How a Golf Pro Built an 11-Unit Rental Portfolio From Scratch

John Story (00:00)
little backstory when i first got that first duplex that i bought if you showed up with cash for the rent and first month deposit i just let you in man you know all of have a thousand dollars cash in your hand that’s kind of nice right now you can walk up to me today with a thousand dollars cash and three months of rent and you’re not getting in so i run a background check

And that’s a way better system than what I started. So you learn as you go. And I’ve learned a lot over 20 years.

Dylan Silver (01:55)
Hey folks, welcome back to the show. Today’s guest is a lifelong Nebraska native, runs a golf course, loves golf, and invests in long-term rentals, including several duplexes, flips, and an 11-unit property. Please welcome John Story. John, welcome to the show.

John Story (02:15)
Alright, thanks for having me.

Dylan Silver (02:16)
I always like to start off at the top, Jon, by asking folks how they got into the real estate space.

John Story (02:23)
I was working the golf course and take care of that and so I time in the winter up here because it snows and so in the winter I would start buying a house, buy a house and fix it up and run it and I just did that several probably half a dozen winters in a row and build up some some equity and then started flipping a few and just kind of progressed from there.

Dylan Silver (02:42)
Do you have family or friends or connections that were involved in the real estate space or how did you say, hey, this is a path that I want to invest time and energy into?

John Story (02:53)
you know i’ve been interested in real estate forever and a day. My brother is actually a real estate agent in Omaha but he’s definitely more of the residential type of you know not much on the commercial side or the rental side but I just always had a life in real estate. I really thought maybe I ended up doing something around that when I got out of college and here I am doing some other things instead but it’s worked out well I enjoy it.

Dylan Silver (03:06)
Yeah.

I always tell people this anecdote of I’m a newly licensed agent in Dallas. I got licensed in April or thereabouts of this year. But for two years prior to that, since 2023, I’d been working with investors as a wholesaler and just networking in that community. And I kind of thought in my head like, well, everyone who’s in the real estate space must understand real estate investing because doesn’t everyone think the same? And no, not at all. I showed up to real estate classes and I was like the only one.

who was even remotely interested in like distressed real estate and foreclosures and pre-foreclosures and working with, in fact, I tell this to people and I’m a real estate agent myself, so of course I am maybe biased in both directions if you can be, but so many people said, man, investors are like, they’re gonna make low offers and this type of thing, and I was thinking, wow, I am that guy, I was the guy making the low offer, so it is kind of two different worlds, right?

John Story (04:09)
Yeah.

for sure I sent letters I did that whole nine yards sent letters out and I still do once in a while ⁓ I sent a letter to a guy on one of my first flips and he’s giving to his neighbor who wanted to sell so I mean he just it worked out great I got when I sent out like ten letters and got a property which is highly unusual usually takes hundreds but ⁓ yeah there’s I’ve been down a lot of those paths and I just like I’m ready to get something larger bigger more scalable

Dylan Silver (04:42)
Did you know from that first deal that you did, you mentioned kind of

every other year looking at deals that, I’m going to build up a portfolio over time. Or was that first deal kind of just getting your feet wet and seeing what the game was like?

John Story (04:57)
i’d say a little bit of both

know that i like uh… the retirement part of it i mean my my my thought at that time was by five or six or ten of these things and haven’t paid off in twenty years and just have that for retirement and able to travel and do those kind of things uh… and then i end up flipping some houses i said buying a couple of you know larger unit ones and uh… just kind of steamrolled from there where i’m at now it just kind of settled in and i’d rather i’m just looking to like i said scale up and get

get a bigger, get a larger, meet some new people and move forward with some larger units.

Dylan Silver (06:19)
And

you’re involved in multifamily, right? You have an 11 unit deal. We were talking before the podcast, you’re a converted hospital and you’ve got duplexes, triplexes. sounds like you’re involved in some flips, right? When you were going initially to where you are today, was the game plan always to scale and have acquisitions that were going to be larger units or was that kind of a progression with time?

John Story (06:30)
Unite unit.

