Mastering Real Estate: Jason Chrisman’s Essential Tips for Aspiring Investors

Dylan Silver (00:00.961)
Hey folks, welcome back to the show. I’m your host, Dylan Silver, and today on the show I have real estate entrepreneur, Jason Chrisman. Jason, welcome to the show.

Jason Chrisman (00:13.218)
Dylan, thank you so much for having me. I’m excited to be on your show. I love your podcast and I’m ready to do this.

Dylan Silver (00:18.691)
Let’s do it. I always like to start off at the top by asking folks, you know, how did you get into the real estate space?

Jason Chrisman (00:25.134)
You know, it’s actually quite a funny story. I wanted to get into it about 13 years ago, but I got into it about 10 years ago. My father and my mother were in real estate. My mother owned a real estate here in New York. My dad, he was a flipper, but one property at a time, one property a year, never took it past that because he was worried about being over leveraged. So I learned a little bit from them. And when I was ready to do it, you know, I had a lot of negativity in my ear saying, don’t do it. You’re not going to make money. You’re in, you know, you’re risking everything in your bank account. And I listened.

I listened for three years. Finally, I stopped listening to people. took the chance. I bought my first duplex here in New York. Talked to me about $65,000 down, but I didn’t use my money. I took on a partner. My second duplex, I used my own money. And then from there on, that’s the story. I got started pretty much because the negativity, I was tired of hearing it. And I knew that I could make money in something like real estate. And I was right.

Dylan Silver (01:18.969)
Where are you from in New York? I’m from Northern New Jersey.

Jason Chrisman (01:21.75)
I’m from Long Island, New York in a town called Patchogue.

Dylan Silver (01:25.093)
Look at this, look at this. tell people when I’m in Texas now, I’m in Dallas, Texas, but in Northern New Jersey, we’ve got this kind of tri-state area, Pennsylvania, New Jersey, New York, like a competition, if you will. You come down to Texas and it’s like, my gosh, there’s someone from the East Coast over here. It’s like, we’re all at Simpatico over here. So it’s good to be talking to someone from that, neck of the woods. When I think about real estate investing in that area, it’s not quite the same as it is out here.

Jason Chrisman (01:40.946)
Hahaha!

Dylan Silver (01:54.409)
You mentioned getting in and the duplexes, which I think a lot of people would say that’s a great way to get in. Did you have mentorship when you were getting in? You mentioned your parents are in the business. How did those first deals come about?

Jason Chrisman (02:04.354)
Yeah, no, and I’ll tell you why. My parents were in the business when I was younger, but they haven’t been. My mother passed about 20 years ago, so I haven’t had her. My father stopped buying real estate, stopped flipping real estate about 15 years ago. So I initially learned a little bit from them, but I learned by trial and error. I didn’t have mentorship. I didn’t have anybody guiding me. I made mistakes. I lost money. I made money. Really the best way, in my opinion, to learn is kind of just to jump in and figure it out as you go.

if you don’t have mentorship, if you don’t have guidance. So that’s the route that I did take it. I had no mentorship, very little bit of money to start, but I got there.

Dylan Silver (02:41.879)
Yeah. That first deal. Do you remember that first deal? Walk us through that first deal. How did you find it on market, off market? What was the funding from?

Jason Chrisman (02:45.559)
Of course.

Jason Chrisman (02:50.83)
So yeah, it was a duplex on market. It was in turnkey, but not really brought up to today’s conditions. So the down payment on the property was about 60 grand, 68 grand actually, $350,000 purchase on that property immediately. And this is a while back. This is years later. Now it would cost 700,000 easily 800,000. So, I’ll tell you a story about that a little bit later as we go, when I sold them here in New York and the bank roll that I made, but I bought the property. said, all right, I’m not going to dump any money into it.

Dylan Silver (03:03.053)
Yeah.

Dylan Silver (03:08.407)
Yeah.

