Jonathan Hawkins: [00:00:00] Not every lawyer is the best at everything. You know, there are people that are way smarter than I am. There are people that can try a case better than I can. There are people that are nicer to clients than I am. And there are people that are better at every individual piece than I am.

But there are things that, I can do if I stack them right that, that differentiate me from other lawyers. And it sounds like service and connection with people is probably one of your strengths.

Dwayne Pennant: Yeah. Yeah. And, you know, I think what’s intimidating about being a lawyer is that you’re looking at the finished product of somebody, right? You don’t know what they went through, And you try so hard to overstep those, like your particular boundary, and you might fumble. But I know that I can meet someone, talk, and try to figure out stuff, and then the rest of the things that come along being a lawyer, I think, you know, you can learn.

And I don’t try to do more than I really am equipped to do. And yeah, that works for me.

Welcome to the Founding Partner Podcast. Join your host, Jonathan Hawkins, as we explore the fascinating stories of successful law firm founders. We’ll [00:01:00] uncover their beginnings, triumph over challenges, and practice growth. Whether you aspire to launch your own firm, have an entrepreneurial spirit, or are just curious about the legal business, you’re in the right place.

Let’s dive in.

Jonathan Hawkins: Welcome to Founding Partner Podcast. I’m your host, Jonathan Hawkins. This is a podcast where I get to interview law firm founders and hear about their backgrounds, their stories, and lessons they’ve learned along the way. And today’s guest is gonna be a good one. He is somebody I came across on LinkedIn, and he had an interesting post.

I said, “Man, I, I gotta get this guy on and, and learn more about him and his, his practice.” So, please welcome Dwayne Pennant. He is a lawyer in, largely based in Charlotte, but he’s got a practice in Mash- Massachusetts as well. We’ll let him explain that. Dwayne, welcome to the show, man

Dwayne Pennant: Thank you so much for having me. Thank you. Yeah

Jonathan Hawkins: All right. So, so tell me, you know, what kind of law do you do? What, [00:02:00] what, what areas do you practice? And and I want you to explain, you’re based in Charlotte, but you have a, a Massachusetts presence. So I wanna learn how you’ve, how you did that and how you spend your time between the two jurisdictions

Dwayne Pennant: That’s wild. Yeah, so I practice personal injury and estate planning and probate. And my plans originally I lived in Boston and I grew up there, and I was gonna go to law school there, but one of the schools I, I got accepted into was Charlotte School of Law. And I remember I was flying actually to go to Florida to visit one of their schools, and I had a layover in Charlotte, and I missed my flight.

And end up liking it here, and I was like, “You know what? I’m gonna stay here.” But I always went back home to Boston. So when I became a lawyer, passed the bar, a lot of family and friends were like, “Hey, are you gonna come back up here? Are you gonna have a business?” And I was like, “I don’t know about that.”

And then eventually, you know, it, the opportunity came. So I go back and forth between here and Boston. Mostly I’m here in Charlotte, but I try to go back there quarterly. [00:03:00] And it, it’s awesome because I get to go back to see family. I go, go back for the food and, you know, it’s al- it’s always fun. I’m always flying back here with Chinese food with my, in my hands, and they’ll stop me for food. being so serious.

And they’re like, you know, they give me a hard time and I gotta plead with them and say, “Hey, look, you don’t understand, man. I’m going to Charlotte It’s like the the Chinese food down there. I just want you to let me…” You know, so I just, I love it. I love it. I love it

Jonathan Hawkins: Did you, did you have to take two bar exams?

Dwayne Pennant: I did. Yeah. Yeah. So I didn’t pass the bar my first time or second time.

But I… So I went to UBE, in North Carolina then, and I passed that. And I think before that I took the New York UBE and passed that, and then I waived into DC, and my plan was just to be licensed federally because that way I can practice in whatever state federal job was available. And I ended up going to the magistrate’s office and, you know, from there took another bar exam and then waived into Boston, or Mass, and then, yeah.

So took multiple exams, yeah

Jonathan Hawkins: I took two exams [00:04:00] too. That’s enough for me. I’m not g- I’m not taking anymore.

Dwayne Pennant: AMA Saedi. Osa?

What’s

Jonathan Hawkins: Yeah. I said, “I might waive in, but I’m not, I’m not taking another bar exam.”

Dwayne Pennant: I’m, you know, I, I think the bar exam can be very intimidating, obviously. I have some wild stories, but once I figured out what they were looking for, I was like: Hey, look, I don’t mind taking it again, because I wanted to see how high I can get on the score. That’s just my mindset. But yeah, I, I, honestly, I wouldn’t mind taking another bar exam just to see if I can get a better score, and that’s kinda wild, but that’s just my mindset.

Jonathan Hawkins: Well, not for me. So, okay, let’s, I wanna explore that a little bit. So you’re from Massachusetts, you’re from Boston, so I get it. You want, you, you wanted to be in both. You go back there a lot. How do you, how do you manage… And I’ve looked at your LinkedIn, and you’re going to, you know, Massachusetts bar events, and you’re doing stuff in Charlotte.

You’re pretty active out in the community, in both communities. How, how do you you know, client develop in the two different places consistently?

Dwayne Pennant: Yeah. Yeah. You know, you were saying [00:05:00] that and the thought came to mind service to many leads to greatness. And I don’t know why that came to mind, but like when you get active in the community wherever you are, your name’s gonna spread and, you know, you get to meet people. You get to, you know, keep your ears to the ground and figure out what’s going on.

And I’m active in Boston as it relates to events, but I’m also active here and it, it helps it balance off, it helps to bridge the gap with what kind of new trend for law works, what kind of, you know, just things that work for different lawyers. So for me I don’t have a crazy schedule. I’m not trying to be a, a large firm that makes a lot of money.

I, I just wanna be able to feed my family and make an impact. And that allows me to take some chances where, “Hey, look, I’m gonna go to Boston for a week,” and my wife said, “Go ahead. That’s fine.” I’m gonna go to these events so that it’s not a waste of time. I’m not going there for vacation. And then when I come back, you know, I’ll try to hit up these events here in Carolina.

