This is episode #374, and my guest today is Jack Shea.
Jack is a legend in the real estate investing industry, certainly as it comes to creative financing. He’s an expert at creative ways to use Options in real estate investing, and that’s what we discuss on today’s show.
Of all the deals I’ve done, I personally have primarily bought based on price alone…but there are many ways to make deals work using terms, when price won’t.
Please help me welcome Jack Shea to the show.

Highlights of this show

  • Meet Jack Shea, one of the nation’s leading experts on creative real estate investing.
  • Learn the power of using Options to purchase properties on terms.
  • Join the conversation of how to make deals work by using terms vs. just price.

Resources and Links from this show:

Listen to the Audio Version of this Episode

FlipNerd Show Transcript:

Mike: This is the “Expert Real Estate Investing Show,” the show for real estate investors, whether you’re a veteran or brand new. I’m your host, Mike Hambright, and each week I bring you a new expert guest that will share their knowledge and lessons with you. If you’re excited about real estate investing, believe in personal responsibility, and taking control of your life and financial destiny, you’re in the right place.
This is episode number 374 and my guest today is Jack Shea. Jack is a legend in the real estate investing industry, certainly as it comes to creative financing. He’s an expert at creative ways to use options in real estate investing and that’s what we’re going to discuss on today’s show. It’s some pretty incredible stuff. Of all the deals that I’ve done, I personally have primarily only bought on price alone and try to buy it deep discounts. But there are many ways to make deals work using terms when price won’t. Without any further ado, let’s jump in. Please help me welcome Jack Shea to the show. Hey, Jack. Welcome to the show.
Jack: Hi, Mike. Glad to be here.
Mike: Yeah, yeah, glad to have you back. So you were on the show. I was telling you were on the show a couple of years back, a little about two and a half years ago now, hard to believe it’s been that long. But I have not historically done a lot of creative financing stuff. I’ve bought hundreds of houses, but I’ve not used a lot of creative strategies that when I look back now and think about how many more deals I could’ve done using some of the techniques that you teach, it kind of saddens me a little bit but I’m excited to talk about him today.
Jack: Well, it’s a lot of good dip. Thousands of people, lots of angles, and it’s been good to me. I’ve enjoyed it.
Mike: Yeah, that’s great. Well, we’re going to have you talking about options and different creative techniques, some advanced strategies here, really. Before we get started, though, can you just take a couple minutes . . . you’re obviously a legend in our industry. I’m very grateful to have you back here on the show. But maybe just take a couple minutes and tell us for those that don’t know you yet a little bit more about you in your background.
Jack: Yeah. Thanks. I grew up in Chicago and my parents had some investment properties, and I didn’t know much of what was going on, but they used trusts. And there’s been a trust law in Illinois since 1890. So I got used to that. I went to the University of Illinois. I got a degree in engineering and went ROTC into the Air Force. So I was a pilot in the Air Force for seven years, flying big Globemasters, went out in the world. And I left the Air Force and went into the aviation avionics and flight simulators and avionics business for about 10 years.
So the military wasn’t for me, long-term, and the corporate world. So I decided . . . my parents lived in Florida so I decided to move to Florida and figure out what I do when I get there. So I got a real estate license and started buying and got acquainted with some investors and buying properties into trusts, which were the law in Florida. And then I took some seminars from people like Jack Miller and he was a big option guy. And I took some option seminars and I said, “Wow, that’s for me.” It doesn’t take much money, much talent, much experience, etc. So that’s my bio out there. So I started doing the options.
And it was finding out how they really worked, which was pretty good, but there’s still maintenance and problems and turnover. So after several years, I figured out how I could depreciate properties that I didn’t own, according to the text code I studied. And when the tenant bought it and you were still the owner, I could take $50,000 spread later and do a 1031 exchange without owning it. So that works for me and other things, options don’t have risk if things go bad.
So anyway, stuck to that for many years even when I was making a fair amount of money and could write a check for a house. I just continued to do options. So an option is . . .
Mike: Yeah, and let’s talk about what is it and I want to make sure people that are new to this kind of understand what an option is.
