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Episode 1298: How Business Owners Can Add Passive Income with Creative Real Estate with Chris Prefontaine

SharkPreneur · 2026-07-01 · 18 min

0:00--:--

Chris Prefontaine outlines a fundamentally different approach to real estate investing centered on the three-paydays system - generating upfront compensation, ongoing monthly cash flow, and long-term wealth appreciation from single properties. Unlike traditional wholesaling, fix-and-flips, or wholesaling that create one-time paydays, Prefontaine's model uses creative financing structures (owner financing on free-and-clear properties, lease purchase agreements with minimal deposits, and subject-to financing on existing mortgages) to acquire deals without personal guarantees or substantial capital. The system addresses current market constraints where tightening bank lending has created gaps between buyer ability and seller expectations. For business owners seeking supplementary income, Prefontaine demonstrates that three to five hours weekly can generate additional revenue through just a handful of deals annually, given the average deal range of $45,000 to $350,000. He emphasizes that success requires patience and commitment rather than chasing quick-win narratives, advocating for a three-year runway before expecting meaningful results. The Smart Real Estate Coach operates in 82 markets and has published multiple bestselling books including Real Estate on Your Terms and The New Rules of Real Estate, while maintaining a podcast featuring both solo content and community member stories.

Key takeaways

  • →The three-paydays system eliminates the need for personal bank guarantees and large capital by using owner financing (principal payments to free-and-clear owners), lease purchases (with $10 deposits), and subject-to existing financing on properties with rates below 5-6%.
  • →Business owners can generate $50,000-$100,000+ annually in supplementary income by completing just 3-4 deals per year while spending only 3-5 hours weekly on the business.
  • →Creative deal structuring has become increasingly valuable as traditional bank financing tightens, creating a gap between seller expectations and buyer financing capacity - making this skill set in high demand across 82 markets.
  • →The biggest barrier to success is unrealistic expectations fed by social media narratives promising quick wealth; sustainable real estate success requires 3+ years of commitment rather than overnight results.
  • →Unlike one-time transaction models, the three-paydays approach provides upfront profit, ongoing monthly cash flow, and long-term wealth building from the same property deal.

Guests

Chris Prefontaine

Topics in this episode

owner financingThree Paydays SystemSubject-To FinancingLease Purchase AgreementsCreative Real Estate FinancingReal Estate on Your TermsThe New Rules of Real EstateDeal Structure OvertimeSmart Real Estate Coach PodcastFree-and-Clear Properties

Questions this episode answers

How can you buy real estate without using your own money or getting a personal bank loan?

By using owner financing with free-and-clear property owners (paying principal, not interest), lease purchase agreements (requiring only $10 deposits), or subject-to existing financing on loans below 5-6% interest rates - none of which require new capital or personal guarantees from the buyer.

How much time per week does it take to do 3-4 real estate deals per year as a side business?

Approximately 3-5 hours per week, either through making 5-6 seller calls weekly yourself or delegating calls to a virtual assistant and speaking only to qualified prospects.

What is the three-paydays system and how is it different from wholesaling or fix-and-flip investing?

The three-paydays system generates upfront profit at closing, monthly cash flow from the property, and long-term wealth appreciation - versus traditional models where investors get paid once at sale and must restart their income pipeline each month.

What are the biggest misconceptions people have about creative real estate investing?

That it sounds too good to be true or that you can't possibly acquire real estate without money down; in reality, these financing structures have been used for decades and simply require understanding how to structure deals differently than traditional bank lending allows.

How much can a business owner realistically make adding this as a passive income stream?

