From Pilot to Property Mogul: Chad Freeman’s Inspiring Real Estate Journey

Dylan Silver (00:01.062)
Hey folks, welcome back to the show. I’m your host, Dylan Silver. And today on the show I have Chad Freeman, real estate investor entrepreneur focused on finding deals other investors miss and flipping the script on distressed real estate. Chad, welcome to the show.

Chad Freeman (00:19.054)
Thanks Dylan, it’s nice to be here man.

Dylan Silver (00:21.444)
Absolutely. Today you’re out of a hotel in Tribeca.

Chad Freeman (00:25.74)
Yep, one of the first times I’ve been excited to see New York.

Dylan Silver (00:29.902)
I know I’m from just outside that area as I was mentioning before hopping on here. I tell people I miss really two things. I miss some of the Italian American culture. I miss some of the Italian food and that’s about it. Because I don’t miss the cold. I don’t miss the traffic and you know people say that traffic is bad up here and it definitely is but there’s something a little bit different about New York traffic.

Chad Freeman (00:47.192)
Okay.

Chad Freeman (00:56.984)
they have like next level traffic. Stuff that lasts for days, I think sometimes, right? Yeah, that’s like a…

Dylan Silver (01:01.104)
Yeah.

Sometimes you’ll just look at it and you’ll be like, well, I’m not going in today because there’s too much going on here.

Chad Freeman (01:08.334)
I always think of it because Trump has a helicopter, right? Makes sense when you figure out New York. Like, yeah, you need one.

Dylan Silver (01:14.374)
Yeah?

Although with everything that’s been going on with the helicopters and the planes, I’m scared, but that’s another topic here. let’s talk about how you got into the real estate space. For folks who always see the success but don’t see the origins, what was your origin story?

Chad Freeman (01:31.276)
that’s kind of cool actually from where I’m sitting at right now. So I said, it’s the first time I’ve been excited about New York. I’ve always been put to New York. I’ve been placed there due to my job. And this time I came up here for real estate stuff. So it’s a lot different perspective. I like a lot more, but I originally started over in Jersey city because I worked for the airlines. So was running a pilot crash pad where you rent out rooms in south of the airport in Jersey city.

Or I’m sorry, not Jersey city, Elizabeth Seaport in New Jersey. Totally hell hole place. You don’t ever want to buy a house. And I had no idea what I was doing. Yeah.

Dylan Silver (02:12.476)
You know what the thing is about Elizabeth is that I went to an area, it was Elizabeth, and it smelled terrible. And I said, I can’t confirm neither nor deny, but I will say that Elizabeth does not have the prettiest reputation among even fellow New Jerseyans.

Chad Freeman (02:29.358)
Well, the seaport makes it worse, I think. So I had a cop apologize to me when I told him I was a homeowner.

Dylan Silver (02:40.272)
That’s a funny, that’s a funny one. So you got your origins in the airline business, owning real estate out there. At what point in time did you see this was a possible entrepreneurial avenue for you?

Chad Freeman (02:53.386)
So I guess I’m third generation real estate. Nobody was a true professional, but I’ve been wanting to do real estate since I was, I don’t know, in my teens, I guess. I grew up with my parents doing real estate and renting condos and the lockbox name on the lockbox was Kid, because it was for our college and our future. So I saw that from a young age.

And I knew I wanted real estate to provide stability for the airline career I was choosing because it’s super unstable. Yeah. yeah.

Dylan Silver (03:26.32)
Really? Let’s pivot here and talk about that. I thought airlines would be super stable.

Chad Freeman (03:32.124)
no, they’re super cyclic. Right after nine 11, I lost my job. And then we had the great recession hit, which was like a huge pause button. And then they had the age 65 rule go through, which is a five year pause button in the middle of that for me. So it was like really stagnant and you go through, you know, bad downturns you get furloughed cause it’s all seniority systems. So you’re, you know, you’re placed at the bottom and you just wait.

Dylan Silver (03:38.556)
huh.

