HI 134 - Running a Successful Business After Your Service with World War 1 Marine Veteran Larry Klairmont
7 Dec 2025 · 22 min
Podcast episode (HI 134) featuring Gary Pinkerton interviewing Larry Klairmont, a World War II U.S. Marine veteran (enlisted at 16) and Chicago-based entrepreneur. The conversation covers Klairmont’s military service in the South Pacific, his postwar business career (built the largest dry-cleaning company in Chicago with over 110 stores and 500+ non-union employees), transition into real estate (now running a company with ~125–150 employees alongside his sons and grandchildren), and his large classic car collection/museum (about 400–500 cars total, ~300 on display in a 150,000 sq ft building). Klairmont is a decorated veteran (two Silver Stars, one Bronze Star, two Purple Hearts). Episode recorded July 25, 2018; hosts include Gary Pinkerton and Jason Hartman.
Questions this episode answers
July 25, 2018.
16.
South Pacific.
Two Silver Stars, one Bronze Star, and two Purple Hearts.
Over 110 stores and more than 500 non-union employees.
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.
Hello and welcome to episode 134 of the Heroic Investing Show. A podcast for first responders, members of the military, veterans and really anyone looking to improve their financial future, their financial and personal lives and gain some freedom back for their time or with their time. We teach America's heroes 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 and systems in place to enable them to build a life where they can focus on their passion, that service or product that they are uniquely gifted to share with the rest of the world. My name is Gary Pinkerton and I am humbled and extremely proud to co host this show that hopefully you find helpful and inspiring with Jason Hartman, a good friend and someone I consider a mentor on real estate and life in general. So last episode, right, leading into a discussion, a great discussion that Jason and I had a few months ago, I talked about some great upcoming episodes and I alluded to one that I wasn't willing to stick my neck out there and say I was actually going to get, but we did and I moved him right to the beginning of the list and that's who you get to hear from today. I'm incredibly excited to bring to you a 95 year old World War II multiple decorated veteran Marine who had action in the South Pacific. And if you know anything about the slogging that the Marines did, island hopping, losing half their people in each battle, it seemed tremendously, tremendously scary time for those young individuals. This individual is Mr. Larry Claremont and Larry hails from Chicago, Illinois where he's built up an enormous real estate business after selling off, starting from scratch and selling off the largest dry cleaning business in Chicago. And at the time Chicago was one of the largest, I mean still is one of the larger cities, but was one of the top two or three in the country. And so his dry cleaning business with over 500 non union employees was one of the biggest in the country as well. He sold that off and he talks on our podcast here a little bit about what led him to starting Real estate after that. And he's also an incredible historic automobile aficionado. So, you know, think about this. We have the ability to hear from an individual who was born in the Great Depression. There just aren't that many of those on the earth anymore. And Mr. Claremont is not only coherent and has a great conversation with me. I believe the gentleman could beat me in a 500 yard dash. I mean, he is full of, well, I won't use the phrase that I grew up with on the farm, but he's full of vinegar. He's sharp as a tack, and still at the helm of a tremendously large, successful, multi million dollar real estate business that he runs with his two sons and actually now a third generation, some of their grandkids. His car collection, too. I can't wait to get out there and see his museum and his car collection. He's got cars from people like the late, great Jackie Gleason. He's got Shaq O' Neill's car. He's got, he's got the World War I Ace, one and only car built for that war veteran. He's got. Oh, gosh, he named so many that were just tremendous. So. And if you want to get a really good read on this, there's a Chicago Tribune article on Larry Claremont. It's called, Let me read the top here. So meet Larry Claremont, a Chicago collector as interesting as his 319 cars. So this guy could teach us a tremendous lot about a lot of different topics. And he does that somewhat in our call here. But just keep in perspective again that this gentleman was five years old in the Great Depression and he grew up without a father. And it's that moxie that keeps this young man, young at heart, man at least going strong in his mid-90s. And you know, he is a testament to what we at Paradigm Life and many of my mentors talk about. And that's this idea that retirement, the concept of retiring and retiring again means to wither away and withdraw from society. It is not good for humans. I personally, in my non medical opinion, believe that it has a lot to do with the rise of Alzheimer's and Parkinson's and other degenerative mental conditions. And it's about not keeping yourself active, not keeping yourself mentally active. Unless I go off on a historic transient, I will stop there. But I don't think there's, you know, my gut tells me there's no coincidence here between a man who gets up every day to run a company in his 90s, a gentleman that at age 88, decides that he's going to create one of the largest car museums in the world. You know, he's, he's got a fiance and she's a wonderful lady who joins us on the podcast for a few moments. People like that with visions of the future and many, many things they still need to do. Don't die off, you know, I mean, that's oversimplification. Sickness gets to all of us. But the human spirit, the thing that caused people like Larry Claremont as a teenager to march forward in the face of Japanese machine gun fire beach after beach after beach, and resulted in a gentleman who has two silver stars, a bronze star and two Purple Hearts to come back to America and create multiple enormous companies, have multiple awards for best operating company, company loved by his employees. A company that has people who work for him for more than 30 plus years. None of those things are coincidences. He'll teach us a lot about work ethic and about caring for others and about things that make you successful. And I think that I may never have a better episode than this is probably obvious in my tone and in my just awe at having had the opportunity to talk to this great gentleman that it caused me to do the promo for it right at the very, you know, right after the recording of our conversation and get it out to all of you as soon as I possibly can. I really hope you enjoyed this as much as I enjoy talking to this tremendous gentleman. There's a lot we can learn from our elders, especially those that inspire us to the level that Larry Claremont does. So my hat is off to this tremendous patriot in World War II hero. And I hope you all really, really enjoy this as I did. Thanks so much. And I'll be back with you next episode.