Jack: Well, you know how it’s common in the stock market. It’s common in commodities, business, player options, wise spread. It’s well versed and well established in the law. And it changes a contract between you and me to a unilateral contract if you give me an option for two years for a certain price to come back within two years or by two years and able to buy the property at that price. So it changes to a unilateral contract. I can show up or not show up. I don’t show up, you keep the option money. And if you do show up, we close the deal.
Mike: You have the option. Basis of the word option, you have the option to execute it or not.
Jack: Or. And in a few cases, I’ve passed on options that the property . . . bought a condo, which I know about the tenant committee and this and that. So a couple of busy streets. So just a handful. I probably completed 97% of the options. So the first part in the course, in the book that I want to talk about, acquiring a property on a lease purchase long-term, three years, five years. And in order to get the tax benefits, you have to become the equitable titleholder. So you have to do the maintenance and you pay the taxes and you really have to take control. And if it’s vacant, you pay. And if it needs a roof, you put it up.
But that works for me. I gave tenants an option and I found out that in the ’80s, Mark [Warner] was still my attorney. Seller didn’t pay the rent so evicted him. He got an attorney and the judge said, “You can’t evict a tenant with an option. He has a title right in the property.” And the option confers a right, not a title or interests. So nine months later after the foreclosure, I had to do a foreclosure, I sat down with Mark. And we came up with a contract for option, which solves that problem. So that’s what I do with the tenants.
Mike: Yeah. Well, you’re an engineer, so when you figure out something that doesn’t work, you start to dig in and say, “Well, how can I make this work, right?”
Jack: Yeah. After some expensive seminars along the way, Mike.
Mike: I bet. Well, Jack, let’s talk about an option on the side of you buying. And I know you have tenant options, too. So let’s say for a guy like me that’s met with lots of sellers, thousands and thousands of sellers to try to buy their house, I make a cash offer, usually at a deeply discounted price. And so compare it to that because I think a lot of our listeners understand that traditional model. So let’s say I was to make an offer for somebody to buy their house, and how is this different? I’m giving them an offer now to lease it to me for a period of time with the option to purchase it, right?
Jack: Well, you make a typical, which I have done, we’ve all done, with a low-ball offer for the house and they didn’t like it. So if I come along next, couple of hours later I show up, I say, “You wanted $100,000 and Mike offered $80,000.” I said, “I’ll give you $100,000 for this house.” And the way to do I, I’ll give you $6,000 down. I’ll pay you so much a month and I’ll take over the maintenance and the repairs and on and on and also, you haven’t given me the deed yet. You still control the deed. You have the deed.”
But what I really do, I don’t do this deal unless the deed is in escrow and I put a quitclaim deed. So you don’t end up five or seven years later when that person is not around, have a conversation with their son, who said, “Well, now, this place is worth $300,000 and I’m not signing the deed.” So learn that. So we have an escrow with the title company.
So a lot of people like that for whatever reason. They like the payments. What they don’t like is the maintenance, the management, the tenant, and all that. So I look for unhappy landlords, out-of-town landlords. I have a list, a long list, of where these people come from. And there, found out many years that they were happier than I was, and I counted up. I’m buying down the mortgage, prices are going and buying, getting banking. But I’m thinking about the future. They’re thinking about today. They want to get out. They’re arguing with the wife.
So once we start to deal, I have an autopay and they never hear from me. I mean, I either close or the tenant closes. So they were more anxious to get out of that stuff and I look for out-of-town houses for rent with a different area code. And trying to manage properties from hundreds of miles away while paying somebody. They don’t have the workman. They don’t have the screening capability that we have developed in order to get successful tenants. So I’ve let the tenants buy the house.
Mike: Okay. And, again, are you kind of putting yourself in the middle? You might option it from somebody else and then sell it on an option or you . . .
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Are you kind of putting yourself in the middle? You might option it from somebody else and then sell it on an option or are you . . .
Jack: Well, in one case, I optioned my own home. I mean, I found people looking for a four-bedroom pool home. The owner was not there. He found somewhere else to live. Didn’t need the money from this place for the next place. So he agreed to a long-term five-year option, then I got three extensions and then I asked for a seller carry back financing at the end and sometimes they agree to it. So the whole deal went 13 years, and he was happy enough.
