Gary Wilson: Retired At 40

Episode 359: Gary Wilson: Retired At 40

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REIS 359 | Owning A Business


Owning a business is not something that you can just take for granted and coast through, which is why at the end of the day, business owners are in a class of their own. But if you put in the work, it is possible to achieve infinite amounts of success that put you head and shoulders above your competitors, achieving things that not many people can. This is the story of Gary Wilson, a renowned figure in real estate who retired at 40. Gary shares his story with Mitch Stephen, and they discuss the good, the bad, and the nearly impossible parts of owning a business – and how to jump through those hurdles with grace. If you’re looking to get started on your own business, this is a great place to start.

I have Gary Wilson. He’s coming to us directly from down the street in Disney World in Florida. He’s got a lot of interesting stuff to talk to us about. One is a unique thing that we don’t talk about every day is teaching real estate agents how to deal with real estate investors, which is sometimes oil and water. Although if we look a little closer, there’s a great symbiotic relationship there, for some reason there’s usually a little friction there. You have to learn how to overcome it. Before we get started, I want to pay homage to my sponsor, TaxFreeFuture.com. If you do not have a tax-deferred or tax-free retirement account or a place in which you can grow your retirement or grow your finances tax for your tax-deferred, you have no idea the size of the tool that you are missing out of your belt. Please go to their website and give the little mini information, their micro information and check out the 37 videos of what you can do with these accounts. I went to a three-day seminar. It’s one of the best things I ever did was they taught me how to grow my retirement fund from a little bitty tiny bit of money to a whole bunch of money and it was worth every penny. It changed my life. You will not believe what your financial advisors are not telling you. Gary, let’s do a little background. Tell us about the bullet points and then we’ll get on with some of the nuggets there.

I started my first property I bought on January 20th, 1986. I graduated from college. I bought it with my college roommate. His name is Socrates and his dad’s a Greek immigrant and he helped us buy the house. It never gave us a dime. He didn’t give us the fish. He taught us how to fish. If you remember 1986, a huge Tax Reform Act came out and it took away a lot of loopholes for escort-type people like dentists, chiropractors, doctors and so forth. What created a huge opportunity for young guys like me that didn’t have anything, we’re broke. You’re getting out of college, needed jobs, things like that.

That first house was a 4-bedroom, 2-bather ranch where we bought. We assumed the owner’s mortgage. It was a VA mortgage. We refinanced his second and we gave him a third note for the remainder of the equity. I get married, Socrates buys me out and I put in about $3,000 total. It got out of about $8,000 and I lived there for a whopping $50 a month. We’d rent a dealer, two rooms out to two other guys and their rents covered all the debt on the property show. That was what made a believer out of me, Mitch. If it wasn’t for that, I might not be doing this.

What was your a-ha moment? Maybe you ought to check into this because I did that. My story is similar. It was a realm. It was the same time the Tax Reform Act killed the industry. There were 800 foreclosures per week and there were many that they weren’t even doing them at the courthouse steps. They were doing them per week at the border realtors. It was a silent auction. You wrote down how much you wanted to pay and put it on the envelope and turned it in. If you were a high person, you got it. It was a lot of assumable loans back then, VAs and FHAs, and I did the same thing. I moved into mine and lived there until I decided to sell it. I accidentally made more money selling it than I did the whole year at work. That was my a-ha moment like yours, exactly the same. What happened?

I was young enough and naïve enough not even to know that maybe I should be fearful or whatever. It didn’t occur to me and thank goodness it didn’t. Several years went by, I’m 35 years old. I’m sitting there dreading the corporate world. I’m working, I’m getting promoted, moving up the corporate ladder and hitting it. Soc’s dad taught us when we close enough property of making sure pounding his chest and a few boys do it a ton of you won’t have to work for anybody when you’re 35 years old. I wake up and I’m 35, married, have two kids, living in Pittsburgh, away from the beach where I should be.

