Chief Milestones

What Scaling Really Costs After the Business Works | David Graber | Part 3

Reshma Vadlamudi Episode 10

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0:00 | 20:18

This episode isn’t about growth or expansion. It’s about the operational constraints that appear once a business finally works.

In Part 3 of this conversation, David Graber - founder of Brandywine Grove - breaks down what scaling actually demands after ground-up construction is validated: complexity, control tradeoffs, and long-term operational risk.

This wasn’t a growth challenge. It was an operating challenge.

We cover:

  • Why scale introduces different constraints than starting
  • How complexity compounds faster than revenue
  • The tradeoff between control and expansion
  • The decisions that protect durability over speed
  • What operators underestimate once growth begins

If you’re a founder, operator, or investor navigating growth pressure and long-term risk, this conversation will feel familiar.

This isn’t a highlight reel. It’s a practical breakdown of how real businesses are sustained - after the build works, not in hindsight.

Reach out: ChiefMilestones@gmail.com

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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“I’m Not A Content Creator” (Why It’s Hard Even When It Works)

Reshma Vadlamudi

You said something about you're not a content creator. Why would you say that?

David Graber

Content creation came hard for me. That was something that wasn't super natural. I see other people just whip up a post and come up with these witty ideas for a post and they're posting two, three times a day. I don't have that mental capacity to be able to put out that much content. It's a lot of work for me still.

Viral Mechanics: Engagement Is The Algorithm (And It’s Free)

Reshma Vadlamudi

It's like a natural thing for you to have so many followers, whatever account you might have.

David Graber

Some of my videos have gone super viral on Facebook. Like crazy. My biggest viral reel ever just slipped over 40 million views. Wow. The algorithm is engagement. You have to have engagement. It's literally free.

Reshma Vadlamudi

How do you stay authentic while still creating viral content?

How A Viral Idea Starts (And Why Most Edits Get Scrapped)

David Graber

In order to go viral, you have to use. I'll hone in on a specific thing. Like, like I know he's working on uh the tunnel one right now. Um I said, hey, let's do a one-minute video of just the process of all this shot creating the tunnel. And we're gonna just clip it all together, and I think it'll be really cool. So yeah, that's how it starts out. And honestly, we do a lot of videos that don't never make the cut. Like he'll he'll edit them and I'm like, I just don't like him. I don't know. I don't know what's wrong with it, but I don't like it.

Reshma Vadlamudi

So do you sit with him through the editing process? You see it, so you tell him what you want, and then you he shows it to you, or how does it work?

Workflow: Vision First, Captions Early, Clips Second

Captions Are The Real Work (And The Real Lever)

David Graber

I share him my vision for it. Okay, so I'll tell him, like, hey, this is what I have visioned for this video. Um, I want I want it to start out with this type of clips, and then I want it to finish with this, or you know, this is what I want to try to achieve. And usually it's built around my caption ideas, you know. We we try to build them together. We used to just build a video and then and then try to fit in a caption to it, but now I try to have a general caption idea before I start the video. Yeah, because a lot of times we ended up having to go back and change clips because you say something that clip doesn't really line up to it, or you can't really see the font or something's weird, and then you have to change. So, and then he'll do like a he'll put it all together and he'll he'll send it to me, like airdrop to me whenever I come to the office or whatever, and he'll be like, check it out, what do you think? I'll watch it and I'll say, I like this, this, and this. Sometimes I'll just like it right away. He he's really good at editing. Um, but then other times I'm like, well, I don't like the flow in this part of the video. I think we need to change this clip to this, and and we'll just switch out those clips, put it together again, and then usually by the end of the day, it's ready to post. And then usually I'll sit down, I usually spend it like probably an hour to on the captions. It's it's hard. The captions are the hardest part because that's the engaging part. Yes, and it's challenging, really, really challenging to come up with new stuff. And sometimes I just I put it all together and I'm like, ah, I like it, I don't love it.

Reshma Vadlamudi

Yeah, you're behind all these, and then I think one of your videos you mentioned you you're not creating, you're not. I I think you said something about you're not a content creator or something around those lines. Why would you say that? Because it's it feels like you have the vision and then you know what how exactly it's supposed to look like, but it you're not just putting it together. That's the only part you're not doing.

From 300 Followers To Learning The Algorithm Fast

David Graber

I feel like content creation came came hard for me. That was something that wasn't supernatural. I saw I understood algorithms pretty quick early on because I I was not in the in social media at all before I did this. I mean, I was I was a 300 followers on a private account.

