How Glen Sutherland Built a Multi-State Real Estate System (Flips, Rentals & Syndications)

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In this insightful interview, Glen Sutherland shares his journey from buying his first property to building a multi-market real estate portfolio. He opens up about early challenges, lessons learned from mistakes, and how building repeatable systems allowed him to scale across markets. Glen also dives into mindset shifts, creative financing strategies, passive investing, and the power of coaching and mentorship. Through resilience, problem-solving, and a commitment to helping others, he has built both a thriving investment business and a platform that empowers others to succeed in real estate.

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Glen Sutherland (00:00)
So I think one of the things it’s really taught me is, I mean, this might not be quite your answer, but what it’s really taught me is that a lot of things seem like a big issue at the time. And they seem like it’s the worst. You’re dealing with, you know, the city over some tax bill or some, you’re dealing with all kinds of things. And that’s the whole business is dealing with problems. And at the time,

Quentin (00:28)
you

Glen Sutherland (00:29)
They seem like such massive, massive things that you just can’t overcome or it’s just ruins your day or your weekend or you can’t sleep over it. And every time that happens, I like to sit and think about what’s happened. Like maybe go to the backyard first. I have no backyard neighbors and just scream. I don’t actually do that very often, but you get it out, like get your frustration out and then.

once it’s like dealt with, especially is to think about about what you’ve what’s happened and how bad was it and how much did it affect your life? And ultimately, it’s it’s almost always small potatoes,

Quentin (02:43)
Hello everyone. Welcome to the Real Estate Pros podcast. I am your host, Q Edmonds, and I’m excited to be here today. I have another fantastic guest and this guest, listen, he’s a podcast himself, but also an investor, a coach, and I’m loving how, you know, the way that he’s done his business. has been multi-family, single-family, fourplex. Like listen, this gentleman is a wealth of knowledge and I’m so looking forward to us.

looking at things through his lens and not just getting some incredible nuggets from him. And so I want to present to some and introduce to others because some may already know what this gentleman is, Mr. Glen Sutherland. Mr. Glen, how are doing today,

Glen Sutherland (03:25)
I’m doing great. And thanks for having me on the show. This is exciting.

Quentin (03:28)
Absolutely,

man. Thank you so much for being here. And listen, I’m the type, I like to dive right in, make good use of our time. And so I would love for you to tell the people what your main focus is these days. Also, if you can us a little bit of an origin story of kind of how you got started. We love the hero’s journey, And then also geographically where you are. So that main focus, what you’re doing now, the origin story and where you are in the world. So Mr. Glen, sir, you have the floor.

Glen Sutherland (03:57)
All right, so let’s start with the first one. So my main focus, like you just mentioned in the intro, I’m an investor, I’m a coach, I’m a podcaster. So I don’t know, I spend a lot of time putting content out, completely free, know, podcasting, you’re doing the exact same thing, you share a lot of information. I buy a lot of houses, we sell a lot of houses, we do syndicate deals.

Right now my more focus is on either the single-family or the small Maltese like we’re looking at some 20 plaques This is where our focus is right now the kind of when we get into the hundred plus units where we’re syndicating it kind of It’s when they show up, you know It’s it’s when they show up and then you just sort of switch gears and go full into that which is not where we are right now And then I spend a lot of my time coaching. So I do coaching typically with my students every Tuesdays and Thursdays like

nine hours a day, just solving problems, doing deal analysis, setting up structures, just whatever they need. Right. And so it takes, it takes a lot of time, but honestly, it’s, you said, what’s your favorite part about doing this? It’s, it’s that it’s, it’s doing the coaching and solving the problems. It’s, uh, it’s rewarding when you get success, you feel it. Like, honestly, it’s, it’s my favorite part about it. And it’s not me just making that up. And honestly, if I could do anything, that’s what I would just do. But you know,

where I make my money is doing real estate, flipping houses, doing burs, doing rentals, lease options, sub twos, all that stuff. ⁓ That’s where the money is made.