Chad Freeman (04:01.164)
see how far you get up in your career. But once you get down the road with good, like good seniority in a major airline, then you start feeling okay. But it was probably 10, 15 years before I started feeling like my job’s really secure. Even after COVID, COVID’s hit and all the way back, this airline have been super unstable for a long time. But with COVID, I remember our CEO saying, the way the airline’s running right now,

We need 2000 people, 2000 pilots, sorry. And I was like number 8,400 out of 13,000. I’m like, whoa, I thought my job was safe. So it can like, it turns on a dime like that sometimes. don’t really necessarily see it coming. And real estate’s awesome, right? More people made millionaires from real estate than anywhere else.

Dylan Silver (04:51.996)
I was totally unaware that airlines were cyclical. But now that I’m thinking about it, it makes sense because when people have a flat set of money, they can travel and things are not so good, they can’t travel or they’re traveling less. That checks out. But in that, I’m imagining you’re seeing because you mentioned third generation real estate and then you mentioned the cyclical nature of your career. These are actually two cyclical things in and of themselves. You’ve got the cyclical real estate.

Chad Freeman (05:20.979)
yeah.

Dylan Silver (05:21.766)
and then you’ve got the cyclical career, has there ever been a time where that’s kind of like accentuated on both ends?

Chad Freeman (05:25.646)
Good point.

Chad Freeman (05:31.67)
Well, when you say that, you know, having a job in a W-2, you have no control. You do, you have control on what you choose to do and where you choose to work or whatever. But after that, especially with the airlines and the seniority systems, just luck in a waiting game. So with real estate, yeah, cycles are great because you can buy a lot of stuff for really cheap during a downturn or at the bottom, right? And if you do it correctly, you can go through up, down, sideways, whatever market you want.

in real estate and still make money. You can’t do that with a W-2 airline job.

Dylan Silver (06:06.128)
Definitely not. not. Do you have experience with multiple airlines or were you working with one for a majority?

Chad Freeman (06:13.466)
Yeah, when I was younger getting flight time, was bounced around a little bit more. I got cut right after 9-11. So I got hired at the beginning of 9-11, lost my job at the end of, or 2001, lost my job at the end of 2001. And then went to a different airline, got recalled a couple years later back to that original one, and then moved into the majors from there. So I haven’t had a ton of moving around. mean, some people I fly with have had like, don’t know, six different major airline jobs or something.

I’ve been here.

Dylan Silver (06:42.822)
How common is it that you’ll see pilots getting into real estate investing? And I ask this because you would think in my mind, because you’re moving so frequently and you’re seeing so many, or I shouldn’t say moving, but you’re all over the place and seeing so many different areas of the country, that you may have greater exposure to real estate investing. But at the same point in time, because you’re always traveling, it can be tricky and hard. And some people may say, well, I’m never in one place for too long. How can I do real estate investing?

Chad Freeman (07:12.75)
You just got to figure out how to do it remotely, right? How outsource the certain things, but you do have to, yeah, you need boots on the ground or something, or connections, partnerships. And that’s really what I’ve learned is that’s where everybody doing volume is just doing lots of partnerships. Cause there’s never enough of your time to go around and do everything.

Dylan Silver (07:16.028)
You stay.

Dylan Silver (07:30.108)
Yeah, yeah, that’s true. Those first deals that you had, was that early 2000s? That you had those first deals for yourself personally?

Chad Freeman (07:38.68)
That first one I bought a new build retail in 2005 in Elizabeth Seaport, right in middle of the hole, right before the whole meltdown. I was part of the reason why I think I wasn’t making any money, right? And I got this loan. I knew I was going to rent the house out so I could cover the loan at least. was at least that smart to do a few numbers. I didn’t even know what due diligence meant, but.

So I knew I could cover the loan and the guy on the phone, he’s like, well, you don’t make enough money to qualify for this loan because that’s okay. It’s a no doc loan. We’ll just say that you make more. Like, okay, cool. I was like, why I can cover it. I’m going to put renters in it. And he’s like, all right, we’ll just tell me you make more. Then I got the loan.

