The Future of Real Estate Is AI — How Luke Morris Is Building It
With Luke Morris — Co-founder, CREXi & Founder, Capitalize.io
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In this episode of The Group CRE, Taylor Avakian sits down with Luke Morris — Co-Founder of CREXi and Founder of Capitalize.io — to break down how AI is transforming commercial real estate from the…
In this episode of The Group CRE, Taylor Avakian sits down with Luke Morris — Co-Founder of CREXi and Founder of Capitalize.io — to break down how AI is transforming commercial real estate from the inside out. Luke shares the early days of CREXi, how he helped reshape CRE workflow at scale, and why he’s now focused on the next evolution of AI-powered tools for brokers, operators, and investors.
From automating research to accelerating deal flow, Luke explains the problems he saw firsthand while building CREXi — and the AI solutions modern CRE professionals will rely on in the next decade.
If you want to understand the future of real estate tech, the next wave of automation, and the mindset of a founder who helped build one of the most impactful CRE platforms ever created, this episode is a must-watch.
You’ll learn:
- How Luke co-founded CREXi and changed CRE deal flow forever
- The biggest inefficiencies he discovered while building a marketplace
- Where AI is already outperforming traditional CRE workflows
- How automation supports brokers, researchers, and analysts
- Why PropTech adoption is accelerating faster than ever
- What the next generation of CRE software will look like
- How founders think about scaling tools for a legacy industry
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It was clear that most companies that weren't using this technology were going to need to use it. We left to start Capital I which is, you know, an AI powered data platform. I had dreams of working at Lennar. They laid off like 80% of their staff. I've got this auction company. Let's do it. 2 weeks later I started 2009. Think it's going to be super impactful. That would be a terrible. Basically I'm saying like 10% of all outstanding mortgages. That would be a meltdown.
What do you think the future of commercial brokers actually looks like? Do you see it where brokers are no longer needed? All right, guys. Before we get into today's video, I want to give a huge shout-out to Loan Titan, the exclusive lending partner of this channel. Loan Titan has been the number one lender in the Los Angeles area for years, consistently trusted by both brokers and borrowers. They offer mortgage solutions tailored to just about any situation, whether it's Fannie, Freddie loans, non-QM programs, construction loans, multifamily financing, or even land loans. They also offer in-house private money financing solutions for fast closings, distressed sales, or if you just need access to your equity quickly.
If you work at Loan Titan and you mention that Taylor Vekia referred you, you'll get $500 credited towards your closing costs. Their team is highly responsive, transparent, and genuinely easy to work with. Head over to loantitan.com and make sure you tell them Taylor sent you. Huge thanks to Cal Tezani at Loan Titan for supporting today's video and supporting the channel. Now, let's jump back into it. Welcome to the podcast. My name is Taylor Vekia and I'm here with my esteemed guest, Luke Morris. Luke, thank you for being here.
So, you are my first guest that is not an apartment owner and or a broker. And so, this is exciting for me because I've been diving deep into the world of technology. Um my first love came when I realized that technology can help me be better in my business. And with platforms like what you're building, got me very excited cuz all I'm doing is trying to differentiate myself. And so, I want I want you you to walk us through a little bit about your journey to which is your current company, capitalized.io. Um but I know that you started auction.com. You're like fourth employee and then co-founder of Crexi, which I know a lot of listeners are going to be familiar with. So, can you walk me through how we got to Capital I today?
Yeah, absolutely. And thank you for having me. First podcast. I'm excited. Um let's do it. Uh So, I I grew up in Southern California, went to USC, played volleyball um there for 4 years. Uh graduated literally at the worst time. I think other than like 1930 or something. Yeah, they they were saying, right? Like the summer of of 2009 was pretty bad because it was the GFC, right? Um And So, you're trying to find a job. I was I was I there was no one, right? Like no one was hiring. Like I had dreams of working at Lennar. Like I was good buddies with the COO of Lennar at the time. So, I was like, "Okay, maybe that's a good spot for me." They laid off like 80% of their staff. And uh ran into a neighbor of mine in Laguna Beach who's like, "Yeah, I've got this auction company.
We auction off residential homes like ballroom style like Eric Estrada." I don't know if you ever saw these commercials. Like they were doing like land in Louisiana and like homes, right? I'm like, "Sure, you're you're hiring, right?" Let's do it. And uh 2 weeks later I was It was like July 5th. I was right right after the 4th of July, right? I started uh 2009. And it was just uh me and a buddy and two other people in the New York office. Um we're the first wave of hires for auction.com, which was going to be the auction.com commercial side. Got it. Online only, not the ballroom style. Although I went to some of those to like see what it was like to kind of get the the uh the gist of what the auctions were like. And we were going to do it all online.
Um for commercial cuz unlike residential, I think commercial is less border is more borderless, right? Like people will buy a single tenant at least in New Orleans. Even if they're here, it's kind of cap rate based or multifamily. Get a property manager, right? Like you're buying a home, it's like typically within like driving distance, right? So, online was a likely uh smart and and good decision for Jeff and Rob to go down that path, right? So, and initially we didn't know what we were doing. I mean, it was like I remember being in a room in in Irvine with like no windows. Felt like there was no doors, either. It was like startup. A dungeon just like making phone calls, getting hung up on like, "I'll never auction." Like talking to a lot of brokers at first. We thought brokers were the the right model, but then
we ended up discovering that the servicers who um you know, the CMBS B-piece holders in the servicers were going to be the real golden goose of that business. So, like LNR, CWC3, those really opened the door. They had the volume, right? Cuz they were in the decision-making position to liquidate a lot of the CMBS, right? So, we ended up having this really big auction 20 Yeah, we had some good successes you know, moving with like Union Bank and stuff like that. But really there's this big Vegas note sale auction in June, I think it was of 2011. Um and kind of blew the doors off. I think we did like 300 million Whoa. day, I think maybe 2-day auction. No way. Notes only. Um So, we're selling the non-performing loans, right?
And it was really eye-opening, right? That people were bidding 10 million, 8 million bucks. Never seen the property, right? You could You couldn't tour it cuz it was a note, right? Non-performing loan.
