Veteran Led

What does it take to build a successful law firm while staying true to a mission of serving Veterans?

In this special episode of Veteran Led, we’re reposting John S. Berry’s appearance on Treehouse Talks with host Eric Isham. John shares his journey from military school and ROTC to becoming an Army infantry officer, Airborne Ranger, attorney, entrepreneur, and CEO of Berry Law.

The conversation explores military service, leadership, entrepreneurship, and the evolution of Berry Law from a small family practice into one of the nation’s leading Veterans disability law firms. John reflects on lessons learned from Bosnia, Iraq, law school, and business ownership, explaining how service, discipline, and resilience shaped his approach to leadership.

This episode offers practical insights for Veterans, entrepreneurs, and leaders looking to build something meaningful while staying committed to a larger mission.

Learn more at ptsdlawyers.com

What is Veteran Led?

Veterans know how to lead. The lessons we learned in the military form the foundation for bigger successes in business, entrepreneurship and community.
Host John S Berry, CEO of Berry Law, served as an active-duty Infantry Officer in the U.S. Army, finishing his military career with two deployments and retiring as a Battalion Commander in the National Guard. Today, his veteran led team at Berry Law, helps their clients fight some of the most important battles of their lives. Leading successful teams in the courtroom, the boardroom, and beyond, veteran leadership drives the firm’s rapid growth and business excellence.
Whether building teams, synchronizing operations, or refining tactics, we share our experiences, good and bad, to help you survive, thrive and dominate.

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[00:00:00.680] - Trevor Nealy
This episode features highlights with John S. Berry on the Treehouse Talks podcast with Eric Isham.

[00:00:10.810] - Eric Isham
Alright everybody, I am here with none other than John Berry, Esquire, here in Treehouse Talks.

[00:00:36.700] - John S. Berry
Thanks so much for having me, Eric. Beautiful property.

[00:00:38.680] - John S. Berry
Okay, thank you very much. So, I was doing my research, uh, prior to having you on here, and I said, you know what, I'm just curious, who are the most famous people coming out of Nebraska? And, uh, so Warren Buffett, Marlon Brando, Johnny Cash, Crazy Horse, and John Berry. You're in the top 5 if you Google search most famous people from Nebraska. And I'm only joking this, so anybody, uh, that has been through the state, how many billboards does John Berry have up across the state?

[00:01:11.610] - John S. Berry
I think maybe 35.

[00:01:13.070] - Eric Isham
35 billboards.

[00:01:14.350] - John S. Berry
Maybe a few in Iowa across the river.

[00:01:16.190] - Eric Isham
Okay, so we're gonna get to all that stuff, but I thought that was a fun way to start. So, let's, uh, let's talk a little bit about, um, how you got started. We're going to go all the way back to a very young John Berry. And what drove you to wanting to— we'll start with the military. What wanted you, made you want to go and serve?

[00:01:38.830] - John S. Berry
Part of it was I didn't want to be a lawyer right away. Right. I knew that's something I want to do, take over the family business, but I wanted to have some fun and some adventure. And so, my last 2 years of high school, I went to New Mexico Military Institute in Roswell, New Mexico.

[00:01:50.290] - Eric Isham
Okay.

[00:01:50.770] - John S. Berry
Thought that maybe I wanted to go to an academy, but 2 years of a military school cured me of that. And so, I ended up going to the College of William and Mary and was playing football, got injured. I played with Mike Tomlin, former Steelers head coach, and Sean McDermott, former Bills head coach. And so great leaders, great guys. I was not big enough or fast enough to play at Nebraska, but my friends that went to Nebraska—

[00:02:11.920] - Eric Isham
Did Mike Tomlin play with his glasses on?

[00:02:13.120] - John S. Berry
He was like a skinny, like, you know, like 6'2", 165 wide receiver. He doesn't look like the way he looks now.

[00:02:19.140] - Eric Isham
Okay, but none of us do.

