions every couple of weeks and our entire timetable had to be readjusted to take care of this huge project now that they created for us. So that was one point where I thought, wow, this is really creating. And then, you know, there were, I would say, occasionally you find that you think a feature is going to be really well-received and then people start raising additional concerns, or want additional things included within it, where we have to take it back to the drawing board and then relaunch it. There were one or two instances like that.

Kevin O’Keefe: There’s a lot of lawyers here, that are probably a little bit different than your average practicing lawyer and that tend to be more innovative and looking at new stuff. Some of them are probably with here with ideas of “I’d like to be one of those guys like you, or somebody else.” What do you tell those lawyers about if you got this idea? Should you do something, not do something if they were asking you?

James Pittman: Well, I think first of all, it’s going to be more work than you think. I mean, you might expect it to be a lot, it’s going to be even more. There are going to be complications that you can’t foresee. I mean don’t just to put all your eggs in one basket. I mean, plan carefully and do some market testing, stick around in Beta for a while, do a feature light version in Beta, see how that’s received, and also adequate capitalization is needed.

Kevin O’Keefe: So the market testing can be as simple as you’ve got that Beta and going and showing it to people, right?

James Pittman: I mean, you want to have proof of concept, right? So yes, you want to have a feature light Beta and you want to at least have several dozen users using it regularly and telling you, yes, this is helping, this is fulfilling the need.

Kevin O’Keefe: What do you think about a lawyer keeping their job, and going whole boat into this?

James Pittman: I mean, if you can afford to take that kind of a risk. Certainly the more time that you can devote to it, the faster it’s going to get launched, but that’s just an individual consideration. Certainly have a few months’ rent saved up if you’re going to do that.

Speaking with Chris Smith, founder of Your Firm App, which provides lawyers the opportunity to place a uniquely branded app on the App Store and Google Play, at Clio Cloud Conference 2018.

Kevin O’Keefe: Who am I talking with?

Chris Smith: Chris Smith. I’m an attorney in Oklahoma City, Oklahoma, and a founder of Your Firm App.

Kevin O’Keefe: How long have you practiced law?

Chris Smith: I’ve been practicing for about 14 years now.

Kevin O’Keefe: What type of work do you do?

Chris Smith: Primarily family law, litigation, General Litigation and family law.

Kevin O’Keefe: Always in Oklahoma City?

Chris Smith: Oklahoma City. I’ve also practiced in Dallas, but primarily Oklahoma City.

Kevin O’Keefe: And then how did this idea come along? I mean, it’s not like most people are going to law school ready to start a legal tech company.

Chris Smith: Well, I was one of those guys that kept wanting to see a client-facing application so that we could easily communicate with clients on a native app.

Continue Reading Chris Smith, of Your Firm App, on the Value of Clio and the Growth of Startups in Oklahoma City