199: Frontlines of Freedom with Lt Col Denny Gillem
7 Dec 2025 · 22 min
Podcast episode 199 of the Heroic Investing Show featuring Lt. Col. (Ret.) Denny Gillem. Hosts Gary Pinkerton (with Jason Hartman co-hosting) interview Gillem about threats to American civic life (political polarization, name-calling, erosion of shared values), national-defense concerns (China, Russia influence in Venezuela, importance of checks-and-balances), and his long military career (West Point grad, infantry/Ranger, 22 years active duty, multiple valor awards). They also discuss Gillem's radio program Front Lines of Freedom (on ~180+ stations, approaching its 600th episode) and his memoir The Smiling Life and Career of an Army Ranger.
Questions this episode answers
Episode 199.
frontlinesofreedom.com.
22 years.
About 180+ stations.
About the 600th episode.
Chapters
Welcome to the Heroic Investing Show. As first responders, we risk our lives every day. Our financial security is under attack, our pensions are in a state of emergency. A single on duty incident can alter or erase our earning potential instantly and forever. We are the heroes of society. We are self reliant and we need to take care of our own financial future. The Heroic Investing show is our toolkit of business and investing tactics on our mission to financial freedom.
Welcome to the Heroic Investing Show, a podcast for first responders, members of the military, veterans and anyone looking to improve their financial future and gain some freedom with their time. We teach America's heroes how how to build passive income, build their startup business and safely grow wealth through real estate and other alternative investments. We help current and prior first responders put protections, systems and a team in place to help them build a life where they can focus on their passion, that service or product that they are uniquely gifted to share with others, making the world a better place for all of us. My name is Gary Pinkerton and I co host this show with Jason Hartman. This is episode 199. My guest for today is Lieutenant Colonel US army retired Denny Gillam. Denny is the host of Front Lines of Freedom. It's a military news and talk radio show that has been airing for over 11 years now. Denny is a graduate of west point, graduated in 1964 and was commissioned in the infantry. Denny served in Vietnam as a member of 1st Infantry Division. He, he was a member of 101st Airborne Division, also did time in Vietnam with that and he was army advisor at the Michigan Army National Guard. Denny is an awardee of the Silver Star for Valor, Distinguished Flying Cross, Soldier's Medal, Bronze Stars, two Purple Hearts and many Army Commendation Medals. He is a patriot, a really awesome host of an important show that digs into subjects of patriotism, trends and problems that are occurring in this great nation of ours. Please welcome Lieutenant Colonel Denny Gillum. Well, heroic investors, welcome back and thanks again for joining us. You're going to love this interview today. It's with Denny Gillum. Denny, I'm sad to say, did not graduate from the Naval Academy, but he did the next best thing. He graduated from West Point and I had to get that in at the beginning before I forgot. We won't talk about. We are in fact banned. It's part of the contract. Denny, we're not allowed to talk about Army, Navy, at least for another couple years. So jokes aside, thank you sir, so much for joining us here on Heroic Investing.
Hey, I'm glad to and by the way, I root for Navy every game they play except one, when they play army. And I root for Air Force, every guy they may play except when they play two, army or Navy.
So yeah, it's such a wonderful.
We can pick on each other.
That's good. Spirited.
We can pick on each other and we do. Yeah, but we're brothers.
That's right. So you were commenting, how many years ago did you finish up there at West Point?
55 years ago today. I became a second lieutenant. It seems like I just came back from my reunion. Some of those guys have gotten old.
Denny and I had an opportunity to speak for a few minutes ahead of time. There are a ton of topics that we could go over. We should go over probably, but we have 20 minutes. And so what I really want to start with is a comment that you were making about the threats to the American way. And everyone who's listened to this show for a couple of times knows that, like everybody, probably all the listeners, I'm a huge patriot. I believe in America, but I really, really believe in what the founding fathers put in place. There's threats to that every day. Let's dig a little bit into it, if you will. You have your thumb on the pulse of it a little bit more than I do. But where do you see risks to the American way and what we all love and fight for?
