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Welcome to the Black Entrepreneur Experience podcast Inside the business buzz and brilliance of black entrepreneurs. Here is your host, Dr. Francis Arlene.
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Before we dive into today's conversation about building a resilient and successful business, let's talk about the foundation. Every high growth venture require a plan for the unexpected. Is your family structure as protected as your business plan? The best contingency plan for your home life is our DIY legacy planning toolkit. Grab this simple roadmap right now at the link in the show notes and let's secure your legacy. Now on to the show. What happens in Vegas goes all over the world on Black Entrepreneur experience, episode number 533. Thank you for joining us as we elevate the black Entrepreneur experience by interviewing CEOs, thought leaders, innovative thinkers and black entrepreneurs across the globe. I'm your host, Dr. Francis Arlaine. How do you take a massive social problem and solve it at scale using AI? That's what we're talking about today. We are joined by Roger Roman, the CEO and cool of Legalese. Roger is a justice tech pioneer backed by Google and TechStart, currently pushing to process 1 million expungements by 2030 to expand legal access and create real economic opportunity. If you're interested in using technology for social impact, opening up legal services for everyone and building generational wealth, you need to hear this conversation. Stay tuned. Welcome, Roger roman.
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Thank you, Dr. Francis. I appreciate you having me on. I appreciate that gracious and lovely introduction. Definitely, you know, you hit on all the points. I'm happy to be here and talk about things that are important to me and that are important to your audience and talk about what we're building and how we can, how we can help a lot of people.
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Well, thank you for that. I've given our audience, Roger, such a brief bio. Why don't you fill in the gaps, share with our audience what you'd like them to know about you and your business.
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Gotcha. So I am a tech entrepreneur, a serial tech entrepreneur. I've, I've started several tech companies over the past decade or so. I failed at a lot of them. Most of them actually have failed. And, and you know, with each lesson, with each failure, I've, I've taken something away and been able to build on it in my next venture. And here we are now. I'm building a legal tech startup, Legalese, with my co founder Lawrence Blackmon, and I feel like I finally, you know, hit the point where I'm building something that's both needed, necessary and, and scalable. Right. So it's, it's, it's that, that trife of success that you really need to build a business and then especially a tech business and get it off the ground. Right. If it's, is it solving a problem one, I think we got that we're solving a problem, we're helping people, we're relieving the pain point. And then on top of that, is this something that can scale and impact people en masse? And expungements are something that a lot of people don't know about. But a third of the population, over 70 million people, have a criminal record or some, some blemish on their record. Right. And this is something that we're attacking. That's, that's a right for people to, to actually go about and, and get done. And it's not a, it's not a loophole or, you know, some, some work around the system. It's actually something that's written into law that a lot of people don't take advantage of. So happy to be working on it and building something that people can actually use to, to improve their lives.
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Tell us your backstory. Why expungement and what's personal about this for you, Roger?
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Gotcha. So I am, I was born and raised on the west side of Chicago, so I have to make that distinction. I wasn't just born in Chicago, I was raised on the west side. And if you're from Chicago, you understand why I'm making that distinction. Born and raised there, had a very hard working family, Education was paramount. And I'm giving you this backstory because it kind of leads to where the, the genesis of legal leagues. Right. All my life pretty much, you know, from the time I can remember being able to talk, I was told that I was going to be a lawyer. It wasn't my choice. It wasn't something that I decided. I just knew from as long as I could remember that my parents and uncles, you know, Roger's going to be a lawyer. Right. You know, I was pretty good in school and when I graduated high school, I was getting ready to graduate. You know, I wanted to go to an hbcu. That was a decision I had made early on in my high school careers. I went to a predominantly white high school and, you know, face some challenges there. It was good. I mean, I had a good experience overall and, you know, I did well. But just internally, right, I had some, some challenges that I faced and I was determined to go to hbcu. So I want to say my junior year might have been my sophomore year. But I opened up the College News and World Report college rankings and I said, the first HBCU here, I see that in these rankings. That's the one I'm going to go to. When Howard was there, right? I think it was number 80 at the time. It's moved up since then, and it was actually the only HBCU on that top 100 list. So I said, you know, I'm going to Howard. So fast forward, I go there. I joined the mock trial team because I'm still on this track to be an attorney. And I meet my co founder, Lawrence. He was a. He was a couple years younger than me. He came in and we met on the mock trial team and just kind of hit it off, became boys and you know, real cool. Never really. We did a lot of enterprising things like we, you know, we worked on campaigns together and things like that. But it wasn't. The plan, wasn't, hey, we're going to start a business some, somewhere down the line. We're just boys. And it's kind of like my little guy, right? You know, I looked after him. And I want to say, some years later, around graduation, around the time it was time to graduate for me, I decided that I didn't want to pursue law in a legal career. And I really didn't know what I was going to do. I was working in real estate development. I thought that might be a path for me. But it was right around the time of the Great Recession where, you know, in 2008, you know, things went really bad, kind of similar to some of the stuff we're experiencing now. Not as extreme, but. So I, I had another friend who had a video game idea. He was going to go to California and try to get this off the ground. And he asked me to join his team and I did. And oddly enough, Lawrence, my co founder for Legalese, was, was a part of that group as well. So we went to California with this video game startup and we failed miserably. Right? We only had a little bit of money, didn't know what we were doing. We're in way over our heads. And after that venture failed, everyone