If you have ever felt like your business runs on leads that go nowhere, you are not alone. In this episode, I sit down with Sheldon Wolf, a founder, investor, and operator with over 35 years of experience across real estate, finance, and technology. Sheldon built Intellitary, an AI-powered platform he calls the “Un-Brokerage,” designed to pre-qualify buyers and sellers before they ever reach an agent. We get into why most lead generation is a waste of money, what it really takes to build a business that survives the next market shift, and what he believes the real estate transaction will look like five years from now. If you are ready to rethink how customers find you, this conversation is worth your time.
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Hello and welcome. I’m Adrienne Green, and here we talk about how, as a real estate entrepreneur, you can get out of the grind and start getting the freedom that you really got into real estate for in the first place. And to speak to that, today I have with me Sheldon Wolf. Sheldon, thank you for joining me.
Thanks for having me. It should be a lot of fun.
So Sheldon, my understanding is you’ve spent over thirty-five years as a founder, investor, and operator across real estate, finance, and technology, all things I love. So for our listeners who are just meeting you, what does your world look like today?
Insanity, of course. I would have it no other way. I thrive on chaos. To me, a lot of people, business is business, it’s their job, it’s what they do. To me it’s a sport. You step into the ring each and every day and you slay the dragons. That’s what it comes down to. I’ve been doing it since nineteen eighty nine, and you can be sure I’ve seen enough ups and downs and all arounds and all that crazy stuff, good times, bad times. The one thing I speak to a lot is the fact that I actually tend to thrive when things are crappy. So the worse things get, the better I get. It’s that athlete mentality where you step in the ring and you know you’ve got a tough fight, you’re gonna fight that much harder. And that’s exactly how it works.
What I’m hearing here that I love is an abundance mindset, right? We’re gonna, like you said, slay those dragons. This is gonna be fun because we’ve gotta do it one way or the other. We can either be complaining about it or we can have a positive attitude and be like, these are wonderful problems I get to solve. I love that.
Well, it is a lot of fun to me. I would not see myself doing anything else. Everyone always says, Sheldon, why don’t you just sell off your properties, retire, like what are you doing? How much money do you need? This isn’t a money thing. It doesn’t matter what I’m working at. It’s a play to win thing. It’s beat your own record. It’s not about I have to beat someone else’s record. I don’t need to be bigger than this guy or that guy. I need to do better than what I did last year, or that one year, five years ago, or whatever I built I can do better, or what if I did what I did but I made it do this and this. It’s that kind of mentality. It’s like going into a game where you know you already win.
And I bet every real estate investor listening can relate to that. We all have somebody in our lives who tells us exactly what you just said. Why are you still doing this? Why do you have the hassle? Why are you dealing with these tenants? Why are you dealing with that busted pipe or whatever happens, right? When the truth is, like you said, it’s about being one step better than I was yesterday. So tell me a little bit about your current fun game of Intellitary.
Intellitary’s juicy, and I’ll tell you what makes it really interesting. I’ve worked from the investor point of view. I’m an investor and I’m an entrepreneur, founder, all those fun words. But I built Intellitary backwards. My blueprint starts at the end. This is something that people who are highly successful would understand. But if you’re both the founder and the investor, you pretty much map it out. I’m well beyond the wall. There’s gonna be a wall that’s gonna blow in, and whether it’s in two years, three years, five years, this goes right through the wall. So I’m past that. We start with the profit and all those things that people don’t like to talk about. They like to talk about the revenue but they never like to talk about the profit, because usually there is no profit after the cost of acquisition, all those other fun things. So this works itself backwards, but what it actually is,
Okay. Yes.
It’s nineteen eighty nine, nineteen ninety-two, nineteen ninety-five, all those illustrious years of old school hand-to-hand combat real estate transactions, and I’ve put together thousands, very few people put thousands of transactions together. I put thousands of transactions together. This is everything I’ve done, my entire legacy, turned into an AI orchestration layer that follows the same monetization system I’ve used for thousands of transactions over three decades. The easiest way to explain what Intellitary is, it’s a customer orchestration layer that’s very customer centric. What that means is, where the world is built of brokerages, and I’m assuming you have quite a few real estate listeners and maybe some brokerage listeners and a lot of investors, typically the brokerage recruits realtors.