I said, “I’m going to start buying properties because I’m going to get out of this corporate gig.” In a few years I retired. I retired when I was 40 years old with a couple of 100 units and never looked back. I’ve built out of that. I built a brokerage company, a title company, an appraisal company, a property management company. The reason is the agents were not prepared to help me, Mitch. They were not trained to help me invest. They were helped trained to help you and I buy and sell our homes. They’re frustrated that live in there. I said, “I’ll get my license, I’ll take care of this.” Thinking, “How hard can that be?” There are those guys who do is open up doors and look at the pretty carpet. It turns out it’s an entire industry that has its set of rules or regulations and learning. I decided to master the game and I was already teaching investors how to invest in another company.

They were all asking me, “Can you be my agent?” I’m like, “I don’t want to do that.” Finally, after about 100 times and thinking, “Maybe God is trying to sell me a shot,” that’s when I decided to say yes. That opened up the whole role of a new income. I had my passive income for my rentals and flipping and all that. I built this business around working with the investors because I understood that and they knew that and that turned into a big business. I’m living the model of having business and real estate ownership. When you get that powerful combination, the world is your oyster shell. You can do anything you want. I’m living proof and I believe, Mitch, if you knew me when I was a kid, we’re good. We’ll close. I was in a school lunch program. I’m the least likely example of somebody to be teaching other people how to do this. I went to Old Dominion University and studied Computer Science. I couldn’t tell you exactly what it was I learned.

You learned how to get up in the morning and pass a class. That’s what you learned. You’ve covered a lot of material right there. One is this business offers a lot of offshoot opportunities. I have eight companies but they’re all finally related to the core business of buying and selling my house. I sell houses on 30-year mortgages with a 10% down payment. That’s my model. Not many people have that model, but I buy houses with OPM then I sell them for 35%, 40%, 50% markup and I carry the note for 30 years no balloon. I need a 10% down payment, I need to like you. From that became the hard money loan business and it goes on, the self-storage business. One of the things I want to point out to the people reading is you’ve got to master the one thing first. You don’t get spread too thin fast. How long was it you were talking in terms of either length of time, net worth or whatever before you jumped off and started doing the second thing?

REIS 359 | Owning A Business

Owning A Business: Real estate investing is not the end game; it’s the foundation upon which you launch other businesses.


I started investing in earnest when I was 35 and when I was 40, I decided I’m going to start my broker’s company. I didn’t do it right away. While there was, I got my license, started building the clientele, the brokers I worked for, Mitch, check this out. There were 30 agents. I ended up out-producing the other 29. My production was greater than all the other 29 agents put together. I thought, “I’ve got to start my company.”

Tell me if I’m on the right track, is you’re trying to teach the real estate licensed community, the agents out there, even the brokers maybe is that you can be in control of your destiny. Go out and find deals for people that you have a list of people that buy deals. You’re not waiting around for a listing and none of your competitors are doing this. You’d be interested and we probably need to talk after the show. I have a course that I’m developing. It’s not a course as much as it is a touch system to take the 20,000 realtors in my town, find out the 100 that are going to look out and be eyes and ears for me. When they see something interesting, they’re calling me. If they all get me a half a deal a year, that’s 50 deals. I have this complete touch system complete with greeting cards that I had manufactured one for every year. Maybe there’s a way to team up on this, I don’t know. You have a great idea because real estate agents do not understand this at all. Not all of them ever will. All of them will not get that through your head.

It’s about 1.5%. I’ve taught in all lower 48 States, 3 Canadian provinces, in classrooms, the average for twenty people per classroom over 24,000 each. We’ve measured this of all the agents in North America, only about 1.5% has an intentional game plan to work with investors. This was in a residential or commercial role, 200, 300, 400 properties. You can get bigger properties but going backward, what happened is I did launch the brokerage, which the market was dropping like a lead balloon. In the next few years, my brokerage company grew six-fold. We doubled three years in a row when every other brokerage was diluted. Half the interest left the business.

What happened is Coldwell Banker, RE/MAX, Dave Liniger himself sent five executives from Colorado Springs to come to see me in little Pittsburgh, Pennsylvania to buy my company. I’m like, “Why would I sell it?” Coldwell Banker, the guy showed up with a checkbook, “What do you want?” They didn’t have the model. Mitch, I will be the first to admit, I didn’t plan this way. I didn’t plan the recession. I call it the forced gut moment. I happened to have the one boat that was out of the water when the hurricane hit, I survived and all the other boats were inshore getting smashed up against the dock. That’s what happened.

