The Ugly Truth About Entrepreneurship Nobody Talks About

Everyone sees the beautiful photos, successful businesses, and dream lifestyle.

What they don't see are the sleepless nights, late rent payments, maxed-out budgets, relationship stress, and constant fear of failure.

In this episode, Madi and Skyler from For The Love of Upstate share the raw truth behind building an 8-property short-term rental portfolio, working as a couple, managing investor money, and sacrificing comfort to chase a dream.

We talk about:
 ✨ The reality behind "Instagram success"
 ✨ Entrepreneurship vs. a traditional 9-5
 ✨ Building a business with your partner
 ✨ The pressure of managing other people's money
 ✨ Why they almost wouldn't do it again
 ✨ The advice they'd give their younger selves
 ✨ The mindset that kept them going when things got hard

If you've ever thought about quitting your job, starting a business, investing in real estate, or chasing a dream that feels bigger than you, this conversation is for you.

Hosted by Ethan Glidewell & Sarah Glidewell 

You can view the video & audio version on our Youtube Channel 

Thanks for listening!

Transcript

SPEAKER_00 0:00

You start thinking about going back to work for somebody, and it's like the first question they ask you is like, Can you work nine to five? And I'm like, every day? I can give you a day or two. You know, but like, no. And so that's just that re-reminder. Just that question of somebody asking me that. I'm like, never mind. It's all worth it. Never mind. Yeah, no, I can't.

SPEAKER_04 0:40

All right, everybody. Welcome back to another episode of Design to Glide Well. Uh, today we have two of our favorite people on as guests. Um, you have definitely heard them as our guests on previous podcasts before. You've seen them with us on social media. And today we're just gonna unpack a lot more of the behind the scenes of their story or their journey for the last few years. So, Maddie and Skylar, thank you for joining us. Welcome. Thanks for having us. Thank you. So excited. Absolutely. So, for any of our listeners who are unfamiliar with who you are, will you give us like an elevator pitch on who you are, what you do in the short-term rental space?

SPEAKER_05 1:17

Come here.

SPEAKER_04 1:18

Yeah, that's Skylar's job.

SPEAKER_05 1:19

Yeah. So Maddie and I founded For the Love of Upstate, what, three years ago now?

SPEAKER_01 1:24

Almost. Yeah.

SPEAKER_05 1:25

So we've been doing projects all across upstate New York. We're up to eight short-term rentals, a boutique hotel, and now we're starting to do flips across upstate New York as well. So we have done, I mean, I think I've done over 50 projects total from the project management standpoint. Um, used to work for a large short-term rental fund um doing projects across the United States. Maddie was also working for that fund where she was doing acquisitions. Um, so we kind of were able to bring our skill set together to be able to build our business for the love of upstate.

SPEAKER_02 1:55

Yeah.

SPEAKER_05 1:56

Wow.

SPEAKER_00 1:56

And you still have hair. Yeah. All those projects.

SPEAKER_03 1:59

We're getting a little gray. I saw my first gray hair yesterday. Hey, the cameras can't see that.

SPEAKER_04 2:06

Relatable though, because same. I was like, is this the purple shampoo? No, it's not.

SPEAKER_00 2:12

The benefit of having white hair already. I can't tell.

SPEAKER_04 2:16

Well, to kick this conversation off, I think one thing that is like particularly interesting and unique about you two is that we've been talking to couples where there's there's gas and clutch, Ethan says, instead of breaks.

SPEAKER_00 2:30

Yeah, we said gas and break earlier, but we think gas and break earlier. Yes.

SPEAKER_04 2:34

So it's not anyone that's like stopping, but it is like a pause. And so I think the more common dynamic in relationships is the guy is the gas and the girl is the clutch. But in knowing you guys intimately, you guys are the opposite. And so I want a little bit of insight, especially in the fact that I know that you don't particularly love what you do.

SPEAKER_02 2:55

Yep.

SPEAKER_04 2:56

Right? But you are excellent at it, you're doing it, you've been committed to it for like a really long time.

SPEAKER_02 3:00

Yep.

SPEAKER_04 3:00

I want to know what the internal conversations look like for you guys around getting on the same page of this dream of building for the love of upstate, what those look like, how you guys feel about aligning on that overall vision. Yeah.

