Episode 31: Jordan Silvester | Cracking the Success Vault Podcast with Spectre Group

In this episode of Cracking the Success Vault, Sean Penhale sits down with Jordan Silvester, real estate investor and entrepreneur, to unpack a journey shaped by market crashes, hard financial lessons, and a powerful spiritual transformation.

Jordan shares what it was like entering real estate during the 2008 market crash, navigating major losses, and learning firsthand the risks of leverage and lack of diversification. From early wins to significant setbacks, this conversation offers a raw and honest look at what it takes to survive and grow in an unpredictable market.

But this episode goes deeper than real estate.

Jordan opens up about a shift in perspective that changed everything — moving from chasing traditional success to pursuing purpose, faith, and fulfillment. He explains how surrendering control, embracing spiritual growth, and redefining success transformed both his life and business.

In this episode, you’ll learn:
 • The dangers of overleveraging in real estate
 • Why diversification and risk management matter
 • Lessons from the 2008 crash and recent market corrections
 • How failure can become your greatest teacher
 • The difference between worldly success and true fulfillment
 • How spiritual growth can reshape your approach to business and life

If you’re an entrepreneur, investor, or someone navigating setbacks, this episode delivers both practical insight and a deeper perspective on what success really means.

🔑 Topics Covered

🏠 Real estate investing and market cycles
📉 Lessons from the 2008 crash and market downturns
⚖️ Risk management and diversification
🧠 Personal development through failure
🙏 Spiritual growth and purpose-driven living
🎯 Redefining success beyond money

⏱ Chapters

00:00 – Market Lessons from the 2008 Crash
02:16 – Jordan’s Background and Entry into Real Estate
04:23 – Values and Helping Clients
06:51 – Working with Family and Business Evolution
08:48 – Professionalism and Authenticity
11:37 – Starting During a Market Crash
14:02 – Learning in a Difficult Market
17:33 – Mentorship and Skill Development
19:00 – First Investment Property
23:15 – Portfolio Impact from Market Drop
24:41 – Leverage and Market Cycles
28:55 – Overleveraging and 2022 Correction
35:37 – Mindset Shifts and Learning from Mistakes
38:38 – Spiritual Transformation
43:11 – Entering Bible College
45:29 – Trusting the Process
48:03 – Service, Giving, and Purpose

Transcript

SPEAKER_04 0:00

Gonna take the real estate courses, okay. After that, then go shadow a real realtor for a month and and find one in your office or wherever you're gonna think, but just find someone you can watch do the business because the business in the book and the business in reality, people don't fit into these simple molds. You can say there's how many personality types, but every single personality you run into is an is a variant of that. And so it was crazy. We went from 721 down to 485. Yeah. Wow. And then bounce back up to about 515. We reached back up to about 600. But like the issue is you're talking in real time, I've got 1% leverage cash on 4 million. That's not a little bit of money. So 1% per month, 12, you know, 12%. Yeah, it was uh it was a moment crazy. I didn't consider that if a deal went bad, let's say I did tap for 50 or 100 grand because the deal just goes bad, I would just tap an asset to pay for it because I didn't consider that all of them, all my personal wealth, which was tied up in real estate, and all my leveraged wealth, which was playing in real estate, would all lose its value simultaneously.

SPEAKER_01 0:58

That Jordan Sylvester has been a trusted name in Windsor Essex Real Estate since 2007. More than just one of the region's top realtors, he's known for a relationship-first approach, helping clients navigate all stages of life from purchasing their first home to managing major life transitions. Jordan is redefining trust in real estate and beyond with his authentic, down-to-earth style. Welcome back to another episode of Cracking the Success Vault with Spectre Group. Today, uh our guest, Jordan Sylvester. Hey, real estate. Um fantastic. How are you? Good, man. Good. So all I know about you, uh, real estate professional, you had some social media stuff going, which we just talked a little bit about, uh, you know, finished your season and taking a little bit of break from it. But I don't actually know your story. I know a little bit here and there from some people I've talked to. But let's share with the audience a little bit about your story, sort of where you grew up, how you grew up, and then we'll get into some sort of nitty-ritty stuff.

SPEAKER_04 1:58

Sounds good. Yeah. So my name's Jordan Sylvester for all of you out there. Uh, I grew up actually, I was born in Sarnia. I was there till I was eight, moved to Windsor in '92. So been here pretty much ever since, except for a stint in Toronto in my teen years. Um, so for me, yeah, grew up, uh, I would call it normal for the most part. When we moved to Windsor, kind of made some friends, went to grade school, high school, uh, went to Kennedy Collegiate. That was uh, I was more interested in the social realities of school than ever the educational side. So being in class was always kind of you know optional in my mind. It wasn't so optional for the teachers, but yeah, you know, that was kind of how that went through. Um, sports uh in high school, uh football, wrestling, uh track and field.

unknown 2:40

Okay.

SPEAKER_04 2:40

Um, those were things that kind of kept me kind of busy. Got a little bit older, uh, didn't go to college right out of high school, kind of uh figured out work for a bit um after that, and then ended up going to Bible college for a year. Um, that was actually in um Brampton, which took me to Toronto. And so I was up in Toronto uh for a year, and then I stayed after. And so up there, got to work um at a place called Woodlore, which is where you put edging on the side of furniture. So ran a lathe for a year and a half on midnights. That was mind-numbingly um, you know, basically like, no, I'm not doing this for the rest of my life. Called my parents, said, Hey, can I come back home? They said, Yeah. Came back to Windsor, got a job working at uh Liquidation World to help build it. Um, and then uh met a girl there, moved back to Toronto with her, worked for Rogers. Um, that didn't work out as well. Uh it was so expensive to be in Toronto, and I couldn't really, without any education, wasn't practical. So looked at an opportunity to do real estate. My dad, of course, at that time had been a realtor for almost 20 years. Um, so I reached out to him saying, Hey, I'm thinking about doing the real estate thing. We met for lunch in London and then uh came back to work for him. I've been doing that for 18 years.

SPEAKER_01 3:49

Crazy. Yeah. So what made you want to get into the real estate world?