Jason Chrisman (03:20.066)
I’m going to take on a partner, which I did. It was a relative, somebody in my family. They put up the money. I ran the property. I got two great tenants in there. I let the property sit for two months because I wanted the best tenants. You know, I always hear these nightmares. You get the wrong people in. It takes a year to get them out in New York. So I focused on tenants, not really building the property up more. And I got great tenants after year one. I raised them 150 bucks a year. Like clockwork. went with the market conditions. the first property wasn’t horrible.

Dylan Silver (03:32.483)
Good call.

Jason Chrisman (03:48.322)
The third property is what made me really think, okay, should I be a real estate investor or not? And that comes with the struggle and we’ll get to the third property in just a minute. But the first property honestly wasn’t anything hectic. wasn’t anything crazy. I bought it, maybe paint carpets and that’s it. We threw tenants in within two months, started cash flowing about 850 bucks a month on the duplex. We did well. Yes. Yes.

Dylan Silver (04:09.581)
Was this in Long Island? So when you were finding that deal, was it like, hey, let me make a bunch of offers and let me see what I can get? Or was it, you specifically like this property?

Jason Chrisman (04:19.31)
Yes. No, I think at that time I probably had about five to seven offers at on that time, but that was probably my 15th offer total. I put a lot of offers in a lot of different places and the funny thing is two of my offers were accepted within maybe 24, 36 hours of each other, but I ended up taking this property and I’m really glad that I did. Years later that area blew up. That price of that property doubled. I sold those two duplexes in that area which were a few blocks from each other.

for double of what I paid for them within like five years.

Dylan Silver (04:50.583)
So 850 cash flow a month and doubling in five years. Those are some pretty big W’s there, Jason.

Jason Chrisman (04:55.438)
Yeah, yeah, they were. Yeah.

Dylan Silver (04:59.349)
So, you know, when we think about these kind of beginning steps, I want to get granular. Now, don’t give away all the gold, but I am going to ask some specific questions here. So maybe save some, but you had a bunch of offers out. You got two accepted. So are you then having to put up EMD and option money on two different properties at that point?

Jason Chrisman (05:08.408)
Sure.

Jason Chrisman (05:19.83)
No, no, I never do EMD, even now I don’t do EMD. My negotiation tactic now is to come in with cash or I’ll come in with a 70 30 or I’ll come in with a loan. But EMD is not really something I throw down on the properties because we will put out so many offers and so many different properties. And it’s not like we’re limited. You know, we’re not really in a huge demand market where real estate isn’t, you for sale. There is an abundance of real estate out right now. Back then, there was still a lot of real estate out.

We haven’t really switched the conditions much, but I would say the biggest thing that made me choose that property is property location. I knew that area was gonna be something about a half a mile away. Properties were going up 20, 30 % within months. So I knew eventually it would hit there. And do you ever know for sure? No, but it was an educated decision and I ended up being right. Just two duplexes that we sold, made, we walked away with half a million dollars cash.

Dylan Silver (06:14.113)
I want to dig into the no EMD. So this is kind of counterculture against the grain. I’m a real estate agent, new real estate agent in Dallas. I’m a wholesaler. really more passionate right now, at least about the wholesale portion of it. whenever I’m talking with realtors, they say, you can’t. You have to do the EMD. How is anyone going to take your offer seriously? Did you get any of that pushback? And what did you do to combat that?