I started off and I bought ⁓ a town home is what they call like a row house. Right. And I was living in that and just out of college and it didn’t work out with an axe. And so I took the house and then I refinanced it. And my parents always had a duplex growing up that I was the labor boy for. So I would be the guy to do all the stuff to get it going. But I realized there’s some equity in the house refinance. I think I pulled it like 40 grand, you know, not light changing, but like

After college, that was a lot of money at the time and I ended up investing that into a condo. And I bought that. It was the worst experience of my life. I didn’t screen tenants properly. They walked all over me. I said, I’d never do real estate again. I sold the house and I got the 40,000 back that I’d put in for my down payment and I got another 40,000 and I sat like that for like three years and said, I don’t know what I’m doing, but there’s something here.

Quentin (06:53)
Mmm.

Mmm.

Glen Sutherland (07:16)
I don’t know what I’m doing, but like there and this is like 20, 25 years ago and I’m like, I don’t know what I’m doing. Right. But anyway, did some research. I honestly got really big into podcasting when it was like brand new and not, not doing the podcast yet, but just like listening. And I had a job where I drove around and I literally like drove around fixing bank machines. So, or ATM. So I was constantly listening to podcasts. I was in my truck all day long, like literally six hours a day.

stop, write notes. Sometimes I hit the record button on my phone to take audio notes and I just soaked it up like the freeway, which is the slowest, longest way to do it. But there’s so much information out there. then I basically I went, okay, I’m gonna. So I bought another house and I bought it with my brother and then I bought another one and then I ran out of money and I borrowed money from my grandparents. anyway, I got up to about six houses and the bank said, you’re done.

Quentin (07:59)
Heh.

Mmm.

Glen Sutherland (08:14)
You’re done. There’s no, you’re not getting another house. And I started talking to, know, could it kind of go into secondary lending? How can I get for this? And then the numbers weren’t working because I was also investing in my backyard, which is an expensive area. And it just didn’t make any sense. And I’m like, I can’t, I can’t figure out how to get this. And I was stuck. And so this is where I, I decided to take the leap. And I started, this is about 10 years ago now.

I started investing in the US. like, I didn’t mention this, but even if you’re listening to some students here and all of this guys, Canadian, he’s gonna be talking about Canada stuff. No, I’m going to talk about stuff that can be, you if you’re talking about investing in a different state, almost all of this, it’s the same. It’s the same. There’s this corporate structures, like the only, there’s a few differences, but like almost all of it’s the exact same. But anyway, I started investing in Alabama, Northern Alabama. And honestly, the reason to invest there, I was down between, I think Kansas city.

Huntsville, Alabama and Indianapolis, Indiana, where I, where I originally thinking I wanted to go into, and this is back 10 years ago. They were saying ever bigger pockets. Everything was like saying those were on the list and they’ve landlord friendly. And anyway, they had all my sort of. But buy boxes and I decided to do Huntsville, Alabama, because it was close to Nashville and that sounded a lot of fun. So not really the best way to pick your market, but I started there.

I used my home equity line of credit. So basically off my house, basically borrowed some money, ⁓ bought a property there and I was stuck. I was done. Like I used the money. I bought a turnkey, which is not like, I just needed to get in. needed to leverage other people’s teams. Like there’s so many better ways to do this. ⁓ Even with my students, I never encouraged them to go that way. But you know, sometimes it’s just the way to get in. I found some people, met some people in Kansas city and

They refinanced that property and turned it into three properties and I got stuck again. And then I sold one of my Canadian properties and started doing real estate properly where we were buying at discounts. We were buying it creatively. We were doing a full renovation. were buying homes that needed a lot of stuff done. We started buying Indy. We started buying more in Alabama and then eventually moved into Ohio and then Florida and then.

Quentin (10:14)
Uh-uh.

Missy, I’m sorry, I’m not sure if you can hear me.

Glen Sutherland (10:30)
Texas and Michigan and basically just replicated everything. I just kept setting up a team. So it would be like, I need two contractors, need two property managers, I need a project manager. And I had the scripts down and I just, I’d interview a whole bunch of people. get the right thing. I’d collect the right documentation beforehand. So I had recourse if they didn’t do what they said they were going to do. And I just built it into a system. like, and what happened was I’d max a team out. So we were doing, ⁓ Western Ohio.

