The Derivative - Inside $2B of Chicago Real Estate: Tommy Choi on Housing, Migration, and Millennials

Episode Date: June 11, 2026

Jeff Malec kicks off “Chicago Month” on The Derivative with Chicago real estate powerhouse Tommy Choi of Weinberg Choi. Tommy lays out what really makes Chicago compelling as a place to live and invest—world-class food, underrated beaches, iconic bungalows, and relative affordability, while tackling the tough stuff around crime headlines, taxes, and politics. He breaks down post-pandemic migration, why inventory is so tight, how boomers with 2–3% mortgages and “Bank of Mom and Dad” shape the market, and why millennials are choosing flexibility and crypto over owning. Jeff and Tommy hit on stubbornly high rates, surging rents, condo special assessments, aging buildings, the limits of Loop office-to-resi conversions, and how AI and blockchain might (and might not) change the game. They wrap with a very Chicago detour into best burgers, dive bars, Wrigley in summer, and a few local hacks for seeing the city like a native. If you care about real estate as an asset class, Chicago as a case study in big-city risk and reward, or just want some elite burger intel, this one’s for you.Chapters:00:00-01:00=Intro01:01–03:47 = Selling Chicago: Food, Beaches, Weather, Taxes, and Crime Headlines03:48–15:57 = Inventory Squeeze: Boomers, Millennials, Rates, and the Battle to Buy or Rent15:58–30:54 = Life as a Top Realtor: Relationships, Weekends, and the Business Behind the Billion30:55–43:32 = AI, Search, and the Future Home Hunt: How Tech Is Rewiring Real Estate43:33–59:19 = Commissions, Class Actions, and Blockchain: Cleaning Up the Real Estate Game59:20–1:07:10 =  The NAR Shake-Up1:07:11–1:22:19 =  Chicago Like a Local: Best Burgers, True Dive Bars, Wrigley, Cherry Blossoms, and City HacksFollow along with Tommy Choi on LinkedIn and X and be sure to check out his website at weinbergchoi.com!Don't forget to subscribe to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Derivative⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, follow us on Twitter at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@rcmAlts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠sign-up for our blog digest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.Disclaimer: This podcast is provided for informational purposes only and should not be relied upon as legal, business, or tax advice. All opinions expressed by podcast participants are solely their own opinions and do not necessarily reflect the opinions of RCM Alternatives, their affiliates, or companies featured. Due to industry regulations, participants on this podcast are instructed not to make specific trade recommendations, nor reference past or potential profits. And listeners are reminded that managed futures, commodity trading, and other alternative investments are complex and carry a risk of substantial losses. As such, they are not suitable for all investors. For more information, visit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠www.rcmalternatives.com/disclaimer⁠⁠⁠⁠

Welcome to the derivative by RCM Alternatives. Send it. Hello there. All right, everyone. Welcome back to the derivative brought to you by RCM Alternatives, as hinted at, or maybe I should say threatened. We're doing a bit of a Chicago month here in June with guests doing financial-ish stuff in and around Chicago or with a Chicago firm or exchange.

First up, Tommy Choi, a friend of a friend. I've had the pleasure of debating Best Burger in Chicago with a few times. He also happens to do real estate in Chicago. A lot of it, like $2 billion of it. So thought would be good to have him on. I always thought people were leaving Chicago because of taxes and cold weather. But Tommy sets me straight. Send it.

All right, everybody. We're here with Tommy Choi. Tommy, how are you? I'm doing great. I appreciate you having me on here. I appreciate you coming on. Tommy and I are friends of friends, but we've hung out a couple times. And pretty nice circumstances.

One was a 50th birthday party in a, in a. kind of rented out part of a steak restaurant and one was on a on a boat yeah i i was telling uh our friend dan i'm like you got to get that boat again every year because you know who doesn't like a huge private yacht catered by r p m and hang out you know on a nice summer chicago day yeah just keep paying that bill so i got to start the hat i love it look i'm getting coca cola vibes which i'm drinking i ran to macdonald's got my uh standard diet coke before we started yeah I appreciate that. You know what?

So I have this thing where I obsess over classic iconic brands. And obviously Coca-Cola is one of the most classic brands and companies, especially in pop culture, too. And I always think, okay, when we make our team corporate swag, a Weinberg-Choi, my real estate company, I'm always like, I would not want to rock this stuff if I wasn't the co-founder of the company. because like I don't want to be a billboard for someone else's brand. So I said, you know, let's start build, making swag based on other people's logos. And I had this dream one day that I would have this wall just filled with cease and desist letters from the companies like Coca-Cola, which is wishful thinking. Like they care about this, you know, little real estate company in Chicago that we're making

these hats based on their logo. But anyhow, every year we make. these we make about 150 sometimes we do 200 and we give them out to you know past clients just supporters and what's cool is i always get people especially in the summertime uh when it's street festivals and people are out and about you know take pictures in the wild being like oh i just saw wineberg choi hat uh out there so so this is one of our one of our favorite ones the the the Coca-Cola one. All right.

I'm putting my name in for a... I've got you. I've got you. I'm going to give you a whole slew of these cool ones, so... I have the same dream. We've done a bunch of Star Wars infographics around investment themes, and I'm waiting for them to be like, hey, cease and desist. You can't use our characters talking about managed futures, but...

Right? Yeah. I mean, you know, I was going to say, John Lucas is probably just here, but it's not even him. He sold. It's all Disney now, right? Yeah. George Lucas. George Lucas.

Not John Lucas. John Lucas is, yeah, the basketball coach, George Lucas, yeah. So got you here for, we're doing a little Chicago month on the pod. You're selling basically Chicago day in, day out, right? Yeah. In your job. So let's start big picture of like, what makes Chicago great? What are your easy parts selling it and what are the hard parts selling it?

I'll tell you what. Chicago and I'm a lifelong Chicago and my family immigrated here in the mid-70s to the north side of the city, which is now considered north center. My mom has had a dry cleaner. Well, had. She's retired now for about 30 plus, 35 years in Boys Town. So that north side, and I live in the Southport corridor now, so, you know, that Lakeview, Northside neighborhood has always been home to me.

And what I love about Chicago, I think the easy sell is culturally, you look at the food scene. I think we're one of the best food cities in the entire world. From the beef stands, the hot dog stands, right, what they call like the working class like spots, which I love, to the Michelin Star Fine Dining. We're pushing the culinary scene. We have such a mix of diversity that brings all the different ethnicities and cultural cuisines to the city.

I think the biggest sleeper that a lot of clients, when we're helping them relocate to the city that they don't realize is how much beachfront real estate we have and the amount of beaches, you know, going from the city all the way up, even to the north shore, being by a body, a lake like Lake Michigan.

I have times where I bring people and they see the lake and they're like, oh my gosh, I can't see the other side of it. I'm like, yes, this is a largest body of water. Yeah. I'm like, and we have five of them. So, you know, this, I think those things, make it incredible. And as much as people don't like the winners, I think that's one of the greatest things of Chicago because when it comes this time of year and the city thaws out and the sun is out,

everyone embraces being out in the city. It's hard for me to travel during the summertime because I don't want to leave. This is the best time of year. So I think that's the plus side of why Chicago. go and then I can get into the affordability piece, right, for being one of the largest populated cities, you know, it's such an affordable city. To me, New York is way more intertwined with the water, right? You're either going in a tunnel under it or bridge over it. But you're in New York. You hardly ever see the water.