The more realtors,
it follows a formula. If you’re a brokerage and you have 10,000 realtors, you factor in the math and say, the average realtors all put together equal this many transactions per year, which equals that. So they’re on this big march to recruit as many agents as possible, on an all-time basis. That is their agenda. And now you see this kind of march where they’re buying old legacy brokerages. You see the sale of RE/MAX, you see the sale of Fathom and all these other companies being
Yeah.
bought by bigger companies with more firepower. And then what you see is me, I call it an Un-Brokerage. I’m building something the opposite way. I’m not interested in having the realtors. The realtors are there, we’re going to cooperate with them. We have programs that we’re building out for the brokerages, but we’re interested in orchestrating and originating customers, because our view of the future of real estate is whoever controls the customer controls the real estate world. If you’re a brokerage or a realtor and you don’t have customers, well, I’m sure anyone can tell me what that looks like. That’s where the revenue comes from. That’s where the profit and all the wheels start turning, is when you have the customers. No customer, no business. Very simple. So we built it backwards. The easiest way to explain what I built is Best Western Hotels, which everybody knows, but what they are, they don’t always own the hotel. They’re an orchestration layer and their only purpose is to take the customer we speak about and drop them off at the check-in desk at a hotel in any city in almost any part of the United States and Canada. That is their goal and that is their purpose, and they’ve done their job when they’ve got their traveler at the check-in desk. We do the same thing with real estate. We take a pre-screened, pre-qualified customer who wants to buy, sell, get a mortgage, all those fun things on the monetization path I’ve invented, and deliver them into your front seat or to the front door of the house they want to see, or to the brokerage where they’re gonna assign a transaction. I’ve essentially built something where, if you’re a brokerage, you’re just gonna get an extra fifty thousand transactions, and then the next step is, if you’re going to originate fifty thousand transactions this year and hand them to this brokerage so their realtors can harvest the results of that, well, the fact of the matter is that fifty thousand transactions are fifty thousand transactions not going to their competition. And that’s essentially what I’ve built.
I appreciate a lot of what you shared there. As a licensed real estate agent who was active for a period of years, I can attest what you’re saying about those brokerages is exactly how they do it. They focus on, let’s recruit agents, let’s recruit agents, and then the agents are gonna go hunt, because it doesn’t really cost them much to have those agents, right? But the brokerages don’t really worry about customer acquisition. They do what they can, but they figure it’s the agents’ jobs mostly. So of course
Yeah, exactly.
the next logical question to me is, how is Intellitary getting all of these high-quality clients?
Well, the fact of the matter is, we use AI technology that, let me put it this way, was personally designed. I’ve been very, very involved right from square one. I developed it, designed it around my own success. So when I say this thing goes back to my roots, there’s a reason why I’ve put together thousands of transactions. There’s a reason why the average realtor literally only does two to three transactions per year. That’s the average. That means nothing when you think about it, because there are realtors out there who do six deals a month, five deals a month, even some twelve, ten, all over the map. But then there’s a lot of realtors who just do very little. They coast. And it’s not that they don’t know the industry, obviously they’re in the industry. Their biggest problem is customer acquisition. So if you’re a brokerage on that side of it, you have a whole bunch of agents in your office that are not really providing revenue. They’re there, and maybe you’re getting a hundred dollars a month as a monthly fee, and then maybe when they sell something, if they sell something, you get a percentage of their commission. But that’s not enough, because when I read financials, and trust me when I tell you I read everybody’s financials, if they’re out there and they’re publicly traded, I’ve read your financials and I know your flaws. There’s some companies out there where the realtor gets a deal and the brokerage only gets two hundred and seventy-five dollars off the commission and literally a hundred dollars a month. There’s some that take zero transaction fees per month. So when you read
