Outgrowing the Real Estate Model That Built the Business | David Graber | Part 1

This episode isn’t about Airbnbs. It’s about what happens when a real estate model stops scaling.

In Part 1 of this conversation, David Graber - real estate operator behind Brandywine Grove - breaks down why wholesaling and flipping hit a ceiling, and what pushed him into ground-up construction instead.

This wasn’t a creativity play. It was a market and infrastructure problem.

We cover:

• Why buying deals became harder after market conditions changed
• How steady income became more important than deal velocity
• The infrastructure math behind building multiple units on one property
• The early decisions that protected long-term control

If you’re an operator navigating market cycles, capital limits, or scalability ceilings, this conversation will feel familiar.
This isn’t a highlight reel.
 It’s a practical breakdown of how real estate businesses actually evolve - under pressure, not in hindsight.

Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.

New episodes release Tuesdays and Fridays.

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Transcript

Dead-End Job → Obsession With Recurring Income

David Graber 0:00

So I was uh working um what I would consider a dead end job, just living paycheck to paycheck. Was like there's gotta be a different way, it's gotta be a better way. I just longed to have that steady income of just money while I sleep. I wanted to be in real estate, I knew that.

Reshma Vadlamudi 0:15

Any early risk that paid off for you?

David Graber 0:17

I guess kind of risked my my life savings of everything I had left. I have to make this work, or my life depends on it. Failure wasn't really an option, I was just gonna make it work, whatever it took.

Reshma Vadlamudi 0:27

What's your favorite design so far?

David Graber 0:29

Oh the bunker's by far the coolest thing I've ever built. My name is David Graber. Uh from Sugar Creek, Ohio. I was born and raised in this area, pretty much central Ohio. Um it it's we're kind of between three major cities: Pittsburgh, Cleveland, and Columbus. We're kind of dead in the middle of those three. Um, so yeah, that's kind of the area I'm from. I was born and raised here. This is all I know. I've always said I want to move to the mountains, and I've never done it. So I'm still here.

Reshma Vadlamudi 1:04

I heard you say that you were investing in other forms of real estate. And did you say you got started with wholesaling? Is that how you got started in real estate?

David Graber 1:13

Yeah, yeah.

Entry Point: Wholesaling, Early Opportunity Post-2008

David Graber 1:14

So I was uh working um what I would consider a dead-end job in my early 20s. I worked in construction in my teenage years and was just living paycheck to paycheck and uh was like there's gotta be a different way, it's gotta be a better way to, you know, I I I discovered that I had some entrepreneur blood in my in my DNA, I would say, and that was intriguing to me, and I wanted to try and start my own business or do my own thing somehow. Um, so I don't have to show up at work every day, right?

Reshma Vadlamudi 1:47

Yeah, yeah, yeah.

David Graber 1:49

So I got into real estate, it was just the crazy story um how I got into it, but it was pretty wild. And I look back now and I'm like almost almost like I don't know how I would redo that. It was just kind of everything kind of fell into place, you know?

Reshma Vadlamudi 2:07

Yeah, yeah. Okay. So how did how did this happen? Like, how did the Airbnbs happen for you from wholesaling into the Airbnbs?

David Graber 2:17

Yeah, so

Deal Economics: “I Got Paid Only When I Bought And Sold”

David Graber 2:18

I started out wholesaling, which is uh buying and selling real estate, and I liked it. It was a lot of fun. I had a ton of fun doing it. Um, I would say that when the real estate I started back probably like in 2011, uh 2012, 2011 or 2012, somewhere in the area. And uh back then, you know, we had just come out of 08, the housing crash. And so there was a lot of opportunity. There's a lot of people that were trying to sell, had to sell, and you could negotiate down. Um obviously it was a little harder to sell back then, but it was much easier to buy. And I always say that in in real estate, I I felt like I made my money when I bought the property. So depending on how good of a deal I could buy, is how much I made. So that got uh throughout

Market Shift: Why Buying Got Harder (Multiple Offers, Over Ask)