SPEAKER_03 3:12

Yeah. Gosh, where to even start? I feel like trauma done. Therapy sessions without putting it. Yeah, I feel like it's been a very open conversation and we have to have very frequent check-ins because I think because the dynamic is normally switched, like it's normally the man who's really driving things and the woman who kind of has to go along. I've had a lot of women like confide in me about what it's like to be the one who's like always following the man and the pain points that can come from that. Yeah. So I feel like because of that, I'm always very making it a point to like check in with Skylar to make sure he doesn't feel like I'm bulldozing him. Or he doesn't he doesn't like disguise what he really wants because he can tell that I'm like someone who like really, really wants what they want. And I never want his needs to feel like secondary to mine. So I feel like I just always try to make sure that I'm not bulldozing. And I Skylar will be like, Oh, I don't mind, or like you decide, like, I don't have a strong opinion on that. So I'm always like, Are you sure? Yeah, are you sure you don't have a strong opinion? Because like you're allowed to have one, and like I will compromise with you, I will meet you in the middle. Yeah. Um, so yeah, I feel like it's just about continuing to check in as we grow and we enter like different phases. Yeah, yeah, absolutely.

SPEAKER_05 4:22

I think like right now we've talked a lot about um we're doing your dream right now, and you know, my dream is like I I love sports. If you know me, I will talk your off about pretty much any sport possible, and that's what I wanted to do with my career. But thankfully early on, I got to work for a team in sports and realized you don't make any money at an entry-level position working in sports. So thankfully I got that, you know, notified into my life very early on and was able to pivot away. But we're doing your dream now. You love designing these properties. I think I've found I have a very like operational mind to kind of help you know fit into what you're not good at and vice versa. Um, but this is a way to make money for the most part for me, whereas this is more of like your dream. Um but I know Maddie's dream is a lot more lucrative than maybe my dream. Yeah, maybe so I think it's good to be able to um talk about those things and you know, one person maybe has something that we need to be working on right now, or the other one can come later.

SPEAKER_04 5:19

Yeah, yeah, yeah. From your perspective of you being in that leadership role right now, how do you carry the weight of that? Yeah, because I feel like that's a that's a something that as women we don't always feel the obligation to do because it oftentimes just naturally falls on the man, and you're carrying that. So, like from your perspective, from a mental health check-in, how does it feel to like be in that role in your relationship?

SPEAKER_03 5:46

Yeah, it is scary like being the one to call the shots because I'm always worried, like you know, I was the one who was like, let's move to upstate New York, like I'm the one who's like, let's quit our jobs, like let's I really put us in a really precarious situation, and we carry a lot of risk because of what I wanted to do. Yeah, so I think it is very stressful, and it's made me very motivated to make sure it works out. Like, there is no part of me that isn't 100% positive that this is all going to be worth it. Yeah, and I think because of everything I put on the line, because Skylar has sacrificed what he wants to do to help me build what I want to build, I am like dedicated to making sure that it was worth all of the sacrifice and all the time spent on it.

SPEAKER_05 6:28

Yeah, that's awesome. Yeah, we've gotten better at that too. I feel like you've told me that many times, you know, that it is a hard burden to carry. So I feel like recently I feel like I've been a little bit more opinionated, making sure that she knows I'm also on board, she's not making the decision alone, um, all those things. So it's not just her on the line.

SPEAKER_00 6:49

Checking in with her, yeah, like she does with you.

SPEAKER_05 6:51

Yeah, yeah.

SPEAKER_00 6:52

Great idea.

SPEAKER_02 6:52

Yeah.

SPEAKER_00 6:53

Yeah, that's amazing.

SPEAKER_04 6:56

Well, and I think too, I would imagine that like there's a lot of time left on the clock, right? And I think that one thing that's very relatable for us with you guys is that I could totally see those roles reversing as time goes on. And those roles have reversed in our relationship as well. And I think it takes a very unique couple dynamic to be able to shift in those roles because more often than not, it's like you've got a very strong leader and then a very strong supporter. And I think that it's unique to have this perspective of a couple where you have to kind of carry both roles. Sometimes you're the leader, sometimes you're their supporter, and it allows you to really resonate with what role the other is in. So I just have watched you guys do that so well over the years.

SPEAKER_03 7:38

Yeah, it's been tricky because I think maybe more recently, and I think it's me becoming like a little more mature, realizing that I don't necessarily like want to always be in the driver's seat. Like, I feel like when I was a kid and like in high school and college, I felt like I had to, like, I felt like I had to be the one that always takes charge and like is always in control of the whole situation. And I think through being with Skylar and being able to like fully trust him, I'm like, oh, I don't always have to do that, and it's actually really nice to not do that. Like it's really nice to be a passenger princess, yeah. Other areas. So I feel like we have navigated that a little bit. And Skylar is very good at like reminding me, like, you know, like maybe the first time I suggest something, you can say okay. Instead of me like asking a million questions and be like, Are you sure? Like, did you think about this? Did you think about this? And I'm like, Oh, he really does think things through more than I do. Yeah, so maybe next time he does call a shot, I can just be like, Okay, yeah.