Jason Chrisman (06:35.022)
100 % everybody wanted 1 % down at the absolute minimum. I said no to combat that I came in with good terms. My terms were a very fast closing which is important and a short due diligence period. Most people looking at a property depending on the size they want 14-15 days due diligence. Give me 7-8 days so I’ll cut that in half. I’ll buy the property as is meaning I’m not going to come back and bite you. Oh want a seller’s concession or a buyer’s credit for $30,000. I’m not going to do that. This is the price I’m willing to pay. This is

is know what you said is wrong with the property and if I go on the property and I see that’s the condition of the property they told me what it is I’m not going to negotiate I’m not going to give them a problem I show them proof of funds which is more than enough to buy the properties I show them credit I show them everything they need to see as well as HUD statements if they want to see I own properties in those areas so I’m showing them basically experience and money so in a way we’re kind of flashing a little bit say look we could buy this property ten times over just with the account we’re showing you

This is why we need that this price. This is why we’re not putting down EMD, but we’re willing to close very fast We’re gonna buy it as is and I’ll even split your agents commission with the agents commission fee with them as well So it depends on the deal. Everything’s gonna be different I think out of every property I’ve ever purchased which is probably in the high 70 low 80 range I probably put down EMD on maybe 10 of them in my life

Dylan Silver (07:57.613)
That first property that really, you know, you have to be a little bit of a different strategy, right? Because you didn’t have the HUD statements, right? Was it more of a you’re having to do more communications with the realtor or the seller to kind of do more cajoling and convincing?

Jason Chrisman (08:02.67)
Yeah. Yeah. Yeah.

Jason Chrisman (08:12.334)
I think they liked the fact that the person that was going on with me and putting up the money was much older, my partner at the time, the investor. So they liked that. They did like that. And plus we paid over asking. We only paid 10,000 over asking, but we knew this property was it. And we knew we would do well. We ran the numbers. Our COCR was great. Our cashflow was great. Our upfront cost wasn’t bad. You know, we did very well on that property and I knew we were going to, so we were willing to overpay a little bit. Five, $10,000, fine. Never any more than that.

Dylan Silver (08:17.889)
Okay. Yeah.

Dylan Silver (08:23.566)
Huh.

Dylan Silver (08:41.771)
So, you know, community is something that’s important to you. We’ll hop into that in a bit. You mentioned you were with a partner on this first deal. How did you find that partner? Relative. How did you convince a family member? That’s the hardest people to convince.

Jason Chrisman (08:51.436)
relative, family member. Family member.

I, you know, to be honest, I didn’t, they convinced me, they told me to cut out all the noise, stop listening to other people. If you want to buy real estate, you want to become a real estate investor, just do it. Worst case scenario, you lose some money. Real estate’s not going to go from, you know, the purchase price, 350,000 down to zero. I’m not going to lose my shirt off my back. We all know that real estate’s going to go up eventually. You only lose when you sell. So I knew that. And then the person said, look, why don’t I put up the money, you run the property and we’ll take it from there. I said, perfect. So they put up the money on that property.

Dylan Silver (09:14.073)
Yeah.

Jason Chrisman (09:26.672)
Shortly after, three months after, I put my money on another duplex and I just kept going from there. But I didn’t have to pay the

Dylan Silver (09:31.737)
Were they a real estate guy or gal? Were they in the real estate space or were they unrelated?

Jason Chrisman (09:35.468)
No, no, no. In the health industry, and they make very good money. yeah.

Dylan Silver (09:41.613)
Yeah, that’s king.

Jason Chrisman (09:43.406)
I told them the return on the money. Look, they made the first year $425 a month, you know, and they liked that. They’re like, oh great. It’s like me working a day. I have a day off, you know? And then eventually it came to the point where when I sold the property, we cashed out that property made like, I want to say 330,000 when we sold. So they got an additional like what? $165,000 for their measly investment of 65,000. And they got, they got five years of, of cashflow, which eventually was like,

Dylan Silver (10:05.047)
Yeah, they weren’t springing a hammer.

Jason Chrisman (10:10.414)
I believe they were getting like 675 a month just for half of it. Cashflow by year five. It was a good investment. It was smart. 100%.

Dylan Silver (10:14.275)
Yeah. Not. It was a great investment. You know, when I when I think of starting out, I think a lot of people say, well, I don’t have the money, right? Or if I don’t have the knowledge, I think you got to have one or the other, right? So you had the knowledge, right? You partnered. If folks are just starting out, and maybe they’re looking for capital, what would be your advice to them to find a capital partner?