So it, it works out good where it seems like I’m really active, but in all honesty, it’s no different than working a 40-hour job

Jonathan Hawkins: Yeah. [00:06:00] Well, I commend you on that. It’s it would be a challenge. And, and I know firms that have multi offices, but usually they have pe- different people in the different offices, but it’s all you. so

Dwayne Pennant: Yeah,

and I, I wanted to give a shout-out to, you know, so I, I was able to hire a part-time employee, and I do have two 1099 paralegals that do work for me. And I think what really has helped me to take on that workload, even before having them on, was working in Mecklenburg County one of the highest volumes in terms of courthouse.

And eventually, you know, I’ll talk about how I got to the courthouse, but working there was so crazy in terms of just being busy, and I felt like, man, if I can do it here, I can do just about any other job anywhere else. So when I went on my own and I was able to control my hours and the volume, it was a relief to me.

So I was like, “Oh, this is not bad.” You know what I mean? So I don’t mind taking the chances and, you know, adding on more stuff ’cause I know that it wasn’t as bad as working at some other places where you have to be there and have to do all these different things, you know?

Jonathan Hawkins: So let’s talk about after law school. I saw this, I don’t know if I saw this on LinkedIn [00:07:00] on your website or maybe both just finding a job after law school and the process you went through and sort of where you ended up. I think that’s a cool story I wanna hear more about.

Dwayne Pennant: Yeah. You know, so you, watch different television shows you think once you, you know, graduate law school, you’re gonna have all these people wanting to work with you for a while, having you work at their firm, but that’s not the case for me. Our school was for-profit and it was very, you know, a very large school, and I think it made people not wanna hire folks from our school.

And my thought process was, you know what? If I can go and volunteer or work at a courthouse, I would do that. My wife at the time well, she was working at Hot Bench. This is like a place that goes to different, like, Judge Judy Show, and she’ll go to different jurisdictions or courthouses and look at their shucks and find, you know, juicy cases that they can travel out to Ca- California.

And I asked her, “Hey, where would you go work at?” And she’s like, “I work at Catawba County.” I said, “What about, you know, this County?” Said, “Nah.” And literally, I, I went [00:08:00] down there one day and just after, you know, I didn’t pass a bar and I wanted to figure out where to go, and I went down and I said, “Hey, look, you know, I’m out of law school. I don’t mind coming here volunteering.”

And you know, she’s like, “I have a lot of applicants.” And one thing led to another and she gave me a job. And I loved being there because I felt like I was still within the legal system, even though I wasn’t an attorney. But I was able to see how other attorneys operate, get a feel for the clerks and, you know, what kind of law it would look like on the other end, and eventually, you know, I ended up in Mecklenburg County.

In between that I was doing doc review. You know what that is.

Jonathan Hawkins: Yes.

Dwayne Pennant: And that’s work. I don’t wanna disrespect, but it is sometimes very difficult work to do. I remember being there thinking to myself, “You know what?” This is in between Catawba. I was like, ” I can’t be here.”

And I remember thinking, “I’m in Charlotte. I don’t want to go to Catawba because it’s too far now. Let me try to get something closer.” And I decided I was gonna go follow the clerk wherever she went because I wanted to have her see my my face and my application. And I remember telling people within my pod, I was like, “Hey, man, I’m gonna go [00:09:00] meet the clerk.

I’m gonna give them my application.” They were laughing at me Yeah, I’m gonna go meet Bill Gates. And I’m like, “No, I’m gonna do it.” And I just left one day after work and I’m driving to this place that she’s gonna be at. And sure enough, you know, I walk in and she’s in the very back, and I sit through the entire event.

And I walked out after her and I said, “Hey, look, my name’s Dwayne Pena. Here’s a resume. You come work for you.” And she’s looking at my resume and I’m like, “Oh man, this is so stupid.” And I just said, “Hey, look, Les Brown says you gotta be hungry.” She looks at me and she goes, “I love Les Brown.

Walk with me.” And I was like, “Oh my goodness, it worked.” And you know, this, that feeling of just like not wanting to satisfy doing one thing and then taking risk, you know, and she loved that. And she went back and told someone in their workplace, “Hey, pull this guy’s application.” And I remember telling her, “If you hire me, I’ll do whatever it takes to make, you know, this courthouse look good.”

And that became sort of like a rule. She always saw me and I, I remember telling myself I always gotta make her look good. And I was a clerk in civil department for a grant position, and I worked really [00:10:00] hard. I mean, I would take everyone’s files back. I would just do whatever work they wanted me to do.

And they were like, “You’re a lawyer. Why are you doing this?” And I was like, “Man, you know what? You guys are the ones that make this thing go around, and I wouldn’t mind loving to like learning from you guys and whatever.” And she said, “Hey, look, you’re working so hard, we’re gonna promote you to more work.”

And that was in the estate department. And that’s where I kind of got a feel for what I’m doing now in probate. And I got tired of that and wanted to leave and she was like, “Hey, I think you should stay.” And I was like, “Nah, I’ve had enough.” And an opportunity opened up as a magistrate. She’s like, “I wanna nominate you for this.”

And I was convinced I wasn’t gonna take it. And my mentor said, “Take it. It’s a good opportunity to learn.” I took it. And, you know, it just– I felt like my path was being like laid out for me all because I wanted to go volunteer, you know. So I, I just kind of ran with that.

Jonathan Hawkins: You know, that, that’s, that’s inspiring. And I think for other people out there who, you know, maybe are just starting or thinking about things, you can ma- I mean, you said your [00:11:00] path was laid out for you. I m- maybe, but you also went and sort of made your path. I mean, you didn’t sit back. It didn’t come to you.

You had to go make it happen. And I think a lot of people, even lawyers who have been practicing a long time, they just sit behind their desk all the time. It’s like, no, you gotta get out and do stuff if you wanna grow your practice, grow as a person, whatever it is. So what, what was it in you? Were you always like that?

Where you’re like, “All right, I’m just gonna go do these things”?

Dwayne Pennant: Yeah, no, I, it’s weird. My wife and I will talk about that. She’s like, you know, talk about just how we kind of process and troubleshoot. in some ways, you know, I, I, I think a lot of it is just, you know, maybe upbringing. I don’t know. But I was that kid that kind of like took chances.

