
The Wisdom, Lifestyle, Money, Show
The Wisdom, Lifestyle, Money Show is here to help Canadian's invest better in Canada & the U.S.A. We specialize in mortgage financing and education in both Countries. Discover how to become a better investor and access the financing you need.
The Wisdom, Lifestyle, Money, Show
Always Work With Investor Focused Experts Who Also Invest With Rhys Trenhaile
In this episode, Scott interviews Rhys Trenhaille, a commercial real estate specialist who focuses on working with investors in Windsor Essex County. Reese shares his unique journey from university track athlete to successful commercial real estate investor and agent, emphasizing the importance of working with professionals who practice what they preach.
Key Insights & Takeaways
The Power of Early Real Estate Education
Reese's story demonstrates how early exposure to real estate investing can create lasting wealth. While training for track and field at university, he and his teammates purchased seven student rental properties and even two race horses by the time they won a national championship in 1998. This early start led to one teammate retiring at 48 years old, showcasing the long-term wealth-building potential of strategic real estate investment.
Why Experience Matters in Real Estate Teams
Scott emphasizes a crucial point for listeners: always work with real estate professionals who are actively investing themselves. Reese and his team don't just sell properties—they own substantial portfolios, including major development projects worth over $100 million in downtown Windsor. This hands-on experience means they understand the challenges investors face and can provide guidance based on real-world results, not just theory.
Overcoming the First Investment Hurdle
The biggest barrier for new investors isn't financial—it's mental. Reese explains that people who have been employees their entire adult lives struggle most with learning to take calculated risks with their money. The fear and endless questions that plague first-time investors prevent them from moving quickly on good deals, which experienced investors can capitalize on immediately.
Investment Timeline Reality Check:
- First Property: Usually not a "steal" due to inexperience and hesitation
- Second Property: Still learning, asking many questions
- Third-Fourth Property: Finally ready to recognize and act on great deals quickly
This progression is normal and expected. New investors shouldn't expect to hit home runs immediately—building expertise takes time and experience.
Strategic Property Selection for Portfolio Growth
Rather than traditional duplexes that can create financing roadblocks, Reese recommends the BRRRR strategy (Buy, Renovate, Rent, Refinance, Repeat) using properties with additional dwelling unit (ADU) potential:
By adding a basement suite, investors can achieve $1,000+ monthly cash flow, increase property value, and refinance to recover most or all of their initial investment for the next purchase.
Working with the Right Team
Successful real estate investing requires partnerships between experienced agents and financial experts who specialize in investment properties. The team approach helps investors avoid common roadblocks and structure deals for maximum growth potential, including mortgage-plus-improvement financing to fund renovations without using personal capital.
Resources Mentioned
- The Vanguard Team Website: thevanguardteam.com
- Team YouTube Channel: Features recent market analysis videos and investment strategies
Welcome to the Wisdom Lifestyle Money Show. I'm your host, Scott Dillingham. Today I have Reese Trent Hill from the Vanguard team at Manor Realty with us talking commercial real estate in and around Windsor Essex County. How's it going, Reese? I.
Rhys Wyn Trenhaile:Yeah. Good, good, good. Got my coffee? I'm ready Scott.
Scott Dillingham:Awesome. Awesome. Yeah, me too. And I, I'm excited to chat because not only are we talking about real estate and everybody can talk about real estate, but I think what's super important about what you do is you actually specialize in working with investors. And not only are you a commercial investor yourself, right?
Rhys Wyn Trenhaile:Yeah.
Scott Dillingham:You, you sell to clients. So I think that's super important for any client or person who's listening. You always wanna work with people who are doing what they sell. Because if they're not, there's, there's a lot of risks involved with that. So how did it start? Like how did you get into the commercial real estate space?
Rhys Wyn Trenhaile:So before I was a real estate agent so I was in the university a very long story short I ran track and field at the university of the guys. Bought a student rental property
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:would go on these long runs training together and we would ask tons of questions. So by the time we won a national championship, and I'm gonna date myself here, but, we won a national championship in 1998 and by then five guys owned seven student rental properties and two race horses at the racetrack.
Scott Dillingham:That's awesome.
Rhys Wyn Trenhaile:yeah, so I got the bug early. To be a landlord. I was literally in university renting out the university students, which is a bit weird. but a bunch of us were doing it so it didn't feel so weird. And a lot of those guys had gone on to great wealth with real estate investment. Like one's already retired at 48 years old, you
Scott Dillingham:Nice.
Rhys Wyn Trenhaile:so the that's where it started. And then I went through university. I became a lawyer. I never practiced. I got called to the bar. I was going to go work at this law firm. Long story short, they gave the job to somebody else because they had to wait for me to get called to the bar for four months.