I mean, you could be up in a big tower, but like the day-to-air when I'm visiting, you get on the island, you're like, where's the water? So, yeah, that is a weird thing. And you're looking at the Hudson River. It's like, okay, it's not like the prettiest thing in the world, right? You know, and that's the other piece. And this is my like, my doomsday scenario of why I also think Chicago real estate is so valuable. You know, we're not by the east or west coast where we're dealing with erosion or even like, you know, Florida where they have like hurricanes going on.

I feel like my doomsy. scenario is that Chicago's pretty natural disaster-free. And I just think more people are going to start heading towards the middle of the country. And, you know, we'll be, we'll be sitting on prime investments. I always tell people that. I'm like, I love it because there's no natural disasters, just political pension ones. Yeah, exactly. Which we'll get into, Nick. But, like, yeah, but no mudslides, no, I mean, in theory, downtown, you could get a tornado. It's not really ever happened. Totally agree with you.

And my last piece, you should work in your bit of, especially compared with New York. I'm like, we have alleys. We hide our trash. Exactly. New York grid system. Yeah.

80 million dollar condo up there. And they have to walk out of their building next to all the trash bags lined up. I'm like, what's happening? It's so true. Allies are a key to have. And you know, even, even like, when you go into like Texas,

southern, you know, some parts of the country that have like limestone, you know, in their ground. They can't even dig out basements. They literally have to blast through the ground. I think things like that just make you very, uh, uh, and I also feel like I always felt the Chicago brick bungalow is such an iconic piece of real estate that's so unique to our city, uh, that is just, um, it, it was a way of

affordability and so many people have built generational wealth, you know, through that product. And it's one that still you see. And I hope to, you know, that we can secretly protect those bungalows and keep away from developers knocking them down. Do you know the history of that? Is there like many developers that did that? Or was it just that was the style everyone copying? No, it was a style that was copied.

But it was, you know, gosh, it was. I can't remember which war it was, probably World War II afterwards. The developers were starting to build that style of bumbleau. in the north side of the city, and it just took off. And I think part of it was also at the time, you know, back then families were, I think, smaller. They didn't have all the crap that we have today and the need for walking closets and non-sweet bathrooms obviously weren't a thing. So I feel like that was just an affordable piece of real estate that was all brick. And back then you can build the way that, you know, you can't build like that today without charge.

charging an arm and a like for it. So it just was a solution that filled a void that people needed back then. And it's cool to see those still stick around, you know, today. And it's a little west of where we live, right? You start driving and you could go blocks and blocks and blocks just passing home after home. So there's probably still a million plus of those. Yeah, there's a ton. You just see them more so, I think, on the northwest side.

you know, of the city. You see some in the south sides, a little bit west sides too. But, you know, kind of when you approach the city center, unfortunately, you know, the price of real estate has taken a toll on a lot of those. But, you know, I still love a good bungalow. And not the, but the classic Chicago line is a, what do they call it? Shotgun house. Shotgun, Sally.

Yep, shotgun. 25 by 125, you know, bowling alley piece of real estate. that we have to build. Is that more narrow than New York, say, or some other cities? You know what? I think I would say it's probably more narrow than even when you look at like, you know, the burbs of how, you know, there's, and there's obviously not like a standard lot size out in the burbs.

But, you know, I think it's pretty predominant to denser cities where you see, I see that in Boston. I see that in D.C., you know, where you can kind of touch your neighbor. but that it's definitely, you know, the standard in the city. And that was, you would open the front door, shoot a shotgun, I would go all the way through. What would, how, where'd that come from? You know, that, that's, that, that is beyond my pay grade.

I don't even know the full, but that's, that's, that's the story I've heard growing up. I don't know if that's an actual, you know, an event that occurred and whatnot, that took off, but, but yeah. And so what are the negative? What are you selling against? You know, I would say right now of late since a pandemic, the hardest, you know, sale or objection I come across when people are coming to the city is what they see and read in the headlines. And a lot of it has to do with crime. It has to do with this, you know, the stretch we had when Michigan Avenue, you know, was dealing with a lot of the smash and grabs and things like that. So I think that, obviously, in 2026, especially with, you know, everyone having access to news at the fingertips of their, you know, from their phones and whatnot. I think also politically things have been, become very sensitive and divided when it comes to, you know, to Chicago as well.

So those are really the things. And it comes down to like, you know, educating people. You know, I always tell people that, yeah, I mean, any major city is dealing with. with that, especially post-pandemic, but I feel like it's a lot of sensationalized headlines or a lot of times people don't read past the headlines and they don't get a glimpse of, you know, at what kind of volume this is happening, geographically, where is this happening and whatnot? You know, I have three young daughters that I've raised in the city and continue to be committed to raising them in the city. And so I think that it comes down to just an education, you know, around that.

But, you know, like I said, and what I mean by the political side of things is you start to see a lot of things that maybe are a little bit more progressive compared to how things are a little bit more, you know, in the center, maybe left to center, historically speaking in Chicago, when you see, you know, property taxes going up, you're seeing things like, you know,

transfer tax being proposed in the past, you know, being increased on higher priced homes. So things like that, definitely people become more sensitive to those headlines and they start to balk a little bit at whether they want to be in the city or maybe they want to exit the city and go into the burbs. But it's a lot of, and I think that's why there's such an importance to be working with a professional, a real estate agent who understands and that also lives in the community. so they can really tell you boots on the ground

on how things really are and what the climate and the market really share compared to what they're hearing and reading online or in their little echo chamber on Twitter, right? Yeah. And I was proud of you. You mentioned tax third. You'd think tax would be the number one thing.

You know, go ahead. I was going to say we were just down in Puerto Rico at a conference and people were basically trying to convince you to move there and only pay 6% tax. But, like, within an afternoon, they're like, this was the best bar in San Juan, the best restaurant and the San Juan, the best three things, like within an hour and a half. I'm like, now what? We just did it all in 90 minutes.

So I was like, I'd rather pay and have all the good stuff than save this money on tech. So I don't know. That's an unpopular opinion, but I think down deep, a lot of people feel that way. I'm like, hey, I can go to the beach. I can walk to see my kid play softball. to the park next door. And then I can go downtown and see a Broadway show and take in a nice meal. So, yeah.

Absolutely. Absolutely. The amenities, that's what I think a lot of people tie property taxes to like, well, what am I getting? Okay. So what are like a lot of times they think about school and, you know, they are. And that's the thing, right? Chicago is a very competitive market when it comes to schools and how to navigate that. But I always say look beyond that.

Look at the end, what you just mentioned, right? The amenities that the city provides and what that lifestyle is. You're either you live a lifestyle that's conducive to what the city offers or you don't. And if you don't, it's simple. It's, okay, then move to a different place that offers that, right? And so that's a good segue into what are you seeing, has there been this big move, especially wealth out of it, right? Ken Griffin famously.

Yeah. So a lot of big money was saying, another. enough of this, I can't handle this tax burden, I'm out. What are you seeing on that higher end, especially of like, is it net out or is it roughly the same? Good question. You know, it's, I feel like it's, we're almost at like a net zero. It seemed like, I think during the pandemic, it felt and seemed like there was this mass exodus. And I will tell you, you know, it depended on geographic where you were. The more debt, like, or the near north, like River North, Gold Coast, Stryderville,

they definitely saw more people migrating out. A lot of those people, though, were, you know, winterbirds, right? People that had a place in this city, that was more of a pita terre, that they'd come in, you know, during the summertime, that they wintered in, you know, in Florida for half the year. Those are the people that really, the majority that decide to exit out because they're just like, you know what? We're going to just stick around here full time in Florida.