Dylan Silver (08:18.876)
Crazy.

Dylan Silver (08:27.398)
So at that point in time did they have these DSCR loans? It kind of sounds like that’s what it was based off of, but I doubt that that was a term back then.

Chad Freeman (08:36.206)
Yeah, was something similar. mean, no wonder we melted down. They didn’t need to cover the loan. They lied and said I made more. And then, yeah, it was just they did like a 95 % loan to value because I was first time buyer and then a 3 % HELOC or something to where I walked away with cash.

Dylan Silver (08:40.624)
Hahaha

Dylan Silver (08:58.938)
Whoa. That’s a wife. Wow.

Chad Freeman (08:59.97)
Yeah. Yep. I walked all the closing with some, thousand bucks or 2000 bucks or something. Well, they paid me by the house.

Dylan Silver (09:08.924)
Okay, so then.

At that point, you walk us through the story of that first deal? So you found the house, it was new build, did you find it on the MLS? Did you have a realtor? Did you find the renters yourself? How did that work? And then at the same time, you’re traveling all the time with your job, so how did managing it work?

Chad Freeman (09:30.814)
well I was living there actually. I was… I found a realtor I liked and he drove me all around, showed me the different areas. He was good for that. But then… Said that there was rumors going in from the seaport to Manhattan with a ferry. I’m like, dude, I’m gonna make a ton of money. So I just bought the house. Now I just wait and make a bunch of money, right? Well, there’s no ferry. There’s still no ferry there today, 20 years later or whatever.

Dylan Silver (09:32.774)
Okay.

Dylan Silver (09:47.836)
Yeah.

Chad Freeman (09:59.982)
I had a really bad gut feeling you should never ignore. had that. I ignored it. Luckily I dodged a bullet. So I found out just this bad gut feeling and I kind of made it go away with six months online Trump University actually when he was doing that. I wish I could remember who taught the class. was a billionaire that taught the class. was quality material and then it taught me how to make money.

Dylan Silver (10:04.592)
Yeah, I do know.

Dylan Silver (10:18.683)
Okay.

Chad Freeman (10:26.798)
And so I sold that and I saw, was just starting to like study the market and learn more. And I saw the downturn coming and like, Oh crap, I better get aggressive on sales. So I use like aggressive sales techniques that they had taught. put a flat screen TV and a barbecue in at the time and it got it sold. I bought it for like 427 sold it for 444. And then I saw a few years later listed for 200. It was the highest listing in the neighborhood. No.

Dylan Silver (10:49.532)
You’re kidding.

Wow, what year was that, like 2010?

Chad Freeman (10:53.432)
there.

I bought it in 05, I think I sold it in 07.

Dylan Silver (10:59.068)
And so when did you see it at 200,000 and some change? Around 2010, yeah. Wow. Now I’m curious, pivoting a bit here, Chad. So during this time period, you’re flying all over the country, And so how is your third generation, so you have that benefit, it’s not like this is brand new to you, but it is new being a pilot and being…

Chad Freeman (11:01.836)
Yeah, when you said something like that and

Dylan Silver (11:25.508)
a real estate investor. So how are you finding deals? Is it was it at that point in time more of a hobby? Was it something like I’m going to keep this in my back pocket and when things slow down, how are you managing the deal flow with with so much travel and with a full time job that’s very intensive?

Chad Freeman (11:43.713)
because it’s not very intensive. So when I go to work now, especially I get long breaks, we have a bunk bed, I can go to sleep. So you get a lot of downtime, you get long layovers. Even back then I was flying domestic, but you get a lot of downtime, you know, and so you get a lot of time to read and you get a ton of days off too. So now by law,

because I fly efficient schedules when I’m on a leave of absence right now. But when my worst work month, I’ll have to work like 12 days because I time out and the FAA says you can go to work if you want to. And then it’s all, it’s all long haul, you know, so my longest flights have done are like 16 hours. So then you’re getting seven hours of sleep in a bed and you can change into your underwear and go to sleep. It’s in the top of the airplane. So it’s like, it’s super

Dylan Silver (12:24.956)
Hmm.