I was a troublemaker partly in, in high school. Got into fights here and there, but really I was a nerd just trying to fit in. And, I remember I would be in the more risk-taking side, and I felt like this whole experiment of law school, it was just me trying to not satisfy with working at John Hancock and just doing 9:00 to 5:00. I [00:12:00] wanted to do, to do more, and I, I felt like, hey, look, you know, just try the hardest thing. If you fail, what’s the biggest deal? You, know, you learn something new from it. So that kind of creative thinking it showed up when I was even– after I graduated law school. I remember I would apply for jobs and they’ll send out an auto-reply, and I would reply back to that.

I was– I w- I wanted to make sure my ti- I would literally, I would reply back to that. I would, I would just do wild stuff, man. Like I said, show up where clerks were, ’cause I wanted to, I wanted to distinguish myself. I, I didn’t have the grades. All these diplomas in the back here, they’re not mine, it’s my wife’s.

So I think I might have one little small one in the back here. right? So I’m not, I’m not that kind of book-smart guy, but I am creative. I, I feel like I have some level of ingenuity, and I feel like if I’m able to, to connect with people and I work hard, it opens a door for me. And I, I always try to lead with a spirit of I wanna learn, and I think they love that, you know?

And I, I think just being able to not satisfy or not settle has been helpful.

Jonathan Hawkins: Well, and the other thing about the story that I like is no matter the [00:13:00] job, you’re going above and beyond. You know, I always tell people, and I try to, have tried to do it myself, is you, you wanna be known for something. You wanna be good at something. You want people to say, “I can rely on that person,” instead of just punching the clock.

you know, you were going way above and beyond, which it sounds like eventually led to this magistrate position, which is pretty cool. If you had just been punching the clock, I don’t think that position would’ve opened up for you. I don’t know. What do you think?

Dwayne Pennant: 100%. I, I remember people there were like, “You’re working too hard.” And part of it was, I think, coming off of studying for the bar exam and knowing how much time and energy I put into that. I c- I just couldn’t come to a job where I just sat down, and I wanted to create more friction because I felt like friction is how you grow.

And I would say, “Hey, look, you know, I know you’re not using that,” or, you’re done with your pocket, take it back.” And I wanted to stack and keep on stacking stuff. So yeah, I, I certainly don’t wanna settle. Even now as, as you know, I feel like I’m– things are steady, I wanna push the boundary because I feel like [00:14:00] in my mind, you know, it’s about growth.

I think if you keep growing and growing and growing, you can, you know, lay a good track for yourself. So yeah, 100%. I, I don’t like to settle and I feel like you gotta, you gotta go out and earn it.

Jonathan Hawkins: And let’s talk, let’s talk about it. So you g- you got nominated or appoi- did you get appointed? How did

Dwayne Pennant: Yeah. So the, the way it works is that you, the clerk of court nominates you, and then you get appointed by the superior district court judge, I think, superior court judge. So, you know, it’s a matter of applicants and they’re like, “Hey, of these people, I would nominate that person.” And the reason why I was nominated was because…

And she would tell me, she’s like, “Hey, look, you know, I have all these voicemails of people that, you’ve helped in the state’s department. People would stop me in the hallway and say, ‘Hey, there’s a guy up there that went way above and beyond.'” And for me, it was just a matter of if I can serve the people here for free, I feel like I can do it for money.

And, but also I, I was sympathetic towards people that were coming into my office or my cubicle that just lost somebody. You know what I mean? So being able to connect that way [00:15:00] allowed her to say, “Hey, look, you’re gonna do a good job regardless of where you are.” So she nominated me for that, for that merit, and then someone, you know, appointed me.

Yes.

Jonathan Hawkins: That’s cool. So you’re getting, your boss is getting voicemails about you. People say, man, that, that’s like, you know, the best Google reviews nowadays, right?

Dwayne Pennant: And I didn’t know that. I didn’t know that. until you know, we’re in the, the interview process and I I left and then after she told me I played the messages for the people that are in there to hear. And I didn’t know this. This was, it was an awesome thing. I remember getting someone that they came late for the appointment and if you’re like 10 minutes late 15 minutes late, you’re supposed to cancel it.

And I said, “No, you’re fine. Come inside.” And I had this little music playing. It’s my own cubicle, by the way. And ended up being that she was like, you know, the clerk’s like friend or somebody, and she left and said, “Hey, this is a, this is a guy up here that went, you know, he should have canceled my appointment.

It was so relaxing talking to him, like, who is this guy?” And I, I, I really appreciated that because I felt like I was watching other lawyers and I was like, “Man, I don’t, I don’t have their skills. I don’t have that, I don’t have that.” [00:16:00] But I was like, “You know what? Just, just be comfortable in what you have and do what you do good.”

And I, I– that’s me talking to people and engaging and finding out how I can help them, and that, that worked out good for me

Jonathan Hawkins: That’s another good point. You know, not every lawyer is the best at everything. You know, there are people that are way smarter than I am. There are people that can try a case better than I can. There are people that are nicer to clients than I am. And there are people that are better at every individual piece than I am.

But there are things that, you know, I can do if I stack them right that, that differentiate me from other lawyers. And it sounds like service and connection with people is probably one of your strengths.

Dwayne Pennant: Yeah. Yeah. And, you know, I think what’s intimidating about being a lawyer is that you’re looking at the finished product of somebody, right? You don’t know what they went through, And you try so hard to overstep those, like your particular boundary, and you might fumble. But I know that I can meet someone, talk, and try to figure out stuff, and then the rest of the things that come along being a lawyer, I think, you know, you can learn.

And don’t try to do more than I really am equipped to do. And yeah, that [00:17:00] works for me.

Jonathan Hawkins: So, so the magistrate position, what kind of stuff were you doing there?

Dwayne Pennant: Yeah, so we’re the front line, the first interaction, you know, a defendant has with the system. And I, I remember like getting murder cases that come before you and you have to like, obviously, prime probable cause to charge that person, but you’re getting things that you’re like, “Man, I can’t believe this happens in Charlotte.”

And you’re seeing people at, their, at their worst, people that are getting, you know, involuntary committed. You’re seeing stuff. I mean, you’re, you’re there. It’s almost like night court ’cause it’s 24 hours, right? And there’s three shifts, and our shift was a second shift, and we’re getting stuff that’s like the courthouse is about to close.

And then you just, it’s just wild stuff. Like it’s a whole other, you know. But I, I really appreciated the other staff that was there that kind of like, “Hey look, you know, you wanna watch out for this, watch out for that.” Also I, I, I thought it was interesting to read the interaction that officers had with magistrate.