kind of dispersed and I stayed in California. So, you know, this is where I am. I like this. I like the tech industry. I think this is where I belong. And I worked at a lot of different startups, just whatever job I can get, marketing, go to market stuff, taking out the trash, whatever I could do, right? I just wanted to learn from, from, from these founders and from These people who are building these tech enabled companies. And Lawrence actually went back to law school. So he went home, went to law school and matriculated through law school. And he would always call me or send me texts like, hey bro, I got this idea, you know, you should check this out. I'm like, oh, stick to your day job. You don't want part of this monster, right? The roller coaster of building a tech company. And one thing he kept coming back to was expungements. I mean, he would just say, you know, this is a, this is low hanging fruit. This is something that can really be taken advantage of. I'm charging people 1500, $2000 and pretty much all I'm doing is filling out a form, right? There has to be a scale scalable solution to solve this problem at scale. And he was persistent and eventually he convinced me to help him work on it. And we built an mvp and I sent it to him, I put it up on his website and he started to use it in his practice and using in some pro bono work. And about two months after that, I thought it was done. I was working on some other stuff and I was like, okay, I helped my boy out. It's cool. I get a text message like, yo, bro, you know, this is something that's amazing. People are, are, you know, flocking to it. We got to get on a call right now because there's something here and, and you know, fast forward to today and we're building this company and that's pretty much how it started. I left out some things, right. Like Lawrence had, of course, when we were in undergrad at Howard, Lawrence did have an interaction with law enforcement where he was arrested. And that was dismissed. It was thrown out. But he was afraid that it was going to affect his law school chances. Right. So his dad, who's an attorney, told him about expungements and that was kind of his introduction to it. So he needed an expungement to get into law school. And when he got out practicing in Mississippi, he was actually servicing a lot of people, helping them actually get expungement. So that's the genesis of it. It wasn't like this Eureka idea. It was something. It happened over a course of time. And it was thanks to his persistence we decided to jump in and build something around it.
C
Thank you for sharing that. And Roger, you said something. Talk about failure. Your words. A lot of people don't like to use that word, failure. They like to use it opportunity. Let's talk about failing forward. What lesson did you learn. Or it's probably multiple lessons. But what is one of the most valuable lessons you've learned in that as a serial entrepreneur? And failing forward.
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Yeah, that you hit it. Failing forward is, I think, the correct term, because if you're not taking something from it. Right. It's really a loss. I think, and I've spoken about this before, I think the most important thing that I learned was that there's a fine. There's a point between persistence and resiliency and knowing when to pivot. And I think it's hard. You know, there's no magic bullet for that. There's nothing that. That can prepare you to. To know when the right time is to be. To. To be resilient and keep building and stay focused and stay and keep pushing forward and know, okay, this is not going to work, you know, and I've. I've exhausted all of the options, and there's no. No other way I can go. And, you know, if you can figure out that and if you can be able to read that, I think you can have some success as a entrepreneur, because resiliency is probably the strongest muscle you need. Right. Every day it's a roller coaster. You're going to face some hardships. You might have the best news in the morning. You might land the biggest client or get the biggest partnership or deal at 10am in the morning, and then you get the worst news at 4:00pm and this is every day. So being able to be resilient and resist those ups and downs and ride the roller coaster, I think is probably the strongest skill you need as an entrepreneur. But there's also a time when you have to say, okay, well, there's nowhere, you know, you know, I've exhausted everything. And I. I think back to. I'm a huge sports fan, and I think back to, you know, quite. I don't know if it was Michael Jordan or Colby, but one of them said, you know, they're not nervous about their skill set when they step on the court because they know that they put their all into it. Anything. The game is going to go the way the game goes. But if you. If you put everything you can into preparing for it, you know, it's not. It's not a concern. And it's. It's similar with business, right. If you've done everything that you. And make this business successful, if you've exhausted all of the channels that you've put everything into it and it's still not moving, then that might be the time where you can say, you know, okay, let's pivot, let's do something else, let's focus on something else. Let's go back to the drawing board. Maybe we need to rework this whole business model. Just that fine line between resiliency and knowing when to hang it up. I think is, is one of the biggest lessons learned.
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Want you to have a monologue and I want you to name this person, living or not, and they've inspired you so much. Who is that person and what are you saying to that said, wow, that's.
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That'S a good one. I mean, so I can go the, the easy route. Like my father passed when I was nine, you know, so I would love to have a conversation with him. He was very influential. And you know, to this day, you know, as a 41 year old man, I still think about some of the things I learned from him. I think that might be the easy way though, because people don't know my dad. I think one of the first people who really have inspired me and has remained a constant inspiration throughout my life from my early teen years is probably Malcolm X. You know, and I think Malcolm X really is the embodiment of what we're building with legalese in terms of a person who had a rough start, so to speak, and made a lot of mistakes early on in his life and was able to rebound and change that in the second half of his life. Right. So just having a second chance and being able to move on from your mistakes is really the ethos behind what we've built. Illegalese and helping people. If I had to have a conversation with him right now, the number one thing I would do is thank him, you know, for putting his life on the line and dealing with all the things that he dealt with and thank him for being an inspiration. He showed, he's shown. He's a perfect example that a person can really have a rough start and be able to bounce back and make something of their lives and take advantage of a second chance. I know that wasn't a monologue, Dr. Francis. I'm sorry.
