The Real Finds Podcast, Episode 108: Jon Siegel of RailField Partners
Gordon Lamphere, J.D., of Van Vlissingen and Co. sits down with Jon Siegel, Co-Founder and Chief Investment Officer of RailField Partners, to discuss the frozen multifamily market, the workforce housing opportunity, and the discipline it takes to close deals in 2026. This transcript has been lightly edited for clarity.
Jon Siegel (00:00): These syndicators, what they would do is they would buy the property, and they had a playbook. And the playbook was: we buy an older property, we fix up the kitchen, we spend $8,000 fixing up a kitchen, and then we raise the rent by $200 or $300. And the NOI goes up by 30 or 40 percent. Pretty easy math. And you have this low-rate financing on it, and the market’s really hot, so you can sell the thing at a three-and-a-half cap when you’re done. That makes everybody look like a genius. There are still people that are waiting for things to go back to the way they were in 2021. And spoiler alert: they’re not going back that way.
Gordon Lamphere (00:35): What are we not talking enough about in real estate right now?
Jon Siegel (00:38): What we’re probably not talking enough about is…
Gordon Lamphere (00:48): Today, most multifamily investors are chasing new, low-risk product. Jon Siegel, CIO and co-founder of RailField, thinks that’s exactly why workforce housing is wide open. He came from Fannie Mae, buys institutional multifamily, and has strong opinions on where the herd gets it wrong. If you’re ready for a conversation about where opportunity actually exists in 2026 and 2027, I think today’s episode is well worth a listen. Hey Jon, thank you so much for hopping on the podcast today.
Jon Siegel (01:25): Thanks for having me. Appreciate it.
Gordon Lamphere (01:27): Before we start: why real estate?
Jon Siegel (01:32): Good question. When I was in college, I really had no idea what I wanted to do, and I got a job at a radio station when I got out. So I wasn’t exactly on a real estate track. That sounded pretty cool and it was kind of interesting, but you had to get up at five o’clock in the morning and you got paid minimum wage. My parents and my girlfriend at the time were like, “You need to get a real job.” I’m from the D.C. area, and I was back here in the D.C. area, and if you weren’t in government here, real estate was a big business. So I just called people I knew, and some guy at a real estate company said, “We’ll give you a shot.” I kind of fell into it, and here I am now, many decades later. I kept going in real estate.
Gordon Lamphere (02:20): So a few decades later, a lot has changed in real estate, and one of the biggest things that’s changed is financing. How are syndicators, investors, and GPs reevaluating the capital stack and the structure needed to have a great performing fund, asset, or deal in the post-2022, post-2023 higher interest rate world?
Jon Siegel (02:53): Financing has certainly evolved over the years. I worked at Fannie Mae back in the day, and multifamily went from not having that to the agencies being a big source. But leading up to 2021 and 2022, it was definitely symptomatic of the cycle. As cap rates went down, the more traditional financing, what I would call more conservative financing, became not particularly appealing, because you’d never win any deals. And we lost a lot of deals then, because we’d say, “We’re going to put our agency loan on there,” and then we’d get outbid. A broker told me in 2020 or 2021 that 90 percent of deals in multifamily were getting done with bridge loans.
You had a situation where interest rates were basically zero, so the spread on the loan was pretty much the interest rate. You could get a loan at three and a half percent, and they’d give you full proceeds. So we started, I guess you would say, financially engineering deals to make them work, and getting away from best practices of real estate. We don’t need to relitigate it, because I’m sure you’ve talked about it many times and everybody knows what happened afterwards, and how much financing has gone sideways.
Interestingly, I think we’re still working through all of that, and that’s why everything’s so slow. But what’s changed is that I think we’re back to basics. There’s a flood of private capital that’s still out there, but it’s probably smarter now. Lenders are smarter in taking risks, and borrowers are smarter in structuring deals that work. It’s not like the concept of a bridge loan doesn’t exist anymore, or a debt fund loan. There are probably more debt fund loans now than there were then. But they’re structured in a way that protects the lender more, and borrowers learned their lesson to a certain extent. And that’s completely changed the capital stack. It changed not just the debt side, but the equity side too, because most equity investors saw the opportunities in private credit and tried to make their equity more debt-like. So everything’s changed, and as I say, I think we’re still working through it. I’m not sure we’ve landed on the permanent solution yet.