And they were closest to that crime, smash and grab stuff. Exactly, exactly. And then you saw a younger group, that younger workforce that was like, oh, wow, I can be remote now. You know, I'll go to the mountains. I'll do the beaches. I'll do Southern California. And they just took off. But it was more of a temporary takeoff because when we started to see downtown

in the loop start to get back in a hybrid in person, we saw that younger, younger professional group come back to Chicago in the form of being a tenant or in the form of repurchasing, you know, a one-bed, two-bed condo in the city. So that definitely came back. And I'd say those collar neighborhoods around the Loop and the Financial District are definitely a little bit more contingent upon what that in-person workforce looks like because, you know, that's a whole drive.

of being in the South Loop or the West Loop or Fulton Market. Sure, outside of neighborhood amenities, it's being, having a short commute to work. And so that equation was taken out or that was taken out of the equation, you know, 2020, 2020, we started to see that come back now and those markets are starting to thrive and get better. You know, I'll tell you, right, we measure inventory in this nerdy term called month supply. And so at one point, the near north, River North, Gold Coast in Schroderville in 2021-ish, had 18 months of supply. So for anyone listening that's like, what is this nerd talking about?

Let's say nothing new came on the market. That means at that point, it would take 18 months to sell out those neighborhoods, right? Absorption rate. And to give some context, typically around. five months of supply is when you start to see a balanced market. So anything under five months is a seller's market. So 18 months was a very, very, a lot. That was more than during the last market crash in 2010. And so today, we're at about five months supply in that market. So it's come back a lot. Now, when you look at the north side of the city, Lakeview,

you know, we're at about four weeks of supply right now. So it's still very, very competitive and very much so a seller's market. But that those people exited out. But I'll tell you what, a lot of people from that, let's just say River North neighborhood during that 2020, 2021 period, they migrated out of River North but went into single family home because they wanted more space in a bucktown, west town. Right, I'm going to be working from home. I need more space.

Exactly. So it was a lot of just transferring around within the city. But, you know, like I said, today, we're seeing a lot of people that still want to go out to the burbs because they want to be closer to family. Not so much of like people like wanting to, I'm done with city life, right? It's just a matter of being closer to family or it's people leaving for a job. location. Yeah, they can't afford the child care. They need to get closer to families like, I need free child care.

Totally, totally. And that's part of also right now, I think, when we look at inventory, I think Illinois, I actually just, I just did a interview with Pritzker, the governor. We were talking about this, you know, because he's introduced this whole bill. He calls a build plan on how he's going to create more inventory. you know, Illinois is short about 150,000 homes right now. And you look at Chicago, you know, that's... What does that mean real quick?

I'm like, how do they calculate that? So there's 150,000 people looking for homes and there's not available? Yeah, it's based on the supply and demand of what the absorption rate looks like. Okay. Let's go some formula, but... Exactly, exactly. And I'll tell you what. You know, we were coming out of that last recession.

we were already behind, you know, nationally as a country, a new home starts. And we never caught up to that. And then the, the pandemic really widened that gap, you know, right now as well. But I think part of the issue is, you know, right now the largest group are the baby boomers right now that have, they're holding on to the largest amount. on a real estate. And part of it is that, you know, they have, you know, they need to downsize, but a lot of their wealth is tied into that real estate that they've owned for 40, 50 years. A lot of them I have conversations with and they're just like, hey, with where things I've

appreciated, I actually, this is my 401k. This is equity I have and I don't want to get hit with capital gains. because I know this is appreciated more than, you know, half a million dollars. And also the argument is now where do I go and what am I going to buy? And so there's a high price. I have to buy something else at a high price. Totally. And there's a there's this bottleneck.

And that's and right now, you know, I think that we, the, the prime someone, I don't know, someone in Washington, D.C. came up with this, right? the prime household age is 36 of when you're primed to purchase a home. And next year, we're going to see the largest amount of 36-year-olds our country's ever seen population-wise. So we're going to see another influx of demand that's coming in. And so you see that gap of supply and demand, and you see it in the data. It would be last year nationally. The average, the first time homeowner age was 40 years old.

It's the oldest that it's ever been since they've started recording and collecting that deal. Yeah, the millennials are like, I don't need don't. Right. And part of it, that's just getting pushed back. Yeah, and it's mainly because there's just no like inventory that's out there for people to purchase. So it's getting pushed back further and further. A lot of people will say it's affordability. There's a little bit of that.

But it's more so what I'm finding being out there. And listen, you know, our team sold over a billion. in real estate. We've helped 2,000 clients over the last two decades. So we've had a lot of at-bats, and these conversations I have are twofold. One, when you look at the younger millennial, the late 20, early 30s, those kids are making more money than we did at that age, right? So they definitely have the income around it. Speak for yourself, Tom. Exactly. I mean, Jeff, you definitely were, you know, top 1% early.

So part of it is they don't look at buying and owning real estate the way that maybe you and I did or definitely not how our parents did as the whole idea of like, well, if you're paying rent, you're throwing money away, you're not building equity. They get that. They don't care. They look at buying a piece of real estate as like that now ties me down to Chicago and now I lose my flexibility. What if I want to be in Boulder for a year?

or, you know, Southern California or Seattle or whatever, they think that real estate erases their freedom. And then when you look at the equity piece of things and real estate as a vehicle of building generational wealth, they don't buy into that because they're more into crypto now, right? They're just like, oh, no, I mean, Bitcoin will do that for me. I don't need to, I'm fine paying rent, you know, to have that. This is just one of my expenses.

I don't view it as an investment. Totally. So that culturally, it's very interesting how that that's flipped. And I think part of that's also pushing that first time home buyer age up as well. The other part, when it comes to affordability, it's not so much being able to afford to afford a mortgage. It's really the entry point. Now because it's become so competitive, more people are writing cash offers. I literally have this conversation every weekend when I'm reviewing offers.

I'm like, where is all this cash coming from? Where do these 36-year-olds coming up with $2 million in cash to purchase this single-family home, right? It's probably Bank of Mom or Dad. Yeah, exactly. That's exactly what it is. 12 million in Navidia earnings. And they're like, okay, sure, I'll carve a little bit out. Totally.

So part of that is why that first half. home buyer ages going up is that, right, someone that doesn't have bank of mom and dad, they have to, and they just, you know, have just, right, 20% down. They did it, how they were taught. They're just not competitive right now enough in this market. And what, what, so mortgage rates have been stubbornly high for what since 22 is when they to? Yeah, yeah, it was Mother's Day, 22 when they started to, right?

And then it was 2023 when I think the highest hit that I saw was 8% at one point. So in your experience, does, I've always thought the people just, they don't really care about the mortgage rate or the price of the house. They just want that payment. Yeah. Right. So like, I don't care which lever has to go up and down. I just want to pay four grand a month or whatever the number is. So is that, do you see that in your lived experience of like, that's how the move, how the metric works?

No, unfortunately not. I wish more people were more financially astute like you that looked at it like that. Unfortunately, people, they, and now we're in a place in 2026 where it's become more normalized and people understand, okay, rates aren't, you know, unless there's another global pandemic, we're not going to see rates into twos and threes again. Well, careful what you wish for. We've got Ebola is out this, I saw in the news this morning. Hanta virus. Might be time to refi, Jeff, you know. But you know, here's the thing. There's a lot of, when it comes to real estate, there's tons of FOMO that hits. And no one wants to be that buyer to say like, gosh, I miss down the lowest rates in U.S. history up at this point, right? And so when those rates are to hit 7%, close to 8%, there's a lot of people that exited out of that market because purely on FOMO, they're like, this is why.