Isn’t that interesting? I never planned to write a book. I never planned to open up a loan company. When I bought my first storage unit, I didn’t have any idea it would be the thing that would set me free faster than anything in the world. I woke up one day when the bookkeeper came and said, “Your storages are kicking ass.” I looked at how much money they made and said, “I’m freaking done.” I don’t have to do anything anymore if I don’t want to.” Have you done this before? You go into that “I don’t want to do anything” mode and then you find out that’s not where you live, so you go back.

When I retired when I was 40 years old, I’m going out in the morning sitting on my deck with a newspaper and a cup of coffee and watching my neighbors speed off to work. I felt guilty. It took me about a year to get comfortable being financially-free and ended up working harder. By the way, they ended up, that’s when they built that business. I’m like, “I’ve got all these clients that I’m serving them through my agents to invest in real estate.” They all ask me for property management. I said, “Sure.” In my third year of property management, it outperformed my brokerage company and then I said, “We’ll need title insurance.” I took the title exam. I’m not an attorney. I passed the first time I was sitting there in a room with all these attorneys. They’re scratching their heads and they call me the guy in the green shirt because the instructor is asking all these weird questions like, “What would you do in this scenario when you’ve got a title issue and this and this?”

I was raising my hand all day long because I had seen all those. I did over 3,000 REOs and I’d seen everything you could imagine, but any case going forward, I realized, “I don’t want to do lending.” We did launch a lending business, but Congress changed all the rules in 2000. I decided, “Let’s stop that nonsense.” I kept the appraisal business and sold that. The point is I want everybody to pay attention. It’s all about leverage and everything I’m describing to you is focused on one thing, which is real estate. When you serve people out there in the world of real estate, it’s one of the three: food, shelter, clothing. We’re providing shelter. It’s an endless supply of business. If you can leverage that one thing to provide other services, I promise it’s like Zig Ziglar said, “Help enough other people get what they need, you’ll get plenty of what you need.”

I service notes for myself all day long, hundreds of notes that I created myself. I got tired of saying no to people, “Will you service mine?” “No.” Finally, it’s like, “There are a lot of people that need this and apparently whoever’s doing it out there is not doing it well because they all want to leave.” I started a note servicing company, but I want to reiterate. I got good at the one thing first for 5, 6, 7, 8, 9, 10 years. I was a pro at that thing and then I had a team that was managing that thing. Will you agree with me on this? Yes or no? Anytime you start something for some time, usually about two years at least it takes everything you have as a human to get it off the ground. Is that right? 

Many real estate agents are not trained to help people invest. Share on X

It does.

That’s what I figured out for me.

For me, my one thing was owning residential multi-unit rentals. I ended up growing, doing, started the singles and duplexes and moving up eventually, bought big 70, 80-unit apartment complexes. I started with me focusing on residential multi-units and Mitch, which gave me the foundation upon which I can launch these other businesses. Here’s the truth about this. Real estate investing is not the end game. It’s the foundation upon which you could launch these other businesses. If you study what we call the cashflow quadrant, you will find out building businesses, merging them and selling them ends up becoming the real big.

That’s what lets you be financially friendly. I have no debt. I have no business debt. I’ve got no personal debt at 57 years old and I wish I could have everybody feel that feeling. It’s an amazing feeling. It’s not that I didn’t borrow. What would I do as I acquire properties? I’ll acquire the assets with cash and then I improve the asset, make it more valuable than putting its mortgage on it. They’re typically 50% loan to value. The reason I’m on cash is I’m anticipating we’re going to have a correction. In fact, we’re probably experiencing it and it’s going to be like Christmas time. I’m going to be ready because in the beginning, I did leverage. I was leveraged up to my eyeballs.

