Chief Milestones
Chief Milestones is a business podcast exploring how founders and parents build meaningful companies without sacrificing their health, families, or values.
Through honest conversations with entrepreneurs, investors, parents, and next-generation leaders, the show dives into the real milestones that shape business, wellness, and life.
New episodes release Tuesdays and Fridays.
Chief Milestones
The Hidden Cost of Designing for the Guest Experience | David Graber | Part 4
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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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Authenticity Constraint: Why He Won’t Use Certain Hooks
David GraberI see other people really slander their exes on social media and it's not authentic to me. That's my kid's mom, so I can't I can't do that.
Reshma VadlamudiWhat are some low budget or scrappy ones you recommend for early traction?
David GraberIf
Scrappy Traction: CTA Or The Video Dies
David Graberyou do not ask for a call to action on videos, most of the time they don't do very well. Something that worked for us last year might not be working for us anymore.
Reshma VadlamudiYour content stands out. Do you have a strategy?
David GraberYou
The 3-Second Rule (And Why The First Second Decides Everything)
David Grabereither have to have a video clip or a caption that gets somebody's attention for at least three seconds. So many people swiping that first second.
Reshma VadlamudiHow do you approach storytelling in your videos and posts?
David GraberStorytelling
Storytelling Is The Hardest Lever
David Graberis the hardest. I work the hardest on storytelling. Do you have a design rule? I see a lot of people make this mistake. I have played into it some because the divorce content has done really well for me. People like to know my story. Where did you come from? All that stuff. And so I played into it a little bit, but still tried to always stay very respectful towards her. Um, usually if I would say something like in the caption on screen, I would always write down below, you know, this, you know, no disrespect to my ex. I have a great, you know, co-parenting relationship with her. And, you know, so yeah, just just stuff like that. I see other people like really slander their exes on social media. And that is keyword that people like to, yeah, you know, yes, to do. But I just it's not authentic to me. It's not who I I mean, it's that's that's my kids' mom. So I can't I can't do that. And no matter how I feel about her, I have to respect her because again, it's my kids' mom. So um, yeah, I I don't know if that answers your question, but I try to try to stay, you know, use the hooks as much as I can, but also stay very respectful when I do those. Yes. As much as I can. It's a hard line to walk.
Design Rules: Clean Cover Photos, Minimal Font, Relevance
Reshma VadlamudiYes. Do you have a design rule or filter you follow?
Hook Mechanics And The First Three Seconds
David GraberUm, there's a few I play by. I would say cover photos are a big thing. I don't like a lot of font on my cover photos. I just think it looks messy and YouTube-y, especially on on, even though um, you know, some people would say that's something you should do. I think that your your Instagram, personally, I like my Instagram to look pretty clean. So I do for the most part use uh cover photos to try and keep it as clean as possible and and try to use, I used to not do this and now I'm starting to do more. I try to use a photo that would kind of portray what the video is about. So, like let's say I make a bunker reel, I would like to
Caption Strategy: Hook + CTA + Readable Long Caption
David Grabermake maybe the cover photo be me standing in front of the bunker. You know what I mean? Just so it it relates because you don't want people scrolling through your profile and then tapping on a video, and the the cover photo doesn't relate to the video whatsoever, and it's just a cover photo. Yes. Um that's that's a rule I kind of go by. And then also um I I've found that if you do not ask for a call to action on videos, um most of the time they don't do very well. A strong hook at the beginning, call to action at the end, and then a nice cover photo that portrays to the and then the more it again it seems cheesy, but the more of longer caption you can kind of put in there to people read those, they really do. Um be shocked how many read people read your captions. And so I try to, you know, put something that portrays to the video, something that, you know, little nuggets here and there. Um usually I'll just type it all up, um read it through, make it, you know, add to this, add to that, check all my spelling through chat GPT. Yeah, and uh, but yeah, it it's uh I think those are kind of the the rules I live by, and and again, uh you have to be ever changing, you know. Something that worked for us last year might not be working for us anymore. Yeah. So we try to, for instance, um, while we're on the subject, we just last year we were just doing like cuts with music right on the you know, right on the beat and just the kind of the same style.
Reshma VadlamudiYeah.