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No, that was good. Let me ask you this question. One of the things I enjoy is AI. Talk about AI and your take on it and how are you using it in your business.
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Absolutely. So this is. So of course our company, legally, it's built around AI. Right. You know, we're, we're using AI to kind of solve, solve this problem and help a lot of people out. I think we're at a inflection point in society right now with artificial intelligence. I think it can definitely be used to bring a lot of harm to people. I think it can be used to make people's lives harder and enrich a few. But on the flip side of that, I think, you know, in the right hands and with the right guidance, it can be used to actually help a lot of people. And that's the kind of the stance I'm taking on it. And I think it's lessening day by day. There's a lot of weariness around it. People are afraid and skeptical about it. I think at this point the cat is out of the bag and it's going to be a part of our daily lives for, you know, from here on. And most people should just take advantage of it. You know, it's akin to the calculator, right. When I was a kid, you know, it was. We were forbidden to use calculators in class and, you know, teacher said, you're not going to have a calculator in your pocket, you know, when you're an adult walking around. And here we are, you know, years later, and we all have a cell phone, right. With a calculator on it. So, you know, I think it's one of those. Those things similar to the Internet. You know, when I was coming into high school and doing research for papers, a lot of teachers were saying, go look at the. Go to the library and look in the encyclopedia and use the Dewey Decimal System. Don't rely on the Internet because you can't rely on the information. It could be misinformation. And we're seeing the same warnings about AI right now. And I think just as we get used to it more as a people, as a society, it'll become more of a daily part of our lives. And as the technology gets better, just frankly, a year ago, you know, we first started. A year and a half ago, when we first started building Legalese, the technology wasn't quite up to par for what we envisioned. But here we are a year and a half later and it's exceeded our expectations in terms of capability. So I'm a big fan and a big proponent of artificial intelligence, but I also, you know, caution people to use it correctly. Right. You know, it's not just. Just as you wouldn't in the year 2000, you wouldn't go to Google or Google wasn't around, but you wouldn't go to Yahoo and, or any of these other search engines and search a topic and then just copy and paste it and put it into a paper. I don't think you can do the same thing with AI you got to use it as a tool and not not as a, as a crutch, so to speak. It's an additional tool that you can use to, to help you in your life. And I think it can help in a lot of different ways.
C
Who is your ideal client for legalese, so for expungements.
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In our first flagship product, Expungement AI it's a person who is looking to be socially mobile, who's looking to advance their life in some form or some respect. And they have this blemish that Maybe it was 10 years ago they made a mistake or they did something they were arrested for and maybe they weren't charged, maybe they weren't convicted. But most people don't know any interaction with police officer. If you're put into the system, that's going to come up on your record, right? And they're looking to either a get a promotion at work, they're looking to qualify for rent to own loan, maybe they're looking to volunteer at their children's school or coach a little league baseball team or there's the range of people and how it affects these records, affect people is wide. But it's the person who is looking to remove this blemish from their record. And we've had people actually who just didn't want to have this on their record. There wasn't any acute pain, there wasn't any job promotion or any career advancement that they wanted. They just didn't want to have this ugly mark on their record. But that's typically the ideal customer, someone who has an acute pain and they want to remove this thing because they want to move forward in their lives. And up until this point they haven't either a known how to do it, had the funds to pay an attorney or just really had any motivation to do it because they thought it was too complex and too hard of a process.
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And let's talk about funding and access to capital. How did you fund legalese?