I mean, he would like it cashed out sooner. But by taking the burden, he was out-of-town. He’s paying pool service, lawn service, AC, all this stuff with an empty house and the same with the other people. Excuse me. They don’t like it. They’re not good at it. They may have inherited mom’s house, a former house, they moved out-of-town.
But I have the right to sublease. I don’t tell anybody else that I’m going to live there. I have the right to sublease. That’s where I advertise the house, rent to own, rent to own house, or buy while renting. I put little different bandit signs around and they get to drift, rent to own. They’re buying their furniture that way, probably, or their car and they like it. They’re able to get into a decent house a little bit at a time and buy into it. And we had statistics. They behave better. They lasted longer. The option tenants stayed a little bit longer. They required less maintenance. They don’t spray paint or kick holes in a place they plan to live in. And they were happy campers.
So it took some work with some of them. I screened the tenants through my mortgage lady to see that they could eventually be bankable. Somebody in the house needed a W2 job, not just a handyman and a babysitter. So a nurse, works for the water department, so whatever. And a fairly decent record. But even in ’05 and ’06, a lot of people lost houses. In fact, the properties in Florida went in half.
So they were basically pretty decent people, but they got in a bind. And so they’re good candidates for a seller financing kind of option, tenant/buyer and, well I mean, to buy. And many years later, I started this in the ’80s, I had optioned 50 houses in one year. I’ll go to meetings and I’ll buy all your houses. One woman said, “I have 35 I don’t like or I don’t like this or too much work.”
So I had more than I could chew for three counties. I mean, until I kind of got out the weeds, got rid of some, well, sold some, rented them. But, overall, it’s been a good program, especially with the tax benefits.
Mike: So we’re going to talk about 10 different advanced strategies that you have. You want to jump into that?
Jack: Yeah, Mike, yeah. Being at it for a while, I started using, studying the other applications of options, a very powerful device. And it’s got a lot of benefits in nobody’s harm, but I make loans in an option or I take control of the property or hold beneficial interest, and loan . . . the other fellow’s buying it on terms. Well, he has the option to pay me off or not pay me off. And if doesn’t pay me off, I already have the property. So he has the optional loan.
So I have . . . people doing this class in California and Philadelphia and Florida for years. So a lot of people picked up on that. I got one friend that he uses it full-time and he likes it, and the borrowers are okay. But if they’re not okay, it’s not a year in court on a foreclosure and then the big jam up is it got up to more than two years for a foreclosure. But who wants to spend that amount of time and that amount of money?
So this precludes a foreclosure, the loan. And by using option money to, say, $2,000 a month to extend this option, it avoids usury. Option payments are not interest, okay? Okay. So you want to keep this option and it costs $2,000 a month. So this, I found out different angles to avoid certain problems. But I’ve also been able to use options to change your tax year. If you have, say, a several-year option, you can decide when . . . if this year’s a big year for you, wait till next year. If that’s a big year, wait till the year after. So you can decide when you want to play to pay tax, but if you change it . . .
Mike: Say that again. How do you . . . if you have a . . .
Jack: Say you have a five-year option from me to close on a certain property. So the tenant, your tenant leaves and whatever. Well, I think if you take it now or if you’re giving me the option, you’ll have to pay the tax. The seller will have to pay the tax.
Mike: Okay. Based on the options? You’re saying for the option fee?
Jack: Yeah. Well, because he’s optioning it market value and you probably were in there for less, and you’ll have it for a long period of time. So you can give an option that can’t be exercised for three years.
Mike: I see.
Jack: You know. And so it can work both ways to change when you want it to happen or when you want to allow it to happen. You could say, “Okay. Or next year, after next year, I’m going to be retired and I’ll be in a different tax bracket.” So you can throttle that and adjust it . . .
Mike: So you structure your options to where . . .
Jack: . . . your dates. And people are agreeable. I say, “This is fair if I give you this.” And there’s no surprises or no tricks. And 98% of my business comes from referrals from other business or people. They call, “Can you get this kind of thing for my son-in-law?” or something like that. So anyway, so to differ, Mike, if you had an option for five years on a house that I had, a $100,000 house that you pay $20,000 a year for five years, and you’d own a house. That’s an interest-free loan that you just got. You have a $100,000 loan, like seller financing. But by me offering that to people like that, it’s a fairly good size chunk of money each year. So they pay that in chunks instead of all at once.