Like and then they would drive around and like as is, where is, sight unseen bidding, showing proof of funds, bidding from everywhere. I think there was some guy in a boat, right? Like with Wi-Fi, right? Like bidding to buy these things. But it was eye-opening cuz it was like you know, commercial real estate if residential is 10 years behind every other technology, right? Like commercial real estate's like 10 behind.
People were willing to use the technology and bid from anywhere, which was pretty cool. And Wow. Uh it gave me a lot of exposure to different asset types. Right, I wasn't just selling multifamily. I was selling retail and we were doing self-storage deals or office deals, right? So, you got a lot of exposure to different types of sellers like what we call like private client sellers, like individuals who are moving deals. Um servicers, banks, right? So, there was a lot of great exposure and I got to live in New York most of the time, which was pretty uh
Were you um were you basically like your job was to obviously go find the people who are selling them, but were you also acting almost as a broker to get the transaction to happen?
the early on employees, I think we shifted later for later hires, but like I had to get my license cuz I needed to be able to talk to bidders. I needed to be able to talk to the seller uh appropriately about like, "Hey, this deal or this, you know, hey, the cap rate might be this or the square footage or the price." Talk about due diligence. Like you needed to be licensed as a salesperson
in order to communicate. So, there you were in the middle of the transaction. We had a broker on every single deal or loan sale advisor if it was a loan, right? Every single deal had a broker on it, right? Who knew the market, who knew the asset. So, I'd coordinate with them, coordinate with the seller. Bidders, talk to the bidders, get them excited, teach them on how to bid in an auction. It's very, very different. Yeah. Very, very different than like, "Here's my offer. Go back and forth. Here's my radio." Like best and final, best and final again.
So, it was much different. And it was you had to make a decision as a bidder within 2 minutes most of the time cuz most of the bidding happens in the last Yeah. Yeah. But there's a endless overtime. Within bids within 2 minutes. And actually we Crexi built we built an auction platform as well, which abides kind of by similar rules, right? But any bid placed within 2 minutes extends the clock 2 minutes. Most of the bidding like people wait and think they're going to snipe the deal at the very end, but it extends the clock 2 minutes, 2 and 1/2 minutes, or 3 minutes. Uh Think it at Crexi it's like 3-minute extension, right? So, you're seeing the price as the buyer. It's there. A million bucks, the next bid is a million 25.
Wow. Right? So, it's That's psychology, right there. Yeah, you get And it was It was proptech, right? So, Yeah. I've always been in proptech ever since 2009, right?
Even though I wasn't like engineering or coding or anything like that at auction.com. Like I was a salesperson, right? Mostly. Um But it showed me during that period like people were willing to use technology, commercial real estate people,
heads. It was right that we were shifting out of like, you know, what was in the '90s before that like, yeah, let's see the real estate in a newspaper and then you could see it online and then now we were trading it online. So, it just seemed like we were moving in that direction.
Yep. So, we um I think the being the younger guns like Mike, the CEO and founder, right? He we were very close. I think I was telling you like when he started must have been like 2010 and 2011 at auction.com, right? Like Jeff Frieden, the CEO, told Mike, "Hey, you're going to meet Luke." That was your first day. And like we've been buddies ever since. We've actually been friends about 15 years. And being young and hungry like Mike was one of the best sales people. Like he kind of started the private client group, right? He was amazing getting sellers to sell, connecting the dots, bidders to right? Like he was Mhm. probably one of the best that we had. Wow. And we always spoke like he was in
on the West Coast, I was on the East Coast in New York. We always chatted about how we could make auction better, how we could do things differently. And you know, ultimately I think Jeff and Rob, the the founders of auction.com I think they were just happy doing auctions, right? So seemed like there was an opportunity. I remember because Mike left and then I didn't hear from him. It was like the end of 2014. And then he showed up in New York and he's like, "Hey, this is happening. We're going to do it. Like you should come. I want you to be the co-founder. Like let's do this. Like I think we've got some momentum, blah blah blah." And I remember cuz we in New York, my office was on 5th Avenue. Like there was a Barnes & Noble, but there was like a Tommy Bahama.
And we went and we uh it was lunchtime or something and I'm like [bleep] I'm in like you know, let's do it. Took some shots. It was like maybe noon, right? And like took some shots of tequila or something like that. And then shortly thereafter I put in my two weeks and moved back from uh cuz we were going to start it in in in um uh LA. Moved back from New York like maybe a month or two later. It was like the beginning of 2015 and started working on Crexi.
Um I think that was like the beauty early on. It was like he everybody was hungry wearing multiple hats. Like I ended up fitting more into the product role. I was very excited about building out the technology. I couldn't I'm not a not an engineer. I'm not a ones and zeros guy, but it was I fell in love with like connecting with the customer, figuring out we needed to build and like setting requirements that engineers ended up building. Like
Yeah, like any a lot of like the core features that still exist on Crexi today. Like, you know, the searching and the property detail pages and like some of those really cool things we added. Like you can submit an LOI. We track, you know, we can host due diligence. We track clicks. We track visits. We track if they downloaded it, right? So those kind of ideas that we were hearing from brokers like, "Hey, I want to be able to like track. Like I own this listing page effectively on Crexi, right? Like show me what's going on.
Who downloaded due diligence, right?" Like we just took it to the next level as far as taking it from what was like maybe more of a billboard style into like a more active marketplace, right? With like better matching on when you search. Like monitoring each person's click behavior cuz when you go on Crexi today, right? Like each person has their own little machine learning bot that tracks everything they click on. So you might save a search and say you like retail, but if you're clicking on industrial the search results are going to change because we see that you're actually clicking. And you're clicking on OMs or you're doing due diligence and there's different scoring for different certain activities. Got it. Right? So it's very new age. It's not just like run the search and you see the same thing that I see if we're looking at retail in a market.