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Yeah, so that's a good question because I think to black entrepreneurs in particular, that's probably the most important or most difficult hurdle to get over. Right. You need funding. That's just. There's no way around it. And unfortunately for us, you know, there's a lack of it across the board. Early on we bootstrapped. Right. So it was a side project. When we first started, my co founder was still practicing law. He's also a state representative in Mississippi. I was still working at another startup and at a consulting firm at the Same time. And you know, this was something that we were doing on the side, so we were coming out of pocket. You know, we were putting skin in the game. And I joke because my co founder spent a lot, a lot more money than I did early on because this was kind of his baby. But we put us a substantial amount of money into just building and discovering and you know, you could even say like a lot of that money we spent, I won't say it was wasted because we learned from it, but it was, it was towards things that we don't even use today, right? We're doing things that turned out not to be something that we needed down the line, but early on, that's how we started. And then in the fall of 2020, 2024 last year, we were accepted into Techstar. So not sure if your audience is familiar in the tech world. They have these accelerators which are these, these organizations that, you know, they'll invest money in your company and you'll go through a boot camp of sorts, right? You'll go through a three month boot camp where you work on investor readiness, right? How to pitch your company, how to raise money. You know, what metrics do you, should you be tracking? You'll go into, go to market, you know, when you launch, how do you launch your company, how do you go about doing that, how do you get your story right? You know, all these things that you need as a, as a tech entrepreneur to get your company off the ground. And they'll also invest, right? They'll give you a solid investment to start off. Techstars is one of the premier accelerators. It's right up there with Y Combinator and a few others. We were accepted there in New York and we got a little bit of money. At the time, I think the investment was 120,000. They've upped that since then. It's 220 now. And that allowed us to hire or bring on board our third co founder, Rasheed, who also went to Howard with us and come on as our cto, right? So that was a real breakthrough for us. He was able to come in and really build out our back end system and our automation and things like that. And once we did that, we were, once we finished techstars, after three months, we actually hit the ground and started fundraising, built an investor pipeline and we started pitching, right. And the funny thing about tech is that everyone wants a warm intro, right? And luckily for me, I've been around for a while now, so I've met a lot of people. And I was able to get some of those warm intros early on. But it's really just about the hustle of trying to meet people and convince them to sit down and talk to you. And then once you do that, that's just the first part. You got to actually pitch them on your company and convince them that this is something that's going to 10x for them, right? Investors, tech investors in particular, they're looking for home runs, they're not looking for lifestyle businesses. They're not looking for something that's just going to make some money and be able to support a few people and create some jobs. They want businesses that are businesses that are going to 10x, right? Is this business going to be worth 10 times more than what it is today, you know, come five years from now? So being able to convince them of that. There's an art to it. You know, it's a little bit of science, but it's mostly art in terms of pitching. And we were able to do that. We went out and today we have. We've raised about 1.1 million. We set out to raise 1.3. Our round is still open. We'll probably close it in the next few weeks. We are in due diligence with a few people. And yeah, that's pretty much the, you know, that, that's the story. It took us about, I want to say, about three to four months, which is actually pretty fast. In my previous experience, I've, I've, I've been fundraising for a year. I've been fundraising for six months, and I've struggled to raise, you know, so I understand that it's, it's not always easy, but when you come with the right solution and you do your, your homework on your investors. Right. I think one of the mistakes I made early on with some of those early startups was that anybody who had investor on their name, we would go and try to pitch them, right? Anybody. And, you know, you waste a lot of time that way. You get a lot of rejection. You're going to get that regardless, but you should try to save yourself some of it and find the right people. So one of the things I think with this company in particular was the homework we did and the preparation we did before we actually went out to fundraise, we built our investor pipeline, which was a spreadsheet over 100 investors. And then we did research on each one to see if they were actually interested in something that we were building or if they had invested in a competitor. Right. Or, you know, where if they had money, right? There's a lot of investors out here who will take your meeting, and they don't necessarily have the funds to invest in you. So I think that's the biggest part. And that was one of the things that I've learned over time from, from those many failures is that, you know, you gotta do your homework on people. It's a marriage, right? It's a marriage that's Gonna last for five to 10 years at the least. And if it's successful and you wanna have the right people on your cap table.
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Oh, so that's you hitting. You hitting with these. Dr. Francis, I think early on my biggest mistake was trying to do everything myself. I'm a self starter. I'm a go getter, you know, and I take pride in that. I take pride in being a person to get up and do it and figuring it out, right? That's one of the things, it's one of the many lessons my mother taught me. You run into a problem, you run into an issue, and you just got to figure it out. You know, you can cry about it and all that, and that'll make you feel okay in a moment, but at the end of the day, you got to figure it out. And that's been something that's driven me. And the byproduct of that is that, you know, if I don't necessarily have it or if I don't know anyone who does this thing or has this skill, you know, I try to figure it out and do it myself. And I think that drove a lot of stress. One and failure, right? Because I'm not a graphic designer by trade, right? I'm not. I was never trained to be a graphic designer, but I know how to do graphic design. And, you know, so now I'm doing graphic design when I should be focused on my financial model and I should be focused on hiring and I should be, you know, and I'm juggling all these things I'm trying to do. Everything myself early on. And that was something that I had to really just let go of. And it's still, it's a work in progress. You know, I still, I wear a lot of hats with my startup, but I've learned to delegate and entrust people and bring in the professionals. Right. You know, they can do a lot better job than you and they probably can do it a lot quicker. You know, one of the barriers to that, I think for sure, and I wouldn't be, I would be dishonest if I didn't speak to it, is funding. Right. A lot of that was driven out of necessity. I didn't have the funds to pay a graphic designer. I didn't have the fund. But I will say doing those things early on and knowing the basics of it have made me a better person to hire. You know, the people I need and understand exactly what I want may not be taken advantage of, you know, by people out here who prey on the week. Right. So, you know, I. That was one of the biggest lessons. You can't do it all by yourself. You're going to need a team. You're going to need to build up a team, you're going to need to empower people and you're going to have to trust people. So make sure the people you have on your team are good, are good folks and they're good at their job, and then you can entrust them to do it.
C
And Roger, I like what you said. You have to. And one of my mantras is you have to delegate to elevate. Someone's listening to this conversation and I appreciate your authenticity when you talk about that funding piece. And it's huge. And for a lot of black entrepreneurs, having access to that capital, doing the friends and family round is not necessarily what we can do. So I want you to talk about creative financing, creative funding. And I agree, and I have to say that has been one of my opportunities, is doing it alone because you don't have that capital and you're trying to find resources to get it done. And sometimes cheaper is not always the best. And sometimes even individuals that say that they can do it and you're paying a lot of money is not the best. So speak to that.