their financials, it’s nothing but red ink all the way down, and they’re bragging, look at our revenue. But look at that column next to it, which has got red ink on it. Your system’s not working. But we have 25,000 agents. That means nothing. I’d rather have a hundred agents and be a brokerage making millions of dollars than a brokerage losing hundreds of millions of dollars every quarter with 25,000 agents. To me, it’s not about how many agents, it’s about the transactions. Transactions are where the revenue hits the door of your office, and that’s what I’ve built. You worry about recruiting, do what you guys do best. I’ll worry about how the customers are going to be delivered to you. So I built a system, a delivery system, and it’s actually ironic because it operates and functions kind of the same way Uber does. So a customer, Joe Smith, who is pre-approved, who’s already sold his home, wants to view 123 Cherry Tree Lane. It literally pops up and gets dispatched the same way. He wants to see it at three o’clock. This realtor’s available, that realtor is available, and whoever picks it is meeting this customer, and they already know who, what, when, where, why, and how. They know everything they need to know, and the meeting’s booked. The second thing it does is it transfers the customer
in real time. It’s all fully functional. You go to the website and you’re gonna have a conversation with Chloe AI. Chloe AI, much better looking than me, I will say, but you’re gonna have a conversation as fluid as the conversation you and I are having right here, right now, with somebody who looks as real as I do, but better. She’s gonna get you to sign up, which is literally give me your name, number, and email. And as soon as you do, she’s gonna then call you and say, hey, it’s me, Chloe, I was just chatting with you on Intellitary. But now that she’s got you on your phone, she’s able to sign documents with you, hot transfer your call directly to someone in that area right now who can set up that showing for you. It’s all fluid, it doesn’t break. It literally runs down a
perfect real estate track right to the brokerage door. That’s essentially what it’s doing. It’s designed to handle customers the same way this guy would. So as good a software guy as I am, as good an AI tech as I am, and as well as I completely understand the integrations, I’m also the guy who’s done thousands of transactions. I see a lot of companies that are built by a great software guy, but he doesn’t know the industry. So when you see, well, why did it fail? They got to a billion dollars and then they crashed. Nobody understood the industry. So I bring both, I bring the best of both worlds, the tech and the industry, to the table.
So what I’m hearing about Intellitary is it’s a new take on a model that’s been around for a while in terms of helping with that lead generation, right? Helping bring that ready, willing, and able buyer or client to an operator’s doorstep. We see that in the real estate agent space. We also see a lot of companies trying to do it in the real estate investing space, because that lead generation is tough. So we love when there’s a good company working to fill that gap. Now here’s my question, Sheldon, for our listeners who are these real estate entrepreneurs. Intellitary, you know, you’re not the only one out there helping do that lead generation. What are the top questions an entrepreneur or operator should look at when they’re vetting a company like Intellitary, somebody who promises to bring them a beautiful client right to their doorstep?
Okay, so here’s the difference, because I’ve been in this game a long time, and I’ve seen lead gen come up, I’ve seen how they get their leads, how they process their leads, who gets their leads, how many people get the same lead. I’ve seen it all. It’s the oldest rodeo in town. So I decided I’m not interested in producing leads. I want to produce actual bona fide customers, where instead of just getting a name like most realtors, or even in the investment side of things, you’re getting a guy’s name, his phone number, and his email. And whether he applied right here, right now, three hours ago, or three days ago, the bottom line is, what you’re actually buying right out of the top is a 50-50, because 50% of all leads, you’ll never actually
get in touch with the customer. I don’t want to produce that. I want to produce something transaction-ready. Something where a clone of me, who would handle a lead as good as I would, is actually discussing and getting the commitment, getting the loyalty, finding out all those questions realtors are too embarrassed to ask, like, hey, have you been pre-approved? Tell me a bit about your income, all that stuff. And
all those fun things. I ask, how soon are you looking?
Very simple question, but guess what? It’s not what you think. It’s how motivated are you, and it’s how you answer the question. I’ve built in what I call heat scoring. So every answer is a score in a matrix I’ve built, and that’s going to determine how serious this customer is. I do not want any of my agents running around with a guy who’s bankrupt who can’t buy but says he wants to buy, or just wants to look at properties. We’ve pre-screened everything, it’s vetted.
