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Jon Simcoe has been investing in real estate since 2005. In the beginning, he used his own money, and learned a lot of lessons. Today, he regularly does real estate deals using none of his own money. He has learned how to own or control over $25,000,000 worth of real estate.

Find Jon Simcoe online at:

Stefan Aarnio: Ladies and gentlemen, welcome to the show Respect The Grind with Stefan Aarnio. This is the show where we interview people who have achieved mastery and freedom through discipline. We interview entrepreneurs, athletes, authors, artists, real estate investors, anyone who has achieved mastery and examine what it took to get there.
Today on the show I have a good friend of mine, Jon Simcoe, who is well-known for being one of the top rent-to-own real estate investors in Canada, and he is an absolute force to be reckoned with. He’s an educator, real estate investor. Jon, welcome to this show, Respect the Grind. Thanks so much for joining me. How are you doing today?

Jon Simcoe: Doing great today Stefan. I’ve already been out this morning doing one deal, I’ll probably do another this evening. It’s multiple deal days.

Stefan Aarnio: It’s multiple deal days. Can you do a deal while we’re doing the interview, right on the show?

Jon Simcoe: I could probably push a guy that you know a little bit into getting a paper signed, and then having a deal done at that point, but … Yeah. I could probably get one in, you know?

Stefan Aarnio: Okay. Cool. Jon Simcoe, real estate extraordinaire. Well, Jon, now Jon, are you from Winnipeg? I’m from Winnipeg.

Jon Simcoe: Yeah, I’m originally in Winnipeg, or I was born there, I was raised there, but at one point I did leave and actually get away.

Stefan Aarnio: Awesome, so, Jon Simcoe, fellow Winnipegger. Now, Jon, for the people at home who don’t know you, why don’t you tell us a little about Jon Simcoe? Who he is, what he does … You know, I’ve even been to your house and seen your Star Wars collection, so tell us a bit about who you are, what you do.

Jon Simcoe: Yeah. I figure I grew up pretty much just like most people. Middle class income, grew up in a little rural area, for the Winnipeggers, it was in Oakbank, a little town.

Stefan Aarnio: Oh, yeah.

Jon Simcoe: Most people’s parents worked in the city, and that’s where you lived, whatever. It was simple, it was good, but afterwards, I decided to become an entrepreneur when I was 19, and that was where it all began. I started a TaeKwonDo business. I already had a black belt, or a couple of them, from just being a kid who just studied hard and had a lot of discipline, perseverance is probably one of the number one takeaways for success in life; if I had to ever say so, but you learn a lot of that through martial arts and in other ways.
We had this TaeKwonDo club, myself and my buddy, we grew it to the point where we had six employees. I was still a college student at the time, going to the university in Manitoba, and after that, I know I’d always wanted to buy some rental real estate and some properties. I’d heard you can make money with it, but didn’t know very much, and then at that point in time I decided to take the plunge.
I went out and did go get a house in Winnipeg, and several others since, but I decided I’d move to Fort McMurray to get a high-paying job because I figured that at the time, that’s all I knew for being able to get money, was to be able to work as many hours as you could, and for as much of a wage as you could.

Stefan Aarnio: Right. That’s the young Jon Simcoe. I love interviewing people on this show, Respect the Grind. Talking about perseverance, that’s what respecting the grind is all about. Now, young Jon Simcoe, he’s a martial artist. He’s running a little martial arts business. I was a musician, I had a little guitar-teaching business. Everybody I have on this show, they get good at some kind of discipline, then they get into the real thing.
Now, what made you want to get into real estate, Jon, out of any other thing? There’s so many real estate investors. We interview a lot of rich people on this show. Why real estate out of anything else? Why not stick with TaeKwonDo?

Jon Simcoe: I really … After stopping doing the TaeKwonDo club, I did both at the same time for a little while, then when I moved I obviously stopped the TaeKwonDo club, and continued doing more real estate. I just, I thought it would be more passive than it really is. Like, you know, you buy into most things when you don’t know very much when you’re starting out.

Stefan Aarnio: You mean passive income isn’t passive?

Jon Simcoe: Well, you still have to keep your thumb on the pulse, you know? You have to still watch what’s going on. You have to make sure that money comes in, that’s supposed to be passive, you need to make su-

Stefan Aarnio: So, sorry to interrupt you, Jon. What does that mean for the kids at home?, because there’s probably some kids at home, they got purple Kool-Aid all over their mouth from reading Robert Kiyosaki’s Rich Dad, Poor Dad. Purple books, purple Kool-Aid, they think passive income mailbox money’s just going to show up. What does it mean to say, “passive income’s not passive”?

Jon Simcoe: Passive income, it is a pipe dream, unless you have just literally lots of royalties coming in like that. There’s always some type of work to get that income; whether it was setting it up, monitoring it, or however you’re exiting, or getting your money out or back, whatever. Whatever it’s going to be, there’s some degree of activity and decisions that need to be made; so, no matter how passive it may be, it’s never really passive.