Deals typically generate $45,000 to $350,000 in combined paydays, meaning 3-4 deals annually can easily generate $50,000-$100,000+ in supplementary income alongside a primary business.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

real24estate24deals16deal14seth12show11money10free10three9paid9number7back7chris7rules7podcast6book6

Episode notes

What if a single real estate deal could generate upfront cash, monthly income, and long-term wealth without relying on traditional bank financing? In this episode of Sharkpreneur , Seth Greene interviews Chris Prefontaine, Chairman and Founder of Smart Real Estate Coach®, who shares how he rebuilt after the 2008 real estate crash and developed a creative-financing approach to investing. He explains his Three Paydays system, designed to generate upfront income, monthly cash flow, and long-term wealth from a single property transaction. Chris also discusses owner financing, lease-purchase agreements, subject-to-existing-financing deals, and how business owners can use real estate to build an additional income stream. Key Takeaways: → One property can generate multiple income streams. → Owner financing can replace traditional lending. → Existing low-rate mortgages can create deal opportunities. → Tight lending drives demand for creative financing. → A few deals can have a meaningful financial impact. Chris Prefontaine is the Chairman and Founder of Smart Real Estate Coach®, a 4x best-selling author, a former Forbes Business Council Member, and a 3-time Inc.

Full transcript

18 min

Transcribed and scored by The B2B Podcast Index.

Welcome to the Sharkpreneur podcast with Kevin Harrington and Seth Green. Kevin Harrington is the inventor of the infomercial, one of the original sharks from the hit TV show Shark Tank, and has generated over $5 billion in TV and digital direct response sales. Seth Green is the world's first trusted authority on cutting-edge direct response marketing, a best-selling author, and the only three-time Marketer of the Year nominee. On the podcast, Kevin and Seth interview Sharkpreneurs, who share straight talk on what it takes to explode your business.

49 faces look to him in triumph. Over the last 12 months, they had each taken turns and promoted his business for a week at a time, driving over $987,342 in revenue. What if you had a network of 50 centers of influence who promoted your business every week for a year? Grab your copy of the number one Amazon bestselling book, The Ultimate Guide to Growing Your Business with a Podcast.

At 33% off the Amazon price by going to ultimatepodcastbook.com. Again, that website for 33% off the Amazon price is ultimatepodcastbook.com.

Welcome to the Sharkpreneur Podcast. This is your co-host, Seth Green. Today, I have the good fortune to be bringing back a very favorite repeat guest. He hasn't been on in a long time, but he's up to some cool new stuff.

And we've been working together for, God knows, not 20 years, but close to it. So Chris Briefontaine from Smart Real Estate Coach, he is a multiple-time best-selling author. He is a podcaster. He has built an incredible community and business helping people achieve financial freedom through real estate investing, but not the way you've thought about it before.

So if you've read any books that aren't Chris's or taken any courses, this is a very different approach. one of which I am a big fan of myself. So Chris, thanks so much for joining us. Thanks for having me back, my man.

We just got to do a little tighter on the schedule so we can get together more often. That is fine with me in addition to our weekly normal calls. So for folks who didn't hear the episode that was like six or seven years ago or however long it was, give us a short version of kind of your story and how you got to be where you are, because you went from, I think, completely broker than broke, underwater in the real estate space to incredibly successful. Yeah, so in New England style, I'll do 34 years in about two minutes, three minutes.

And then you can peel back any piece you want, Seth, as always. So yeah, I started in real estate in the early 90s, owned a brokerage, built a bunch of homes, all kind of creatively back then, coincidentally. I was only in my 20s. And then leading up to the lovely debacle, the crash of 08, I had 20 some odd properties.

Unfortunately, I was signed on all those personally. So when the market hit the skids, the banks came knocking. That was a miserable time for me from literally like a light switch February of 08 through February of 12. And then coming out of that, I just simply determined, OK, we've got to reset the rules here or we're going to have the same headaches.

And the rules were kind of what you alluded to. They're different. Let's not ever sign personally on bank loans. There's no reason to do that.

Let's not use gobs of our own money. Let's never get paid once on a deal. Most people in real estate said that, you know, they do a flip or they do a build like I used to or they're a realtor like I used to. And they get paid once and they got to do it again.

And then every January, it's a little bit frustrating because you've got to start your whole wheel over again. Well, we decided let's get paid multiple times on a deal. So we did trademark federally the three payday system. And then that organically has taken off.

As you know, I think we're in 82 markets right now, actually doing transactions with students, because unlike a lot of companies out there, we actually do deals instead of sell stuff to people. So that's what we're that's what we're up to now. I can peel back any layer of that, obviously. Yeah, absolutely.