It might be price based. Right? You're we're looking at the same search in Dallas for retail whatever it is. Like based on my click behavior, we might rank listings higher because we believe you're going to click on those more cuz we're tracking what we're clicking on. Price or subtype potentially like net lease versus like a strip center or something like that. So we took it to the next level, right? And I was one of the people who ran product for the majority of my career there and like had to learn that over time. I was not a traditional product manager that ended up growing into like kind of running the team, right? And then we were all wearing lots of different hats, I think. Like I did some fundraising through the first three or four years as well or like everybody's kind of like I remember
making it happen and I think that like Mike and he did such a good job just like it wasn't necessarily that we found somebody that was like a perfect fit for whatever role. It's like we needed people that were humble and hungry. And they figured out on their own where they fit and we figured out where they fit, right? Like it was like the running through the wall mentality, right? Like we had an idea too of what Crexi where we could do and where we could take it, but it like um it was the hunger, I think, and like the willingness to take risk that ended up like cuz I think it like changed a little bit over time. At the beginning we wanted to be like more transactional, like alternate alternative style auctions where you could kind of bid on other terms, not just the price. Right?
And then it morphed into more of like we're going to be more of an active marketplace where you could list and list for free and then still take advantage. You don't have to pay to keep your listing up there, right? So it was like and then we charge premium for like more leads or more access, right? So it it morphed into more of like a pure marketplace over time, right? But because we were hungry and humble and willing to run through walls or sleep on a bean bag. Like I still have a kink in my neck for that. Time I slept on a bean bag when we first launched the website in October of 2015, right? Like I think um kind of ignorance was bliss or we were so naive that that was like a superpower for us if that makes sense. Yeah.
If we were listening to everything everybody said, like no, Crexi wouldn't exist. Oh, there's you know, CoStar, LoopNet, like you know, you shouldn't do it or there was Ten-X who were chasing kind of more of a transaction marketplace. Like wouldn't exist.
Let me ask you something because I think a lot of brokers and a lot of people are when they when they hear the word marketplace, right? In commercial real estate, it goes to one place and that's CoStar. And CoStar is the 10 million pound gorilla. Like they are just massive. And anyone who thinks that they want to compete with CoStar, it's it's like, "Okay, better you better buckle up." And so it sounded like you guys that was not even something you were considering. You were just trying to build something that the people wanted.
Yeah, we and I remember and we were talking about Phil Voorhees before we started that podcast. I can remember we had so many brokers come into this. We could not afford an office space, right? So we rented a house in Venice. Like it was kind of in vogue at the time. Snapchat was doing it. I think they until like even a handful of years ago, I think there was still a lot of Snapchat offices like on the Strand in Venice or whatever it is. Like 20 of them. They were just kept renting houses. And we kind of we couldn't afford 150 grand a year or whatever it was for the office space in Santa Monica and they wanted like 60 grand down. I'm like, "Well, let's just rent a house in like near the canals in Venice." Yeah.
So we were it was what we could afford and what there was some nervousness around like, "Well, if we have clients then what are they going to do?" Like we had hundreds of people come through and they loved it. Like even the brokers with ties and jackets on. They like I feel like they they'd be like, "Oh, I got board shorts in the car. Let Let me put my sandals on." Or like "This is great." They you know, and the show Silicon Valley was out at the time. I think that was helping maybe a little bit. Like people there was like some um I want to say like romanticism around the startup life at that time. Right? The Ubers, the Instagrams. You're seeing these like crazy valuations. They were just like and and brokers understand that too. They're following it. They're reading the news.
They're seeing CNBC or whatever and like there was it was ended up being one of the coolest decisions we ever made to go with the house, right? Cuz like it was so us. It was part of our culture. And the brokers loved it. So we had hundreds of brokers through and we basically so many times like, you know, it would be me and Mike and Eric in like this we called it. It was like this bootlegged conference room we had like downstairs which was like a cot it was like meant to be more of storage, but we like put a little tiny IKEA table and we painted the walls with like um whiteboard marker paint. And we'd ask the brokers in this in this room like, "Hey, just like write out your day." And we just asked them questions. And they just like "This is pain points.
I want this, this, and this." And like we would just like ask them tough questions. Like, "Why do you need this? Is this a must-have or a nice-to-have?" And like we just listened to these brokers and they were so appreciative. Like yeah, there were times like in the afternoons like we cracked beers or something like that and we would just like sit there and chat and just get feedback from them and turn that feedback into progress, right? So and we're so blessed to have so many of those brokers come through and and you know, I think we were just like broker first very friendly open to feedback. There's people that still call me today. I gave my phone number out like 10 years ago at Crexi. They're like, "Hey, Luke. Like can you help me? I got this problem." Okay, I'm not really there anymore, but and I loved it.
Like I give out my personal cell phone. Like you run into something. I think that was just like just a different way of approaching it, right? That we were so open to feedback. Um we did stay free in order to build which was like super challenging, right? At Crexi early on. I think we stayed from when, you know, really the company started rolling to when we started charging was like two and a half years. Right? But it built a really good rapport with the brokers. It allowed us to build a product that we felt was ready. And it like you know, maybe we just deferred revenue
Yeah. To Yeah, you're going to have your users, right? You're getting the users. You're getting it sticky so that when they when you did start charging, they're like, "Yeah, I'd happily pay for this cuz the service is so worth it to
us." And we were we were we were able to get the flywheel going, right? Like we needed to have a certain amount of listings. I think retail was our strongest at that time. We just started with like a lot of retail brokers, right? Like a single tenant net lease. Brokers, right? Like one of our investors, um Fernando at Lion Capital, like owned a bunch of retail. And
part of his like agreement when he worked with brokers was like, "You need to put it on Crexi." All right? So, like it helped us jump-start it, get it, got us some supply. It's like we were really good at retail to start. And so, when we had a lot of that supply, like enough supply, then there was enough borrowers, excuse me, buyers that started coming. And then there's more buyers that come, and then the listing brokers are happy cuz then they're getting engagements, they're getting deals, and they add more listings, and more buyers come cuz there's more listings. So, it's like it's the perfect flywheel. Yeah, the flywheel gets going. So, I think we needed to get that. Maybe it wasn't like spinning super fast when we started charging in uh February of 2018, but it was you it was clear that it was like starting to work, right?
over the last 2 years we've been working there." So, we had built up a good rapport with them. We'd built up credibility. Buyers loved it cuz they loved the how the search worked and how easy it was to use and like the alerts that we would send them. We're super good at sending. We're kind of the kings. I think everybody will laugh if they're listening to this podcast. They would think they're the kings of of email, but like it's kind of like, for lack of a better word, like people love the property porn. Yeah. Getting though, yeah. Getting the emails every single day. I think like on average, like if you're opted in to all the emails, you're only be getting 14 emails from us per day, but it's like hyper-targeted. Totally. Right? And people love it, right? Like They want to see these deals.
