In this episode of That Real Estate Tech Guy, host Jordan Samuel Fleming sits down with Chris Prefontaine of Smart Real Estate Coach to unpack how creative financing can be the ideal starting point for new and aspiring real estate investors. Chris shares his 34-year journey through multiple market cycles, how the 2008 crash pushed him to build a family-run, no-banks, no-personal-guarantees investing model, and why his Three Paydays system creates long-term wealth instead of “just another job” like traditional wholesaling or fix-and-flip. Along the way, they dive into the importance of mentorship, staying focused in a shiny-object world, using technology and AI to scale (from CRMs to AI call coaching), and building a business model that actually fits your personality and lifestyle. Chris also reveals how listeners can access his free books, Deal Structure Sunday trainings, and other resources to start mastering creative real estate in any market.

About Chris Prefontaine

Chris Prefontaine is the Chairman and Founder of  Smart Real Estate Coach®️, a 4x best-selling author. He is a Forbes Business Council Member and a 3-time Inc 5000 Honoree for Fastest Growing Company. Wicked Smart Community operates all over North America and has successfully completed hundreds of transactions. Chris hosts the Smart Real Estate Coach ®️ Podcast,which ranks in the top 0.5% globally.

Important Links

Watch & Listen

• Smart Real Estate Coach – https://smartrealestatecoach.com/
• Free Books – Visit WickedSmartBooks.com/jordan for Chris’s free books.
• smrtPhone – Claim 5,000 free minutes, the phone system built for investors.
• ThatRealEstateTechGuy.com – All episodes + exclusive tech discounts.

I can tell you one thing: technology is the single most important aspect of every business that has successfully scaled. It’s time for That Real Estate Tech Guy. It’s your weekly chance to explore how technology can help your real estate business explode. Each week, you’ll hear from real estate investors who have been there and done that and find out their favorite technology tips.

Listen in as Jordan speaks with tech companies and learns about new technologies and new ideas that will help you scale your business. And now, join your host, Jordan Samuel Fleming, CEO of smrtPhone, for this week’s episode.

Hey everybody, and welcome to this week’s episode of That Real Estate Tech Guy. I’m your host, Jordan Samuel Fleming. And I have to say, this is a bit of a virtual episode. The next couple may be a little virtual because I am traveling, and rather than just stop… well, here I am. Anyway, I’d like to say that this week’s guest was really great to speak to: Chris Prefontaine from Smart Real Estate Coach.

Really very switched on, very focused guy, diving into the creative financing side of real estate, which is something that we really dig into and explore: why it’s something that newer investors should look to. It really opened my eyes, I’ve got to say. And clearly, Chris has a very focused approach and has huge experience there. Listening to how he and his company and his coaches bring people into that process now was fascinating.

I think it sounds like a fantastic opportunity. I learned a lot, and I think you’re going to really enjoy this episode. I’ll shut up now and let you get right into the conversation I had with Chris. Do stay to the end, where Chris has some amazing free giveaways for you as well. Let’s head over to the show and my live chat with Chris.

Chris, thank you so much for joining That Real Estate Tech Guy today. Before we begin our chat, can you give the listeners a little introduction to yourself?

Yeah, yeah. So I’ve been in real estate 34 years. I won’t bring you through all of that – I’d put everybody to sleep, Jordan – but I’ve touched a lot of different niches out there. After the crash of ’08, I’ll say the market change of ’08 in a big way, that was the impetus to do what we do today. So I’ll fast forward to today. We’ve been a family company – myself, my son, my son-in-law. We do our own real estate deals where we don’t use banks, we don’t put down gobs of money, we don’t sign personally ever. It’s all creative financing.

We then coach and mentor and do deals with students all around North America doing the same thing. So we don’t just say, “Here’s a program, good luck.” We actually do deals with them. We’re in about 80 markets or so right now, and again, they’re doing the same thing: no banks, no signing personally on bank loans, no using gobs of real money. That’s kind of how we fast forward through the 34 years, but I can go back to any piece of that if you want.