Reshma Vadlamudi

It's like it's like a natural thing for you to have so many followers, whatever account you might have. Yeah. So it feels like a natural thing, but then yeah,

Why Static Followers Kill Distribution

David Graber

I've definitely gotten better at it. Um, but when I would say when I first started, I would spend hours on something, and I see other people just whip up a post and come up with these witty ideas for a post and just they're posting two, three times a day. And I'm like, I don't have that mental capacity to be able to put out that much content. It's a lot of work for me still. Yeah, yeah, it's a lot of even a story series. I'll put up story like yesterday. I I spent a decent amount of time on that story series, and I'm like, you know, when I should be working, I'm like, well, I try to show stuff behind the scenes because people love seeing that stuff, you know. Try to, you know, engage with them, like get them to engage because that is really the key to algorithm, is is engagement. You have to have engagement. So people, you know, want to well, why do you say certain things and because you and here I just want to say this if you follow somebody that you like their content, every time you scroll by their stuff, just give them a double tap and comment on their stuff or share it to somebody. Like that helps content creators so much. We try so hard to create content that people like, that people want to see, and constantly just trying to uh I don't know, come up with new ideas for content. And so if you like to follow somebody, like you like their stuff, engage with it. It helps them so much. Yeah, helps them so much. Yes, uh, and it doesn't take that long, like quick little comment or something like yes. That's just engagement that helps boost algorithm, keeps your content alive. And the problem is you get so many static followers. People follow you, watch your stuff, but they don't engage, and then your stuff starts trending down. Yeah, and that's it's such a it's such a wave rider for algorithm. I mean, you can be and it crossed something for anyone. No, it's free, right? You're helping your small businesses out so much by just a simple comment. Yes, just to like, just to share. Like just it's like you said, free. It's literally free. And if you like what somebody's doing and you are, you know, love seeing their stuff and you want to see it continue, then do that.

Reshma Vadlamudi

Your content is easily like I would say it's I almost double tap every time, but then I also like share those and then actually save them. Like I have a separate folder. Yeah, I have a separate folder too, um, just so it inspires me to build something like that. So yeah.

David Graber

Yeah, I try to do that more now too. If people I follow, and and if I like their stuff, I follow other content creators that I'm like, oh, that's cool, that's unique. That's like they're creative, they're being creative and they're expressing that creative side online. And I respect it. I'm like, that's awesome.

Facebook Strategy: Reaching Retirees To Fill Weekdays

Reshma Vadlamudi

Do you have Facebook? I know you do have Instagram and stuff. Are you on Facebook too?

David Graber

Yeah, so just recently, actually, is this crazy story? I had Facebook, just a personal Facebook that I just rarely posted on my kids on my profile picture, me and me and my kids, and and just every once in a while I'd throw something up, but it was like a couple hundred followers, my or friends. And so I was like, well, that could be because I was I was thinking about the whole reaching what audience am I reaching for my cabins? And I was hope I was really wanting to reach a little bit of the older generation to fill in weekdays. So my weekends book really fast, but the weekdays are a little harder to book. And I was thinking, I need retirees to be able to come here during the week when they're not working anyway, right? So how do I reach that older crowd? And so that was that was Facebook. I was like, well, I bet you know, Facebook has an older crowd. They're the age range for that is definitely, you know, middle to middle-aged to older people. Um so I was like, well, I so I switched over my Facebook account to a professional account, um, which was really easy to do. And I just linked it directly to my Instagram, and everything I post on Instagram just goes automatically over there. Yeah, I it takes no time. Yeah, post it over. And some of my videos have gone super viral on Facebook. Oh like crazy. So I gained I started doing that like sometime this spring. It was like three or four months ago. And I'm up to like almost 500,000 followers on Facebook.

Reshma Vadlamudi

Oh wow.

Why Reels Outperform Photos On Facebook

David Graber

Yeah, so it's now my biggest, my largest followed account is Facebook. Oh believe it or not. Facebook's a weird place. I don't know how you can go super viral on Facebook.

Reshma Vadlamudi

I think there were there was some kind of stats uh where the reels, um for some reason, because most of the people are posting them just on Instagram, and then Facebook also wants to promote reels.

David Graber

Yep.

Reshma Vadlamudi

And then because you're already posting on your Instagram, maybe that's why like anyone that would post to I think it's the same thing with LinkedIn too. Like if you were to post a video to LinkedIn, you'll be in that top 1% and it promotes for itself. Really? So that's what I heard, but then I'm seeing it work for you. Yeah, it definitely has.