You know, they walk [00:18:00] into your courtroom, they’re like, “Your Honor.” And I wasn’t used to being called these little names, So, And I was like, “Wow, this is kind of like wild,” you know? So it was very humbling. And you know, at the same time you realize that you’re, you’re, There’s a lot of power you have, it was just something that I really appreciated. Like I, I remember, you know, if it snowed or, you know, they’ll come get you and I was like, “Man, this is like, this is, this is, this is wild.” So I– For me it was more or less like I didn’t realize these little things come along with that. But then the responsibility also, I would go to a restaurant and the people are looking at me and I, I’m like, “I don’t know if I did something And I’m walking out and they were like, “Hey, you’re that magistrate.” And I like, “Oh, someone’s gonna get mad at me.” And they’re like… I was like, “Yeah.” I was like, “Hopefully I, I dealt with you fair.” “Sure did.” I was like, “Woo,” You know? So I, I felt like it was just, you know, the responsibility of, of being someone that can decide case fairly and, you know, or just a, a complaint fairly. So yeah yeah

Jonathan Hawkins: Yeah, I have a buddy that, that was a judge for a number of years, and he said, [00:19:00] you know, when he was a judge, every joke was the funniest joke. Every- everybody’s laughing at his jokes, and then the second he wasn’t a judge anymore, they’re not laughing at his jokes so much anymore.

Dwayne Pennant: 100%. 100%. 100%. Like it, it was, you know, it, it was… Yeah. And people, there’s also the other side of it where it, it got to some people’s head, and I, I remember thinking to myself like, you know, with, you know, just the responsibility, you really have to sort of be careful the perception that people have of so

Jonathan Hawkins: that for two, three years or so, and then eventually you went out, I think it was around 2023, to start your own firm. What, what was the impetus? What got you said, “All right, it’s r- it’s time. I wanna go practice law on my own. I wanna do this”?

Dwayne Pennant: Yeah. You know, so there’s– being a magistrate can burn you out a little bit. Mecklenburg County was on the, the cutting edge of, you know, sort of e-courts and some other stuff, and the responsibility was getting more for us, I, I didn’t want that. I, I didn’t want that. And I felt like I had watched different attorneys, whether it was at the courthouse or even just in [00:20:00] my realm of the magistrate, I said, Look, I can do what they do.

And I remember talking to my mentor, I said: Hey, look, you know, w- what am I going on my own. Like, hey, what are some things that you did? And he’s like: Well, look, why don’t you get a business plan? And I was like, “Okay.” And I did, and I remember getting a, a, it was like 20 pages, and I put so much effort into it.

And I remember being prepared to go out, and the whole idea was being able to sort of buy back your time. You know, I, I spent all this time going to law school, all this time, like, I was a party guy, and then law school hit, and then I got married in law school, right? So I felt like my wife and I, we always had this, like, it was always a high-stress thing where we always had to just study and never engaged in just being a couple.

And I felt like if I can buy back my time, whether through getting clients and getting more cases, I can, you know, spend more time with my family. So that was really the goal, was to be able to sort of, you know, just be able to buy that time back. And I remember it was like the first [00:21:00] month or so, of on my own, we’re here, and I, I think the pipes…

I live in Charlotte, and their system is more reactive than it is proactive to maintaining the pipes. And sewer literally like, is like flowing into our house. And I was like, “My goodness, man.” And I remember like my wife was like, s- she was just it was freaking out. But in my mind, I’m like, I’m thinking, “They knew it was wrong.

I’m going through something. this,” might be my first case.” So, you know, I just, I was looking for opportunities wherever they came.

And sure enough, it was, it ended up being one of the… No, my first So it was, it was one of those things where it’s like, you know, I, I wanted the opportunity to provide for my family, and what more opportunity than just to, to defend them?

So it came that way, and I just, you know, it was that, and then I would go to Boston and, you know, I would go to events. I would look at listserv. Someone didn’t want a case, you know, I would take it. And that case led to someone saying: “Hey, look, I, I realize you did Wilson trust.” And then, you know, so it was just [00:22:00] one after the other.

And I wasn’t trying to be greedy in terms of wealth. I, I have a very simple lifestyle. So I’d saved enough money where I knew, hey, I can, I can manage this, that, and that. And, you know, I had opportunities to be home with my, my daughter. So it wasn’t like I was out here and I was trying to fend for food.

It was just like, okay, you know, here’s my ex- expenses. here’s what I can do to network, here’s the opportunities I have, and I just took advantage of all of them.

Jonathan Hawkins: so you spent… That, that was good. You spent a lot of time preparing. You got your 20-page business plan. When you started, I mean, you’re coming from government, so did you have clients or did you have a potential set of clients when you opened your doors?

Dwayne Pennant: Yeah, I did. I think when I left the courthouse as a, as a mag- not a magistrate, but as a estate clerk, there are people that would come there and were still looking for me. Like I, I remember just, it was wild. People were still referring people to come to the courthouse to see Clerk Dwayne. [00:23:00] and when I left, they were still referring people, “Hey, go see Lawyer Dwayne.”

and it was just, it was, it was really awesome. I mean, one of the best cases I have right now came from there and I, you know, I’m humbled by that. So being able to have a presence at the estates department allowed for referrals to come. Some cases are wild, you know, but at least they will call me and I’ll spend time talking to them.

If I can help them, I would. If not… And they will think about me later on say, “Hey, you were so helpful to me at, at SCE.” So yes. Nothing criminal-wise, but just more for estates and probate

Jonathan Hawkins: That’s really cool. So you mentioned a minute ago, like you started your firm and then within the first month or so you had to move out of your house ’cause the pipes backed up or whatever. I mean, it’s hard enough getting a firm off the ground, but then to have to move, and you had, I mean, you had kids. It

Dwayne Pennant: Yeah, and my wife was… We found our second… Yeah. And this, you know, and so a lot of it is just how do you respond to circumstances, right? For me, I [00:24:00] troubleshoot I say, “Okay, you know, I’m, I, I’ve, I’m, I have a strong faith, so I’m like, “This is an opportunity to me. This is how I see it.” And I can complain about it, but it’s still gonna be here.

So for me, it was like, okay, how do I navigate this circumstance? So obviously, we’re at the hotel. My wife is– she’s working at a law firm. I’m home with my daughter, and I’m trying to navigate. But that forced me to have someone answer my phone, right? Instead of me doing it. And it also forced me to, to, to be able to structure how I gave her naps.