SPEAKER_04 3:53

So I was doing so I I actually really liked working for Rogers, but the problem was I wasn't a great salesman because they were pressure sailing. And for me, it was always like, if this makes sense for you, then you should buy it. But if it doesn't, then don't, right? Like, if I'm not gonna have an elderly couple change to say$5 a month when I know it's gonna be a headache to go through all the process, all their channels will change, all that stuff. And so for me, the issue is my team did really well, but they were always confused why I wasn't like my team because I was a leader. Uh, was great at training and those guys would sell really well, but I would spend like an hour with this old couple working through something and wouldn't even make money. I'd just let them like let them go on their way or fix something or do some stuff. Um, it's just been my nature. And so, real estate, the cool part about it versus most other sales jobs is there are those that sell in my business, but really I just help people do what they want to do. My job as a realtor isn't to force someone to buy a house, it's hard to do that anyway. You need to spend, you know, a few hundred thousand dollars and buy a house. Like you can't really pressure sale real estate to some extent. So all I do is show up to help. And so for me, that was what kind of drew me towards the job. Um, you know, I like my dad had done it for years, so I kind of understood the benefits and disadvantages, the freedom of real estate, which is a funny term in some respects because you work 24-7, but you're somehow free.

SPEAKER_01 5:06

Yeah, I mean, yeah, I mean, financial services is no different, right? I mean, uh clients can always reach me anytime. My phone is always on. Um, we have to be like that, but at the same time, there's some freedom, right? You know, not you're not punching in, punching out on a clock, paid for your time. Right. You're you're you know, you're paid for your well, uh your your service, you're paid for how well you can do your job, um, helping people, which is the same with real estate. So, okay, so moved around a little bit. Um and so real estate was attractive from the sense of you could get into sales, but you weren't forcing sales, right? Which is I I agree with that. Um and is that something that uh your sort of mentor taught you in that sense? Did you spend a lot of time with him that way?

SPEAKER_04 6:02

With my dad. More or less when I like we met for lunch, he kind of told me what the business was. Um, because again, I think a lot of people think real estate is is selling houses. Really, it's it's helping, it's more counseling than it is selling houses, right? It's similar again, the financial services. You're spending time dealing with people on an emotional level, you're talking about their retirement, you're talking about how they're gonna provide for their kids and their families. Like um, there is a sales aspect to it, but again, you're dealing in my world, you're dealing with death, divorce, you're dealing with people and some, you know, brand new young couple getting married, like all the emotions that are going on. And so, again, I think that was really where I didn't understand that when I first stepped in. That's where my dad would have taught me more. I understood kind of the the functional side and the helping people. I didn't understand the counseling people.

SPEAKER_01 6:51

Interesting. And so you and you you've spent the last 18 years working with your dad still. So he's retired. Okay.

SPEAKER_04 6:58

So he's been retired since 21. So I guess that's four or five years ago now. We're 26, right?

SPEAKER_01 7:02

So yeah, but that that whole time though, 15 years or 15 years, yeah. Me and my dad worked together.

SPEAKER_04 7:07

Never strayed, hey? Nope. We worked together the whole time.

SPEAKER_01 7:10

Um, I don't know if I could work with my father.

SPEAKER_04 7:13

There were days, so so we we found a good way to manage. Basically, he allowed me a lot of flexibility. He had his moments where he would push on certain things and I'd push on certain things, so it wasn't always perfect, but I would say on the overall, like we we have a good relationship. Um, you know, he he was much more let's be in the office 24-7. I was much more let's be out talking to people and doing stuff. And so again, that was a little bit like again, I think when he started in the business, it was like you were in the office, like it was a normal office job. It was a much different world in '88 when he started compared to 08 when I started.

SPEAKER_03 7:48

Yeah.

SPEAKER_04 7:48

Um, and so I think with that, there's just different expectations. So I slowly, you know, I dress the way I dress. This is how you'll meet me, no matter kind of where I'm at. Um, unless there's a gala where my wife makes me dress up, then that, but you you see me in the day-to-day world, I'm in my shorts, t-shirt, sandals, that's my summer attire. Um, you know, might be coming right off a golf course. But for me, life is about, you know, um flexibility and comfortability. It's not that I I also believe in professionalism. I'm not like, I just think the way I dress, if if that's very important to someone, that's okay. But for me, I use my intellect, I use my conversational style. You know, I find, especially where we we live in Windsor, um a more blue-collar town, you know, people expect to meet, you know, someone who looks like them. If I go out to a bar, I don't see a bunch of people in suits there.

SPEAKER_03 8:34

Right.

SPEAKER_04 8:34

Right. If I go out and I'm and I'm just at Timmy's, is again the same thing. Whereas I think if you're in Toronto or other markets, then it's a little bit different. And I'm not everyone has their thing. I know some people who put on the the stuff because that's how they feel a certain way.

SPEAKER_01 8:47

This is how I it's their armor per se from uh from a uh a career or sales perspective. If they're not dressed the part, then they can't act the part.

SPEAKER_04 8:57

Yeah, for six months I basically put on a suit almost every day to work for Rogers. And I I love the days where we would go door knocking because those days um I could put on more like slacks and like a polo, golf shirt or something, golf shirt or something. And so for me, like having to put a suit on every day to go stand in a store to talk to people who are coming, like to me, that was just that was their policy, so I did it. Yeah, but uh got me to the point where I kind of was like, nah, I'm just I don't like I don't like the stuffiness of that. That's me, right? Yeah, like I said.

SPEAKER_01 9:24

So is that something you learned then from your father? Because uh obviously growing up with him being in real estate, you're seeing you know, the professionalism, you're seeing all this stuff. Um obviously you must have had some like drive and I want more out of life. Is it because you saw what your dad was doing? Or is it something that you kind of learned or created on your own because you just wanted to do things differently?

SPEAKER_04 9:54

Probably more that I'm I tend to just go against the grain. So so my personality likes to see how other people do things and then see if I can do it differently better, as I would call it, right? But but it's not necessarily better, it's just my way. Yeah. So in my own mind, when I was young, of course, my way was the better way. Um, and so in a lot of ways in the real estate world, like one of the the things that was interesting was my dad was very much into um paper media, right? Everything was in in magazines and then doing the the the channel on television and having all your listings there. And I'm like, at some point the internet was out, and like we need to start transitioning away from one and going towards the other, but it's how he did but had done business by then for almost 25 years. Yeah. So again, there was a little bit of push and pull, and and I was the one that generally tried to lead us into you know the 21st century and out of the 20th century. Yeah, um, and so with that, like again, the dress code and that that would be me just kind of balking, even at what I would consider the status quo. Some of it is probably just a desire to be different and not have to conform. Um, so that's that's really one of my my dad's much more desire, like not to fit in per se, but just he's more willing to accommodate what would be the norm.