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Yeah, I think again, there's no, there's no cut and dry here. It's never black and white. So, you know, the same way I say I had to learn how to delegate, I think the advantage was that I was willing to learn some of those things early on. And even though it might not have been the best graphic design, you know, it might not have been the best code. I've coded. I've done everything. Those experience helped me so that I can find people who are competent. And it's a struggle, you know, even now with the funding and being able to hire people, you know, there's a lot of people who might not be the best fit for what you're doing, right? Or they might not have the skill level that they profess to have and just kind of having that awareness and understanding, okay, this, this is where this person is, despite what they might say. And being able to judge at work has been instrumental. I think one of the, again, it's a barrier. You can't get, get around it in terms of the funding and stuff early on. So I advise people, I say, look, if you really want to be an entrepreneur, if this is what you want to do, and you know, you're working at 9 to 5 or you're, you know, you, you however you're making money right now, you're going to have to sacrifice some time, right? And if you're working and you get off work at 5, you get home by 6 or whatever, maybe 6 to 9 is the hour are the hours that you're working on your business because it's going to be a while before you're able to live off of it, right? It's going to be a while before you're able to use it to support your lifestyle. So don't just quit your job and jump into this space. Trust me, it's not, it's not going to be pretty, right? Kind of take, take those steps and build yourself up until the point where you can actually start to use it to support yourself. But until it, until it makes money, until it's really generating revenue for you, it's more of a hobby than it is, you know, a business, right? And your goal is to get it to a business. And you need to live, you need to keep the lights on, you got to eat, you got to take care of the family and everything else. So focus on making sure that you have some stability and you have some foundation and then you can start to build on that slowly but surely. And you know, if things work out, maybe you can leave that job and focus on this full time, you know, and if they don't, you still have that safety net, you know, of a nine to five or whatever, you know, you're doing to keep the lights on and you're not kind of falling flat on your face as I've done in the Past. Learn from me. Learn from me. Keep that day job.
C
Please don't do the day. Quit yet.
A
Nah, not yet. Not until you can pay those bills, man. And because again, it's hard. Like, you know, for instance, with legalese, we haven't taken a salary, right? My co founder and I, we haven't taken a salary. You know, people hear like, oh, you raised a million dollars and you've done this and you've done that. But, you know, we haven't hit the point yet where we're like crazy successful and everything is taken care of. You're like, yeah, it's one thing to see checks come in for 200,000, $300,000 and it's good and it motivates you, right? But it's not. We haven't been in a position where we've made it so far, right? And if you don't have a stable, stable foundation, it's hard to even get to this point where you've raised a little bit of money and now you can start to build the business and grow the revenue and put yourself in a position where you could potentially just, you know, make more money and generate work more revenue or go raise another round, right? You, you haven't put yourself in that position yet. So you got to make sure that foundation is steady.
C
And what do you need right now that you don't have to move the needle forward?
A
That's interesting. I think we're in a really good place right now. I need the due diligence on these last few investors to speed up a little bit. And this is for your audience. When you go out for an investment from institutional investor angels are really easier because it's a high net worth individual and they pretty much make the final decision. But if you go to a venture capitalist or one of these institutional investors, not only do you have these introduction meetings which might last a month, maybe six weeks, because you have the first meeting, then you have a second meeting where they dive deeper into your business and your business model and the product, and they basically are checking you out to make sure that you're legit. And then they'll give you a yes. But it's a conditional yes, right? Maybe you'll have another meeting between that with the partners, but you'll get a conditional yes. And the conditional yes is based on due diligence. And due diligence, we've seen it take as long as six weeks. We've seen it take as long as two and a half months. It's where the VC or the institutional Investor, they go quiet. You give them all of your formation documents, you let them into your data room, which has pretty much everything about your company in it. It's a folder basically online. And they do research on your market, they do research on the founders, they do a bunch of research on the back end. Then they'll come back and say, okay, you guys are good, or actually, we're going to pass on, on that. So in due diligence right now, with a few investors to go ahead and close this round so we can move forward, I think if I had anything that would be, you know, if we could get that, and I think I'm pretty confident that we'll be fine. It's just the, the weight of doing that while at the same time you're still building the business, you're still getting traction, you're still, you know, working and developing and, you know, tweaking your product to make it better based on customer feedback, all while waiting on, you know, this final yes from an investor or two.
C
What advice would you give to your younger self? The version of you just starting out?
A
Believe in yourself, man. Again, I keep going back to this. When you're on this journey, I don't care how confident you are. I consider myself a very confident person. I have maximum belief in myself and my abilities. There are going to be dark times where you question, you know, are you the person to do this? Are you. Is this for you? Right. Should you just go and fill out some applications? And in those dark moments, it really takes you, that belief that, that almost delusional, you know, it's got to be a little bit of delusion there to push you through. So I would just go remind myself, you know, before I start, like, hey, you got this. You know, you're prepared for this. This is something that you chose to do. Fight through it. You're going to run into, you know, brick walls. You got to fight through them. You're going to run into roadblocks. You got to fight through them and just keep going and everything will work itself out.
C
I think we had a little bit of feedback.
A
Did you hear that on your. Yeah. My apologies. Just. I don't know what's going on out there.