[00:02:20.560] - John S. Berry
Yeah, none of us do. Yeah, that, that's fair. But my friends that stayed at Nebraska, they have the national championship rings from '94, '95, '97. So, but you know what, I got a great education and yeah, wouldn't trade it for the world. I mean, William and Mary is an amazing school.

[00:02:33.550] - Eric Isham
Yeah, sure.

[00:02:33.870] - John S. Berry
And yeah, so I ended up getting injured and decided I did not want to go straight to law school. I want to have some fun. I wanted to become an Airborne Ranger and so became an infantry officer. Got to go through Airborne School, Ranger School, and then was—

[00:02:44.730] - Eric Isham
Where did you get your commission at?

[00:02:46.130] - John S. Berry
William and Mary.

[00:02:47.270] - Eric Isham
Oh, so you went through OCS or I mean through ROTC there.

[00:02:50.470] - John S. Berry
Okay. Yeah, they had this great program like you're I didn't do it my first 2 years, but your second year, you know, like your junior year, you go to this camp in Fort Knox and you can earn a scholarship. So that's what I did. So, I did ROTC my last 2 years because I went to a military high school. All the drill and ceremony crap was easy, right? It was. And I was in great shape. PT was kind of a joke. So, I was like, yeah, I can do this.

[00:03:11.360] - Eric Isham
Okay, so you got your commission coming out of college and then did you go straight in?

[00:03:17.690] - John S. Berry
I did. I was— went right, I think. Yeah. I don't remember whether something got screwed with my DD-214 or it's just like I went in the reserves, but I didn't. I went straight in. You got to understand back then in the '90s, there was all the drawback in the military, right? So

[00:03:33.170] - Eric Isham
that's right.

[00:03:33.470] - John S. Berry
There were, there were a lot of people were not getting the opportunity to go active duty. So, I got, but I went like I got commissioned in May, went into my first class was in my first day of active duty was July 6th, 1997.

[00:03:46.360] - Eric Isham
Okay. Hey guys, quick interruption on the show, but if you are enjoying this content, please make sure you are subscribed to Treehouse Talks TN, like and comment down below. And with that, I'm going to get right back to it. Thanks.

[00:03:59.280] - Eric Isham
Wow, that's interesting. So, your first day of active duty was, let's call it, one month before mine.

[00:04:07.680] - John S. Berry
Oh, great.

[00:04:08.660] - Eric Isham
That's, that's wild. So anyways, and you went to Bosnia, right? That was your first deployment.

[00:04:17.610] - John S. Berry
Yeah. '99.

[00:04:19.570] - Eric Isham
Okay, so you went to Bosnia. So, you've been in for a few years by the time you had your bearings. And then how long were you in Bosnia?

[00:04:25.290] - John S. Berry
About 6 months. And then I got back and I'm like, okay, there's no war because we started bombing Kosovo at that point. And so, we thought it was all going to blow up. We were mostly patrolling Humvees. Now we're going to move to the Bradleys, getting all excited, and then nothing happened. So, I got back that summer and I said, well, you know what, I might as well go to law school.

[00:04:42.290] - Eric Isham
Okay.

[00:04:42.670] - John S. Berry
So that's what happened. I went to law school, but they had this great program where you can— your last year of active duty, if you stay in the Guard or Reserves, that last year is waived and I can get tuition assistance for law school. So, it seemed like a great idea.

[00:04:56.850] - Eric Isham
So, you used your GI Bill for law school?

[00:04:57.990] - John S. Berry
I didn't use my GI Bill.

[00:04:59.110] - Eric Isham
It was a separate program?

[00:05:00.130] - John S. Berry
That was a separate program.

[00:05:00.970] - Eric Isham
Okay.

[00:05:01.610] - John S. Berry
But it was just tuition assistance. So, it was through the National Guard. It was great. And then I was a company commander and then I became a lawyer. And being a new lawyer is tough, especially when my dad was ready to hand over the keys. Hey, take over the firm. He was ready to retire. It was tough. And I went to my battalion commander and said, hey, sir, here's the deal. I'm working 70, 80 hours a week. I'm company commander in the Guard. I'm a new lawyer. I'm partially running the firm now, even though I don't know what I'm doing yet. And I said, I can't do it all. He said you don't have to. Your company is getting deployed. You're going to be a company commander in Iraq.