David GraberNow we're
Trend Shifts: Music Edits Fading, Raw Footage Rising
David Grabernoticing that that style is kind of trending out, it's not as popular anymore. So we've dabbled with like more raw footage, like no music, just raw clips, put it together and just clip it. And those have been doing really well for us, some of them. So it's just you have to stay, you have to see what other people, what the algorithm likes, what other people are doing, and and then somehow I don't like copying people directly, but bring that to your niche. Like, what are you doing? Bring that style of editing, maybe to your niche of content.
Reshma VadlamudiSo, how do you decide when to blend into nature versus stand out against it?
Design Philosophy: Blending Functionality With Nature
David GraberYeah, that's a good question, too. I would say I try to try to make it as as natural as possible. I like to functionality and nature. I blend I try to blend the functionality and nature together as much as possible.
Reshma VadlamudiI know what does your day-to-day operations team look like?
David GraberUh
Ops Team Structure: Rental Manager + Cleaning Teams
David Graberso Jen is my rental manager, a guest relations um person. She will communicate with all the guests. So when a guest reaches out, has questions, she's the one that responds. Um, she comes to the office Tuesdays and Thursdays from 8 a.m. to 2 p.m. But the rest of the days she works remote. She also handles all ordering all products. Uh so I have her and then a cleaning team. We have roughly three to four people per property. So it takes a pretty decent cleaning team because you have five hours to turn over, and we get a lot of turnovers, and there could be multiple turnovers in a day. So whenever you have, let's say you have four, five, six as high as you could have as high as 10 turnovers in a day, you need a pretty good team to in order to pull that off. So we have some some part-timers that fill in and then a couple full-time. Um, the full timers get about 30 to 40 hours or 30 to 35 hours a week, somewhere in there. And I have like two or three of those. So and the rest are pretty part-time.
Reshma VadlamudiOkay. So Jenny Brochy handles the cleaners and team too, uh, along with the guests.
David GraberSo
Delegation Design: Head Cleaner Per Property
David GraberI I put the the cleaning team in charge of the cleaning team. So there's one head cleaner at each property, and they they coordinate. Okay. So they have a list of cleaners and then they coordinate the schedule. So everybody has the schedule on their phones. Okay. They can see all the checkout check-ins, and then they're they're in charge of making sure that that's cleaned. And then if there's a problem, they'll obviously notify me, like, hey, we don't have enough people to cover here, so we have to fill in. But but yeah, they they're supposed to handle that. Now, I just recently had to uh fire someone that worked here, um, a cleaner, and then that ended up having me coordinate cleans, and that was yeah, that's part of the joys of being a business center.
Reshma VadlamudiYeah, yeah. And how do you handle laundry? Is it on-site, outsourced, or is it hybrid?
Centralized On-Site Laundry (Efficiency, Turnover Speed)
David GraberWe do laundry on site in a different building. So Paradise Lake has its own laundry, laundry house, maid's house, maintenance building, whatever you want to call it, but uh there's commercial laundry in there, and we we centralize that so you can use it, it takes way too long to wash laundry in an individual uh you know, residential washers. Yeah, it's just not efficient at all. So these big 50-pound dryers will dry a massive load of sheets in 20 25 minutes. And so it's it's a no-brainer. You that's another reason to have multiple buildings on one, multiple places on one property is to be able to utilize laundry in that way to have a central laundry. And so we have extra of all linens, yes, all tiles, so we can replace, and while replacing you just wash and then at the end of your day, finish laundry, go home.
Reshma VadlamudiYeah. So does the cleaners do that or do you have one more full-time person for that?
David GraberNo, cleaners are responsible for that. They do their own laundry.
Reshma VadlamudiOkay. What would your pre-launch checklist look like for someone planning a boutique hospitality concept? So whatever you do before your launch, how do you launch your properties?