A guy who says, no, I’m actually very serious, I do want to see 123 Cherry Tree Lane, it’s the perfect house for me, have one of your guys meet me there, and then it gets dispatched, very simple. Or, yes, I do want to sell my property, I’m looking for this, here’s my house, here’s all the details on my house, and then that gets sent out to three of our agents to do a proposal on it,
an evaluation, and what the best commissions are that you’re gonna offer this customer. So it’s all real customers, we’re not interested in leads. I’ve been in that game before, a long time, and you’re buying mostly garbage. The true statistics, and you can ask any realtor out there, they’ll tell you the same thing. Number one, you’re only going to talk to 50%, if that, of the people you’ve actually paid to speak with. From there, you monetize at about two to three percent. So what does that mean? You have to go through a hundred leads to really get a couple that are even potentially where you’re gonna see some revenue. Now, does it all make sense in the end? It makes sense, because if you do a deal and it’s a big enough deal, your commission’s gonna be worth it and it all makes sense, but it’s a hell of a lot of work just to get one customer to transact. Where we’ve eliminated all the fluff and garbage, this is as if I took the call myself. In fact, better. And I’ll tell you why it’s better: Chloe on Intellitary can handle 20,000 phone calls at once. 20,000 unique calls. Me at my best, no matter how good I am, I can take one call. I’m doing your podcast, I’m not on 20 other podcasts, I’m not on 20,000 other podcasts. I’m here right now. That’s my limit. Chloe can talk to 20,000. So that’s what she does.
And how can a business operator who’s vetting companies like yours differentiate between that level of closure rate you’re offering versus other competitors or other options they might have?
Well, there’s no, I look at everything I build and I don’t believe there’s that kind of competition. And I’m the guy that, when I step into the ring, if somebody says, hey, I can build that out, I can do this, I’ve seen a lot of software guys come and go if they don’t understand the industry. If you’re not a guy who understands what it’s like to put thousands of transactions together, I mean, I built a funnel back in the day, I never actually left my desk. So I may have sold more real estate than anyone else, but I never actually left my desk. I built thousands of properties, and almost every property I sold wasn’t even built at the time. These were invisible homes, all sold off blueprint. So if you can build that kind of machine, where you’re selling real estate without showing houses, without going through property, without going through all these different processes, but it was a lean machine where a customer would be at my desk, they’d already be pre-approved, I’d know everything about them, and my entire day was spent writing transactions. That’s what I’ve reinvented with
Intellitary. And really, I don’t believe there’s anything. There are a lot of lead companies out there, you can buy real estate leads all over the place. But the fact is, I talk to realtors every single day, I talk to brokerages every day, and they’ll all tell you the same thing: yeah, I’ve spent six thousand dollars on these, I got zero in return. If you don’t have that rate of return, then it’s a complete waste. Advertising, same thing. You could spend five, six thousand dollars on advertising and get nothing but garbage calls and nothing that turns into anything. This is taking all the fluff out of the game, so you’re not buying a whole bunch of names and phone numbers, so to speak.
Well, and one thing you mentioned in your answer there, Sheldon, was the idea of using a system, right? And that you built a system you’re replicating here with Intellitary. So let’s talk about systems, and part of that is the delegation, right? When somebody’s working with a company like Intellitary, they’re really handing off some of the work they would do to a technology, to another customer. Now, you’ve spent your career thinking about systems, software, so that we are not
manually doing all the work ourselves. Like you said, you can only take one call. Usually that starts with mindset. What would you recommend to listeners who are struggling with the idea of going from solopreneur, DIY, I do it all, to let’s leverage systems, let’s leverage technology? What would you say needs to happen with their mindset? What’s your wisdom?
Well, the thing about it is scaling and growth is the most important thing. If you don’t harness that, you’re going to be at a standstill. It’s so important that you have that vision. One of the things I said a little while back is I build things backwards. I start at the goal, and I work it backwards, and I’ve factored in all the good times, bad times, and all the fun things that are gonna come along the way, the triumphs and tribulations. I’ve factored in the fact that there’s going to potentially be a wall. There’s a company out there, a massive company, billion dollar company, but they didn’t
factor in the wall, and they’re a very volatile company because they’re affected by things like interest rates. Something as simple as interest rates freezes the market. Meanwhile these guys acquisitioned a whole bunch of properties, but the properties were acquisitioned six months ago, five months ago, seven months ago, and now they all come to fruition today. How you bought the houses then
is not gonna stand well today. So things like that have to be taken into consideration. Things like the volatility, things like walls coming up, whatever you’re doing has to be designed to be beyond the wall. So, you know what I always say, in a cyclone, even a turkey will fly. When times are good, everybody’s making money, everyone’s driving around in their nice BMW and Mercedes. When times go bad,
my apologies. When times are not so good, all of a sudden that smile comes off the face real quick, and that’s where you have to be able to fight and understand that there’s ways around things. So whenever you’re building a system, embrace technology. I hear so many agents say, this AI thing, instead of celebrating and saying, how do we use it to our advantage,
Mm-hmm.