Chad Freeman (12:37.486)
Easy. Once you work your way up and get some seniority becomes extremely easy. It gives you a ton of time off. So you asked if a lot of pilots are in a real estate, not as many as I would think, but the original guy that got me interested in mobile home parks owned mobile home parks and he flew, but he, he never had to go to work. He just flew when he felt like it kind of, cause you can also drop trips and get other people to pick up trips. So once you, his comment was concreted into my head. He said, this job becomes really great.

Dylan Silver (12:47.291)
Yeah.

Chad Freeman (13:07.084)
once you no longer need it.

Dylan Silver (13:10.289)
Wow.

Chad Freeman (13:10.35)
I was like, okay. So there’s a few other guys I know that do some real estate. One guy in particular, one of my favorite guys to fly with, he bought, 20 years ago or so, he bought some multifamily, couple of unit, 20 unit buildings, I think in Chicago. So he told me since my forties, I’ve saved every dime that I’ve gotten paid at the airlines. He’s just had that much cashflow from his real estate.

Dylan Silver (13:38.46)
God bless. So you’re one of the investors that I’ve spoken with. I’m trying to think if I’ve spoken with too many people. There’s one other gentleman who does industrial that I spoke with in New Jersey, but that are or have invested in New Jersey in single or multi-family. It is challenging. It is a little bit trickier to invest in single and multi-family in the East Coast and definitely in New Jersey. If I’m comparing it to like where I’m at in Texas, there’s a higher price point, right?

Chad Freeman (13:39.65)
Right?

Dylan Silver (14:08.153)
there’s in many, many cases more favorable towards tenants than to investors and landlords. And so as someone who’s invested in that area, were you at any point in time thinking, okay, I’m going to invest all over the country. And if that did happen, how did that look? Or have you stuck to that area in that tri-state area?

Chad Freeman (14:29.122)
That’s a good question. I’ve become allergic to this Tri-State area except for visiting for some meetings now. So I had dinner with Leo Young. You’ll find him on Instagram. He does mobile home parks. We’ve been talking for a few years about how to maybe partner and grow our mobile home park businesses. And then I got a meeting with some guys that do big building stuff all over today. So that’s exciting. But.

We operate in Texas. That’s our main focus. And then my mobile home parks are in the Midwest, in Michigan. But we live half our lives between downtown Dallas and Jacksonville, Florida. So that’s where we’re really doing the single-family home stuff. It’s good. I like where we’re at.

Dylan Silver (15:07.356)
I’m so jealous.

Dylan Silver (15:13.924)
trying to move part-time to Florida I don’t know how I’m gonna do it but I love DFW probably for a lot of the same reasons that you do my personal kind of proud Texan belief is that this is the number one market for single-family homes in the country but I also love love just aside from real estate love Florida

Chad Freeman (15:28.759)
yeah.

Dylan Silver (15:35.876)
Every time that I’m going through Florida, I’m like, this place is amazing. Like specifically Fort Lauderdale. I don’t think I’m far enough along my real estate journey here, Chad, to be able to afford to live in, you know, West or South Florida, you know, that area. Excuse me, I could probably do West, but I’m thinking like St. Pete, Saratoga area, maybe I could do that. But for Miami and Fort Lauderdale, I think that’s a little bit of a ways away, but I am jealous.

Chad Freeman (15:55.79)
that’s been a song here.

Chad Freeman (16:01.996)
I want the penthouse suite on top of the Ritz Carlton there in Fort Lauderdale. That’s my dream penthouse.