Well, actually let’s stay at the present for now, because one of the things I see is that a lot of people get into real estate investing and obviously they get there… they see a webinar, they see an event – you know the story that everybody goes through. Creative financing tends to come in the middle of the journey from what I have seen. It’s not something that I’ve seen a lot of people who are getting started really understand.

Given that that’s your focus today, maybe let’s hone in a bit on why that’s such a relevant thing right now, why it’s such a good thing, so that people who maybe have heard about it can understand how they take the leap. What’s involved?

Yeah, this is very, very well put because… a couple of reasons. One is people are out there – and this isn’t in any priority order, just things I’m thinking of because you nailed a bunch of things really well – people are teaching, “Okay, you’ve got to go learn wholesaling first.” Okay. I like wholesaling, I have a lot of good friends that do it and make a lot of money, but I’m going to say, with the benefit of hindsight, that you’re creating another job.

Fix and flip for a new person can be really tough. You’re also creating another job. I will tell you that a lot of the niches being taught – some legitimately – are teaching how to time certain markets or work in certain geographic areas. The fact is, if you know creative real estate – it’s been around way before me and you and everyone else listening – if you know creative real estate, you don’t care where we are in the market. You don’t care if it’s up, down, or sideways. You know you can operate, and there’s a certain confidence and clarity that comes with that.

When I came out of the crash, for years I was in my own way. I was just messed up financially and mentally. And I said, “Alright, let’s do something that can operate in every market so I’m not up at night worrying about a bank loan or debt or what the market’s going to do.” I don’t care. I really don’t. In fact, when a new person comes in and learns creative, they can be the authority in every single marketplace, literally, if they wanted to, no matter where you are listening from.

So creative is absolutely a way to start. And then you can tack on any of those other basic niches if you want later on. But creative is absolutely the way to go, in my opinion. Of course I’m biased, but I’m strongly focused on that now for all the newbies, because that’s what I’m trying to teach people: start here, understand the skill set, and get your confidence up.

Well, and I think that’s really interesting because so many times when I speak to coaching companies or coaching communities, wholesaling is 100% where everybody starts in most of those communities. I will say I haven’t seen it all the time, but in the vast majority of them, wholesaling is where they start.

And I understand why as well, because in theory it’s a pretty easy model with pretty low input and low risk. There’s just a bit of legwork, right? There’s a bit of graft to it. But I’ve rarely seen people talk about the creative side as a first entry point.

So you said that you actually do have a mentorship or training side of your business. Do you take people from absolute beginners? What sort of structure do you have set up now for that?

Yeah. Two things. One is to go back to your earlier point, and then I’ll go to the avatar, the makeup of who we work with. On the wholesaling side, here’s a very important thing to know if you know nothing about creative. We trademarked what’s called the Three Paydays. Payday One for us is almost the exact same thing as if you did a wholesale deal: “Hey, I did my deal, I’m out of here, now I’ve got to go find another deal.” That’s a treadmill.

Whereas with our Three Payday system, Payday One that we teach you how to create is just like getting that one check. The difference is now you’re in that deal and you have cash flow and long-term income. So I just wanted to distinguish that.

As far as the people: yeah, actually 98–99% of the people that come in have a job somewhere else and no experience in creative. Almost everyone is brand new. Now, do some people come in from other niches like wholesaling and say, “Hey, I want to tack this on”? Sure. But there’s a large majority that come in brand, brand new, and at the same time they’re trying to leave their job. That’s a lot of the people we deal with.

Our program is set up foundationally to bring people from A to Z, literally: you know nothing, you’re at third-grade level, let’s start you off. Let’s bring you through our onboarding. Now, if we find someone gets caught up in that and they’re like, “Hey, I’ve got all this experience, I own property,” we run into that and we say, “Okay, great, we’ll fast forward it, but we’ve got to start at the same level so we’re on the same playing field.” If nothing else, that’s for the vernacular—how we operate, what the three pillars mean, the nuances that we teach and have trademarked. You’ve got to learn them.