Gordon Lamphere (05:23): We’ve definitely talked about this off the podcast, but I think it’s important for some of our listeners who started tuning in around 2023 or 2024, who were younger, whether syndicators, investors, or brokers. Where do you think some of that trouble is? You mentioned the trouble occurring with bridge loans, and we’re starting to see that play out. I opened up Twitter, or X, this morning, and there was another fund that went down. What are you seeing, where does most of that trouble lie, and why is it clogging up the market now?
Jon Siegel (06:10): I can speak mostly to multifamily, although this probably carries over across asset classes. Office has its own situation, which I know you’re more exposed to. But what happened, basically, was that deals wouldn’t underwrite unless you used more aggressive financing.
Think of the equation. It’s 2021, you want to buy a property, and cap rates are really low because interest rates are really low. And honestly, a lot of people got into the business then, and it was pretty easy. All you had to do to win a deal in 2021 was bid the most. And how would you bid the most? You’d bid the most by getting the most proceeds on your loan. And what could go wrong? You’re paying a four cap, or a three-seventy-five cap, and you’d get a three and a half percent interest rate.
The equation also assumed that if you bought the property, rents were only going in one direction, and that was up. Because of all the money that was in the system with COVID, we saw 20 percent rent increases in some markets. And there was this playbook. These syndicators would buy the property, fix up the kitchen for $8,000, raise the rent by $200 or $300, and the NOI goes up by 30 or 40 percent. Pretty easy math. And with low-rate financing and a hot market, you could sell the thing at a three-and-a-half cap when you were done. That makes everybody look like a genius.
Except two things happened. One, there was too much inflation, so interest rates went up a lot. And at the same time, rents stopped growing. There’s a concept in economics called elasticity of demand. You can only raise rents so much; people can only pay so much. We priced ourselves out of the market. So the value-add proposition isn’t operative anymore, because you can’t raise the rents. And your interest rate: say you had a loan when SOFR, or LIBOR, whatever we were calling it at the time, was five basis points and the spread was 350, so you had a loan at a 3.55 percent rate. Then all of a sudden it went up by 300 basis points, and your loan is at 6.55. That’s a pretty big change in payments. So you can’t make your payment, and you can’t raise the rent. What do you do? You’re stuck.
A lot of people held on, and have held on. It’s hard to believe, but that was four years ago when this all happened. We thought it would work its way through pretty fast. But people can hold on, and lenders don’t really want the properties back. So we’re stuck. These loans had maybe a three-year term. If you took the loan out in 2021, it was due in 2025. But in 2025, if you could come up with a little money to put into the deal, they’d give you an extension. It’s what we call extend and pretend. Because the market’s going to get better, right? We all know the market’s going to get better and rents are going to start going back up. But that hasn’t happened, and interest rates have not come down. We’ve seen some pieces of distress around the country where people just can’t make it work, but a lot of people have held on, and there’s this flood of capital in the market, so people will give them a new loan and they can keep kicking the can down the road.
So that’s the situation we’re in. A lot of these deals don’t work anymore. The main thing to think about from an investor standpoint is the math on the property. There’s the debt, and then there’s equity. When those rates went up and the property couldn’t raise rents anymore, pricing changed. And the property is maybe worth the debt amount. What that means, at the end of the day, is there’s no equity. And who wants to tell all their investors that their investment is zero? Nobody. So they have to hold on for dear life. There’s a saying that time heals all wounds in real estate. If you can hold on long enough, maybe it’ll work itself out. And that’s the situation we’re in now.
Obviously, when we talk about how financing has changed: nobody wants to get in that situation anymore, be it a lender or a borrower. So new loans aren’t as easy to come by. There’s plenty of money out there, but everybody’s trying not to replicate that situation, while they’re also trying to hold on to these other deals. That’s the place where we’re stuck right now in the marketplace.