SPEAKER_04 8:34

Yeah, that's so relatable because I feel like I I have the same sentiment about just in every previous relationship to Ethan. I just knew that if I were to spend forever with this person, I was gonna be the breadwinner, I was going to lead the relationship. Like it almost felt like I carried a motherly role. And so there was so much about Ethan that was like very traditional Texan, right? That was like a breath of fresh air. But the the realization, I guess, that he had that traditional Texan, and then also me trying to like lower my expectation for myself of like leading the relationship, those two things didn't happen simultaneously. You know, and so it's taken me a really long time, just like you, and I feel like that's why we connected so quickly when I met you, because I was like, Whoa, I see so much of myself in you, and it feels good to feel seen by someone in the same way.

SPEAKER_03 9:28

Yes, 100%. Yeah, I remember when we first met telling my best friend Sydney, I feel like I like I feel like Sarah and I are so similar, but you're always like a few steps ahead, and you always have wisdom to impart on like whatever we're going through, and it's just like I have the chills right now. Because the things that you say just like blow my mind in the sense that like you fully understand how I am, like how our relationship works, and I feel like that has been like a huge part of our journey. Yeah, yeah, thank God.

SPEAKER_04 9:54

Thank God, because it's lonely out here sometimes. It is, it really is. But it is.

SPEAKER_00 9:59

Well, speaking of our journey, I want to ask you guys a question. Um, I'm skipping ahead on our question box here, but I just think it rolls right into it. It for those that don't know, I hopped into project management with her last year, and um, I think you guys both mentioned to me um that I probably wouldn't like it.

SPEAKER_04 10:22

Um, no, no, no, it'll be fine.

SPEAKER_00 10:25

I had just sold or was in the process of selling my insurance business that was successful, it was a leadership role, but a sales role, you know, and you you just think that all those uh characteristics can translate to the next thing. And so I took that blind optimism into project management and found out very quickly, boy, was I wrong. Was I wrong? So, with that being said, you guys wear a ton of different hats doing what you do, whether it be capital raising, project management, um you know design, all the things that go into doing what you guys do. So, can you tell me what are like your favorite hats to wear and what are your least favorite? Could give that away as quickly as possible hats.

SPEAKER_05 11:09

Mine is easy from the giveaway hat side of things. All of it. You can't say that. I think recently, I think it's been a build-up to this point, but it's the and you guys have heard me talk about this, but it's the property management side of things. Like, but that one is hard to me to give away because I feel like it is like honestly the most important part because it takes a lot of work to get a property up and running, but it takes even more work to keep it nice.

SPEAKER_00 11:35

And who knows the property better at the end here?

SPEAKER_04 11:37

Yeah, I mean I feel that if you project managed it, exactly.

SPEAKER_05 11:41

Like it's like, where's the water shut off for this one sink and this one bathroom?

SPEAKER_00 11:45

Yep.

SPEAKER_05 11:46

Literally no one knows that except for me and maybe the contractor, and that's it. So that's been the hardest one to kind of get rid of. Um, thankfully, we have Fede that, you know, the whole Blackbird team like steps up and helps with a lot of that stuff and been able to communicate and actually help train them on particulars with each house because every house is so unique. Um, that's been the hardest one to give away, but it's the one I want to give away the most because it just now that we're at eight, it was easy when it was two, three, four, but now we're at eight, and it's like, okay, every day there's something, you know, that goes on. So um that one takes up the most time. Uh, I would say the hat that I like to keep. Gosh, that's a hard literally none of that. Um gosh. Keep none, get rid of all. I guess I'll change it a little bit. Like, I think what I know I need to do and what I've been trying to do recently is like step more into like an ownership role with the things that I'm in charge of in our business, which is again the project management, the property management. Um, and you know, the way that we're doing that is trying to hire the right people. And so I I've realized recently and talked a lot about my with my therapist about I think I have a control problem with a lot of those things. And um, even the people that we've hired are really good, but I still have like a are you doing this like the right way? Like, are you not messing up? Like, so that's been really difficult, but I think that's like the hat that I know I need to wear is like I need to be an owner, Maddie, and I need to not be like so far in the weeds every day with minute details and more the vision and you know creating the systems to make people successful. Um, so I know that's the hat I need to.

