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Jeremy Yost
My dad was very well known in the entrepreneur space and I didn't want to just be known as Dan yo son. I wanted to develop my own identity and I was able to do that and persevere through that and become my own man.
Narrator/Host Introduction
However, Jeremy Yost is a real estate entrepreneur, CEO of Yost Management Services and co founder of Innovative Development Partners. He helps create thriving multifamily communities through strategic property management, development and a commitment to delivering long term value for residents, investors and neighborhoods.
Jeremy Yost
And if you think you're going to fail, you're going to fail. So every deal that I do or look at, if I'm going to pull the trigger, I'm going to execute it. I'm going to execute it very well.
Ray Gutierrez
Yes, sir.
Jeremy Yost
And I'm going to see it through whatever that might be, I find a way to get it done. You control your destiny. The sky's the limit. So you can start something and end up at the top of the food chain all by hard work. Because you know, grit beats anything. And it spans the globe like a super highest cold Internet Elvis.
Guest/Additional Commentator
Today, Apple is going to reinvent the phone. It's not over until I win the
Jeremy Yost
Living your Legacy podcast. For those who live to leave a legacy that's extraordinary.
Guest/Additional Commentator
The impossible has been. Oh, that is sensational. Jordan, Open Chicago with the lead. You said Paul is the fastest man on the planet. You can live your dream.
Ray Gutierrez
Welcome back to another episode of the Living youg Legacy podcast. For Inside Success, I am Ray Gutierrez. Joining us right off his episode filming of operations CEO is Jeremy Jost. Jeremy, you came from a bizarre location that's far weirder than Miami. But somehow you are here.
Jeremy Yost
I'm here. I traveled from the land of Illinois and cornfield and soybeans and happy to be here.
Ray Gutierrez
Right on. Sand, soybeans. Sand, soybeans.
Guest/Additional Commentator
Cool.
Ray Gutierrez
All right. What brings you out here, my friend?
Jeremy Yost
So I'm here because of Inside Success. Operation CEO came down did an episode earlier this morning and the filming went great. The team was absolutely phenomenal.
Ray Gutierrez
Cool, cool. I'm glad that we did not disappoint. And now you're sitting in a podcast with a man in the skirt.
Jeremy Yost
Rock and roll, baby. I love it. Cool.
Ray Gutierrez
I'm glad you're into it, dude. Yeah, we like to celebrate here and influen our guests and colleagues. What are we going to learn about you in your episode, my friend?
Jeremy Yost
So a little bit of my background and 17 years of real estate development and management. A second generation entrepreneur in the real estate space. And so learn A little bit about my upbringing from a small town of Charleston, Illinois.
Ray Gutierrez
Cool.
Jeremy Yost
And navigating the field of real estate development, where life is essentially a roller coaster. There's tons of ups and downs when the ups are up and the downs are down, and you just find a way to persevere through it.
Ray Gutierrez
You mentioned legacy. Your dad was supposed to join us today. This was supposed to be a dual interview, as we like to call it here. What gives?
Jeremy Yost
So, you know, my dad's 82, he lives up in the Villages, Florida, so he is a Floridian, but just some health issues and just unable to travel.
Ray Gutierrez
Well, I apologize for being such a jerk about it.
Jeremy Yost
Oh, absolutely. Now you're fine, you're fine. No, he just. Just wanted to kind of relax and just as he should, as he should at his age and wished everyone the best and just said I could handle it.
Ray Gutierrez
Very cool. What's that like having that amazing knowledge then passed down to you and now you are in the year 2026 and it's just like, holy moly. Everything that my dad passed on to me is out the books or is it completely relevant?
Jeremy Yost
You know, it's a little bit of both, sure. To a certain extent, growing up, I felt like I had trouble with, like, identity in the sense of I didn't want to just be known as Dan yo son for where we were at because, you know, smaller town. But my dad was very well known in the entrepreneur space and I wanted to develop my own identity. And, you know, I was able to do that and persevere through that and become my own man to where something that my dad was proud of me and pivot. However, I say all that to say I wouldn't be where I'm at today for sure if I didn't have such an amazing mentor in him. Because, you know, I'm 39 years old. Most people my age aren't out developing real estate across the Midwest or the United States without a little bit of help. And I wouldn't be where I'm at without the guidance that he gave me.
