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Jason Stapleton on Trump, Military Experience, and Libertarianism

Jason Stapleton is a libertarian radio host with a captivating past.

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By Andrew Lepore | United States

I was lucky enough to speak with fellow Libertarian and host of the aptly named Jason Stapleton program, Jason Stapleton. Mr. Stapleton has quite the impressive resume.

Shortly after graduating high school he served in the elite special forces group, Marine force reconnaissance. After leaving the military, he continued to put the skills he acquired in the Marines to use as he worked for one of the largest private security firms in the world, protecting and escorting high profile individuals as they traveled across war-torn nations in the Middle East.

During Jason’s time overseas he developed skills in finance as a foreign exchange currency trader, and his success in trading resulted in him leaving the private security industry, and in 2009 starting his own trade education firm “Trade Empowered”. Along with running his business, he is now the host of the Libertarian Jason Stapleton program which broadcasts live 5 days a week on the topics of free markets, non-interventionist and individual liberties.

With Jason’s unique life experience, his program receiving 9 million-plus digital downloads, 40,000 plus daily listeners, and over 500 episodes published, I had to get an interview with him.

Andrew: Before you went into the Marines, what political ideology did you most identify with, if one at all?’

Jason: I was probably what you would classify as a neoconservative. I definitely was in favor of this idea that you pull yourself up by the bootstraps, that you’re responsible for you.

I had a great distaste, even back then, for this idea that somehow somebody else is entitled to part of what you earn. I just really believed in self-sufficiency. In large part because I watched my mom work 70 hours a week to keep us off welfare. I saw how hard she worked and how she didn’t take handouts and didn’t receive government assistance. She raised three of us on $18,000 a year.

When you look at the amount of work she did and what she was able to accomplish, and we always had food on the table, I took away a sense of pride that you can do it on your own and that you have a responsibility to do it on your own, and nobody else had a responsibility to take care of you.

So in that respect, I think I had a very conservative background. Other than that I didn’t really have a well-formed political ideology.

Andrew: “What drove you to join the military? Is that what you always wanted to do?”

Jason: I wanted to get out of town, you know it’s funny I didn’t want to go to college because I didn’t know what I wanted to do with my life. Again being somebody who was somewhat discerning at the time, I could smell a racket when I saw one.

To me, it seemed like a real hustle for a guy to go to college for two years to learn general education topics so he could then spend the next two years studying what he really wanted to learn.

I’m gonna have to take out a loan for every single penny because I don’t have any money, and my family doesn’t have any money. I really didn’t want to be home anymore.

So I got a chance to shoot guns, travel the world and roll around in the mud and that’s what Marines do, and I wanted to do that. I wanted to be one of those guys, So I signed up. It was a very deliberate decision to become someone who went to war.

I joined the infantry, it was a deliberate decision to join the infantry. I didn’t want to be somebody who cooked, I didn’t want to be somebody who pushed paperwork or drove a truck. I wanted to be somebody who was in the fight, so that’s why I joined the Marines instead of Army or the Navy.

Andrew: Interesting. And that’s an interesting point with college. It’s something I worry about, the raising costs for diminishing returns.

Jason: Oh yeah the cost-benefit analysis is outrageous. Your better off getting an internship or starting your own business and failing three times, and you’ll still have less money out of pocket than if you went to college.

Let’s say you go intern for a year or you work in an accounting office or you go turn wrenches or whatever, that will help you figure out what you want to do with your life. I think there are a lot of kids, most kids, coming out of high school and they don’t have a clue what they want to do with their lives.

So it gives you some time to try out some things and see what you enjoy, and understand what it takes to kinda survive on your own. The best thing is not for your parents to light a fire under your tail to get an education and get a job than working as a night manager at McDonald’s.

That will make you realize just how much it sucks not to have money and not to have opportunity. I highly suggest kids take a look at that as an option unless there dead certain yes I wanna be a doctor or yes I want to be a lawyer, or I want to be in this field that requires me to get a four year education.

Andrew: Describe your experience in the special forces. What was your role?

Jason: I loved my time in the Marines, I spent a lot of time with Marine force recon unit, before that I was in the sniper unit. I made some incredible friends in my time with the marines.

I got to spend my days shooting stuff, blowing stuff up and tracing through the jungle and the desserts. I never actually went to combat with the Marines, I was deployed after 9/11 to Indonesia and Australia rather than Afghanistan. So I never actually went to the Middle East until I got out of the marines and I joined a contracting company called Blackwater.

I worked as a private military contractor for the state department, working with the provisional reconstruction team that basically provided security to diplomats and workers who were building roads and digging wells. My job was to provide security, its called high threat personal security work.

I did a variety of things like drive trucks, did close protection work, provided sniper overwatch, I did a whole bunch of different things based on what they needed. I also did low profile work with people who maybe couldn’t get a government escort, those who couldn’t get the state department to pay for there security detail.