David Graber 3:10

the years, you know, fast forward to let's say when COVID hit, buying was hard because now realtors were listing stuff or people stuff was hitting the market, and there was multiple offers, you get people would offer over purchase price. And so it just got really frustrating for me as an investor when when it was so hard to buy. So I was like, man, I as a flip as a flipper, real estate flipper, um, I only got paid when I bought and sold something, right? And so I would buy something,

The Pivot: Rentals, Storage, Commercial… Then Short-Term Rentals

David Graber 3:45

get a good deal, sell it, and then I would not get paid again until I bought another one. So it was just a it's a great way to start in real estate. It really is. I don't regret doing it whatsoever. It got me my start, but I just longed to have that steady income of just money while I sleep, steady income. So I looked at rentals, long-term apartment complexes, uh, single

“I Already Had The Property”: Why STR Was The Best Fit

David Graber 4:10

families, um, storage facilities, just anyway. I I loved real estate. I wanted to be in real estate, I knew that. So I just looked at every different aspect of income from real estate. Commercial is a good one too. There's so many good ones. There's there really is. Um uh, but then I I looked at the short-term rental uh business and was like, man, I have the property for that. I could build some really cool luxury stays here um on the property I already had. Uh so yeah, it was just it was the one that that made the most sense for me. And I was like, well, let me try this. And then obviously it went a little crazy with it.

Reshma Vadlamudi 4:51

But yeah, yeah. And how did you like I know you were telling you were flipping the properties? So then how did you decide all of a sudden that you want to do the ground up construction?

Ground-Up Decision: Modern Rustic Experience Vs Dated Inventory

David Graber 5:03

Well, basically, I I looked at a lot of Airbnbs like people that were renting cabins versus like I was more looking at cabin rentals, is what I wanted to get into. And there was just a vast amount of log cabins available on the market that were built in 1990, and they were, you know, everything was yellow pine on the inside and very rustic, and that was cool. Um, in in when it was cool, but I feel like it's not as cool anymore. Uh not that I'm hating on log cabins, I'm just saying it you're just so limited design-wise, what you can do with a log cabin. I actually just remodeled one, I had some fun with it. Um, so I'm not hating on them, but I'm just saying I wanted something on the modern scale of a cabin. So that's when I decided that there just wasn't anything available like I was wanting, and that if I wanted that type of thing to create an experience with a modern style cabin, um, modern rustic was my goal, that I would have to build it in order to achieve that. So um it started out much smaller than what it turned into. I was I was like, well, I'll just build, I'll spend, you know, this much. And then I got into it and I'm like, well, I really want this, and then it just got bigger. Got a little crazy.

Reshma Vadlamudi 6:21

Yeah, yeah. So did you like you said you started with a small. So first, what was your plan to build one or two? And then how many did that turn into?

David Graber 6:30

Well, yeah,

Multi-Unit Strategy: Infrastructure Leverage + Full-Time Help Economics

David Graber 6:31

so originally when I was looking at running the numbers, I was like, well, if I want to do this, it really makes sense for me to do multiple because um I wanted to achieve a certain amount of income to in order to be able to afford a you know full-time help. You know, I can't just have part-time help that every you know shows up. And so I needed to have help in order to manage. And so it made sense for me to have multiple, especially on the same property, because the infrastructure, building the driveway, building the gate, building um, you know, well and septic was is all under one. So it really did make a lot of sense income-wise to try and do multiple on the property. So I kind of laid out the property. Um in 2020, during COVID, I just walked through my woods and kind of like visioned, like imagined it all. And so come spring 2021, I broke ground on the first build.

Reshma Vadlamudi 7:30

Nice. Yeah. And was that Brandywine? Yes, Brandy Wine.

David Graber 7:36

Brandywine Grove.

Reshma Vadlamudi 7:38

So how many uh cabins are on Brandy Wine Grove now?

David Graber 7:42

There's

Brandywine Grove Today: 4 Cabins + Connected House/Bunker Concept

David Graber 7:43

four open. There's four that are open, and then I'm building the new the new uh house and bunker, which is like basically two separate units that I'm trying to gonna try and rent together, if that makes sense.