Like deals happening. So, we're it was just a little bit different, like much more active. It was like trying to give people matching. It was all about matching, right? So, Mhm.
um And then So, then obviously Crexi starts growing. You're doing this. And and more than recently and how we connected is you uh you co-founded another company called Capitalize.io. Explain to me what is Capitalize and and how did that come to be? Why did you pivot to want to start this new company?
Yeah, so first of all, it was like I I had joined uh Treasury, which was the venture firm, right? And I'd moved down to Orange County, so I wasn't operating Crexi at all day-to-day. Like I guess for uh like wasn't in the executive team, wasn't kind of participating in board meetings, like was it after I moved down from COVID, like 2021, to Orange County, from LA, right? Started having kids and stuff like that. And then uh joined the venture firm in beginning of '22, like part-time, right? Like I was still doing a lot of stuff for Crexi. And just started thinking about what I wanted to do next, right? I was really enjoying being part of the venture side, maybe that was something that I was going to do, is join Treasury or join another venture firm um full-time.
And the wheels just started turning, and started off maybe I was going to do like an apartment kind of AI-powered apartment. Um like almost like Stripe for renting an apartment, where it's like you could plug it in any website, and it's like wasn't necessarily like we were going to be I think it's like AppFolio or something like that. Like it was more of a software you just drop it in on any website, drop in a QR code on a sign. And so, that was something I was thinking about. That space is a little bit crowded. And then the market started to shift, right? '23 and a half, right?
The rates started going up. Um and it became really challenging for a for the financing side of the marketplace. But at the same time, there's a lot of private capital showing up. There's a lot of debt funds raising money. It was almost like shifting from the banking or traditional, like heavy regulated Mhm. type of clients, like trying to sell software into a bank is very hard. Like you got to be audited, regulation, right? It's like probably a sales cycle of like 18 months.
So, with the rise of all this private capital, the interest rates started going up, and I believe that if you're building software and you're like kind of chasing the market down, not a good place to be in. So, when you're building a company out of the kind of the trough or the bottom and going up, I'm like, "Okay, this is it's going to be tough in commercial real estate in general and finance." So, it's like I believe building something that's like cost-effective would be a good idea. Kind of riding the wave up versus like trying to time it or chase the market down. Right? And then the end of '23, I was in ChatGPT. Mhm. Dang. Okay, this is like this new platform that's showing up, and I think that after listening a million podcasts or reading a a bunch of articles,
like this is going to be the new platform. Like mobile or the cloud in the late 2000s, like obviously the iPhone and stuff like that. Like that was a new platform. Cloud kind of made it more possible. You didn't have to have servers in your office in order to like host stuff, right? In the '90s or whatever. Um so, this revolution was going to be let's see. I think it's going to be super impactful. But anyways, it just made it it was clear that most companies that weren't using this technology were going to need to use it. So, it was just perfect timing to So, between like, you know, I'd been at Crexi, I felt long enough. Um the state of the market being more challenging, the rise of AI, right? Support from a lot of people at at
Crexi and support from a lot of people at um within the venture community. It was just clear that it was time. And so, we left to start Capitalize, which is you know, an AI-powered data platform, right? And what will I believe be more of a marketplace, where we have brokers, mortgage brokers versus investment sales folks, like Crexi has, and lenders on the other side. So, lenders are the supply side of of loans, and brokers are, you know, bringing the demand in the form of borrowers, right? So, but what we do differently is like we use AI or AI agents to go pull in information more efficiently or with greater, you know, greater margin, right? Where you can rather than having a human, like interns, like my little brother was our intern at Crexi, who was like, you know, building listings for every broker who was too lazy to add their
listing. Now we can just deploy AI agents to like, you know, uh county recording offices or uh various sources of data out there, like the SEC has information, right? Around CMBS. You deploy the AI agent every day to go pull in information in, so we can do that, you know, the tools that we can use today at our disposal at a fraction of a fraction. Like it's just so much more cost-effective or affordable to be doing this now versus 2 years ago. Big change, right? And it's anybody who's used ChatGPT, like if you have even an image, which is like considered like highly unstructured data, it's going to pick it up 99.9% accurate. So, whether it's like a secretary of state filing on an LLC or like a mortgage deed, Mhm. it's going to be accurate 99.9% of the time of what's in that
information. So, it's just um it it became clear that it was it was good timing to go do it. And and brokers are hungry, hungrier even. You can make an argument when it's more challenging, a mortgage broker needs more lenders cuz they got to get more creative on their sources of capital because like unlike '21 through '23 and a half, like you could have like walked down the street, turned around, closed your eyes, and said, "Can I get a loan?" And like somebody would have handed you a loan. Yeah. Right. It was just crazy. Yeah. Like that ZIRP ZIRP period, like zero interest rate environment, right? It was just kind of crazy. 100%. Right?
Yeah, it was literally free money. Literally free money cuz it was it was less than the what inflation was. So, you were getting free money. What can Explain to me like in the simplest terms, what does Capitalize.io do? Like what what is the platform exactly?
Yeah, so we're we're aggregating all of the like data, right? Basically, every commercial mortgage data that is out there in the ether, and we allow primarily brokers to access it to see like what loans are maturing in a market, what loans are originating in a market. So, like is the market liquid?
We show like um loans that are still active that haven't been refied or haven't been transferred, right? So, it's it's a way, at least in its current form right now, to navigate this environment, which is more challenging, to, you know, see what loans are maturing. Maybe those are borrowers that you want to get a hold of, right? Like "Hey, this retail deal in Calabasas is maturing. You should get a hold of this borrower, right?" Which is I think really important today. And then once you win that business, like identifying how liquid the market
Cuz we're pulling in information more real time than a broker can find, right? Cuz we're pulling sending these AI agents and pulling the information in as real time as humanly possible. So, like you can go on Capitalize today and like we have loans that closed today on the platform. And that's really important in environment where things are changing potentially, to know like what loan is getting done.