So, everyone, thank you again for joining us for another heroic investing podcast. I have with me a gentleman that it will take me a very long time to beat. I mentioned before his biography. It's just truly incredible. Everyone, please help me in welcoming Mr. Larry Claremont. And Larry, thank you for giving time to my audience.
My pleasure to do it for you.
Yes, sir. So you hail from Chicago, Illinois, Grew up in the Great Depression and participated in World War II. Saw a lot of action. Could you explain just a little bit for the audience how long you were in during World War II and where you participated?
I enlisted in the Marine Corps at the age of 16. I served in the United States Marine Corps in the South Pacific.
South Pacific. Tough, tough battles down there. Thank you for your service. I'll just say it for the audience. We're fortunate to have an opportunity to talk. So when you got back, you started with your dry cleaning company, but fairly quickly transitioned to real estate. And was that out of necessity, just buying the buildings initially for your. For your operating business?
Well, it's kind of a long story how I evolved from the dry cleaning business to real estate. Very briefly. After four or five years, I became the largest dry cleaner in the city of Chicago at over 110 stores. And what I learned from that was what constitutes a good location. I sold my company and was looking around for something that I live in Illinois.
My former wife and I went to the theater and after the theater I said.
And the ice cream parlor was about blocks away. And what do you do on a nice summer night in 1986, there was no television and we walked over towards the ice cream store. And what do you do? You look in the windows. And in the window was a real estate office right next to the and I saw a brochure on the building. I looked at the location and having understood what makes a good location for my former dry cleaning business, I had bought this particular building.
So location extremely important. But there was also a lot of hard work and work ethic that you probably learned as a young guy growing up with a single parent mom. Your fiance at the time, when I was reading an article published in the Chicago Tribune mentioned that and I think your wife now but mentioned that you've always been a hard worker but you learned at a young age to do some things, you have to do them right. You have to do them yourself. Is that still a lesson, one of your primary lessons?
Absolutely. If I make up my mind that I'm going to do something and I think it's right, I can talk me out of it.
Right? Right. Right.
It hasn't worked out too bad for me.
No, I would say it has not. One of my mentors comments that, you know, quality of a successful individual, a successful business owner and entrepreneur is someone who makes good decisions quickly and is slow to change those decisions. You know, where their gut tells them where the right answer is and then they stick with it, even though it gets tough at times.
Correct.
What are some of the pieces of advice maybe you would offer to members of the military that are considering going out on their own in a business, whether it be real estate or otherwise?
Well, having been a veteran, one of the things that you must do to be successful, in my opinion is to be frank and to be honest. And when you give your word and you shake hands, it doesn't have to be in writing, and you should conduct yourself accordingly. The biggest factor in any industry or any investment is fear. And fear itself should not be a conduit of making your decisions.
Right. So move forward in spite of it. If the. If the information and your gut tells you that it's an appropriate decision. I think if I'm understanding.
Yes. Yes. Correct.
Yes, sir. What about when you had your dry cleaning business? I'm guessing you had quite a few employees. Did you have a lot more in the dry cleaning business than in real estate?
I had over 500 employees. Non union.
Yeah.
And no partners.
Wow. You learned a lot about leading people.
I would imagine you got that right.
One of the things that I've learned in my companies and on my ship is that good intentions and treating people with common decency and respect goes quite a long ways.
It sure does. In fact, in my real estate company, we have employees that have been with us in excess of 30 years. And what constitutes any successful business is the quality and nature of your employees. When they start with us, we always tell them we're not married to each other. We'll try it out. If you don't like us, you can leave with no obligation. And if we don't like you, there's no obligation to discharge you also.
Right. Sounds like a great, appropriate, fair agreement.
Right. And it's worked out well for us.
That's all. And so how many. How many people in your real estate company now?
We have close to 125 to 150 people together.
Yeah. So you went. You significantly downsized when you sold that other company. And you've built up along the way with different types of people. But still, managing a company with humans is always a challenge. But it's also pretty gratifying, I've learned.
Correct.
You have family. I saw both of your sons work hand in hand there with you in the company. That must be. I mean, I'm sure that brings challenges as well, but it must be great having people carry on the legacy of your business.
Well, I have. Fortunately, I have two boys with me. My oldest son, Alfred, is in his mid-60s and has been with me for over 30 years.
Nice.
It's really, I think, remarkable between the two of us is that we have never had an argument. Never.
Wow.