SPEAKER_01 11:08

Yeah. Okay, yeah. I I can understand that. I mean, I I think anytime my dad says something, I always go against it. I think it's just more of a father-son thing, right? Gonna do it your own way, figure out a different way, better way. Yeah. Um interesting. So tell me a little bit about then starting real estate in 2008. Obviously, the market crashes, everybody knows what happened. I got started in finance in I want to say 2011. I believe it was late 2011. Uh, I think it was like October sometime. Um and for the market had already kind of recovered by then from the investment perspective. Um but in Calgary, oil and gas had some tough times in late 11, 13, and a couple other years, right? So um what was it like getting into a business like real estate selling homes during a period of time basically where the last 12 months was complete and utter chaos?

SPEAKER_04 12:17

Yeah, one of the interesting things about jumping in there is I didn't know any better. So so I think one of the benefits of cutting your teeth in a hard market is you don't know what a good market is. Um, my dad at the time had um we had a bank contract with MCAP and Exceed Mortgages. So we were able to that's where I really cut my teeth, was doing a lot of paperwork. Um, so you know, current market analysis, that's why I can do them so fast now today, probably, is because like I can just pull data like nothing because I had to do so many because we'd have 35, 40 listings on the go um back then, because basically you listed something and it would be on the market for three to six months, right? We we've been in a world, even in this market where stuff still usually sells in about 21 days or it generally doesn't because the price is wrong. Um, even but the 08 market, we carried tons and tons of inventory. Um, and so for me that was normal. I didn't know it was a bad market per se. The the toughest thing I will say about learning there versus when it did get better was that I didn't have to have conversations with like, how do we actually get you out of your home?

SPEAKER_03 13:19

Right?

SPEAKER_04 13:19

Like you're underwater, you don't have enough money, we've got to pay the realtors, we've got to pay the lawyers, we've got to pay the mortgage off, we've got to figure out how you guys get out with your shirt on. Um, those conversations were nice to avoid for a bit. We've had a little bit of that again, repeating over the last couple of years, where people are in spots again where you're kind of like, hmm, yeah, and they say there's a 17-year cycle. Well, 08, 2025, kind of there's your 17 years. So again, it's interesting to watch, but I'm grateful for it because I think anyone who's getting into the business today is getting the same benefit. They don't know any better. So this is if you I always tell people if they're new to the business now, I'm like, if you learn to do it today, I promise you, this is this is the hardest market you deal with. Right.

SPEAKER_01 14:02

Interesting. And so what was that? Did your dad just like throw you in and just like, here, go train, here's what you got to do? Like, obviously, training nowadays, I mean, everybody's got training platforms and everybody's got sales training and coaching training and sales meetings and all that kind of stuff. But like, you know, in the 08, I'm sure it wasn't like it is today. Right.

SPEAKER_04 14:24

Yeah. So when I when I first jumped in, uh, so I started working for him as an admin assistant in 07, May of 07. So I was licensed in March of 08. Um, so again, I was just doing CMAs because I could. Like, so he taught me kind of the background paperwork, all that stuff. So when I went to take the classes for school, I had a much more knowledge than a lot of the kids, and even some of the people teaching, because again, we were doing close to you know 70 to 100 transactions a year. Yeah, so just the amount of times I had done certain things and stuff. So in class, I remember one of the teachers talking about like the bank repo situation. I'm like, that's not that's not how that works. That's not how that works. Not not in not in not in my day-to-day. So I don't know if it works different in London because I was taking the course up there. But you know, anyway, me being yeah, smart.

SPEAKER_01 15:08

I mean, listen, that's part of uh uh being taught a business course or being taught a realtor course by somebody who actually isn't a business person or isn't a realtor. Right. Yeah, they have a license and yeah, they can teach the course, but they've actually never done the job. That's what I had a hard time with in school was taking business classes and you're taking like consumer behavior and um you know how to like actually build a business and how to market the business and what colors you should use and music you should use and where you should put your building and like you know, figuring out the best place in the city for it, like all these things, and like that's great in practicality, right? But like when you do your market research and it's like okay, your best location is here, and then you go and you look at that location and you're like that's a Tim Hortons or that's a Starbucks, they're not giving you that up, right? Right, like you have to go put your building or your your business where you can put your business, right? We're not sinking millions of dollars into some place we don't know, right, right. We gotta put it there and we gotta do the best we can with it, right? We gotta market, we gotta do things, we gotta attract other people to our business, but it's never like real life is never the way they teach it in school or in courses, right?

SPEAKER_04 16:26

Yeah, the life in in again, it's interesting because those who make policies don't know what the policies even do. Um, one of the things that was most interesting, my mom is an RN nurse, and uh, as the pandemic hit, she the frustrating part was the nurses on the ground were telling the higher ups exactly what should be done because they're dealing with the day-to-day reality of what COVID's doing, and they're from the top some pencil pusher somewhere saying, No, this is how we should do it. To me, that doesn't make any rational sense. Similarly, we see that in any business, like those that there's the there's a reason why those that can't do teach. That's that's the general rule of general rule of thumb, sure. Rule of thumb is okay, if you're like the best people to learn from are people doing the actual business. I always like, and it's bad, but if you're gonna take the real estate courses, okay, after that, then go shadow a real realtor for a month and and find one in your office or wherever you're gonna think, but just find someone you can watch do the business because the business in the book and the business in reality, people don't fit into these simple molds. You can say there's how many personality types, but every single personality you run into is a variant of that. And so there's benefits to understanding how who in a relationship, if you're dealing with an engineer, you can kind of have an understanding of their expectations. Hyper analytical, hyperanalytical. You're physicians, right? You can deal with the the the decision makers that are high level, the decision makers that don't know what to do, the indecisiveness. So knowing who they are is important, but understanding like how to deal with that is different on each and every person, and being able to learn that reading people is important. And so school doesn't really teach you that. That's why with my kids, I've been like, you want to learn how to read people, understand them, and then problem solve for them. That's how you make a living. It's not, oh, I know this much more information because realistically, today, most information is readily available. So if I need to learn something and I really want to, I could take a three-month sabbatical from whatever I'm doing and learn pretty much any specific thing well enough to be able to deal with the public. I'm not saying research papers or whatever, but just dealing with the functional public. If you took three months and just tried to learn everything about a very specific thing, you could you could do very well very fast.