C
Okay, let's talk about mental wellness and entrepreneurial ship.
A
Yes. So, I mean, that's a big part of it because, you know, stress is. Stress is probably the number one recipe that you're gonna. You gotta experience as entrepreneur. And it's, it's not all bad. I mean, you know, we talk about good problems now. My co founder and I, we have a lot of good problems. They're still stressful, they're still problems, but they're good problems to solve. I think in terms of mental wellness and that stress, stress is the biggest thing, you know, and whatever you can do when everybody's different to relieve that stress is good for you. Some people meditate, some people read books, some people go for a walk, some people take naps, right? You know, I've had some friends who say, you know, I just need a good 30 minute, 40 minute nap and I'm refreshed. So, you know, I think it's number one, you're not going to survive if you're, if your mental health is not taken care of. And to think that you're going to be an entrepreneur and not deal with the daily assault on your mental well being is pretty naive, right? Something that you're going to deal with, you have to find those moments, those moments of peace, those moments where you can kind of just zoom out. You know, I have three children, I have a wife and three children. You know, I, I make time for them. Like I, I think the term work life balance is, is not necessarily the, the correct term because it, there's always going to be an imbalance, right? But, but when I make time for my family and I try to be fully present for them, right? So, you know, weekends, you know, whether it's sports or school events or whatever, or just going out to dinner or having dinner at home, whatever, I use that time to really just kind of shut off everything. Work for the most part. You know what I mean? It's always there a little bit. But I try to shut it off as much as I can and focus on that. And that gives me a little bit of relief, right? And then I'm able to walk back into work and I'm, I'm actually missing it, right? I'm not stressed out, I'm not beat down. I'm like, okay, well, you know, I missed what I was doing. Let me get back to it and be a little more pumped about it. So I think each person is different. You have to figure out what works for you. I've tried to meditate. Meditation is actually good. I do it every once in a while. I don't do it as much as I should. I think the problem in the past is that I was too tired and I would fall asleep. So it wouldn't be meditation, it would be more of a nap, right? So, you know, the peace and the quiet, I would just wake up 20 minutes later. But, but yeah, I think, you know, just your mental well being is very important and if you're not taking care of it, it's going to come back to bite you in the end. The same with every other part of your health, right? If you're not taking care of your diet or your sleep or all those things, eventually those things are going to compound and start to affect you. And you want it to affect you positively, not negatively.
C
Let's talk about legacy. When it's all said and done, Roger, how do you want to be remembered?
A
I would like to be remembered as a person who was an achiever one. I mean, I guess that's the selfish part of it. Right. Achievement is something that drives me. I like to do things and be accomplished. Right. That's, that's something that's been, has driven me since I was a kid. But also, you know, every startup I've built and every company I've built outside of, I mean, pretty much every company I've built has had an underlying ethos of helping people and improving people's lives. And I think that is, is really the ultimate legacy that I want to leave behind. Right. Did I do something that actually helps some people out? You know, whatever that is, you know, whatever however that can be. Was I able to do something, build something, in my case, build something that actually helped folks and can those people point to me helping them? Right. Like this, this action that I took on this platform that was built by Roger Roman actually helped me. Right. And even though they might not acknowledge it, just knowing that, you know, I was able to help some folks improve their lives and be socially mobile and, and, you know, have a better future or a brighter future. I think that's the biggest legacy. We all want to help, you know, we all want to be good people. And you know, there's only so much we can do as humans. Right? But there is much. Right. There's a lot that we can do. And if we focus on that, you know, I think that that can be a solid legacy to leave behind. And I help folks and then, you know, of course I'm a father. So, you know, my children, I want to just make sure that they, you know, when I'm long gone and they have children of their own or whatever, and they always remember me as a person who empowered them as well. So empowerment, I think is the word that can sum it up. A nice little boat. You know, have I, have I empowered people throughout my life? Yeah, that's, that's, that's the Legacy, empowerment.
C
And when you talk about and only share what you can, I'm sure you have many success stories around the app. Legalese, can you share a story how you've made impact daily in people's life?