To me, the very clear biggest danger our nation faces is the hate that Americans have for each other. That's not all Americans and it's. But the media is full of it. The people who are speaking out, too many of them. It's closed minded hate, which means you're speaking by your emotion, not your intelligence. Because you and I might totally disagree and not just the Army Navy game, but we could. There could be some serious topic that we disagree on and still be friends. I disagree with you, you disagree with me. We agree to disagree if we're in politics. I don't like what you're doing. You're my elected representative. I can either hate you or I can find another candidate to run against you at the next election and work to help that person. And that way I don't have to hate you. And there's no benefit to hating you unless you're Hitler or somebody. And that's how politics has worked in the past. But all of a sudden in the last couple, three years, it's I hate you. Anything anybody says bad about you, I will repeat as if it were fact and name calling. Oh my gosh, how many times have you Heard somebody call a racist. Have you ever defined the word racist? You know, if I'm a racist, that means I think in at least one case my race is superior to some other race and everybody in that race is inferior. That's what a racist is. I think that's what the dictionary says. But we throw the word racist around and once it's thrown, it's assumed to be true. Yeah, that's obscene. It's destructive. And here's the. Let me get to the major point here. If you and I disagree on something, we can disagree and be friends. We are Army, Navy, but in other things, too. But the minute I attack your humanity, not attack your facts, but attack your humanity by calling you names, a racist, a bigot, a homo, whatever, some kind of phobe. Now it's hard to be friends again because I've attacked your humanity.
Right. That's a critical point.
How about if I have a problem, I attack your facts, you can respond with your facts and maybe we'll agree, maybe we won't agree, and maybe, just maybe, we'll each learn a little bit. That's what America's supposed to be like. That's what it's been like. But, wow, that really bugs me.
Yeah. You know, two quick things come to mind is, you know, Robert Kiyosaki talks all the time about, you know, we go to war when people can't stand on the edge of a coin and look at both sides, can't unemotionally just consider the other side. So, you know, you go to war when there are two people, two countries, two factions, and they're both right, and you're in big trouble when that happens.
Right.
When you get emotionally involved, when you've decided that I am not going to consider the other side's situation because I'm right and therefore they're wrong. And it takes a whole lot of emotional maturity, just intellectual maturity, confidence in yourself to be able to take the step into that foreign territory, to actually consider the other side. So the other one was a comment from a mentor of mine after the most recent election, the induction for President Trump is, and how it was a change of power from completely opposite individuals that was nonviolent and civil and actually pretty cordial. And only in America can you do that when it's working. Right. But you're right. Only in America also can you get away with saying extremely, extremely hateful things at other people. And because of your right of free speech, you get away with it.
And my concern beyond that is if I'm in One name calling family and you're in another name calling. And our kids suddenly serve in the same infantry unit. They're not going to like each other, I would presume because they're going to bring some of their parents bias with them and yet they're going to be in the same co, Ranger infantry unit and their lives are going to depend on each other. We're breeding distrust into the next generation. That's scary from a national defense perspective.
Yeah. I mean, certainly it's been there throughout a lot of American history. Right. You know, there has been that distrust that we learned from our parents and watching them operate. But it does seem like in a lot of places it's getting worse. I think that's just the civil unrest side of things. I think it's the bleeding down of the American middle class and people feeling hungry, feeling like they don't have a way out of the box. You know, in a time of supposedly really good economic conditions here, there's a whole lot of unrest. And I think that comes from that results in name calling and people blaming others for their problems.
And part of that is we're also losing our value set. It's politically correct to attack Christians, but it's not politically correct to talk about. Well, and Jews, but it's not politically correct to say anything bad about Islam though. Most violence in our part of the world has at least some ties there. And I'm not trying to blame everybody in Islam, I don't mean to do that. But how about having some values? How about decency and loyalty and that kind of thing being important?
Well, it takes a big issue to do that and it's impressive to watch when it happens. It's one of the things that I look back on my time in the military and really value just didn't come across very many families. When I would visit somebody at their home or get to know those that worked for me, I didn't find too many families where we had a poor value system. There was a little, maybe, but they certainly are not a typical slice of the current American pie.
True. And we gotta look at where this can go. China is certainly the biggest power in the world next to us. And if you recollect, it was today in Tiananmen Square when the students had been protesting wanting more rights, and it was today. The army moved in and within 24 hours they killed or destroyed or arrested tens of thousands of prisoners of Chinese citizens who wanted liberty. And that's the threat. If we get too strong a central government, that does happen. And you know, that happened today in history in the 60s. So we got to be careful. They are our challenge and there's a big threat there. We got to be aware of them. And certainly they are the big influencer on Korea, have been forever. Another aspect that's a dangerous area. We need to look interesting enough, you look south of the border in Venezuela, it appears that Russia is pulling out of Venezuela. I have a funny feeling it has to do with some economic sanctions that they're having to deal with.
