What Success Still Costs After the Business Works | David Graber | Part 5

This episode isn’t about building momentum. It’s about what happens after momentum stabilizes.

In Part 5 of this conversation, David Graber reflects on the real cost of building a business that worked - the personal, operational, and identity-level tradeoffs that only surface once the pressure eases.

This wasn’t a growth problem. It was a reckoning.

We cover:

• The costs that don’t appear in financial models
• Why clarity matters more after success than before it
• How operators reassess identity once survival is no longer the driver
• What David would still choose again - and what he’d protect differently
• Why building something real always leaves a mark

If you’re a founder or operator who’s already crossed the hard part, this conversation will feel familiar.
 This isn’t a victory lap. It’s a closing chapter - told without hindsight gloss.

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

“If You Have What Everyone Has, You Won’t Stand Out”

David Graber 0:00

If you have something that a lot of people have, it's gonna be hard to stand out. You have to be unique. I call it Instagrammable.

Reshma Vadlamudi 0:06

What would your top tips be to build momentum on social media from day one?

Momentum Rule: Consistency + Quality (And The Algorithm Dies Fast)

David Graber 0:11

If you let it die, the algorithm dies fast. But when you have any type of momentum consistency, the algorithm sees that and somebody stay here with a million followers. They posted a video and it did horribly for them because it was not in their niche of content.

Reshma Vadlamudi 0:27

How has your definition of success evolved?

David Graber 0:30

It's got three Lambos in the front, like that's success. For some, but like for me, I'm so focused on where can I put money that makes me money?

Reshma Vadlamudi 0:38

What would you say to someone sitting on a big vision but afraid to start?

David Graber 0:42

When the pain of staying the same is greater than the pain of change, you change. If you have something that a lot of people have, it's gonna be hard to stand out. You have to have, I think this is where you have to be unique. I call it Instagrammable.

Reshma Vadlamudi 1:00

Yeah. What would your top tips be to build momentum on social media from day one?

David Graber 1:06

Well, the the number one rule is consistency. You have to be consistent. Um, and that doesn't mean that you sacrifice quality for consistency. Um I think just being whatever that number is, if you only post once a week, then then at least post once a week. So if you're like, well, I only want to post once a week, okay, well then at least do that. At the bare minimum, post once a week and make sure you never miss. Because what people tend to do is like, oh, well, I haven't posted in a month. Why why didn't you post? Well, I just got busy, you know. So it can if you let it die, it die, the algorithm dies fast. But when you have any type of momentum consistency, the algorithm sees that. Uh, and then quality. You have to put out quality content. You can't just throw up a little camograph of some sort and and expect you know it to do well. So consistency, quality. Not saying you can't do we we have some posts that we put out that we feel are filler posts. They'll do okay. My followers are like them, but they won't really do good on the for you page. So that's considered a filler post for us.

Reshma Vadlamudi 2:21

Okay.

Predicting Virality: Filler Vs Breakout Posts

David Graber 2:22

Um, and then when we post, like for instance, the one I posted the other day, I was like, oh, that's going viral for sure. And it did. So I I can kind of call them when they go out. Yeah. Most of the time I call them, not always, but I've doing it long enough now that I can call them when they when they are like, oh, it'll be fine, it'll do fine, but it's not gonna go viral. Like I can call that, or I'll be like, oh, that's going viral. And sometimes I'm wrong.

Reshma Vadlamudi 2:45

I've been wrong before, but so how did you approach building? I would say both Brandywine and the Paradise Lake brands, and was it intentional from day one, or was that something that evolved?

David Graber 3:00

Uh so the Paradise Lake brand, that was we bought a property that the lake was called Paradise Lake. And so we felt that that was important to play off of that name. It was it was recognized as a Odinar Lake in Ohio, and so we played off of that. We didn't really have a choice in that, but just you know, tried to keep it super clean in our, you know, our sign at the entrance and stuff. Uh clean. Um, we used a dark bronze and a gold color, went really well together.

Website Conversion Reality: Clicks Are The Bottleneck (Organic Only)

Reshma Vadlamudi 3:32

Yeah, so what role has your website played in bookings or brand trust?