Gordon Lamphere (11:38): I can’t speak at length to multifamily, because my specialty that touches multifamily is typically the initial transaction, the land sale for development, and we know that world very well. I’d say we’re among the top in our market at performing that. Beyond that, multifamily value-add is not my world, and that’s one of the reasons we have folks like you on the podcast. But in the world of office, industrial, and retail, we’ve definitely seen this play out. It’s something where we’ve been consciously passing on deals over and over again since 2022 and 2023. I’m sure my wife wishes some of our investors didn’t pass, because it would have been nice to have those commission checks. But you sleep a lot better at night knowing the deals you’re involved in, as either a broker or a developer, are actually good deals.
Jon Siegel (12:49): Yeah. And you have the overlay in office of the whole world changing. In multifamily, I always say people always need a place to live. But in office, people stopped going to the office.
Gordon Lamphere (13:00): Hey, you know what? Kids in the place that you live make it hard to do work, so we’ve been okay. But let’s get back into multifamily. Lenders are now being a little more cautious. What is everyone waiting for, and what does a good deal look like in multifamily today?
Jon Siegel (13:28): People are waiting for a couple of things to happen. There are still people, and this goes back to the inexperienced side of the market, who are waiting for things to go back to the way they were in 2021. And spoiler alert: they’re not going back that way. It’s not happening. I would stop waiting, if anybody asks my opinion.
What more savvy investors are waiting on now is probably two things. One would be stability. What we’ve had is a roller coaster of rates going up and down. Not going from 3 percent to 6 percent, but the 10-year Treasury going from, say, 3.90 to 4.50. It’s awfully hard to price a deal in any asset class when the index you’re basing your loan on keeps moving around. You start a deal at 3.95, and all of a sudden it’s at 4.50, the math on the loan doesn’t work anymore, and then the deal doesn’t work anymore. So I think a lot of people are waiting for some sort of stability there. Most people have come to grips with the fact that it’s higher for longer. And it’s not actually that high. It feels high to all of us because we had such low rates, but if you look at a graph of the 10-year over 30 years, it’s really not that high.
Gordon Lamphere (14:58): I will always remember sitting down at lunch with one of our investors, someone from a great family office we’ve been involved with on deals for years, and he said, “It’s not Volcker in the eighties. What are you guys worried about? It’s not that bad.” It’s always relative, right?
Jon Siegel (15:17): I remember when I got into this business, there was an old-school guy here in D.C. who owned a ton of apartments, and he said, “Hey, young guy: if you can find a loan with a seven percent rate, take it all day long.” And now we wouldn’t do a loan at seven percent. It’d be crazy. So yes, it’s all relative.
But the other thing people are waiting on, the more institutional investors and the savvier people, is some sign of real growth you can put your arms around. Our models all include some sort of rent growth, and honestly, there hasn’t been any rent growth. Rents have been going down, and that’s a problem. It’s hard to underwrite. In Austin, Texas, where we own some properties, and which was the hottest market in the country at one point, we are now back at 2019 levels. The rents in Austin are back to where they were in 2019. They went up 40 percent, and they came back down.
If you ask most savvy investors now, they’d say what they’re looking for in a multifamily property is real lease trade-outs: seeing that the rents on the property are actually going up, that the new lease I’m signing today is higher than the lease I signed last year. It doesn’t have to be 10 percent. Just some positive momentum, some kind of income growth you can underwrite. I think that’s what’s keeping a lot of people on the sidelines, or looking for a unicorn. Very few people ever say to me, “We’re not in the market.” They all say, “We’re in the market,” but they’re looking for a unicorn, and if they can’t find the unicorn, they’re not really in the market. What they’re looking for is some sign that we’re starting to head back in the right direction.
Gordon Lamphere (17:20): Does a lot of that come down to the development pipeline? I know from our side of the landscape, it’s so hard to find actually developable land in neighborhoods where people want to live in Chicagoland, or even redevelopment projects, and we’ve worked on those too. We’re currently working on several very large ones. Do you think a lot of that rent growth stagnation is the market effectively adding new product in most markets? And are there markets you’re targeting that might not be as rent-growth negative because of contracting supply factors?
Jon Siegel (18:04): Sure. If you were to talk to most people in multifamily, they’d say the reason there’s no rent growth, the reason rents went down, is oversupply. It’s an interesting dynamic, because first of all, it’s very market-specific. And secondly, it’s an interesting world we live in, because we have an amazing shortage of affordable housing in America. There are lots of people who can’t afford to rent an apartment, or there just aren’t enough apartments for those people. But all the new development is at the high end, and most of that new development was in the hot markets, the Austins of the world.