Once you do, you’re golden. Then you’ve set that base level of knowledge, that common language, and if you do have a lot of experience in other methods, you can probably push the boat even faster because you’ve got a certain element of experience.

That’s kind of it. To give everyone some background: I was in real estate 17 or 18 years prior to the crash. You’d think that I would know a lot of creative, but I only knew pieces of it. Of course I knew of owner financing and wholesaling and all that, but I didn’t wrap it all together. So if you come in with any kind of base knowledge — you’re a realtor, you’re a wholesaler, you’re a flipper, you own property, you’re buy-and-hold — you do have a foundation and vernacular that I can probably feed off more quickly. But it’s not required.

And so when you say you obviously have a very… I don’t want to date you, but you’ve got a long history in real estate. Before the crash, what was your journey in those 17 years before you made this full pivot? What was that like? Can you give us a bit of a sense of that journey and what you were doing then?

Sure. I’ll go real quickly through it and you can circle back if you want. So in ’91, my dad had a welding supply company and he sold it, and I was supposed to run it. I was the general manager of five brick-and-mortar branches. Well, I got fired after maybe a month. They fired me, and my father was even shocked.

So I left there with kids two and three years old, no income, no nothing. Luckily, I had started building a few homes, so we were building homes in the early 90s. I survived off of that. We went on to build a couple hundred homes. I then bought a Realty Executives franchise—for those of you in the realtor world. I put my realtor hat on; I never should have done that.

I sold that to Coldwell Banker back in 2000. From 2000 until the crash, I was coaching high-GCI realtors, not investors—people that were making money, but their life was a mess, so I was helping them through that process. Then the crash happened, and that’s where I bring you into the story, because that crash from February ’08 to 2012 was a window where I was a mess mentally and financially and couldn’t get out of my own way until a few mentors and trusted business owners said, “Chris, you didn’t take the national bailout. You’ve got to get out of your own way.”

That fed me into establishing some rules that I would never sway from, and that is how we operate today.

No, that’s great, because I think it’s always interesting when you’ve got a relatively long history and then you make a pivot. And it’s not a drastic pivot, but it is a refocusing, I would guess. I always find that interesting because in this case there was an external impetus for it. The crash took everything apart. But it’s also very interesting because you see that arc of where you are today, how you pivoted and then built up again.

I think a lot of people in real estate resonate with those sorts of arcs, because almost everybody in real estate is trying to accomplish something. They’re boxed in, they’re trying to get rid of their job, they’re trying to figure out the next step. So I think a lot of people resonate with a story like that, and I appreciate it.

And I think what came to mind when you were talking is this: if you’re listening to this and you go, “Yeah, I’d like to scale, I’ve got to get started now and then I want to scale,” if you’re looking to do that for yourself, I’m biased toward creative, but I’ll talk more generally about real estate. One: get a niche that you go, “You know what? I can get behind that,” because there’s a different flavor and energy to every niche.

Some good friends of mine teach land flipping. You can do it online, you can do it from anywhere in the world. Great, if that’s you. Some wholesalers and flippers have to get houses at 60 or 70 cents on the dollar. Fine, if that’s your cup of tea. Ours tends to be a very win–win, healthy environment, and if that’s for you, great. So pick that.

Second – and there are only three steps here – find someone in that niche that is where you want to be and has already gone through at least two economic cycles, preferably more, and maybe even some personal challenges along the way, because life just happens. If you’re going to hang out with someone or mentor under someone or apprentice with someone, you want to be able to go to them and say, “Hey, I just had this happen. What do I do?” If they’ve never had those experiences, it’s kind of tough.

And I also mean to the extent of their relationships, if that’s important to you: their family, their values. You and I can go out and find someone tomorrow who had huge success but, as a result, wrecked their health or their relationships. So find that person or group that’s aligned.

Third and final is this: put on the blinders for a good three years and don’t deviate to the shiny object. If you do that in any business, you’ll have a great experience. Unfortunately, real estate is being marketed to us left and right, and we’re getting bombarded by “get rich quick tomorrow,” and it throws people off.

