Revolutionizing Real Estate

Mike Pinkus: Over the last 10 years at ConnectCPA, we've had the privilege of witnessing the incredible journeys of over a thousand businesses. We've been there for the thrilling highs and daunting lows of entrepreneurship. We've celebrated wild successes and monumental exits, and we've also stood by businesses as they've navigated the stormy seas facing Roblox, and challenges that every entrepreneur encounters in their day-to-day grind. Join us as we dive deep into the stories of these resilient individuals who dared to dream, who persevered, and who were a testament to the power of entrepreneurship. This is their journey, their lessons, and their triumphs. Welcome to GrowthTales. I'm your host, Mike Pinkus, co-founder of ConnectCPA.

Mike Pinkus: Today's guest is Reuven Gorsht. The CEO of Deeded helps solve what used to be one of the most stressful experiences for individuals, and that is closing a real estate transaction. Reuven and his team have built a special combination of lawyers, technology, and a process to simplify and enhance the closing experience over both purchasing and selling real estate. As a multi-time founder, Reuven has so much knowledge about scaling a business, and we discussed everything from the interest rate environment, how to leverage technology to solve data intake, and how to build a great team and culture. I really enjoyed my conversation with Reuven, and I hope you really enjoy this episode. Hey, Reuven, thanks so much for joining me today on GrowthTales.

Reuven Gorsht: Hey, Mike, great to be here. Thanks for having me.

Mike Pinkus: I really appreciate you joining it. And before we dive in, I'm gonna first explain, uh, uh, the black eye really quickly because anybody watching this in video format is gonna be like, why does Mike have a black eye? I got smacked in the eye by, uh, my 3-year-old daughter. That's the extent of it, while we were in a swimming pool. But yeah, that's the story. But I could have given you something about Fight Club, but I figured I'd be honest and tell you what happened.

Reuven Gorsht: Absolutely. Well, hope you feel better, and that's a good story to stick to.

Mike Pinkus: Yeah, definitely feeling better now. So, Reuven, I want to first talk about just your origin story of Deeded, 'cause I feel like you've built a really incredible company. The real estate space is an exciting space and something that people are following right now with fluctuations in interest rates and all the things changing the world today. So why don't I just start off by asking you, where did the idea for Deeded come from?

Reuven Gorsht: Absolutely, Mike. So for me, it really came from my personal experience. A few years back I was buying a house. My wife and I were super excited about closing day. I remember us sitting in the car in the driveway of our new home, and we're just waiting for a lawyer to give us a call and say, you know, everything went through, you can come get the keys. We had movers coming in that weekend. We had even friends and family that were gonna drop by. My phone rang before we actually expected the call. I look at the call display, it's my lawyer. I looked at my wife like, yeah, this is the moment we're excited about. But, as you would imagine, it didn't turn out to be that moment that we expected.

Reuven Gorsht: I was actually missing a document and was told, well, we're out of luck and we won't be able to close today. I learned a mistake of not to close on a Friday, and I keep repeating that to anyone that will listen. So basically, we ended up homeless for the weekend and took our family through the Holiday Inn and had to untangle this whole mess that was caused by this delayed closing. Including, we had bridge loans, we had movers that didn't have anywhere to put our stuff, and they offered to kindly leave it on the lawn or hold it ransom for a few days. I started to take a look at the whole discipline of how real estate and mortgage transactions are closed.

Reuven Gorsht: I started talking to a whole bunch of folks, realized that I wasn't the only one with the problem. Realized that it happens quite often. There's not a lot of transparency. When I say transparency, it's just understanding what's going on and how you're kept in the loop from a communication perspective. Especially if you think about real estate, it's a high-value, probably the largest transaction you'll ever do financially for most people. And with that high value, it's high stakes, high stress. So everybody's on pins and needles, always looking forward to the moment that their home will close or their sale will close. But the journey to get there, unfortunately, was pretty painful from what I saw. And that's where the whole idea for really modernizing this whole process came to mind. I got together with a couple folks from the industry and brainstormed. And here we are.