I was 100% in debt. I started watching what their reach was doing, REIT, Real Estate Investment Trust. Watch what they do. They’re big because they’re good at it. They’re not good at it because they’re big. Watch that model and you watch Robert Kiyosaki, Grant Cardone, all the people that are on TV, you’ll find out they’re doing something similar. They might have a specific little twist or turn to it but at the level that we’re at, they’re 800-pound gorillas and there’s plenty of room at the top. This was the craziest thing I’ve ever seen it. I thought it’d be tougher the higher I went. It’s not, it’s easier. If you’re at the bottom of the pyramid scrounging or clawing your way up, have faith, reach up and ask for help. That’s the biggest lesson I could tell people. Don’t be afraid to ask for help. Wherever you are, if you want to be at a different level, you’ve got to think at that level first. The only way to do that is hanging around people who are already at where you want to be. You’ve got to take the training. You’ve got to join masterminds.

You think masterminds are expensive. The last one I went to cost me $30,000 if it costs me a penny for that year because it’s not just the fee upfront, there are the hotels, the plane tickets, the lost opportunity, the time away from home and all that. It changed my life. It got me to a point where I could say, “I haven’t seen the last 350 houses I bought. I haven’t seen the last 350 people that get into my houses. I haven’t seen any of them.” That was from a mastermind. You’ve got to get that foundation to know and understand what people are talking about when you get into the room. If you go from dead zero into one of those masterminds because you have the money, you’re going to be sitting there with a blank look on your face. You’re not going to know. You’ve got to get the level that you understand and keep going up. There’s always another level, isn’t there?

Yeah. What’s interesting is if you focus on your part in your mind first, success is an inside job. Materially, the house you live in, the car you drive, all that will follow. You don’t gain materially and then all of a sudden, you’re thinking at that level. You’ve got to think at that level first and then materially that will catch up. The thinking has to come first.

That’s critical too because material things will kill you fast. What we’re in this for is for freedom, not money. I would say this in my book, I said, “If we can earn our freedom by collecting jelly beans, then everyone out there would be given a course on how to collect jelly beans.” Unfortunately, we buy it with money. You want to be a monk and then we’ve got a different thing. Most people buy their freedom with money and that’s what we’re out there to study. I got people that come to me all the time go like, “I don’t know how people make money like that. How do people make money like you all make money?” I said, “Let me ask you this, how many hours have you studied money?”

REIS 359 | Owning A Business

Owning A Business: Success is an inside job. Get to that level first, and then you’ll catch up materially.


If that’s what you want and you’re not studying, how would you expect to fly if you didn’t take the flight school? Jump in and hope you don’t crash. That’s not a good plan. You probably need to start headed towards the barn here. Gary, I haven’t met you before, but I love your personality. I love your take on. We were talking before. I’m connected with you as far as your style. You’re probably someone I should meet personally soon. I want to let the audience know Gary gives a free 30-day trial for everything. You get a password or code or whatever. Go to 1000houses.com/Wilson and get a pass. We were talking about there’s more free stuff than we can sit here and list, but give us a little bit of what’s over there.

There’s a ton of content. I’ve written seven books. I got three more in a hopper and the first five, if they go in and click on the member’s area, the left-hand side you’ve got to be a member. Right-hand side, they can go in and check it out for free for 30 days. Grab the first five books, flipping, buying rentals, managing rentals, wholesaling, what we call the Investor Agent Program, where you combine being an agent and an investor or serving other investors. Also, there are dozens of web links to allow you to research anything you want on any person, any property which is critical and eventually you’ve got to have data first. There are reports on how do you know who’s paying cash for properties in the area?

Where can you get the report? It gives you the name and address and the properties they bought. There’s even a private lenders report. It shows you who’s lending money privately. It gives you their name and address and the properties that they financed so you can match up with the right people. There’s also a community site where you can set up a profile login. There are thousands of people out there, all professionals, business owners and the investor agents we train to work with us around there. You can network, you can look for properties, sell properties, do joint ventures, all kinds of stuff. That’s the tip of the iceberg. I don’t want to go too far because it probably overwhelms people.

Others jump in with their toes, grab what you want. That’s how we do things. Back to Zig Ziglar where I learned and he used to tell me that. By the way, my grandfather knew him personally. They served together in the Army and never met the man personally. I’ve got all his materials. He passed away but he said it perfectly. “The secret to wealth is serving as many people as you can. You’ve got to have a servant’s heart and you got to give, and the receiving comes from the giving but it’s honor-based. It’s what we call prosperity through service, serve first and you shall prosper as a result.” Is it true? I can’t put it any simpler than that.