Now, I’m sorry to interrupt this amazing conversation, but I wanted to make sure you knew that smrtPhone, the only phone system built for real estate investors, connects to the best-in-class real estate investing CRMs. And because it’s my show and I am co-founder and chairman of smrtPhone, I’ve got some great deals for you.

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I absolutely see the shiny-object problem in real estate, particularly on the investor side. It’s always a problem. A lot of my customer base and a lot of the people I’ve trained over the years are either fix-and-flippers or wholesalers—that’s the majority of what they do. And the amount of times you have to get them to stay focused, even on something as simple as, “Stay focused on the leads you’re working and not just chasing new leads,” is a constant challenge.

And I think your point is really valid in almost any business. If you are laser-focused for a couple of years, your chances of success—unless you’re really not capable—well, if you’re a basically capable person, that focus is going to give you a way, way bigger chance of success.

Yeah, good question. It’s sad to see. I see it in my community, I see it elsewhere in life. It’s sad to see people that stop just shy of hitting it big. I have the opposite happening too, though. All the coaches and I—we have coaches now in the community, not just me—we’re on a text thread, and a particular individual who has had some life challenges, one of our community members, is about to have a breakthrough with a deal.

Now she’s been at it a while. She could have quit several times over, and she kept saying, “This is it, I have to have this.” She’s about to hit a Three Payday deal that’s well into six figures. What if she had stopped three months ago, right? This happens all the time in both directions. So yeah, just don’t give up on yourself. And if you have a mentor or a group, use them to get you through it, because entrepreneurship can suck. It’s not easy. You need someone, in my opinion.

I’d like your opinion on that, on mentors and coaches.

I absolutely think it’s important. In my own businesses—I’m 47 and I’ve had my own businesses for 20 years. As an adult, I’ve never worked for anyone else; before that I was doing a PhD, so that was the university for a while. And I have had mentors the entire way, because you need it. Regardless of how capable you are or how confident you are or anything else, having someone give that outside perspective will keep you on the right track and will stop you before you deviate too far, if you’ve got someone trusted.

Yeah, 100%. I can think of examples. I came out of the crash and, as I just told everyone, it took four years to get out of my own way. One of the many mentors I talked to literally chuckled at the stuff I went through. Then he listed the stuff he went through and I thought, “Whoa, mine is nothing.”

So you just have to pick your head up and look around. I had a guy on my podcast, David Nurse. He trains and works one-on-one with college players coming out for basketball who are making millions. He said, “Chris, what we do is we take one thing they’re trying to work on, we find a person online to model after, and that’s what we work on for a year.”

So my point is that the mentors and the coaches and the people that you can get help from are out there—just go find them.

Well, and to your point as well, I think taking performance another step: a lot of people think performance is a magical thing you either have or you don’t. Performance is honed, and athletes are the best example of this. I remember years ago, there was a cycling team for the Tour de France, and they were talking about how they were looking at fractional percentage increases in performance on a month-to-month training plan.

Those fractional increases added up to the 3 or 4% increase they needed to beat the other professionals. To me, the point was never “Oh, the professionals are working like that.” My point was always that it’s that kind of dedicated craft and training that is applicable to every scenario. If you train and evolve your skills, those percentages add up to wins.

I love it. The quote that came to mind when you were saying that is, “How you do anything is how you do everything.” It’s just habits.

So we see what we’re doing now. We’re talking real estate, yet all this other stuff we’re talking about—why? Because unfortunately it’s not just, “I’ll show you how to do a deal.” You could go on my YouTube channel and look at 500 deals we post if it was that easy.

But unfortunately, it’s not that easy. It’s all this other stuff you and I are talking about: the headspace, the tech, everything.

Yeah, absolutely correct. And I’m excited to be able to get people more information on your programs, because as I said, I genuinely feel like a good 90% of the time, the focus is always on wholesale to get started. Not that that’s a bad thing—there’s no criticism—but I think having other options and understanding what, to your point, is exactly right: find the model that suits you.