A
Yeah, absolutely. So, yeah, I can't, of course, it's people's legal history. So, you know, I'm not going to share names or anything, but I'll give you two, two stories. One was one of our first customers. It was a young lady in Mississippi and she was a cna, a nurse's assistant, right? And she had dreams or hopes of being an rn, right, becoming a registered nurse. And she wanted to go through that, but she had stalled going through that process. She didn't, she never pursued it because she had a domestic violence record, right? She had a domestic violence incident on her record and it was a misdemeanor. And it turns out, I don't know the exact day, But I'll say 10 years before, she got into an argument, a public argument with her boyfriend at the time. There might have been some, some alcohol involved and they got into a fight and they were both arrested, right, because they were in this public space. And I think it got, you know, some pushing and shoving and stuff like that. Fast forward. She's moved on. They actually are married now with, with the family, those same two people, right, with this, this DV on it. But she, she had a mental block. She, she never wanted to pursue anything because she had this ugly, ugly thing on her record. You know, we, we, we hear domestic violence and we have these images of, you know, this, this horrendous abuse that people go through. And of course, you know, we don't want anybody to, to go through that. And people who purport that are people who are, who hurt other folks, right? And especially people in their family, those aren't people we want to help and support. So she's always had this in the back of her mind that I can't move forward in this space because I don't want that to want even come up. I don't want anyone looking into my background. And two, once they find out, I won't be able to move forward. And we were able to help her get an expungement. We were able to get it off her record so she could go ahead and pursue that and make more money and have a better life and have a more fulfilling career. That was one of our first customers recently. I had a young man who reached out to us and I told him his story was crazy, you know, He. He had a pretty rough young adult life, and he. He made a lot of mistakes about 20 years ago, and he was arrested for some things. And here we are, you know, all this time later. He's an upstanding person. He has a business, he has a family. He stayed out of trouble the entire time. He goes to sign up to be a coach on his son's football team, and you have to have a background check, of course, right? And it comes back and he's rejected, he's denied he can't be the coach of his son's team, which is something he's volunteered to do because of this stuff on his record in the past. Right. And he's like, you know, it happened 20 years ago, but, you know, there's no workaround, especially when it comes to dealing with children. You know, if you're flagged, you're flagged. Right. And he wanted to get that stuff removed desperately because, you know, this was something that was important to him to be able to. To spend that time not only with his child, but, you know, with other children in his community. So those are two. Two stories. And I mean, they. They are real stories, right? Those are real people who are faced with real things. But like I said, you know, it can be even more extreme than that, you know, in terms of how these records are holding people back and how.
C
Are people finding you?
A
So right now we are only live in Mississippi. I'll go back and give you a little bit of the past couple of months and what has happened after we launched. So we launched in the last month of July, we launched in the last week of July, and we thought, you know, we'll get a few hundred people in Mississippi to sign up. That's where my co founder is from every state. So the reason we launched in Mississippi was because every state, the law is different, slightly different. So we're going to roll out into each state individually. We thought we'd get a few hundred people, we got a few stories written up about us online, and to our surprise, we had over 3,000 people sign up from all over the country. You know, they found us reading about us or, you know, word of mouth and things like that. It really was inspiring, you know, in terms of the demand that was there and the amount of people who really wanted us or wanted to use the platform. I mean, we had people from as far as California, Iowa, even out of the country, people in Canada saying, you know, how can I get this in my state? And it caused us to go back to the drawing board. In terms of our rollout, we had a very conservative plan to roll out state by state and we decided that we had to speed that up a little bit and accelerate it. So now we're in the process of getting ready to launch pilots in California, Texas, Georgia, Illinois and Maryland. Right. In addition to Mississippi, we're going to roll out into those states and then we're just going to follow on. Every month we're going to roll out into a few more states. Right now most people are just finding us on social media. You know, our word of mouth in Mississippi we did run a few ads, we ran a few TV ads and stuff like that. But mostly people have, have just kind of, you know, found us in the ether, right. They found us in space. And you know, once we go into our next round of funding or, you know, we start to really accelerate our revenue, we can drive with more marketing, right. And we can, we can put more ads out and things like that. But right now it's really been more of a grassroots effort.
C
Roger, if you conducted this interview, what is the one question you would have asked yourself? I'd like you to ask the question and answer it.
A
That is a heavy one. These are great questions, Doctor, thank you. What does the future hold for Legalese? What does the future hold for Legalese, Roger? I'll say, of course, starting with expungements, we want to expand nationwide and be effective in every state, be live in every state. And that's our plan over the next year and a half. We plan to be there by Q4 of 2026. And you know, our ultimate goal is to help more than 1 million people have an expungement by 2030. That's our plan for expungement, AI which is our flagship product. But ultimately we're building a company illegally that is really focused on helping people solve these non complex legal matters without an attorney. So long. For so long the legal system in the justice system has been used against people and people haven't been able to navigate because they don't have the funds or they don't have the know how. We want to build tools that helps people empower themselves. Think of it similar to a turbotax, right? There was a time where you had to go to an accountant or CPA to do your taxes and you know, they would charge you and it was a business. But now, excuse me, you can pay TurboTax, you can go online and you can have a guide that can guide you through your tax returns and things like that. You can feel confident doing it. And that's similar to what we're building in the justice tech space. We want to build something that helps people be empowered to solve these matters and to do these things on their own and not be held by lack of funding or lack of access to an attorney or anything like that. You can go out and do it yourself and, and learn in the process.
C
We've come to the part of our interview, it's called the rapid Fire questions. I'm going to ask you a series of questions and I'd like you to give me very quick answers. And if it's something you desire not to answer, feel free to say pass. Are you ready for the rapid fire questions?
A
Let's do it. Let's do it.
C
What's the first thing you do every morning?
A
Drink a cup of water.
C
What book changed your life?
A
The Autobiography of Malcolm X.
C
What's your favorite failure? The one that taught you the most?
A
Oh, my first startup. My first video game startup.
C
Coffee or tea while building an empire.
A
Oh, coffee. I'm an addict.
C
What's one app or tool you can't live without?
A
It used to be. Notes I would say chat GPT. At this point, I'm just being honest.
C
If you had to pitch your business in one sentence, what would it be?
A
We make it easier to process. Thanks, SpongeBob.
C
An entrepreneur you'd love to have dinner with, dead or alive.