SPEAKER_01 18:35

Interesting. And so you get started in 2008. Yep. Um, working with your dad. Did you my understanding is you then got into getting like buying your own real estate? Correct. Yep. And so what did that process then look like? So you're you're you're selling it and you thought, like, this is a good investment because I'm selling it, or you thought, uh, I can cash flow these things. Like, what was that thought process like?

SPEAKER_04 19:00

So what's interesting is I helped a lot of my uh my clients and or friends build wealth through real estate. I just never really thought about doing it myself. One was I was young, I had kids, like financially it seemed a little bit risky, um, like to take on the risk of the mortgages and the debt. I didn't, I just didn't have knowledge around that like I do today. I have a very different perspective today than I did then. Um, but it was actually what we were at Royal LaPage for 10 years. Uh me and my dad moved over to Keller Williams and we went to something called family reunion. Um, and while we were there, uh the owner, Gary Keller, uh, was talking, doing a keynote speech, and he said, every he his words were, every great deal your clients have bought has gone through your hands. So why don't you own real estate? Right? And so he said it, and my brain asked the question. So then we were fat, so that was in February. So what ended up happening was I went to a deal, I went to a client's house and I was just standing there and I would ask them, like, so hey, if you were to sell it today, because sometimes my investors would come in and if somebody seemed like they wanted to get sold quick and they didn't really want to go through any process, I could sometimes facilitate that between buyer A and seller B and get that done for them. Um, and and everyone wins because it's a quick close, two weeks, cash, no conditions. Maybe they could have got an extra 10, 15 grand, but they don't care. They're willing to take a bit of a discount to get the deal done. Um, and both parties win in that scenario. But I was standing there doing that. So I was at a house. Um, it was I told them it's probably worth like, you know, in the condition 120 to 130, which sounds crazy. I know everybody. And it was actually in 2019. Um, but it was a one-bedroom bungalow um on a property there with a basement, but it was it was tiny. Um, but what's interesting is I said, so you know, blah, blah, blah. If I could sell it for you today, what would you want? And he says, I take 100 grand right now. I said, So if I got you a hundred thousand dollars right now, close it in two weeks, you'd be happy. He goes, Yeah, I just want to get, I just want to move. He says, I don't care if you could get me one like if you can get me a hundred thousand dollars, call it. I'll take it. I'll take it. And he still says, I'll fix the roof. I said, okay. So first thing I do is I call a couple of my realtor buddies who've got clients. I call a few of my own clients and just start to shop because my objective is to help him out, right? Like, if I can, if I can double end it, great, but I don't mind if one of my other buddies who's in the business who has investors comes and brings it. So I call. And as I'm sitting there, that that conversation shows up in my head. It's like, why don't I buy it? Like, if it's such a good deal and the guy's fine with it, like there's nothing, I'm not, I didn't lie to him and say, Oh, it's worth this, and then try to do that. He goes, I'll take a hundred grand right now. I went, Okay. And so I called up a couple of my buddies who were who had cash and I said, Hey, I'm looking to do a deal. Would you back a deal? Here's the play, here's what it is, blah, blah, blah. And the first person said no, second person said yes. Called him back, said, Don't put the roof on, I'll get my own buddy to do it. Take the four grand off, you're paying for it. We got one 96 grand, call it a day. He goes, Yep, done. Boom. And that's how I started. And then once that happened, then my brain shifted. Now it it's complicated because again, as a realtor, it's interesting because I I actually kind of like it because it keeps you, it keeps me very honest. Because the the reality is, as a realtor, unlike a random person, is a random person can buy a house for whatever value they want and have no obligation to disclose any different. So let's say House is worth 300,000 and I pay you 150. If I'm just Joe Schmo, there's no obligation for me to tell you her house is actually worth the difference. As a realtor, I have every obligation to show you the true value today. And if I know of any reason why there would be a drastic change in value tomorrow, right? And so that was good. So I always would tell people here's what your house is worth. Here's what I can do though. I can give you a cash closing. You can stay in it even after it closes for a bit while we do some like I could flex for certain circumstances in my world. So when I would go to listing appointments, A, do the normal, just list it and sell it like regular, or B, here's this option. And I just leave them with both. And this is why I'm buying it at this price. This is how I see me making the money. And I just I'm honest with them. Like this is what I'm gonna do with your property. And so again, some would buy in and some wouldn't. So I think over the next four years 2019, 20, 20, 2021, 2022, yeah. So three, three and a half years. Um, I think I bought um 13 properties. Wow. Um, and so kept I had three uh before I made my big push and then bought seven all at once. That was that was the beginning of the end. It was just timing too much too fast. Uh too much when the market corrects. Got it. So leveraging about four million dollars as the market dropped 37% in six months. Yeah. That because of interest rates and everything else in 2022. COVID, all the jazz.

SPEAKER_01 23:20

Between eight uh COVID war, interest rates, everything kind of all went right.

SPEAKER_04 23:25

February 27th to April 15th, I bought seven properties. Like wrote wrote purchasing. But the problem was closed deals. I only had two closing before um June. Then I had three closing in June, one in July, and one in September. So that was the the breakdown of those properties. And so the issue is I was able to liquidate the one in September to somebody else. I was able to actually buy and make money on the one I closed in July. The three, though, that I closed in June obliterated me. All three of those were massive losses and the two that were closed already because all of those were bought at a time where the market hadn't shifted yet. I picked up the last couple as I'd seen the market start to shift, but no, I never expected to see what I saw. So I got a little more insulated, but and then the market corrected. I had a 23% fallout rate, meaning like the market could pretty much lose about 20% of its value, 23% of its value, and I could basically liquidate the assets back and probably be okay. It just went down by 37.

SPEAKER_02 24:19

Crazy.

SPEAKER_04 24:20

That was crazy. We went from 721 down to 485.

SPEAKER_02 24:24

Yeah.