Stefan Aarnio: Right. The only passive income I can say is there’s royalties on IEP, if you got royalties that’s like really passive, or the other thing is interest on loans, like if you have like a big loan out there and it’s just interest; but even still if he defaults, you have to go and yell at the guy or foreclose.

Jon Simcoe: Absolutely. Look, I absolutely hate chasing for money, but I will. That’s why the guy who wants two grand, or six grand, he can’t afford to pay you back if he needs two or six grand, you know?

Stefan Aarnio: Yeah, yeah, oh boy.

Jon Simcoe: And then, chasing after those types of people, it’s not worth your time.

Stefan Aarnio: Yeah. Well, I had a guy come to me this last week. He wanted a 23,000-dollar loan. I was like, “Dude, I write 150 minimum,” and then, I had a guy the week before, wanted 22 grand, and I was like, “Dude, what are you even going to do with 22 grand?,” like I had a guy call me with 30 grand. He said, “Can you take my 30 grand?,” I said, “No,” and then he called me and he said, “I got 60,” I said, “No. I don’t want your 60,” then he called me and he said, “How about a quarter million?,” I was like, “Okay. Now we’re starting to talk.”.
So, talking a little bit about thinking bigger, you know? These little deals, little loans don’t make sense. What’s the minimum size that makes sense for you to make your time worth something?

Jon Simcoe: For me it almost needs to be like into the six figured. Six figured and up. I built my business originally educating, very slowly educating every person who did a deal with me how they worked, teaching them a whole lot, getting a ton of rejection at the start, but I kept going, and you learn from some of those little deals. There are some people that I would take like 10 and 20 grand from, and I learned a lot of lessons along the way, because I built it, people who are still with me, I still work with them because I’ve been their guy for so long, I’m not going to drop them. They believed in me from the start, but I won’t take anybody small like that anymore, because it’s the people who’ve given you 10 or 20 grand, that value it the most, they’re worried about it the most, and they’re going to call you about it the most.

Stefan Aarnio: Right, right. Switching gears a little bit, Jon. Do you think that success is more talent or is it more hard work?

Jon Simcoe: I believe that the success definitely has to have the hard work to it. There is a hard work component to it. I think it’s very tough to be that rockstar image, where you can just be like drunk all day, doing drugs all the time, and have hit after hit, after hit of single. Like, no. Those bands are going out and grinding out. Those ones that are good are actually practicing. It’s not so much as just show up and go on for your two hours, and there is your millions of dollars. It’s never that easy, so you’ve got to have some degree of talent, you have to be competent, but you need to put the hard work in.

Stefan Aarnio: Right. You got to respect the grind, so, do you think Jon, this is a question I like to ask a lot of people. There’s the beginner Jon Simcoe, and then there’s Jon Simcoe 2.0 today. Did success change you from point A to point B?

Jon Simcoe: I don’t think a lot of it has really changed fundamentally, and I am pretty much the same guy as before. I’ve never really been without money. I’ve always grinded hard, like university, a job, and the TaeKwonDo club, working lots of hours in Fort Mac, building a business in between all those long shifts at work, to the point where now I am on my own, doing my thing, and have been for almost five years, but I still have to put in my time.
There’s days it can be a little easier than others, but you know, you always need to keep pushing forward if you want to achieve more. There’s never a moment that you can sit back and say, “This is easy. We can relax,” no. You can’t

Stefan Aarnio: Right, so for the kids at home who have the dream of getting rich in real estate and lying on the beach, are you saying that that’s not part of the game? Do you not have any fun lifestyle things you do, or are you just like me and you’re insane, and you’re working, and then you work between your work, and you work two shifts every day, that most guys are doing one shift. Are you just insane, or do you have some lifestyle, too?

Jon Simcoe: I’m doing a little of insanity at time. I think there’s moments when we’re insane, and we got to take moments to like recharge the batteries at the same time. I got a pretty good lifestyle. I try not to share it all the time, because I feel like sometimes people get jealous, and maybe I’m just a little scared of the haters, but I really don’t share half of the cool stuff that I do, which is something I’m going to start doing a little more in the future, because I don’t really care.
I spend my free time driving exotic cars, traveling to lots of different places, and so that is going to be like coming out of my YouTube channel in the future, because I do think that it’s worth it, but we do need to work in between. I got three months of travel planned this year, and that’s something I can afford to do because of my business.

Stefan Aarnio: Right, so that’s what the kids at home want to hear. They want to hear about, oh man, the lifestyle. The lifestyle, the most important thing. You see all these guys on the internet with, “Here is my garage. Here’s my Lamborghini, here’s my lifestyle.”. What do you think about people who are using lifestyle as marketing, or as bait to get people in?

Jon Simcoe: Well, I think that they’re really selling sunshine at that point. It’s not something you can hold, it’s not there. They’re selling like a dream, and people will buy into the dream, especially if it’s like 67 dollars, or 99 bucks, or whatever.

Stefan Aarnio: You mean 67 dollars, we even know [crosstalk 00:10:51], but we’ll talk about this [crosstalk 00:10:52].