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:at it as don't worry about it. There's a reason why, right?
Scott Dillingham:Mm-hmm.
Rhys Wyn Trenhaile:And a lot of it was my buddies were all tradesmen. They didn't have to go to school for seven years were already making at the time, between 60 grand and 120 grand a year, which would be like a hundred grand to 200 grand a year now. And I'm like, they wanna start me at 42,000 as a lawyer. like, I can't make less than my buddies.
Scott Dillingham:Yeah,
Rhys Wyn Trenhaile:Work, CNC, machinist, it's not
Scott Dillingham:absolutely.
Rhys Wyn Trenhaile:bad profession. I love those professions, but I'm a
Scott Dillingham:You'll never hear the end of it.
Rhys Wyn Trenhaile:I'm a
Scott Dillingham:Yeah, you'd never hear the end of it.
Rhys Wyn Trenhaile:know. So that's when another lawyer. he was already selling real estate. He said, Reese, you're a natural salesperson. You should sell real estate. was like, I'm already really interested in real estate. I, the real estate law, when I was ing at MCT law firm, I was really interested in it.
Scott Dillingham:Mm-hmm.
Rhys Wyn Trenhaile:rental properties. Do you know what I mean?
Scott Dillingham:Yeah. Mm-hmm. Yeah.
Rhys Wyn Trenhaile:and for another year. So that's how that all happened. That was the, the evolution into that guy. And then the last 21 years, I've become a better and better investor. I, we pass on that information to the client base to make them better investors and. Essentially everybody that invests with us know, one of the property managers that we use, one of the contractors that we also use, one of the specialists like you that we use, right? Like Steve, Steve Rouge on our team right now is getting some stuff done with you. And in essence, and this is hard, this is harder, I think, for WinDor rights than the out of town Toronto investor. To understand is we practice what we preach, you know? So we now have clients, because I've been doing this for 21 years, we now have clients that are retired. They've sold off the income properties. They've bought a multimillion dollar house on a lake, and they're done. And that,
Scott Dillingham:Hmm.
Rhys Wyn Trenhaile:There's more than one of those guys that has just done that. Right. And, for myself, yeah, like. I'm living quite well, but I'm not living quite well because of my real estate commissions, just because of how I converted my active income into passive income through real estate investment. And again, Steve Druj on the team, and I know Steve doesn't mind me saying this. Steve's got a Lamborghini, right? Steve was the first guy in town with the New Lotus that like, we practice what we preach. So when somebody on Facebook goes all, all you real estate agents say the same thing, it's just, I just wanna go whack.
Scott Dillingham:Yep.
Rhys Wyn Trenhaile:we
Scott Dillingham:Give him a little smack.
Rhys Wyn Trenhaile:Well, so one of my posts one of my videos I just did with Sadie, let me see if I can find it here. On Facebook, when I just did a, I just did a video with Sadie and I posted it. Sadie more on her team guys. She sells more high-rise condos than anybody because of how many she said, sells to investors. She also does new builds. You wanna do a new build, one of these federal pre-approved sixplex designs. You go to Sadie. Sadie's in the, the Fami, like her whole family's construction. Everybody knows her down at City Hall or Burg's Town Hall. They all love dealing with her. That's how you get things done and built. Yeah, let me see if I can find this here, because
Scott Dillingham:Yeah, I gotta talk to her about the CMHC stuff, just thinking out loud.'cause if she's building six units, we can do up to 95% loan to value,
Rhys Wyn Trenhaile:there you, so
Scott Dillingham:which was massive. Yeah.
Rhys Wyn Trenhaile:trying to find enough people that want to build those. the infill lots. I don't think people realize how easy that's getting now. Right? Like even dealing with the bureaucrats down at City Hall. When I started doing some major, major projects, guys, I got about a hundred million dollars in projects going on downtown Windsor right now. Converting old buildings from commercial use to residential use on the upper floors. A lot of money for it at the three levels of government. Boy oh boy, Scotty, when we had to start dealing with the bureaucracy. talked to him four years ago, you had to submit the same document or six times, and you never knew who was folding up your file. You couldn't tell. It was insane. Now it's all cloud permitting. Now you have a development assistant coordinator. So not only can I, not only do I have to only submit the same documents once I can see who's holding up my file. Then I can tell my development assistant coordinator, he is an awesome human being. can you see why this guy in public works? This person in Heritage hasn't done their job yet. And I tell you what, Scott, eight times outta 10, a response and that bottleneck's gone within 24
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:Like, and people didn't believe
Scott Dillingham:That's incredible. Yeah.