Reshma Vadlamudi 7:57

Yes, yeah.

David Graber 7:58

So I want to rent it together as much as I can um because it connects.

Reshma Vadlamudi 8:02

Yeah.

David Graber 8:03

The the bunker connects to the house.

Reshma Vadlamudi 8:05

Yes, I understood that from the from the reels that you post on Instagram. So yeah.

Seasonality Strategy: Rent Together Or Separately Based On Demand

David Graber 8:10

Yeah, but my thought was if if it's slow season, so off season, like in in the winter months, I can rent it separately and still be able to um rent it out to maybe a different clientele that doesn't have as big a party. Yes. Um, so yeah, just trying to give myself options.

Reshma Vadlamudi 8:27

Yes, yes, makes sense. So then how did Paradise Lake happen? So so you you came up with this vision for brandy wine with four cabins, and then when did Paradise Lake happen for you?

David Graber 8:40

Uh yeah,

Paradise Lake Origin: Partner Offer → New Entity Instead Of Selling Equity

David Graber 8:41

so that's a good question. Because basically during the when I started building Brandywine and I kind of got that first one up, um, one of my good friends came to me and was like, hey, we had just done a different real estate deal together. The one in Colorado, I think I spoke about at the event. I did a ranch deal with him in Colorado. We bought a ranch, ended up selling, and we did really well on it. And he's like, hey man, let me invest in the brandy wine. Let me buy, let me buy half a brandy wine. He tried to, he would wanted to buy in. Um, and I was reluctant because I had already owned this property, and I was like, I just went through something really uh hard in my life, and I was just really focused on my kids, and and I was, you know, a lot of my motivation for building this was to be able to make them proud and to be able to give them something someday. Yes, give them a business, like hand it down to my kids and stuff. And so I didn't want my kids to have to buy him out at that time. And so I was like, you know what, it would make a lot of sense for me management-wise. Again, I've gonna jump back to this management. Management-wise, it made more sense to me to have 10 cabins than it does to have four because again, a rental manager, you know, in-house rental manager can have more of a full-time gig and be able

“10 Cabins Makes More Sense Than 4”: Management Economics Explained

David Graber 10:00

to, you know, have a bigger pool of income to be able to pay a full-time maintenance guy, lawn care, landscaping. Oh, there's a lot of work that goes into it. So being able to have that all in-house, um, and so he came to me and was like, hey, let me buy in. I said, I'll tell you what, I'll do a different property with you if you want to invest. Um, I don't want to sell Brandywine. So I told him about this lake that I knew that was for sale. It was just, I guess, just timing. But I had seen it for sale and I was like, man, that would be a great spot. That it's only 20, 25 minutes away. Like it could be like a sister property to Brandywine, and we just kind of like run them as as one, but obviously that's a different entity all by itself. And so that's what we ended up doing. He we went out there and looked at it in the middle of February, and it was snowing and cold, and we went out there and looked at it, and we walked on the backside of that lake, and I was like kind of showing him what I envisioned there in the pine trees, and he's like, I'll do it if you do it. So that's the story. Yeah, my friend Elias.

Reshma Vadlamudi 11:07

Yeah, yeah. So any early risks that paid off for you?

Early Risk: Discomfort, Sacrifice, All-In Capital Commitment

David Graber 11:12

I would say uh just willingness to become uncomfortable. Um, I was very uncomfortable doing what I did the last couple of years. I've worked harder than I've ever worked. I've um had to really um make a lot of sacrifices. I've gave up some sports that I was, you know, I gave up a bunch of traveling that I was doing uh that I wanted to do, and I really had to just focus in on my work and and what I was doing and and grinding. Um so it was a the big sacrifice. Yes. Um I would say risk-wise, yeah, just becoming uncomfortable was risky. Like it's not fun. Yes. Um, also, yeah, I mean, just I guess kind of risked my my life savings of everything I had left of kind of uh was like, hey, I have to make this work, or my life depends on it. So that really makes you work hard too. If you if you're willing to go all in on something, you're quite likely gonna be working a lot harder on it because your life kind of depends on it.

Reshma Vadlamudi 12:27

Yes.