I’d say it’s a progression. think I started out with Duplex. Like I said, I do have the eight and the 11, and was kind of large as I went. I don’t think I really understood the, I think I was afraid, I won’t say afraid, but nervous about trying to raise capital, raise funds, other people’s money, you know? And that was probably the biggest thing, at least hurdle in my brain, that, you how am going to go ask XYZ for $300,000 to put toward this apartment deal? And so I finally got past that hurdle there a while back and trying to move forward that way.

Dylan Silver (07:17)
I’ve had a lot of people on this show, John, a lot of folks who are in the capital raising space, specifically capital raising on Wall Street. And I kind of thought, well, that’s a totally different world. ⁓ But as we’re seeing, there’s more and more private equity going into just business acquisition and real estate is among among those. And so the advice and the feedback that was given to me, take it or leave it right was everybody should know what it is that you’re doing.

And if you’re raising capital, everybody should know that you’re raising capital. And I had a kind of similar thought. was like, well, I’m looking at land deals or maybe an RV park or maybe modular homes because I’m in North Texas. So you’ve got a lot of land over here. And who’s going to want to invest in that? Right. And it turns out there’s lots of people and I’m sure you have the same experience. Lots of people who maybe are sitting on.

some money, maybe have some savings, but they don’t have the real estate knowledge. They can’t go spend time sourcing the deals, talking to people and so on and so forth. And you know, that’s that’s how kind of teamwork and capital gets raised, right?

John Story (08:24)
Absolutely, That’s probably what I lack more than anything, a bunch of big team. I got construction background, I’ve been the guy on my rentals, I’ll change out a water heater, put a new… ⁓

flushing on the toilet, you know, whatever, just basics, you know, hang a drywall. did a lot. That’s how I got a lot of that was through sweat equity back when I was younger. And that’s kind how I built up my portfolio that way. So yeah, getting those people that can scale up and want to do that is exactly what I need for sure.

Dylan Silver (08:56)
Did you grow up working as a contractor on houses?

John Story (09:00)
No, just self taught mostly. Well, I did build my own house when I was not entirely in frame, but I did most of work of my own house, the tile, the drywall, the you name it. did paint it, everything we did everything that we could.

Dylan Silver (09:14)
I tell people

this, I’ve done a couple demo jobs and working for a flipper out here in DFW and nothing will teach you more about what can go right and what can go wrong than demoing a home. Cause you’ll take out the walls and you’ll see there’s mold and you’ll look at underneath the subfloor and now there’s giant issues with the foundation. And then there’s all different types of things. And then you start to see, well, this decade,

has these issues and this decade has these wiring issues and I’ve got to, you I know that if I am doing homes in this decade that I’m going to be comfortable with it because I’ve seen this type of home or I’m only going to look at, you know, brick homes and so on and so forth. And I think it behooves all people who are starting out to do, least do a couple of those, right?

John Story (10:39)
sure so people get their feet wet. and if you’re young, a lot of younger people don’t have necessarily the funds or the know how to go do that, but they can, they can figure out how to hang a piece of drywall, figure out how to fix a toilet or whatever. You know, my issue is now I got to where, why pay somebody 800 bucks or put a hot water in when I can do it myself, you know, an hour and a half. So that’s a really hard mindset thing for me to come over, to get over. So that was, that’s one of my biggest hurdles also, which I’m getting a lot better at delegating and hiring.

Dylan Silver (11:02)
Yeah.

That’s one of the things people talk about a lot on this show is this idea of especially right now with AI which seems to be so big in real estate. I’m a software engineering student outside of this and there’s almost more AI, John, in real estate than there is in software engineering. If you believe that, it’s hard to believe. But one of the things that I’ve seen is people are really focusing their kind of mental bandwidth on

John Story (11:28)
It’s

Dylan Silver (11:36)
highest level tasks, the ones that require the greatest degree of problem solving, and the tasks that will really push their business forward, both creatively, and then also maybe expanding into new areas. ⁓ And I think about that, you know, in my business and things that I’ve been able to delegate to AI and not have to worry about ⁓ things as simple as like cash flow and budgeting and not having to figure out and write a whole new budget each time I have a new expense, it’s

It’s nice to be able to do that. But I want to pivot a bit here, John, and ask you about this 11 unit deal. Maybe let’s get a little bit granular, but don’t give away all the gold. So 11 units, that’s kind of an odd number of units, right? It’s not a three, four, or five. We’re talking about 11. And how’d you find this deal, and what was the process like?