Rhys Wyn Trenhaile:it is way ba it's still got a lot of work to go. There's still a ton of work to go. I. nimbyism that's embedded into these, the zoning and stuff is ridiculous. That's causing the homeless like it's just so
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:But probably sped up the process, I would say by half. It used to
Scott Dillingham:That's incredible.
Rhys Wyn Trenhaile:something like that done. Now it takes a year, which is totally reasonable.
Scott Dillingham:Mm-hmm.
Rhys Wyn Trenhaile:it's
Scott Dillingham:No, that's awesome.
Rhys Wyn Trenhaile:Yeah.
Scott Dillingham:That's incredible. And what we're gonna do for everybody who's listening too, is we're gonna have multiple segments because Reese and his team collectively. There's a wealth of advice from different, different aspects, but I think that it's really cool just to talk about your story in the sense Reese, as, as sort of the starting episode with, with you and your team is just that, like you said, right, you're running track and considering and talking out through rentals, right? And then it goes from there to how many units like is the Canada building just for fun for people listening.
Rhys Wyn Trenhaile:67 residential to retail. Yeah,
Scott Dillingham:See, that's massive, right? So anybody can get there, right? If you've got the right team and the right expertise and experience there. And so I love that story, right, because people just getting started, you know, they're discouraged about buying property number two,
Rhys Wyn Trenhaile:Oh
Scott Dillingham:Where you're, you're on a like completely different level, but it's, it's years of persistence and not giving up and.
Rhys Wyn Trenhaile:one, though I find for investors, especially if they've never taken a calculated risk in their lives, if they be, if they've been an an employee entire adult lives, that it's the mental side that they struggle with the most, which is learning to take small, calculated risks with your money. They really struggle with it unless you point it out and they become conscious of it. That's a big one. I'm surprised you
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:one.'cause really we find it's the first one. If we get the first one done, them settled in and the fear goes away, the questions go away. And now they can focus on building up the portfolio. And usually it's like the third or fourth one where you get your first deal and people go, oh, why can't I get a steal the first one?'cause you don't even know what a steal is yet,
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:do know it's a steal. You can't move fast enough. You're scared. You got a million questions. the, the veteran investor, he's gonna go, oh, steal Reese. Write it up. Make it conditional for a day. I just gotta make sure I get my financing. You can't compete with that as a rookie investor, so you're not going to get a steal 99 times out of a hundred as your first property, probably not your second property, but by your third. You should start.'cause now you're ready. You know what to look for. You know what a steal is. You're mentally ready. You're financially ready.'cause you've already been dealing with Scott. Scott likes you. He trusts you. You trust him. You trust your real estate agent'cause they've been making you wealthy. Boom. That's when it starts kicking in. Everybody wants to hit home, but not everybody, but a lot of people wanna hit a home, run their first time. It's like you're dreaming.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:You're not gonna
Scott Dillingham:Steps.
Rhys Wyn Trenhaile:field. So I've been doing this for too long. I'm too quick, I'm too
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:I'm ready to go.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:get back
Scott Dillingham:You, you.
Rhys Wyn Trenhaile:Scott, you
Scott Dillingham:No, no, no. You're right though. But you're, you're right about the mindset. You're right about the mindset. I see that a lot. But I think the reason why I'm saying deal two is the hardest is because sometimes we see a lot of investors that will say, you know, maybe they'll move into a duplex. Right? And that's their first investment. So they're renting out one side, they're offsetting, and then they're gonna move into another one. So they're, they're. Leveraging the 5% down programs that are available.
Rhys Wyn Trenhaile:Yeah.
Scott Dillingham:Right. But once, once you're on deal two or three or four, right, and that those 5% options disappear,
Rhys Wyn Trenhaile:I see.
Scott Dillingham:then it's now you not, now you need to bring money into the deal. Right. And then that's where we're seeing the traction slow for a bit.
Rhys Wyn Trenhaile:But this is where I think a good partnership between real estate agents that know what they're doing with income properties and financial experts like you guys with income properties comes in handy. we can avoid those roadblocks if we know you're gonna roadblock by the second one. We're not going to want to sell you a traditional duplex. If you, we know that's gonna be it for the next four or five years, you're, you're stuck at that point. Right? What we would suggest instead is you buy a house you can put a mother-in-law suite into the basement.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:different types of additional dwelling units. Guys, the basement one that's the cheapest. The second or third cheapest are the addition on the back of the house or the detached garage.
Scott Dillingham:Mm-hmm.