Jon Simcoe: Exactly.

Stefan Aarnio: You mean there’s 67 steps?

Jon Simcoe: There is in that program.

Stefan Aarnio: Wow, for the good life.

Jon Simcoe: But it’s like, “We’ll bring you the good life,” that’s right, and that can be good, and you know, I went through that. I thought it was interesting. I wanted to see what he was up to and what everyone was talking about, and 67 dollars didn’t seem like much, but the backend offers and marketing that comes through, that’s just the tripwire of the start, and it’s brilliant to look at it from that standpoint, but you can’t … Like, I don’t think that’s his actual lifestyle all the time, and I don’t think that other people can maintain that all the time, either.
There’s more than just … Like, you can only drive one car at a time. I got four. It’s stupid, and I want another one like I really need one, but you can only drive one at a time, I can see why having 10 there’s no point to it, because there’s already no point to where I’m at right now. He’s got to have whatever, so, it’s nice to have that lifestyle and be able to choose what you want, but it’s nice to use what you got.

Stefan Aarnio: Well, I find it interesting, too. I got this bookshelf behind me, full of books, I got I don’t know how many books. Tons and tons of books. I got 27 suits in my closet, but guess what I wear, my “America” sweater, black V neck every day. That’s my favorite thing to wear. You can only wear one set of clothes, you can drive one car. I like what Warren Buffet says. He says, “Man, my life’s the same as your life, except I travel better,” but he eats the same quarter-pounder with cheese, he eats the same sausage and egg McMuffin, he has the same Dairy Queen ice cream. Everybody’s got the same thing, he just flies private.

Stefan Aarnio: Switching gears again, Jon. Do you think that mastery … I think you’ve reached a degree of mastery in what you do. I don’t know many survivors of rent-to-own in Canada that are crushing it like you are. Do you think mastery is the blend of creativity and discipline, and what do you think is more important, creativity or discipline?

Jon Simcoe: That’s actually a really, really tough question, because mastery does take definitely a lot of discipline. You have to not give up. I think of that like Jon 1.5, like the guy in between who’s like going out trying to raise capital, having overcome those barriers and actually going to talk to people, and like the first 50 people said, “No,” and I kept going because I’ve removed conditions on a deal. I had to keep going. I burned the bridge behind me, I had to keep on going.
I did make it happen, but if it wasn’t for-That was like a breaking point, and I had a business partner with me, and I actually sold half of my company to him after starting the company in a foolish move. I learned a lot of lessons, I bought my half back, it’s my baby now, but during that first acquisition with other people’s money, we’re not using our own anymore, he panicked, he chickened out and he couldn’t do it, and I kept going, and that’s when I bought the company from him and actually carved my own destiny.
I could’ve been like him and said, “Oh, nobody’s going to do this with us. Let’s go tell those sellers that they can have their house back,” you know, but I kept going. And then, when the market changed in rent-to-owns, and Fort McMurray had a big change in 2014, all the rent-to-own companies were going out of busi-Everyone knows how to make money in an up market. That’s the easy thing, but what I’ve had to figure out, and there was moments where like all my passive incomes from my buy and holds-

Stefan Aarnio: The mailbox money.

Jon Simcoe: That’s right. Yeah, like I’m sitting at home in my house coat all day like Hugh Hefner just opening envelopes stuffed with money, right?

Stefan Aarnio: Covered in many beautiful women, right? You’re Hugh Hefner, you got your robe on.

Jon Simcoe: Yeah. You know? Or at least the right one.

Stefan Aarnio: Yeah. I know. You have a girlfriend now. Right, Jon?

Jon Simcoe: Yeah.

Stefan Aarnio: Yeah, okay, so not covered in many beautiful women. Not Hugh Hefner.

Jon Simcoe: That’s what I meant by, “the right one”.

Stefan Aarnio: Committed. Committed, right.

Jon Simcoe: But, yeah, it’s never quite that easy, and what happened to me was my cash flow started drying up and I could no longer do the same rent-to-own trick I was taught in a course, which was a good course, but it wouldn’t work in my market. It worked in other appreciating markets, and now I teach people how to do that, but what I had to do was I put my head down and go, “What am I going to do?,” and I actually figured out how to do sandwich rent-to-own deals, which is just a no-money type-I do a lot of deals where I raise a lot of capital from people. I want to make that clear. When I had to stop buying places in Fort McMurray after 2014, or at least like be very choosy. I need them real cheap or I’m not interested, but at that point I changed.
I was doing rent-to-owns, I stopped buying them for other people, and I started solving all these property sellers’ problems. All these people that were losing their-And, I had to get creative, and I went, “There’s a problem in the market, and I actually know how to solve this,” and none of the other rent-to-own companies did. Most of them are not in business, or doing deals right now, or only have the capacity to do two or three in a year, because they operate in their own levels. And I broke through all those barriers because I refused to give up.