And, know, the team could only handle 10 renovations at a time. So you’re like, okay, I could step on their toes and just fire, hire more contractors and more team members in those same markets. I’m like, that’s not, it’s not fair to them. It’s going to hurt my relationship with them when they see I’m working with their competition. And I said, you know what? Nope, let’s just start another team. And so I just started building teams. honestly, the more times you do anything, the better you get at it. so I just.

started leveraging and we went down, started in Jacksonville in Florida, went down the Palm coast all the way down to Brevard County, bought a whole bunch of properties there. did a lot of, we did everything we did in Florida was flips. When we were doing Ohio, we were doing a mix, but anyway, just turn into a business where we were doing, I think our best year was 43 flips in a year, which, some people are like, it’s nothing, but for me, that was a lot. I was managing it myself.

And I was managing it from a different country. was managing it sitting in my office in Canada with a full-time job. At that point, I had a full-time job working, you know, 40 hours a week plus overtime, usually an eight hour shift that I’d fit in either on Saturday, Sunday, or across the week in the evenings. And I was still managing to pull it off. And what it all comes down to is building good systems, repeatable notifications, like, cause otherwise you’re just going.

Quentin (12:31)
Hmm.

Glen Sutherland (12:53)
You’re just gonna break down and cry because it’s too much stuff going on. So really that’s where it came down to and it started scaling it and as people saw what I was doing they started going hey how do how do I do this? do I teach? And originally it was three people that came up to me at a real estate meetup and they’re like teach us. Teach us how to do all this and I’m like well that’s gonna be a whole bunch of time I’m really busy and then they said here what will each give you?

Quentin (13:12)
Mmm.

Glen Sutherland (13:19)
I think it was like originally 500 bucks and we just sat down and it was almost like a mastermind. came up with a topic, we taught it and it was not really a coaching program, but it was just me just giving answering questions and spilling everything I had. It’s gotten so much more organized than like everything as you do it more times, you build proper videos, do proper, everything gets more organized, but off the start, it was just trying to help people and ⁓

There’s a guy who does a lot of do name drops because I know a of podcasts don’t like that, but there is a guy who does a lot of investing in taxes. And, I got to be friends with him. I invested in one of his syndications. And one thing he told me is like, if you help enough people, it’ll just work out. It’ll just work out. And then, so I just started, I started going to every, started the podcast eight years ago, been doing every single week. And I started going to all the real estate meetups and literally not holding anything back.

sharing exactly how to buy, how to structure, setting up teams. And I just shared the whole thing. yeah, the funny thing was if you overwhelm people with just telling them literally how to do everything, they realize how much work’s involved. And they just say, can you just do it for me? And I was just like, and it was an epiphany because I didn’t, it wasn’t the intention. And I’m like, okay, well now I can, I can scale this. Now I can raise the money. I can, people can come to me and it just, it just.

It just kept getting faster and faster. honestly, the first one, first three properties I bought, if I could go back, I would just skip them all. Those first three, maybe the first four. But in honesty, like you can do this so much faster. it just, if hiring a coach and I’m not saying hire me, like hiring anyone and making sure that they’re going to help you. That it’s not a, you know, there’s a coaching programs where they’re just, it’s a video thing. You’re like,

Quentin (14:53)
Mmm.

Glen Sutherland (15:14)
That’s good. But what you really need is someone to ask the questions to someone to sit down with a deal analysis with you. Someone just like, Hey, you’re like, this is the problem I had. I taught people like, here’s how you do a creative strategy is how you do a three option letter. Right. And so I would give them like the lowest price and offer with two different seller financing options, maybe a contract for deed. ⁓ anyway, it didn’t matter. But the thing is you teach people how to do it. And they, you think they could just go do it. You can tell them everything. You could show them, walk them through the whole thing.