Jason Chrisman (10:35.968)
If I could start all over, I would do it extremely different. So the way that I teach people to get into real estate is many different methods. We use six different buying methods, right? This is exactly what I would tell them. Open yourself up to as many buying methods as you can. If you don’t have good credit, we know you can’t use banks, right? If you don’t have W-2 statements, but you have good credit, you could use DSCR lenders, but then you need the down payment. If you want to go on terms, you can get into a property with a little bit out of pocket, or private money or hard money is probably one of the best ways to get in alongside of house hacking.

of people are not willing to sacrifice one year to buy like a duplex, triplex or quadruplex, live in a portion of it after a year.

rent out the whole entire thing. mean, you’re living, most of my students who house act are living absolutely for free and they’re getting paid to live there for free after a year rented out. Now you’re making, you know, 50 % COCR, 60 % you can’t lose. So what I would say to people is use as many buying methods and strategies as you possibly can and learn this one thing more than anything else. Leverage. Leverage is key.

Dylan Silver (11:29.163)
You can’t.

Jason Chrisman (11:39.562)
Once you learn how to take something, could be the biggest POS, add value to it. That value can come from a renovation or it can come from raising the market rents. Once you’re able to do that, you are pushing and grinding in all this equity.

You know, we bought a 36 unit for 1.6 million, put 150 into it, now it’s worth like 2.4 million. You know, once we refinance out, it’s free property that’s gonna pay me cash flow every month. And remember guys, this is important, and girls, real estate cash flow is a very small part of what you’re getting. Cash flow, appreciation, depreciation, tenants pay down on your mortgage after 20 years, that’s a completely free property, do with it what you want, and the tax incentives are gold.

five different ways you get paid in real estate. So I’ll ask you as a, whoever’s watching this as podcast members, would you take a hundred dollar cashflow? Let me ask you that question, Dylan. I’m not going to give you any other information. Would you take it?

Dylan Silver (12:36.153)
Yeah.

$100 cash flow? Absolutely.

Jason Chrisman (12:41.356)
Sure, now the smart thing that Dylan just said was he said, sure, absolutely. The one thing he didn’t go at was no. Most people say no, but here’s the entry guys. We’ve gotten into properties for $2,000 out of pocket. If it costs me two grand to get into a property, I’m only making $100 cashflow a month. That’s still what, like a 65 % cash on cash return? I win. Show me somebody else who’s making that money. That’s year one. Year two will be even better. Year three, year four, year five.

Real estate is a game of patience and holding and forced equity and leverage. Learn those things, you will change your life guaranteed.

Dylan Silver (13:17.389)
You mentioned earlier, Jason, raising the rents, raising the rents. And lot of people don’t know how to do this, right? You have found good tenants and then you would come in and raise the rents maybe year to year every other year. Walk us through that. Well, how do you raise rents without them leaving?

Jason Chrisman (13:20.654)
Hmm?

Jason Chrisman (13:24.514)
Yeah. Yeah.

Jason Chrisman (13:30.115)
Yeah.

Jason Chrisman (13:33.902)
I’m very good at that. So we’re good at buying a building, whether it’s a smaller quadriplex or 20, 30, 40, 50 unit and hitting everybody with a $50 rent rental raise increase on average 80, 85 % of people are going to accept it and stay, or they’re going to argue it. And then we’ll give them a three month to a six month grace period, then start paying it. You’ll lose a small amount, but that rental raise increase is going to keep me exactly where I was making with 15 % of people leaving. And then we just replaced those 15 % of people to do that. You have to give to get now.