Pre-Launch Checklist: Photos, Booking Schedule, Test-Stay, Cushion
David GraberWe get everything ready for pictures. So basically, what when we get completely done, we usually schedule photography. Um I like to I like to have it done a few days before we're gonna book it or we're we have our first guest coming. So usually I'll once we get down to the last couple, you know, months on construction, I calculate out exactly what I need to finish this project. And then we we list it and start booking it. And then that gives us like, hey, we have an open date of this, and everything up until then has to be calculated very closely to make sure that can happen. Now I have it got really close one time on not being able to have one ready, but I uh kind of overcommitted myself in that. But but yeah, then I usually so like low cabin, I had it done a week before it was rented. And so that gave us a week to um we had somebody go out and just stay and make sure there was no weird noises or something, you know. So we had somebody stay early, um try out the things, you know, use the washer, use the dishwasher, just to make sure everything was working. Um, and then we scheduled a photo shoot. Actually, I think that's who stayed. Actually, my my uh photographers it ended up staying the night and just checking everything. Um so yeah, that's I like to to give yourself a little wheat cushion there because it's it's super stressful if you're yeah taking pictures at 3 p.m. on you know, you finish the cabin at 2 p.m., take pictures at 3 p.m. and open at 4 p.m. Yes. Not ideal. Yes.
Reshma VadlamudiWhat are some low budget or scrappy ones you recommend for early traction?
David GraberSo this
Low-Budget Traction: Family Sharing → Airbnb Algorithm Lift
David Graberthis would be um sharing it on social media, I think would be the the best way. I mean, you might think that your Facebook has not many followers or whatever, but throw it up there. And I mean, I think I was very low followers when I posted my first Airbnb listing to Facebook, and I had all my aunts and uncles and everybody sharing it to their page, and it actually got quite a bit of traction. And then all those people are clicking on the link and going to your Airbnb and looking at and that just boosts your algorithm on the Airbnb. So I got my listing trending up pretty high just by posting it. Yeah. Um on social media. So yeah, I uh yeah, I mean, social media is at that point is your friend, especially when you have those final photos and yeah, you can finally show off what you've been working on so hard. Yeah, so yeah, I probably would just recommend that.
Reshma VadlamudiYour content stands out. How did you figure out what worked?
Trial-And-Error: Reverse Engineering Why Posts Go Viral
David GraberUm trial and error, pretty much. I think um I I I watched a lot of when I got into social media, I just watched a lot of what other people were doing. And like I would scroll and find a video that went viral, and I'd be like, why did this go viral? And then go read the comments and see what people are commenting about it. And and you start to piece stuff together like oh, they did this, and that's why so many people commented about it. And and you know, it's a blend of that's a blend of the the the right video, you know. You can't just post anything expected to go great, but yeah, the right video and the right message on it.
Reshma VadlamudiDo you have a strategy?
David GraberKind of like
Hook Mechanics + Cutting Dead Space
David Graberwhat I talked about earlier would be uh a solid hook on a video. I think that you need a good hook, something in the first three seconds. You either have to have a video clip or a caption that gets somebody's attention for at least three seconds. So many people swiping that first second. So I always say you could, you know, you could have the best video in the world if it's at the end of your video, people might never watch it, you know. And so you gotta get them to the good part. Um so that first three seconds is so important. I I think that's one of my biggest strategies is trying to get people to watch past three seconds, and then you gotta hold them past that, obviously. But we live in a now society. So I would say another strategy is cut out dead space. Um, if you have a lot of dead space in your video, I see a lot of people make this mistake when they when they uh film. So they might be let's just take a lifting video. So somebody might be like showing me their lift, but they're also showing me them setting up their camera, walking over to their lift, taking a couple deep breaths, walking to the bar, grabbing the bar, and doing their lift. Well, you could have just showed me the lift, you didn't have to show me all that before. That's dead space. Um, unless you're super famous, most people are probably not going to watch your dead space videos. Um, so cutting out that dead space uh in videos really helps you because again, even stories, people tapping right through those. They look at the first second of every story and they don't watch the whole thing. So when you think of it that way, try to keep your content super entertaining, like what's happening next type deal, in order for people to stay on it. I don't know. That's just a strategy that I try to play with.
Reshma VadlamudiHow do you approach storytelling in your videos and posts?
Story Structure: On-Screen Bullets, Caption Depth
David GraberStorytelling is the hardest. I work the hardest on storytelling uh videos. Like, so if I'm trying to tell you trying to brief them in the on-screen, so when you're showing them a video, you try to like brief them on screen and then the full story in captioned below. So um don't put too much wording on because if they can't read it, it's not gonna, you know, it's too much to read. But you make you give them like the bullet points on screen and then read caption for more, and then you put the full story down below. Um, then you can go as much detail as you want and tell the full story, but just keep it simple on screen so that you can watch the video and read the words, and you don't have to like if there's something going on in the video and there's a whole paragraph to read. I'm not gonna read it.
