In this episode of Veteran Led, John S. Berry reflects on his journey as a podcast host, sharing lessons learned from early failures, memorable guests, and the challenges of staying authentic.​ His conversation with Donny O’Malley taught him the power of authenticity, while General Petraeus demonstrated how single leadership lessons can expand into deeper insights. Berry admits his initial assumption that courtroom skills would translate to podcasting was wrong, leading him to seek professional coaching.​ Looking ahead, Berry remains committed to providing value to leaders until, in his words, “my lessons are no longer relevant.”​ Veteran Led is now available on Amazon (https://a.co/d/gcBgpnO) or contact John directly at John.Berry@BerryLaw.com for a signed copy.
You can say, well, that must be what excellence looks like because look at this great podcast. And then you start doing it and you realize, greatness is so much further than you think it is. You think, oh, this is a podcast. You get on there, you talk, someone records it, you’re just hanging out. It’s fun. It’s cool. No.
Welcome to Veteran Led. Once again, Brandon Aksamit stepping in as guest host for John Berry, CEO of Berry Law and author of Veteran Led and your normal host, of the Veteran Led podcast. John, we’re going to talk about something that was your idea, behind the scenes of producing and hosting a podcast. I can only imagine how excited you are to dive into this one.
This was one of my great failures early on. Failure upon failure. So, the book was actually way behind schedule, and I had all the content. I’m like, what do I do with this? And then I saw that somebody had a book, and they were just reading chapters in the podcast. I’m like, oh, I’ll just take little pieces of this and start doing a podcast. And then we got it, and that didn’t go well. We worked with the company that the first seven episodes, they told us afterwards, Yeah, these didn’t record right. You’re going to have to redo them. So now I wasted all this time preparing, and I didn’t even know how to prepare. So, they were pretty bad. But we had to reshoot them. So, taking garbage and redoing it is bad. And then we started having guests, and I had some phenomenal guests, but I really didn’t know how to ask the questions. I thought, Oh, because I’m a lawyer and I can ask questions in court, this is no problem. But truth was that I had no idea what I was doing and the types of questions I may ask a witness on the stand, especially when I’m cross-examining them and asking leading questions, doesn’t work so well in the podcast.
So, I got some coaching, and I still suck. But the thing is, I’ve stuck with it for now almost 100 episodes. We’re coming up on 100 episodes. The book is now published, and it was a great journey. I think it’s important to do things that you’re not good at.
And we are going to jump into the coaching process and what you learned. But before we get there, we glossed over the fact that, oh, I just did a podcast. It was about 100 episodes, and here we are without any previous experience. That speaks to your personality, but what led you to say, you know what? I’m going to jump right in. We’re going to do 100 podcasts, and it’s going to be a journey. How did you get to that point?
So, my father, who was a famous trial lawyer, was also a paid radio show host from 4:00 to 6:00 PM on Drive Time. So, most lawyers would pay a million dollars a year. They were paying my dad to do this back in the ’90s. And so, I thought, well, if my dad can be in court all day and then show up from 4:00 to 6:00 and do a radio show for 2 hours, why wouldn’t I be able to knock out some 30-minute podcast? I mean, it can’t be that hard. It turns out it was pretty hard, and my dad was a natural. And of course, that was just something that he did really well. But it was one of those things where I realized I will never be as good of a trial lawyer as my father, and I will never be as good of a radio host as he was.
Well, I think you’ve got to cut yourself a little bit of slack because you weren’t only doing the audio, but you’re producing video as well, which is an entire another layer of producing when you talk about podcasting. So, what did you take away from understanding, Hey, I’m on camera, and we’re going to have this video element to the podcast in addition to the audio?
One of my great mentors, Army Veteran Harlan Schillinger always said, and then this was when I’d have a trial or something, and the media would be there. He said, When you look at the camera, make sure that you talk to the camera like it’s a jury. And I said, Okay, so what does that mean? He says, Well, be personable. But who are you? And I said, Well, I like to be clear and concise. He says, Then be clear and concise. And later, as I began to look at other… I had some public speaking opportunities. I wanted to not screw those up. So, I started studying it, and I found that clear and concise is much better than cute and clever. And the reason why is because cute and clever, people get confused. They don’t know what you’re talking about. But if you could have a clear message, then it’s just going to resonate with more people, and it’s easier to stay on track.
You referenced the early stages of Veteran Led, the podcast where you were doing solo episodes prior to getting into guest interviews, and there’s a different style that goes into that. Let’s talk about those solo episodes. What did you learn in those early days that you referenced, weren’t maybe the best, but you still were knocking them out anyway.