And then, at the end, I have gotten a house without interest or vice versa. So it’s an interest-free loan. An option is basically leveraged without debt. You can option a $100,000 house for $2,000 or $3,000, or like 2%, 3%, 4%. That’s high leverage. That’s high leverage. And people . . . I won’t get it. People always, the other side, there’s enough in it for them. They’re happy enough that they like what they’re getting on their side.
Mike: Yeah. Yeah, it’s interesting because a lot of people have this misconception, I guess, that . . . when I go look at houses, they need the money right now. And if you’re dealing with a landlord, like you said, specifically landlords because it was an investment for them. Or we’ve talked to people that . . . I’ve had some sellers actually seller finance me houses and it was always because they didn’t need the money right away. They had already moved into another home so they didn’t need the money from that sale for the next one. So they were just going to put it in the bank or something. So I think that would you say that, generally, you can get creative with people when you find out that they don’t need that money now?
Jack: Yeah, civilians. I mean, if you deal . . . that’s why they stayed away from commercial properties or even duplexes, triplexes. You have to deal with another investor and they’re, well, say they’re tougher to deal with. They want it all-cash and they will find all-cash. Civilians, as Pete Fortunato might call them, they’re amenable to different things. As long as they’re covered okay, they will get their money over a certain period of time.
And if you say, “Well, if I gave you $100,000, what are you going to do with it? Put it in the bank at .1%?” We handle millions of dollars come and go and a 1031 exchange business, we get less than one-tenth of a percent. It doesn’t even show up on the bank statement.
That’s what they get. A big chunk in the bank. How about if you get it over time and pay on the installments? You find out what’s a buzz word, an important point for them. What’s important for me is they don’t have to write a $100,000 check at the moment.
Mike: Right. And the truth is you probably couldn’t pay $100,000 for the house. I mean, the reason you’re structuring that way is because you can afford to do it over time, whether it’s zero interest or not, there’s kind of an imputed time value of money issue there, right?
Jack: Yeah. And in the meantime, the market here has been up a couple of percent from the ’80s over the long haul. And then, there was the ’07, ’08 thing that went way down. But the prices had been going up a few couple years, which is prior that at 15% a year. Well, that’s unsustainable and it wasn’t realistic and the liar loans. So I went back to, say, a $50,000 house became a $150,000 house, which was an illusion. And then it went back to $75,000 or $80,000, which was more where it normally it should’ve been.
So that using the options from a timing standpoint for people. And when you have the option, it depends on what’s going on with you and you want to do it now or do you want to do it later. And the tenants’ options, they’re not bankable at the moment. And sometimes, we move some along and sometimes we let them sit for seven or eight years. And their house, their price is getting indexed, a couple grand a year. And my spread is widening because I’ve taken over your mortgage that was maybe 10 or 12 years when we started. It starts to buy down and the markets generally have been strong enough that my spread’s been increasing over time. So it’s been a win-win situation with these option strategies.
I have a lot of people I know here that I deal with that are rehab guys. You said you did some of that, right? They get a house, fix it up. I’ve done a lot of those, financed a lot of those with fixer partners and we split some kind of way. But they ended up being at a dealer status or having to pay ordinary income. You buy it this year, you fix it, you sell it, you flip it. So that’s not a long-term capital gain.
So by using . . . putting a tenant in a property, a lease option tenant, when I’ve done my own exchanges, there’s no minimum holding period for the replacement property. The first property in exchange you need to own for a year. The next one you acquire and exchange, you could sell it in two months and you get a long-term capital gain. If it had a tenant, just paint and carpet, it’s inventory and you’re a dealer. But the test from the IRS is it had a tenant.
So I would find . . . a pretty well-screened couple was kind of waiting for a house and said, “Okay. Here’s your house.” And the mortgage lady would give him a little script, pay a few doctor bills, get rid of three or four credit cards, dah, dah, dah, some more payment stubs. Close about four months or five months, take the money, long-term capital gains. I could do another exchange.