Ray Gutierrez
Oh yeah.
Jeremy Yost
And so I feel like I have a little competitive advantage because growing up in an entrepreneurial family, what most people think is crazy, I think is normal. Normal.
Ray Gutierrez
Oh, absolutely. Yeah. Yeah, it's crazy. It's crazy that you mentioned that. Haha. No, it's. It's absolutely true because being in an entrepreneurial like tribe, that that family kinetic energy is very different. And it's interesting because you and I have the similar age. I'm 42 and for the last five years, I've been looking for like a mentor. I didn't. A mentor. And I just can't call up my, my dad because I don't have one. But it's not about that. That's a different podcast. It's tough. It's tough having like this big vision and, and a lot of it is fear. It's just like, how do I just jump in and plunge into this crazy idea? I need, I need that one person to encourage me. Or when I fail to say, great, you fail. Fail harder. Let's pick you back up so you can ascend. How difficult is that to do with and without that, that third party voice that's helping you move along.
Jeremy Yost
You know, essentially, I feel this ties into anywhere in entrepreneurship.
Ray Gutierrez
Absolutely.
Jeremy Yost
You have to believe in yourself. And it comes to a point where if you think you're going to fail, you're going to fail.
Ray Gutierrez
Oh, yeah.
Jeremy Yost
At the end of the day, no matter what, you have to believe in yourself. So every deal that I do or look at, and if I'm going to pull the trigger, I'm going to execute it. I'm going to execute very well.
Ray Gutierrez
Yes, sir.
Jeremy Yost
And I'm going to see it through. I never think of what could happen because if I do, then that I could fail for sure and then I just wouldn't do it. So when I pull that trigger, I'm balls to the wall, 110% all in. And make sure that the project gets done right on. Whether it's an apartment complex or an assisted living or a hotel, whatever that, whatever that might be. I find a way to get it done right on.
Ray Gutierrez
Oh, let me give you that proper info, Jeremy. It says you're the CEO of Innovative Development Partners and Yoast Management Services.
Guest/Additional Commentator
Yes.
Ray Gutierrez
Amazing. What are those things then? What are those things?
Jeremy Yost
IDP is. It is our development company.
Ray Gutierrez
Is that your R2 or my R2?
Jeremy Yost
It's my R2.
Ray Gutierrez
God damn it, R2. Shut up. I've got all. No, I can clear this out. That's an R4. I can clearly tell by that. Sure, that's definitely an R4.
Jeremy Yost
Probably one of my kids.
Ray Gutierrez
Oh.
Jeremy Yost
So Innovative Partners is holding company where we develop real estate.
Ray Gutierrez
Cool.
Jeremy Yost
And Yoast Management Services Inc. Is my property management entity. So I've got a development component and a management component. And our development side, we've been very, very blessed to develop all over Illinois. And now we are expanding into Indiana, Florida, looking at Missouri and Kansas.
Guest/Additional Commentator
Cool.
Jeremy Yost
And hopefully go nationwide. But, you know, growth takes a Little bit of time. And we've been in a business of capital raising, starting to raise capital for some deals and trying to tie in and using other people's money to continue expansion.
Ray Gutierrez
Yes, it's called network marketing, essentially.
Jeremy Yost
Yeah.
Ray Gutierrez
Which is brilliant because I actually, a couple of weeks ago, I had a guest here that create. Created his program, eye level to high level. And I'm looking, I'm building capital because I do have property. And what you're basically describing to me is like, I'm curious if I'm your perfect client, because you said property development, where my, my house is quite old and it needs to be, you know, the windows are not updated, the roof needs to be updated. And I know I qualify for all these grants, especially as a Floridian and a homeowner and legacy of the couture is. But I also need the property management side because once the house is up and atom like I want to do not I don't want to sell it, but I definitely want it to be an experience where I can Airbnb it or, or, you know, a bed and production breakfast place where, you know, you can fly in, shoot your content, you know, have breakfast, not even interfere with anyone in Miami. Because my house is right next to the airport. So it's like a pre. Location. And I'm like, looking for folks that have the imagination to go, oh, dude, yeah, for sure. We can make this generate wealth for you, no problem. So is that kind of like your, your, your clientele or did I just go off on a complete tangent?