Stefan Aarnio: I love the story, Jon, about the jaws of the market closing in on you and everybody else, and you’re the last man standing. I’ve been through that myself, where I’m the last man standing and flipping, and coaching in Winnipeg. There’s lots of guys who come in, they start something, they sell some packages, they do some flips and then six months, 12 months, 18 months, they’re gone. What makes you different out of all those operators who come in? Why are you the guy who’s still standing and they’re not?

Jon Simcoe: I think it’s because I recognized that there was an opportunity, because at one point I thought rent-to-own was for scumbags. I never used to think it would be like something my parents would be proud of me doing, you know what I mean? Like, being the rent-to-own king.

Stefan Aarnio: Right.

Jon Simcoe: If you’re going to something you might as well do it to the most you can and play full out, but I decided since it’s such a scuzzy industry because it’s true. There’s a lot of failure rate at rent-to-owns. That’s actually a problem that can be solved. I’m going to have to go against what would be considered cool or normal, nobody wants to become the rent-to-own operator when they are a little kid, but by figuring out how to do it and do it right, it sets me apart from everyone else, so if you had to pick a rent-to-own company, I know some other ones that are pretty ethical and good to deal with, and I’ve met them in different cities and I do go around speaking with them, but, and I can, if someone’s in another city, I can tell them who to deal with.
I don’t need all the volume, but I also know that there’s a lot of scumbags out there, and there’s a ton of people you should avoid, and so most people only know about all those horror stories, with the few good ones here and there. Then, if I’m the brightest good story, everyone will come to me.

Stefan Aarnio: You’re the least ugly girl at the ugly content.

Jon Simcoe: That’s right. I may not be doing something super pretty, but I am the most pretty out of them.

Stefan Aarnio: You’re the most pretty out of all the ugly girls. Cool. Jon, what’s more important to you? Having a great brand, or having a great business?

Jon Simcoe: I think you need to have a good business first. The business needs to have good fundamentals behind it. What about you, Stefan? What do you think? Business or brand first?

Stefan Aarnio: Well, I’m a brandpreneur, like I’m brand first, and then attach any number of businesses to a brand. That’s how I am. I think Richard Branson’s like that, but I think there’s guys out there who are hardcore business first, and they might slap a brand on a great business after, so it’s like a pizza, you could eat it crust first, you could eat it cheese first, you know.
I talked to a guy earlier today, Victor Minasce, great developer, he says it’s 50/50 blend in the middle, so everybody’s got an idea, and I guess you’re a business-first-brand-second kind of guy?

Jon Simcoe: Well, I think you need to have-Your business needs to be there. I guess maybe, and maybe you can enlighten me a little bit, Stefan, because I really look up to a lot of the advice you give and when we do have conversations together.
I was growing business Lion Properties, which is my corporation I do the rent-to-owns in, and Lion Properties is one thing, and then, Jon Simcoe is another. We have our corporate, and then we have our person.

Stefan Aarnio: That’s right.

Jon Simcoe: And then I started teaching people how I did these rent-to-owns and why were they all working out when so many other were failing, and teach them just the little tricks I learned over all the years, so then I start doing a bit of coaching between the rent-to-owns. I’ll do a little bit of that. It’s personally self-fulfilling.
It’s fun to teach someone something if they want to learn, but I kind of started realizing that I started separating Lion Properties does deals, Jon Simcoe does coaching, and this is just like more of a revelation in the last maybe six months that I’ve been going through in my head. I don’t know if I can … Maybe I could because Johnson has good rent-to-own deals, but everyone knows me more than they know Lion Properties. There’s no doubt about it.
Stefan Aarnio: Right. My company, I have a corporation called Archangel, and then there’s Stefan Aarnio, and then I have Help Home Ventures, or Stefan, so I have these corps. One of my coaches and mentors back in the day said, “Build your brand, build your personal brand, and then the other businesses, they attach on to that.”. That’s what I’ve always thought, and I guess you’re reaching that similar kind of pattern where it’s like you have the brand, you build the brand, and then attach other things to it, or do you take a business that’s just running and making cash, and brand it?
I guess there’s two ways of doing it. I’m a brand guy because to me, my brand is a better asset than any of my real estate. It’s a better asset than any of my businesses because my brand can literally pull money out of thin air, because I built it that way, but everybody’s different with it.

Jon Simcoe: I definitely respect how large you’ve been able to grow in the last … Well, I mean, I remember when we first met a long time ago, Stefan, it’s like amazing to see everything that you’ve done and the path that you’re on.

Stefan Aarnio: Thank you. Yeah, I think, we met, I was trying to buy a property from you. You were a seller and I was buyer, and I was trying to buy too low, and your price, you wanted to sell too high, so we never did a deal.

Jon Simcoe: That’s right. That’s right, and that was on one of the Winnipeg houses that I’d gotten seller financing. I actually remember the deal. I’d gotten seller financing within about less than two years of you calling me, so I’d freshly picked this place up, and I owed fairly close to market value, but I figured that was a safe move in Winnipeg considering I’d just got seller financing on this whole thing. It never made a ton of money. Its repairs and expenses just broke even the whole time I had it.
Obviously it went up the way Winnipeg does over time, but you called me wanting to buy it from me for like 40 cents on the dollar, which I know is something you teach everyone how to do, and I’m thinking to myself-

Stefan Aarnio: That’s how I make my living, man, come on.