They were somebody who needed a little more discretion when they moved so we would move around in gypsy vans and mystery machines and we would dress like locals and dress them up as locals and drive them around town so they would be less obvious.

Because when your driving for the state department or department of defense you got humvees you got up-armor vehicles everyone kinda knows who you are and your signature is a lot bigger.

But with the low profile stuff, you couldn’t tell us apart from anybody else on the street. So just depending on what they needed and what the contract called for that’s what I went out and did.

Andrew: That’s interesting stuff. I’ve never talked to somebody with that sort of life experience

Jason: Yeah well there’s plenty of us you know, it was a crazy time, 2005 -2010 basically was when I was contracting. I was everywhere from Northern Iraq and Mosul and Erbil to Koble and you know all over Afghanistan. So yeah it was an interesting time.

Andrew: When did you come across the libertarian ideology? Was it during or after you were overseas? How did you discover it?

Jason: You know when I was overseas, I started to recognize that what Republicans stood for, I didn’t fully agree with, and I certainly wasn’t progressive. At that time I didn’t really know that there were other options.

So one of the things I started doing when I was overseas was trading currencies. So I really started studying international finance, studying the way currencies work and central banks operate as I was trying to really understand the business I wanted to be in.

I ended up learning a lot about the really shady stuff that the government and banks do that manipulate our currency and our monetary system. In doing that I believe I bought a whole bunch of books on gold and somehow, I ended up getting Ron Paul’s book A Libertarian Manifesto, and I read that book and it was if though somebody had taken all of the things I believed and did not know how to explain, and put it all in a book.

Before that, I thought Ron Paul was a kind of cookey old man, and had watched him and thought it was funny, and you know I agreed with some of the things he said. But to me, he was just another crazy old man in Washington.

When I read that book, he wrote so clearly, and it was so articulate in the way he expressed the message, I think I was converted instantly at that point.

I went out and I bought like 20 other books on Libertarianism, Libertarian philosophy, Austrian economics and started studying these things diligently. I kinda spend the next couple of years doing that, refining what my beliefs were. Ever since then I’ve classified myself as a libertarian.

Andrew: That’s interesting as that has been how so many other libertarians have come across the ideology. They read a book or hear a speech by Ron Paul and they end up either being instantly converted or they begin the process of being converted.

Jason: Yeah it’s interesting how many people come to it when they encounter a book or a conversation. One of the things people don’t come to Libertarianism through is by getting bashed online by somebody else who challenges there opinions and trying to destroy them.

You do it by taking somebody who is already predisposed to the message and showing them the way. And that’s one of the things that I’ve tried to figure out how to do as I work my show I try to figure out a way to break down psychologically the defense mechanisms people have and do what Is called pre-framing, where what you do is you actually set someone up to be predisposed to hear your message.

One of the reasons why when somebody asks me what I believe or I’m trying to convince somebody ill tell them I believe we shouldn’t hurt people and we shouldn’t take their stuff because 99 out of 100 people will say well I agree with that.

What that does is create alignment between the two of us, and it makes it more difficult to challenge my opinions when I put forth more of my arguments.

So in doing that I try to understand there are some people, I’m not going to convince, but anybody with even the slightest predisposition to my argument I want to put as many things in my favor as possible to try to make sure they understand my argument and are convinced after.

Andrew: What’re your general views on Trump and his foreign policy?

Jason: I think Trump’s foreign policy approach is combative, I think he treats it a lot like a competition like in business. So if people are willing to give him what he considers a fair deal he’s going to go along with you and treat you well as long as you treat him well.

He’s gonna start the conversation from his position of strength or what he considers his position of strength so that he’s not negotiating on his back foot. As near as I can tell that’s how he operates period.

Now In terms of his trade policy, I don’t agree with it. I certainly don’t agree with military intervention overseas.Truthfully Trump hasn’t done a lot. He’s put in these steel tariffs that are going to be bad for America.

He’s continued the interventions overseas. He’s not much different than any other politician you run into honestly. He’s got some bad economic ideas and he’s got some good ones, and for the most part, he’s painting between the lines he’s not painting outside the lines.

Andrew: Exactly he’s not really principled, he just kind of goes with the wind.

Jason: Yeah and I’m not sure what that is. I’m not sure if there is an underlying method to his madness. Because one of the things that Trump does to negotiate a better deal is he comes off as erratic, and he may very well be erratic Or maybe he’s playing a game.

One of the difficult things with Trump is figuring out what he really believes and what he really thinks because he is constantly waffling and flip-flopping. The one constant he’s following is that he wants to build a wall.


We at 71 Republic sincerely appreciate Mr.Stapleton putting the time in to do this interview with us. Be sure to visit his website JasonStapleton.com, follow him on Instagram @JasonStapleton0321 and on twitter @Jason_Stapleton

Follow me on Instagram @Mass_Liberty, on Twitter @MALibertarian76, and check out my archived works at MassLiberty.wordpress.com.

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