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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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[00:00:00.590] - Rob Stewart
In the military, we have this saying: it's better to go down and around than up and out. Meaning you take care of the people that are to your left and right and below you because they look up to you. And when they lose confidence in you, the entire process is affected by that.
[00:00:17.880] - John S. Berry
Welcome to Veteran Led. Today's guest is Rob Stewart, Air Force Veteran. How you doing today, Rob?
[00:00:22.720] - Rob Stewart
Great, John, thanks.
[00:00:24.260] - John S. Berry
So let's start with what you do, the name of your company, and then we'll talk about how you got there.
[00:00:29.360] - Rob Stewart
Sure.
[00:00:29.700] - John S. Berry
No, actually, f*** I think I want to tackle when you went out to get a loan, you couldn't even get a peanut butter and jelly sandwich. I like that. Let's start there.
[00:00:39.000] - Rob Stewart
The biggest thing when you get out of active service or leaving a job, right? You have an idea, you want to do a business. People look at businesses like hobbies. They think that if you're not producing revenue, if you haven't been in business 2 to 3 years, you don't have brick and mortar somewhere or purchase orders that are outstanding. They really don't have anything to do with you, right? It doesn't really matter what you've done in uniform or what you've done to this country. At the end of the day, it's just dollars and cents. And what I found as a challenge is going into a bank or any type of institution, it's like, hey, you're a number. How long you been in business? What's your revenue like? And they're like, okay, well, when you're in business for a year, 2 years, have a couple of tax returns, they've got some purchase orders. Come back to us and we'll give you a loan. It's like, if I had that, I wouldn't be here. Right. And that was really kind of the chicken and the egg situation when we first started. It was one of those things where it's like you're either going to experience a lot of pain and bootstrap this, or you're going to have to get a venture capital investor or really just, you know, never realize your dream.
[00:01:44.770] - Rob Stewart
It was a huge kind of like opportunity for us in the beginning.
[00:01:47.860] - John S. Berry
The opportunity was you couldn't get a loan.
[00:01:50.380] - Rob Stewart
Yeah, I mean, it was terrible. I mean, one of the things that was struggling is like, and what was really frustrating, John, is that the people sitting on the other side of the bench, I went to several different banks, banks that I've had relationships with my entire life, right? Before military, throughout. One of them had an account for over 20 years, right? And they would tell me, man, this is a great idea. Wow, this is going to be a Fortune 100 company one day. And you'd hear these things. So you remain really dedicated to what you were doing, but at the end of the day, they didn't move the needle. So I saw an opportunity and I was like, all right, there has to be a way to utilize technology for us to paint a picture of this individual and this concept and this idea in order for them to get past that barrier of entry and at least get some seed capital to realize their dream. And that's when we started CR Equity AI. Basically, we utilize artificial intelligence to remove implicit bias out of a system where a client comes in almost like TurboTax. They fill out a very simple questionnaire, they upload 2 or 3 pieces of relevant documentation, and then on the back end of that, we have lending services agreement with well over 30 to 40 private equity, private money lenders that are willing to take that inherent risk outside of the brick and mortar of normal institutions to provide someone liquid capital to realize their dream.
[00:03:12.910] - John S. Berry
Yeah. And let me break this down into simple, if it were in terms, you went to get a loan, you couldn't get a peanut butter and jelly sandwich. They wouldn't give you anything. And so you built a company, a real AI company.
[00:03:22.750] - Rob Stewart
A real company.
[00:03:23.390] - John S. Berry
People say, oh, it's AI. No, this is an AI company that assists in removing some of the biases that are out there that help Veterans or anyone else get loans from banks. You simplify the process using AI systems.
[00:03:38.070] - Rob Stewart
That's correct. So between 2024 and 2025, We went from being a small kid that nobody knows to doing just over 180 loans, both business and real estate. I did that with a team. At the time, we only had 9 people. Now we have 17. That's about $87 million of total money out of the door, both equity and debt. We did that pretty much virtually. We're a non-traditional lending institution. We started off really underwriting for family offices and institutions. And then because we were able to take what we did and provide unparalleled visibility into things that some of these institutions never thought about before with our underwriting capability, one of our family offices said, hey, we really like this and we want to give you a line of credit internally. We want you to just expand on this. And as your needs grow, come back to us with various different reporting mechanisms and we'll look to expand it. So fast forward today, John, as God has blessed us, we have a $250 million direct line of credit internally. What we have done is we've changed our model a little bit. We built our own large language model.