Cuz if you miss that loan, and you're only looking at data from 3 months ago, that's a big difference, right? So, again, looking at, you know, potential areas to find business, maturing loans or active loans, or looking even at originations, right? And then once you win that business, then we have the most lender profiles. But they're lender profiles based off of what lenders have done, not what they say they do. Like every lender's website is like, you know, "We do everything nationwide, like every property type." Cuz they want the deal, they want like people to come in, like a bank wants depositors. So, if it's like a wealthy, right? So, it's like it's not a clear enough signal to a broker who has a borrower they need to place a loan. It's like, "No, who has done a loan?
the market?" Right? So, if you're looking at a real estate I was with a person who was looking at a deal in Miami this morning, right? Like, retail deals like Fort Lauderdale area. Like, who has done a loan of retail in the last Do you can look in the last week? Like, to show you a match We use an algorithm that matches you to the best lender based on their activity and deal volume and recency. So, like, this group has done the most loans recently and highest dollar amount, right? So, it's and we show like, you know, a match score starts at 100% and it goes down based on like those variables I just mentioned, right? So, and brokers use that and then they We have contact information of people at each entity, right? That you can get a hold of, right?
So, we've heard that, you know, I found a lender I didn't know was lending in the market or I found a lender in the market they didn't they didn't fund the deal, but they helped create competition with this the borrower's depositor, right? Like, you know, you're seeing National Bank of Florida, whatever it is, versus like and it allowed them to get better leverage by getting another term sheet from or I say term sheet, right? Like, getting another loan offer from a different lender, right? So, having that kind of transparency, I think, and having more arrows in the quiver for the broker, you look like a super It's like you're superhuman. It's like, I know who's done deals in the market. Look at how many people I've talked to. I have different loan offers.
So, you come in there and you look like as a broker like you did your job or you like a superhuman broker, right? So, I think that's really important and we've between Crexi and I think Capitalize, I got I get I truly believe that being broker first because of the complexity of an asset, I you know, is there going to be like some, you know, Terminator-esque broker eventually one day? I I It's tough for me to say, but I do believe brokers because of the complexity of an asset, that's why we're broker first. That's why 90% of all the subscribers on Capitalize are mortgage brokers, right? So, we're very much broker first, right? Because I believe they're the ones that know the space. They're boots on the ground. Like, they're going to be the best subscriber cuz they understand the market and it is a very complex asset,
right? 100%. There's And there there's so many nuances to it. And so, then I I guess I'm going to ask you cuz I think this is a question that a lot of brokers are having, too. And this was first proposed to me probably eight years ago when they said the broker's business is going to be a lot different in in 10 years. And I don't know how this guy knew it, but he knew it. What do you think the future of commercial brokerage actually looks like? On the on the lending side and on the investment sales side. Like, does this become where AI the everyone was cut out middleman, right? And the broker technically is a middleman. Do you see it where brokers are no longer needed?
Um that's a good question and I think I'll start with like backing up. So, it's like the internet happened, right? And late '90s, early 2000s, right? And people at that time probably like, "Oh, no, I'll just list it on Zillow." Right? Like, whatever was around Craigslist even. Like, I don't need a broker. I'll just like list my house on these sites, right? But like, if you look at the state of the market then, what the average commission was for a residential broker, um and now, there's actually actually more residential brokers and their commission is the same other than this ruling from NAR, kind of, right? Largely the same. Hasn't really changed. But I think what's happened is it's just made things more efficient, more liquid. So, there's been more transactions. The speed of close is faster. Like, it's been more predictive, right? So, I think that's what And we'll see
it's different with like AI. It's a It's a different thing, right? But I think it's going to just create more opportunity. Like, brokers can do more things faster. They can do things with greater confidence, right? So, I think that's the direction like where hopefully you see more brokers entering the space and more deal volume. Like, commercial real estate goes from like half a trillion in in deals like in an average market or like 500 billion of of property sold or traded hands in a year, right? In the US, maybe that number goes to a billion, right? So, that could sustain, I guess, technically double the amount of brokers or maybe, you know, it's the same amount of brokers just doing more business, right? And the liquidity increases and the confidence increases because AI allows you to like underwrite a deal faster or um respond to emails back and forth
from a lender faster or more effectively, right? So, I think that's more likely than like what happened to, I guess, like uh stock brokers, right? Like, that's a piece of paper. Like, they trade like just digitally like that. It's based on supply and demand. It's like, I want Apple, I get Apple stock, right? Like, it's it's much more liquid than two gas stations even kitty-corner from each other. Like, this gas station is going to trade vastly different. Like, what's the C-store doing? Who's Who's got the pumps? Which Which petrol company? Like, is it B&B BP?
Is it Is it Shell? Right? Like, what is that arrangement like? What's the ingress egress? What's the When was the loan originated? Like, what are the terms of that loan?
Like, there's just too many moving parts um with a commercial real estate asset that I believe there's always going to need need to be somebody in the middle that like sells confidence, that understands the market. And the ones that use AI, I think, are the ones that are going to rise to the top for sure cuz it's going to be here. It's going to be helpful and I think those that use it are going to, you know, get the lion's share, I guess. But I still I I still find it hard to believe that somebody with a lot of money like talks into Siri and says, "Buy this property." Yeah, like that's kind of what if without a broker like how else would it get done? Like, you talk directly and like there's a digital lawyer in the middle and like an AI broker in the middle and AI lawyer
in the middle. Like, talking about somebody committing like $10 million to a building or a million dollars or like you kind of want somebody that's going to like take you out to a closing dinner after and like get you a beer. Like, you want to put your trust in this person that's like not a robot, right? So, it's hard for me to see the world in like Maybe that's not what a venture capitalist wants to hear from from me, but I just find it hard to imagine that there's not a human in the middle just coordi- doing Yeah, again, maybe the role changes a little bit, but people want to be shaking hands with a human when they're talking about risking, which is what it is, millions of dollars. Hundreds of millions Some of these deals are like This is a billion-dollar deal, right?