Yeah, I think you're right. I've been watching the same thing. It is very surprising. This is a little bit of a side note again, but what came to mind was a discussion I was having with my oldest son recently about he was frustrated with his civil government class and how it seemed like people were talking in circles and how it seems like, you know, in the studies that they've done that not a lot gets done in America. And I said, well, that's a bit of an understatement, but there's also some beauty to that. The three legged government that we created, that our founding fathers created is brilliant, you know, and it seems like I've spent five years working in D.C. and swore that if I could possibly not do any more, I would not do anymore. It frustrated me to no end, the entrenched interests and the slowness of everything. But there's a beauty to not being able to move fast with those checks and balances. I mean, the most. And this is what I was telling him, I said, you know, if you look throughout history, the most efficient governments that could really get stuff done, they were impressive. You know, think of Germany under Hitler and Italy under Mussolini and there's millions of examples, thousands of examples at least where they got a lot done, but it was not good in most cases.
It may have started out looking good, but it sure didn't end up that way.
Right? Yeah. So the check. I'm a big fan of the checks and balances and maybe moving a little bit slower, maybe even a little bit more expensively. It's super expensive to end up with concentration camps.
Well, I spent 15 years teaching American government at college and I could not agree more with you. We need to return to our Constitution as written. It's a legal document that says what it says and doesn't say what it doesn't say. It's not subject to somebody interpreting, oh, it really meant this. And tomorrow it'll mean something else. And if we can get back to the Constitution, our liberty and our freedom is pretty Much protected. And even as abused as the Constitution is now, as you just pointed out, we live a safer life than most people in the world.
We do. We do. I spent 30 minutes on an airplane recently and had down, you know, I download stuff and say, I'm going to watch this on my next airplane or read it. Excuse me. And I just read a five or six page thing on the difference between republics and democracies and how a republic is necessary for capitalism. It was fantastic. It was stuff that I probably should have learned in your class, maybe did back then, but I needed a serious refresher. So I just, you know, I challenge everyone out there. Go read about that. It's very simple. You can find it on Google. There's a big difference. There was a very specific reason why our founding fathers wanted a republic. And it says it and absolutely did.
Not want a democracy.
Absolutely did not. And that's why we stand up and state it in the pledge every time. But few people understand that and I think we don't stress it and obviously don't stress it in the education system enough.
So just as a coincidence, coming up, a month from Tomorrow is the 4th of July. I asked students, why do we celebrate the 4th of July? What happened? Most of them had no clue that the Declaration of Independence was passed by Congress on that day. Independence Day. I know very, very few people that have read the Declaration of Independence. A few have read the Constitution or at least parts of it. Wow, we got to do that. I mean, you and I took an oath to support, defend the Constitution, as did everybody in uniform. Have they read it? Do they know what it is? We took an oath to support and defend. That's something we need to strongly encourage.
I would hope so. I mean, even just, you know, the preamble, that would be a really good one. There's some good, there's some good, important items in there. Well, so you wrote a pretty amazing book called the Smiling Life and Career of an Army Ranger. And I've read excerpts. I have not read the whole thing. I want you to tell the audience what it's about first because it probably the smiling part might lead them to it. And then a couple, if you would, a couple of quick examples.
It's a story of me in uniform. It actually starts with high school ROTC and goes through my time at west point and my 22 years on active duty and a little bit of post military time. And it's mostly a series of short, funny instances that I lived through. A few of the comments are not necessarily Funny, but most of them are. I've never taken life too seriously unless somebody's shooting at me. So I have a funny look at it and there's no theme. I sort of thought about it later as the ideal book to put in your bathroom because you can pick it up and read one or two or three pages and put it down and pick up, read some other pages another day. You're not missing anything because there's no theme. It's chronological. But that's the only thing and I've lived. Life can be seriously funny. One of the funnier things now wasn't at the time I was a company commander in the 101st Airborne Division. My company was the immediate reaction force for the nation, which meant we had to be one hour after somebody blew the whistle. We had to be a parachute issue, ready to go anywhere and stay as long as necessary. One Saturday afternoon, they blew the whistle. We were there in like 30 minutes. Parachute issue was closed. So we knew it was not going to be any. It was just a drill, but that's okay. And our new commanding general showed up and started yelling at us because my troops were just sitting there in a truck waiting to be told what to do. And it was a hot, warm, sunny day. Some of them were snoozing and they should be cleaning their rifles and they should be doing this. And my new battalion commander showed up and got in the general's face. Now this is about a foot and a half in front of me. And told the general to sit down and shut up. That these guys, if their rifles weren't already cleaned and it wasn't already done, then I should be relieved and they are already clean and soldiers should be sleeping now because infantry troops never know when they're going to sleep next. And the general left to make an understatement. I was in shock. But the colonel was right. And looking back at it, that was pretty funny. I don't remember the last time a lieutenant colonel told a two star general to sit down and shut up. He didn't actually use those words. That was. I don't remember what the words were. I was too much in shock. But he was right. And by the way, that colonel had been my tactical officer at West Point. So that's something I can relive almost instantly by closing my eyes and seeing the look on that general as the colonel told him off.