You know, I remember being on the on a consultation and I, I can hear her in the background crying, and I’m coughing trying to hide her crying, you know? So you, you do whatever you can, but, like, that pressure produces something, right? And I felt like, okay, not every day is gonna be like this, right? So this is the worst, and I was able to navigate that.

The other one’s gonna be better. So that was my mindset.

Jonathan Hawkins: That’s true. You get through that, man, it’s, it’s all downhill after that, right?

Real quick, if you haven’t gotten a copy yet, please check out my book, the Law Firm Lifecycle. It’s written for law firm owners [00:25:00] and those who plan to be owners. In the book, I discuss various issues that come up as a law firm progresses through the stages of its growth from just before starting a firm to when it comes to an end.

The law firm lifecycle is available on Amazon. Now, back to the show.

Jonathan Hawkins: So let me ask this too. So you went out, you, you did work, I guess, as a clerk in the probate area, so that makes sense as to why maybe you would gravitate towards that practice area. But you also do personal injury. I don’t know if you thought about, I mean, you were a magistrate, that sort of criminal type stuff.

How did you decide which practice areas you wanted to focus on for your firm?

Dwayne Pennant: Yeah. So, my mentor does personal injury Eldon Goodhue in Topsfield, Goodhue in my office is at too. And I remember thinking about his lifestyle. You know, I was, I would, I would go and look at lawyers. I was a troublemaker back then too, so when I wanted to go be a lawyer, I would like reach out to my old lawyers that helped me out.

I had to make sure I didn’t owe money first, and I was like, “Hey,” you know, “Can I come shadow you?” They’re like, “Yeah, you can, you can shadow me.” And, but I [00:26:00] liked how he was operating his firm. I liked his free time. I said, “Okay, now what, what do you do?” And he’s like, you know, I do this,” and, and he laid it out to me.

Ironically, he was also the one that encouraged me to go to law school. But I was a client of his for an auto accident, and I was asking him questions to try to get more value for my case, and I was probably in my 20s. And he’s like, “You know, you should think about going to law school.” And I would give him all these, these excuses as to why I couldn’t do it.

And then when he chopped them down, I was like, “Okay.” So it was the same mentality I had as to like, “Hey, I, is this hard being, you know, a personal injury attorney?” He’s like, “No, you just gotta do this, that, that, that.” And, you know, I literally just took his advice, did everything he told me to do, and it was, it was cool.

You know, it- I- the way I see it too is that when I do wills and trusts, I’m making friends, and they’ll come back and ask you for stuff ’cause you’ve done, you know, their will or their trust, whatever like that. And then when they find out you do other areas, especially if you did a good job for them, they’ll trust you.

So they were all, these are all warm transfers to me. So I knew I wanted to [00:27:00] do personal injury because the lifestyle that he kind of had, and then tweaked it with my own

Jonathan Hawkins: so just based on your work in the clerk’s office, magistrate, obviously you, you, you work well with people and you leave a good impression. What’s… Do, do you have a way that you stay in touch with your clients now so that they will keep coming back, referring people to you?

Dwayne Pennant: Yeah, yeah. And I, you know, I I should probably say one of the reason why, you know, I even ended up in probate was, you know, when I was 24, my sister passed away from lupus, and I had to go to the courthouse and sort of like navigate probate and guardianship. And I remember thinking to myself like, “This is like, this is dreadful.”

I remember saying, “If I can get through this, I’ll always keep this desire to be a lawyer in my, my forefront.” And then when he kind of watered that seed with the personal injury, to me it became clear I’ll do that and probate, you know? And what I wanted to do was I wanted to do what those clerks that I met when I was going through that process with my sister, [00:28:00] they were so friendly to me.

I told myself, “You know what? I wanna be able to be like that when they come uh, to where I was a clerk

when I was a clerk or even when I meet clients.” I’m always trying to sort of like just talk to them as a human being, just engage them and, you know. and that sort of disarms them in terms of just being able to connect.

And they always feel like we had a genuine connection, which makes them even call me for unrelated things to law. And that, again, that, that creates a referral for me because they’re like, “Now I’m a friend,” as opposed to them being some lawyer person

Jonathan Hawkins: I mean, as somebody who believes in relationships and the power of relationships I try to maintain as many as I can, but it gets, it gets hard, man. There’s just, there’s only so much time in a day. So how do you manage it all? Especially between Charlotte and Boston. You’ve got… You’re, you’re, you’re, you’re juggling a lot there.

So how do you really, I guess, make your days, make them efficient, be able to get through this and, and [00:29:00] really connect with people and do the things you gotta do every day with your family and working?

Dwayne Pennant: That’s, that’s it. My family. My family becomes sort of like my, my guardrails. you know, you get to a point where you feel like things are comfortable and you can only imag- manage so much calls and so many things in a day. And yeah, I, I use my family as a boundary. Like, I, I have a strict regimen in terms of, you know, when I try to go to bed.

I go to the gym. I try to go to gyms that are near my, my daughter’s school, so there’s no excuse for me not to work out. I try to allocate certain times where I can take wild phone calls, you know? And then if I gotta pick them up, I lock off early. So I know that between these set times, I have an open schedule.

Other than that, it’s family time. But there are times where, you know, you know what it’s like to be a lawyer, so there are times where because you, you work for yourself, you can push those boundaries. So that’s a part of like, you know, having boundaries that’s good, but then when you’re kind of flexible you’re your own, your own boss, you can, you can spend hours and hours.

So I try to remind [00:30:00] myself, “Hey, look, if you don’t have enough for yourself, you won’t have enough for them.” My family becomes sort of like what helps me to sort of navigate these things. whether it’s when I lock off my time, when I wanna, you know, find a reason to go on a trip, that’s how I do it

Jonathan Hawkins: Speaking of time I saw one of your posts, you recently won a, a trial. I think you said it was your first win. And I know trials can suck all the time out of you. So, so how did, number one, how’d it feel to win that trial? And then, you know, h- how do you, again, sort of balance the guardrails that you’ve set up

Dwayne Pennant: I felt like I was sort of like, okay, I can do that. I’m like other guys or ladies that do it, and I– it felt like, okay, great. I, I got that one out the way. I think The hardest part about that was knowing whether you could do it or not, and just being able to do it, you know, and get through it and be successful. It, it does a lot for your confidence. The other part of that is, yeah, it is time-consuming when you’re solo or, you know, you can’t have probably [00:31:00] certain things for you. And I think being over-prepared was awesome, but I also realized how time-consuming it can be, right? So you start to get ideas as to if I were to do this again, what are, what are ways you can maximize some of the stuff right here?