Jeremy Yost
No, essentially, I mean, you know, when you look at property management, all your mortgages, all your properties that you have, you're not paying it. It's your tenants. Yep. So I look at property management maybe a little different than some people, but I look at it, it's more not just about operations, it's about retention and your tenants. So if their overall experience is really good and you have a solid maintenance team with a good manager, it's going to go a long way because the longer those tenants stay, they're going to continue paying their rent, they're going to be happy, and your asset is getting paid for from other people's money. So firmly believe that the tenant relationships with your team members are so crucial because you want them to have a good experience and you want them to stay. Now, obviously, every landlord is going to have issues time to time, you're going to get people that don't pay, then they can't stay.
Ray Gutierrez
Yeah, yeah, of course. What do you Recommend? Full rentals, 6 months, leases, Airbnb. I'm a property owner. What do I do?
Jeremy Yost
So I'm a big multifamily guy. So I believe in, you know, full 12 month lease.
Ray Gutierrez
Nice.
Jeremy Yost
Give me a multifamily asset. Because, you know, through and throughout you look through the last 30, 40 years, multifamily real estate really doesn't feel there's obviously going to be some tough times that happens. You go Back to like 2008. However, I believe, you know, we're, we're not there yet, but there's a crisis. Rents are on the rise and that's because there's not enough supply out there. And without, without new supply coming into markets, rents are going to continue to go up in a hostile environment. And with inflation, it's, it's not been good. So I think during crazier times where things are a little more chaotic is the right time to buy. Because you're going to get in there, you're going to find some better deals and if you come in with a little more capital, you're not going to be in a negative standpoint where a lot of operators have been recently. You're seeing some foreclosures, deals going into receivership with banks. And if you just come in a little stronger on the equity position, you're going to be ahead of the game because the market's in a shift. And I really feel like we're in a good position in the renter space where more people nowadays, they're renting more than buying homes. Where, you know, 20 years ago, the average age for first time home buyer was like 27, 28.
Guest/Additional Commentator
Wow.
Jeremy Yost
And now the average age for first time home buyer in 2025 is like 42.
Ray Gutierrez
I was gonna say it's in 42. Yeah, yeah, that's in the 40s. Yeah, I follow that subreddit and everyone's just like crying their eyes out. It's like, I can't buy a home. I'm like, yeah, dude, you start climbing. Unless you're like some random amazing engineer sitting in San Francisco with your like, your deck like, like chair and you're like looking out. Actually, that's everyone here in Brickle because it's all that crypto money, but you know, good old Miami. But it's like, yeah, like you, what is it like to, to invest into a city like Miami, which is dramatically different where you come from with soybeans versus sand. Miami's so transient. So like every other week it's different versus where you come from.
Jeremy Yost
Right? So we're just getting into some metropolitan markets, the Chicagoland suburbs, and getting in there. It's completely different than the rural areas. So primarily we've focused in rural tertiary markets. Cool. In communities that are like 2500 to 5500 people, where there isn't a lot of, you know, workforce housing or multi family. So we're relaxing, we're creating something new where people come and we end up building massive wait lists because we find markets that are underutilized and where they have no solid housing. So you come in and you, you supply something new. It's going to, it's going to run up. So I can imagine coming to the larger metropolitan market, the thing that you're going to have to look at is you're going to have to bring a ton of more capital because real estate is so expensive here.
Ray Gutierrez
Oh yeah.
Jeremy Yost
It's, you know, compared to Illinois, it just, it blows my mind. Yeah.
Ray Gutierrez
It's insane.
Jeremy Yost
Or even, or even even some differences just from like Tampa. Miami is just a market of its own.
Ray Gutierrez
Oh yeah. It's a different beast. Try being born and raised here. And it's interesting to evolution. I disappeared for 10 years and lived in San Francisco and from there went to Tulsa, and from Tulsa went to Austin. From Austin went to Switzerland. Great. Ten years. And then I came back. I was like, holy shit. Miami just became the Miami of the TV Miami. But from the 80s, it's like, now we're in the future of what we knew Miami was going to be. So you look around and it's just like, all right, we're kind of like in the 1980s of the future, but it's really 2025. What do you think culture is like? And how do you think culture is responding to this new wave, new age of real estate living? Families, no families, no children. Like, it's totally different. 1995 is nowhere near as close as 2025.