David Graber 12:27

So yeah, I mean, just when I was in the creating stage, you know, in that with that kind of mindset, is like, man, I gotta make this nice enough to where people are gonna come here and spend money and be worth their money. You know, I want them to walk through the door and be like, wow, this is worth the money I just spent to come stay here. And it's what an amazing experience, right? So yeah, that would that was my mindset going into it, and yeah, risky definitely, but just believed in uh my abilities and believed in my talents that I could pull it off and was just gonna like failure wasn't really an option, I was just gonna make it work, whatever it took.

Reshma Vadlamudi 13:07

So yeah, yeah. And and I have to say, like, how did you come up with that idea of the gate? Like everything that we saw like today is awesome. So the gate, the way it looks, um, I think those are pretty similar with Paradise Lake. Is that part of your branding? Is what I'm expecting. I don't know. Yeah, and that's how do you come up with ideas like this?

David Graber 13:35

Yeah, that

Entrance + Gate: Resort Feel + Privacy Enforcement For Paying Guests

David Graber 13:36

was definitely part of the vision for me, is to I think uh think resort, like a resort style property. Um, so I thought that it it just added, not to mention I had problems during construction with people just people found out about the property and they just drive in and they're I'm like, what what what are you guys doing? They're like, We're just looking.

Reshma Vadlamudi 13:57

Yeah.

David Graber 13:57

Like, well, this is private property. You can't just be here. Well, we're just looking. I'm like, well, it's invasive to my guests that are paying to stay here, so you can't just like pull up and we actually had somebody walk around the cabin and just look at the cabin and stuff while there was guests there. So it was it was a a privacy issue as well as just a luxury feel when you pull in. And I would say that that the entrance was largely um influenced by my love for the mountains. If you go out west and you drive mountain roads, you see all kinds of ranch entrances like that. So just kind of like I I liked that. So I brought that and I wanted to have a gate for privacy for people, just adds to the luxury feel. Plus, you don't have people just driving in looking around when they're not supposed to be there.

Reshma Vadlamudi 14:44

Just by looking at that one of the cabins, it's like how do you know where do you put this door? Where do you put this window? So you that you can utilize the maximize the light that's coming in, the view that people are going to have. How you how do you decide? Do you decide that or do you um or you might work with an architect? Do they decide or how does that no?

David Graber 15:05

I I

Site-Driven Design: Arrival Path + Best View Drive Floorplan Decisions

David Graber 15:06

do all floor plans. Um I get them to engineer them after I uh I start with a sheet of paper. I just like take a sheet of paper and I just start drawing. But mostly I look I go to the site and I walk around the site a lot and I'm like, so I two things I want to identify first. Where am I going to be driving up to this place? So where's the driveway coming in and where am I parking? And then where is my best view? Okay. So you want your best view, you want the place you spend the most time in the house to have your best view. And then wherever you can put those big windows in the living room or the great room, or wherever you're gonna have those great big windows, or that's where you want your view. So for instance, like the 45 was built at a 45 degree angle because I wanted to drive up to the front of the cabin, but the view for that particular cabin was just like at a 45 degree to the left. So I was like, Well, how can I capture this view from the back, you know, from the great room and at that angle, but still have the front view when I pull up. And so I just like was standing there and I'm like, what if I build a cabin at a 45 degree angle? So yeah, that's those are kind of my two things. And then outside of that, we we fill in stuff, and some stuff doesn't come out how I want because like the 45 cabin is is only 750 square feet on one floor. So it's super tiny. We have a bedroom and a nice big bathroom down there, a kitchen. So you walk into the kitchen, which is in the front of the cabin, and then the living room is in the back uh with the view, but then we just ran out of space for a table. We had no room for a table. So we ended up doing a big I ended up doing like a big live edge windowsill along beside the kitchen there, and and it's like a big bar top, but you only sit on one side. Um, so it's kind of it's cool, yes, but I would have loved to have a table, I just didn't have enough space. So sometimes you have to sacrifice some things, but you want to get the main things right for sure.

Reshma Vadlamudi 17:21

Yes.