Jon Simcoe: I can’t sell. I can’t even sell it at 90 cents on the dollar because of what I’m into it for. This is a long-term, no-money-in deal that I figured I would make, because I was like still starting out at that time, and so I never did sell you the house, there was no way I could.

Stefan Aarnio: Right. Right. Switching gears, Jon. Everybody who’s a top performer like yourself has an obsession. What’s Jon Simcoe’s obsession?

Jon Simcoe: Me? I just try, I try all the time to do things as best as possible. I strive for perfection in what I’m doing. I would like to get more cars. Jon Simcoe owes his eight-year-old self a Ferrari, and I’m on that path and that mission. It’s not only to get a Ferrari, but it’s [inaudible 00:23:56] to regularly drive it around, not to be a guy who’s only got it parked in their garage. I want the lifestyle of having a Ferrari, not a Ferrari in the garage to talk about my lifestyle.

Stefan Aarnio: You’re in my garage.

Jon Simcoe: Yeah, you know, and I learned something because when I was, actually, that’s when I was about eight years old I’d saved up, and this is like the act of saving for something you want. I saved up three frosted flakes like UPC codes, and cut them out, and mailed away for this Ferrari car. Actually, I think it’s here in my office because I still have it, because it’s a goal, and I want it. I showed my dad when I was little, I said, “Look at this car,” and he said, “Oh, you better start saving,” and that’s the instant I became a saver, like programmed.
I became a saver at that moment, and started working hard, “I’m going to get this,” but then I learned in my adult life that in order for me to actually achieve becoming a Ferrari owner and driver, and someone of that stature, is that it actually is not for like a trashy-type person.
I mean you can be rich, and trashy, and own one, but the true type of person who can afford to own a machine like that, is not a man who goes to a job and saves up money. A man who does other things in his life in order to have that be in his life, and so I knew that I had to change who I was if I was ever going to achieve that.

Stefan Aarnio: You talked about being great there, Jon, and always wanting to be great and do things great. What motivated you to be great to do what you do? Is it the Ferrari, or is it something else?

Jon Simcoe: I think it’s the personal satisfaction of serving. Like, you know, you become leaders and often are. Go, go.
Sorry about that. Dog came in.

Stefan Aarnio: Cool. It’s not your two babies and your wife, like that one guy on the spoof?

Jon Simcoe: Oh, like, “Oh, honey! We need you!”.

Stefan Aarnio: Yeah. Nevermind.

Jon Simcoe: No, if he wants out I’ll let him out after. He has to go out. This is like an interesting thing about conditioning, which is just a total side rant, but maybe totally relevant to this. This dog got conditioned at a young age that when it came in, it would go to its bed, and then it would have a treat there; and so now, this dog asks to go outside because it thinks when it comes inside there’s going to be a treat there, when there’s not been a treat there for six years.
And so, every hour or two, it asks to go outside only for that. When it’s really cold outside and it doesn’t want to go outside, that dog will stay inside for days without going out. It does not need to go outside.

Stefan Aarnio: Oh, man.

Jon Simcoe: But it’s an interesting thing of the conditioning. He thinks, every time he goes to the bed to look for that. Every time.

Stefan Aarnio: Jon, how does that play in to … You know, the dog’s conditioning, how does that play in to you and how you’ve conditioned yourself?

Jon Simcoe: It comes down to regular habits, and what you do on a daily basis. Every little thing adds up. There’s a word called “cumulative” everything adds, adds with it, so whether you’re focusing your mind, like, I would use to spend an hour if not more every day waking up before my shift work to work on my real estate business, to write newsletters, to create some content, to engage the people I met when I was networking. All those sorts of things when you’re grinding it out.
I got up an extra hour early, on top of a 15-hour work day, and then when I got home I stayed up an extra hour late, and then on the days off, which were all spent working and grinding it out, too. And that’s a discipline habit of filling my day with work, from start to finish, and by being used to that my day becomes full. I don’t mind. I don’t feel worn out after an eight-hour day, I don’t know about you, Stefan, I know you put long hours in. You’re conditioned for it. You can take it. You can grind it out.

Stefan Aarnio: Right. Well, you know what, I did some analysis, I was writing my fifth book “Hard Times Create Strong Men,” and I realized I’d been working at least two work days every day for the last ten years, and when I got into real estate I had four jobs, man. It was wake up at 4AM, put chips on shelves, Frito-Lay, Doritos, and Lay’s till noon. Then noon till 4 or 5 was real estate, then after that was guitar teaching, then after that was my debt-buying business, and then I would crash, sleep at my girlfriends house or whatever, wake up and just do that. I did that for six months, and I think I was almost dead at the end, but that’s what it takes, man.
I love hearing the stories about waking up an hour earlier, going to bed an hour later, you got the 15-hour workday, you got the business, you got school. Now, here’s a question for you, Jon, with the business and the school. I talk to a lot of young people and they say, “But I’m a student. I can’t do that, I’m a student. I have an exam coming up.”. Now, what do you think young people need to succeed these days?