Wow.
And incidentally, the colonel made brigadier general, so therefore I guess it didn't hurt him any.
Well, something tells me he was right. That's why the general stood up and walked away.
Wow. So there are instances like that. Again, they weren't necessarily funny at the time, but looking back at them, they are funny.
Well, it's nice to be able to put things in perspective years later when you look back on them. It's also nice that we remember mostly the positive things and not the negative ones. That's a nice thing about the human history.
There are some of those. You were the commander of a ship, right?
Yeah, I was, yeah.
Submarine D day. I just was rereading about it. There were 6,000 ships and boats involved. Wow. You've got to be a pretty important person to be the skipper of a ship or boat. Can you imagine 6,000? I'm sure some of them were small fishing boats and stuff like that. That's an amazing number all by itself, isn't it?
That's an incredible armada. It absolutely is. Wow. I remember seeing pictures. I certainly didn't see 6,000 in those pictures, but it was just you could look like you could walk across them like stones on a street, just getting them not to run into each other.
Yeah, I'm sure that was no minor issue.
Yeah. So, Denny, you run a radio show that's also a podcast, I guess, and you're on, coming up on 600 episodes. Tell us the focus. You know, I'm familiar, but please tell the audience the focus of it and how they can find it because it just seems really inspiring to me.
Well, Front lines of freedom. Frontlinesofreedom.com is the website. We're on 180 something stations and we post a podcast after it plays. It's a weekend show, plays once a week. It's two hours. We started our 13th year this month, so we just completed our 12th year. The 600th show is coming up this month. Again, it's a two hour show. The theme is to talk about our military, the military, the veteran community, homeland defense, foreign policy. Things that impact on our nation and the people. It's not so much you and I talk about our time in the military and sitting around the campfire kind of thing. It's not that very much at all. It's more of a discussion of challenges facing our nation from every perspective, including the ones we just covered just now. I've had cabinet members and privates and corporals and wives and kids and officers of all ranks and politicians and you name it, we get them on. And we try to not sell a point, but encourage people to think about things. Yeah, I sell patriotism, but it's okay. If you don't buy everything I sell. So focus on. Well, National Police Week was a couple, three weeks ago. We had one whole show focusing on police. We've looked at racism and its impact. We wander all over the place. But it's the military veteran foreign policy focus that we cover. It's fun, and I guess it's unfortunate. There's so many things to talk about that affect our foreign policy and our defense situation, but there's no trouble finding things to talk about.
If the listeners wanted to go and grab one or two of the top ones that you can remember, where would they go? You don't have to give me a.
Number, but frontlinesofreedom.com and click on the shows. The two most recent shows podcast will be on the front page. There's a tag that'll get that. And every show podcast, is there any.
Like, guys, you got to go back and listen to this one or anything like that that a specific one that comes to mind or anything.
There are so many that the one National Police Week was, I think, the third week in May. The show at the beginning of that one was all about police. It's the first time I've ever done that. I'm very pleased with how that came out.
Nice.
Because as we were talking before, police officers are not our brothers and sisters in arms, but they're our first cousins in valor because they go out every day and to defend people they don't even know, some of whom don't like them. So I'm an admirer of the cops and first responders. I can't leave firefighters out. The other folks, too.
Wow. That's awesome. Well, as I expected, our time came flying to an end already. Colonel Denny Gillum, US West Point graduate, 22 years in the Army, Airborne Ranger, two combat tours, two Purple Hearts, seven awards of valor. Thanks so much for joining us and letting us enjoy some of your past experiences and your words of wisdom. We know where to go to find you. Any part of the parting words, Denny.
Can I my final words be beat Navy?
Of course they can. You go for it. I'll edit it right out. No, I'm just kidding.
Thanks so much for joining us.
My pleasure. God bless you.
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