SPEAKER_00 13:22

What an exciting position to be in, though. For sure, right? Like this is a new level. 100% new level, new devil. Like that's exciting. You just another problem you have to solve. Exactly. Yeah, like the problems five years ago are significantly different than the problems today.

SPEAKER_05 13:35

Oh, 100%.

SPEAKER_00 13:36

And although it is stressful and you get pissed off often, it's like part of it, right? And so if you just take a step back and like realize like this is what I wanted, and this is what I've got. What an exciting time.

SPEAKER_05 13:47

Yeah, I think it's a little scary, right? Because it's you take on so much more of like as an owner, um, and the things you have to do on a daily basis. Like every day, I'm like, okay, what is actually important for me to work on right now? And most of the things that I have been doing up until this point are like not important really to be working on. So you're having to like create a new list of things that okay, this is the stuff I should be focusing on.

SPEAKER_00 14:07

Yeah, you should probably actually have to tackle the one that you don't want to tackle. The stuff that's been on the top list. The one that's always on the top of the to-do list. But by the end of the day, it's on the bottom, not done. 100% guilty. Yeah.

SPEAKER_03 14:18

I feel like you've had to reframe like what productivity looks like too. Because I think both of us will talk about like picking up tasks that we could easily outsource, but we do because it feels like really good to like check off of these really easy things. And I feel like now you have to reframe, like you feel really really productive, like placing the Amazon orders or like calling a septic companies. And I'm like, Skylar, why are you doing this? And he's like, Well, it just feels so good to get things done. And so we've I feel like you've especially had to reframe like a productive day, might not be doing any task, but just like talking to like six people, yeah. Yes, and it doesn't feel as good because you can't like check, check, check, yeah, but it's gonna move the needle way more than a little task. So what about you? What are the roles that you want to get rid of and keep yeah? I feel like I go through a lot of different eras, and like right now, I don't know. Right now, I feel like I'm really enjoying like the leadership role. Like, we hired an interior designer and she's been amazing. And I was really worried at first to like outsource that, but after like getting on the first call with her and like her presenting me her design and me being like, love that, change that, swap that with this, and then I get to get off the call and just like go on with my day. I'm like, wow, yeah, yeah, wow, like that's it, I'm done. Yeah, so I feel like it was I feel like I'm a little I felt like I was more controlling than Skylar, but I feel like after that one experience, like realizing how much could come off my plate, I'm like, I'm never going back.

SPEAKER_04 15:44

Like, yeah, it's incredible the excuses that we will make to not shift into that new level. I was talking last night to some of the Wayfair girls, and I just like love taking a peek inside of corporate America, you know, because we're so far removed from it that you almost forget. And I was telling them that, like, you know, when we left corporate America, I could not understand why anyone would stay in it. Yeah. Like it just, you know, I was so certain that this was the path that everyone should go down. And now being an entrepreneur for as long as we've been, I'm like almost fantasize about corporate America. And it's exactly for that reason that you're saying of the satisfaction of checking off the list of things that you are so familiar with doing because you get to do them day in and day out. You become an expert at this little set of skills, and you're not required to consistently, week after week, month after month, completely step into a new role, take on new things, learn how to do something that you've never done before. And that portion of it that I was so certain was like, it is no longer a part of my fantasy. I'm like, it is constant learning new things, and I will make every excuse in the book to just stay in the comfort zone of I know how to do this, I don't want to outsource it. These are all the reasons why I can't outsource it. But then you get someone good and you're like, oh, this is great.

SPEAKER_00 16:59

I just got to a point where anything that I was running into that I was having trouble with, or I was like, there is absolutely no way that I am the best at this. Yeah. There's just no way because I'm awful. So I was just like, that gave me the motivation to like go find somebody that was.

SPEAKER_04 17:20

You're so good at leaving your ego at the door.

SPEAKER_00 17:22

Oh yeah.

SPEAKER_04 17:22

You are so good at leaving your ego at the door.

SPEAKER_00 17:25

It's so easy to just go, I'm not any good at this, and there has to be somebody better. And it's now my job to go find that person. Yes. And manage that person. Yeah. Yeah. I yeah, I'll check that ego right at that door.

SPEAKER_03 17:37

I had that same realization because when we I love designing and I love creating the designs, but then like we're at the project and the photo shoots tomorrow, and I'm running to Target. This room doesn't have curtain, I'm missing four pillows, and I'm like, maybe I am good at the visual part of design, but like this is not scalable. Like, this is a little bit more. I'm stressed listening to you. Yeah, this is not good.

SPEAKER_00 17:57

Yeah, we all have PTSD from that right there. Exactly. There. Game game data there.