Jon Simcoe: I think what they need is they need to actually have the discipline to put in that time. I set aside like a couple evenings every night, every week, for five entire years to grow that TaeKwonDo business. I didn’t have to be there all the time. The risk was like small to get it started, I figured if I didn’t sell a lot of lessons, I would have to pay rent and give my time to these kids, and adults that are coming to learn, and if I sold well, I could eventually hire some other kid who got his black belt, which I did in year three, but I figured the risk was small to try it out.
It was something that I’d already been paying to do before, that I really enjoyed, and already was putting the time aside. I just was able to monetize it, and then I had so much fun with it. I really enjoyed, that’s where I learned that I loved serving a client. Like serving a parent who’s dropped their bratty kid off so you can teach him a lesson, and I mean that not in a punishment, physical way, but I mean actually teach them discipline and just the exercises you grind through. They will improve. It doesn’t matter if you end, so, having a parent say, “Oh, thank you,” or, “He’s not a problem in school anymore,” just by instilling discipline and perseverance in those young minds. It’s very personally satisfying.

Stefan Aarnio: Jon, with that, what do you think causes most people to fail?

Jon Simcoe: I think it’s because in most days, most people in today’s society, they really want that instant gratification. I want my double Big Mac and I want it now.

Stefan Aarnio: Double Big Mac with bacon?

Jon Simcoe: Yeah. Add extra sauce, you know? Load it up, load it up. But like, “But we want it now,” and like I don’t even-I made a custom order, but I can’t wait for it to come through the assembly line. You know, people want it now, and that’s actually a huge problem, and so I had something that I always thought I would … I always think this to myself, “My future self will thank my present self for what I’m doing today,” and that’s something I’ve thought ever since being like a teenage boy, when I was a saver, “I’m going to have this money later. I’m going to thank myself for saving.”.
I look back on it and how much easier it is to make money than when I was 12 doing landscaping and breaking my back. How much easier it is now, and I go, “Man, I really didn’t need to work that hard,” but it’s by working that hard that gets you here, and by having that drive.

Stefan Aarnio: Jon, in this process of working that hard, what was a moment were you thought you’d fail?

Jon Simcoe: There’s many times, actually, like with the TaeKwonDo club. I thought I might fail, I thought maybe people wouldn’t come out, but I thought, “What would be the worst case scenario if nobody came out to my lessons?,” and the worst case scenario wasn’t that bad, so I went for it. When I moved to a new city, to Fort McMurray, I was just a young man, I’d paid off my student debt and I had one rental property, and I split town.
I rented it out. I had no manager, or a really well-thought-out plan with that property, and I left town to go pursue other things, and I had a good, I had a city of Winnipeg job, so for those who know what it is, all my friends around me thought I had like, I was a foreman at the city and they thought that I had the most golden, cushiest job, and I’ll tell you if you work too hard your coworkers will hate you because you’re making them look bad. That’s not the kind I am on the inside, and I just, I don’t want to trash-talk my old comrades, but I’m used to working a lot harder than that and knew that I couldn’t stay, but I took a leave of absence.
I had a whole year to try Fort McMurray, so the risk there again was small. Why not go for it? If the risk is like cataclysmic failure, and you’re going bankrupt or you’re going to die, like maybe jumping out of that plane without a parachute is not a good idea. Maybe that’s just suicide, but if you can think it out maybe you can jump out of that plane, if you do have a parachute, and if it’s got a backup chute and you feel pretty good, you’re probably going to make it to the ground.
By minimizing the chance of failure, and having a really, really high, like shoot-for-the-stars outlook, you really can’t lose. The work you do is so small, if you achieve half of what you’re shooting for, it’s like if you did that, one out of ten times achieved it, so that nine times you fail, your one out of ten success is going to trump all those failures big time, and so it’s worth going for it every time.

Stefan Aarnio: Now, when you were getting into it Jon, did other people doubt you? Did they say, “Oh, Jon Simcoe. It’s never going to work. You’re never going to have it.”? Did you lose friends? Did you lose family members? Were people hating on you?

Jon Simcoe: Absolutely. A lot of that can happen, but you have to tell yourself, and not even really tell yourself, but you just have to come to the realization that those nay-sayers, they’re not on your side, so who cares what they think?
Stefan Aarnio: Yeah. I like that. And, if you can go back to the beginning, Jon, you know, 18-year-old Jon Simcoe, you’re an established man now, if you were to go back to 18-year-old Jon, what would you say to him?

Jon Simcoe: I would tell me to keep working, and that your future self will thank your younger self for what you’re doing right now. I might tell myself that, “Hey, stop and smell the roses a little bit. Not too much, but maybe a little bit more than you did, and enjoy some of that time.”. Don’t worry, I had fun, but I did work two or three jobs every summer, and I know you get the picture. Every hour was fun. I would take a moment to enjoy it a little bit, but you can’t only live for those enjoyable moments. You just have to make a little bit of time for them, and still go do them.
Hang out with really good quality people. The five people you have around you, you’ll be the average of them, so go get some cool people to hang out with, you know, if you hang out with some rich friends, you’ll become rich. It’s just what happens. If you hang out with a bunch of people who eat McDonald’s guess what? You’re going through the drive-through, too.