So, they started off as just rants and then I tried to put it on a whiteboard, and we had a teleprompter because we shoot a lot of video and commercials. And I’m like, why are we not using the teleprompter? And then the key was to learn how to use the teleprompter for notes because you don’t want to look like you’re just reading something. You have to be spontaneous. But it was nice to have those notes and to be able to go through and not get to a point where, oh, I lost my place. What am I talking about? So, learning how to use a teleprompter to have notes or just to have those notes. And if you want to be really concise and there’s a very specific point, then you do want to use that teleprompter and use it and say the thing that you need to say verbatim so that it comes out right. But that took a lot. And then it just took a lot of practice, rehearsal. And that’s just like the military. We rehearse It’s everything that we do. And the more rehearsals, the better you get. And so, the big takeaway was, I already knew I needed to rehearse, but for some reason I thought I didn’t need to rehearse.
I just assumed these guys that do podcasts, and some of them are so bad, it’s probably true, but then you show up and you talk and that’s it. And no, it takes real talent to do that. And I didn’t have that talent.
Well, I think some people and your viewers who’ve been with you from episode one to 100, they’d be lying if they didn’t see progress. We talked about the transitions where you went from the solo episode to then interviewing guests after you got through the chapters, and that’s an entirely different skillset. What was that development like as you transitioned to not only just talking and ranting, as you put it, but talking to somebody and having a conversation that’s meaningful?
It’s tough because there’s a tendency to either overprepare or underprepare. So, when I had guests that I had known, it was fairly easy. But when I had guests that I didn’t know, I’d prepare. And it’s amazing. We could start off with a LinkedIn profile, go to Wikipedia, and then you’d find out half the information was wrong. And of course, I looked at my LinkedIn profile, I’m like, Wait a minute, half my stuff’s wrong. So, you learn the hard way that you want to verify all that information upfront, that you want to put your guests at ease. I just assumed that because some of these people had been on several podcasts, that they would just come in and hit it out of the park. That wasn’t always true. And so, I had to put them at ease. It’s very similar to when I sit down with a client. Even if that client is a lawyer, I’ll say, Look, everything you tell me is attorney-client privileged, which means I could not tell anybody else, even if I wanted to, and I don’t I want to, because I would lose my license. And it seems to put them at ease.
And so, it’s one of those things, too, where we start the podcast, we say, Hey, look, this is not live. This is being recorded. We can stop at any point. We can edit this thing. If there’s anything you want to go back and change, we can do that. That usually puts them more at ease.
Take us through the film review sessions. Former college football player, you know about reviewing film, and that’s how you get better. And I know that that’s been a part of your process.
I was mostly on the bench in college, but I did have to watch a lot of film.
So, then you’re right at home for the podcast. You would record the podcast; you review each episode. Painful, enjoyable, what has that been like as you would go back and watch yourself knowing this maybe isn’t what I want to do, or this isn’t where I feel I should be?
Years ago, I’m in the middle of this federal trial, and we’re back in chambers. The judge has us back in chambers, and we’re listening to something from the audio. I can’t remember why we’re doing this, but for some reason, we’re listening to part of the trial. You have a court reporter, but I think maybe there’s a question about whether somebody said something, so we’re listening to it. The judge just looks at me and he’s like, I know what you’re thinking. You’re thinking about how bad you sound right now. I’m like, How did you know, Judge? He’s like, The first time… He’s like, Actually, the first several times I heard myself speak in court, I wanted to put a gun in my mouth it sounded so bad. I thought, that’s pretty extreme, but it is like, Oh, I sound terrible. I hate my voice. I hate the way I look. I hate what I’m saying. And then you get over that and you get more objective. And then you say, Oh, I am slurring my words. I need to pause more. I should have paused here. As you go back, and you can be self-critical, it becomes easier.
But initially, it’s just so painful to watch and to listen. And you’re like, Oh, this is horrible. But after that initial pain, after you take the pain, it becomes easier to listen and to be a little bit more critical of yourself. And you just have to disconnect a little bit because it’s really easy to watch somebody else and talk about everything they screwed up. But when you’re screwing it up, you’re like, man, I’m worse than I thought. The reality is this. You’re never as good as you think or as bad as you think.
There came a point where you said, Let’s bring in a coach. We understand that you look at feedback as a gift. You’re able to put your ego aside. But when was that decision? How did you get to it?