Now lot of properties that we buy are they need some renovations or rehab, they’re under market rents. It’s not necessarily, and I hate to say this, it might make me look a certain way, it’s not necessarily our issue that the landlord that they had, the owner of that property was charging them $700 when you could be getting $900. You got a break for years. I can’t dish that break out to you consistently. I’m not a monster. I will help tenants out. I’ve given tenants free months, single mothers, single fathers.

as as I possibly can, but at the end of the day, it’s a business and in order for your business to sustain and to grow.

You have to push your limits and your boundaries. Now my limits and boundaries are not the market rents are 900, I need 950. The market rents are 900, I need to be within $50 of that number. I’m not looking to slam everybody out. And if somebody wants to leave, that’s okay. I’m not gonna say you gotta get out now. You wanna stay another six months, I’ll let you keep your rental rate for three months. Six months, it depends on what time of the year it is. I don’t push people out in the cold. So we work neck and neck. Here’s another part a lot of people don’t understand.

I don’t need to buy a two, three, four, $500,000 property to make great money. I buy 60 to $80,000 properties. Now, even with a bank and a DSCR loan, which is only looking at my credit, no taxes, no W-2s, they don’t care what I have in my bank account, as long as I can hit escrow at 20%.

Jason Chrisman (15:26.798)
Just by doing that guys, you can get a property for like 13 to 15 thousand out of pocket. I throw section eight tenants in there. If I was to rent out majority of my properties, I’d probably get like anywhere from 750 to 900. But because there’s section eight tenants, which are housing authority, I’m getting like 1100 to 1400. So it’s a giant difference. And that’s what I mean by raising rents. I give and I take. So I’m not going to buy a building that needs work and then boost everybody’s rents up. No, I’m to make your bathrooms look better, your kitchen look better.

sidewalks, not be so craggy and you know, I’m going to make the place look a little bit better. So I’ve learned if you give, you can definitely take back. So it’s important to do that.

Dylan Silver (16:07.641)
100%. You mentioned a couple topics there. From raising rents to working with tenants, you mentioned like at any point in time, it’s not going to be less than 80 85 % occupancy. So it’s not like raising rents is causing this this

Jason Chrisman (16:11.148)
Yeah.

Jason Chrisman (16:14.446)
Sure.

Dylan Silver (16:23.769)
enormous pitfall either. You know I think a lot of people look at real estate and think you know how do I get in or this is how the other people not me. I was kind of one of those people. I saw my rents getting raised. I was living in San Antonio Texas. I lived in a nice area and I saw everything. said well I got two pools. have two gyms where I’m living at. It’s kind of a nice area but it was expensive.

Jason Chrisman (16:34.988)
Yeah.

Dylan Silver (16:47.737)
And I said, well, it’s not like it’s getting any cheaper. If I can’t beat them, join them. And that’s when I became a wholesaler. And I think you probably share some of this, Jason, is I’m passionate about helping as many people humanly possible, maybe even to a fault, to get into the real estate space. Because I want every American, every American, to feel like they can be a real estate entrepreneur.

Jason Chrisman (17:10.28)
and you can and they should. People don’t realize being a W-2 employee, you’re nine to five, whatever hours you’re working, what one property will do for your taxes. It’ll make a giant difference. If you’re paying 30 grand a year in taxes, you have a property, you can write off that, but know, Jason Dillon, I’m making money on that property. The government doesn’t care if you’re making money.

you get 100 % depreciation on any asset that you’re renting out. So if you buy, let’s just say $100,000 property, you have 27.5 years to depreciate that property. You could do it a lot sooner if you wanted to. Let’s say one year, I gotta pay half a million dollars. I could depreciate five assets and get rid of that in a heartbeat. But the point is $100,000, 27.5 years, that’s what? $333 a month? I’m writing off just on depreciation alone.

Dylan Silver (17:56.387)
Yeah.

Jason Chrisman (17:59.752)
you to buy houses to rent to people because they can’t do it. So those tax incentives are beautiful. Take advantage of them.