Jeremy Yost
Well, if you think about it like, our generation is probably the last generation that really played outside a lot. Yeah. And our parents really didn't know where we were. We were gonna go ride our bike
Ray Gutierrez
and hey, we'll, let's go hang out with aliens and. And we'll go to you.
Jeremy Yost
We'll go do whatever. I'll call you when I get to a friend's house to let you know I'm fine and find out what time I need for supper.
Guest/Additional Commentator
Yeah, dude.
Jeremy Yost
And that whole generation's changed because we're in an industry that everything revolves around technology where, where we had to wait for Things.
Ray Gutierrez
Yeah.
Jeremy Yost
Now the kids these days, they don't have to wait for anything. If they want something, they can door dash it, they can Uber eats. If they want to get something, anything is at their right in their hands. They can have everything now. So it's changed the real estate game in the sense that oh, hey, let's do virtual tours. I don't need to physically go to somewhere or you pop a lock on a door, you give them a code and they a self guided tour and go in. So the markets change, the dynamics completely changed. It's not the people, it's the time. So with times, everybody's got to do some change and make the best of what it is because technology is going to take over everything.
Ray Gutierrez
Oh yeah. And when I drive down through, through Miami traffic over the causeway, it's beautiful. It's to see these giant art pieces, these giant waves that they're building. Like Miami's become like the next to buy the next Las Vegas or vice versa. But there is, it's becoming bleak because you know, AI is catching up and AI is, is AI in itself. And like I'm looking at this landscape, at all these buildings, I'm like, I can't help but think in our lifetime and maybe 20, 30 years, you know, floors one through 15 is, you know, single men, single women. Floors 15 to 30 are just people in AI chambers that are just like compacted. As to now you can kind of see it like in 30 years they, it's gonna look a little bleak and sad. I don't feel like it's gonna be about open roads and farms anymore.
Jeremy Yost
I can't even imagine. Oh, it's 20, 30 years from now. Or if we ever get to a point where we actually have real flying
Ray Gutierrez
cars, I would hope so. But I mean, have you seen humanity in just regular four wheels?
Jeremy Yost
I know, it's crazy. I mean there's just bad drivers everywhere, dude.
Ray Gutierrez
But that's what I'm saying. There's, there's a blue ocean market out there because there's going to be that dichotomy of men like you and I that just want to raise a family or just want to hang out with their dogs. I just want to see water. And then I just want to see an electronic store where I can buy a gadget that I can go take to my huge manhouse and do my thing. Like there's going to be a market of like deep pocket or folks that are just sick of the Miami, sick of the la, sick of the New York and they Just want to see green. They want to see soybeans. Enough sand. Oh yeah, soybeans, yeah. They want to go back to the traditional farmland. They want to pull calf at 4:44, 45 in the morning.
Jeremy Yost
Or they just want to go back to nature.
Guest/Additional Commentator
Yes.
Jeremy Yost
You know, I, I'm seeing, I've got some friends in the real estate market that are building micro homes in the middle of nowhere. It's kind of, it's. But they're, it's like micro boutique hotels or the, they're building, building them in like tree houses and where you're just freaking looking over an exotic view of a jungle and the Caribbean and you know, different aspects of like, oh, well that's cool. I would have never thought of that. What made you think of it? Well, with the way technology is, let's go back to the basics and appreciate nature. So not only are they doing that, but I'm seeing them go into spaces where they're in like Colorado. But doing it in the mountains, that's like looking over the mountains and you're in just like a small little cabin. But they group them all together to give it like a hospitality feel. But it's more nature based, which is really kind of cool because we can all get so caught up with technology and lose sight of using our real eyes to see real things, see the
Ray Gutierrez
actual photons that are in front of us saying, this is reality and life, you dumb human being. Please enjoy it.
Jeremy Yost
Yeah. And it brings you, brings you back down to earth to where you can just live. And I, you know, I'm one of
Ray Gutierrez
those people live longer.
Jeremy Yost
Absolutely. And you know, it's what's I found that's hard for me is I have a hard time sometimes shutting off.
Ray Gutierrez
Oh, same.
Jeremy Yost
I just, I'm like so caught in and I've really tried, you know, incredibly hard to focus on this. And I, I've got to give credit to my girlfriend Liana because she's an operator. Yeah, pretty much.