SPEAKER_04 24:25

Wow. And then bounced back up to about 515. We reached back up to about 600. But like the issue is you're talking in real time. I've got 1% leverage cash on 4 million. That's not a little bit of money. So 1% per month, 12, you know, 12%. Yeah. It was uh it was a moment crazy.

SPEAKER_01 24:41

So that's and that's I mean, listen, that's one of those, that's one of those learning moments where like you understand the business, you're in the business, you're disclosing everything to the clients, like you're doing everything right, and then you're just like, I'm gonna make a push at this. And what was the push? Well, like, what was the thought like? The the thought was I'm gonna go all in on real estate and grow this giant big portfolio, and I'm gonna have a bunch of doors because that's what everybody tells me I should do, and and then it just all of a sudden changed fast. Um, or was the thought like, you know, if I buy a few more doors, you know, I'll have constant cash flow all the time, and I can just sell when I want to sell and don't have to work hard anymore.

SPEAKER_04 25:27

There was a there's the idea of freedom. Yeah. Um, what ended up happening was it wasn't really any push from anyone. It was I had I kept getting opportunities because again, people started to reach out to me, call me, be like, hey, you want to pick up this deal, pick up that deal. And so, like, I bought and just like so I was a facilitator, so I I would keep properties that were multi-unit. So if I could if we were duplex and add the third unit uh ranch, add the basement unit, like that was my thing. Like to me, any property that was multi-unit was worth keeping, any single family straight up was a little bit more flip, right? So, which is what killed me. So the biggest issue was twofold. One was uh it was so my hold rate on everything was based on a three and a half percent interest rate, not a six percent interest rate. So when we're talking when interest rates were two percent. Yeah, so again, I built in solid safety features. So I thought before what I could possibly imagine happening without crippling the entire economy, I was just wrong about what that was. I didn't realize how resilient the market could be with a six percent interest rate. I didn't think that was possible. I thought if they went up there, like the world would end. And it didn't. It did for me and some of my investor friends and other people who did what I had done, but for the general population, it had almost no impact because they weren't in the the day-to-day motion of it. They were in five-year fixed rates, or if they were variable, there were things that they could adjust for. Right. So my whole world just in that moment, I again, and even when you go back to the 08 crisis, the 08 crisis was a different function. There was a different issue that caused it.

SPEAKER_03 26:57

Right.

SPEAKER_04 26:57

This was something I didn't understand that the policy rate would have such uh a quick and um I mean nobody thought they would raise the rates that high that fast. Right. Even when I talked to my banker, because my primary, so my primary was at one and a half percent, and when they ticked up the first time, so originally I could have locked in at uh 2.42, I think was what I had, or I could get one and a half and take the variable. So it's like, okay, so I got uh 1% clearance for the next five years. I'm like, I don't like even if it goes over, as long as it holds for a little while. Like, and this was this was in 21, so there wasn't this major situation. And then uh in 22 it starts to climb. So I call as soon as it happens, I call him, I go, Hey, what's the lock in rate right now if I want to switch? He goes, it's uh two eight nine. He says, But I don't know if I would do like the market's got to go up a lot. And I'm so I'm talking to, and don't get me wrong, like this guy knows his stuff. It wasn't none of us saw it. It wasn't like there was one person out there saying, Hey, watch out, there's six percent rates coming, three and a half. He's like, but what? But I wouldn't get to three and a half. So at 289, my rate had to reach three six or three eight before because I'm almost not minus one percent, 95 points. So before I'd even catch up, like I'd have to raise my interest rate by basically one percent or more. And he's like, I wouldn't do that because a million dollars is 10 grand. And I said to him, okay. And so I listened. Final stay. So final stay, and I'm not, I don't blame him, just so we're clear. He gave me advice and I listened. And I don't think he gave me wrong advice. I'm pretty sure if he locks me in, he makes money, right? Like, I think by liquidating the one into the other, there's a there's actually a benefit for him. I don't think that was negative advice. I just think it was it was he didn't know. So I really have to remind myself for as much as I want to blame myself at times, there's this desire to like, yeah, you're an idiot. It's like, no, I I might have overleveraged, I might have done some things wrong, and I might have made mistakes. That's not to say I didn't, but I couldn't know what I didn't know. Right. And to hold myself as if I should have, I think is a is a very it's not helping. It doesn't help me become better, it doesn't grow me in any way.

SPEAKER_01 28:55

Yeah. And so if you had to then say give yourself like three three big lessons you could learn from that, what do you think those lessons would be outside of what you just said, which is like you get it gotta give yourself some grace for no don't not knowing what you don't know? Right. And I don't think there was an extremely small part of the population thought that you'd get to six and a half and seven percent rates. Right. So outside of giving yourself some grace to be like, I didn't know what I didn't know, what would you say three lessons you could or any other business owner, whether real estate or anything else, could take away from a lesson like that?

SPEAKER_04 29:39

So the one of the lessons I learned was that when all of your wealth is in equity and you don't realize that so I it sounds crazy, but I didn't ever I always considered that if a deal went bad, let's say I had to tap for 50 or 100 grand because the deal just goes bad, I would just tap an asset to pay for it because I didn't consider that all of them, all my personal wealth, which was tied up in real estate, and all my leveraged wealth, which was playing in real estate, would all lose its value simultaneously. That sounds pretty logical if you think about it, but I just never really considered that. What I look when I looked at like when you do your wealth portfolio, it's like what's your asset worth? What's this worth? And then you this is your net worth in relationship to your debt, right? And so I was worth$1.5 million, sure, right? Like that's call it if I liquidated every dime at that moment, yeah, I'd probably end up with between one point, probably$1.5 and$1.8 million washed. Yeah, cool. But what I didn't consider was again, all that real estate was still well leveraged. So you're talking about that being this amount of real estate at that price. So call it three, four million dollars worth of real estate, and then having the leverage underneath, so having that variant. Well, all that real estate went back to even, right? So I didn't lose much money on these properties, if any at all. If I still made some money on these properties, but they weren't worth that anymore. Right. And then when this had to all of a sudden these were in trouble, I went to go to the bank and knock on the door, this door, open the safe, and the money was gone. And you're just like, huh. Interesting. So one of the that would be called diversify, I think is uh a word that's the term we use a lot.

SPEAKER_01 31:11

Diversify your assets.