David Graber 17:22

And have good functionality, you know. Sometimes you don't have room for something that you really wanted, um, and then you have to make that sacrifice. So yeah, but that's I love design like shaping and creating, like that is that's one of the funnest things I get to do is just like I said, I start with a paper and then I think about roof plan, how I want the roof to look like. And we start and then I take it to my engineer, they draft that up, I look at it on on their computer software, and I'm like, well, let's change this, that, and the other. And so we just that just starts, yeah, you know, like that.

Reshma Vadlamudi 17:58

Yeah, yeah. Okay. So what's your favorite design so far?

David Graber 18:04

Oh. I mean, I have to say the bunker. The bunker's by far the coolest thing I've ever built. I mean, not hands down.

Reshma Vadlamudi 18:11

That's I don't know if they're if they were even renting out.

David Graber 18:15

I don't think there's any bunker Airbnbs that I know of. Not that I know of. There are some cave ones. Um there's some people that have cool caves. I actually looked at one I think in Arkansas.

Reshma Vadlamudi 18:26

Okay. Yeah, there were there were I think I saw that one on Netflix.

David Graber 18:30

Yeah, there's a really cool one out there. I'd love to go go see it sometime. I didn't even realize that there was such a thing until I got into building this and somebody sent it to me and said, Hey, you need to check this out, get some inspo from this. So I thought, like, obviously, a a real cave would be very, very unique. There's some there's some definitely challenges. Yeah, because you have to have egress doors directly from the bedroom, not to mention water issues. There's a lot of moisture in caves. So I think caves are a huge challenge, but so cool. So cool. Like I could see in the picture they had water buckets in the cave to collect water.

Reshma Vadlamudi 19:11

Oh, is that so?

David Graber 19:12

I think that there's definitely some moisture issues in caves now. I don't I don't know. I mean, so yeah, unfortunately, I didn't have any cave to work with, so I had to make my own cave.

Reshma Vadlamudi 19:22

Yeah. Any mistakes that turned into design lessons?

Design Lesson: Mounting Tvs Too High, Fireplace/Tv Ergonomics

David Graber 19:28

Um, I was just funny. I mean, the first thing that came to my mind, uh, there's obviously there's multiple, but the first thing that came to my mind is I I started mounting TVs uh and and I mounted them too high. That's something that I didn't realize. Kind of put them on the wall where I thought it looked good. And then by the time you sit down in a couch and you're looking up, they're just too high. So I recommend keeping the the fire. If you're gonna put a TV above fireplace, keep that fireplace as low as possible. You don't really have room for. Like uh to to raise it because by the time you sit on a couch and especially in a smaller build, you're kind of close to that fireplace, and now you're just looking up at the TV. So it's definitely uh something that I didn't think about at the time, and now I am much more aware. So now I'm actually putting my fireplaces on the floor and not doing it a hearth in front. Yeah. So um just something simple that I guess I learned in the process. I'm sure there's more, but that was one example.

Reshma Vadlamudi 20:29

Yeah, okay. So let's talk about the ground-up construction. Okay. So what have been some of the biggest lessons from doing ground-up construction?

David Graber 20:38

The

Ground-Up Lesson: It’s Expensive - Labor Is The Shock

David Graber 20:39

biggest well, first of all, it's very expensive.

Reshma Vadlamudi 20:42

Yeah.

David Graber 20:42

Very expensive. And the main the main cost, uh shockingly, is labor. Labor quite la labor prices have have gone skyrocketed. And just trades in general are very, very expensive laborers. They're um they get paid well now. I mean, we need more kids uh willing to do trades because that market's hot right now and everybody's busy and they're making good money. So it's costly. Um, you definitely have to think long term when you're building new new construction. I get some hate on my social media accounts for the price I charge per night. But I mean, actually, I'm I'm very cheap, I feel like, for the the cost of building something like that. Yeah. So people just don't really understand the cost that goes into something building like they're like, oh, $500 a night, that's crazy. Yeah. I'm like, oh yeah, that place costs $500,000 to build, and that's just the building. It's not even the land and the you know improvements.