Mike Pinkus: Yeah. I wanna talk about how Deeded is different, Reuven, because as you said, you wanted to change or revolutionize an industry that's been stuck in its ways for a long time. And we all know what that real estate closing process is like. Anyone who's been around the block knows the traditional way of doing real estate closing—you drive to your lawyer's office, you get presented with a bunch of papers that you don't understand, with title transfers and all this sort of stuff. But some of the best business models are the ones that give back time to people. And I feel like Deeded has done that in a big way. So I wanted to ask you, what is different about the business model or the offering that you give to your customers versus the old way of doing things?

Reuven Gorsht: Yeah, so I would break it down to what we just talked about—transparency or really understanding everything that's going on in real time and always feeling like you're in control. That really stems from a concept like, for example, Amazon, or 25 years ago, Domino's invented the pizza tracker. I know it's hard to believe it's been that long ago, but nowadays, Mike, I notice almost every business follows the same blueprint. Your consumer is expecting to be well-informed. They always want to know what's going on, they want to know that there's someone there to answer their questions, and they want that assurance that their transaction will close—and will close smoothly. So that's really the first piece.

At Deeded, we have a technology that allows any of our home buyers or sellers—or if you're refinancing your mortgage—you can log in and get notified of every major milestone that your deal hits. Right down to when you're signing your documents to, "Hey, don't worry, Mike, we've received all the information from the bank. You can sleep easy and everything's on track."

Reuven Gorsht: The second part of it is really that convenience of being able to do the transaction virtually. As you mentioned, it used to be that you hire a real estate lawyer, but then you have to take time off work, drive to that lawyer's office, sign your documents, and walk away with a stack this thick of documents. But there wasn't a lot of convenience to it. Lawyers typically work nine to five, so here we are taking some time off work, driving downtown, paying $35 for parking. And nowadays, you can do it virtually.

That's convenient on its own, but it's also a change of environment. We find people sitting in their living room after they put their kids to bed are much more at ease. The stress eases from having to be there for a 20- or 30-minute appointment or sitting in a waiting room and not being able to ask questions. Again, high-stakes process, high stress. People have a lot of questions, especially if they're first-time buyers or maybe they haven't bought or sold a property in a while.

We find there's the convenience, there's the security, and then there's just being in a different type of environment to be able to close your transaction at ease. And essentially, you could do it from anywhere. You could do it from your office at your lunch hour. We've had folks do it from their car, sign their documents. So just having that aspect.

Everything we do is really tailored around what today's modern consumer wants. And it really indicates that it's seamlessness, it's that sense of control—I know what's going on, I'm in control, I'm in the loop. And all of that forms a very, very unique experience. There's really nothing else like it in terms of how the industry has traditionally operated.

Mike Pinkus: And I think you've really solved, as you alluded to, a really complex problem. But it is a complex problem. So I want to ask, Reuven, as the entrepreneur, as CEO of a company, you've got a lot of moving parts to make that value work for the customer. Meaning, it sounds like lawyers, technology, and other team members or people that are working on more administrative items—you have to get all of them working in unison and then make it into a business model where you're allocating, I guess, components of time and energy from a business model perspective to have each closing be profitable.

How did you think about structuring this as an entrepreneur? 'Cause it sounds like an amazing concept, the problem that you're solving, but now the execution of that problem sounds very complicated. You have really high-level professionals and lawyers, you've got technologists, you've got other team members that are working on those other aspects. How did you think about putting all this together, and how do you deal with that now? I know it's a loaded question, but I just wanted to hear your thoughts on it.

Reuven Gorsht: It's challenging, nonetheless. But the way we look at everything, Mike, is through the lens of the customer ultimately. And the customer here could be the end consumer—someone who's buying or selling a home or refinancing their mortgage. It could be one of our partners—we work through real estate agents, mortgage brokers, lenders—or it could be one of our team members and lawyers, etc.

So we've essentially taken an approach to personify and determine every stakeholder's needs. And there are a lot of stakeholders. It was a lengthy process, and it's always ongoing. But by understanding what every party needs and what's kind of the happy path—what's the journey that a lawyer might need for their regulation and assurance and to deliver the best quality of service, what does a consumer want—we talked about transparency and convenience and so on—everything we do really aligns to those paths.

In terms of what's the right thing to do for every persona that we have that's leveraging or using our platform, we go piece by piece. And then, you know, make some mistakes, figure things out, iron them out. And ultimately, it's all about aligning around our vision.