SPEAKER_04 31:13

Um, if you're going to leverage the way I leveraged, like using my position over here to kind of leverage against over here, understand better that if they're in the same game, you it's not it's not it's not a good idea. If you're going to if I had liquid cash of$500 or$600,000 that I could put into a market and it was over here protected, and then I have my real estate with$600, and then I have whatever, right? If I would have broken it up into three families, what didn't happen was the real estate market fell and things changed, but the these mark those two would have been okay. So I would have lost six hundred thousand, not all of it. But because the one got hit so heavy, I got hit right. And of course, I trust what I know. The reason why I didn't invest, I did try to invest with you know guys like yourself along the way. And uh for me, it was like I'm not, I don't have my hands on it, and I like to. And so for me, I would prefer just to invest it in real estate. So if I had some extra cash kind of kicking around, sure, here's 20, 30 grand, throw it in, you know, and then if I needed it, I'd just come get it back. But yeah, that's not really what you guys do as a general sense. So I just want to be clear to anyone out there, that's not what most of them want to be doing. They like to hold on to your money and actually grow it over time, yeah.

SPEAKER_01 32:19

Um, yeah. I mean, listen, have a have a diversified plan with some flexibility and access to cash if needed, and not putting all of your eggs in one basket.

SPEAKER_04 32:30

Correct. So that would be one. Um another, another is um when when engaging uh like one of the problems I ran into was crews. So it was like I needed a secondary crew to finish work. That's how I ended up partnering with somebody, and then that was how I was able to kind of amplify because all of a sudden I didn't just have one crew, now I had two. And so by doing that, it gave me the ability to buy more. And in that moment, the issue was I'd never I thought I knew what I knew, and this is where having a professional like an accountant and a lawyer review your idea is smarter than you just doing your idea. So that would be the second lesson. If you have a great idea, beautiful, show it to some other people who are smarter than you in arenas that you don't play in. Yeah, because if I had, if I showed what I was gonna do to an accountant, they might have warned me about those things, or even a financial advisor like yourself. If I showed you what I was about to do, then you might have been like, hey, do you not realize like these things are connected? And my brain would have been like, oh no, I like wow. And you'd have been like, This right here. Ah because I didn't, like I said, I just didn't see it. It's not that I didn't know, I just didn't see. Right. And a part of it would be because I didn't want to. Right. That's one of the greatest other mistakes is we we uh when there's great opportunity, we don't really want to hear no. We think it's a good idea, this could be amazing. We don't want to have somebody come along and poke a hole in it. So I think A leaning on smarter people and B being willing to actually walk away from what might be a great idea is extremely important.

SPEAKER_01 34:06

Yeah, it's interesting you say that because I think a lot of people just they love so much to have hands-on, be in control, but at the same time, like I tell people they just you you don't know what you don't know and you're like I would never try to fix a car.

SPEAKER_03 34:24

Right.

SPEAKER_01 34:24

I'm terrible with that kind of stuff. I was never taught, I nor do I care to learn. Right? I take my car to a professional to get looked at. And some people are like, oh, dude, just change your oil yourself. I don't know how, right? Yet at the same time, when people are like, Oh, I'll just manage my own money, and I'm like, Do you know how? Like, are you actually watching it like you should be?

SPEAKER_03 34:48

Right.

SPEAKER_01 34:48

Uh, because most people are like, I'll just trade myself. Okay, well, you go do what you do, and then instantaneously on one day when Trump decides to tweet something and the market either goes up or down by you know 10% in one day, you were doing your job, but you weren't paying attention to what was going on.

SPEAKER_03 35:06

Right.

SPEAKER_01 35:07

Right. And that's kind of why we all kind of rely on each other, right? Is I have an expertise, you have an expertise, so and so's got an expertise, and we need to work together, yeah. As a group to make sure that not only are you successful, but they're successful, and I'm successful, and we can work as a team, but being an individual, you can only go so far before things are gonna crumble.

SPEAKER_03 35:28

Right.

SPEAKER_01 35:28

Right, which is which is interesting. So, okay, so I mean, those are some big lessons, man. I mean, uh a lot that it's an expensive lesson.

SPEAKER_04 35:37

It was an expensive lesson, yes.

SPEAKER_01 35:38

But so how do you think that's changed your mindset around the way that you might look at a deal now, or the way that you look at maybe getting back into the real estate portfolio now? Like, how does that change how you uh approach something now?

SPEAKER_04 35:56

Yeah, so interestingly enough, like I I don't think I have any fear of doing a deal if a deal makes sense. Um I think the biggest change is a the market isn't where it was. Um financially I'm not in a position to hold due to circumstances that happen. Like I would need partners in ways, but if there were if there was a good enough deal, I'm smart enough to go find a way to do it.

SPEAKER_03 36:18

Right.

SPEAKER_04 36:18

I think right now my focus has just changed. Like, so so I'm a believer and I believe that God allowed what happened to happen for a purpose to change my heart. So there was a hubris about my nature, right? And I can see what that cost me. Um, because I was too big to fail, like the that that kind of attitude. It's like I know what I know, I've been doing it at that point for 15 years. Like, how am I gonna lose?

SPEAKER_01 36:41

Young, cocky, yeah, arrogant, and I was a little too confident.