John Story (12:21)
right.

actually i was one of my brother and camera crossing as you probably like that and said well maybe so we went and looked and i’m buying it need a little work to get going that’s kind of my in my my deal the whole time isn’t do a little work to it and buy a little cheaper do a little work may work more money and then you know seller keep it or refinance it or just you know depending on the deal obviously that’s how we did it and i bought it and started working on it and started renting some out and that’s where we’re at today with it

Dylan Silver (12:54)
And so you’re in the long-term space. I know that there’s so many different plays that people can look at. A lot of guests on this show are long-term. We have a lot of people in short-term, and I’ve had a couple people in corporate housing mid-term. What, for you, makes you ⁓ gel most with the long-term space? Or what do you like best about long-term versus some of the other verticals that people can look at?

John Story (13:16)
I would love to do vacation rentals. always thought that would be a great thing to do, the short-term kind of stuff. My problem with it is I don’t… I don’t know everything I probably need to know about it for starters, but also I was always nervous about one or two bad reviews for something that out of your concealer goes wrong and then it slams your rating and then…

Dylan Silver (13:34)
Yeah.

Then you’re done.

John Story (13:39)
yet that’s not good so so that was maybe a little nervous now i got this property knowing what’s around it because they said i’m a i’m a bad guy on on the review so that’s that’s been makes me nervous

Dylan Silver (13:48)
I know you got to do everything.

I want to ask you, with the long term rentals, I can say definitely out here in DFW, and I’m an East Coast guy at heart, right? Grew up in New Jersey, Northern New Jersey. The renters are probably the most important. So sometimes people will rush people in so that they can get it occupied, but that can be a big mistake, ⁓ especially with how things can go, right? And you’ve had now so many…

so many tenants you mentioned an 11 unit duplexes, triplexes, so on and so forth. What’s been your key to finding good tenants?

John Story (14:23)
well

little backstory when i first got that first duplex that i bought if you showed up with cash for the rent and first month deposit i just let you in man you know all of have a thousand dollars cash in your hand that’s kind of nice right now you can walk up to me today with a thousand dollars cash and three months of rent and you’re not getting in so i run a background check

and

all that jazz. I’ve got an online application that they can fill out and submit. call references. We do a background check. We do the whole nine yards.

But yeah, at the very beginning, was probably really dumb looking back at it. And it’s crazy. People hand you cash and don’t even want a receipt, which I find amazing.

Dylan Silver (15:43)
I know.

What’s the climate out there like for rentals? mean, is the eviction process quicker or is it a very long drawn out process if you have to go down that route?

John Story (15:58)
It’s not horrible. You got a notice to quit like everything else and then you got… I’ve done two in 20 years. I just used the lawyer. We post the notice. Sheriff gives them the letter. Then they got to set up a day. So it takes anywhere from I’d say 45 to 90 days. Usually it’s not quite that bad, but it just depends. If the court system is really busy with other stuff.

Dylan Silver (16:22)
Yeah, that’s not too bad at all. was talking with a real estate attorney in Seattle, and we were talking about Seattle, Washington, real estate pricing out there, and why is it so expensive? And he’s like, well, one of the reasons why rents and everything is so expensive is because investors have to be prepared that if they have to evict somebody, it’s going to take maybe a year. So they might not be.

Receiving rents for a very long period of time and that’s why the the renter are so high But Nebraska is an interesting area right because we were talking about you know the average price of the homes out there And how people may be from other areas might be looking at some other areas of the country. I’m in Texas We got a lot of investors in Texas, Florida, right? I just had a guest from ⁓ North Carolina and I’ve had guests from Virginia Virginia Beach and so a lot of people may be going to these areas I wouldn’t be shocked if

Already we’re going to start to see more people investing from out of state in Nebraska, right? Especially with those prices, right?