So let's dive into that. So obviously, we don't want you to give away the entire system. And we want people to check out the webinar and the trainings and the books and all of those things. But talk a little bit.

So you mentioned a whole lot of things that were really important. You the traditional real estate investing deal, you get paid once, right? I buy a property and at some point I sell it and I get paid or I do a fix and flip. And my profit margin is what the increase is minus what I spent to fix and flip So why in your opinion is that kind of broken And why is yours so different Broken for a few reasons As far as the one pay and I'll talk about in general, as far as the one pay, here's what I've seen.

Definitely since I've been on your show last time too, we've helped gobs of people go from corporate America to our system, right? And do real estate deals. Whole bunch of them. Once I dug through a bunch of layers and got to know more said yeah i tried to do you fill the blank could be wholesaling fix and flip i've got friends to do it all so i'm not pooping it but the fact is is they were at a job and then they created another job because all it was was do a deal get paid do a deal get paid and they couldn't do that like it's not sustainable so then they finally stumbled upon us and boom they leave the job in 12 17 24 months whatever the plan set up so if you and i were going to open a restaurant tomorrow, Seth, and I said to you, hey, I got a cool system where you can get paid up front and you can get some monthly cash flow for your restaurant.

And then you get some long-term money too. You and I'd be like, that's a cool entrepreneurial model. Well, that's what we do with properties. That's all it is.

It's upfront money, just like everybody's used to getting paid when they do a deal. And then it launches a cash flow stream and it puts in place this longer term cash flow as well, a wealth building component, if you will. Here's the other piece of what's broken and there's a little different than your question, but right now what's going on in the market? Banks are tightening, right?

So these poor buyers are getting kicked to the sidelines and the sellers are like, well, I don't want to lower my price. So you have this gap and the deals aren't shrinking. People's ability to structure deals creatively is just not there. And so that's what we're on a major mission to, I'll say, get the word out much more quickly, much more effectively, because there's never been a need in my 35 years.

This September will be 35 years than now for creative with all those things going on in the peripheral. So that makes a ton of sense. So let's talk about that. So you also kind of controversial in the real estate space because you tell people that not only should they not sign personally, but they shouldn't be dependent on like bank financing.

So talk a little bit more about where they're getting the money from to do these creative deals? Yeah. So I don't want to say out of thin air, right? But we're going to show them how to structure a deal where they can buy it one of three ways.

Owner financing, whereby the owner becomes your bank. And we specifically focus, niche down with owners that are free and clear. Those owners are great to deal with. They want the most money, but they'll take it over time.

So free and clear owners, owner financing, where we're making monthly principal payments to them. Please, if you're listening, listen to what I just said. Principal payments, not interest. I don't care what environment you're in, that's a win.

Second way is lease purchase. All these purchase agreements, Seth, like we have them in our course, they've pre-printed a $10 deposit in there. A $10 deposit to then go out and tie up millions of dollars worth of real estate just on a lease purchase arrangement. And then third is subject to existing financing.

That's being taught correctly and incorrectly at a mass scale right now. And there's about 60% of the loans out there that are still well below five and 6% that we can show you how to chat with them and help some of those owners out that unfortunately have to do something even though they have a low rate on their house. So that's how we buy. No new money coming to the table with those I just said.

I mean, maybe to close a couple thousand dollars or a thousand dollars, but you're not talking tens of thousands of dollars. Okay. Now you had mentioned about people building a specific time plan in terms of months or short period of years to get out of the corporate rat race and do this full time. How a lot of our obviously great percentage of our audience is business owners.

So how can our business owners use this to build up a second stream of passive income beyond to supplement their primary business? Yeah, I like using, instead of things I think of when you said that, was there's an attorney in Arizona. He mostly deals with trust and estate planning. And he said, Chris, I don't want to sell my practice.

I don't want to leave my practice. I don't dislike it. I just want to tack this on. So his goals are far different than you coming to me and saying, hey, I need to replace a half a million dollars in income.

Show me how quickly. And that's what we get a lot. So his is, show me how to do three or four of these deals a year. And that's a huge win.