So it was a win-win s- scenario for me, you know? Obviously it was a– it might’ve been a two-day, I think it was a day or two. But yeah, it, it was a great experience and I, I just, I felt good just getting that out the way, know,

Jonathan Hawkins: and, and prepare for trial, you real- there’s alway- there’s always more you can do. Always. There’s, you can always do a little bit more to prepare, and sometimes it’s hard to say, “All right, this is it.” S- so yeah. Well, congrats on that. That’s awesome. So does it make you wanna do more?

Dwayne Pennant: Yeah, yeah. No, I, I mean, I think part of being a lawyer sometimes you think you’re an imposter, and I think you look for those opportunities to validate yourself, right? And I try to enjoy the process, and I, I love competing. I, I love the idea of, like, winning, right? So yeah, I think I would love to do more [00:32:00] just to be able…

Especially when you have a good case, when you know the facts are on your f- your side. In this scenario, you know, you’re dealing with a dishonest defendant or dishonest, you know, party, so it, it felt like it was a, a better win for me. But yeah, I would love to do more

Jonathan Hawkins: are you a true soler or do you have, do you have help?

Dwayne Pennant: Yeah, yeah. So I mentioned I, I just had a part-time person. I have a 1099 employee two paralegals that do work, so. And that’s the hardest part too, is delegating those tasks, right? Where you like, you feel comfortable giving up your little baby here that you’ve been working on for so long. But yeah, I, I do have help, and I, think what I do is I try to give the administrative stuff to them, and then allow me to work on the things that I really want to like, you know, just excel at certain parts of law.

Um, But yeah, I do have help

Jonathan Hawkins: And so you’ve got… Let’s talk about your two practice areas again. So probate, estate, and personal injury. Those are two very, very different practice areas. Very different systems. All of it, the way it works, very different. How do you manage those two very different practice areas? Do [00:33:00] you, do you spend more time on one versus the other, or are they sort of e- about equal?

Dwayne Pennant: I have more I think I have more probate cases. I look at the probate cases as like leave, turn on lights, like they pay for the light bills, and then the PI ones are the ones that like, like home runs. But yeah, I, I, think the, the PI ones are the ones that, you know, it’s pre-litigation, right?

So you know that it’s a demand letter, medical records, that kind of stuff. It’s when you get into like deep litigation that it becomes more time-consuming. I think with the probate cases, it’s more administrative stuff, right? until, you know, you have to do something that’s wild, but it’s, it’s not that hard.

I, I consider it to be like law school. You’re handling two subjects. Um, And once you get the civil part of it, it’s, it’s the same. Everything else is just learning law. So it isn’t as hard as people think it is. I remember talking to one of the, one of my when you, when I first went out on my own, I had to reach out to a few [00:34:00] people that help you with new firms.

And this lady was like: “Why do you wanna do that?” And she was just telling me these things, and I can tell that for her, she couldn’t understand that. My mentor was like: “This is a great idea because people always die, and you can always have, you know, and, and, and accidents happen.” So it, you know, for me, it was natural because of this, the probate part, my sister, and then my experience with other attorneys that helped me.

And I think just for me alone, accidents happen a lot in Boston. They happen sometimes here a lot in North Carolina, but people always pass away, and people always need some kind of probate. So for me, it was just natural.

Jonathan Hawkins: So let’s talk about marketing, business development, lead gen. What, obviously we talked about your relationships and, and how you do that stuff. Is there anything else you do? How do you go out to develop clients, and how do you split that? You know, we talked a little bit about splitting the time in terms of working the, the probate versus personal injury, but how do you go about marketing and where do you [00:35:00] invest more of your marketing time and money and budget on the two practice areas?

Dwayne Pennant: Yeah. So, you know, the, the, probate stuff comes from my interaction with the clerk’s office. I’m the co-chair for the estate planning and probate committee in Mecklenburg County. So whenever I have events there, I’ll, I’ll post them. As it relates to like the PI stuff, I, I don’t have big settlements I can post, right? But what I try to post is an experience I might have had with a client or something like that, that I know people can resonate with.

For marketing, I found it natural is like it’s if you’re transparent and vulnerable, people are gonna react to that. to that. And I think for me, I get more interaction when I’m telling someone a vulnerable side of me as opposed to telling them something that I try to impress them with. I think that part really helps in terms of getting interactions and engagement marketing.

The events I do, I’m very social, so I try to go to these like, major bar events [00:36:00] or any annual events that happen, and that allows me to stay connected to other lawyers. And I to other lawyers, and I post that experience and then people that didn’t know I was a lawyer see that post. People that know, you know, I’m a part of that community see that post, and it, it, it sort of generates referrals.

My first one came for estate planning that way. So I, I just try to take what’s organic within my realm and share it in a sincere way that I think people can either get one or two gems from. And it helps me either them refer me to someone that they know because they say, “Hey, this guy’s pretty nice.

You can trust him.” Or it validates me that, “Hey, this guy’s active. I saw him at pro se service,” and

Jonathan Hawkins: you on LinkedIn, so obviously you’re there. Are you on other social platforms? Do you utilize those? Do you have any traction on those?

Dwayne Pennant: Yeah. You know, I, I tried Instagram. I had some guy views one of my posts and, [00:37:00] you know, I– there’s some things I can probably do, but for the most part it’s really LinkedIn and Facebook. I don’t– I have my own Facebook page, but I’m still not comfortable posting certain things on my business website or personal one.

So it’s, it’s weird. I I only operate within LinkedIn and Facebook really. That’s it

Jonathan Hawkins: Yeah. I’ve, I’ve got some other pages that like this podcast and thing gets posted to, but I’m really only active on LinkedIn. And each platform I found, each platform’s different, and like I tried at some point to, to do some Instagram and I just don’t understand it and I just don’t feel like learning it

Dwayne Pennant: What do you call it?

Jonathan Hawkins: I feel like it’s a whole different set of rules, right?