Ray Gutierrez
I have an operator as well.
Jeremy Yost
You know, she helps keep me grounded in the sense that, you know, when I'm with her, we go out and we experience nature or just be in the moment and be present. And it's really helped me, especially in the evenings, shutting down for work mode. It's like I try to put my phone away and I try not to look at an email if somebody's working late or check everything. People time.
Ray Gutierrez
It's the itch.
Jeremy Yost
It is because it's like I want to be prompt, I want to be good. But Then it's like, I can't go to bed. I'm wi. I'm. I'm wide awake. Where the hell am I going to
Ray Gutierrez
the gym now 36, you know, it's just like, damn. Damn.
Narrator/Host Introduction
Yeah.
Jeremy Yost
Let me just live.
Ray Gutierrez
Yeah, dude, I hear you.
Jeremy Yost
And so, you know, it's just adjusting through everything, and it's just. It's only. I think it's only going to get worse.
Ray Gutierrez
It definitely is, which is why I'm like, dude, there's a whole blue ocean out there, man. There's a whole dichotomy of men and women and everything in between. They just want to go out and disappear here and return to nature and go, all right, I guess I'll go back into the gizmos and the ticket. Taka. Takatoku. Because my AI bot's already tired of being an AI bot. And my VAs have all quit because my AI bot's better than my VAs. And my Optimus has killed two dogs already. God damn it. I can't get a new Optimus anymore because it's cost me already $22,000 to buy two of them. That's going to be the future in five years.
Jeremy Yost
And now it's like the time is now. Because as my company has been growing, I've started utilizing more AI, more technology, because I want to work smarter, not harder.
Ray Gutierrez
Yes, sir.
Jeremy Yost
And I hired two VAs, and I've got some AI employees that kind of help with my day to day, like, executive schedule.
Ray Gutierrez
Yes, sir.
Jeremy Yost
And it's given me time back to where I can do a little bit more or focus on some new projects. So, you know, there's the good side to it, as long as you don't let it get away.
Ray Gutierrez
Yep. What I like to do is compartmentalize my AI. So from the day of birth, 1983 to 2020 is my AI. 20 to 2025 is my personal experience that I've yet to monetize everything before that. This is my AI. I've packaged it.
Jeremy Yost
Here you go.
Ray Gutierrez
And then it's like, sell it. This is my life experience. But from 2020 to try, it's my own experience that I'm still crafting that I'll eventually outsel.
Jeremy Yost
Well, but you. You are who you are because of where you started and what you. Where you came from. And that develops your story, your path, and you can essentially, you make it your own. Yeah. You control your destiny. Whether people. I hear people all the time complain, whether, well, I can't do this. I can't do that. Well, you can. You just got to change your mindset.
Ray Gutierrez
Yes.
Jeremy Yost
Anyone's capable of doing anything. Where there's a will, there's a way. You just got to figure out how to get there.
Ray Gutierrez
Yeah, it's not anti war, it's pro peace.
Guest/Additional Commentator
Yes.
Ray Gutierrez
Yeah, that's the trick. It's pro peace. They wrote it in the secret a couple of decades ago. It's called the secret. Anyways, I wanna, I wanna gas you up, man. Something that really finds, that I find interesting is Universal Studios, Disney World, Disneyland, these, these amusement parks. They're terrified of people like you because you're manufacturing experiences and then listing them on Airbnb. Disney has tried and failed even with Star Wars. They tried peddling a $5,000 three night experience in some garage and they half assed it. And the cynical deep pocket Star wars motherfuckers that have the whale money spend three hours on YouTube complaining about it and that video gets millions of views trolling Disney because they're trying to create what you're doing. Good for you.
Jeremy Yost
You know, and here's the thing with that. Like they obviously they're good at what they do.
Ray Gutierrez
They used to be, but when you,
Jeremy Yost
but when you brand off and you try to do something new, sometimes you try to oversell something and you cut too many corners and you price people out.
Ray Gutierrez
Oh, yeah. So WWE is doing that now. Sorry.
Jeremy Yost
Well, no, no, they are. I'm a huge wwe.
Ray Gutierrez
Yeah. You know, those arenas are empty, you know, and.