[00:04:55.170] - Rob Stewart
We got rid of the barrier of entry. So I don't know if you and your wife or you and your spouse or you and your significant other on your phone every month, you probably get a recurring charge for some type of subscription. Pick something, right? Disney Plus or DocuSign or whatever, right? I went out to Silicon Valley about a year and a half ago and I was there and I was kind of starstruck with all the types of AI and tech companies that were coming up. But one of the undercurrent things that I saw was, and most recently it came out, subscription as a service model is dying. People are tired of paying for stuff and not getting value for it. Right? So kind of like in the military where you have to bet on yourself, I redesigned our platform to be value first. Right? So when you come onto our platform, you access 100% free. You get to submit all your documentation. You'll get a term sheet. And if you like it, if that's something that you can live with and you say, you know what, these terms make sense for me, you accept it.
[00:05:56.530] - Rob Stewart
You pay a small nominal application fee, really just covers the cost of cloud services and the AI assistant that's dedicated to your file. If it's a real estate transaction, you have to pay for your due diligence cost, which is like your appraisal. And then from there it goes into an API and through our workflow, you'll get a loan decision within an hour or two. You sign off on it, you give us your wire instructions, and the funds are transferred the same day or next day.
[00:06:20.860] - John S. Berry
Wow. And so let's take that to the leadership level. This, the after-action review, your examples of great leadership and poor leadership, whether it's in the Air Force or whether it has been in the private sector.
[00:06:33.520] - Rob Stewart
Yeah. So one of the things I'll tell you is that I am a servant leader myself, and I'm very protective of my team. And I'll give you an example that just recently happened, like within the last 2 weeks. I had a gentleman that I have trusted for a long time and was our basically product team leader, had been with the company since its early stages. Really was kind of the glue and the anchor to really bringing things together. We had a lot of strife in the beginning. I know as an officer, you know, you have like the storming, norming, then performing type thing, right?
[00:07:10.220] - John S. Berry
Right. Oh yeah.
[00:07:10.720] - Rob Stewart
Remember that? Remember that? Yeah. With Bollig and stuff like that. And we had a lot of that going on as with any type of forming of a team. And he was really kind of the continuity of operations there. But then his work product started to suffer. Things as the platform started really mature and we were starting demanding a little bit more from this area, this area, instead of us actually growing and moving into these brand new capabilities, productivity started to suffer. But we had added additional resources of people. Like people think with an AI company, man, all you're just concentrating on is tech. That's not true. You have to have the human interaction. You have to have the people to build the systems, right? Hold the systems accountable, fix the systems when they break, and then more importantly, scale the systems. And the only people that can do that are humans, right? At least now. The problem is he was really relying on tools and thought we had gotten to a point of almost complacency. And you know, John, by being in active duty, it's like when you start taking effective fire, You can't stay in one position.
[00:08:20.330] - Rob Stewart
You have to advance the contact. It's the same thing what we do, which is you have to remain innovative. Companies die when either they run out of cash, they get complacent, or they stay there and they take effective fire, don't move. Jeff Bezos said it most prudently probably about a year ago, and I was shocked when he said it. He says, look, I know in my lifetime that Amazon is either going to get blown out, bought out, or go bankrupt. Something better is going to come along. Amazon, right? I mean, it's, you know, I mean, just think about it, right? And what they told me was that we are not JPMorgan Chase. We are not your traditional money, you know, lender or whatever, right? The only way we survive is being innovative. And my team depends on leadership. They feed off of me. If I have a bad week, our productivity sucks. I can show you the data, right? So with this individual, poor leadership, I found out, and his team did not want to like rat him out like that. You know, people don't want to come to the old man or old woman and say, hey, this guy is not doing it.
[00:09:25.850] - Rob Stewart
But what I saw was I saw productivity lagging. So I pulled each one of them aside and I said, hey, what's going on? And they would say, oh, Rob, everything, everything's good, sir. And I'm like, what's really going on? And they said, well, we sent, you know, this work to the team lead, you know, 2 weeks ago, 3 weeks ago, and I'm still not getting feedback. I don't want to move forward with this, sir, without, you know, clearance on that. So I pulled him to the side and I say, hey man, you know, what's really going on? And John, you know this by being a company commander, it's like you have good people and sometimes there are third party essential things that are going on that impact the mission. Now, as a leader and someone who has a successful company, it can't always be about the bottom line. You can't just blow everybody out. For, you know, the first sign of issues, right? You had to get to the root of the problem. Maybe it's a thing at home, maybe it's a financial thing, we don't know, right? So I did take the time and I just found out that this individual was working multiple jobs outside of his primary responsibility because he had felt that we had gotten to a point where he can kind of go on autopilot and let everybody else do everything, but he still wasn't taking care of home.