John Story (17:20)
⁓ yeah i mean that it’s affordable but but it’s it’s it’s all relative to in places you know the rest of you may you might get i’m gonna say twenty two hundred dollars for a really nice house or whatever in phoenix or dallas or wherever but you may only get fourteen or fifteen or sixteen hundred here so it’s it’s it’s relatively you know based on the purchase price to the market ⁓ that it is a correlation there is it sometimes it better sometimes it’s worse just depends on the situation

Dylan Silver (17:47)
I want to pivot a bit here and talk golf, because I’m not a golf guy. I’ve tried it. It’s a very difficult sport. You’re a lifelong golf guy. And I believe you’re also involved in coaching. Is that right?

John Story (18:00)
I’ve been coaching the high school team for about 20 years.

Dylan Silver (18:03)
Very difficult sport. I grew up playing tennis, which is up there as far as mentally exhausting, tricky sports. ⁓ And we were talking a little bit beforehand. I was saying, well, everyone is no longer playing tennis and they’re moving to pickleball. What’s the reception like for golf? Is there a lot of young people taking up golf, you think?

John Story (18:24)
seems to be COVID really was a game changer for golf. I people couldn’t go anywhere, you know, you can go outside, do things. That seemed to help the whole golfing industry as a whole. I think you’d find that in most markets. We seem to, in our area at least, we have quite a few, you know, younger people playing. It’s a wide array of everybody if you think about the local membership and that kind of thing, but there are definitely more younger people playing than there used to be.

Dylan Silver (18:52)
It’s a tough sport, my, it’s one of these, and I say the same thing about tennis, it’s like, you can’t take six months off from these sports and then just go back in unless you’ve played your whole life. It is, it’s a brutal sport, it’s not forgiving. It’s you against you, right? ⁓ And ⁓ top golf is what everyone goes to play. What’s your opinion of, I know a lot of golf guys don’t like top golf. I love top golf, but what’s your opinion of, you know, top golf?

John Story (19:17)
it’s fine, it’s fun. I do it once, I’ve done it few times, but I mean it’s not real golf, but it’s, you go with your buddies or whatever and have a good time, it’s awesome, I don’t have any problem with that. The thing I like about golf, it’s me against the course, you know, and if I make a bad shot or bad decision, whatever, I can’t blame anybody else but me, you know, and so I kinda like that, it’s very, it’s rewarding and I enjoy it and I’m semi-decent at it, so it’s fun, I enjoy it.

Dylan Silver (19:44)
Favorite golfer or maybe top or favorite golfers to watch.

John Story (19:49)
anymore i don’t watch a lot of anymore i used to love greg norman back in the day i grew up with him you know uh… phil mickelson tiger woods some of those guys are more my age uh… new new guys scotty shepard’s pretty good if anybody likes golf uh… he’s from for a reason i watch a little majors but i don’t spend a ton of time watching golf anymore it’s a fun one i do

Dylan Silver (20:00)
Yeah.

It’s a

it’s one of those it’s one of those things you got to be I have so much admiration for golfers because I know how difficult it is ⁓ to be involved to be involved in golf. think there may be some similarities there if we if we really look at it between the real estate game and golf. Definitely a lot of land, right? You need a lot of land for both. ⁓ But John, we are coming up on time here. Where can folks go if they’d maybe like to reach out to you or if they’re interested in

John Story (20:30)
For sure.

Dylan Silver (20:38)
you know, learn a little bit more about your business.

John Story (20:41)
yeah we’ve got i’ve got a website it’s dearfield holdings l l c dot com i’ve also feel free to give me a call if if you’d like to connect and maybe work on some larger projects are just get to know you someone you can call me direct it’s four two four six nine ⁓ seventy two sixty two

uh… i get a lot of calls may not answer if you just leave a message i would be more than happy to call you back but do you get a lot of spam calls too yes the best way to do it and uh… your field hollings is on instagram and facebook as well i’m kind of an old dog trying to learn the social media trick and uh… takes a little bit of going on but i’m getting a little better at it

Dylan Silver (21:24)
John, thank you so much for coming on the show here today and look forward to seeing some more deals up there in Nebraska, right?

John Story (21:33)
Absolutely, I appreciate you having me on. Been a very good time talking to you and I enjoy that. Thank you.