A
Oh, that's a tough one. John H. Johnson.
C
Roger Roman, thank you so much for joining us on Black Entrepreneur Experience podcast. Before we let you go, share with our audience the best way for them to connect with you and do business with Legalese. And feel free to leave all your social media the way they can reach you on social media.
A
Absolutely. So the best way to find us at legalese is legalease.com. that's legal. L e G-A L E-A-S-E.com. you can find all of our socials there. Unfortunately, we don't have one handle for all of our socials, so I'll spare you all of you know, get Legalese on Instagram and this there and just go to our website. You can get to every social social channel we have. And I'm, I'm pretty active on social as well. You can find me mostly on LinkedIn. You know, I do a little bit of Instagra and stuff like that. Not much, but if you really want to connect with me, I think LinkedIn is probably the best place. And it's just my name, Roger Roman. You'll see me as the founder of Legalese if you're looking me up, that's the best place to get in touch with me and send me a message there. And I might not get back to you right away, but I'll get back to you eventually. May take a week or so, but. But yeah, that's the best place to find me.
C
Thank you, Roger. That's a wrap. Thanks again to our incredible guests for sharing their insight on building a resilient business. And remember what we discussed. Resilience. Start at home. If you're ready to protect the legacy you're building, not just the income, make sure to check out the DIY Legacy Planning Toolkit. You can find the direct link in the show notes. Go get your peace of mind now.
B
Thank you for listening and subscribing to Black Entrepreneur Experience. We would love for you to leave a review and rating on itunes and share with your friends. For show notes and more episodes, go to www.beepodcast.com. join us next Wednesday. And remember, green is the new Black, so keep your bank accounts and your business in the black.
Title: AI for Social Justice: Roger Roman's Mission for 1 Million Expungements
Host: Dr. Frances Richards, Chief Encouraging Officer
Guest: Roger Roman, CEO & Co-founder of Legalese
Date: January 21, 2026
This episode highlights tech entrepreneur Roger Roman’s journey and mission to use AI for radical social impact, focusing especially on expungement of criminal records. Roger, CEO and co-founder of Legalese, shares his personal backstory, the vision behind Legalese, and his goal to facilitate 1 million expungements by 2030. The conversation covers entrepreneurship lessons, funding challenges, the intersection of AI and justice, and actionable advice for Black founders.
"Expungements are something that a lot of people don't know about. But a third of the population, over 70 million people, have a criminal record or some, some blemish. [...] And it's not a loophole or workaround—it's written into law."
—Roger Roman [03:09]
"There's a point between persistence and resiliency and knowing when to pivot... If you can figure out that, you can have success as an entrepreneur. Resiliency is probably the strongest muscle you need."
—Roger Roman [09:31]
Delegation as a Key Skill: Early tendency to try to do everything himself led to stress and limited growth.
"You can't do it all by yourself. You're going to need a team, you're going to need to empower people and trust people."
—Roger Roman [24:10]
Funding Journey:
"In my previous experience, I've struggled to raise... When you come with the right solution and do your homework on investors... you save yourself rejection."
—Roger Roman [19:45]
Advice for Aspiring Founders:
"Until it's generating revenue, it's more of a hobby than a business... focus on making sure you have some stability before you leap."
—Roger Roman [27:38]
"We're using AI to kind of solve this problem and help a lot of people out. Used correctly, I think it can be incredibly empowering—it's like the calculator for the legal system."
—Roger Roman [13:27]
Ideal User:
"It's the person who is looking to remove this blemish... maybe it was 10 years ago, maybe they weren't convicted—most people don't know any interaction with law enforcement can come up on your record."
—Roger Roman [16:03]
Rollout & Demand:
"We thought we’d get a few hundred people... to our surprise, we had over 3,000 sign up from all over the country."
—Roger Roman [40:43]
"Those are real people, faced with real things, and for some it’s even more extreme—these records hold back whole lives."
—Roger Roman [39:11]
"You're not going to survive if your mental health isn't taken care of... find those moments of peace, zoom out, and be fully present with your family."
—Roger Roman [33:20]
"Empowerment—that’s the word. Did I build something that actually helped people? Did I empower? That’s the legacy."
—Roger Roman [36:46]
"I like to think of us as the TurboTax for justice tech—helping you do what you could only do with a lawyer in the past."
—Roger Roman [43:24]
"Keep that day job. Learn from me—keep that steady foundation and build slowly."
—Roger Roman [28:40]
"Failing forward is the correct term. If you’re not taking something from it, it’s really a loss."
—Roger Roman [09:33]
"Malcolm X... is the embodiment of what we're building—someone who had a rough start and changed his life. Second chances are our ethos."
—Roger Roman [11:56]
"Used to be Notes. I would say ChatGPT at this point, I’m just being honest."
—Roger Roman [45:11]
Website: legalease.com (all social links there)
Roger on LinkedIn: Roger Roman (Founder of Legalese)
Roger Roman’s approach fuses tech innovation with a deep commitment to justice and accessibility. Legalese’s mission—to automate and democratize expungement—serves as a powerful example of technology tackling entrenched social barriers. Roger’s story offers inspiration, practical strategies, and candid insights for other Black entrepreneurs and founders breaking new ground.