Reshma VadlamudiDo you batch and planned content or go with the real-time inspiration?
David GraberWe
Real-Time Content + Archives/Repurposing
David Graberdon't really batch, no. Like we have monthly meetings and we talk about things that we want to do. So I, you know, in my meetings, I'm like, hey, would like to do, for instance, last month. We want to do a tour of a cabin, a full tour. So we just put that out recently, actually. It's on my page. So um different style of content. We're trying to, you know, try this this month, and then and then we go pretty like what's happening this week, you know. We just shot created that that inside of that cave. So I'm like, let's let's put the shot creep video together and try to get that out. It's probably coming out tomorrow. He's working on it right now. So if I can find the caption at the time to put the captions on it and stuff, then I'll release that probably tomorrow. Hopefully this week. Yeah, it just depends, but it's pretty real time. I try to stay real time, and then uh occasionally we'll we'll dig back into our archives. So basically, like log cabin content last year, we never got good final content because we finished it in the winter, so there was no like summer. So just this spring, we finally were able to shoot that with like green grass and green trees and all that. So we just shot that recently, and now we've been releasing more transformation content from that log cabin. It's doing really well, but it's kind of old stuff. You can go back and get stuff as long as you're bringing it, you know.
Reshma VadlamudiSo you you're repurposing the cabin.
David GraberYeah, you sometimes you repurpose because last last summer a lot of my content was about that log cabin because I was storytelling the whole story about the process of now we're doing this, now we're doing that, and now I'm kind of recapping that all like start to finish. And that content's done really well. So you can really do real time and you know previous. Yeah. Yeah.
Reshma VadlamudiSo what has helped you build community and not just the followers?
Building Community Vs Scale Limits (Dms, Stories, Engagement)
David GraberI think being really authentic and real on on this on the posts and then and the stories. Um one thing I don't do a great job is communicating with my followers. Uh, I struggle with that because I can't, I just simply can't keep up. So I get a lot of messages I don't respond to, and I wish I had the capacity to do that. Um, you know, I have I just simply don't have the capacity. I should probably hire a a uh but then it's not me.
Reshma VadlamudiDo you self-manage all your accounts? My accounts?
David GraberYeah. My personal account I do, yeah. Okay. Um the I have other people on my business accounts helping with the messages on there. Yeah. So we try to respond to those. Emails I have help with, but not personal account, it's just me. So yeah, I don't get back to everybody. I really don't. I mean, it's it's it's impossible. Like by the end of my day, yes, I am just exhausted and I'm like, okay, I cannot do this right now. I need to rest and get ready for tomorrow. So and then my kids take a lot of time and sports and all that stuff. So so yeah, that's that's the hardest part of not being able to get back to people. Um so I would say I could even do better than that, really, if I was more engaged, but I try to be engaging in my story. So if you want to engage with me, that's the that's the place to do it in my stories. Because I, you know, post these little boxes, I read all those, 100% of them. I read them all. That's why I really want to do, I would love to share that uh in a way that I can to a mass versus just you know, individually.
Reshma VadlamudiHow do you think you can do that?
David GraberWell, I'm I'm
The “Workshop/Mastermind” Idea As A Scaling Mechanism
David Grabertempted to, I'm actually really tempted to do a um uh some sort of uh class, like a workshop class online to to offer that. I know there's a lot of people doing that. What is the name for it?
Reshma VadlamudiOh, they call it master class, they call it mastermind. Yeah, there are different names to it.
David GraberI know, yeah, I've wanted to do that. I think just because of that reason alone, not that I necessarily really want to take the time to go record, you know, a thousand hours of video or whatever it is, but I don't have the time to do that. But it would be a way for those people, you know, you could direct them to that. Like, hey, if you really want to learn, here's a place where I've shared everything.
Reshma VadlamudiAdvice for anyone that's trying to stand out on social for the hospitality brands.
David GraberSo at
Hospitality Social Is Now Crowded (Standing Out Got Harder)
David Graberfirst this was easy. I will say this that you know hospitality brands, when they first came to socials, they really took off because people were. Like, oh, this is cool. But now there's a lot of people on there doing the same thing.