SPEAKER_04 36:45

Yeah, kept winning. How do you how do I lose? I kept getting wins and better and better wins. So when I was so you can agree with it or not, but like there was a point um where there was this as I was joining with this business partner, there was this thing that's like, don't just step back. There was this like feeling this feeling, this thing, and it's like, but he's a buddy, like why? Like, um, I don't see any issue with getting into business with this person. We're good friends, like we like there's no I was thinking about it from the wrong perspective. I think it was because of what would happen. See, I don't always know myself as well as I would hope. And so the idea that by adding fuel to a fire that was already a little bit out of control was not what God wanted for my life, and so I didn't listen. And so then he's just like it wasn't like some people are like, Well, God then didn't no, I think well, everyone got hit. There was something coming, and he was trying to warn me. And I think if I had stopped right there and I just stopped, kept those two, done that, I might have lost a little bit of money with a couple of them, but there'd only been two. I could have overcome the two. That'd have been I would have washed the other properties, everything else, I would have been in a position to hold and outweight the problem. So the issue was was because of the leverage, I was in a spot where no matter where I turned, I couldn't mortgage a property because I needed to keep all the money at 1% because that that I couldn't get rid of enough of it. Then I'd have the mortgage at six percent when I expected it at worst to be three. So how was I gonna rent them? So my negative cash flow monthly would have like every way I looked was wrong. And so when I when I sit there and I believe like what that God did that, like I walk humbly now. And so there's a humilium life, but it doesn't remove the opportunity, it actually amplifies it in some respect. I just think I look at money very differently. Yeah, um, freedom used to be in finances, now freedom is in following and doing the will of God. So um God's changed my life drastically over the last couple of years, like um through the bankruptcy, um, when I finally gave up. So I took two years to actually go bankrupt when I was bankrupt the day the market did that. There was no recovery, there was no, I just was unwilling. I fought tooth and nail um to overcome, right? And finally one day I was just like it was February. I'm like, um, I don't think I can, I don't think it's gonna work. I was working doing the social media thing, trying to drive business, find another way to just do the real estate thing and drive generate enough business just to carry the debt. And the issue was was the jet just kept growing, right? Started at 580, ended up at 780 by the time it was all done because the money, right, just kept growing out of control. And I couldn't, I was pacing it and paying this and then losing that, and then 10,000 more. And it was just like, yeah, by the time the tower was built, you're sitting there and it's just like yeah. And so to humble myself from where I was, the idea of who I was to be able to write off all the value that I've had within myself. So that was the other big issue, is I had no internal value. I was worthless without my money. Every value from my family, every value for my friends, every value that I kind of brought was in that realm. So to lose it, to recognize that that wasn't why any of these people actually liked me, um, why they're my friends, why they invested with me. Because I had investors lose and they're still friends with me.

SPEAKER_02 39:54

Yeah.

SPEAKER_04 39:54

It's fascinating to actually see that people care.

SPEAKER_02 39:58

Yeah.

SPEAKER_04 39:58

And and to to care about you, not the money. And that was me. I was never these people ever putting that that way. It was I thought that as long as I could provide, then people would love me.

SPEAKER_03 40:08

Yeah.

SPEAKER_04 40:08

Right. And it wasn't that it was that well thought out either. It wasn't like I wandered around with that. It was just my actions produced that attitude.

SPEAKER_01 40:15

Yeah. I mean, it's it's the identity that you gave yourself and the stories that you told yourself as to why people hung out with you, why they answered your phone call, you know, was that it was money. I made the money or I grew their wealth, and that's why they called me. But I mean, I had the same thing with swimming, is like I retired from swimming and I was like, oh my God, like I'm a failure, and what am I gonna do with my life? And what's the point in trying? And it's like, just just because I swam for so long and competed for so long didn't mean that I didn't have worth or that I was just an athlete. I was just a swim, like there was way more to me than that. Right. But when you're in the middle of it and you're in the thick of it, that's not what you think about. You only think about that. I'm this thing. And I love what you said there about um just right before that. You sort of where was I gonna go with that? You were you were sort of trying to trying to make it work, trying to continue to fight. And at a certain point in time, sometimes you just have to go, I'm done. This obviously isn't for me, or I'm doing things the wrong way, or I need to pivot somehow, right? And you can only fight for so long. Right. Um it's interesting that you had that kind of thought process. And so where where does that take you now? I mean, you're you're you know, a few years removed from it, you're in a different position, you're in a different place. Um what's what's going on now?

SPEAKER_04 41:55

Yeah, so with everything, um, so transitioned life in in certain ways. So real estate's still the primary business. I still love to help and serve people. Um, but got God brought about um just changes. He asked for things. So last year, one of the bigger changes was I gave up alcohol. So as of June of last year, I've been sober. Um, so it's interesting. So God took that, other things, um, pornography and other issues in my life all went with it. So and then he kept asking for more things. I don't have social media on my phone now. That happened more recently. Games came off my phone. Um, a lot of the distractions. And and this, like again, I'm a I believe that God is real. I believe he lives inside of me. I believe like he has a purpose and plan. And so, in all of that, he brought about um involving my wife was desiring to join uh young adults at our church, so as a as leadership, because of course we're no longer young adults. Um, and so what we started to do that in September. And I kind of walked in there and it was a little awkward, right? Like, I'm a 40-year-old guy hanging out with a lot of them are younger, but some of them are 30. Like it's just I'm like, how do I relate? And then so now, and then all of a sudden there was just stuff that happened there. And then God opened up a door where there was um one of the other pastors of the church um talking, and she goes, You know, yeah, I was in ministry for 10 years, then I went out and I did um, I think she was um in counseling, like doing counseling work with women and doing some stuff like that, and then came back to pastoring. And for whatever reason, when she said it, it was this you can go back. There was this inner inner thing, and it was like, Okay, well, what does that mean? And it's like applied back to Bible college, like the same one you were at 22 years ago. I'm like, Wow, oh, school, me and school are not a huge, like I do school for its purpose. I'm not a huge I love to learn. And so, and so back then, and so anyway, so I'm like, all right, you know what? I'll apply. And so then moving forward from there, um, the course got accepted, uh, started in January, and God just so right now I'm in full time. Bible college doing full-time um real estate. Benefit is it's um on demand. So again, I can I get up at four in the morning a lot of the time, watch the videos, do the schoolwork, go for breakfast, come back, do some schoolwork, then click into real estate, do the real estate thing, and serve. So God is doing something, and I'll say this I have no idea what I'm doing next. Um, right now my life is in a really flexible area. Like we sold the last piece of real estate I owned, which was my primary residence back uh last year, closed it in December. So I'm renting now, so I could be here next year, I could be anywhere in the world next year. There's a freedom, and and again, as a realtor, it's weird because like owning real estate, but but my purpose isn't because I don't think real estate is worth owning. I think what God has planned next for me may or may not be here.

SPEAKER_01 44:48

Right.

SPEAKER_04 44:49

And there's a freedom to be able to not have to put anybody out. It's like if God calls me to go to India, I can be there tomorrow. If God calls me to go back to Brazil or to go wherever, I can just go, I can go. I don't have this need to justify to anyone. I can leave my business. I'm part of an amazing real estate team. So it's not like if I walked away, my clients wouldn't be taken care of by people that I know and trust. So even in a scenario where God does something like that, there's an opportunity now where he's building it in. Now that doesn't mean he's going to, right. But I'm able to.

SPEAKER_03 45:22

Right.