Mike: Yeah, that’s awesome.
Jack: So you can change dealer status to investor status by doing that.
Mike: Yeah, okay, okay.
Jack: Okay. Okay. Another thing we do, Mike, which, in a trust, I can have you and Pete and Bob or something as partners with beneficial interest. It’s below the radar. We don’t have to go to the courthouse as tenants in common that you have 20 . . . that we each have 25% and say, “You want out because whatever. You have a golden opportunity somewhere, yes.” I said, “Well, yeah, I’ll buy your share or two of us will buy it.”
And so it’s all done at the beneficial interest level, which you advised the trustee. So in that partnership, and sometimes we have a doctor or somebody that’s an investor, we can sell the depreciation. We can split up the depreciation. You can take that. I’ll take the capital gains. Another one takes the other benefits. You can split up the benefits in various ways inside this partnership. And that’s legal to do that.
So the doctor doesn’t want the ordinary income, but you and I are worker bees. He’s in it so he just gets capital gains. So, okay, he gets 70% of the capital gains. And you and I then decide who gets the interest deed option and who gets the depreciation. That $100,000 house has 3.63% a year a month, that’s $3,600 a year, that’s $300 a month, that’s about the cash flow on that house. So on those 80-something houses, I had all that income as a tax shelter for years and years. So I put a lot of cash flow, which became money to lend, which made more money.
And another option, a big option benefit, one of the best is for your IRA account because I leveraged people. You have $5,000 in whatever. You could make that into $50,000 by using options. Buying an option for a couple hundred bucks, take it to a meeting, you sell that for $4,000 or $5,000, Mike, is that true, sign the contract.
Mike: Yeah, for sure. Oh, easily.
Jack: It happens all the time. We go to a Monday night meeting here. It’s 80 people, 90 people. Wednesday night meeting, this meeting and that meeting. It’s like AA, like you can go to a meeting all the time, seven days a week. So by using that in your IRA account because sitting in the bank, IRA independent custodians or IRA checkbook trusts where you can get your IRA funds in the corner bank and control the checkbooks. So on Saturday afternoon, you can make a deal.
I have five signed checks in my briefcase. I can make a deal tonight or any day. And IRA deals, just by replacing the principal and interest back on the street as it comes in after like another couple of months, it wasn’t [inaudible 00:31:10] this account has $14,000, this one has that, there’s a $40,000 note. So we put together and buy it, now you have another income stream at least coming in, and that will get you 40% just by putting the stuff out back out on the street.
Mike: Yeah, that’s awesome.
Jack: But options are the best strategy for an IRA account that, even now, at a recent meeting, I said, “Anybody in this room, anyone ever tried to give you a house? I mean, not an upside-down house, but a house that had equity. They’re just fed up and they want to leave town?” I know two people in different . . . they knew each other, but their radar was turned in with options. And they said, “Just, please, take this deed. Then they both had equity, $20,000, quite a bit more, but he said, “Oh, we want to give you $2,000.” I said, “No.” The people say, “I don’t need $2,000.” They insisted. Where did the $2,000 come from? Their IRA account. One lady had picked up $20,000. Charles picked up $80,000 worth of equity, long-term on the mortgage because they’re sensitive to option opportunities passing under the radar.
Mike: Yeah. I’ve known some people that do have houses that don’t have a lot of equity. A lot of times with real estate investors, they’re trying to buy the way that I historically have. And what I’ve historically done is said, “Well, I’m not going to waste my time, in hindsight, trying to monetize the low equity deal,” which most of the houses we look at are low equity. A lot of people just don’t have enough equity or enough motivation.
But I’ve known some people that take some of the lower . . . the stuff with lower equity that could be a decent rental and they kind of partner with somebody that’s like a property manager that can . . . they basically say, “Hey, you buy the property, but my IRA is going to buy the option to 50% of the profit when you sell it. But you deal with it, you manage it. I don’t want anything to do with it. My IRA just owns beneficial interest or an option on half the profit.” Whatever comes to, you sell it or 15 years from now, we’re going to sell it.” They buy it for a very low . . . maybe $100 from their retirement account. I’m not an expert here, by the way, anybody here that’s listening.