And we try and educate like, hey, it's wild when you look at, yeah, you could have had a 3% rate, but you were not looking. You weren't in the market at that time. Look at your monthly nut. What is your carrying cost? Can you afford it? That's all that really matters. Rates will fluctuate. You'll have an opportunity to refinance if they drop again. So, you know, don't really think about it. Everyone tries to time things out. And we always tell people, time in the market is better than timing the market. It's better to just be in it today when you know you can afford it. This is a good rate, relatively speaking, versus trying to time everything when the rates go down. Because when rates go down, that means more buyer demand and competition go up, which means home prices drive up. You might not get it anyway. Right, exactly. So are you seeing that?

Thankfully we're past that. But have you also seen where people are locked in at that 3% mortgage and like, hell no, I'm not selling because that was the best deal I ever made. I don't care if the roof's falling in or whatever. Like, I'm keeping, I'm holding this house. That's part of it. That's part of also why we have this lack of supply is that those buyers that we're buying that have this 2%, 3% rate, they've dug this moat around their home and they're just like,

right? I have cheap debt. I never want to sell this property. And there's times, I'll be honest with you, right? I look at myself as an advisor and as a good advisor, my first question when I meet with someone who wants to sell is, do you need to use this equity? Do you need to sell in order to buy? If their answers, no, I tell them, you know, keep this property, rent it out.

You know, unless you don't want to be a landlord, we can mitigate that by hiring a property manager, but you have cheap debt. You might as well keep that. That's the best thing you can get. Yeah, exactly. And so, but a lot of the times where I find in those conversations, people, even if they don't need it, they just don't want to be a landlord. They're just like, I don't, I bought this to be my primary. I get it.

I'm good to sell it and, you know, make some good money on the appreciation. And I'll walk away from that 3% mortgage rate. What's your view on that in Chicago and elsewhere? I think a friend of mine in New York's paying like six grand a month for some one and a half bedroom-ish thing. Like rents seem like they've just gotten out of control. So part of that must be this dynamic you're saying like nobody wants to really buy house. So push up the rents. But is that sustainable?

And do you see people getting pushed into buying because of that? Here's the thing. We try and educate, you know, on our side, we represent a lot of landlords. And you're right. I've never seen a rental market this competitive in the last two decades. We have, I'll give you an example, there was a, in Westtown, a two-bed, two-bath that my teammate Katia, who's our leasing specialist, she had marketed for $3,800 a month in rent. she ended up getting 25 applications. And the winning tenant, the winning tenant,

they bid up to $4,500 a month. We tried, like, talking to them and saying, hey, have you ever, like, looked at getting pre-approved? $4,500 a month is pretty significant money you can borrow 30-year fixed, you know, mortgage. But once again, they were a young professional, and they were like, no, no, we're not tied to Chicago. Like, we like to, we get that, but we're okay paying this. We can afford it.

And we like the flexibility of, you know, knowing that in a year from now, we can go somewhere else. So once again, it's this mindset piece around it. They understand, yeah, I know I can afford buying, but I don't want to. We just did a podcast a little while ago with a former Major League Baseball pitcher talking through the path dependency of like, but even these young athletes, I'm making $7 million a year. I could spend a lot of money. I'm like, yeah, but you ain't only been making that for three years.

Right. Right. Like, it's better if you have this long term. So a lot of those people might be thinking like, I can afford this, but over 30 years can you afford it, right? Like multiply that up. It's just going to keep going up, whereas your mortgage will be locked in there. Exactly.

We're a couple old men screaming at this guy. Hey, come on. Bye. And then just as we're talking about rentals, what's your take on converting, right, it's happened more in New York, is starting to come to Chicago, converting old financial buildings and office buildings into residential? Seems to me I wouldn't want to live down there on LaSalle Street, but maybe somebody does. No, that, you know what? That's, I remember, uh, it during the pandemic, I was.

was Lori Lightfoot. She was making a big push about converting a lot of that office space that, you know, people were vacating because, you know, people were working virtual. And I'm like, that, there's an inventory issue, but also I always reframe it. There's tons of inventory in Chicago. What there's a lack of is what we call desirable inventory. And so part of that is also. I think, you know, as an elected official, this is what we always try and, you know, a lobby for is, hey, how do you make that undesirable inventory desirable? And a lot of that has to revolve around commercial corridors, right?

If you bring more commercial retail into a neighborhood, it boosts, you know, the desirability. And so the loop, to me, is a very undesirable place to live because there's just no, real amenities. There's not a much commercial quarter. There's sure great food halls. There are restaurants, but they're all, you know, 7 a.m. to 2 p.m. Right. Nothing really is open and conducive to the evening lifestyle. So I'm not a big fan of converting, you know, that kind of real estate that's in an undesirable inventory that in my eyes. Now, I think there's a great opportunity where you can convert some of that commercial office space into hotel, you know, that's, we definitely need more of that, uh, events based, more reason for tourism to come.

Yeah. But for, for residential living, I think it's tough. That, the other part of this too, Jeff, is that, you know, there's a point after two, that 2010 to 12 stretch where, you know, the, the financial and housing market just completely crashed, that a lot of developers, you started to see less cranes in the skyline that were being built for condos. The development that you saw were apartment, luxury, what we call Class A luxury apartment buildings. And part of that became more developers looked at that rental market as a more desirable product filling a void. And,

it was also a better exit, right? Where, you know, the occupancy rate in Chicago back then was around like 91, 92%. Now it's like 96%. You build a building for $30, 40 million. You fill it to 92, 93% capacity at Class A rent, which is, you know, the highest rental rates. You have a property manager that's running that, you know, five, six years later, you know, some PE company knocks on your door and says like, hey, would you take 300 mil? Right, exactly.

That's a pretty great return. You know, why would I build condos and deal with, you know, building the amount of phases, you know, having to pay the bank back at certain phases. So we started to see more people do that. The problem now is a lot of the times people pitched it as like, oh, yeah, and then if there's a need for condos again, someone will come and convert. these, you know, apartments, just like they did back in the 90s, into condos. The challenges, I always said this and has come to fruition today is that the way that these apartments were built,

the footprints were way too small because they packed in as many doors as they can. So you start to see these one bedrooms that are being rented out for, you know, like $2,500, that's, you know, 700 square feet, 600 square feet. You know, that's not a condo project. You know, that's not a condo I think someone's going to be paying $400,000 for, right? So you can't undo that. So I think, and like I said, rent is such at an all-time high right now. The business model doesn't support converting any of these. So, you know, I don't even know really if there's much room for conversion outside of really the loop.

And like I said, I don't think that's a really desirable product to, or an area to, you know, even convert. My other condo problem is this happened to us, Royalton Towers, you know that building? Oh, yeah. We lived in that for a lot on Orleans. Mm-hmm. Over eight years when we lived there,

basically the price of owning it increased like 70%, right? The electricity, all that, but the, I'm forgetting what you call it, like your monthly whatever to pay for the dormant. The assessments. The HOA went up from like $200 to $900 a month. Yeah. So then when we went to sell it, people are doing the man. Like, it basically, we sold it for the same thing over eight years that we bought it for.

But the buyer's like, well, it's eight times more expensive than on a monthly basis than it was back then. Yeah. So, yeah. You know what I miss is the horse stable. That's gone. I know. Yeah. Yeah.