Our vision is really to make that closing piece of the real estate transaction really simple and streamlined and essentially effortless as well. And I think when you have the entire team—that includes your internal and external stakeholders—when everybody's aligned around that same vision, everybody sees the same thing, and everybody sort of aligns to what their part is or what their piece is in that process.

Mike Pinkus: Yeah, and I like how you said that—you have to cater this to all the different stakeholders, both from a customer perspective but also an internal perspective, in order to make it all work. I want to know, how important are partnerships in the business that you're building, Reuven? Meaning, in the conduits of the real estate industry, you've got your realtors, you've got lenders and mortgage brokers. It seems like you need relationships with everyone in order to make the ecosystem work well. How important are those partnerships to Deeded?

Reuven Gorsht: I'd say they're critical, but it's also with the lens of having the right partnerships. So, the reason real estate is so archaic is because it's a highly, highly fragmented industry. It's a blessing and a curse, right? If you think about it, there are as many experiences out there for home buyers as there are realtors, mortgage agents, lenders, lawyers. So your path can go in so many different ways.

Ultimately, as we know, the holy grail for any business is delivering a great consumer experience that's differentiated. Everyone's looking at the Amazons and the Ubers as a model. So ultimately for us, partnerships are critical, but the big realization is also that the right partnerships are even more critical. Which means we're not for everyone. We're not out there for the masses to scream from the top of the mountain and say things should be different.

But if you do believe that consumer experience matters—whether you're a real estate agent or a lender or a lawyer—and you buy into the idea that things should be simplified in the 21st century and beyond, then we're the right fit. And we want to nurture that partnership. Again, it goes back to the basics of: Mike, you as a partner, per se, what are your needs? How do we add value? And that's how we look at our entire business. It's like, what does the party need from a partnership perspective, and how do we add value to you and your business, etc.

Mike Pinkus: Yeah, and I think that's a really great way of looking at it. I'm also curious about when you conduct your planning as an owner in a business, and you're looking at the forecast and figuring out what is this gonna look like for the year. I don't have an amazing pulse on the macro environment in real estate, but you probably have a better pulse on it, Reuven. So I'd love to know your thoughts on the interest rate environment. Are you seeing an uptick or downtick in closings in general? What are you seeing in real estate right now, and how does that impact you when you conduct your planning for having capacity to handle the volume of closings that might come your way?

Reuven Gorsht: Yeah, so I mean, it's a loaded question, Mike, 'cause the real estate market is a huge topic. And interest rates are a huge topic, I think, for every Canadian—whether you're a homeowner or you aspire to be a homeowner.

The way I would sum it up is, obviously, we've seen things go to an insane level during COVID, right? People were buying homes and cottages and investment properties as if there was no tomorrow. And I remember stories of properties appreciating literally like 10 or 15% overnight. Somebody would buy a place, sign on the dotted line, and the next day their place is worth a hundred grand more. So we've gone from breaking records in 2021 and part of 2022, to breaking other records now in 2023 and 2024—where we all know the interest rates went up.

Reuven Gorsht: The interest rates drive a lot because ultimately everything comes down to a monthly payment. If your monthly payment was $2,000 a month when you bought your place, and all of a sudden now you're renewing your mortgage and your payment is $4,000 a month, you're going to have to come up with $2,000 after tax to cover that. And as we all know, the cost of living has increased significantly as well—when we go to the grocery store, when we pay our home insurance, and all that stuff.

So, needless to say, it's created a tough situation. I think a lot of Canadians are in a tough spot right now. And if they're not, there's about $900 billion—that's billion with a "B"—coming up for renewal over the next 12 to 24 months. And we know what happens there. People got very attractive rates a couple of years ago, and now their mortgage is going to be renewing, their payments are going to go up.

There's already unprecedented levels of inventory in Toronto and Vancouver. Real estate’s had a great ride for 20 years, and we’re used to—at least in my generation—seeing that hockey stick appreciation and FOMO from getting into the market.

Reuven Gorsht: Personally, I think we're in for some adjustment until the interest rate environment settles. And when I say settles, I don't think we're expecting interest rates to go back to the level of 2021 when it was almost free money from an interest perspective. But nonetheless, perhaps it’s a welcome change. Because with that 20 years of straight appreciation, a lot of folks have been priced out of the market.