[00:10:42.110] - Rob Stewart
And what I explained to him is like, in the military, we have this saying, it's better to go down and around than up and out. Meaning you take care of the people that are to your left and right and below you because they look up to you. And when they lose confidence in you, the entire process is affected by that. And I showed him that. I said, look, these people have lost confidence in you. And as a result, here's the outstanding instances in Jira and our development that have been suffered because of that, all because of You decide you don't want to be here. You've got other things that are more important. Unfortunately, we had to let go of that individual. And immediately, like literally within 48 hours of getting rid of that individual, productivity not only went back to where it was, it was like taking the handcuffs off people. And like, we've resolved more instances of JIRA in our backlog than we have in 8 months, John. And as a leader, that hurt me because it's one of those things, why didn't I see that? Why was I not able to actually come to that realization earlier?
[00:11:49.580] - Rob Stewart
And it's one of those things where I need to look internally and say, okay, these are the signs as a leader. If I really want to take this to a Fortune 100 company, I've got to be able to spot this earlier on. So it wasn't just getting rid of the middle, you know, the middle management, if you will, middle team, right? It really was a reflection on me because at the end of the day, your company is an extension of who you are as a person. It's not just a, you know, hey, let's go out here and make a bunch of money. It's like, are we doing the right things? Are we following through? The people we're hiring, are they up and down and around taking care of the people below them? And I made that hiring decision, right? And that is a reflection on me. So good leadership to me, is as much of what we're talking about in front of each other, but also looking internally, because a failure is as much the person at the top of it as it is the person that's committing the offense. And good leaders know that.
[00:12:43.530] - Rob Stewart
And if you don't, it's very easy to say, you know what, that guy's a shitty individual.
[00:12:48.010] - John S. Berry
Right. But you're tolerating it.
[00:12:50.990] - Rob Stewart
Exactly. You're complicit. Right. And if you're doing that, there's a second or third order cost to that., and you have to look internally and say, you know what, we missed the mark on them, but the next one we're going to hit out of the park. So you got to hold yourself accountable as a leader.
[00:13:05.120] - John S. Berry
Outstanding. Rob, where can Veterans learn more about you personally and your company?
[00:13:09.560] - Rob Stewart
Yeah, absolutely. So the company is www.charlieromeoequity.ai. So CR equity AI is our website. We're also on YouTube and LinkedIn. And I will just tell you, John, any person that contacts me directly, rob@crequity.ai, mentions that they came through the podcast, we're going to take care of them and give them a Veteran promotion. So one of the things that I'm huge on, right, is taking care of our folks to left and right. And as a part of that, we're going to give them a discount on any type of product that they come on and come on the platform. And I'll personally do it myself, right? I want to just give back. Because it's hard out there, man. And everyone that's listening to this is not looking for a handout. They're just looking for a leg up. And that's different. An opportunity is different than a handout. And we want to make sure we facilitate that as best we can.
[00:14:05.730] - John S. Berry
Yeah. I think the Veteran community out there, like, everybody struggles, right? They do. The difference is we're more resilient. And sometimes the toughest thing to do as a Veteran is to ask because we are more resilient. But if you hadn't asked and asked and faced the rejection, you wouldn't be able to solve this problem for you and for everyone else. So the fact that you have found a better way to get loans, to interact with banks, because we hear it all the time. Oh, yeah, you're a Veteran. You get out, you're going to be taken care of. And no, you have to take the initiative. Nothing is given to you.
[00:14:35.420] - Rob Stewart
You got to bet on yourself.
[00:14:36.620] - John S. Berry
You have to bet on yourself.
[00:14:37.880] - Rob Stewart
Yes, sir. Absolutely. Absolutely. And that's what— I mean, everybody that owns a business that wore a uniform, it's just like negotiating basic training or the pugil stick or the crucible or some challenge. That, you know, defined if you were going to be what type of leader you're going to be, right? Owning a business is that instance, but it's every day, you know, it's engaging with people across from you that may not like you or don't understand your business, but, you know, figuring out that problem and getting to the end and bringing everybody home.
[00:15:05.900] - John S. Berry
Outstanding.
[00:15:06.780] - Rob Stewart
Yes, sir.
[00:15:07.360] - John S. Berry
All right. Anything else you want to add?
[00:15:10.200] - Rob Stewart
Uh, John, I just want to tell you, you're doing the Lord's work, man. Uh, Berry Law, I have family members that actually were clients, uh, years ago, uh, my cousin Just to give you a little soundbite and plug you. I know he went through, he went through a significant amount of time to try to get benefits. And I think he got with one of the associates within the firm a couple of years ago and after 4 or 5 years finally got the benefits in which he earned. So, you know, seeing you over here really kind of gave me flashbacks in a good way. Right. And so, I just want to say thank you for everything you guys are doing for Veterans on the legal side. Cause that, that is just a, That's a minefield for a lot of people, man.
[00:15:47.660] - John S. Berry
Thank you, and thank you for everything you do.
[00:15:54.010] - 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.