Yeah. It might have been an insurance fire. Yeah. Yeah, it was a fire. And then the realtor who sold us that place gave your profession a ban. Because she's like, oh, see everything under the L. they're going to redo the L, and this is all going to be a dog park. And then, like, she was just making stuff up.

Oh, yeah, totally. That sounds lovely. My second condo question is, what do you do with all these 1960s buildings? Like, how, right, we saw Miami some of these condos started to fall down and fall apart. When and if that comes to Chicago, like, what do you do with all these really old buildings that have, right, some little old lady's not going to leave there? So you can't buy out all the tenants. Yeah, you know, I mean, that's actually a very good point that you brought up because we're actually seeing a lot. And with that, that was in Surfside, Miami, the building that collapsed, that had the structural issues.

Because of that, Fannie and Freddie, who, you know, they're the majority of, you know, the mortgages that are in the country. They're the ones that are underwriting all these. they have now, because of that, added into what they call a 22.1 disclosure, aka a condo questionnaire, that every loan Fannie and Freddie does, the underwriters have to send this to the property management company or the HOA contact that fills out basically the health of that H-O-A, right? And it's contingent upon them allowing, approving a loan to borrow into a building. And what they added ever since that tragedy in Miami that happened is the structural integrity questions, right? Asking about what the, one's the last time a structure engineer came out.

When's the last time you did any sort of facade work, things like that? And a lot of these buildings have not done it. And so you're starting to see a wave now of special assessments hitting a lot of these older condo buildings because they are having to do. a lot of this deferred maintenance work. And even buildings that have been, you know, pretty on top of it, you know, they're having to do more updated work to just stay compliant because, you know, some of these buildings that don't pass that questionnaire that Fannie and Freddie want, they deem them unwarrantable. And you cannot get, you know, conventional loan in the building.

And we come across that a lot. And so you either have to be a cash buyer. Now, it doesn't mean the building isn't safe and it's going to crumble one day. It just means it's not meeting their standards of what they're looking for in order to, you know, loan money into that building for someone to purchase. Doesn't mean it's not, not safe either, though. 100%. 100%. So we're starting to see a little bit of that where a lot of, you know, a little bit it's a challenge of how does a buyer then find.

financing maybe you have to go to a bank that's willing to do more of a risky portfolio loan or you know bank a mom and dad and they offer that cash loan in order to do it but you're starting to see some buildings that are are doing more of the work that they need to do is to deem them as warrantable and that's going to be showing up in some sort of form of a special assessment you know for that owner to take on. And I always envisioned in Vegas when they're like blowing imploding a casino and it falls in on itself.

It seems like we're too tight on these things. We can't do that. You'd have to buy out everyone and then like evacuate two blocks and then pay for any damage you make. But that seems like the answer, right? Like hey, this thing's put in a hundred years time to shift it to something else. Let's use this land. Right. I mean, because that's the thing. Some of those older buildings they can do the maintenance to kind of keep it up to standards, but they're going to continue to do that, right?

The only solution to do away from continual deferred maintenance really would be to start from scratch, and that's definitely not happening because there's just so many hoops to jump through in order to do that. So shifting gears a little, take me through, like, the personal side of what it's like being a realtor, right? Do you have to give up your weekends, you meet all these people that are driving around in your car.

Like, what's the personal stuff? Like, the pros and the cons? It's, I always tell, I have this conversation weekly when people call because they're like, hey, I want to do what you're doing, you know. And especially on like social media, a lot of times you see the highlight reels of realtors and you don't see like what it took to get to that or the behind the scenes. Yeah, or the billion dollar number you threw out. Sounds good.

Right. And so what I tell people is, it is like being a small business owner, right? I wake up every morning technically unemployed because I need to find new clients every single day. And if I don't have anyone to work for, I don't really have a job. And so it comes down to there's not really much. The real estateing part, you know, I always tell people the gap between the knowledge I have and the knowledge someone, you know, just starting out, you know, it's pretty wide, but that can get caught up in a day,

in a month, in a year, right? That's just like studying, getting at bats, understanding the nuances. That part's easy. The real gap that's hard for someone to catch up to someone like me who's on chapter 20 of their career is all about relationships. So I always tell people, right, real estate, that's the stage that we get to stand on, the industry, what we get to perform, while we're on this stage to our audience is cultivating curating relationships.

So it's really about the most successful real estate agents are the ones that are out there, finding new relationships, establishing new relationships, and really curating those relationships that turn into these real estate opportunities and at-bats to be able to see these pitches. And so how I always equate it to someone new is, you know, I always look at it as like, You know, if I'm meeting you for the first time, Jeff, you look like an ATM machine to me. And what I mean by that is, and for the younger millennials... Is it my boxy face?

You know, I always have to preface any younger millennial that, like, was listening to this. An ATM is like a brick-and-mortar Venmo, right? Let me tell you what an ATM. Yeah, exactly. We still go to these things. But it's no different than a Venmo, right, or cash habits. When you pull up to an ATM, now you tap your phone, you punch in your pin, you have two action items, right? You can either make a withdrawal or you can make a deposit.

And that's what being a real estate agent is on a day-to-day basis. It's finding these relationships. And when you identify someone isn't a jerk or an asshole, you want to establish a relationship. You have two choices. You can either make a withdrawal, right? Ask for business. ask for a referral, ask for an introduction, or you can make a deposit and provide value into that relationship.

There's really no right or wrong, right? One of my favorite books by Adam Grant, give and take, it talks about the mindset of a giver and a taker. And one person's not better than the other, but it's understanding just like if I make too many withdrawals from my bank account, eventually what will happen is I get that flash on the screen, you know, NSF, insufficient funds. Right. I don't have any money to take. And that happens in relationships. And we all have those people in our lives. How do we know those people,

who they are? They're the people when they call, we hit straight to voicemail. And we're like, what does this guy want now? What is he asking me for? I wonder why he's calling. So I always tell people to be successful in our industry, it's literally just making deposits of value into people. And when it comes time that you're ready to make a withdrawal, the beauty in this is not only do they allow you to make a withdrawal, they're giving you permission to make a withdrawal. They want to help you because they understand, well, what you want to take out of this relationship, you're the reason why we even have this capital in here because of all the deposits you've made. of course I want to return the favor and help out. That's really what my day-to-day looks like is how do I find people where I can establish that they're a good person that I want to build a relationship with?

And what can I do to make a deposit into this person's life to create value? And eventually what happens is when it comes time where I need to make a withdrawal, these people allow me to do that and they give me, they make a deposit into me by introducing me to good people to a client that maybe is looking to buy or sell real estate or maybe it's them specific personally that's looking to buy or sell real estate. And that's ultimately what being a real estate agent is like, right? It goes beyond showing properties, finding these listings, right, putting deals together. It's finding the people establishing the relationship so that you can be that conduit to helping

them with the real estate goals. I could change everything you just said to any industry, right? Yeah, that's sales. Life. That's true, right? Exactly. And we've all met those realtors and people in other business who within 30 seconds of meeting them. They're asking you for a sale. They're like, hey, I just met you. Like, what are you talking about? Exactly, exactly.

The work, like the Sundays, I've always thought of like, I could never be a realtor. I want to go to my kid's game. I want to do this. I want to see all that. But that's a little bit of the trade-off. That's a little bit of tradeoff. And part of it also, I'll tell you, is that's part of the come up. You know, like I don't show properties, you know, on the weekends. I don't really show properties in general. You know, part of it is because my focus is now just on the listing side.