David Graber 3:37

Your own website to book is is less fees, obviously. So less fees for your guests. You have to bring in clicks to your website. So for me, that's all social media. I bring clicks through social media, and I don't really have another way to do it other than you know, you can do Google AdWords, which I don't do. I have not spent any money on any type of advertising like that. It's all organic. So being able to get traction on social media is very important to getting clicks on websites because you have it directly on your Instagram link, link to book right there.

Reshma Vadlamudi 4:14

So, how much of uh are you on Airbnb or are you not?

Airbnb Vs Direct: Shifting To ~76% Direct Bookings

David Graber 4:18

I am. I do Airbnb as well. I started out doing all Airbnb, but then I switched it and started up my personal, my own website, and now I'm 76% personal bookings, direct bookings.

Reshma Vadlamudi 4:34

Yeah. So do you work with creators like inviting the the influencers, inviting them onto the property, or is that I used to do that a lot um at first.

Influencer Trap: 1m Followers, Weak Results (Niche Mismatch)

David Graber 4:45

I would say a lot, a decent amount at first, and I don't really do it anymore. Okay. I feel like I just don't take the time. It takes a lot of time to coordinate dates and all that. So at first I I was messaging all those people back, and now I still get a lot of messages about it, and I just haven't really um, but I probably should, to be honest. It's a great way to if they're I think their contact, their content has to align with your content as far as are they just some influencer um on social media, are they actually does their content align with your content as far as style and all that stuff? I think it has to in order. We we actually a good example is I had somebody stay here with a million followers on Instagram, over a million, and they posted a video and it did horribly for them because it was not in their niche of content. It was like a fitness influencer that that uh posted uh a cabin stay of her and her girlfriends, and it did not do well. Like it actually did really poorly, I thought. Um, and so it was just a lesson to you know their niche of followers are not weren't really looking for that. They're they're following for another reason. So I think it's important to align that up a little bit. Yeah, okay.

Reshma Vadlamudi 6:09

So anything else you're building or excited about that you can share?

Why He’s Pausing Construction To Tighten Management + SEO

David Graber 6:14

Previously, as the bunker is my current build right now, and uh underground bunker attached to a house. Um I'm gonna be able to host small events, bigger groups. Um it's gonna be it's gonna be a pretty sweet place. It's gonna be really cool. The best, obviously, it's gonna be by far the best build I've ever built. It's it's gonna be very unique. Yeah. Um, we're in the middle of the project right now, and it's really fun. I'm enjoying it. It's the hardest one I've ever had to do. So uh, but yeah, that's what I got going on. And after that, I really don't have anything planned. I'm planning to take a little break from building after this. Um I've had, yeah, I've had some pretty high stress the last couple years, and I feel like I need to just, I don't know what that period of time is. It might only be a few months, but I need to take like usually I would be as I'm finishing up a project, I would be starting a new one. Like I'd already be starting a new one now as I'm finishing up this, and I'm not gonna do that this time. I'm gonna finish this, get it all done, and probably take like over the winter to just really fine-tune my management side of everything. I want to get everything running well, search engine optimization and like all the fine details to make sure these these companies are running smoothly at a high level before I just go diving into something new again. Yeah. Um, because I haven't really had the time to focus on the things that that you know I should be focusing on. Um, so my my plan is to take a period of time and and focus in on not not rest and recover. It's not gonna be like that. It's still gonna be working hard, but a different hard on a different thing. Yes.

Reshma Vadlamudi 8:02

So just not building, but still working on the business.

David Graber 8:05

Yes, yes, growing the business, just not the buildings.

Reshma Vadlamudi 8:08

Yes. How do you stay creatively fueled as things grow?

David Graber 8:15

Yeah, this gets harder and harder because even as I build, I have to outdo myself now. Yes. Uh so and outdoing myself involves me spending more money, which is challenging uh because you gotta make the numbers work. I always tell my team, I tell my people, I'm like, well, building these uh makes no sense if they don't make money. If I can't make money doing this, I it makes no sense why why I do it. So um I keep that in mind as I'm building, and that's uh that's one of the biggest challenges is I end up having to do a lot of stuff myself and and to try and make up for high prices of contractors and stuff. I end up trying to do as much as I can by myself. I just I got a quote for the pool, and it was outrageous. Nothing I could afford. And so I was like, well, I'm gonna have to figure this out on my own. So I hired a local pool contractor to plumb it, and I'm gonna help, you know, form it up and do the do the concrete shot work. I'm hiring a couple laborers to help, and um, we're gonna piece it all together, and it's gonna be way less that way than to just have somebody would have been way easier for me to just hire the other guy, but it was it was a substantial difference in price. So I'm gonna like kind of like self-guide it or not self-guide it, self-contract it the pool.