David Graber

Um I yeah, I I did it with great success. I mean, it's still so the thing I don't understand about Facebook that's really weird is like my videos do really well, but like photo posts don't really do that well. So I'm still trying to figure out how why do the videos, it seems like I'm reaching that uh for you page, basically on Facebook, but my page is not necessarily being promoted to my followers. Like I say, I do a photo post and it might only be a few hundred likes on it. Um, but a reel could go, you know, several million views just like that, like really fast.

Reshma Vadlamudi

Uh that's what I heard. Like everywhere, everyone is pushing the videos. Um that's the reason. Like I only heard about Facebook reels, not the photos. And uh even on LinkedIn, just the videos, not the not the content. Like if you were to write and make it a post, it wouldn't work. For some reason, Facebook reels and LinkedIn videos, they are working.

David Graber

Yeah, my largest, um, my biggest viral reel ever uh is on Facebook, and it's it just flipped over 40 million views. Wow, yeah, I think it's 40 million, 30 or 40. Wow. I have to look again. I think it's 40.

Reshma Vadlamudi

Wow, amazing.

David Graber

So that's the largest that was about the bunker.

Reshma Vadlamudi

Oh, is it about so when is that going live? When is the bunker?

Seasonality And Pricing Demand (Jan–Feb Slow)

David Graber

Uh we're I'm shooting for September right now. I'm hoping to have that done September. I think I can pull it off. It might slide into October, the first of October, but I'm gonna push really hard to try and I want to get that fall. Yes, you know, my rush hours fall, so I really want to try and get that booked out um and get that before winter.

Reshma Vadlamudi

I know you said winter is slow. Like, do you say even starting November, December? What when do you say is the uh usually after New Year's?

David Graber

So I can I can kind of get through so November has Thanksgiving and there's still leaves or early November, you know, fine. And then December you get a lot of vacation travelers. Yes. Um, but then right after New Year's, going into that January, February, that's the two slowest months. It's definitely slower, and we we mark our prices down during that time. So if you want to come and you want to come at a cheaper rate, come in January, February. It's I mean weekdays we mark them down and we try to adjust the price per demand.

Reshma Vadlamudi

So how much of the design and branding part is instinct and how much of it is research?

Branding Instincts: What “Looks Small” Vs “Looks Premium”

David Graber

Um, I would say a lot, I do a lot of instinct on that. Um, I have a specific kind of things I've learned. Like I'll I'll use an example. My brother and I bought a small, relatively small tent company from my dad when we were just young, like I was 21 or something like that. My dad had started it kind of out of another business, and he was like kind of doing it on the side, and then he was like, you know what? I'm kind of burned out of this. Like, why don't you guys just buy these tents from me and you you just go and run with it? And so he was, you know, kind enough to set us up on a payment plan, and we we bought these tents from him, and then we started growing these this tent rental business. But my dad had named it A, B, and D tent rental. And I was looking at that and just like, uh, I don't love that. Like everybody's always like, what are the letters stand for? Like, what are I just I didn't think it was like a luxury or a high-end brand. It it felt like mom and pop to me. Uh, especially when you I feel like when you use letters or numbers in your brand, it can it can be kind of like, oh, this is you know, mom and pop type deal. And then not not saying that's bad, yeah. But I wanted a a a better, bigger brand, I guess. And so um, we actually rebranded the 10 company, and um we came up with I did a bunch of just did a deep dive in some different names and ideas, but I came up with Arise, tents and events.

Reshma Vadlamudi

Did I see that somewhere here?