And let me say why. Our three paydays now that we had the history we had doing this in the 80 markets run from low to And somewhere in the middle is a strong average So you talking six figure deals on a lot of these deals Many people I talked to don't need to do 30 of those deals next year. They need to do a handful that really change their financial future, especially if they have another business going on. Absolutely.

That makes a ton of sense. And then the next question they're going to get is I'm already too busy running my business or businesses. And I know it's going to vary all over the map, But how much time does someone spend doing your systems like part time who doesn't need to replace a multiple six figure a year income, but it's just looking for, hey, I want to make let's just say I wanted to make an extra 50 or 60 grand a year. Yeah, tinkering.

I mean, 50 or 60 grand, I'm going to facetiously say is pretty tough, meaning to like, because if you do one deal, you hit that, right? So it's actually pretty tough to go. But the answer is probably, gosh, that's small, but three, five hours a week. Because when you start, there's nothing you can do except for have, depending on your resources, either have a virtual assistant do your calls and you're just calling sellers that want to talk to you after that.

And that's like five, six calls a week if that's your goal. or if you're doing all your own calls even. You don't have to talk to many people to get to there. And I hate to water it down and say that that's not a lot of money.

It is. But if I just go back to our average of 45 grand to 350, to get you to 50 grand a year, it's not going to take more than a few deals steady with some longer term payoffs that are even bigger. Well, that's a very attractive offer. Tell everybody a little bit because you've written a number of bestselling books.

Talk about the books. Real estate on your terms was done in 17, right? When you and I first met and then we redid it. Coincidentally, we were in the midst of redoing it.

COVID hits and we're like, perfect. Like now we can put all the new stuff in, all the nuances. So that's the most updated revised edition is out, real estate on your terms. We'll give them a chance to get sort of the blueprint, Seth, at the end for free and that'll be included.

And then the new rules of real estate was sort of built after what I said earlier that we rewrote the rules or I did. And then it spawned into all the stuff we're doing. And then what that new rules is, is me exposing everyone to every piece that might touch the creative financing pathway, tax liens, all kinds of creative techniques in there. So I'm not so biased to say, yep, we're it, right?

There's a bunch of pieces that go into this. And so the new rules of real estate was that one. The other thing they'll get, and I'll mention this one more, is the deal structure overtime book. This is cool because this is like, okay, you go on YouTube, you can watch five or 600 deals we post.

We've done that since 2018 on Deal Structure Sunday. But it doesn't tell you always, because it's short, the whole story. Like, what was Seth's real motivation? What happened with his spouse?

What happened, right? All these nuances that we worked through, that's in the Deal Structure Overtime book. Pretty cool. And then talk about the podcast.

Smart Real Estate Coach podcast. Yeah, that's been going on since 15 or 16 as well. I think we're over, I don't know, over 600-ish. That has done some evolving.

As you probably know, as recent as you were on my show and I mentioned it again, and that is we brought on a lot of guests similar to the new Rules of Real Estate book so they can get all pieces of it. And what we got is a lot of demand, a lot of questions, a lot of support to say, A, I want to hear more of you, Chris. So I'm going to do a bunch of solo casts now, at least one a month. And B, I want to hear from your community.

If you've got these people doing deals, I want to hear about them. I want to hear what their job was like. You know, did they hate it? How they get out of it?

What was the pathway like? And what was the first few deals like? So we're doing a lot more of that now. And that starts literally this summer.

So there's going to be a little bit of an innovation on that front, too. I think it's going to be very, very well received because we're only doing it because it was asked for. That's usually a good sign. So with so much noise in the real estate investing space, what are some of the biggest misconceptions people have about, you know, your program and what you're doing?

Because it's so different. Well, to get let me let me say this before they even get to that point, because it's a good question. The misperceptions and the misunderstanding in the market in general is the biggest thing to them because they have this block. They won't even get to me.

Right. And the block is, I mentioned earlier, just in passing, that is, deals aren't shrinking. The ability to structure is shrinking. Banks are shrinking the ability for buyers to buy, therefore sellers can't sell.