Jack: Yeah, but it’s high leverage but takes a little bit of money into the game. It’s legal so I withstand and audit everything. We do meet with IRAs or not, that’s an open book. No self-dealing, anything like that. These options, one thing that people use options for is to record it on a property. Say you had your home or some a lot of equity in the house. You say you had a free and $100,000 rental. If you gave me an option to buy it for $50,000, would that look attractive to somebody else that got mad at you and wanted to take that house? Because I can buy it for $50,000 anytime I choose.
So people use options as a defensive maneuver. Who’s to know who amongst friends. If I did that with you, I would send a release of option notarized and witnessed in your drawer in case I was in China or something, somebody wanted to give you twice as much. So people use options as a defensive strategy and you can’t tell.
And there’s another. The IRS, in an option, you need to have consideration, some kind of money dates and you need a specific option exercise price. So you need a specific amount of money and a defined purchase price after two years, three, five, whatever the amount of time is, not just an open-ended thing. If it’s open-ended, it’s not a valid option. You can use a formula and say today’s price plus the seventh district cost of funds or the CPI or some kind of known index.
So after that, it needs that, but there’s one other exception to the option law that you can get an option for a real estate if you manage real estate. So if you manage a person’s property, you can get an option, a legal option, to buy it at a certain point because the IRS considers the management function to be a consideration. So it doesn’t have to be money in that case, but if you’re the property manager. So I know people who manage properties for other people that are not licensed, but they have an option to buy the real estate as a valid option. So that’s one of . . . there are umpteen more ways to kind of exchange properties and sell with an existing option. It can go on and on for . . .
Mike: Oh, I’m sure, I’m sure. So, Jack, for people that are listening today, I know these are some . . . you were talking about some advanced kind of techniques and stuff, some advanced things you’ve done. But for folks that are new or newer that are like, “Yeah, this sounds really interesting to me,” what can they do to learn more? If they were just getting started and wanted to learn a little bit more about the basics, what’s a good way to start to do that?
Jack: Well, I have a website, Mike, So there’s a button about trusts. And we use personal property trust, land trusts, checkbooks. So there are blogs, there are articles, I think, and then at YouTube, maybe 10 little couple three-minute videos. There are little articles. I talked to one guy that said, asked me a question, he said, “No, I’ve seen all your videos, I’ve read all the articles, then there’s a button about options.”
And I have this book and a course. So I have filmed this one-day course that we just did video, a 9:00 to 5:00 course, couple-hundred-page book, CD with 37 forms and with about, 20 sample forms filled it about Joe Taxpayer, Mary Trustee to then to help people do this. My goal is to put it to work than to put it on the shelf. And so people, those courses are on my website, And I’m working on, actually, some note stuff, some note purchase strategy.
So Jack Shea Real Estate has those articles, Q&A, people can write me, call me. I’m open. I don’t mind helping people. I’ve been at this 30-something years and it’s been good to me and so I’m happy to pay it forward.
Mike: Absolutely, absolutely. Well, Jack, thanks for spending some time with us today.
Jack: Well, it’s good, Mike, and nice talking to you always. So anytime, you can rope me in and figure out the technology so we can talk to each other. We’ll do it.
Mike: Yeah, yeah, absolutely. So for those of you that are listening, this is episode number 374 with Jack Shea. Jack’s got just a ton of information and he’s got a ton of knowledge and I’ll write a link down below the video here to his website where he has a lot more resources you can check out. And I know some of these things are complicated.
So, everybody, I appreciate you joining today for episode number 374. We’re going to keep them coming your way with our weekly show. I’d like to ask you, if you haven’t yet, please go to and give us a rating or Stitcher or Google Play, anywhere else where you might listen or watch this podcast at, or I guess even on YouTube, subscribe to us there.
But yeah, anything you can do to kind of show us that you’re listening out there, we appreciate it. And that’s what keeps us going, that’s what’s kept us going for 374 episodes so far, plus having great guests like Jack. So, everybody, I hope you have a great day. Jack, thank you again, my friend.
Jack: Thank you.
Mike: And, everybody, have a great day. We’ll see you on another upcoming episode. Bye-bye.
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