I know I made that decision in several aspects of my life. I had a speaking engagement coming up, and it was really important for me to do well. I had tons of public speaking engagements, several speeches a year. I talked in front at legal conferences in other places. No big deal, right? But I was a member of EO, an entrepreneur’s organization. I heard this woman speak, and her speech didn’t resonate with me at all. But I was watching how masterfully she spoke, and the mechanics were just amazing. She’s doing all these things herself. This is all planned. So, I said, I need to learn this. And then as I thought about that, and so I signed up for the speaking program, then I’m like, well, my podcast kind of sucks, too. I’m like, I need to learn this. So, I need somebody else to teach me this. And so there are things that cross over, once again, knowing when to pause, the tempo of your speech, whether you’re going to raise your voice, lower your voice. All those things matter. But it’s different in a podcast. It’s much different, especially when you have a guest. So, I wanted to learn both skills.
I think that at the time, I thought, I’m great. I think I’m great teaching because instructing in the military is one of the things I did when I was the officer, warrant officer, school commander. I had to murder board some of the instructors to make sure that they met the standards. So, I was very comfortable doing that. And I love teaching, and I love interacting with students. And I love being in the courtroom and trying cases. But public speaking is different. Podcasting is different. And those are different skills. And I had to learn those skills. And once again, I’m still learning. I think I was probably, when I started the podcasting, probably a solid four. I’m probably a five and a half right now. I mean, I’m getting there, but it’s about improvement. It’s about getting better, and it’s about giving the audience what they want.
And so, you get that feedback, and then you know what you need to do, and then you get your next rep, and you’re trying to implement the feedback that you’ve received. How has that process gone? And how do you manage the emotions of, I’m trying to do it, it’s still not clicking, and then knowing that there might be that glass ceiling that you will break through eventually.
So, it’s one thing I learned when I did bodybuilding for a while. I played sports my whole life. In my early 30s, I learned that and before, it was just throwing up as much weight as you could. Then it’s like, you know what? It’s not about the number of reps you do. It’s about the number of perfect reps that you do. For me, it’s not just getting the reps. It’s doing it right. Practice doesn’t make perfect. Perfect practice makes perfect. And I believe it was Bruce Lee who said, You don’t do something until you can do it right. You do it till you can’t do it wrong. So, if that’s the case, then I’ve got a long ways to go. But I also know that mastery takes 10 years or 10,000 hours. So, 10,000 hours, I don’t know, maybe when I’m 90, I’ll master this. But yeah, it’s going to take a while.
Any specific piece of advice you’ve received thus far that has stuck out to you the most or you found most beneficial going through this process?
Be yourself. I think when I listen, I’m robotic, and sometimes my voice is very staccato, but sometimes that’s planned. But at the end of the day, people are going to like you or they’re not going to like you. You’re going to provide value to some people and not other people. Everybody’s going to have their opinions, right? But it’s the opinions of the people that you want to be a hero to. It’s the opinions of the people that matter to you that you need to pay attention to. A lot of people aren’t going to like you. And in fact, once you start getting haters and people start saying negative stuff about you, you’ve won. Now you’re so important that people will say bad things about you. That’s when you know you’ve made it. And so, I think that all feedback is good feedback. Now, it’s not all weighed equally. Feedback from the people, from the high performers, right? If you had feedback from a Joe Rogan or somebody, that would be worth more than some troll online who says they don’t like what you said, or I misused a verb or a pronoun or a noun, or I said something in a way that was not grammatically correct. So what?
So, we’re talking about the specific individual coaching, and you did hit on earlier what goes into producing a podcast? And it’s been a long and winding road for you, and I think you eventually ended up doing it in-house. What were some of the biggest lessons you learned going through those vendors and the processes that go into having a successful podcast and being a part of a team that’s invested in what you’re doing?
I think the vendors that can get you launched aren’t going to be the vendors to get you to the next level. Just as you improve, that team needs to improve. So going back, our initial vendor was, it just wasn’t working out. And I can remember there was a big podcast conference in Denver, and my assistant, Betsy, was there, and it’s like five o’clock on Friday. I’m like, Well, where is this guy? Because I want to talk to the CEO of the company. Now, I always think that when I work with other organizations, and we’re only a little over 130 people, but if it’s the same size as me, I want to have a relationship with that CEO. I’ll send them my vivid vision, which is my vision statement. I’ll send them our brand guide. Hey, I want to I want to be your best client. I want to be your best customer. So, we get there, and we get rolling and everything’s falling apart. The person managing our podcast, we’re just not impressed with. And so, I say, Betsy, I want to talk to the CEO. She’s like, well, I just talked to his assistant, and he’s gone.