Because if it suits you, you’re going to want to wear it, inhabit it, live it. But if you’re doing a model that causes friction, or you get too nervous, whatever it is, you’re not going to stick to it. You’re not going to have those increases in performance and all of that. So I think that point is really valuable—understanding how to find the niche that you really like.

Yeah, I love it. So from a… I’m going to do one little bit of technology with you before we go, because I genuinely want to. I know you’ve got some giveaways as well, and I want to make sure we have time for that and I’ve got to respect your time as well.

One of my biggest focuses when I started this podcast was all these different models. To me, it’s all about building a scalable business. Scalable businesses, to me… at this point I’ve got 65 people in my company, and we’ve scaled up our company. I know exactly how hard it is to scale at this level. I know exactly the pain points.

Technology is the thing that helps you scale a system, and without it, you’re sort of lost. As you’ve gone through your journey, with the different hats you’ve worn in real estate, can you give an idea or a bit of background on where you saw technology being a massive improvement or help, or where it started to impact your real estate journey in a much bigger way?

Yeah, I think about a few things. I’ll go from today and then backwards. Just with AI in general, I’ll give you one little thing that saves hours and hours of work. If you’re in our community, you’re doing live calls, you’re putting them in Slack, and a coach is putting on a headset and listening to that entire call and critiquing it. It is grueling. It is the fastest way for them to improve, but it’s grueling for me and the coaches that do that.

So now we’re training AI to critique those calls. Even if we have to oversee some of that initially, hours and hours are now freed up for the coaches to do what? Do more deals and scale that way for the students. That’s huge.

Going backwards: when we started the coaching company over a decade ago, organically people would ask us for help locally and then it grew across North America. They would have to go out, get a CRM, get a website for 8 or 10 grand, then go out and create some workflow automation—that would be a different system, like Podio back then.

Now we have one system and it’s probably… I don’t want to say a hundredth of the cost, but it’s a couple hundred bucks a month instead of several thousands. It’s our white-label Dubb/REI BlackBook-type setup, but it has the CRM, the website, all the workflows—everything in one system. It’s crazy compared to what it used to be. That’s just one example, but that’s in the trenches in the real estate world.

Absolutely. And the AI point is… so my company smrtPhone, we’re actually in the process of launching an AI agent marketplace where not only can you get one agent, but there’s going to be a marketplace of different agents, including not only call scoring—because your point on call scoring is so valid. Being able to have AI score every single call is a huge game changer for the coaches because there’s no scalability otherwise.

But we’re also building live coaching as well, so that AI can listen to a live call with an agent and actually be giving those hard and soft tips like, “You’re speaking too much,” “Ask more questions,” “Slow down.” You know what it’s like: new people on the phone feel the need to fill the air.

So the AI agent can actually coach them to bring the tempo down a bit. Those bits of technology mean performance doesn’t have to be retrospective; it can actively be on the go in real time. That’s where technology is absolutely crushing it.

Well, before I let you go and before I get you to let everybody know how they can get in touch with you, I do have a couple of key questions I always ask the guests, and I’ll run them by you.

Number one is: can you tell me about the greatest mistake you’ve ever made with real estate technology?

The greatest mistake with technology? Yeah—taking on, I’ll be brief without names, but taking on a technology that was, number one, brand new; number two, not even proven yet. So when it went down, it crippled us. So: research. Let me just put out there—research.

I like that. You can tell me what happened offline.

So the second question I have is, and this could actually be the same answer: if people are just starting to look at technology for real estate, what would your advice be? Yes, research may be one of them.

Well, I tie this one back to the mentor three steps we talked about, because every niche is slightly different. Whoever is the person you’re looking up to in that niche, get their recommendations and then do your own research.