But when they actually get there, they get scared. They get scared. They screwed something up. They didn’t look at a comp, right? They didn’t do something right. And what really separates everything, even when I’m hiring a coach, because I hire coaches too, because I want to get my business finer and more organized and just running better all the time. But you need someone to be able to answer those questions. You need someone to just be looking over your shoulder, give you feedback. And honestly, those little mistakes, they

Compound and they can turn into big mistakes and if you start playing with other people’s money it and if you lose people’s money Then they tell other people and before you know it you can’t borrow other money. So it has to work out and honestly That’s why I keep extra money. I never spend my last penny in there because sometimes it just you have to bail the project out and make sure it’s right and that why that way that same person will come back and that you know

Quentin (16:16)
Mmm.

Glen Sutherland (16:43)
because it’s so much easier to work with the same people over and over again. It’s about making it right.

Glen Sutherland (00:00)
So I think one of the things it’s really taught me is, I mean, this might not be quite your answer, but what it’s really taught me is that a lot of things seem like a big issue at the time. And they seem like it’s the worst. You’re dealing with, you know, the city over some tax bill or some, you’re dealing with all kinds of things. And that’s the whole business is dealing with problems. And at the time,

Quentin (00:28)
you

Glen Sutherland (00:29)
They seem like such massive, massive things that you just can’t overcome or it’s just ruins your day or your weekend or you can’t sleep over it. And every time that happens, I like to sit and think about what’s happened. Like maybe go to the backyard first. I have no backyard neighbors and just scream. I don’t actually do that very often, but you get it out, like get your frustration out and then.

once it’s like dealt with, especially is to think about about what you’ve what’s happened and how bad was it and how much did it affect your life? And ultimately, it’s it’s almost always small potatoes, even massive things. You’re like, you know, maybe it’s some money. Maybe I didn’t get as much cash flow this month. Maybe it’s whatever. Like things break. Things happen. People don’t do what they say they’re going to do. ⁓ And

A lot of it, it’s, if you can learn from that, you, I think I’m a stronger person and I am open to dealing with bigger issues and bigger problems. And a lot of people have a hard time with that. had a business partner that it just, they couldn’t even sleep. They like, can’t do this. And it wasn’t big thing. It was back in the early days. And it was just that the, the tenant was moving out and we were going to have to go over there ourselves. Cause we didn’t have property manager back then.

And we’re going to have to go empty the place out. And that would keep them up at night. Like just the thought of that. And you start thinking about like, that’s, that’s nothing right. Or hire somebody when you’re like, but then we won’t cashflow for a month or something, but it be a little speed and you’ll get the tenant. Like a lot of it is just looking bigger picture. And if the harder part is if you’re working with partners or money partners or other joint ventures or however you’ve got this structured.

is sometimes it’s everything to them. They have this one property. And so it’s a win or a loss. There’s no middle ground. And once you get a little bit bigger, and as you can spread this across a lot of units, then it’s, hey, we have to replace a furnace. You’re like, it’s going to cost us like six grand or something, or five grand, depending what. ⁓ But it’s going to cost us some money. But overall, we have

more than that coming in every month, far more than that across all these properties. it makes it a lot easier, but if that’s your one and only property, it’s tougher. So I think that’s one of the things I’ve really learned. It’s really changed even my perspective on this. you get first really negative and then you with yourself and your business. And once you get more comfortable with problems and adversity, you get more used to it and you get better. Deal with it.

Quentin (02:57)
Yeah.

Yeah.

Yes,

sir. It’s like that building that muscle memory. You get to the point where you have dealt with things that overcome some adversity so much. Now the solutions is kind of like muscle memory. You’re like, no, I know how to do this. And it’s almost again like that 10,000 hours that you put in and makes you become an expert. When you’ve been doing it for so long, things just start to come more easier to you. And so I definitely hear you, man. And I think that’s incredible.

I would love to know Mr. Glen, like, what are your next real goals? Like, what are you looking to solve with scale next, man?