Reshma Vadlamudi 9:41

Yeah, yeah. How has your definition of success evolved?

Success Redefined: Lambos Vs Assets That Pay You Back

David Graber 9:45

That's a hard question. I I feel like so many people have a different opinion of this. There's a lot of people. I've just been recently talking to some guys that are super impressed by Ferraris and Lambos, and you know, that's their definition of success. Like, oh, he's got three Lambos in the front. Like he that's success, right?

Reshma Vadlamudi 10:03

For some.

David Graber 10:04

For some. Yeah. Mine hasn't been that. I I don't I I mean, okay, cool. That's cool. But I would say just um, you know, assets. Cars aren't really assets, to be honest, they're liabilities. What kind of assets do you have? So let's define the difference between an asset and a liability. A liability is a depreciating thing, which vehicles, cars, all that stuff is. I'm not saying don't drive a nice car, but but like for me, I'm so focused on building assets. Like, where can I put money that makes me money? That's that's my definition of success. Like, where can I put money that makes me money? And if if I can invest and it makes me money, now it's so much you're investing into the future though. Like you think you have to think so long term, like I'm pouring all this money into this, but then years later, this is gonna pay me back for years, and so it it definitely takes a long thinking mentality. Yeah, but that is my definition of success is to build assets. Yeah, so yeah, if you're a young kid and you just dream about owning a Lambo, um I would say take your focus off that and focus on assets. What can I where can I spend my money that makes me money?

Reshma Vadlamudi 11:36

Like so, what has building Brandywine and Paradise Lake taught you about yourself?

David Graber 11:43

Um I I've definitely gotten become a better person, I think, uh from it. Just it taught me a lot of um being willing to become uncomfortable is actually a good thing in life. And unknown future is not a bad thing either. Like having you know we we're so programmed to have everything calculated and everything figured out. We think we need to know exactly where we're gonna be in five years and ten years and and um just being okay with being uncomfortable um is and not knowing exactly how it's gonna turn out, but willing to trust the process. Like if I work hard and I do things the right way, good things will happen to me. And so that's been my motto.

Reshma Vadlamudi 12:39

What would you say to someone sitting on a big vision but afraid to start?

Starting A Big Vision: Fear, Failure, And The Cost Of Change

David Graber 12:43

When the pain of staying the same is greater than the pain of change, you change. When the pain of staying the same is greater than the pain of change, you're gonna change. So how bad do you want it? It might cost you everything, it might cost you all the security you had, your life savings, everything you have. It might cost you everything. Are you willing to to to do that? Like you and then you have to be okay with failing. Like when I went into this, I was like, you know what? If I fail, if I fail, I'm okay with it. Because I will know that I gave everything I had. I I done my research, I did my due diligence, I worked my ass off, I gave everything I had. And if I still fail, if the economy fails and something happens, something crazy, everybody always like, well, aren't you worried about the counterfilling? It could. Yeah. There's gonna be a lot of other people in trouble too, and I might fail, and I could fail. But I will know that I gave everything I had, and I'm still gonna be okay. And that's one thing that divorce taught me. Divorce is a failed marriage, and I had never really failed at anything in life that like drastic at all. And I so I was always like, you know, just taught that you know, you gotta be a winner at everything, you know, you win, win, win, win, win. And when I went through my divorce, um that was just a huge failure that the public, everybody saw. And I mean, it's humiliating, totally humiliating. And so sitting in that and then being okay with like who I was after that, like, okay, I failed. I you know, now it's get back up and go again. You try harder, you go, you learn from your mistakes, you learn what you know that lesson taught you, and then so I think that if that's one thing it taught me was that I'm still okay after failure. And so if I most people don't follow their dreams because of one thing, it's fear. So if you can overcome the fear of failure, you pretty much can chase whatever dream you have. I mean, it's the fear of failure. That is what holds most people back. So overcoming that fear of failure, you have to be okay with failing.