they’re complaining about it. It’s taking people’s jobs, I hate this AI. No, you hate it because you don’t want to spend any time engaging it or learning it or understanding it. Instead, you need to embrace it. If you do not embrace technology, you’re gonna get run over by technology, because if you’re not using it, your competition is. So I speak to brokerages every day and they’re saying, well, we just upgraded our system five years ago. Well, five years ago in technology land, your five year old phone probably doesn’t even work anymore. It’s on 2G or 3G, and everything becomes obsolete. That’s why I built Intellitary. It’s meant to go and punch
through that invisible wall that comes our way, whether it be a dot-com bubble, an AI bubble, or this bubble or that, there’s always another bubble. Anyone who doesn’t believe that hasn’t been around as long as I have. I’ve been through many bubbles. It’s designed to do that. If you’re trying to solve today’s problem, that’s a problem, because today’s problem is already solved by 5 p.m. By tomorrow it’s been copied, and by next week it’s obsolete. So anybody who’s saying, but I just changed my software five years ago, three years ago, we just bought today’s today, tomorrow’s tomorrow, and we need to focus on tomorrow, next year, five years. Because five years will come, and it comes sooner than you expect. You don’t want to be caught empty with no good new technology. Good technology today, doing what I did in 1989, wouldn’t work today. Doing what I did in 1995, that wouldn’t work today. Doing what I did in 2000 wouldn’t work today. As good as I am at meeting a customer hand to hand, putting a deal together, that part works. But
how I’m getting that customer, how I’m acquisitioning the customer, how I handle the customer, how the entire monetization system works, that you have to stay in touch with, because that will change.
And you’ve mentioned on several of your answers here about a wall. Can you dive into that? What is the wall for the real estate industry that you’re seeing in the near term?
Let me put my investor hat back on here. The fact of the matter is, everybody, unless you’ve been hiding under a rock somewhere, can see what I see, and I see affordability being a problem. I bought my first property when I was in my very early twenties, maybe twenty, twenty-one. It wasn’t a problem because properties were a hundred thousand dollars back then, where that same starter-like home today is pretty much starting at half a million dollars. A million dollars doesn’t even take you that far. It gets you a decent house, a nice house, but it doesn’t get you that big sprawling million dollar mansion of yesteryear. So the fact of the matter is, people these days aren’t buying their homes until they’re in their 30s. The next generation is gonna wish they could buy their home in their 30s, but 30 becomes 40. It’s this evolution of affordability, and I see it becoming something unless somebody is smart enough to figure out how to make
a property affordable. The house doesn’t need to be built cheaper. There just needs to be better ways to buy real estate. That’s always been my strong point. So when the rates went up, I did buy downs. Everyone else had an eight percent interest rate, I had a five percent interest rate. Whatever we were able to legally push and buy down and promote, that’s what we did. We found ways to work with down payments. We found ways to stretch it out. I had the luxury of spending a lot of time in the building and development industry, so I was able to
stall out payments while the home was under construction. I was able to do investor deals so by the time the guy’s house was built, he’s already making forty, fifty thousand dollars and he hadn’t even moved in yet. There’s always a strategy to get past the wall. You just have to know what this wall coming up is. I think real estate,
most people naturally think, well, what about these mini homes, we’ll just build smaller homes, cheaper homes. That’s partially right, but that’s not gonna solve it, because someone still wants to buy a home. People still want that so-called American dream. So I think it’s a matter of creative programs. It’s not really the hardware, the hardware’s your house, it’s the software. It’s how you’re going to make that transaction happen. That’s always been my strategy, because at the end of the day, drywall is drywall, lumber is lumber, roofing is roofing, concrete’s concrete. All those things have elevated, and all those things go up with the cost of living. So how do you fix that? The cost of labor goes up because the cost of living goes up and people need to pay more. So you need to deal with the software end of it. If the program is the software,
the hardware is the home, that’s what you need to deal with. It’s always on the other side, but people don’t automatically think that. They think, well, there’s gotta be a way to build the house cheaper. You don’t need the house to be cheaper, you just need to make it so that this guy can afford to pay. Usually it’s a matter of, he’s gotta pay to live somewhere, he’s gonna pay rent. How do you make it so the mortgage payment smells more like that? Because people at the end of the day don’t really care how much they paid for the house. They care, can I afford to live in this house? That’s really the truth of it. And that goes to all the investors out there.