Stefan Aarnio: Love it.

Stefan Aarnio: Jon, top three books that changed your life.

Jon Simcoe: I would have to say, well, I think there’s a theme there that Rich Dad, Poor Dad did change my life a lot. I’m going to have to say another one that changed my life a lot was a rent-to-own book. It was one by Mark Loeffler, he had written it, and when I read that I thought, “Wow! I think I could really get in,” what I learned was I tried to do a deal with only the book and realized I needed a proper course and a coach, but I hired one later and got better. And then, the third one is the Money People Deal book that you wrote. I know it’s also, it’s also Five Million Dollar Book.
I was just with Dave Dubeau in Vancouver. I was helping him out with one of his events a little bit, and he’s teaching people a little bit how to pitch to get money partners to do their deals, and he’s like taking that money people deal, like he’s running with that stuff, and he’s got a few slides, and he says, “This is what Stefan Aarnio says,” and he goes-

Stefan Aarnio: Oh, man.

Jon Simcoe: Oh, yeah, and it really works good, and by actually being able to do that, because I used to give too much of my deals away, as well, and it’s okay to be generous, but you can’t work for free either, and so that Money People Deal allowed me to basically do better at something I was already doing. Everything I did was already being improved because of that book.

Stefan Aarnio: Awesome, man. I appreciate that. We’re in the third edition now. In the last two years, I found out we just sold 7,000 copies, one at a time on the internet, which is crazy, so a third edition going back to the Money People Deal title, because that’s the original, man. Money People Deal. I appreciate you.
How much money do you think you’ve raised? Did you say 10 million last time I spoke to you from use of that concept?

Jon Simcoe: From that concept, it’s more and more all the time. We’re probably up to about 12 or 14 from it.

Stefan Aarnio: Wow.

Jon Simcoe: Whether I use it or not, I deploy it, when appropriate, when we’re doing our sales meeting and we’re deciding whether or not this person is going to come do a deal or not with us, or whether we want to work with them or scrutinizing them, the majority of the time I’ll pull it out, because it makes sense, and then, the other thing that I like to do-I do a little enhancement, or a little Jon Simcoe version of me.
I’ll run it by you, see what you think of it, so what I’ll do is I’ll say to them, “So, if you’re interested, you have to let me know, because this is a first-come, first-serve basis, and I have no doubt that as soon as I send an email out to my list, this deal will be funded, but I do need to know by a certain amount of time, so,” that’s if they’re going to be leaving without having made a commitment on the spot, or maybe they’re expecting me to email them something, and then they’ll say, “Yes,” but, you know, I put that little bit of pressure out there because it’s something that you’ve taught, as well.
I’ve seen your presentations several times, and every time I have a new takeaway. One of those takeaways was that money doesn’t need you as much, and so, I think back on that Jon 1.5, where I chased, I counted over 50 people that all said, “No,” the first people I asked. And, it’s because I was, from an act of desperation, I removed conditions on this deal, and I felt like I had to get it done. I promised this family a rent-to-own house, like I promised them. Now, all of a sudden I’m not going to be a man of my word. That hurts.
For someone who’s done so much martial arts and instills integrity and perseverance into other people, I cannot live with myself. I must keep going.

Stefan Aarnio: I love that. Jon, switching gears again, who’s your most important mentor and what did you learn from that mentor?

Jon Simcoe: The most important is actually a guy named Brice. Not your Brice, that works with you Stefan, although shout out to Brice, he is awesome at what he does; but, this other guy, he came to me and we had a little conversation. This guy owns many buildings. He’s probably not who we’re thinking about. Brice is his real name, and he said to me, and this guy, I didn’t know much about him, I just knew that he was a rich guy, and he says to me, “You know, Jon. How many deals is enough deals for you?”.
He looks at me as like a younger version of himself, I’m putting deals together, and that’s what he used to do, and now he’s an old man … But, looks at me and he says, “Jon, when’s it enough? When’s it enough money? When’s it enough deals?,” and I looked at him and I said, “It’s never enough. There’s always another one. We can go do more. We can make it happen,” and he said, “Wrong.”.
He said, “What you just described to me is the behavior of an addict.”. Oh. A money addict, a deal addict. There’s a little bit of a thrill like a hunter on the chase. There can be some fun to it, like I know we need to keep our emotions cool, but there’s a satisfaction when that deal is inked and you know it’s happening like, doesn’t that feel good? It’s a good feeling.

Stefan Aarnio: Oh, dude, look at me. I’m addicted. I’m addicted, man.

Jon Simcoe: Addicted to deals.

Stefan Aarnio: Yeah.