The greatest self-help book in the world was written about 2,000 years. It’s called the Bible. Everyone’s been ripping off the Bible ever since. Zig Ziglar, The Secret, everybody, it’s all in there. It’s all been said before. They’re repackaged with a different cover. Giving your showers, get back ten-fold is exactly what you’re talking about. I’m not a theologian, I can’t quote, but I’ve been to my church enough to know that it’s all been written before. One time in a seminar, someone asked me at the end, what’s the most influential book you’ve ever read? The slap cues my mind in a split second, this is the Bible.

Split-second was there are 150 people in this room probably would be considered politically incorrect for me to say that, the second flash, “If I deny my God, he will deny me.” Next flash, “I’m spurting out. It’s the Bible.” The hot thing at the time was The Secret, you send out your wishes to the universe. I said, “The only difference between The Secret and sending out a message to the universe and me sending out my messages, I figure I’m sending out the message to the guy who made the universe.” That’s all the difference in the belief system and it’s all been written 2,000 years ago. If you want to know how to conduct your business, it’s right there. Honestly, you give and that person is the one who’s the most rewarded. It sounds cliché to say I want to give back, but the words of that are huge.

True giving is giving when you don’t even think you’ve got anything to get like you’d give of yourself. Funny thing is I’ll go back to tell this, the Bible has out-printed and outsold all the other books in the history of the human race combined. When people tell me, “I’m not religious. I don’t believe it.” I was like, “That’s okay. Read it because it’s the number one business book in the world too.”

It was the only time in my life I got a die-hard standing ovation. You feel like sometimes you put yourself on the line for this stuff, but there’s a lot of believers out there and for a good reason.

The US Constitution doesn't protect other people's feelings from being hurt. It protects Freedom of Speech. Share on X

Our US constitution doesn’t protect other people’s feelings from being hurt. It protects our freedom of speech. I don’t think our forefathers intended us to contain what we believe, what we think. They wanted us the freedom to express it. Whether you’re Buddhist, Muslim, Hindu, Jewish, Christian, whatever, express it. Be proud of it. I love getting cards. I get Kwanzaa cards, Hanukkah cars every year from my tenants. I’m glad to get them. I send out Christmas cards, but I’ll tell you the second-best book is Think and Grow Rich by Napoleon Hill. I’ve been able to meet his grandson. They’re from rural Virginia. That’s where I grew up. That book, the foundation, the fundamentals come from the Bible.

The whole principle of the mastermind comes from Jesus and the twelve disciples. That’s where that comes from. Harvey Firestone, Edison, all those guys got together in Sarasota, Florida 3 or 4 times a year to mastermind because they knew they could help each other out, even though they were in different industries. Ford was there, they all were there. All the stuff’s out there. Success leaves clues. Learn, read, study, take the training. The main thing I can tell you is we can all read books, but to excel, you’ve got to have real trainer-led training. That’s the difference. How do you go from the learning to the execution? That’s training. Most people will, “I’m going to get the book and I’ll figure it out.” We can all figure out.

You can do that, but I tell everyone, you’re going to pay the street or you’re going to pay the mentor and the street is ruthless. The street will take everything you have and spit and kick you to the curb. There’s low encouragement there. The mentor gives you like, “Here are our choices. What’s your risk level? What do you want to do?” You go in with some confidence and you got a cheerleader generally as well with a mentor. “That’s all right, don’t worry about it. We’ve got some other things we can try or whatever.” I do want to back up and digress. Think and Grow Rich came to me at a low point in my life and my mother thought that it was a neat book and she had no idea of the magnitude of this book.

She was at a garage sale. She asked about that book and someone spoke highly of it. She brought it to me and had no idea of the magnitude of that book. I had no idea of the magnitude of that book. I was having a hard time in my life. She begged me to read ten pages a day of this book. That’s when I learned that reading could change everything or that learning from someone else’s written or oral experiences could change everything because I never stopped at ten pages. When I started reading and I had to make myself because I was in a depressed state. By the time I finished reading, I was not in a depressed state. I was starting to think of, “I can do this.” I didn’t have a college degree. I was capped. Things weren’t going well and no one ever taught me about entrepreneurialism.