But also, I always empower and coach agents to like be a business owner, right? When you are doing everything yourself, you're really, an employee working for the business versus being that business owner and and that big aha. Exactly. And where you hit that big aha in a career and you have that now the choice, it's a fork in the road to go the truly business owner entrepreneur's side or just continue to just work for my business is when you realize there's an inverse relationship between time and money. And sure, if I work on the weekends, show, all these properties and all these buyers, you know, in the evenings and the weekends when they're

available, I'm going to make so much more money, but I have zero time for myself. I'm probably going to be the worst father and the worst husband to my wife if I do that. I don't want that. But then when you realize, okay, I can give up some money by hiring leverage, hiring a showing agent that's going to take my clients out to physically show the properties and I can still negotiate because that's what my strong suit is. I can hire an assistant to take care of my inbox and my calendars. I can hire all this leverage that I take away from my bottom line, but now it gives me more time to go to my kids games, to be a better husband to my wife. What I found is that the ROI in that investment ends up coming back tenfold. You still don't

really lose income because now you can take on more clients because you have more time. to do this, you're more efficient, and you can still have a personal life and take care of yourself and your family. It's just that a lot of agents, because it's such a hard industry to make it in, when they start to see that income coming in, they become protective around it. Yeah, and they're just like, no, no, no, it's okay. Like, my kids won't remember me not being here because, you know, they'll have this, you know, nice lake house they can go to later. life and you're just like, I always try and tell them, like, trust me, they will remember you want to be, and you will remember that you weren't there. You want to be able to be there

and paying someone 50 grand a year to leverage and getting back that time, trust me, you're not going to miss out on that income and you're going to see a return on that investment. Yeah, and that's like the plot of every rom-com. Like the guy who, takes all that for granted and gives up the time for the money and like it never works in. But you like as you were saying all that, I was thinking of AI, right, who now is kind of helping that instead of hiring these two people, maybe use some AI. So what has that done to your business in particular and just overall? I think Zillow, right, launched something and they were buying houses based on its model that

went terribly wrong. Yes, that did not work out for them. Yeah. So what have you seen there? Is it helping you? Is it, what do you see in the future for AI in real estate? Yeah. I'll tell you what.

AI is how we've implemented into our business. It has helped with our profitability because it's taken workload off of our operations and admin team that's allowed them to focus in elsewhere that's brought in more revenue. We're still not at the place yet where I see it where it's going to replace an actual human role where I can say like, wow, I can get rid of this person's salary and I can now just have AI fully do that. We could get to that point one day. But right now it's a tool that makes us work more efficiently, more effectively and more profitably. And I really like that. I think the opportunity for our industry, the real estate space where AI can really change is from a

consumer standpoint. Right now, we're one of the few industries where, you know, how you search for a home is still the same way it's been forever. What's your price? What's your zip code or location you want to be, how many bedrooms and how many bathrooms? It's archaic, in my opinion, because right now, if we log into our Amazon accounts, our Netflix accounts, even like our social media, our homepages look different because there's an algo running. Yeah, exactly. Predictive analytics is taking over and it knows what to recommend to you. I think the future of real estate and the company to get to do this is going to really, win is change that consumer experience where you log into my website or Zillow or whatever,

and now they, the algorithm will start to tell you what properties you will like because they should be able to scan the data of, wow, look, based on your, you know, 12-month Grubhub order history, you're ordering a lot from Oshaval. Maybe you should be living in the Fulton market, right? Based on where your Uber, are coming from and spending, you know, time from work or socially, maybe you should be living here. There's so much data out there. You could even have like a little counter that's like, hey, if you lived here, you'd save $812 a year on Uber's. 100%.

I really think that the home search is so broken. And I get it, right? It's got to be, at the end of the day, it's got to be anchored by price point and bedroom count. But I think that can be layered on after the fact once someone. an algorithm, predictive analytics tell you like, I think your ideal neighborhood is, you know, worker park because of what your personal life data shows you, right? I love it.

It's like you've ordered seven million paper towel rolls. You need a lot of storage space. Exactly. Exactly. You have corporate Costco membership. You need a pantry, right? But like part of home buying is such an emotional. it's like the biggest emotional financial decision too, right?

So somewhat yes, but then it's like, well, if I'm just data, or maybe do you have customers that are just database? They're like, I don't care. I don't need to see the pretty house and have that warm, fuzzy feeling. I just want this price and this number of rooms. Yeah, I mean, it is 100% still very much so, you know, an emotional piece of it. So that's why it's like when people say, you know, and a lot of it, I think it's just, just like click bait and rage bait, I guess that's my 14-year-old daughter would say, of article saying like, oh, AI will replace the realtor one day, you know, because, you know, a machine can negotiate and do all this stuff. I'm just like, there's just so much emotional navigating nuances to a deal and also a human element that, you know, maybe some of the communication can be replaced via AI, but a lot of it still has to be.

you know, in person and, you know, conversations, reading people emotionally on a situation that I just don't see that ever fully taking fruition. And it seems like we've already, you've already survived the hardest parts, right? Like 20 years ago, when did we start being able to search online and see all the pictures? And so it seemed like, to me, it was like, oh, everyone's going to be able to do this online. Like, real estate commissions are going to come way down. You won't need realtors. I just find the exact place I want and then use them for the last mile, so to speak.

There was a time when the MLS went from physical paper copy books where you literally, like, you didn't know until Monday morning what new listings were because they were printed to being digital online. And the entire real estate world thought the sky was falling. We're going, there goes real estate. Like, it's going online. and the MLS is going to be digital, like, what? And everything's worked out, right? So, you know, I just think that a lot of people,

especially in my industry, is just they don't like change. And they fear it. And it's weird. My buddy in Palm Beach was talking about the massive. That place has gone crazy. Oh, my gosh, yeah. And he's like, and we have these friends from high school that couldn't tie their shoes,

and now they're making like tens of millions of dollars selling real estate. So we were. both yelling at that a little bit, but he's like, and the crazy part is the homes have increased 10x, but the commission hasn't decreased 10x, if that, right, it's come down to maybe a hair and maybe down there at like a $100 million sale or $50 million, it's quite a bit less. But that's a good, like, lever for you guys on the other side, right? As a businessman, like, hey, the prices go up and we stay the same. Yeah, exactly.

All right, I had one more thing with the national piece there you were going to tell me about, because you were on the board of the National Association. or something like that, right? Yeah, yeah. So current board of director. There you go. So there was a big class action suit. What was happening with all that?

And how did that check out? Oh, yeah. That was another sky is falling moment in our industry. You know, ultimately there's a class action lawsuit of, of home sellers who felt that, you know, the way that the listing agreement used to work. was, you know, Jeff, like, let's say, I'm pitching to sell your home and how we would pitch and explain the commission structure was that, you know, hey, it's, you know, commission's going to be 6%. Of that 6%, though, I'm going to be paying 3% to the buyer's agent that brings a buyer, right? But I'm in control as the listing agent of receiving that full 6%. And it's on me now to co-operating. operate and give the other 3% to the buy side.

Well, I'm sure there were a lot of people that weren't fully explaining it, you know, that way. And a bunch of sellers felt like, hey, one, like, this is really confusing. Like, you know, you told me that your commission was only 3%. Right. But now you're keeping like 5% of it, like what's going on. And then the other part was that. The mindset was, hey, why as a home seller, why am I paying the buyer's agent to bring a buyer here?