I don't think "affordability" is even a word anymore. I think it's extreme unaffordability. Even people earning six-figure incomes can't afford to buy even a starter condo in cities like Toronto and Vancouver.

Mike Pinkus: Yeah.

Reuven Gorsht: So we'll see what happens. I mean, from our perspective, we’re in a transaction business. So people are always buying, selling, refinancing their mortgage, renewing their mortgage, and things like that. We're seeing an even bigger opportunity.

But I think, for a lot of folks who might be watching or listening, many are scratching their heads and thinking about the next move—especially if you're a homeowner or perhaps you've got a good portion of your assets invested in real estate.

Mike Pinkus: Yeah. And it's something I think is on the minds of many Canadians. I know it's obviously a political topic as well. And when we talk about elections and the things that are going to be hot topics, it's the affordability out on the west coast in Vancouver and obviously in Toronto. The major cities are becoming so expensive to live in, like you said—not just from a real estate perspective but in general.

As these things unwind and all these shifts happen in the market, what would you say are some of the biggest challenges you face just running a business? Because Reuven, it sounds like there’s at least some unpredictability or uncontrollables related to how many closings might transpire in a year. What are some of the biggest challenges you face in running?

Reuven Gorsht: It's more so, I believe, adjusting to different market conditions. And like you mentioned, forecasting—so forecasting in a market that’s typically predictable. And I say that because real estate is a very seasonal business. Typically, we’ll see a nice uptick through the spring and summer, and then it goes quiet again. I think if you map out those transactional patterns for the last 20–25 years, they’ve been fairly typical.

But for the last three to four years, they’ve been very atypical. Either there’s been extreme demand, or right now we’re seeing the opposite—tons of properties sitting with “For Sale” signs. I even drove through the countryside this weekend, and every road or intersection had five or six signs.

Mike Pinkus: Times for sale, yeah.

Reuven Gorsht: Right—“For Sale” signs. So it tells you things are not moving, or at least not moving as quickly as they can. I don’t know that prices have adjusted to market reality, which might be why properties are sitting.

Ultimately, when we look at our business, we’ve gotten used to that atypical nature. One day could be incredible—we might see a dramatic number of transactions come in. The next day could be slower. Sometimes it's even driven by simple things, like it was a beautiful weekend, so a lot of people went out to view homes and bought something—so we get really busy on Monday. It’s very hard to predict.

But we’re using that as an opportunity to learn and continue to build. Because we know that, at the end of the day, real estate in Canada is still going to be very prevalent. Every Canadian dreams of homeownership. So it’s going to happen one way or another.

The government is also investing billions of dollars to make homes more affordable, and is exploring different options like multiplexes to help with housing. So we remain very optimistic that in the long term—and this is a long-tail play—the market will fare better, transaction volumes will grow, and we’ll see some kind of return to normalization in terms of seasonality and forecasting.

Mike Pinkus: I always wonder—and I want to ask you this—is it possible… we know demographically you’ve got millennials, Gen X, boomers. There's no secret—boomers are a massive part of the population just from a numbers perspective. People are living way longer than they used to, but there's no doubt there's a trend of downsizing out of bigger homes when people become empty nesters, or moving into condos.

And there's just a lot of real estate-type transactions that will be happening—or will continue to happen—with boomers. I feel like we’re not quite at the peak of that yet. What are your thoughts on that? Like, I feel like that’s on the horizon—that there could be a major upswing just in volume of transactions. Have you guys ever discussed that? Or do you look at the demographics and say, "We know that’s in the long tail, but year to year we’re not really focused on these big macro events like massive upswings in volume that could happen in the next five years or so?"

Reuven Gorsht: Well, I mean, some of those things take years to manifest, right? Because I think what we saw during COVID was a lot of boomers selling and maybe moving out of town, maybe buying that dream cottage to retire, and cashing out on their Toronto properties that had appreciated so well.

It’s a little hard with all the noise that's happening out there to determine any specific trends or to attach ourselves to one in particular. But we do know there are a lot of first-time buyers chomping at the bit to jump into the housing market. Perhaps they’re waiting for a better deal, for prices to drop…

Mike Pinkus: Or interest rates.