Dwayne Pennant: Yeah. Yeah, absolutely. and it’s like you also like look at what other people are posting, right? And depending on what you’re trying to do, you, you’ll find like some things work, some things don’t work. So yeah, 100%.

just-

Jonathan Hawkins: Okay. So you’ve been at your firm, I guess, about three years or so now.

Dwayne Pennant: doing my [00:38:00] fourth year

Jonathan Hawkins: so looking back, what, what, what have you learned so far? And how maybe has it changed? What, what were the challenges early on and maybe how have those changed over the years?

Dwayne Pennant: Well, I certainly learned that doing this is possible. I think when you, you hadn’t found success passing the bar, I think it can create, at least for me, the, the idea that you won’t find success and, you know, maybe it’s the Harvard guys, Princeton guys that get it, right? So being able to come out here and to still feed my family has, at least to me, I think it’s Earl Nightingale, he has a quote that says “Success is the progressive realization of a worthy ideal,” right? And that idea of progressive is like, you know, it’s moving towards something. And I always love that because sometimes you compare your, your journey with someone’s finished product.

So for me, being able to be out here, being able to feed my family, that’s, for me, is successful. What I’ve learned from it is that, you know, and I, I said it before to you, the whole idea of being humble in the space has been really helpful. [00:39:00] I think people can relate to you more, they can teach you more, you can learn more.

I think lawyers have looked at… You watch “Suits,” so you see Harvey Specter or some other guys, you think, you know, that’s how it has to be, and that’s not you. And I think for me, being able to be– I’m, I’m very um, you know, I’m competitive. But in terms of learning, I, I think being able to be humble and be willing to learn and, you know, just teachable has been the best and foremost. People will take you on- under their wings, they’ll let you know things that they wouldn’t tell other people because you’re eager to learn and you’re not coming out there with an arrogant attitude

Jonathan Hawkins: Love that. So okay. So looking back, I wanna– we’re gonna flip the question a little bit.

Dwayne Pennant: Sure

Jonathan Hawkins: knowing what you know now, if you could go back to when you started, is there anything you said, “All right, we should’ve, I should’ve done this differently,” or, “Maybe I should’ve done this sooner,” or, “Maybe shouldn’t have done that thing”?

Are there any lessons maybe for people out there that are thinking about starting or getting started that, you know, [00:40:00] everybody on some level needs to make their own mistakes and whatnot, stub their own toes, but, you know, hopefully we can all learn from each other. So is there anything you would tell your own self three years ago?

Dwayne Pennant: Yeah, yeah. I mean, so I had a goal and I was working towards that goal, and I wish when I was going through the dark seasons, I would say, “Hey, it’s gonna be okay. It’s gonna be okay. It’s gonna be okay.” I didn’t do that and I think people abandon some of their goals because it doesn’t look like it’s happening, right?

So, you know, besides getting mentors, besides having a business plan, you know, it’s being able to, to remind yourself that it’s, at least to me, it’s gonna be okay. I think people take chances and do some things because they feel like it’s not gonna be okay. And if I could go back, I would tell myself to enjoy the process.

I think there were times where I could have really enjoyed law school more if I knew in the end I was gonna be a lawyer instead of being so uptight and stressed. I said to my wife this too. I said, “Look, let’s enjoy these seasons that we’re in. I know it might seem [00:41:00] kind of strange, us moving parts, but let’s enjoy it,” you know?

And I think if I can go back and tell myself one thing, it would be enjoy. Work hard, but enjoy it. I was a party animal. I think I gave up some of those things, and rightfully so. But I also, I took on this edge of being so serious that I didn’t enjoy certain things. And I feel like if I can just go back and say, “Hey man, enjoy it,” I would probably have some other stories to tell you.

Jonathan Hawkins: So

what tips do you have for me and others on how to just enjoy the process now, not get too caught up in where we are and where we’re going?

Dwayne Pennant: Well, yeah, I mean, so our profession is, you know, we’re high in, I think, alcoholism, some other things, right? So you wanna be able to enjoy, right? You wanna be able to, we take on so many different, like, you know, just secondary trauma just listening to other clients, right? So if we’re not taking the time to enjoy it, we’re gonna really be stuck in this paradigm or this refractory period of, man, it’s always something negative or something I [00:42:00] gotta deal with.

So you gotta find time to really enjoy it or else you’re gonna get burnt out. And for me, I, I work out, I do these things that I, I try to find a silver lining in all my cases

Jonathan Hawkins: And I’m with you, I exercise every day. It’s every day. And, and it’s been over three years. I have not missed a day. And I do all sorts of different things, but for me, that is therapy. I just, if I did not do that… There have been some times where I didn’t, and I just, it doesn’t, my mental state goes down.

So, have you always exercised or is that something that you said, “All right, this works for me”?

Dwayne Pennant: Yeah. Yeah. I played football. I think I learned structure from, you know, our, our school and I, I took that into… I was a personal trainer and I remember just, just how I felt after a workout. And I think in law school when I was trying to structure how I studied, I made sure I was taking breaks and working out.

And then I said, “Hey, look, how much more important is that? to dealing with more stressful things now.” So [00:43:00] I don’t miss a, I don’t miss… I, I might take off days here, but like it’s consistently helped me to sort of structure my day. I love it when I can go twice a day, you know, especially as I’m getting older and you’re not able to be as agile.

So yeah, I always try. It’s just in me to do that

Jonathan Hawkins: Two a days. You’re, you’re going back, back to football.

Dwayne Pennant: Right. And it, it’s, you know, it’s so sloppy too. You know, I’m not putting in like an hour and a half and, and doing some wild stuff, but I know that my clarity is, is just like, you know, like I hate checking emails early in the morning and I try to do the first thing, you know, some push-ups and then I go to the gym, go for a jog and then come back again.

Especially as you’re getting more comfortable and you can, you know, you can buy a steak dinner here, do something there. You’re like, “Okay, now I gotta make sure I’m getting to the gym ’cause I’m putting on some weight,” you know? So

yeah.

Jonathan Hawkins: That’s right, man. That’s, that’s a constant battle there. All right, so, so again, y- you know, you’ve, you’ve had some I think really cool journey about [00:44:00] how you’ve, you’ve worked hard. You, you don’t just sit around, you go make things happen both before, I mean, in law school, after law school, as you started your firm.