Naming Brandywine Grove: Uniqueness, Availability, Domain/Handle Checks

David Graber

Yeah, it's just out the road. Oh yeah. Yeah, my brother sells it. Yeah, um, arise, tents and events. And I kind of came up with, you know, when you when you rise a tent, it's a rise, you know. And we wanted an a a name that starts with the letter A because it, you know, yes, puts you up higher in searches. Now it's not as big of a deal anymore because you know, yellow pages used to like stack you, but people don't really use yellow pages anymore, so it's all Google searches. But but yeah, back then it was more of a oh, we're gonna be you know, featured first in yellow pages, so you gotta have a name which starts with A. And um so that that's why I came up with Rise Tense Events, and um we rebranded new logo, worked out really well. The company grew like crazy. I'm not a part of that company anymore. I sold out to my brother, but but uh but yeah, it worked out really well, and so I feel like I learned a lot from that experience of like what not to do, what worked, what you know. And so when I came to here, just wanted a you know, a unique name, didn't really know what to. I was totally lost on name for for Brandy Wine Grove. Um, my brother-in-law specializes in graphic design, so I was you know contemplating with him, talking back and forth, and I was forth and I was like, you know, he's like, Well, I really think because Brandy Wine Grove has like a like a patch of trees, like a there's 21 acres here, and like 10 of it is wooded, and then there's crop fields like surrounding and so he's like, I like the fact I was looking at an aerial and I like grove. I think grove would fit because it's like a grove of trees. And he's like, Do you have a specific um do you have a specific tree or a species of tree in your woods that would be ideal to like and you know, like, well, there's smoke trees and you know, maple trees, like oak grove, maple grove, like that's that's kind of plain Jane. Like, I didn't like that at all. And I was like, actually, you know what? I said, I just planted a bunch of brandywine maple trees down my driveway. Did you see the trees going down the driveway? I just planted a bunch of brandywine maple and they turn fire red in fall. Yeah, I was trying to create like a canopy look for when you go down the driveway. So in in 10, 15 years from now, those trees will actually grow the together at the top, and it's gonna be like a tunnel look down the driveway. I'm gonna trim them out to make them look that way. And so I was like, brandywine grove could work. And he's like, I really like it. And I was like, I kind of like it too. Let me think on it. So I just, you know, that's that's how we came up with the brand. Yeah, Paradise Lake was already named. That lake was already named. Um, it's actually on the maps as that. It's an it's a state of Ohio ODR recognized lake, private lake. Um, so we played off of that for that, and we didn't have a choice in that, but yeah. And the first thing you do when you look at a name is do a Google search for that exact name. Yeah, see if there's something else. There was a nothing else called Brandywine Grove. Yeah, literally the only name in that we we couldn't find anything else. Um, there was other stuff, Brandywine, but there was nothing that was Brandywine Grove. Uh huh. And so the domain was available. So brandywine grove.com. Yeah. Domain. So we got that right away. Um, you're gonna want to, if you come up with a brand name, search, uh, do those searches right away and see what's available. Go to GoDaddy or whatever other there's a bunch of different ones you can look. See if your domain actually, I I use Google domains. Um uh, but see if that domain's available. And then the another thing to check in is is the Instagram handle. That's cool. I don't like underscores, yes, weird long numbers, letters. You want it as clean as possible. So if you can look at your Instagram usernames availability, your Google availability, and then your domain, those are kind of probably the three. Obviously, you have to check LLC as well if you want to have an LLC. So those are the four that you can obviously you can change the domain if you have to. You could be brandingwine groveohio.com if you had to. You know, that's what we actually ended up doing. Paradiselake.com was not available. So we went with paradiselakohio.com. Yeah. So that there's there's ways around. Yes. Um, and Paradise Lake on Instagram wasn't available either. So we ended up doing Paradise Lake Ohio on Instagram as well, which fits fine. It rolls good and it's yes, it's fine. But luckily, here all of Brandywine Grove domains were available. Brandywine Grove, the Instagram handle, everything was available. And still to this day, it bothers me so much that I couldn't get David Graber for my Instagram handle. By the way, if anybody, if David Graber is watching this and wants to sell me his domain, his Instagram handle, I'll buy it. I'll make you a nice offer.

Reshma Vadlamudi

But then, but then it fits. Creator fits.

David Graber

Creator fits. I just didn't want to do any letters or numbers or anything weird. So I was like, well, let me try this. It fits, it's fine. I I don't, but I would prefer it to be just clean. If you can get your own, your name and just that, it's so clean.

Reshma Vadlamudi

Yes, I agree. How do you stay authentic while still creating viral content?

Authenticity Constraints: Hooks That Work Vs Hooks You Won’t Use

David Graber

That's that's a great question. Um, in order to go viral, you have to use certain keywords, like what I call a hook. And so there's many a hook that I would love to use that I can't. Um and it just doesn't fit my page. So I know that certain hooks work, but it's just not true to who I am. And also, you know, would have to so for instance, like I've played into divorce content, and I have to be really sensitive with that because I have um I have an ex wife, the kid's mother that I respect and don't want to throw under the Us. Um so obviously our marriage failed and that was not um a proud moment in either of our lives. Uh I know that for a fact, and we both have regrets.