Well, where is he? Well, he’s going to the podcast conference in Denver. I said, all right. When’s the next plane to Denver? She’s like, seven o’clock. It’s five o’clock. I’m like, okay, Betsy, you’re going to Denver. Find him, set the appointment, and then go talk to three other vendors. Figure this out. She comes back and she made some connections. Then she figured out how we could start doing some of this stuff in-house, and we started working together to build the podcast. We hired Trevor, our videographer, and he learned some audio pieces. Then we had a guy on our IT team that played in a band that also understood how to improve our audio. And so, it’s just been a constant improvement. It’s very much like in the military; we always are improving our fighting position. So, yeah, the vendor you start with probably won’t be the one that gets you where you need to be, but you need to start somewhere. And start without a vendor, but you need to start. And so, Betsy, Trevor, my team, now we do it all in-house, and it’s been a great experience. We’ve worked with some other great vendors that we’ve worked in their studios, and that’s been fun, too.
But right now, we’re doing it in-house, and we’re having a blast. So, for us, it’s working. And once again, data matters, right? If you ask, is this a successful podcast? The question you should be asking yourself is, why am I doing this? What do I want to get out of this? How many subscribers do you want? Whether that’s on a podcast channel or YouTube. And then what do you want those subscribers to do? And you have to be really intentional about that because that’s how you’re going to measure whether it’s successful or not, whether it’s worth doing 100 episodes or 200 episodes or do for five years.
Time for our After Action Review. This may be a tough one because you’ve had a lot of high-profile guests. General Petraeus comes in front of mind, and you’ve done over 100 or nearing 100, rather. But do you have a specific favorite episode? And if so, why?
My favorite is Danny Maher, Donny O’Malley. The authenticity was just amazing. It was one of those things where after the podcast, I’m like, I suck. This guy is so authentic to who is. He knows who he is. And that was the real gift I got from doing that podcast. And the energy was great. The interaction was great. He was phenomenal. But I really took away something from that, which was I need to be more authentic, more true to myself. And I don’t think I have the guts to be who he is, but I need to be who I am.
Well, that went into my next question, too. The most meaningful lesson you learned from one of your guests. So, if that was number one, do you have a second or third that you also took away from these podcast episodes?
Well, I mean, General Petraeus, there are all these leadership lessons that I had learned from either when I was in the military, I heard about them, or I read the book, All In. And so, he answered the questions, and he answered them in a way that I thought I was going to get this concise answer that is going to just answer my question. But he was just going through layers and layers and layers of knowledge. It just blew my mind. And I was like, wow, what a phenomenal leader. And the way he could articulate, take one lesson and blow it up to all these important other lessons that I hadn’t even thought of. It was mind-blowing. It was a great experience.
As we’re nearing the century mark for Veteran Led and reflecting on those first 100 episodes, what would have you done differently?
If I could go back in time, I would have hired a coach right away. I would have done a better job of planning the episodes. I would have prepared more. I would have sought out mentors. I would have built this studio sooner. Everything that I did, I would have done better. But I didn’t know at the time, you don’t know what excellence looks like when you’re starting off. You can say, Well, that must be what excellence looks like because look at this great podcast. And then you start doing it and you realize it like it’s kind of like you’re climbing a mountain, and you think this is the summit, right? Oh, it’s not that far. And it’s a false summit. Greatness is so much further than you think it is. You think, oh, this is a podcast. You get on there, you talk, someone records it, you’re just hanging out. It’s fun. It’s cool. No, it’s actually pretty tough.
Lastly, what’s next for Veteran Led? You’ve got to the 100 mark. You seem to be having fun. You’re making improvements. How many more episodes can people expect?
Until I get bored. Look, the book is out, which is the whole reason for the podcast. And now that it’s out there, so long as I can continue to help leaders and provide value, I’ll continue to do it. But there may become a point where you jump the shark, just like in TV, where Fonzie jumps the shark in Happy Days, and that’s the end. It’s like, okay, these episodes are all downhill now. I don’t know if the podcast will ever get there because things change so much, but it may get to the point where I am no longer relevant. My lessons are no longer relevant. People don’t want to listen, and the people will tell you what they want. But once I’m no longer providing value, the public will let me know, they’ll tune out, and this will die.
Thank you for joining us today on Veteran Led, where we pursue our mission of promoting Veteran leadership in business, strengthening the Veteran community, and getting Veterans all of the benefits that they earn. If you know a leader who should be on the Veteran Led podcast, report to our online community by searching @VeteranLed on your favorite social channels and posting in the comments.
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