And although that he sometimes feels that he is right and I overrule him, he gets overruled. And that's the same thing as to what's happening today. We're also fortunate. And having a couple of grandchildren with us in the company, it's worked out quite well for them and quite well for us. The other thing is that I'm in my early 90s now and I'm not as active as I used to be. And my oldest son Alfred, who's a dedicated hard worker and loves the company, takes care of all the day to day problems. I'm just more at this stage more consultants rather than an actual operator. Although I have not retired.
That's awesome. Well, I think the reason that you're still going strong in your 90s and many other people aren't is physically because you didn't retire. You haven't slowed down physically or with your mind obviously.
Fortunately, I'm not as not as active physically as I once was, but I am intensely interested in the day to day operations of our real estate company.
Yeah, I can read that in everything I've heard about your company and read. So speaking to somebody who is not ready to slow down too much yet, I have to ask you about this because I'm a huge fan of automobiles, new and old and so just a couple of years ago you created an enormous museum with some of the most rare cars in the country and is still going strong I imagine, right?
It's a hobby and we are really fortunate. It's one of the things that I am crazy about is classic and antique cars. Along with my fiance Joyce Oberlander who works with me on a day to day basis on the car collection. We currently have 4 to 500 cars total and about 300 odd cars in 150,000 square foot building. We kind of shift the cars around, we buy new cars and we have one of the five outstanding car collections of antique and Pulaster cars probably in the United States. It takes about four hours to really tour the whole place and it's really quiet facility which I'm proud of.
When I read a couple of articles, you know, just to share with the audience. Shaq o' Neill's car and Jackie Gleason's car. Those were beautiful automobiles. Those are pretty neat. What other historic cars? Not necessarily Mae west car. Mae West. Okay. Do you have any one of a kind cars? I mean those were all custom adjusted.
I was fortunate enough recently to acquire former President Eisenhower's personal catholic and we did not restore it. It's in the same condition as when he died and it even has a drinking fountain in the glove box. Wow, he likes fresh water. That's our display. We have R. Kelly's car. We also have a famous car owned by Eddie Rickenbacker who was the World War I airplane ace to shut down 20 odd German airplanes. He was president of Eastern Airlines and he had a special car for himself when he decided to go into the automobile. And the car is a magnificent single passenger car called the Rickenbacker. Unfortunately, the company folded up in about two years because of the economy. That's a famous person. We also have the famous car called the Tucker. And Mr. Tucker started out in Chicago. Yeah, it's one of the reasons very anxious to acquire a Tucker because it is now only in the whole unit, whole world, only 50 tuckers left and they are really collectible. It was the car of the time. It had a rear engine. It had four wheel disc brakes in the center of the hood. When you turn the wheel, the headlight turned along with the car and everybody wanted a Tucker. This is a whole long story about that. I could spend a half an hour with you talking about the Tucker.
Yes, sir. Well, I remember the movie, I remember the movie well about Tucker and his run ins with the big three automakers and how it really, really caused the loss of a great company.
That's the whole story. Right. We also have a DeLorean which nice I bought brand. I've had it for over 20 years and I bought this car brand new and we have many one owner cars. You'll see nothing like it in the whole world.
Oh my gosh. Has Jay Leno been to see your car car collection?
No, he has not been there, but I think he would like was very interesting. Months ago in California, I bought a 19:2 production Harley Davidson motorcycle. A real unusual vehicle. And it was in a couple of movies. They called and he said, I'd love to have that car, that motorcycle in my show. I said, well, I just received it from California. The freight was $300. And if you'd like to put that motorcycle in your show, you can ship it back to California. Be $300 and then if you want to ship it back to me in Chicago, it's another $300. So for a total of 600 and no profit unless you have the car. I still wait to hear from him.
Well, Mr. Claremont, I'm certainly sensitive to your time and how busy I'm sure you are. What maybe back on the business or anything else. What have we not asked that you want to share with a bunch of veterans and first responders?
Well, you know, I'm a former Marine and it's my pleasure to open up my museum to former Marines. And we have a special room dedicated to possibly having platoon Leaders or recruiters from the Marine Corps have a lecture and explain to the Marine Corps and what a wonderful institution it is. One of the greatest honors that I ever had was on my 85th birthday I received from the forced archdant of the Mercy Corps wishing me a happy 85th birthday and thank me. I didn't even know who the hell he was.
After all these years, you know?
Sure.
50 years.
My birthday we had new commandant, first guard general on same type of a letter thanking me for my service.
Wow.
What matter for the marines are those hanging in the.
In the museum?
Yes. You know, I wanted to tell you because he's too modest, but you know he has two purple hearts, two silver stars and one bronze star.
Yes, ma'.
Am.
He's amazing.
Yes. Because he was only a young kid all of this took place.
Yeah.
He was out of the service when he was 20. So it was between the ages of 16 and 20 all this happened.
Wow. Wow. Thank you so much for adding that. He's amazing and for supporting.
Okay, Larry.
Larry, Absolutely. Thank you so much for your time, sir. I will funnel all the marines I can your way and I'm going to come there and shake your hand and next time I'm in Chicago.
Thank you.
Yes, sir. Bye bye.
Bye bye.
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