[00:05:36.110] - Eric Isham
Did he really care about you bitching to him about all your stuff? Hey, don't worry about it.

[00:05:40.970] - John S. Berry
I got a solution. No problem.

[00:05:42.610] - Eric Isham
Yeah.

[00:05:42.790] - Eric Isham
Okay. So, you deployed to Iraq, you're a company commander. And was this with an infantry unit?

[00:05:46.750] - John S. Berry
So that was the other surprise that they gave me. We were in an infantry brigade. They then reclassed to logistics. So not only were we going to deploy, but we were going to reclass. We're not going over as an infantry brigade. We are going over as a I don't remember the term. ASG, Area Support Group.

[00:06:04.880] - Eric Isham
Okay.

[00:06:05.200] - John S. Berry
So, I became the HHC and HHC commander of the Area Support Group.

[00:06:08.160] - Eric Isham
Did you get any kind of additional training on logistics before deploying or were they—

[00:06:12.240] - John S. Berry
I did. I had to. They said you have to figure out logistical branch. Well, because I went to College of William and Mary and Fort Eustis was right there, I said I'll go to Eustis because I love that area.

[00:06:20.700] - Eric Isham
Yeah, it's beautiful.

[00:06:21.320] - John S. Berry
Went there, did whatever, 2-week course, became, you know, qualified as a transportation officer and then later a multi-function, what, multi-area functional logistic. I don't remember.

[00:06:33.240] - John S. Berry
Multi MFA something, but it was like multifunctional logistician or something. And then, yeah.

[00:06:38.800] - Eric Isham
Got it. Easy for you to say. All right. So, you spent how long in Iraq?

[00:06:44.440] - John S. Berry
About a year.

[00:06:45.040] - Eric Isham
About a year. Okay. So, you come back and then you're like, okay, I'm ready to be a full-time attorney now. Did you go into a guard role at that point?

[00:06:51.770] - John S. Berry
Yeah, no. So, I went back to being a lawyer.

[00:06:55.670] - Eric Isham
Okay.

[00:06:56.150] - John S. Berry
And, you know, one of the mistakes we made was we really downsized when I left the firm. And so, I came back to a very small organization.

[00:07:04.230] - Eric Isham
Well, give us, give us a head count on what's small.

[00:07:06.570] - John S. Berry
I mean, less than 10.

[00:07:08.010] - Eric Isham
And oh, wow.

[00:07:09.190] - Eric Isham
So it's way less than,

[00:07:10.290] - John S. Berry
less than 10 people. Revenue was, I think, $500,000, $600,000.

[00:07:13.610] - Eric Isham
Okay. So this is really just a mom-and-pop type. Small local,

[00:07:19.850] - John S. Berry
right,

[00:07:21.070] - Eric Isham
attorney firm, I guess. Okay. Because very far from where you're at today, which we'll get to. But okay, so you get back, you got 10 folks there with your dad running the shop. And was it the focus the same as it is now? Let's talk a little bit about that.

[00:07:35.310] - John S. Berry
You know, it was very similar. We were still doing Veterans disability appeals and we were trying a lot of cases, but it was mostly criminal cases. We had a civil section and a criminal section and a VA disability section. And back then, most of the VA work was pro bono unless it was at the federal court system. So, we didn't have a lot of cases. Lawyers could not get paid at the administrative, uh, agency level back then. So, and now we get paid based on a contingency basis. We only get paid if we win, but back then we couldn't even charge. So, it was— it, it kind of all developed from my father's practice. My father was a famous attorney, uh, had a case called the Green Beret Affair, defended the commander of the 5th Special Forces in Vietnam, and just you know.

[00:08:12.730] - Eric Isham
And your dad was a Green Beret in the—

[00:08:14.870] - John S. Berry
No, he was a lawyer.

[00:08:15.970] - Eric Isham
He was a lawyer.