Like, so, They'll be around is what you're saying. Yeah, I just I think again, maybe the role changes a little bit, right? Like it did back to that reference to like uh residential agent or even a commercial agent in the '90s. Like, they had to like market each property. Like, pay for the local newspaper the little tiny one in the back of the newspaper. Like, you're kind of marketing each property and if it's like now, it's just added on Crexi or added on Zillow, right? And you're kind of fielding lots of leads that are coming through and you're managing or you're spending more time like, who's the best buyer? Negotiating versus like trying to be a marketing person and a broker, right? So, now you can be purely a broker. Crexi already. So, it's like I think that the role is going to change a little bit, but
I still find it hard to believe. Somebody like I mean, I do venture, right? Somebody comes to me and says like, "I have this perfect AI broker." Like, show it to me. I'm very interested. I would definitely consider investing, but I want them to be able to answer the questions, right? Like, is it capable like of course I'm going to be looking at those as investments, right? But I don't know. I just It's hard for me to imagine not having that person that's going to be like, "This is the right deal for you." This is like shaking their hand, doing the closing dinner, going Yeah, like, I find it hard to imagine. Well, that gives me to it, I guess. Yeah.
It gives me confidence, for sure, because I I I do agree with you. I think none of us are going to be aware of the power of AI at this moment in time. Um and who knows what that ends up looking like, but I'm going to keep riding this horse as long as I can. And hopefully, given commercial real estate is 20 years behind everything else, we stay We have a little bit more time than than other things. Um walk me through exactly what happened in 2027 when there is 3.1 trillion of debt that's maturing. Like, paint me the worst-case
scenario. Um I don't see it I I don't think banks want to do the same thing they did in 2008 or servicers or whatever you want to call those. Like, um the lenders that or the decision-makers that decide to take the keys back or not. I think that they're disincentivized to pull back like just do I We want all this REO on our books cuz there's like you got to have a certain amount of reserves in your bank. Like, then you become like a real estate company. I think that's a mistake, right? But um I just think that there's going to need to be a reset, right? Like, even in the most and I talked to so many of my buddies that are like way more expert than I am in like owning They're the some of the best operators.
Whether it's a and if you even see like Brookfield they're the best office operator in the world and maybe I guess maybe Blackstone might have an issue with that but like they're handing keys back. It's like you could be the best operator in the world the multi-family property that used brand new construction in Atlanta
that's like the the performance of the actual asset is probably solid but the economics of the deals have changed. So I think what's likely to happen is like those properties are going to train change hands at a discount and I think ultimately the GP and part of the LP it's just they're going to get either restructured or wiped out. I mean that's I think what's going to happen they're just going to need to come have a come to Jesus moment and be like we should move on from these properties cuz I just don't think the lenders are going to want to take back that much real estate because it's going to it's a self-fulfilling GFC all over again like if all of a sudden there's like all the word starts to spread and all these properties yeah people are taking keys back.
everyone I don't I think I think 2026 is probably going to be like I don't want to say it's worse cuz a lot of these properties like like I said the performance of the asset
it's not like in the GFC where it was like when we were auctioning off some of these buildings like apartments building 50% occupied retail 10% occupied. A lot of the assets
So it's like I just think that the economics have changed therefore there just needs to be a a new ownership group for all these assets that come through and maybe work it out with the bank maybe there's an opportunity for some of these owners with these loans maturing to earn some promote later on or something right? Um I just don't see the banks being like we want $3 trillion of ROI then like Jim Cramer and these guys on CNBC are like the foreclosure rate went up and then like everybody starts to panic like I think that's that would be a mistake so they'll probably they've been trying to work these out. Uh-huh. 18 months? How long have they been like you can only kick the can down the road. The GP folks are trying to scratch out as much as of the equity as possible but I just
think that with interest rates being higher it's kind of inevitable. Unless like the lenders are like you know we'll basically take a 30% haircut on the loan and like totally
Yeah. I think they're going to want fresh capital from a new owner unencumbered by probably other properties that have economic issues as well or like financial structure issues right? So it's like I just think that they're just these assets are need to be recycled and I think they're going to be creative about it. I don't think I don't know if there's going to be like a GFC thing where they take back literally like three to that would be a terrible I think that's like 10% of all uh basically I'm saying like 10% of all outstanding mortgages in the US for commercial real estate they're like cuz I think there's like 32 trillion dollars or right maybe less maybe it's more on the debt side I think there's like 32 trillion plus of like asset value debt or not right?
So it's like maybe the asset isn't encumbered by debt that's a big that's a big number. Do you know how many properties or how many mortgages home mortgages for the GFC were in default? No. In order to it was like 6.5% So we're talking now over 10% basically like that would be a meltdown of magnitude of right? They don't not only that's a big number five and a half or 6% I forget I had a chance to read the other day I think it's like exactly 6.7% of all home mortgages around that kind of like GFC went bad. That's you like you read the news or the books you watch like the you know Big Short Big Short right? Like felt like it was 50% and they were like everything the world is burning down and they explain that in the book and in the movie it's like
in order for a meltdown to happen it like only needs to be a little percent. Right? So I think people are wiser now I think they'll figure out a way to to navigate it but I think just like it's unfortunate but those folks that just took on basically free money in that period of ZIRP right? They're just in that position where I think a lot of their equity is just in
trouble. So how does someone take advantage of it if you're a buyer or a broker? How would you how would you position yourself to take advantage of it?
Pick up the phone and start calling these folks with loans maturing right? Like get in front of them try and work out something with the owners right directly. Hey I know your loan is maturing in six to 12 months or whatever it is like let's work out a deal like there's so much how many I feel like there's a new article every day in the globe like at least over the last three years like oh we just set up a rescue capital fund separate like there's people getting creative right now right? So and you can't it's not like the interest rates I believe are going to go back anytime soon.