Dylan Silver (16:07.802)
Yeah, please do it for me. I don’t know how one gets there, but I need some motivation here. I tell you, I’m a big traveler. I tell people this, that some of the best investments that I’ve ever made have been in masterminds that I’ve gone to, conferences that I’ve gone to, getting a passport and traveling abroad. And every time that I do travel abroad, I tend to be going through South Florida for one reason or another. Just a lot of connecting flights over there. And so…

As I’m going through there and I come back, I’m like, man, this is so nice. How do I move down here? And so I’ve been doing that now for about two years. And so I come back through there and I’ll be in Fort Lauderdale and it’ll be, you know, February. It’ll be beautiful outside. There’ll be retired people or semi-retired people with more money than they probably need. But enjoying life to the fullest and

Chad Freeman (17:04.547)
Yeah.

Dylan Silver (17:06.608)
I’ll be over there they’ll be, you know, more than happy to talk with me about real estate or anything else and I’m like, man, what a vibe.

Chad Freeman (17:13.874)
yeah. A lot of money there too. The baby boomers and retirements and yeah, man, between Jacksonville, where we’re at, the growth and the money going into Jacksonville, that place, it was deemed like a supernova market similar to Austin, right? It’s supposed to blow up. Then Dallas, Houston, San Antonio, Austin, man, the growth there and the stuff that’s going on in real estate. It’s like the best time ever to go get rich in real estate in Texas and Florida right now, I think.

Dylan Silver (17:41.954)
It is the best time ever. I tell this to people that you can either be on the side of it where it’s like, wow, specifically millennial Gen Z. You can look at it like, wow, these homes are super expensive. How do I afford a home? Or you can look at it like these homes are super expensive. Let me benefit from this appreciation so that I’m not on the opposite side where I’m having no benefit from inflation. Let me benefit from it.

Chad Freeman (17:43.65)
Hell.

Chad Freeman (18:08.844)
Yeah, totally. It’s awesome. And your mortgages get cheaper with inflation.

Dylan Silver (18:11.877)
So.

Dylan Silver (18:16.122)
Yeah, that’s exactly right. There’s all these different things that I’ve learned about since becoming a realtor. I got a real estate license after being a wholesaler for about two years. And the reason, Chad, was because I got tired of real estate agents basically being like, you’re a wholesaler. Well, you know, I don’t want to have anything to do with that. And so I was like, man, this is crazy. Like, but then I went to real estate school and in-person classes at Champion School in Fort Worth, which is like a big real estate school out here.

And I love this school. I’m very grateful to them because the test, in my opinion, was super hard. At least I thought so. And I passed on the first try. But I saw that there was this huge divide between real estate agents and wholesalers. And basically, real estate agents view wholesalers as unscrupulous characters. And wholesalers view real estate agents, and both for good reason, as like these people that just kind of have their nose up in the air. And now that I’m both.

I see both sides of it and I just think that, hey guys, let’s be problem solvers, let’s figure this out, let’s come together. The real estate agents are held to a higher standard because they have the public trust so they can’t do things like make a cash offer when they have zero intention of actually buying it themselves, which wholesalers in many cases can do. Right, and so.

Chad Freeman (19:32.385)
Right.

You can still assign equitable rights as a realtor, right? You just have to disclose.

Dylan Silver (19:41.434)
You have to disclose to the nth degree. So you have to be like, look, Chad, I’d like to make a cash offer on your property. I may assign this deal or I may buy it myself. This offer is going to be below market value. I’m an investor. Like you have to go through the nth degree. Where a wholesaler, because I’ve been one, can just come in and be like, I’m buying your house. Yeah.

Chad Freeman (19:57.454)
Yeah.

Chad Freeman (20:04.962)
Yeah, you know what you’re doing. And it’s the mindset, I think, and the different way of thinking that most realtors don’t have. And from what I know, most realtors really don’t do much. They move a home or two a year. And then if you get top realtors with an investor mindset, now you really got a combo.

Dylan Silver (20:17.606)
Yeah.

Dylan Silver (20:21.948)
That’s what I’m trying to do. That’s what I’m trying to do. That’s a whole other podcast, this strategy. In Texas, you’re familiar with this chat. We have Roddy Report, right? And so there’s lots of opportunity in there that I see, especially for an investor like myself that’s…

I would say still in the beginning phases, right? If I think of the career path of an investor, think about kind of just getting in, getting your first couple deals, wholesaling, maybe doing some fix and flips, short term, midterm, corporate housing, long term, people might get into commercial, they might do note buying, hard money lending.