Reuven Gorsht: …interest rates to be more attractive. Yeah. Because again, at the end of the day, I always say—it’s just about the payment. It’s just about the monthly payment. Either you're going to get a good deal on a property, pay way below what it’s worth and save money with a lower payment, or the interest rates will come down and you’ll have a lower payment that way.

So there’s a lot of pent-up demand out there. People still know Canadian real estate is valuable. People want to jump on it. I think, like any market downturn, it’s all psychological, right? It’s very ironic that probably the same property that had 50 offers two years ago might be listed today, and no one shows up at the open house.

Mike Pinkus: Yeah. It’s all timing.

Reuven Gorsht: Same property, still desirable—and yeah, it’s all timing and all psychological. We just tend to go with those waves, and that’s what drives free markets when you think about it.

Mike Pinkus: Yeah. And Reuven, I’m kind of curious—how are you spending your time these days as the owner of a business, as a CEO of a company? It sounds like you have a lot going on. You’ve got marketing, you’ve got sales, you’ve got operations, you're dealing with things that are obviously legal. How are you spending your time? Like, what do you do on an average day? Like what did you do today—besides going on podcasts with people like me? What does the day look like for Reuven?

Reuven Gorsht: Well, for me, it's really a variety. I mean, I love and enjoy the building part, the creative part. So I try to generally dedicate my mornings to the creative side of the business—working on the business—for at least the first couple hours of the day. Then I try to get into some of the tactical stuff in terms of how the business is running, what are we seeing, what are the trends?

I'm still very active with customers and business development, and I stay very close to both our teams and our customers and partners. Because we're still evolving and building our product, I try to spend a good portion of my time keeping my ear to the ground, getting feedback, ironing out what needs to be improved within the organization, as well as looking ahead.

We’re fortunate to be in a state where there’s a lot of innovation happening—not only in our niche of the market but also in adjacent spaces. So I try to understand that and connect the dots. That’s where I would say most of my time goes.

Mike Pinkus: Yeah. I asked you the question also because I see you doing presentations. I always see on LinkedIn that you're quite active as a thought leader in your space. So I was just very curious about how you spend your time. And it sounds like you kind of block your calendar in the morning to plan out those higher-level priorities—especially around technology, because I know you’re progressive on that front.

Obviously, a big buzzword you're hearing about a lot these days is AI, and just using all forms of available technology to try to streamline things—especially tasks that are repeatable. You definitely are in a business model where there's potential for automation.

So how much can the current state of technology—like AI, no-code, and code—help solve the repetitive work that needs to be done in every single closing, versus how much of it is still bespoke, with edge cases and exceptions that you just can't solve yet without people? Where does that sit today, and how do you think about those problems?

Reuven Gorsht: That's a great question. The way technology is evolving, the answer I give you today might not be the answer tomorrow. But the way we think about it always goes back to: What are the outcomes, and what's the experience we’re trying to empower?

Ultimately, for us, it’s not about taking humans out of the loop—it’s about empowering those humans to add value where it matters most. For example, in a real estate closing, there's a lot of repetitive work—putting together documents, chasing down different pieces of data, copying and pasting between systems. That stuff can absolutely be automated. And when we do automate it, it frees up our team to spend more time with customers and partners—explaining things, answering questions, handholding them through the process.

Because every closing is bespoke. It’s unique. But we want to accentuate that bespoke experience. We don’t want people to feel like, “Hey, I just uploaded some documents and five minutes later my deal was closed.” We know people have anxiety, questions. So everything in our technology roadmap is focused on improving efficiency, and then redirecting those gains into places where we can have real human impact and competitive advantage.

Mike Pinkus: I tend to think about things almost identically to you, Reuven. These tools right now are—first of all—still in early days. It’s more like an Ironman suit than it is a replacement for a talented team. At least, that’s what I’m hearing from you, right?

Reuven Gorsht: Yeah. And again, there’s always going to be opportunity. We’re using AI quite a bit. But a lot of it is still early days—understanding how it fits into our different use cases, where we can leverage it where it matters most.

Because with any trend—whether it’s mobile, AI, or others—I’ve lived through many of these waves. And I have no doubt AI will be a game-changer. It will have massive impact, on our business and on productivity globally. But at the end of the day, it’s about rationalizing the signal from the noise. Making sure we’re not just doing AI for the sake of AI.