[00:08:16.690] - John S. Berry
He was an infantry guy who went Jag.

[00:08:18.190] - Eric Isham
Okay.

[00:08:18.990] - John S. Berry
So that's, you know, so anyway, so he, when he started getting these big cases, he became very popular in the Veteran community. And most veterans back then, the Vietnam Veterans, you know, we treated them so shamefully. They were being turned away by the VA. So, my dad would fight for them, and he would do most of it pro bono. And so, then the laws changed around 2007. 2008 that allowed us to get paid for representing Veterans at the agency level. We do it on a contingency basis. So once again, most Veterans who are struggling with homeless or dealing with addiction or unemployment, whatever it is, they could not afford an attorney. So, my dad, like I said, did it pro bono. And then the laws changed, allowed us to get paid. So that was— that became part of a business model. But we were still trial lawyers. We still love to get in the courtroom and try the cases. And a lot of VA disability law is administrative, so it's a little bit different and it's a different type of cat, right? You got to get somebody who loves to research, write, not necessarily get in the courtroom every day.

[00:09:17.310] - Eric Isham
Yeah, it's a specific person that you're looking for that wants to do just that.

[00:09:20.910] - John S. Berry
Yes.

[00:09:21.310] - Eric Isham
Sure.

[00:09:21.830] - Eric Isham
Okay.

[00:09:22.150] - John S. Berry
Probably not a podcast host.

[00:09:23.590] - Eric Isham
Yeah, probably not. So, okay, so you get back, firm has shrunken down a little bit, you land, you're looking around, catching the lay of the land. And then where's your head at? What, you know, what's your entrepreneurial brain picking up? You're like, hey dad, we want to do, I think we should do this. Like walk me through kind of those conversations where your head was at back then.

[00:09:44.120] - John S. Berry
Yeah. I mean, going back, like I had been a paperboy since I was 10. So I was always used to my parents. They were very, I never had rules. I never had curfews.

[00:09:52.500] - Eric Isham
I'm learning a lot now. This is explaining a lot.

[00:09:55.860] - John S. Berry
There are actions and there are consequences. Right. So, and my, I remember I wanted this Schwinn Predator bike when I was 10 and my parents said, well, you buy it. I'm like, well, what can I do? They're like, well, you could do tassel corn, work on a farm, or you could deliver papers. I'm like, oh, deliver papers. This is back when paper boys were being abducted and killed and stuff. My parents are like, yeah, you do the morning route, you'll be fine.

[00:10:11.800] - Eric Isham
Okay.

[00:10:12.080] - John S. Berry
So yeah, so I did the paper, but I wanted to buy that Schwinn Predator. So I, I love that, that dirt bike. So, I got the paper out, bought the bike, and that was kind of from there. I was always like, hey, you can have whatever you want. You just have to work for it.

[00:10:23.960] - Eric Isham
Sure.

[00:10:24.620] - John S. Berry
And so going back to the law, you know, I was always entrepreneurial, but as a young lawyer, I just wanted to be a great lawyer. I didn't care about— and I didn't know anything about running a law firm. And to be fair, so much has changed with technology. I mean, back then there were disputes about whether using email was ethical and then whether cloud computing was secure enough, whether it was ethical.

[00:10:44.650] - John S. Berry
I mean, it's just, it's crazy now to think about it, but lawyers are always— we're always so slow to adapt. And so, you know, I didn't think a law firm could be entrepreneurial back then.

[00:10:55.030] - Eric Isham
Okay.

[00:10:55.610] - John S. Berry
And I loved getting in court. I loved trying the cases, but the business side was, was a mess. We weren't running it like a business. We were running it like a practice. And unfortunately, that's what we learned in law school. You know, it's, it's this almost this elitist mindset, right? That you are such a professional that the business should just come to you. You shouldn't have to worry about marketing. You shouldn't have to worry about all these business things because you're a great lawyer. It'll all happen for you. And that may be true in a, in a large firm where they have a huge administrative staff built out, but we didn't have that. And so you're just like the businessman doing, doing everything, right? You're doing— you're the businessman, you're the lawyer, you're the bookkeeper, right?