Jeremy Yost
Well, and they've downsized their arenas too, so they're packing more.
Ray Gutierrez
True, very true.
Jeremy Yost
And so, you know, like most businesses, they've increased their prices because they want to pay their debt off. They want to, they want to get their. Yeah, they want to get their debt gone.
Ray Gutierrez
Oh yeah.
Jeremy Yost
And then they'll probably change their prices. They're trying to, you know, they're trying to navigate and figure things out post Vince McMahon.
Ray Gutierrez
Yeah, yeah, yeah.
Jeremy Yost
But you know, their shows, their stories have gotten better.
Ray Gutierrez
Absolutely.
Jeremy Yost
It's just the price point.
Ray Gutierrez
Yes.
Jeremy Yost
And I think there's a method to their madness where they're going to hit certain things and then turn a corner and then bring it back to more of the Vince era of getting the families.
Ray Gutierrez
Yeah.
Jeremy Yost
But they had to make a change to separate themselves because of not just the sale, but because of whatever issues were going on.
Ray Gutierrez
Oh, but it's great. That's going to become a WWE wrestling podcast. It's good to see good old Hunter Hearst on Netflix, like with a tight shot, talking about, you know, KFAB and the. The rules stuff that we've tried
Jeremy Yost
changing from, you know, coming X. Yeah. They're coming in from Hunter, Hearst, Helmsley and. And pivoting to that great story. Just the evolution of now being a big executive. That's a prime example of showing anybody can do anything because, you know, he didn't have a college background, but he had the showmanship of being a high quality wrestler turned executive to a massive corporation that's now publicly traded. And part of TKO that the sky's the limit so you can start something and end up at the top of the food chain all by hard work because, you know, grit beats anything. And at the end of the day, I don't care what anybody else says, if you're the hardest worker in the room, at some point in time, you're gonna end up being the big dog.
Ray Gutierrez
Oh, ye.
Guest/Additional Commentator
Yeah.
Ray Gutierrez
Yeah. And the thing about wrestling is they fight for grit. They're action heroes and they look so good doing it. And that's what that's. I feel like that's the American spirit, where it's like. Like watch how good I am at doing what I do.
Jeremy Yost
It's a soap opera for guys.
Ray Gutierrez
Absolutely.
Guest/Additional Commentator
Yeah.
Jeremy Yost
You know, you can get in and, you know, you get hooked on the story lines. And obviously it's just entertaining to watch. And while the moves they're doing is real, it's the who wins and loses is what's planned. And that to me, that doesn't matter because they're doing some really cool. That I can never do because I'd probably end up in the hospital trying to do any of it.
Ray Gutierrez
Jason here, he. He filmed Kurt Angle.
Guest/Additional Commentator
Yeah.
Ray Gutierrez
Oh, yeah. He was in the room with Kurt. Yeah, yeah, I was the same.
Jeremy Yost
Got a gold medal with a broken freaking neck.
Guest/Additional Commentator
I know, bro.
Ray Gutierrez
And there's Rudy and Gokura. Like, what world am I in?
Jeremy Yost
It was awesome, you know, and, you know, it just goes to show, all walks of life goes full circle and everybody can win.
Ray Gutierrez
Well, how do you feel to be part of a quite a luminary cast of characters, sir?
Jeremy Yost
You know, with all the. Yeah, with. With the cast and everything, it's. It feels pretty incredible because I see myself coming from Charleston, Illinois. It's very small town, like 16, 18,000 people maybe.
Ray Gutierrez
Yes, sir.
Jeremy Yost
You know, we've got a very small university, Eastern Illinois University. You know, Charleston's probably best known for Jimmy John's was created there.
Ray Gutierrez
Right on.
Jeremy Yost
So the original store is there. And, you know, Easterns had some very famous athletes pass through, so you know, it's known because of some people that went through there, but we're in such a small area, so to be a part of something and with the like, in my eyes, legendary people that have came on this, it's such an honor to, to be a part of it because I just feel like I'm a small town guy and, you know, being where I'm at and mentioning, you know, cornfield and soybeans, you know, I still see almost at least one, two days a week. We have a large Amish community by us. So I still see, you know, Amish and the horse and buggy. And so then coming to Miami, it's like instant, like change and it hold changes, stimulation and, and getting into like a city vibe and it's just like reinvigorating and it's just all of it's really, really cool. And it's such a blessing to be able to be part of this family and be in with the big names that have passed through.