That’s a lot of good points there. Now with AI and everything that’s happening on the forefront, I’m curious what you envision the day to day role of a real estate agent looking like, let’s say five years from now.
The AI will be completely, so to really answer your question, I’m gonna answer it backwards. It’s not about the agent. The agent will have AI, or they’ll simply not be in the business, or they’ll be one of those agents we talk about that does maybe a deal a year because their friend just bought a house from them, or a friend of a friend just bought a house from them. So let’s talk about the customer, which is the reason I built Intellitary.
It’s the customer that behaves differently today. The realtor doesn’t behave differently. Their goal is to find a customer, show a home, sell a home, or list their home and sell their home and then sell another home. That part’s exactly the same. How you’re communicating and where you’re getting the customer is a little different. But at the end of the day, we have a smarter customer. The customer is the same customer, but they’re smarter only because the technology allows them
to have access to better information faster. So I’m a home buyer and I’ve got a phone in my hand now which has AI on it. So I need the realtor less and less because I could already find out where the schools are by asking a simple question. I can already figure out the crime rate. I can already tell that I can’t afford to live in that area because it already knows
my budget, it already knows my debt ratio, it knows all that stuff. It already told me how much I can afford, how much I’m gonna qualify for with my income and my debts. So the customer who knew nothing about real estate two years ago
all of a sudden knows everything, and they’re a genius. Whether the information is 100% accurate or correct is a whole different story. There’s a lot of misled customers out there, but they transact differently. Where are we in five years from now? You’re gonna have a customer that will be able to do a beginning to end transaction. To me, everything is just data and field mapping. So you’ll have a customer that will be able to press a button and make an offer, all that fun stuff. Do I think there’s a need for realtors and brokerages? Absolutely. I’m a preservationist. As great as I love my technology, I’m using the technology to preserve the industry. Do I think a customer will be able to just write an offer, press buttons, add in whatever conditions are recommended for their situation? Yeah, I do.
Do I think that will be the same for the law industry? Yeah. But do I think people should be their own lawyers? Not necessarily, depending on your situation. But there’s a lot of liability, and real estate is one of the most expensive investments or assets you’re going to obtain during your lifetime, whether you have one property or an armada of a hundred properties, it’s still the biggest,
most expensive investment you’re going to jump into. Do I think that having a human is always good to have? Yeah. I play with AI I don’t even know how many hours a day, because I’m always developing something. But it’s not a hundred percent accurate. Do I think there’s gonna be flaws in five years from now? Yeah, of course. There’s gonna be flaws in ten years from now. There’s gonna be flaws always in everything. Everything is a double-edged sword when you’re playing with technology. Okay, I got it to do this, but now it’s struggling with that. It’s doing great with that,
but that’s right. So where do I think the realtor is gonna be in five years? It’s more like, where’s the customer gonna be in five years? How do I get B to connect with A? That’s how I look at it. How do I get this data over to this guy so he can do his job? Maybe his job is less and less. Maybe he’s just simply receiving an offer from this customer, reviewing it, and putting together conveyancing, all those fun things.
So I see it just integrated differently. But I think it’s always gonna be the same. At the end of the day, it’s a person wanting a roof over their head. So as complex as it gets, I like to bring things back down to simple.
And I think that’s a great place for us to wrap up, Sheldon, where we have this wisdom from you about technology and the human component and how they’re going to continue to work together going forward. Sheldon, if somebody would like to connect with you or learn more about Intellitary, what is the best place for them to do so?
The best way to hit me up is to email me at Sheldon, S-H-E-L-D-O-N, at Intellitary dot com. Intellitary is I-N-T-E-L-L-I-T-A-R-Y dot com. You can also find me on LinkedIn, feel free to add me, feel free to connect. Very easy to communicate with, you can ask me absolutely anything. You’re also welcome to go to my personal website, which is sheldonwolf.com.
Perfect. Well thank you so much, Sheldon. And for our listeners, thank you for joining me. Join me again next week to hear another great take on the real estate industry today.