There’s new development everywhere, but especially among institutional investors, there’s a bit of a herd mentality, and everybody wants to be in the same markets. So you’re a hundred percent right that rents have gone down in a lot of those markets because of oversupply. Interestingly, we’d been saying there’s a cliff of supply coming and it’s going to fall off, but that seems to have been recalibrated. It’s not going to be a cliff; it’s just going to start to stabilize. But oversupply has definitely been one of the main reasons we haven’t seen rent growth.
I’ll give you an example. There’s a family we do a lot of work with. We own or manage all of their multifamily. They like to invest in multifamily, they’re long-term owners, and they like cash flow. Some of them are eighty years old and they want their check every month. We have a lot of properties we bought for them in Sun Belt markets over the years, and they’ve done fine. Typically, the game plan when we sold a property was a 1031 exchange for tax purposes, and we’d buy a new property with the proceeds.
We sold a property in the Raleigh market in North Carolina, which was, and still is, a really good market. But it had oversupply, so there’s just not a lot of rent growth there. They said, okay, we want to redeploy the capital. So we started looking in the same places we’d been buying before: Raleigh, Charleston, Dallas-Fort Worth, these markets that had a lot of construction. And the value proposition everybody gives you there is that you can buy the property at a great basis, maybe even below replacement cost. We talked about how value-add properties didn’t go up in value. The same thing happened for development. Those pro formas didn’t come together, and people are willing to sell at a pretty attractive price.
But that doesn’t work for somebody who wants cash flow, because there is no cash flow. You’re getting it at a good price, and you think you’ll be able to sell it at a high price in the future, but you’re trading away cash flow for a couple of years. So we pivoted and looked at other markets, in the Midwest, and we ended up buying them a property in Indianapolis. It was a new-construction property, and there is some new construction there, but a lot less. The rent goes up every year, and there’s cash flow. That is a hundred percent the way a lot of people are looking at it now: there are markets with less construction where rents are still going up. Not 20 percent. Maybe one or two percent a year, but they’re going up. Those are appealing markets. But a lot of institutional investors still won’t go to those markets, because they don’t believe there’s long-term growth there.
Gordon Lamphere (21:48): I find that dichotomy fascinating. For us in Chicagoland, there are so many elements of political risk that make certain submarkets toxic, but at the same time, rent growth continues because there hasn’t been development. It’s a fascinating dichotomy, and it’s something we regularly talk about in our market reports.
Speaking of reports, one of the things I think you can report on better than many of the folks we’ve had on the podcast is what’s going on with affordable and workforce housing: how that’s played out in the last couple of years, and where you see potential opportunity. It’s such a core portion of the American housing story. I’d be fascinated to hear where you think some of that opportunity exists.
Jon Siegel (22:49): I think there is a lot of opportunity there, and we’re very bullish on workforce housing. Though I should say, one of the sayings I have with our guys is, “With Jon’s billion dollars, I would buy this deal. But Jon doesn’t have a billion dollars, so Jon has to find an investor to do it.”
As we said before, there’s an incredible shortage of affordable housing in America, and those people are not going to live in brand-new construction, unless it’s maybe a tax credit property, and there’s not enough of that. Unlike an office building, which can become obsolete because people don’t want to go to the office and only want the high-end buildings, people need a place to live. As I always say, you can’t live in a computer. You have to actually live in an apartment. So there’s a huge need for these apartments, and they stay full.
But interestingly, most investors, especially institutional investors, don’t want to get involved in older properties. If you talk to a lot of brokers in the multifamily space, they’ll say if they have a newer property, ten years old or newer, the market’s slow, but there’s a pretty long bid list on those deals. The Blackstones of the world are all chasing that stuff. You’re never going to get fired for buying a new property in a hot market. But you can probably make more money on the older stuff, and they won’t touch it. On the newer deals there’s a long bid list, and you can’t give away a property that was built in the seventies or eighties in a lot of markets. That means the pricing changes on those, and the cap rates go up.