And if you look at Back to back to what? Where do you think they actually cuz everyone's talking about how the rates are going to drop 100 they're going
to cut the rates 75 That doesn't necessarily mean that cuz long-term rates are really anchored to 10-year plus Treasury right? We cut 75 basis points this time last year and bond prices went up so the interest rates even though we cut by 75 basis points have remained higher so don't think it's necessarily going to mean that if Jerome Powell cuts interest rate 25 50 basis points that that ultimately means there's going to be a 25 50 basis points on the whatever the average is right now like 675 or like SOFR plus 200 or whatever like So people are betting that over long period of time it's going to be a lot in order for those people with sub 3% interest rate some of them were like sub 4% interest rates you're talking about a long way to go.
I I think it's I I think that's why a lot of these deals need to be recycled because even if it the performance of these assets and the way they were underwritten and I talked to like a lot of my buddies in industrial and multi it's like even if it does go down to 4% or something like that like a lot of them expected rents to be at a certain place or that rent growth would be 30% year over year like the performance of the asset is still fine but it's not what they underwrote it back then so even if it does go down I don't know if the NOI even justifies it right? Like it's just like I I think it's just a combination of people getting wrapped up in this like crazy all these people were moving and like rents were going up and just
like because of the injection of the of capital and low interest rates it was like everybody was hiring everybody's moving rent like people were kind of flushed with cash with you know the you know whatever you PPP right? Like it was it was I don't want to say an instrument or just a yeah black totally that's a that's a good way of putting it right? So um that's I think that's
Like and a good a good way of putting it and this is probably extreme but I think it was like 55 California like I I forget the address in San Francisco right? Like a very wealthy Silicon Valley family bought 250 California in San Francisco where it was I think in 2019 sold for like 300 million and they bought it back for uh not bought it back but bought it for 60 65 million bucks. They lowered the rents 10-year lease something like crazy long-term leases to new AI tech companies fully leased. Now the building's fully leased crushing it and I think you just need to have that kind of reset new owners come in they're not trying to keep rents too high San Francisco was like totally inflated for rents anyway and you know it you have a reset like and when the
price moves from I forget crazy rents they're asking in San Francisco like 13 bucks a foot for a month or something like that it's just crazy and they're like it's now four. Yeah. And people are like four bucks a foot like I'm in and they put money into the deal like they didn't like just buy it and like they put money into it like fresh capital fresh capital came in bought it for 60 million they probably put a decent amount in whatever like 30 million bucks so they're in it 90 but they're like fully leased and crushing it right? Five bucks a foot not 13 so there just needs to be I think a little bit of a reset but I think that requires like rescue capital come in new ownership right? So it's a little long long-winded of an answer but I I just think and I'm not
in it day-to-day like some of my buddies that are like only buying multi or only buying industrial right? But that's what I'm hearing pretty consistently from a lot of people right?
So then what is the long-term goal for Capitalize? How do you look at where you're at today? Like what is the trajectory growth when you think about and we talked about this before this is you want to be planning on owning this for a very long time. So how do you think about pointing the company in a specific direction or do you want to be nimble and be able to float? Like how do you think about that?
directionally you don't want to be like too like this is the path. You want to be flexible same same thing we saw at Cracksy right? Like early on it's like we wanted to do something we were changing direction then we realized it was like this big opportunity over here like let's test it and then right? So you have like a vision of where direction is like we're going to be the best commercial real estate technology company or like listing platform in Crexi or like most active marketplace for commercial real estate, which was Crexi, like we want to be the, you know, AI-powered commercial real estate finance data platform. But I I want it to be something that's like really increasing liquidity, right? So
making a decision uh easier if you're a broker to um you know, find the lender faster, to close faster, right? Underwrite the deal potentially faster, do the valuation faster. So increasing liquidity using AI and data. Like we kind of talked about this earlier, right? And that's a little far-reaching, but um I believe if we're aggregating the right data, we're making the right connections, um we're using AI to make better matches to um build better, more effective tools for the broker. Um and I don't want when I say tool, I don't want people to think that it's going to be like, you know, how much of a labyrinth is Salesforce? Yeah, like I kind of want to be the anti-platform platform where it's something that's like if you have your own CRM, we plug into that. Or if you
a lot of people and it's funny cuz I uh when I'm like, "Hey, look up a deal. Show me like all the emails you sent or like where do you store all the information on deal you closed last year?" They go to their email and they like look up the thread where the email is. Uh-huh. And like, "Okay, let's link your email and like organize that information. Like you still operate in email, but we're aggregating the data for you and like allowing that data to be more actionable." So when I say tools, I want it to be kind of more of an anti-platform platform where they can get value quickly without like it's a lot to ask a broker to like switch from Salesforce to HubSpot. Like I download all the information, right? Like I kind of want to be something that's like more lightweight Mhm. and creating value
by using AI or integrations and having the best data, right? That then powers the broker to make them superhuman or the lender for that matter of fact,
I think eventually, but we'll do it in a way like I don't know if you've been on on Capital One, right? We were just getting about like matching a lender by looking at performance in a certain market, right? Like we want to have a profile on a broker. So the same thing it's like you're looking up Miami or whatever, it's like who are the top brokers in that market? So I want brokers to have a profile, right? We can kind of create a profile for them looking at like sending an AI agent or whatever to like Marcus Millichap's website, pulling it in there and then they'll claim hopefully a transaction. Like, "Oh, I did that loan last year." So we start building a profile on them, right? And then we'll start surfacing them if borrowers end up coming, right? And a lot of lenders don't like working
with borrowers that don't have a broker. Right? So we want to do it in a way that's like tasteful, so we can connect the borrower with a broker, hopefully. Cuz 70 plus percent of all deals loans, they have a broker on them. And lenders certainly like agency folks or life goes like they don't want to see a borrower Yeah. without a broker, right? So making sure if they do come, we're making that connection. Or we have a separate tool for a borrower that maybe they're just using to like get alerts, right? Like, "Hey, you need a new mortgage. Interest rates just went down." Like you should be talking to a broker. Like do it in a way where it's like we're not disintermediating.
No, and I don't want to be a broker. Like all of a sudden we stand up it's like, "Okay, now Capital One is a broker." Like I am not I don't want to be in the brokerage business. Like brokerages are in brokerage business, they're good at that. I'm good at building technology. They're good at brokering. I don't want to be the broker, right? So but if we can create value to the borrower by connecting them to a good broker in a particular market or give them sort of analytics around what's going around their property potentially.