[00:11:33.300] - Eric Isham
So did you guys have— did you sit down with the team and say, okay, we're going to change this up, right? We're going to, we're going to turn this into a business. At what point in time did you guys say that and start working toward that?

[00:11:47.860] - John S. Berry
Yeah, unfortunately it wasn't until about 10 years later.

[00:11:49.980] - Eric Isham
Okay. So you were just status quo. You're like, I'm an attorney, I'm going to go practice law. And the business is going to just— you didn't have a business manager there. You didn't have an office manager.

[00:11:58.170] - John S. Berry
We had an office manager.

[00:11:59.150] - Eric Isham
Okay, you did.

[00:11:59.690] - John S. Berry
But it was not— this was— this is not what we have today,

[00:12:02.930] - Eric Isham
right.

[00:12:03.590] - John S. Berry
No. And but I wanted to be a great lawyer. So it's all I cared about.

[00:12:06.390] - Eric Isham
Okay.

[00:12:06.790] - John S. Berry
All I cared about were the cases. I didn't even care if I got paid. And I wasn't— I wasn't making— you know, most of the time I wasn't making money.

[00:12:12.090] - Eric Isham
But were you winning cases, though?

[00:12:13.450] - John S. Berry
I was winning cases. Yeah, it was great. Okay. I loved winning. And that was the thing. You're winning the cases, you're helping people. But yeah, doing criminal cases, doing some civil cases, you know, just doing everything, which of course now lawyers specialize. But back then, hey, that's what you did. And so small firm, and we call it threshold practice. Anything that crossed the threshold of the door, we would take, right? Like, and that's how we ate.

[00:12:35.470] - Eric Isham
Okay, so somebody hit my car, you're working the case.

[00:12:38.390] - John S. Berry
Yeah.

[00:12:38.610] - Eric Isham
Okay. Yeah.

[00:12:39.410] - John S. Berry
And that was, and that was, you know, a lot of cases we probably shouldn't have taken that we took,

[00:12:42.650] - Eric Isham
right

[00:12:43.270] - John S. Berry
And we learned some important lessons from that. But it wasn't until I had reached this point where I had, was very confident in my ability, had won a lot of jury trials, had got amazing results for a lot of clients. And I was in the National Guard, and I was battalion commander of the officer and warrant officer candidate school. And I was so happy to have that job. I thought that was like the best job I had since I was a second lieutenant.

[00:13:08.660] - Eric Isham
Yeah.

[00:13:08.780] - John S. Berry
Where it's just like,

[00:13:09.700] - Eric Isham
very cool.

[00:13:10.320] - John S. Berry
I'm here, I get to run my own show. 'Cause as you know, as you move up the ranks, the less authority you have, right?

[00:13:14.720] - Eric Isham
Yeah, sure.

[00:13:15.420] - John S. Berry
But as I was kind of, we had our own operation. I loved having a full-time staff, even though I was, you know, one weekend a month. I had a full-time staff running everything. And that really taught me a lot. I'm like, wait a minute, I can do this in the business. We could have remote team members. I don't need to be in the office every day. I don't need to be the first in, last out. Like if I hire great people, I can start to build this. So this was back in 2000, about 2016. I realized like I was gonna retire the next year. So I really started to get, serious about growing the firm.

[00:13:46.680] - Eric Isham
Okay.

[00:13:46.700] - John S. Berry
And that's when the first domino fell. I hired a guy to be my general counsel. He was from the oldest firm in the state of Nebraska, former Marine infantry guy who went JAG, well-respected. He was kind of known as a fixer, and I hired him as our general counsel. So his job was to solve all of the firm's problems. I didn't have to solve those anymore.

[00:14:07.820] - Eric Isham
Okay.

[00:14:08.380] - John S. Berry
Then I got him and then I got another great litigator. And then I got a guy who was a former G6 for the Nebraska National Guard to run our IT, and I just started building from there.