We recently bought a seventies-vintage property here in the D.C. area, in a submarket with high costs and not a lot of new development. The property is 95 percent occupied, and you can continue to raise the rents. But there’s not a great capital market for it right now. Two things happened. Equity investors were very nervous about a seventies deal. Most of them didn’t want to touch it; it was an instant no. “We don’t want anything that old.” And a lot of the lenders were the same. The agencies will generally finance it, but they’ll be pretty conservative, and other executions will say no, it’s too old.
So as we talk about dichotomies, it’s an interesting one, because I think there’s a lot of opportunity there. Obviously everybody would love to find a deal where you buy for pennies on the dollar and sell for dollars on the dollar and make a fortune, but there aren’t many of those deals out there. If you’re investing wisely, slow and steady, doing good real estate deals: buying a 95 percent occupied multifamily property in a strong area, without a lot of new development, with a whole bunch of demand, where you can raise the rents two or three percent every year, that’s a pretty good deal, and you can usually buy those at a pretty high cap rate. But it’s hard to find the money for those right now. The opportunity is there. The ability to execute on it, for a lot of people, is much harder than it probably should be.
Gordon Lamphere (26:27): So let’s talk about executing on some of those deals. Is there a certain type of older vintage product for workforce or affordable housing that particularly scares you? Is it asbestos? What’s the red flag, or the list of red flags, that terrifies you on a potential value-add?
Jon Siegel (26:52): You can always talk yourself out of any deal, I guess. But yes, there are certain types of construction we’d stay away from. There was a company called Cardinal back in the old days that built one-story apartments you see all over America, built in the seventies and eighties. Those, we know, fail. I wouldn’t touch one. There are certain design elements, where sometimes the guys here will say, “We found this deal,” and they’ll show me the picture, and I’ll say, “Nope, we’re out on that.” They’ll ask why, and I’ll say, “Just look at the picture. We’re out.” And there are certain other types of construction that are functionally obsolete that you don’t want to get involved with.
But mostly, if you do your homework: there are old systems you don’t want to get involved with, big boilers and things like that, unless you really know what you’re doing. Apartments aren’t really super complicated, and as long as you do your due diligence and have the right team that can quantify things, you can usually price them out. The physical side you have to be careful with, but a lot of it is location-driven right now. If you have older stuff that’s infill and there’s demand, that works. One of the things we always talk about is that markets are important, but submarkets are even more important.
And what makes a good submarket is not just being in, say, your neighborhood, Wilmette, the most affluent area. It doesn’t have to be a super wealthy area, but is there some sort of demand driver? Is it near jobs? Apartments are driven by jobs a lot. Is it near a school, a hospital, something like that? Is there a reason for people to live there? We have a lot of properties in Texas, and I always joke that your apartment in Texas has a balcony that overlooks where they’re going to build the next apartment in Texas. And the highway exit where you get on to drive an hour to your job. It’s hard to make those work if you don’t have the newest, nicest property, because why would anybody live in an older place unless it’s just the cheapest?
So it needs to be in a location that has some sort of demand driver, some reason for people to live there. You see a lot of these older, distressed deals in markets like San Antonio, in what I’d call apartment city: fifteen properties built in the eighties, all right next to each other, next to a highway, where you have to drive an hour to work. What’s the value proposition there? That’s what really scares me on a lot of those deals.
Gordon Lamphere (29:38): We’ve talked about some scary factors and some opportunity for institutional and entrepreneurial owners. Is there a certain opportunity that exists right now that you’d be head over heels interested in, for either of those asset classes? Or does it just take discipline in this market?
Jon Siegel (30:07): I’ve been on podcasts and at conferences where people ask, “What’s the secret to getting a deal done right now?” I think you nailed it in saying it’s really more discipline. It’s not, “I’m only going to buy properties built in 1993 located two miles from a Chick-fil-A.”
Gordon Lamphere (30:33): Hey, Chick-fil-A is pretty good.