Rhys Wyn Trenhaile:expensive one, which everybody wants to talk about until they're blue in the face, is the detached unit in the backyard. I don't know why that is. The focus with ADUs, like it is the most expensive of the four options. You wanna find a house. got a good basement with a side exit or a backdoor exit. You pop a mother-in-law suite in there. Now you've juiced your property value up and you can refinance. You can rent out both units. Now you're cash flowing over a thousand bucks a month. It's beautiful.
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:more in a duplex, and now you can refinance that sucker and get most, if not all of your money. Back out to do the next one with Scott. Right, and you can, it's called B
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:You buy, you renovate your rent, your refinance, your repeat. It's just a circle.
Scott Dillingham:And to further add to that and you nail, you nailed it actually. And, and that's what we tell investors to do. And from the financing standpoint, we'll structure it as a mortgage plus improvements. So we'll actually have the lender give the client the money for rentals so they're not using it all themself. And so by forcing that appreciation, like you said, you can then refinance faster and you've got funds.
Rhys Wyn Trenhaile:the way, I wanted to prove that I wasn't just another Johnny Cum lately real estate agent saying the same damn thing. So we just did a video, me and Sadie on YouTube, and one of the guys said, hold on. of the guys said, it's a doctor, doctor, investor. I'm, and he is not our, we're just winning him over from another group. I'm not gonna say who, but this was his comment and this won him to us earlier this week. I'm more impressed with the flat out honesty. I don't buy condos. There are, don't buy condos is something I never thought I'd hear from a salesman, period. What he is talking about is we identified only three good. Condos to buy as income properties out of 179 currently for sale.
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:what he heard in that message, which was what, not what I was trying to convey was, most condos don't invest in them. Talk to Sadie. You wanna get one of these three. And it's like that on a regular basis right now. So what I was trying to convey was Sadie really knows what she's doing. She really knows what to put you in. Like there's a lot of condo buildings you do not wanna invest in. They're not run well. Right.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:They're behind on the reserve funds or, you know, they, there's a huge engineering thing coming up. But also like, which one's actually cash flow, which ones are gonna be nice, steady investments for that doctor, for that, that account. The, the professionals, they gotta be able to sleep at night. You can't sell them before Plex in a poor area town. just, you just can't, you can't do that to them. So anyway, I just wanted to point out right that. That's what it is. And I said, back to this guy, I said, if you invest with us, know, we treat you like an adult. We give you the good, the bad, the ugly. We make you. We let you make a sound decision. We provide the same advice we use ourselves and well, we now have teammates with Lamborghinis. We have clients retired on Manchester Lakes, and yet people will still get on Facebook and tell us, we don't know what we're talking about.
Scott Dillingham:Mm-hmm. Those are the haters though.
Rhys Wyn Trenhaile:with,
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:cash flowing properties in a major city in Ontario, I'm telling you, this is it. You got Scott for the finance and you got us for the sales and we're not gonna lead you astray. We even have a human greed factor in you getting you wealthy. The more income properties you buy, the more commissions we get to buy our own income properties. So your
Scott Dillingham:Mm-hmm.
Rhys Wyn Trenhaile:is more money for us. So, why on earth would we wanna sell you a junker? As soon as we sell you a junker, it's over. We won't be able to sell you anything else. Even if you stick with us for another four or five years,
Scott Dillingham:Yeah. People don't think of that.
Rhys Wyn Trenhaile:want you to get
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:So you're buying more and more and more faster and faster and faster. Bigger and bigger and bigger.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:there is a capitalist pig greed interest there as well, man. So we're
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:We're here. Scott's here, I don't know. Not too many people don't get it buddy. Too many people don't
Scott Dillingham:For sure.
Rhys Wyn Trenhaile:be yelling a little bit. Try to
Scott Dillingham:Yeah, no, that's,
Rhys Wyn Trenhaile:on your podcast, bud.
Scott Dillingham:that's okay. But it's true. It's true. There's so many realtors that are just looking at getting, you know, as bad as it sounds, you know, food on their table. Now they're not looking at building those long-term relationships. Yeah. It's.
Rhys Wyn Trenhaile:just got, yeah, we are. Yeah. I'm not gonna get into it, but Yes.
Scott Dillingham:You know, there, there's people out there that are like that, right? And, and when you hire them as a
Rhys Wyn Trenhaile:podcast, but Yeah.
Scott Dillingham:Yeah,
Rhys Wyn Trenhaile:far too common. Far too
Scott Dillingham:yeah.
Rhys Wyn Trenhaile:Yeah.
Scott Dillingham:And a realtor will never, they'll never tell you that. But, but I know just from your team's track record and how long you've been in business, it's not how you guys operate. I.