Glen Sutherland (03:56)
Well, honestly, this is going to sound crazy because it’s not what most people are thinking. It’s a lot of work to run a lot of units, even with property management and everything. Even when found it’s, you send an email and you think you’re going to get a response, but it’s like following up on your own email. It just wears a lot of time on you. Like I said, this is going to sound crazy, but where my…

goal is and when I was sitting my vision board for this year is I’m planning on selling some of the units and moving the money into investing in my students in more of a passive role. I’m still already helping them with I already understand their underwriting. I already understand the whole projects and there are a lot of people when they start their problem is raising the money and getting the money to do this and honestly most people think that’s the the be all end all real estate but no really the hard part is finding the deals.

but they’re actually a really good deals. where, what I would like to do is, ⁓ you know, I still want to have a whole bunch of active real estate. I still want to be doing flips. I still want to be doing BRRRR. I still want to syndicate deals and buy apartments, but a little bit less more on the coaching and then, but I’m already part of those projects because I’ve helped them help them with the underwriting and just invest in the projects. ⁓ just to make it so that I’m not the one running it so that there’s someone else’s eyes that, and it’s someone that I’ve trained.

So they know how I do it so that they’re, you know, checking this, they have the followups, they have the same checks and balances. So it’s like, I can, like, if I have a log into their portal, I could see exactly how it’s going. And I, I understand it. It’s just cause it’s, I trained them. So it’ll be a lot easier. And I think it’s a win-win because then people are like, I want to do that because I’m, he’s looking to put, deploy money that

Quentin (05:43)
Yeah, man. love it. I think everything you talking and the strategy that you’re implementing and about to put into place is gold. And I just love your through line. I really want to educate and coach people. And I can just hear that is that you want people, you want to, you want people to be as good as you, if not better. And I think that’s very rare to hear. And that’s what I’m leaning because like you said, you want to be able to be there for other people and coach them and make them better. And so.

I absolutely love it, And if someone wanted to reach out to you, if someone wanted to collaborate with you, contact you, learn more about what you’re doing, how can they get in contact with you?

Glen Sutherland (06:21)
So I have a podcast if you want to just like listen to me interview people. There’s always that ⁓ at Canadian investing in the USA is the name of the podcast because literally what I do. And so that’s probably the easiest way to get a hold of me. But I do have the domain at canadianinvestingintheUSA.com. have glensutherland.com. You can literally go there and most people don’t have this either. You can just click book a call and it’ll give you a 15 minute call.

And my call, could be just answering a couple of questions. It could be pointing you in the right direction, even giving you a lender. could be whatever. It’s not a no pressure call. ⁓ And it’s, you know, if you don’t want to do it, no, no pressure to either. But I’m here to help. right. And even send me an email, which is all the information’s on my websites and I will respond and ⁓ yeah.

Quentin (07:07)
Yeah.

Awesome. Man, I thank you so much. I want to say three things to you. First, I want to thank you for your time, because you could have been anywhere in the world, but you’re here. So thank you for your time. I think you and I both know you can put a premium on your time if you want to. So people will pay you for your time. So thank you so much for your time. Secondly, thank you for your story. Thank you for your authenticity. Thank you for taking time to walk us through to where you are now. I tell people all the time, I put a premium on stories. I believe stories have a way.

of planting a seed in somebody. And we may never see the growth. We may never see the growth, but that seed was planted and it kind of starts them to kind of course correct or give them an idea or give them an aha moment. And so I know your story was impactful today. So thank you for your story. And lastly, thank you for your perspective. Thank you for your mindset, like the way you think. Thank you for bringing that mindset to this platform. I really appreciate you, Mr. Glen. Thank you for being here today.

Glen Sutherland (08:13)
Thank you for having me. I really appreciate it too. These are great questions.

Quentin (08:17)
Absolutely. Appreciate you, sir. So listen, y’all heard Mr. Glen. You got the value. You can’t tell me you didn’t. Look in the show notes, get in contact with him, but definitely make sure you are subscribed here because I keep telling you, we’re going to keep bringing up amazing people just like Mr. Glen. So sir, thank you again. And everyone else, listen, y’all have a fantastic day.

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Investor Fuel

How Glen Sutherland Built a Multi-State Real Estate System (Flips, Rentals & Syndications)

Show Summary

Resources and Links from this show:

Listen to the Audio Version of this Episode

Investor Fuel Show Transcript:

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