Jon Siegel (30:37): Except on Sunday. But sometimes you might outsmart yourself doing that. I think it’s really just being disciplined and finding assets that make sense. As I say, I think there are a lot more assets that make sense than I can sometimes convince other people make sense. And it’s discipline not just in the identification, but in the execution. A lot of it is on the deal-making side now, because it was easy back in the good old days of a couple of years ago. “They’ll pay twenty-five? Okay, I’ll give you twenty-five too,” and you could win. Now, first of all, it has to make sense because you have to be able to finance it. And secondly, you want to do a deal where you’re protecting your backside.
Every deal right now seems to have the same story in multifamily, especially if you’re looking at workforce housing. They say, “The guy bought it for thirty million, so he’ll sell it for thirty million. He has a loan of twenty-five million.” You underwrite the deal, and you call them back and say, “I don’t understand how you get to thirty million.” Well, they just want thirty million because they want to give back all the equity. They don’t want to have a loser. And you say, “Okay, but the loan is twenty-five million and the property’s worth about twenty-three.” And they say, “Yeah, we know.” Then they call you back two months later and say, “Can you get to twenty-five million?” so they can pay off the loan without coming out of pocket. And you say, “In the last two months, occupancy went down a little, and it’s probably worth twenty-two now.”
So how do you make that deal work? I understand the seller not wanting to sell, and no buyer is just going to say, “Sure, I’ll give you thirty million.” I say that most sellers these days have to go through the seven stages of grief and get to acceptance, accepting what their situation is. You have to wait for that. They’re not just going to take the price immediately. You have to go through a bit of a process. But sticking to your guns, and then when you do the deal, saying, “Look, it’s only worth this amount, this is the most we can do, but we’ll do it and we’ll actually close.” I think that’s how you get things done these days.
Gordon Lamphere (33:06): I don’t think that’s too different from the world of industrial and retail. There are several deals we’ve worked on, both on and off market, that started with other brokers who were blowing smoke, telling owners a property was worth a lot more than it was because they purchased it between 2020 and 2022. We got those opportunities and helped them out, sometimes as the second or third broker to look at it. Sometimes a property isn’t worth what you paid for it. That’s a sad statement, and I don’t mind telling people that, but we probably only get about a third of the listings we could because we tell people what a property is actually worth.
Jon Siegel (34:01): Right. But you actually have credibility, and at the end of the day, that actually means something.
Gordon Lamphere (34:06): One of the things that’s had a lot of worth on this podcast has been our Final Four. Bringing some of the top folks in the industry on, we find these four questions really help give our listeners a different perspective and educate them about what’s actually happening in the market. One of my favorites: what are we not talking enough about in real estate right now?
Jon Siegel (34:35): This is probably more multifamily-centric than anything else, but what we’re probably not talking enough about is regulatory issues, and where the tide is in politics right now. As an industry, we’re really bad at regulating ourselves. As much as we might have good intentions, and we’re good people, we’re not dishonest, we’re not good at regulating ourselves. If money’s cheap or deals are easy, we’ll do another deal and raise the rents another 20 percent. That got away from us.
You don’t have to watch a lot of news to see what’s going on in politics around the country. Here where I am, we’ve had a couple of jurisdictions impose rent control over the last couple of years, and it’s made the market really hard. We hear about rent freezes in New York, and the whole thing about algorithmic pricing, where people are worried these systems we all use to set rents are anticompetitive. I’d argue they’re probably not. But you have to listen to what the world is saying. Not only is it the right thing to do, but for our business, you’re going to get crushed if you don’t pay attention to it. Right now, the image of the big evil landlord is alive and well. Most of us are pretty nice people, but we don’t make a very good soundbite saying we want to come to your market and raise rents. So that’s the topic. It’s boring, but it’s the one we probably need to talk about more.
Gordon Lamphere (36:26): I think that’s a huge topic. I was out with some friends a couple of weeks ago, and they found out we do a lot of landlord rep work, a lot of listing work. And I’m not even someone who sells active multifamily; we sell land sites and development sites, but we don’t do many multifamily transactions because it’s a different world. And this friend of a friend said, “I don’t want to talk to that guy, because he’s with the landlords.” And I said, “Well, my work is predominantly industrial and office, so if you take the corporate world, I’m negotiating against corporations on behalf of clients as well.” But that sentiment really exists in the world, and it’s a huge political risk for the multifamily portion of our industry.