Right. So, you know, what happened from that, you know, they had to settle that lawsuit. And part of the settlement, you know, the side of the monetary financial side of it was changing rules around that. And so, or business practice, as they say. And so now we're in this world where, you know, they have. separated the commission. So now when I'm talking, speaking with you, Jeff, you know, our listing agreement now, we're just talking about how much you're going to compensate me for my professional fees, you know, like, hey, you know, 3% is what, you know, you're paying for. Now, the buyer side,

they have their own agreement, a buyer broker agreement, which, by the way, is nothing new. That's been around forever, right? We've always practiced that on our team. But a lot of people didn't because some agents are just scared to talk about how they make a living, which, you know, I'm like, you're in sales. I don't understand that. That's not taboo subject, right? You offer a service. You get compensated for service. So now that's become in state of Illinois.

I was the president last year of the Illinois realtors, you know, which were, I think, like the fifth largest association in the country, 55,000 members. and what we help lobby to do is change and make it an official license law rule in Illinois where you have to have a buyer broker agreement, right? Because it's more transparent for the client. So you have this agreement now where the buyer's agent has with the buyer saying like, hey, we're going to ask the seller to cover, you know,

my professional fees. But if they don't, you're on the hook for it. And, you know, everyone was like, this is a big deal because now this changes thing. Yeah, that'll drive those to zero, basically. Right. And, you know, also, So part of the other rules change was that, you know, in the past, in the MLS, it would state and showcase how much the buyer, agent commission was that was being offered.

And so they said, do we got to take that away too, because that could create bias. Because if now a seller's only willing to offer a little bit, it's going to filter. A realtor will filter and not want to show that property, right? So that went away and they thought the sky was falling. Well, fast forward now it's been a couple of years that this has been in practice. And, you know, guess what? Everything is pretty much the same as far as how things we've been done. I think it's even better now.

And I'm one of the few that is happy about how the settlement because it does create a lot more transparency for the consumer. and I think that's very important. And it creates more of a fiduciary. And it's very clear like, hey, I represent you on the by side. This is my professional fees that you compensate me for. Listing side, this is my fees. This is the value I bring. And there's no confusion around it.

And so I think ultimately it's become a good thing. I think what the attorney that represented, you know, these angry sellers in this class action lawsuit, thought that this was going to eliminate the need for commissions now. You see, no one's going to see value in the realtor. Obviously, that guy was wrong because we have not seen any change. We haven't seen any devalue of professional fees of what consumers want to pay. If anything, it's validated that consumers realize this is the largest physical asset

that one purchases in their lives and they want to hire. a professional to represent them and advise them in this transaction. And now you made me think of blockchain, which will be very quick on. But where do you see that all happening of like, hey, your title is on the chain and we can cut out title people and that will bring costs down to transfers and stuff? I am such a big proponent of blockchain. And I think that it's so needed in the space because it keeps, I mean, yeah, ultimately like, there's really no need for title insurance after that because you know it's a clear and free title. Right. Everyone can see it on the chain.

Yeah. You know, it's been talked about for so long. And the reason why it's not been adopted, there's just too many hands in the pod when it comes to the workflow. Because it's, the title has to be, if the mortgage has to be able to also underwriting has to be in sync and accepting of blockchain technology in order for the, title to be accepted that way as well. On the real estate side, I think that we're the easiest side to, to accept that. Then you have the nuance of Illinois being an attorney state. So real estate transactions have an attorney involved. So now the attorneys, the way they make money is through the title insurance policy, right? So how does that work? So I think there's just too many cooks in the kitchen right now from a policy standpoint that doesn't allow that.

to happen and also a capability part. But also, when I hear that, I think about, you know, two days ago, I ordered a sandwich and a little cocoa pulled up, robot brought it to me. If they can figure that out, I'm pretty sure we can figure out ways to, you know, incorporate blockchain into the real estate transaction. I live right here at Hamlin part and they bought a AI robot that chalk saw the field. for the baseball game.

You're kidding me. We used to have to wake up an hour ahead and do all this truck and take us an hour. Now this thing does all four fields in 15 minutes. That's incredible. Right. Great use case. All right, we're going to get on to some fun stuff. Any last real estate thoughts before we talk?

No. Fine dining. No, I'm real estate it out. I'm real estate it out. All right. You're a foodie, as you alluded to in your first answer, why is Chicago. We've compared burger list. So I'm going to have you do four Mount Rushmore's.

Oh, gosh. I think you're up for it. But yeah. So I like, I stole this from Bill Simmons, Bill Simmons, not Ben Simmons, Bill Simmons, instead of picking the best, right, he says Mount Rushmore. So you have latitude. You can do four instead of one. So we'll start easy.

Burger, Chicago burger joint, Mount Rushmore. Okay. So I have to preface here. Because my, I think the most important category for me, me, what I'm looking at burgers. Yes. It's cost. Because right now, people will throw out Armitage Ale House, which is all part of, you know, the hog salt with Josh Havall, right?

And everyone loves that burger, which I think is not really that great anymore. But yeah, sure. If you're using Wagyu or A5 meat and using the best ingredients. a $40 burger better taste freaking good. So when someone says, oh, that's, you know, Armitage Jail House burgers the best, I'm like, yeah, for $35 bucks, it better be, I don't count that, right? I think price is a big piece, affordability.

So I say that because for 100% sure, on the Mount Rushmore burgers has to be Red Hot Ranch. Which is right up the street for me here, Ashland and Barry, yeah. Listen, a double cheeseburger and you get fresh cut fries for $8. And it's a great burger. It's more of that in and out style. I think it's one of my favorites.

It's one of my ones I always recommend to people. You told me and I still haven't been, even though I drive by it. You got to go. You got to go. 20 times a week. And I'll tell you, the great fried shrimp too. So Red Hat Ranch is on there. My personal favorite tasting burger in the entire city is a Mott Street burger.

Okay. Have you had Mott Street's burger? Yes. We talked about that way. Yes. It's different. It's definitely got a little bit more of that umami to it. That's definitely on my Mount Rushmore of burgers.

I will say, I think the best smash burger in the city of Chicago. is Levitt Street in. Their smash burger It's like right west of the highway over there. Yeah, yeah. And they just, they just like redid the outdoor space too.

They are on my Mount Rushmore. And my fourth, speaking of, in this world where everything is a smash burger now, it is refreshing to just get a nice, thick, pub style burger. and I think the best thick pub sal burger,

legendary spot, rootstock. Have you had Rootsox burger? I've not been to Rootstock, man. Okay. All right. You have to go to Rootsok. It's Humble Park-ish.

And they have just an incredible, thick, juicy burger that's, I think it's like a, it's definitely a short rib chuck. blend and it's definitely like a 70-30 so you got a decent amount of fat in there that that brings that juiciness that burger is phenomenal i will tell you you didn't ask for it but you know the if you know just like you know trump wants to be the fifth president of yeah if there's a fifth burger i will say when they're relatively new and it's a pop not i don't say a pop-up but they're

inside of have you ever been to the long room It's a bar. Yeah, yeah. It's next to Popeyes on Irving Park and like Ashland. In there, they have a kitchen. And the burger spot that's in there is called Cassius Kitchen. Okay. Holy crap.

This burger is phenomenal. And it is definitely the guy Travis, who owns it and is the chef, he has an extensive, like, culinary background. he got burnt out of just the bureaucracy and just the whole fine dining world and just said, I just want to make burgers. And he just did it, bet on himself. And this burger is like, it's incredible what he does. You ever thought of doing like a Dave Portnoyd style

going around? You'd be great at it. I am anti-rating food. Because it's such a subjective thing. Personal. Yeah, exactly. Like, you know, my favorite sandwich of all time is of McDonald's flayo fish. Some people gag at that.