As you look forward, you know, what’s your vision? What, where do you want the firm to go? Where do you want your life to go, your practice? W- what are you, what are you working towards?

Dwayne Pennant: Yeah. Yeah. So I, you know, I tell my wife, I don’t think I’m a lawyer. I think I’m just somebody that likes challenges of certain things. I would love to be able to expand where I can have more time to pursue something new. I love where we’re heading in terms of being able to sort of like, you know…

know, see what happens at the courthouse with people that go through probate process.

So I think people can avoid that. So I would love to do more seminars where you’re educating folks on that. In terms of expanding, I have no desire to be a huge firm where I’m making a lot of money like that. I just, I think sometimes for me, at least for me personally, I don’t need to do all that.

So I wanna get to a point where I’m [00:45:00] comfortable and do more things like you’re doing. You know, I love, I love to have a podcast where I’m, I’m talking to people and getting some stuff from them that can be helpful to someone that’s just starting. You know, so I, I, I wouldn’t mind teaching, but you know, just being able to get to a point where you, you have more time to do the things you like to do.

And for me, that’s either spending time with family, teaching, you know, gym. But yeah, if I can expand, it won’t be to a point where it’s about getting more wealth. Granted, it’s helpful, but I just don’t, I don’t want that to be the… I want, I wanna make an impact

Jonathan Hawkins: So, maybe I shouldn’t ask this question, but you’re from Boston. You still go up there? Do you th- you think you’ll end up back there? I mean, I know you got kids in school. It’s pr- it’s hard to, it’s hard to move them probably.

Dwayne Pennant: Yeah, my wife doesn’t want to live there. I love traveling there and, and, you know, the winters are pretty kind of cool depending on where you go. The food’s awesome. But I get a really good mixture of being able to go there, see family and leave, right? See [00:46:00] clients and leave. I love Carolina. The weather here is cool.

I got a garden I’m growing. So no, I wouldn’t go back to Boston long term. Not that I don’t– I would love to, but I think, I think where I’m at in Carolina has been really blessing to me.

Jonathan Hawkins: You know, I, I almost moved to Charlotte af-

Dwayne Pennant: Yes.

Jonathan Hawkins: after, law school. I had a job lined up and everything, but ended up not. That’s, that’s a story off, that I’ll tell you offline.

Dwayne Pennant: All right. All right

All right

Jonathan Hawkins: But yeah, Charlotte’s a pretty cool town. The thing I remember about it, for people who haven’t been there, you’re driving down the street and it’s called, you know, Smith Street, and you cross the street, and then all of a sudden the name changes because the way it, it’ll turn is, it’s super confusing to get around.

I don’t know if I assume it’s still that way

Dwayne Pennant: Yeah. Y- you know, coming from Boston, I got used to anything crazy down here ’cause Boston’s just a whole ‘nother beast. But yeah, it is like that. What, what freaked me out the most about being in Carolina was there’s no sidewalks in certain areas. Like, I’m used to sidewalks in Boston, so I remember thinking like, “Where’s the sidewalks?”

But [00:47:00] yeah, yeah, you, you find that there is that sort of like change of name and you can, you know, if you’re not GPSing, you can get lost. But after a while of doing it, you kind of figure out what’s what

Jonathan Hawkins: So, uh, we’ve talked about this a little bit. You’ve given some advice, but for people out there, you know, let’s end it with this. You know, what advice would you give to people out there that are thinking about starting their firm, but they’re unsure, they’re not sure they can do it? You know, any advice you’d give them?

Dwayne Pennant: Yeah, I mean, well, first know that you really want to do this, right? Like a lot of people say, “I want to be a lawyer.” And if you’re, if you’re, you know, an undergrad thinking about it, go, go shadow some lawyers that you, you know, you might want to be like and see what they do. When you get into the idea of like, you know, okay, I’m in law school now, I’m looking to, you know, maybe go work for the, the government or whatever like that on my own.

Like, get mentors. See what their lifestyle is like, you know? If that’s what you’re gonna do, write it down. You know, I, I used to write down my goals [00:48:00] and I would read them to myself at nighttime and in the morning, to myself at nighttime in the morning, and I’ll visualize what it’s like to be that way. And I’m surprised those things come to pass.

But mentors have been helpful for me. Writing down my goals have been helpful and obviously like shadowing, going to places where you see yourself where you think you’re gonna be there. So that, that’s been helpful to me

Jonathan Hawkins: That’s great, man. We’ll end it with that. I would sum it up by saying, know what you want and go make it happen.

It’s, it’s, it is not gonna happen to you. You gotta go make it happen. Do what Dwayne did. So Dwayne, thanks for coming on, man. It’s been real fun. It’s been cool to hear your story. For people out there that wanna get in touch with you, maybe they need some help in probate or they’ve got a personal injury case what’s the best way to?

Dwayne Pennant: You can find me at so it’s pennantlawoffices.com. I’m also on LinkedIn, Pennant Law Dwayne Pennant

Jonathan Hawkins: And where can they find you if you’re out and about in, in where do you like to hang out in Boston and, and Charlotte?

Dwayne Pennant: Honestly. So in Boston, you go to any good Chinese restaurant, you might see me there ’cause I’m [00:49:00] a foodie. But in terms of Boston always at a gym. I’m like gym. I do some courthouse events, but really, I’m just a regular guy, man. I, I was at the gym Planet Fitness, and some guy saw me he’s like, “Hey, man, I saw you on television.

You were…” You know, and ’cause he saw an old whatever, and it was so cool. It was so cool. I was like… A- And he, he’s like, “You always work out here?” And I was like, “Man, I, I’m, I’m flattered.” So yeah, I’m just a regular guy. You might find me in a food shop food store or something like that, so hi.

Jonathan Hawkins: That’s cool. That’s cool. All right, Dwayne, man, I enjoyed it. Thanks for coming on

Dwayne Pennant: My pleasure.

OutroUpdatedWebsite-1: Thanks for listening to this episode of the founding partner podcast. Be sure to subscribe on Apple podcasts, Spotify, or wherever you get your podcasts to stay up to date on the latest episodes. You can also connect with Jonathan on LinkedIn and check out the show notes. With links to resources mentioned throughout our discussion by visiting www.lawfirmgc.com. We’ll see you next time for more [00:50:00] origin stories and insights from successful law firm founders.