Jon Siegel (37:21): Yeah. I have a nephew who has an MBA and works for a very large corporation, and we were talking once, and he started in about landlords. He said, “The idea of people paying somebody to live in a place, it just doesn’t seem right to me, and these landlords take advantage.” And I said, “Do you understand what I do for a living? And I’m supposed to be paying for lunch here?”
Gordon Lamphere (37:44): So, one of the things that’s really paid for lunch for us over the last fifty-plus episodes is a question I love to ask: ten years from now, what do you think will have changed the most about commercial real estate?
Jon Siegel (38:02): This is probably a pretty cliche answer. You asked what we don’t talk about enough; what we talk about too much is probably AI. Everybody: AI, AI, AI. So maybe I won’t use the term AI, but I’ll use technology, broadly speaking.
I went to a conference put on by an investor we have a big joint venture with, and they had an expert in technology who went through different periods of time where things changed in real estate. Starting in the late 1800s: elevators. The invention of the elevator changed real estate to the point where you used to have two-story buildings, and now you can have a forty-story building. Nobody realized it at the time, but it completely changed real estate. Then you can wind through a lot of different things, like the car, and how the car changed real estate to where everything’s now suburban and drive-oriented.
I think we’re at a point where a lot of that is going to change again. The technology is there for self-driving cars, automation in industrial, robotics, things like that. We talk about it all the time. Everybody says, “I want to use AI in my business,” and what does that mean? It means I put my memo through ChatGPT, because we don’t really know what to do with it yet. But as we’re going through our day-to-day lives, a lot of this stuff is changing. Will we need parking garages anymore? Will warehouses need the same layout they have now? I think all of that is going to change commercial real estate significantly over the next ten years, to where the world is just going to be a little different. We’re going to change from our suburban lifestyle to some other kind of lifestyle. I’m old now, so I’ll probably be retiring by then, but it’s all going to change.
Gordon Lamphere (40:11): I think there’s a lot of change coming, and a lot of change isn’t always as big-idea as you’d think. One of the biggest things: we took over management of a property, and the previous landlord’s agent had done a tremendous amount of work developing paper trails and data. But they hadn’t digitized it and then used that data to find where they were overspending. We were able to find almost a quarter per square foot per year in savings just by putting it through some of the algorithms we’ve developed to cut costs. There’s a lot of that that’s going to go on in our industry. It’s not flashy, but if you have an industrial property and you go from paying two dollars a square foot to a dollar seventy-five, that’s the difference between a deal and not a deal.
In terms of what goes on with this podcast, one of the things that’s been particularly useful for some of our younger listeners, and they’re a large portion of the audience, is a question I love to ask: if you could go back in time and give yourself one minute of advice, what would it be?
Jon Siegel (41:46): Don’t get into real estate. No, I’m just kidding. Real estate has been a great career for me. I would say the thing young me would have benefited most from is hearing the two things that make for success. In my career I’ve gone from working at big companies, to being a principal, to being an entrepreneur. I’ve gone from the principal side to the lender side and back to the principal side. So I’ve been through all the different phases of where you could go.
The two things you need to be successful, and I probably didn’t have much of either when I was younger: one is patience. If you’re in the AI business, or you work at SpaceX, you probably don’t need a lot of patience, because it changes so fast. But real estate tends to be a get-rich-slow business, despite a lot of the hype around it. You need patience in both the business and your career, because good things will come, but they may not come tomorrow. They may come in a year or two.
And related to that: persistence. The people that are best at getting a deal done, and best at starting their own businesses, are people who are persistent. They don’t quit easily. Having a short attention span and not being very patient was probably not my strong suit back in the day. But I’ve noticed now, being one of the owners and a co-founder of my business, that persistence matters. You’re going to have days and months and years that aren’t so great, but if you stick through it, all of a sudden you wake up and say, “Wow, that actually worked.”
And it applies to the task level too, especially as a deal guy. We just closed a deal that we started around the end of last year. Most multifamily deals are 60-day deals: due diligence, loan, close. Every deal now is impossible; everything takes forever. Something came up two weeks before closing that changed everything. It seemed like a minor thing at the time, and it ended up changing everything. We could have bailed on the deal, and I said, “This is a pretty good deal. We shouldn’t bail. We’ll figure it out.” It took us probably forty-five days to figure it out, and we got it closed. At the end, the seller said, “Thank you for sticking with us and not walking, because you could have walked.” That’s maybe a microcosm, but persistence is the trait you see in people who are successful in this business.