We're focused on picking the right use cases. We’re sticking to our strategy: Where can we amplify value? Where can we improve efficiency in ways that allow us to redirect effort and energy into the things that matter most?

Mike Pinkus: Yeah, I think it’s a great way to think about it. Because we all don’t know exactly where it’s going to land—but we have some time to figure that out.

Sure. My last question—because I don’t want to hold you much longer, I know you probably have meetings to get to today. You’ve been in business a long time, and you've obviously seen a lot from a venture perspective.

I’m curious—what are some points of advice you’d give to younger entrepreneurs? Maybe people who are starting their first business, or maybe they’re on their second and want to learn from that first experience. What advice would you give to someone who's looking to solve something in their own business and could benefit from what you’ve learned during your own scaling journey?

Reuven Gorsht: I think for me, one principle that I've stuck to—and it's cliché because it's been repeated a lot—is that you really gotta be all in and fall in love with the problem that you're solving. We all know entrepreneurship is a rollercoaster of emotions. It's a rollercoaster of different moments—good, bad, and really, really ugly stuff that happens. So you’ve got to be in it for the long haul. You’ve got to be in it for the marathon.

To me, what matters the most is that I wake up in the morning and I'm working on a problem that I’m truly passionate about. I know it's difficult and challenging, but I believe in solving that problem. That’s what gets me excited and gets me out there—doing presentations, podcasts, and really sharing it with the world.

It also helps during tough times. Everyone has their tough days where it’s like, “Maybe I shouldn't have gotten out of bed today.” But that’s when you remind yourself: I'm solving a worthwhile problem that’s challenging, and it’s not just an idea I came up with a couple of weeks ago and tried my best with—it's something I'm genuinely in love with.

Mike Pinkus: That’s amazing advice. And I’ve heard that advice myself—that if you’re just chasing money and you’re not passionate about the problem, you’ll start to realize that being an entrepreneur is 10 to 100 times harder than almost any job you could possibly have. And people don’t know that—or don’t realize it—until they sit in that seat.

So if you go into it just chasing money, you’re going to find out pretty fast that this is way harder than you thought. I think that’s incredible advice, Reuven. And I wanted to thank you for joining me. I know you're super busy, and you’re building an incredible company at Deeded. I see you guys growing and growing, and I’m excited because it is a better way to handle real estate closings. Real estate and technology are only going to become more and more important as time goes on—especially with the big housing topics you mentioned in places like Toronto and Vancouver.

Thank you again. And for anyone listening—where can people find you, Reuven, in case they want to get in contact with you? What’s the best way?

Reuven Gorsht: Yeah, absolutely. I mean, our website is deeded.ca. If you want to check out Deeded, or if you've got a real estate closing coming up or you're refinancing your mortgage, we’d be more than glad to help you. Best way to reach me is Reuven Gorsht on LinkedIn. I'm pretty active, so send me a connection request or a private message.

Mike Pinkus: Amazing. Thanks so much, Reuven. Really appreciate your time.

Reuven Gorsht: Thanks, Mike. My pleasure. Thanks for having me.

Mike Pinkus: Take care.

Mike Pinkus: That was Reuven Gorsht, the CEO of Deeded. Reuven shared some incredible business lessons during our conversation. Here are a few of the important highlights. 

Number one, you have to be all in and fall in love with the problem you are solving. Things are gonna go wrong constantly in entrepreneurship. However, the payoff usually happens in the long tail. So if you're going to endure the challenges long enough to reap the rewards, you have to be solving a problem you are truly passionate about, or else you'll give up somewhere along the way. 

Number two, building great partnerships with people in your ecosystem is critical for Deeded. That includes home buyers and sellers, real estate agents, mortgage brokers, and lenders. 

Number three, you must learn to view the service experience through the customer's eyes. Real estate closes have been around forever. However, Reuven and his team knew that the customer experience was not nearly good enough. So they built a solution to tackle all of the issues customers historically experienced on closings. Even to this day, they continue to apply the same feedback loop from talking to customers and continually improving the offering.

That's it for today. As always, keep scaling up and breaking barriers.