Ray Gutierrez
Right on, Jeremy. Well, now I get to hang out with you. You are a big name and I'm just a dude that hosts podcasts in a skirt.
Guest/Additional Commentator
Whatever.
Ray Gutierrez
Carrie, man, such a pleasure.
Jeremy Yost
Thank you so much.
Ray Gutierrez
I look forward to breaking KFAB with you after this podcast. Absolutely. For that. This is Jeremy Jost and I am Ray Gutierrez. Happy Friday. And we are inside Success.
Living Your Legacy Podcast: "How a Small-Town Developer Built a Real Estate Legacy"
Date: July 3, 2026
Host: Ray Gutierrez (with Rudy Mawer as executive producer)
Guest: Jeremy Yost – Real Estate Entrepreneur, CEO of Yost Management Services, Co-Founder of Innovative Development Partners
This episode dives deep into the entrepreneurial journey of Jeremy Yost, a second-generation real estate developer from small-town Charleston, Illinois. Jeremy shares how he broke out from his father's shadow to establish his own legacy, the practicalities and philosophies of modern property development and management, and his thoughts on culture, technology, and the evolving landscape of American housing. Through candid back-and-forth with Ray Gutierrez, listeners get advice, untold stories, and actionable insights into building a business, navigating market trends, and staying true to one's roots.
"I didn't want to just be known as Dan yo son. I wanted to develop my own identity and I was able to do that and persevere..." (00:00, 03:46 - Jeremy)
"I wouldn't be where I'm at today for sure if I didn't have such an amazing mentor in him." (03:59 - Jeremy)
"What most people think is crazy, I think is normal." (04:42 - Jeremy)
"If you think you’re going to fail, you’re going to fail." (05:37, 00:30 - Jeremy)
"When I pull that trigger, I'm balls to the wall, 110% all in and make sure that the project gets done right." (06:02 - Jeremy)
“We’ve developed all over Illinois, expanding into Indiana, Florida, looking at Missouri and Kansas, and hopefully go nationwide.” (07:03 - Jeremy)
"It's more not just about operations, it's about retention and your tenants. If their overall experience is really good...it's going to go a long way." (08:43 - Jeremy)
"Twenty years ago, the average age for first time home buyer was like 27, 28...now in 2025 it's like 42." (11:12 - Jeremy)
"Everything revolves around technology…[now] you can do virtual tours...the markets change, the dynamics completely changed." (14:07 - Jeremy)
"I'm seeing friends building micro homes…tree houses where you’re just looking over an exotic view...appreciate nature." (16:18 - Jeremy)
“What I found that’s hard for me is I have a hard time sometimes shutting off...” (17:33 - Jeremy)
"I hired two VAs, and I've got some AI employees that kind of help with my day to day....It's given me time back..." (19:17 - Jeremy)
"Sometimes you try to oversell something and you cut too many corners and you price people out." (21:20 - Jeremy)
"You can start something and end up at the top of the food chain all by hard work. Because, you know, grit beats anything..." (22:43 - Jeremy)
"I just feel like I'm a small-town guy...so to be a part of something with like, in my eyes, legendary people. It's such an honor..." (24:26 - Jeremy)
"At the end of the day, no matter what, you have to believe in yourself." (05:50 - Jeremy)
"We're in a good position in the renter space...more people nowadays, they're renting more than buying homes." (10:31 - Jeremy)
"Technology is going to take over everything...with times, everybody's got to do some change and make the best of what it is." (14:07 - Jeremy)
"I have a hard time sometimes shutting off...I've got to give credit to my girlfriend...she helps keep me grounded." (17:38 - Jeremy)
"If you're the hardest worker in the room, at some point in time, you're gonna end up being the big dog." (22:43 - Jeremy)
Jeremy Yost’s story is a testament to the power of mentorship, resilience, adaptability, and authenticity in both business and life. Listeners come away with actionable advice on mindset, property management, market timing, and maintaining personal balance amidst the relentless pace of modern entrepreneurship. The episode offers not just business strategies but also heartfelt reminders about the value of real connections, roots, and “living your legacy” beyond mere financial success.