Rhys Wyn Trenhaile:like one other real estate agent doing income properties in Windsor that doesn't plead out clients to us because they're doing that to their clients, either through their own sort of inexperience or. they're not landlords themselves, so they don't know the nuance.
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:yeah, I mean, and it's constantly like the only time we see that bum tenant, you know, that's not paying rent for six months we gotta unravel that. The only time we ever see that is when we inherited client from somebody else and we gotta solve the problem. We didn't create the problem, man, but then we gotta solve it. And you know, if you can pull the thorn outta the tiger's paw, they're clients for life, right? So we always work hard at those.
Scott Dillingham:That's it. That's awesome. No, I love it. I love it. So what we're gonna do, we're, we're gonna cut for today because we we are over time a little bit, but, guys, we're gonna have Reese on. We're gonna have him bring his energy, his team on. Again, we're gonna talk more about the commercial properties, stuff about the team. I'd love to hear about CD's. Six Plexes she's doing right.'cause again, those programs you can finance up to 95%, which is just massive.
Rhys Wyn Trenhaile:get Sadie on, man.
Scott Dillingham:yeah.
Rhys Wyn Trenhaile:Now that you have those pre-approved designs from the federal government, what that ultimately means, guys, is the local bureaucrats can't stop you from building it if you're
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:it. Step aside, boys. Yeah.
Scott Dillingham:Yep.
Rhys Wyn Trenhaile:I got my pre-approval from, from the federal government. Right? What are they gonna do? Nothing. They
Scott Dillingham:Yeah,
Rhys Wyn Trenhaile:anything. Yeah.
Scott Dillingham:yeah. I, I just got one client confidentiality, so I won't give names or addresses, but triplex in Southwood Lakes and, you know, Southwood Lakes, they don't have triplexes there. I.
Rhys Wyn Trenhaile:No,
Scott Dillingham:He's, he's got it approved and he is starting to build and I'm like, wow. So that's'cause government, right? Doug Ford saying Yes, you can build three, three units now. Right. Everywhere. And that is, is helping in this case, right?
Rhys Wyn Trenhaile:the provincial government fourplexes a right because we tend to follow British Columbia.
Scott Dillingham:Yep.
Rhys Wyn Trenhaile:British Columbia brought it in I think about eight, eight months ago. And we tend to
Scott Dillingham:Nice.
Rhys Wyn Trenhaile:BC but we tend to adopt. And hopefully this is a story for another podcast. we adopt what British Columbia did with their landlord tenant tribunal.
Scott Dillingham:Hopefully,
Rhys Wyn Trenhaile:Now let's talk about that next time. That's a really good topic. If anybody
Scott Dillingham:for sure.
Rhys Wyn Trenhaile:about that because Scotty's gotta hang up the phone here, guys,
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:you know, just message me and I'll, I'll send you the video we did on that recently on our YouTube channel.
Scott Dillingham:Perfect. Yeah, so you're right, we do gotta run, but how do they message you? How does somebody reach out to you?
Rhys Wyn Trenhaile:I don't know how this works, man. Can you link our YouTube channel and our
Scott Dillingham:I'll link it in the show notes. Yeah, but you can, you can state it here as well for those that are listening in the car.
Rhys Wyn Trenhaile:So anybody who's listening verbally the, the easiest way to reach out to us is through our website, the vanguard team.com. The
Scott Dillingham:Nice and easy.
Rhys Wyn Trenhaile:like a car guard, stand on guard for the team. There's no
Scott Dillingham:Yeah.
Rhys Wyn Trenhaile:There you go.
Scott Dillingham:That's awesome.
Rhys Wyn Trenhaile:it like that before.
Scott Dillingham:Yeah. Well, I've got a son who's like 10 and he's into anime, so whenever I hear Vanguard, I think of like these robots with shields and massive protectors, and I feel like that's what you guys are for the investors.
Rhys Wyn Trenhaile:Well, so the Vanguard is also the lead ship in a convoy.
Scott Dillingham:Okay,
Rhys Wyn Trenhaile:So I do like to think, I mean, we were the first sort of modern estate team in, in the city, which somebody
Scott Dillingham:Okay.
Rhys Wyn Trenhaile:me of the other day. I hadn't thought about it in a while, but yeah, like we've been, we've been a team in a modern, sort of North American sense for 20 years,
Scott Dillingham:That's awesome. That's incredible. Incredible. Awesome. Well, sounds good. Thanks so much Reese. Great having you on. We'll put your details in the show notes as well for everybody and stay tuned for the next episode, guys.
Rhys Wyn Trenhaile:right. Thanks for having pal. it
Scott Dillingham:No problem. Take care. All.