Okay. And the final question is: if someone was just coming to you starting out, what three pieces of technology would you say they should start to work with? I’m going to qualify this in terms of budget. Because when I was broke, I needed a cell phone. So, I know it goes without saying, but from a technology standpoint, besides your cell phone, something like—doesn’t have to be exact—but something like an Asana for tasks and a Slack for communication. Doesn’t have to be those two, but something like that for communication and tasks.

Okay, and just to draw you out a bit further: why those two—communication and tasks? Why is that so critical if they’re just starting?

Because if you’re just starting out, you’re going to get caught up in creative avoidance syndrome. “I’ve got all these pieces of paper…” If you don’t have any tech, anything for flow, you’re going to get caught up in the weeds. Then you cannot do the top one, two or three things you should be doing—which in my world is talking to sellers.

If you’re doing anything else and you’re not relying on tech to handle tasks and communication, then you’re wasting time. You’re a glorified assistant.

Well, and I’m going to follow up with one little thing. My point of advice to people is: don’t do what I’ve noticed some new investors do. They’re scared to go on the phone. They’re scared to make those calls to sellers. That’s a normal thing, by the way—nobody should be ashamed of that. That’s totally normal; Chris is well aware of that.

But look for the mentor that’s going to help you with that. Because what I have seen happen is people start going, they don’t want to make the sales calls, so they start fiddling with their CRM a little. Then they go, “I’m going to create some more reports…” It’s almost like, “I’m going to do my accounts,” just to avoid being on the phone.

So one bit of advice I’d have is: if you see yourself doing that, get someone who can coach you out of it and hold you accountable.

Right. It’s one and the same. And you train new people, so you know how new people are often scared to make phone calls, right? They are. I was. I wasn’t exactly like, “I can’t wait to call this person who’s never heard from me before,” but you can train yourself out of that if you have a good mentor, program, or structure to work off.

Yeah. Here’s a thought for those listening: we have hundreds of live calls we utilize that they get to listen to. I tell them: listen to those until, like when you’re little and you hear a song, you know the next word in the verse because you’ve heard it so many times.

Listen to us on calls until you know what we’re going to say next, and then know that there isn’t this daunting amount of data you have to learn. There are probably ten commonly asked questions and, you know, 15 scripts. Learn those. Just get really obsessed with learning those, and then the rest is fun.

Yeah, and learn how to listen. Learn how to listen so that when you are on a call, you’re not so focused on your next line or whatever that you’re not listening to what that person is saying. Because it’s what he or she is saying that’s going to give you that clue to go, “Oh, there’s my in,” or “There’s the bit of information I can pocket, because that’s what matters to them the most.”

Spot on.

Yeah. Well, listen, Chris, first of all, it was an absolute pleasure to meet you finally in person. Let’s just focus on the last minute or so on you, your program, and how people can get the benefit of what you do.

Yeah. I’m big on free, Jordan, because of all the garbage out there that you and I talked about—all the stuff bombarding them. So I’m big on free. I mentioned in passing: go to YouTube, “Smart Real Estate Coach.” Type in Smart Real Estate Coach. There are many things we release every week, but one is Deal Structure Sunday. There are 400 or 500 deals on there, maybe more. Go watch that.

You can also get my free books—there are a couple of them. And when I say free, it’s not one of those “free” offers where you’ve got to pay shipping, because that’s not free. This is truly free. Go to wickedsmartbooks.com, wickedsmartbooks.com/jordan, and you’ll get those books at our cost, right from this office. We’ll send them out to you.

Then if you want to look further after that, sure, get in touch with us. There are plenty of ways to do that once you get on either one of those platforms.

Awesome. Well, I will make sure that in all of the posts and in the show notes, that link is there for you guys. Please, if you’re listening to this and you’ve got any curiosity around this, check it out—amazing free gifts from Chris.

Chris, thank you so much for joining us today. I really appreciate it, and it was a pleasure to meet you, buddy.

Appreciate it. Thanks for listening to another amazing episode of That Real Estate Tech Guy. Head over to thatrealestatetechguy.com to check out all episodes and get special discounts on tons of awesome real estate technology platforms.