I think it's a perfect 10. That is literally like the pinnacle of sandwiches for me. So, you know, that's why rating food, I think, is kind of silly. Just do it and turn off the comment. You'll be fine. Yeah, there you go. All right. Next, dive bars.

Mount Rushmore of dive bars. Man, I will say, okay I don't I it's like like it's funny because like now I feel like the hipsters thing is to make your bar feel like a dive bar but it's like also like fancy cocktails now but I'll tell you and it's going to be there's a little bit of food connection to it okay so my first favorite dive bar is best intentions have you been there yeah I mean once again because they have incredible cocktails and cool food but yeah but the drinks are really great there. I like Best Intentions a lot. They had some homemade, like, trail mix in this little bag that I was just like, what is this? Right?

So good. Yeah, it was like, who does this? I love Best Intentions. There's an awesome bar in Bridgeport called Electric Funeral. That is... Never been. Oh, my gosh. It's so divey, but also very... It's like a classy divey.

It's great. It's a great spot. It's just... got, you know, cast of characters, phenomenal drinks and cocktails. I really like that. My, I think, creepy favorite dive bar is L&L Tavern. And I say it's creepy because that's where John Wayne Gacy and Jeffrey Dahmer used to hang out at and they live by that. But L&L Tavern is just straight up like dark, like, I always not, it's like I'm thinking of a Delilah, but no, it's in Lakeview on Clark and just north of Belmont. Yeah, yeah, yeah.

L&L Tavern. I tell friends, if you ever go there and you run into me and I'm by myself, like, call someone, I need help. Right. That's a place where I should not be hanging out by myself. But L&L's a really good one. And then, you know, once again, I don't know if I would call this. a dive bar, but small bar. Yeah.

You know, it's been around forever, but they just have new, they're under new ownership now for the last, like, I don't know how many years, but I love small bar. And part of it also is because I love, uh, the cheeseburger that they serve out there, Patty Pleaser.

Yeah, the onion burger. Yes. Yeah. I've had, but also, we had like five vodka drinks that we ordered there. And it was still,

I think they're full priced, but small. Yeah. I was like, wait, these are small drinks. Why is the bill so big? Like, go, don't worry about it. Exactly. Lovin.

We're running out of time. So I'm going to, last one, open dealer's choice, your Mount Rushmore of places to go. I won't even say restaurant, bar, places to go in Chicago. Wow. Places go. Well, I'll tell you what. You know, this one might sound cliche, but summertime, there's no better place. place on earth than Wrigley Field.

Amen. And whether, yeah, there you go. Go Cubs. I'm still a little bitter that the socks beat them, but whether they're good or bad, it's just an incredible environment to go catch a game, even to see a concert there. So I'll say that. And was that weird due sidebar, like that that became such a high luxury real estate market right around Wrigleyville?

Like back in the day, like, why would you want to live next to the stadium? Oh, my gosh. Drunks and all that. Yeah. I remember my dad because, you know, they had the dry cleaners on Broadway and Cornelia. And my dad would tell me, like, especially in the 80s, he's like, there's only two reasons why you'd be on the corner of Clark and Addison. It'd be there because you're going to the Cubs game or you're trying to buy crack. It was just like, it was just a shanty little neighborhood.

And now it's like. So if I see you there and you're not going to a Cubs game, you're in trouble. Exactly. That was his message. That was his message. Don't, don't be there without Cubs tickets. one of my other favorite things, you know, I'll do this by season.

In the wintertime, during the holidays, going to the museum and science of industry, they do this like Christmas trees from around the world exhibit every year. For like a hundred years they've done. Yeah, yeah. And some of the trees are cheesy, how they're like, you know, decorated.

That's the most like stereotypical stuff from the country. But it's just a cool thing. I think part of me as a kid, I would go there to see like this. Korea tree. And so, you know, they're still in the solgia in it. I still do it with my family. So I still love doing that. I always recommend people do that. Springtime, going to Jackson Park and seeing the cherry blossoms. A lot of people don't realize that we have a lot of cherry blossoms. And you have like a seven-day window to do it. But if you can catch it, I think it's super beautiful to do.

I was just with a guy out of a golf tournament We were having a theological, philosophical debate Of if God had it to do over again He would have made things like cherry blossom's bloom For like maybe four months Right, right? Like seven days is too short Like all these, especially in Chicago

Like come on, stretch it out I feel the same way about tulips. I'm like, you know, they come up And then they go And you're just like, man, why couldn't these be just around? Long Kirkland. This guy's counter was if it went away, didn't go away as quickly. We wouldn't appreciate it as much.

Yeah, that's true. That's true. I like that mindset. And the last piece I'll add in, I feel like these are all touristy things to do, but this is why I love the city. Like, these are things that I do still. Once a year, we'll go on an architectural boat tour. And I think it's one of the greatest ways to see the city. It's just a great time to be out and about. And I always learn something new that I didn't know. And I think it's a fun thing to do. So I say those four things are my go-toes. But I used to raise sailboats. I used to work, like cleaning the boat in Montrose Harbor down there.

Yeah, not Montrose, on down south by McCormick Place, whatever that. Oh, yeah, yeah, yeah, yeah. So one of the boats where I must have been an extended tour, and they would come into there, and the tour got to be like, this is an America's Cup boat. It won the America's, I'm like, no, none of that's true. That's hilarious. And I'm the one that goes back. Did you know the America Cups?

Yeah, there's one of the boats right over there. Another good hack. You can take the water taxi from the aquarium to Navy Pier. It goes out in the lake there. You get basically a $7 boat charter. See the skyline from that angle is always one I like to give people. Yeah, that's a good one. And another hack will throw out here.

Then we're going to go to the aquarium at night. this don't get arrested or don't tell them you got it from the podcast every day. You go there and now you walk around the back and you can go right up to the window, right? There's a side of like they have to climb through some bushes, but you're right up in the window and the dolphins are just playing in there.

There's no fans, there's no, like, they're not jumping through stuff, but they're pushing balls around and they're doing their thing. Super cool. That's a pro tip. You know what's funny is that you say that because when I'm like from the other side, like coming from Soldier Field, you always see that ledge that hugs that glass and you're always wondered.

like, there's got to be a way to get there. Maybe not after a Bears game because the cops are on alert. That's true. Okay. I like that. Awesome, Tommy. We'll leave it there. We'll put, for all you listeners who want to buy some, take a, well, I guess they'd be

making a deposit with you. You're going to do a draw. We'll put your info down in the show notes, but thanks again. Thanks for having me. I look forward to seeing you shortly, hopefully on a boat or at a Cubs game. We'll see. Or we got to grab a burger. done.

There you are. I think I'm going to choose root stack. Root stack. Yeah, let's do it. I'm down. Root stock. I'll be at root stack. You'll be at Rootstock.

Awesome. Thanks, Tommy. All right, man. Thanks for having me. Okay, that's it for the podcast. Thanks to Tommy for coming on. Thanks to Jeff Berger for producing. Thanks to RCM for sponsoring.

We'll be coming back with some more Chicago month next week. Talking to two folks from one of Chicago's famed exchanges. The Sebo. We'll see you then. Peace. You've been listening to The Deriviviviviv. Links from this episode will be in the episode description of this channel. Follow us on Twitter at RCMaltz and visit our website to read our blog or subscribe to our newsletter at RCMaltz.com.

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