Jon Simcoe: And so I thought, “Okay,” then he said, and so he again gave me some advice after that, being his response, and he said, “You know, Jon. I’ve sponsored over 100 foster children throughout my life,” and I went, “Really?” I had no clue he had done that, and he said, “You want to know why?,” and I said, “Well, yeah,” and he said, “Just because your charity, your this, your that,” he says, “Well, like I feel for the kids,” but when he’s done at the Country Club, or seeing his other friends, he likes to talk about money.
He loves it. We like to talk about money, and he likes to talk about money with his friends, and he likes to talk about the next deal, and all that, everything that’s going on because he’s the same way. And he said, “You know, at least when you’re visiting your friends and you’re talking about money, they’re not going to say, ‘There’s that Jon Simcoe,’ or ‘There’s that Stefan Aarnio asshole, who all he does is talk about money,’ they’ll say, ‘Oh, there he is talking about money again, but he does so much good stuff, so hey,’ and then they don’t seem to mind anymore,” so that was some of the advice that he had given me. I just thought it was kind of funny and applicable at the time, for sure.

Stefan Aarnio: So what do you do to give back, Jon?

Jon Simcoe: What I like to do, actually, I support a whole bunch of kids’ basketball programs here in Fort McMurray, mainly because I really like the basketball coach, and I like what he’s doing. More so, I sucked at basketball, I never made the team, that is not my sport. Martial arts was my thing, but other sports, throwing a ball, that is not my coordination. Puck handling and Hockey that’s not my skillset, but I like the coach and what he does for the community, and so I sponsor that because I do a lot of rent-to-own deals, and so if I’m making a whole ton of money, and getting rich or as people see it, however they want to perceive it, I’m taking my cake.
At least, if I’m giving back to the community, and sponsoring the same kids, who are likely growing up in these rent-to-own homes, like sports team, am I that much of an asshole at that point?

Stefan Aarnio: Mm-hmm (affirmative)-

Jon Simcoe: I support Dan Briscoe and his Aurora Basketball, his whole program.

Stefan Aarnio: Cool. Well, I like it when guys are doing something local, that’s really special. Two more questions before we go, Jon. We got to wrap it up. Are there any resources you recommend for people starting out who want to get into the Jon Simcoe lifestyle like you?

Jon Simcoe: Absolutely. There are some resources, I just created a new training portal. I don’t know if you’ve seen it or not before, Stefan, but it’s www.jonsimcoe.com, that’s J-O-N-S-I-M-C-O-E.com, and what I did is I made a training course that’s about to get some massive updates, where I’m going to teach a lot more of no-money real estate deals doing rent-to-owns, but for the more traditional type I created a course a long time ago and I’ve been polishing it up. It’s looking a lot better. It’s up there. That’s something that people can buy if they want to learn how to do rent-to-own deals.
It’s 1,000 bucks. Otherwise, I have some free videos there, but as everyone knows, like all things in life, nothing is for free. You will watch those videos, you will definitely learn a lot more about what a rent-to-own deal is. Like that book that I first read, it’s never as good as taking an actual course, so if you want to just get your toes wet, get the free training, if you’re ready for the full course just go there and pick it up, and then I’ll be in touch with you, we’ll talk after that.

Stefan Aarnio: Can you spell the URL for people at home? I’ll just try typing it in while we’re talking here.

Jon Simcoe: Www.jon spelled J-O-N, then Simcoe, S-I-M-C-O-E.com.

Stefan Aarnio: Okay, jonsimcoe.com, awesome. Great, well, the site looks great, so that’s J-O-N-S-I-M-C-O-E.com, and you know, Jon. I’ve known him for a long time, we were mentioning that at the beginning, before we started recording. We’ve been good friends for a long time. Really, really excited to see him grow, to see him prosper over the years, and any final words, Jon, for the people at home?

Jon Simcoe: I just want to say make sure that every day you’re using your tenets of TaeKwonDo, your courtesy, your integrity, your perseverance, your self-control, and your indomitable spirit; if you’re at least doing those five things, you’re going to do well in life.

Stefan Aarnio: Wow. I love that. Respect The Grind, ladies and gentlemen. Thanks, Jon. Good to see you out today.

Jon Simcoe: Good seeing you, too, Stefan. Thanks for having me.

Stefan Aarnio: Hey, it’s Stefan Aarnio here. Thank you for listening to another episode of my podcast, Respect The Grind. Now, if you liked the content on this podcast today, you are going to love my new book Hard Times Create Strong Men, that we live in an age right now where the men have become weak, society has become weak, the mindset has become weak.
What does it mean to be a man? Now, whether you’re a man or a woman, you’re going to find value in this book: Hard Times Create Strong Men, which reveal the philosophy and the power of what it takes to be strong in today’s market economy.
Go ahead and get a copy of Hard Times Create Strong Men at hardtimesstrongmen.com/podcast. That’s going to give you a special offer just for podcast listeners. That’s hardtimesstrongmen.com/podcast. Get the book, you’re going to love it. It’s going to change the way you think. I’m Stefan Aarnio, Respect The Grind. We’ll see you on the next episode.