Dylan Silver (18:06.563)
You know, I think a lot of people I was one of these people, I couldn’t believe that this was kind of a real thing. Like I’m a W to I work for a company. And then I open a real estate business, you know, I’m renting out right. And somehow I’m getting more money from my job. That doesn’t mean yes, you are you’re actually literally getting you’re able to deduct against that. I’m not a tax strategist. So please talk with the tax strategist but

Jason Chrisman (18:14.67)
Sure.

Jason Chrisman (18:22.52)
Hmm?

Jason Chrisman (18:29.322)
Sure, sure.

Dylan Silver (18:30.519)
You know, you know, another thing I learned is a CPA is not a tax strategist. The CPA is not an enrolled agent. So CPA, you know, a lot of the big companies you go there, they’re not like a fiduciary responsibility to you to save you the most money. You may end up paying money, right?

Jason Chrisman (18:45.624)
Sure.

Dylan Silver (18:46.477)
But then you go to an enrolled, completely different thing. to your point, if you get into real estate and you have the W-2, you’ll actually pay, that sounds crazy, you’ll pay less in taxes on your W-2 because you’ll get it back at the end of the year.

Jason Chrisman (18:58.466)
Yep. Yep. Yep. And you want to hear something even crazier? I don’t pay taxes. I made $450,000 last year. I don’t pay taxes. I literally paid $1,000 last year. That’s because I got lazy and I don’t want to go back and change the answer. The way that you can do this is stop paying yourself. Okay? I own multiple businesses. I have my hands in different things. I don’t take money from real estate for the last probably three or four years now. I just keep dumping it back in, dumping, dumping, dumping. I want to set my children’s children, children up.

for success forever. So what we do is instead of paying ourselves, which is not smart, you want to borrow money to pay yourself. So let’s say I have $15 million in real estate, right? I have $8 million in loans, $7 million in equity. A bank will easily give me a credit line for half a million, million dollars. No problem. I have a few of them out right now. I’ll take a credit line, an open-ended credit line for 500,000. If I need to pay myself 300,000 a year, that credit line will go to pay me and my business will pay that credit line back.

every single month. So instead of my business paying me, they’re paying the credit line. I just saved like 18 to 24 % a month, a month, just in employment taxes alone. And there’s many other strategies that you guys can use to save money on taxes. I’m not going to let it all go here for free, but if you want to see it, you guys will find out where to find me at the end of this.

Dylan Silver (20:17.183)
I speaking of the end of this we actually are coming up on time here Jason but I do want to give you opportunity to talk about the community that you have and then where folks can go to get a hold of you.

Jason Chrisman (20:27.406)
Sure. So our community is a little bit different than anybody else’s. We have such a family fuel, fuel, sorry. We have probably about 230, 240 people in our community. We leave our Zooms under 30 people. You know, you get into a community, you have 10,000 people there. You can’t speak. You can’t get heard. That hand holding doesn’t happen. We are completely different, completely across the board, five star reviews. We do fix and flips, buy and hold, section eight, novations. mean, wholesaling, you name it. We allow members to come in

our community, use our buyers, which we take a little bit of, I’ll be honest, but our community is only $25 a month, guys, and we’re gonna give you the first month for free. If you’re watching this podcast right now, use code REBOX, R-E-I-B-O-X. Go to www.rebox.com, put in code REBOX, and you will get the first month on us. And then all you have to lose is $25 a month, I promise you.

you will get 1000 times what you are paying. Our software alone is 120,000. We give it for free to every single member. What you will be learning is leverage, growth, how to use other people’s money, how to use six buying methods, and how to actually get started with a little bit, a lot, or nothing. We cater to the new investor, the rookie, the veteran. We cater a little bit to everybody. So come check us out. Even if you take the first month for free, we have nothing to lose.

We’ll see you there. Hopefully you come.

Dylan Silver (21:54.413)
Jason, thank you so much for coming on the show here today.

Jason Chrisman (21:57.966)
Sure, Dylan, thank you so much for having me. God bless, man.