Gordon Lamphere (44:42): That’s definitely up there among the characteristics of people who make it. Particularly patience. I’m always trying to teach my little boys patience, and I’ve tried to get them into fishing, which has been somewhat successful at this point. Just sitting there watching your line, sometimes for hours. If I could impart one thing, that would be very useful.
In terms of things I fish for on this podcast, I particularly love this last question, and it’s kind of the whole reason for the podcast. We wanted to know, from the men and women in the arena, who the best people are to talk to. So I’m curious: who’s the next person we should have on the podcast?
Jon Siegel (45:33): That’s a good question. Going back to what I was saying about the topic we’re not talking about enough: I think it would be interesting, and you may lose a lot of subscribers, but somebody who’s knowledgeable about the policy side of things. Who would be the most interesting person? Someone like Mayor Mamdani, to hear: why do you believe a rent freeze is a good idea?
Gordon Lamphere (46:06): I’ll say this: we’ve tried. Not him specifically, but we’ve tried to get people from both sides, and both sides don’t want to come on. The free-market side says, “You’re just trying to make us look bad,” and the side on the left says, “You’re just trying to make us look bad too.” And I’m like, no, I just want to have a conversation.
Jon Siegel (46:29): Yeah, that’s what I mean. I think it would be fascinating. There are some people, like at the National Multifamily Housing Council, which is our big trade group. The woman who runs that is a policy person, and she tries to play it straight. She’s very interesting to hear talk about the issues out there in policy and why they’re important. Yes, it sounds boring, but it’s really important. There are a lot of fascinating people who can tell you great deal stories, and I can give you some names there too. But if we talk about the issues that are really facing our industry now, I think that would be different.
Gordon Lamphere (47:10): We’d love any off-the-podcast connections on that, because that’s something we’ve struggled with. We’ve gotten a lot of big names, but we haven’t been able to get anybody who wants to talk about that. There’s one last thing: if somebody wants to reach out to you, what’s the best way to get in contact?
Jon Siegel (47:34): Probably the best way to reach me is to send me an email: [email protected]. My company is called RailField. I’m also on LinkedIn, though you’d be surprised how many Jon Siegels there are in the world. Just send me an email; that’s the easiest way to get a hold of me. I’m a big believer in giving back to everybody, because I know from being younger in the business that so many people blow you off. If you send me a message and it’s real, I’ll get back to you. I always love connecting with people, meeting new people, building a network, and, in my older age now, talking to younger people and trying to pay it back a little bit.
Gordon Lamphere (48:26): It’s always great to pay it back. Jon, thank you very much. We really appreciate having you on, and we’ll have to have you on again in the future.
Jon Siegel (48:33): Great. Thanks a lot for having me.
Gordon Lamphere (48:35): Thanks again to Jon. We appreciate his insights. And if you enjoyed the podcast, please give us a like, a five-star rating, and a review. Your comments, interactions, and subscriptions truly matter and help us get quality guests. You can find us on YouTube, Spotify, or wherever you do your podcasts. I’m Gordon Lamphere, this is The Real Finds Podcast from Van Vlissingen and Co., and thank you for listening.
Van Vlissingen and Co. has been the Midwest’s oldest commercial real estate brokerage, development, and management firm since 1879, and today is independently ranked the #1 commercial real estate agency in Chicagoland, home to the #1 independently ranked agent, Gordon Lamphere, and the region’s #1 ranked commercial property management team. If you own, manage, or invest in energy-adjacent, mixed-use, or transit-oriented property across Lake County, the North Shore, the Northwest and O’Hare corridors, DuPage and the I-88 corridor, Will County, or southern Wisconsin’s Pleasant Prairie, Kenosha, and Racine markets, contact Van Vlissingen and Co. at 📞 847-634-2300 or 🌐 vvco.com. For a market-wide view of where these dynamics sit today, see our State of the Chicagoland Commercial Real Estate Market for Q2 2026.