SPEAKER_04 45:22

There's a freedom in my life, and I I always thought freedom would come with money. Freedom actually came in surrender.

SPEAKER_01 45:28

Interesting. And so it's just such a crazy story to go from like getting into real estate, doing it for 10 years, having some success, and then being like, okay, I'm gonna now do it myself in a very short window, building a pretty significant portfolio. I mean, I would probably say anything more than like two or three houses is significant. Seeing it all come kind of crumbling down, and then being like, okay, like what does this all mean? It's kind of interesting to see how the story just, you know. But I mean, life is up and down. We're gonna have the the the ups and the downs and the pros and the cons and stuff, right? Um that's just such a such a unique story. I think a lot of people in your situation wouldn't be quite as I don't know if it's I don't know if happy's not the right word. Um content, cheerful, yeah. Uh it just like for someone who's gone through that fairly recently, you're like very just like it's joy relaxed and joyful.

SPEAKER_04 46:27

Yes, that's so the fruit of the spirit, that's one of them. So again, there's when you don't put your value into the things of this world, and you put your value into the creator of this world, there's there's a fullness that comes with it. So it's it's counterintuitive to all of human nature.

SPEAKER_03 46:48

Yeah.

SPEAKER_04 46:48

That or what we're taught. Right. Like this idea that is a as human beings, like you'll find value in uh your wife, you'll find value in this success, you'll find value in that success, you'll find value in winning that tournament. Like it never lasts. But what does last is walking daily with God. Like there is this freedom that like I get to engage with people. Like you randomly called me to be on this show yesterday. I'm like, yeah, sure, let's do it. I didn't even know exactly what I was doing.

SPEAKER_03 47:16

100%.

SPEAKER_04 47:17

But but I get like there's opportunity to just engage with the world. Like I said, there's an opportunity to engage with these young adults. I'm in other ministries doing things, but like ministry in the sense that I say it is just engaging with the world in a way where you just get to um spread joy and love and you have caring compassion upon them. Like I if if we have a more call it biblical conversation around truth and what the world is and where those things are, I'm going to align with what the Bible says, but it's in a loving way. Understand, like I don't hold a grudge against any human being. I understand sin is real. That's that's me. But if you disagree, okay, that's you. Yeah, there's nothing. I think the hard part for a lot of people is they think that life is about getting when it's actually about giving. Giving. It's how do I serve people? Yeah. In your marriage, it's how do I serve my wife? It's how do I serve my kids? How do I serve my clients? How do I like it's an attitude of service, and then with that, right? What what comes is is is gratitude, right?

SPEAKER_01 48:17

And so it's funny you say that because I was literally watching, I think a reel or maybe on Instagram, because I still have social media. Um, and Tony Robbins is like, you have to kind of relate it to like the like the first part of a relationship, right? Like when you're first dating somebody, uh all you care about is giving, right? Paying for the date, bringing flowers, opening the car door, doing all those things. And that's one of that's some of those things that made this person fall in love with you. But the entire thing was about giving, not getting. And once we turn our expectations from giving to getting, that's when things become challenging. And I was watching it the other day, and I obviously he was talking about like marriage and relationships, and I was just like, it it's so interesting, even in a sales role, when you see that salesperson who is always just trying to get and never give, they're always stressed, anxious, trying to make a sale, trying to oversell instead of just giving the information that the person needs or wants.

SPEAKER_03 49:27

Yeah.

SPEAKER_01 49:28

Right. Um, so I love the fact that you're that you say that because it really is. It is giving, it is serving. Um, and there's so many, obviously, there's so many different ways to give and to serve, but I think a lot of people can can take that and could learn a big lesson that it's really not about you, it's about the people you're serving, it's about the people you're helping and giving. And if you give a lot, you will get, right? It will come. Yeah, it doesn't have to come right away, but it will come, right? So uh we're we're running pretty low on time here. Um, that conversation, it's we could talk forever about this. Um, but we always end the podcast asking people uh one question, which is what does success mean to Mr. Sylvester?

SPEAKER_04 50:15

So today success means living out the will of God in a way that is evident to those around me.

SPEAKER_01 50:24

That's good. What do you think suc what do you think you would have said to that question five years ago?

SPEAKER_04 50:31

Financial uh financial freedom or or the ability to self-sustain.

SPEAKER_01 50:37

So going to 180 degrees.

SPEAKER_04 50:40

Yeah, it it and that's the whole thing. The what the world offers is a hollow version of what God does. Like wealth, one one of the fascinating things is the wealthy people in this world seem to still feel empty inside. There's they fill it with money, they fill it with yachts, they fill it with all of these things, and yet they just want more money or they need more fame, or they need like but if you just rest in who God is, it's it's it it says like it says the the the lowly, right? Like those who are it's not that we're weak. I'm not weak, I'm actually much more powerful. Uh but there's this there's this idea where we're if we walk humbly, it's not to say weakness, like people think that Jesus was a weak. Jesus was powerful, he spoke with power, he just spoke with care and compassion for people. And he spoke with the sinners, he didn't like with the religious people. If you actually watch that conversation, he had some things to say about them. And so I think it's very important when when you look at life, you understand what does it mean to be whole, right? What actually fills you? And if you think it's anything other than the creator, I I don't have another answer. I've never found anything else, right? Sure, but that's that's how I that's awesome.

SPEAKER_01 51:58

I mean, listen, uh, there are a lot of people out there that are just like you, right? And and following God's word, yeah, right, is is an extremely important part to a lot of people, right? So um I I love that answer. That's a great answer. Um, well, listen, uh, we're out of time. Yeah, I I I appreciate you doing this sort of last minute. Oh um, I've wanted to hear this kind of this story for for quite some time since uh since you had me on your podcast because I knew there was uh a sort of a big change in in philosophy. So I love the fact that I got to unpack it a little bit. I'm sure we'll have some more conversations. Um, but thank you very much for doing this podcast today. That was awesome.

SPEAKER_04 52:38

Thank you so much, Sean. It was great to be on and I'm grateful that you thought to call me.

SPEAKER_01 52:41

Yeah, no problem, man. I appreciate it. Uh, everybody, that's uh another episode of Cracking the Success Vault here with uh Spectre Group. As always, you can find us on uh any streaming platform, whether it's uh Apple Podcast, YouTube, uh Spotify, you name it. We'll be back next time.