[00:14:17.750] - Eric Isham
So I want to go back. You, you said something that kind of struck a chord for me. You said, I, I realized I didn't have to be the first in, last out. I think a lot of entrepreneurs, we all feel that way because, you know, when you start a business, you're the only person there, so you're obviously gonna be the first in and the last out. Uh, but I think a lot of us carry that with us for a long time, right? You, you comes from, you know, being in the military, right? You want to show by example, you want to lead by example. If you're asking the Joes to do something, you want to show them that you're going to do it too. But then you said something else, that I was going to retire the next year. So how old were you when you were making this statement that you wanted to retire?

[00:14:54.870] - John S. Berry
I'll retire from the Guard.

[00:14:55.670] - Eric Isham
From— okay, from the Guard.

[00:14:56.650] - John S. Berry
I had my 20 years in at that point.

[00:14:58.210] - Eric Isham
You did 20?

[00:14:59.110] - John S. Berry
Yeah.

[00:14:59.590] - Eric Isham
Okay. Wow. Okay. So you did your, your full 20. So you did some stuff on the active duty side. Most of it was Guard,

[00:15:04.430] - John S. Berry
right

[00:15:04.950] - Eric Isham
In Nebraska. Okay, cool. And so you're retiring from the Guard and then you're going to be full-time in the business and you made a decision, hey, we're going to grow this,

[00:15:12.870] - John S. Berry
right

[00:15:13.010] - Eric Isham
I'm going to run this like a business, not as an attorney practicing at the company.

[00:15:17.250] - John S. Berry
Right. But there's a big gap between making that decision and actually getting there.

[00:15:20.090] - Eric Isham
Yeah, sure. There always is.

[00:15:21.450] - John S. Berry
Yeah.

[00:15:21.970] - Eric Isham
Yeah, there always is. So you hire this guy, he comes in, and then how quickly do you start seeing things happen there where he's solving the problems and you're not?

[00:15:31.840] - John S. Berry
It wasn't quick. It was slow, but it was a necessary change. And so we started to build the practice around quality, right? It was all of a sudden, it was, hey, some of the people that were here right now, they're not good enough anymore. And why? Because they're causing the problems. And it was crazy. We were losing money on insurance. This is a service business, right? Think about it, a service business. And we're losing money. And, and it's not like we have a factory and we got a bunch of widgets, and we've got a bunch of inventory over here. No, it's like these are people and they're not producing.

[00:16:05.320] - Eric Isham
Yeah, well, attorneys are expensive, so I could see that if you got them on payroll.

[00:16:08.280] - John S. Berry
Yeah. And look, they all have families, they have, you know, and then some were very loyal and some were friends. Some had worked with my dad for a long time, but they were not producing. And at the end of the day, it didn't help the clients, it didn't help the firm, right? And so, you have to make those tough decisions. They've been around a long time, but if you're committed to growing a great organization, and I think growth can't just be in size, it has to be in ability and growing the quality of your services. And so I had to make those tough calls.

[00:16:38.000] - Eric Isham
So, let's, let's talk a little bit about mission now. So, so we're 2016, 2017, we're, you've, you've, you're charting a new course. Um, you're starting to put your, uh, rating people to make sure that the right person, right seat. When did you start seeing results from that effort? And it's tough, right? It's— it's a— that's a hard thing to go through. But when you get on the other side, how long did it take for you to start to see those results and you start to grow the organization?

[00:17:03.290] - John S. Berry
Yeah, I mean, it was— I mean, we moved at a glacial pace, right? Progress happens slow. It's— it's like loading a spring. And so, it just took so much effort. And then maybe 2020.

[00:17:17.770] - Eric Isham
Okay,

[00:17:18.370] - John S. Berry
then boom. You know, and then it launched.

[00:17:27.720] - John S. Berry
Thank you for joining us today on Veteran Led, where we seek to help Veterans build an even bigger, better future after military service. Unfortunately, for some of our Veterans, the roadblock to a better future is that they are not receiving all of the benefits that they earned. If you need help appealing a VA disability decision, contact Berry Law.