And if they listen to the media they never find me because the media is screaming not a good time to buy One of the you know this better than me but I recently when I checked with chat one of the highest searched things in real estate was is this a good time to be in real estate as an investor? No question it was, and it keeps popping up. Well, yes, it couldn't be better. So the misperception with ours is maybe, okay, it's too good to be true, or no, I didn't realize you couldn't buy without money.

How can you possibly do that. Look, I went 17 years thereabouts before the crash without doing this. Right. So I'm, I'm guilty of that.

So I was in that, that school of thought that just must be how you do it. You go raise money or you go borrow money and you sign your life away. I was in that school of thought. And so the biggest misperception is to understand that it is there and let someone show you, guess what?

We're going to give you free resources. If you don't like it, don't do it, but it's going to open your eyes, I promise you. Absolutely. So tell everybody where they can go to learn more, where can they go get the book and the very generous offer that you're making to our audience.

Yeah, so two areas, thank you, two areas. One is just to get sort of the blueprint of everything I'm saying now, this is how you operate in this market, this is why it's under such demand. Just go to threepaydaysbooks.com forward slash SP.

So I know it came from your show. That's the numeric number three, threepaydaysbooks.com forward slash SP. We're going to ship you out a nice package showing you the blueprint of what we do, how we do it with some books.

And it is free, Seth. It's not one of those free offers where you go free offer and I scroll through and you're going to put in eight bucks for shipping. No, free. We'll get it out to you from my office right here.

And then I think you mentioned webinar earlier. Just go to smartrealestatecoach.com forward slash masters class and you'll get it. No one's up breathing down your throat.

Go at your own leisure and watch that. nice replay of a free workshop I did. We greatly appreciate both of those. You've helped so many people for so long achieve financial independence this way.

What's your biggest challenge now? Always. Well, I'm not saying this because I'm on your show, but always the biggest challenge is marketing for us to grow. That's number one.

Number two is, this is a biggie. Because social media is like so prevalent now in their face, especially real estate, but every industry with get rich quick tomorrow, right? It's all over the place. Like the rented cars and rented castles, and this can be you in 10 days.

What's that, what that's done in my opinion is that's had a, has a lot of people coming into real estate. And if they don't have instant success, then they beat themselves up. They think they're affiliate. Like I get this all the time.

No, you're not affiliate. You shouldn't go run to the next shiny object. You should just stick with whatever you think you want to do. And you can get behind and get passionate about for three years.

Then you'll have a good experience. So, so turn off the social media crap telling you that you can do it quick because no niche in real estate, you can do it quick, quick, quote unquote. So that's my biggest challenge right now to get people out of that mindset. It's really managing expectations, Seth, is the short answer.

Your passion is obvious. What do you like best about what you're doing? It's never the same. It's by the nature of creative real estate, right?

So just today, there was a deal put on Slack, which is where our community lives presently. And I saw it and I went, man, I've never seen that. Now I've been doing this 35 years in a few months. I literally called the student, called the coach he's working with that I've trained and said, let's talk about this because I've never seen it.

And it gave us a chance to rip it apart a little bit. So my point is there's deals like that every week that keep me in the game because I get excited about solving. Number one, number two, seeing a new person, and this would have been his first deal, seeing a new person go from zero to one is huge. And then seeing someone go from 10 to 25 is huge, right?

This is like these plateaus. So long answer, but that's what keeps me going. All right. Love the answer.

Love the content. We know your time's incredibly valuable. Thank you for spending some of it with us. This has been Seth Green with Chris Prefontaine from Smart Real Estate Coach.

The link to go get both of those free resources will be in the show notes. Chris, thank you again for coming back. Thank you, buddy. Thank you, everyone, for watching or listening.

We'll talk to you or see you next time. Why do so many businesses struggle while others seem to explode overnight? Do you wish you had the secret to this type of exponential growth? Now, I've scaled more than 20 businesses to over $100 million, and it's not just luck.

In my new book with Mark Tim, Mentored to Millions, you'll learn the repeatable framework I use in all my business ventures for massive success. Order at KevinMentor.com and get over $1,000 in bonuses. head to KevinMentor.

com.

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