They didn’t teach it at school. It wasn’t in my family. What was cool about that book was it showed that wealth could come from damn near any place on earth from almost anybody. Sometimes the people that were the less formally-educated were doing better because they didn’t have a choice. It put them on a different path and they became entrepreneurs. That’s when I decided that I would be an entrepreneur because I recognized that if one, if I couldn’t make $12 an hour by myself on the street, then I needed to go, I don’t know, shoot myself. When I figured out how to make $12 an hour, then I learned how to make $18 an hour. I was the 100% recipient of the $6 increase. When I learned how to make $25, I was 100% recipient of that. Soon, all my friends that are CEOs and whatever, I’m doing well. They jokingly get mad at me like, “You little runt. Look what you’ve done and you didn’t even go to college.”

The fact of the matter is lawyers, accountants and doctors make a lot of money. They’re at the top of the food chain in the working class, but people who own businesses are in a whole different class.

You have to be careful about the businessman. You can get in a business where you’re on a hamster wheel, run into pay the payroll every Friday. You’ve got to be careful about that because there are businesses out there. We’ve got to be careful about that because we don’t sell the business out when it’s not the right business. You end up a slave working longer hours and having more risks and maybe taking less but that’s a whole other topic. I want you to go to 1000houses.com/Wilson, you’ve got a 30-day free trial. This man has a ton of information. Go in there and get it for free.

I know what he’s banking on because I do the same thing. You connect with him and you read what he’s doing and how he’s talking to you and how he’s teaching. He’ll get his share of people that understand that he’s the right person for them in this endeavor that you want to conquer. I do the same thing. I don’t pound people, I don’t hard close people. If I’m the right guy and you’ll know it, Gary’s the right guy, you’re going to know if he’s the right guy for you. I’m sure somewhere in there, you can call and get a consultation with him to discuss what a more formal relationship might look like. Am I correct?

REIS 359 | Owning A Business

Owning A Business: Lawyers, doctors, and accountants are at the top of the food chain in the working class, but people who own businesses are in a whole different class.


I’m a real person and I’m accessible. You might have to do a little research online, but people call me up out of the blue, they’ve seen of you. They can go to the YouTube channel too. Hundreds of videos and something will be in there saying, “That guy gave his phone number.”

I want to thank you for taking the time. Do you have anything you want to say to the folks maybe before we wrap it up here because I know you’ve got a hard stop?

I didn’t start off at the top. I started at the bottom and I’m living proof you can do it. You’ve got to have faith, number one. Number two, you’ve got to take action. Have faith and take action. You can get to that next level. Don’t give up on yourself. Keep having faith, take action. I promise you you’re going to succeed.

I’d like to thank you for stopping by to get you some Gary Wilson over there in Florida. Please check out 1000houses.com/Wilson. We’re out of here. Thank you and be sure to check it out, TaxFreeFuture.com. Bye.


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About Gary Wilson

REIS 359 | Owning A Business– At age 40, retired as Corporate Vice-President, Mergers & Acquisitions in National Banking;

– Completed over 100 transactions per year consistently every year without a sales team or assistant, with virtually no marketing costs;

-Traded over 3,000 Investment properties in less than 5 years;

– Developed five real estate holding companies, owning more than 250 Rental Units;

– Self-made multi-millionaire by building a real estate enterprise, including: brokerage, rental management, investment services, settlement services, and appraisal services;

– Award winner and accepted into Andron Apiphenon Order of Excellence for Real Estate;

– Author of SEVEN Real Estate Investment books:

  • Rental Profits Without The Pain
  • Flipping For Profits Without The Risk
  • Turning Rental Problems into Real Estate Profits
  • Wholesaling For Profits so Everybody Wins
  • Investor Agent, Make More Money Not More Work
  • The Massive Passive Cashflow Method
  • Real Estate Reality, The Truth Behind No Money Down Investing

– Founder, Trainer and Coach of Path to Profit System, teaching more than 20,000 Agents and Investors and nearly 1,000 speaking engagements.

– Appeared on OVER 100 national and local media outlets including: CBS, FOX News, NBC, ABC, Business Week, iTunes


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