And then when they get that alert like, "Hey, interest rates dropped." Like here's some information and here's a broker, right? Like that seems to be a better outcome for everyone.
What are you most excited about with the way that technology's going and like I guess with AI in general and or with the capabilities you're going to be able to do? Like what are you most excited about happening?
I think the speed at which uh a lot of these models are moving, right? Like and we're not building self-driving cars or like robots, right? Like we're taking data, it's real estate data. It's like the nomenclature is pretty standardized. Like it's mostly structured data even if it's an unstructured file. It's like, "This is the NOI and this is the interest rate." It's like it's not that complicated, right? So I think the the speed at which these models are moving or the AI agents are getting better like pulling the information in is really exciting for a company that's like mostly a data company, right? Like um so we're I'm it's probably better to ask my my co-founders or CTO, right? So um cuz he's the AI expert. I'm I'm kind of the regurgitator of what I heard conversations I'm having with them
or like, you know, using the models on my own or or reading an article or listening to a podcast, right? So um it's really exciting the speed at which it's moving and just for our business. I don't think like I'm saying like we're going to be in this like crazy AGI all of a sudden. I think it's going to take some time or where you have a robot that's your assistant. I think we're a little bit further away from that. But for what we're trying to accomplish, the speed at which the models are moving and how we can use AI agents, I think is really exciting. Which is which is I guess plays into my thesis and why it was time to build something cuz I felt like AI would be very helpful
What are AI tools that brokers should be using or people in the industry should be using that they're not already? How should they be thinking about this?
Um um they'll like somebody's like, "Oh, I'm available this date." And it like sends simple stuff like sends the calendar invite automatically. You don't have to go back and do it, right? Like and using chat using chat GPT or using Grok like to build an OM, right? Um or uh and and my buddy who's underwriting multifamily deals, he's like he's kind of cuz it it collects information on you. He's like, "This is how I like to underwrite." He's like putting his information in there. It's like getting pretty accurate at underwriting and like editing uh OMs or like crafting the right message or story if it's like the subheader of a uh of an offering that you have. Like just start using it, talking to it. Like it helped me build sh like shape some of the storytelling for Capital One.
Like I put in the board deck or I'd put in like original fundraising deck or uh notes that I've taken or sales deck that we have or um uh recordings like Gemini recordings on Google Meet and I'm like, "What do you think?" Like just as I was asking it like, "What do you think Capital One does? Like pretend you're a VC and like what would you want to hear?" It's crazy how it can analyze all this stuff and like and then I kept asking it questions. Like just start using chat GPT for like basic stuff and you'll start to pick up on on like the benefit of it, right? Chat GPT, Grok. I like chat GPT seems to be the simplest
It's your first go-to, your first For sure. I've moved it from, you know, on your iPhone from like just the regular um you know, you have like the bar toolbar at the bottom. Like it's in the toolbar now. It's gone from here to here and I swapped it out with Google. Yes, 100%. Right? And I'll just have conversations. I'll go on walks in the morning with my dogs or whatever. I'm just like ask it questions.
Like it's pretty cool. Yeah. Oh man, and you can the voice mode is I think super slept on, too. Like I just I'll I'll put on the voice mode and just start talking to it, and just brain dump, brain dump whatever I'm working on. And then after the brain dump, then I figure out how I want to organize it and structure it. But at least it gives me a chance to kind of reflect and and do everything about it. It it's some of the the I'm not the best prompter in the world. There's a couple guys I have this AI community thing that we started and my co-founder is much better at the prompting side. And I've used some of his prompts and I'm blown away. Like blown away at it gets me 80% of the way that I need to that would have taken me three, four, five,
Like just the efficiency of what you're going to be able to do it is incredible. And if you're not already exploring it, right? If you're not already checking out tools, what excites me, too, is companies like Capital One coming up and making me that much more efficient. How can I on every step of the process and what I do in the business, how can I be more efficient? How can I be better? How can I separate myself from other brokers by using these tools Using Crexi, using Capital
Exactly. Those those those kind of opportunities. Um what how do you grow a startup company? What is what is like the main thing if if someone listening or watching this wants to start a proptech company or wants to start their own thing, like what advice do you have for them?
The beginning is like it's hard. Uh-huh. Right? Which I think um is why cuz there's so many smart people in commercial real estate. I think there'd be a lot of people that are capable Uh-huh. of building a Crexi or a Capitalize. But it's tough when like you're a broker that's making a million bucks a year. It's like I have to go and make nothing. Uh-huh. Right? Like Yeah. Or make nothing and pay money out of my
own pocket. So it's like I'm not only making nothing, but the money is falling out twice as hard twice as fast, right? Cuz it's like I got to pay to put, you know, I got to pay for my meals and I got to pay for this company, right? So Yeah. You got to be prepared to sacrifice, I think, a lot. You could still have a work-life balance. I'm not saying like you need to lock yourself in a cage, but um you got to be prepared to make sacrifices and go all in. Right? Like because if you're not doing it, somebody else is doing it and you're going to be behind. Right? Um And I'd say like don't don't be afraid to make mistakes. Um you know, being online, don't be afraid to make those mistakes, right? And take risk. I mean, you're taking a risk by taking the leap.
But also don't be afraid to like test things or during the process, right? Test things and it's okay to make mistakes, right? Cuz that's how you learn.
But it's a it's a grind. Like be prepared to make some significant sacrifices. Like I said, like you see Crexi now, it's like a lot of sleepless nights or like I think one of my one of our early guys was like, "You slept on a yoga mat for a week." Like under his desk or like me in a beanbag or, you know, it was just like we were there 24/7 making things happen, running through walls. Like you don't have the resources of these great companies like Marcus and CBRE, right? Like you kind of you have to make it happen on your own.
Right? Well, Luke, I am very I'm very much appreciative of you coming on here, man. This is awesome. I'm excited to see where Capitalize goes. I'm excited to use the platform. Excited for other people to use it. Um and to see where AI goes cuz I'm a super nerd about it and seeing people like you create awesome tools that I can use gets me hyped. So thank you for that. And uh yeah, I know you're this is the first pod- podcast you've done. So It is. Thank you for How did I do?