There’s so many different avatars. You might get into medical office space, right? And I’m kind of right there where I’m in the wholesaling phase. I’ve worked on fix and flips. I don’t have my own fix and flip yet, but I’ve done enough of these where I’m like, let me get that first fix and flip deal. Let me make that happen.

Chad Freeman (21:12.558)
So I flipped the perfect buy and hold home. So I’m trying to figure out a exit or a non exit strategy to get out of hard money and then keep that thing. This is, it’s like, it’s in North Dallas, the dirt’s appreciating it, you know, 10 to 13 % right now. And you can just watch this thing going up $7,000 a month. No, I don’t, I have no interest in Airbnb. I’m interested in, you know, the single family we’re doing.

Dylan Silver (21:32.7)
Do you do Airbnb? You don’t do it. Yeah.

Chad Freeman (21:41.13)
and then mobile home parks and ultimately mobile home parks and big buildings are what interests me the most.

Dylan Silver (21:46.118)
Huge. Mobile home parks are huge. they’re going to be even, do you do the, there’s a couple different avatars of this that I’ve seen. I’ve done, I’ve seen mobile home parks that are basically like super cost effective housing. And then I’ve seen mobile home parks and people and I even will get confused, but because there seems to be some overlap between mobile home and RV, there’ll be these like super upscale versions of these. Now, which avatar are you falling into?

Chad Freeman (22:07.982)
Mm-hmm.

Chad Freeman (22:14.228)
We’re in Michigan, so it’s just affordable housing. Nothing fancy, no amenities, no pools, no clubhouses, no nothing. Just a nice, peaceful community with, you know, that’s a clean, good space with good people in it, but it’s just affordable housing.

Dylan Silver (22:29.478)
There’s gonna be more and more and more and more and more of that. I’ve even seen, I’m sure you’ve seen it, there’s these ADUs that you can buy online. I don’t know anybody who’s done this, but I see you go on like Amazon, you can buy a house, you know what I mean? Like, or an ADU, I should say.

Chad Freeman (22:44.226)
Yeah, there’s some really cool manufacturers too around Florida that are doing hurricane resistant stuff. I know a couple of them, visited one factory and then I’m friends with some other guys that are doing startup. That’s pretty cool too. They’re doing like AI builds with, they call it grilled cheese sandwich technology where it just sandwiches in metal frames with epoxies and finishes. And then they, they can do.

affordable housing, vacation, rentals, apartment complexes, even they can stack them up. But the problem with mobile home parks is you got to have a HUD stamp, HUD sticker. And the tiny homes, we need an industry disruptor, but the tiny homes won’t do it. They’re too small. You can’t put a family of four in it, you know, and can’t have a king sized bed in it.

So once somebody comes up with something clever for mobile homes, cause they’re this ugly rectangle right now, they could really use some elevations and porches or finishes on the top, know, but outdoor living spaces is what they need. And then I think whoever does that’s going to be gobbled up pretty quick. know, Clayton homes is not going to stand by and be beaten by competition and taken out from a industry disruptor. They’re going to just suck it up, I think, and then do it or something.

Dylan Silver (23:36.326)
Yeah, you’re exactly right.

Dylan Silver (23:55.836)
I agree, Chad, we are coming up on time here. Where can folks go to get ahold of you?

Chad Freeman (24:01.166)
Right now the best website is brightharborhomes.com if you want to… Well actually my direct number… I’ll give out my Google voice. It’s 702-706-6904 Never mind the weird Vegas area code. You can also get me at Chad at brightharborhomes.com

for single family stuff or if you’re looking for mobile home park stuff hit me up at chat at MHP like mobile home park buyers dot net.

Dylan Silver (24:33.038)
Thank you so much for coming on.

Chad Freeman (24:35.224)
Yeah, thanks for having me. It was nice.