SPEAKER_04 18:04

Well, you guys have created a stunning portfolio, right? Like for the love of upstate, anytime that I show it to people, anytime that other people talk about it, like the aesthetic of it is what people know it for most. You know, like you have created a portfolio of properties that is just unique in that way. And so I want to know, even though you've created this really sexy, beautiful, Instagrammable, photogenic portfolio, talk to me about some of the unsexy side of bringing that to life. Oh gosh.

SPEAKER_00 18:35

She just mentioned the photo. Don't talk about it actually.

SPEAKER_04 18:39

Well, you've got to have been like, you know, you're in this phase of building this thing and you're living in the properties. You're like, even though it's coming across as like this clean polished thing, we have gotten to see some of the back end of that. And so I I want to be able to like give people a peek into the reality of what it takes to bring that to life. Yeah.

SPEAKER_03 18:57

Oh my gosh. I feel like the only sexy part about it are the photos. Literally. Or like from photo shoot day onward. Yeah. But even then, it's like the days the guests check in, hopefully. Yeah. They're still looking back then. Yeah. But like it's really, yeah, it's been extremely hard. We we spoke at level of realisting yesterday, and we mentioned if we knew what we know now, I don't think we ever would have started this. Because we definitely had like ignorance is bliss, and we had no idea what we were getting into. Like, absolutely none. And now that we know the ins and outs of how hard it was and how many sacrifices we had to make, how inconsistent the income has been, like the stress of managing other people's money, I don't know if we would decide to do it again. But Skylar also mentioned at the same time we don't regret doing what we did. Yeah. Right. But it was, I'm glad we did it when we didn't have all the information. But yeah, I think the the hardest parts have been, gosh, it's everything. So I'm like, I don't even know. What would you say?

SPEAKER_05 19:55

I would, I mean, I would say from the polished look of it, yeah. I mean, there's a lot that goes into, I always talk about like construction, a good example is like what's underneath the tile in the bathroom, right? Like that is not the sexy stuff. But if you get that wrong, like what's the point of having the beautiful tile? You know, yeah, um, so I think a lot of times when we are putting so much money into these houses, 99% of the money that we put into it, you don't even see, you know. And so I really think from the uh investment side of it, we've been really trying to preach when anyone talks to us about design. It's like, unless you're really hitting those like structural components first, which I know is not sexy to talk about at all. It's like, what's again, what's the point of making it this like beautiful home? So when we're dealing with these old houses, like that is mostly where my focus is and Maddie's focus and our designer's focus is like, okay, how do we also make these things look pretty and have enough money to also make them look pretty? Yeah. When we need to drill a brand new well because we didn't know a house at a well and all of these types of things. So, you know, there are things that we always have to um fit into the budget, which actually will pay us back more so than making them beautiful as well in the long run.

SPEAKER_03 21:04

Yeah, I think overall for me, like Skylar's really good about managing that side of things to like make sure I'm not blowing all our money on wallpaper and then we have like crabby water pressure. Yeah, but it's also been a little bit of a curse, like being so in tune with the aesthetic, because we I've gotten myself in really precarious situations through that where maybe we've spent all of our budget, but I have a really clear idea of what I want a room to look like, and then I start spending my own money. Yeah. Because I'm like this is I feel like my aesthetic is so tied to like me as a person, which I don't know if it's probably not great. But because of that, yeah, I'll put everything on the line for the aesthetic. Yeah. And then Skylar's like Skylar's like, what are you doing? Like, we can't spend our own money on every property to make it look exactly how you want to do it. And so that's been an ego thing for me. I think is like separating myself as a person from what I create. Yeah.

SPEAKER_02 22:00

Yeah. Yeah. Wow.

SPEAKER_04 22:01

No, that's so real because I think that like you guys are so professional in the way that you present yourself to investors, in the way that you show up online. Like, and and I think for a lot of people, they're assuming when they look at these this portfolio that you've built that it's like they've got their numbers dialed in, they must have their budget dialed in, they must have their GCs on this strict scale.

SPEAKER_02 22:23

No stress.

SPEAKER_04 22:24

Yeah, they must understand what to look at on all these properties to know what they're getting themselves into, you know. Like they've got this thing like down to an art. And the reality is that you're reaching the end line and you're like, I still need another 15 grand. Yeah. Like I still, I just not only spent all of my time, but now I'm also spending my money to then have to pay it back to investors, you know? It's yeah, it's not sexy at all.

SPEAKER_03 22:49

It's not, it's not. And I don't know if that's like the right thing to do, but I think we felt, and I say we, but I feel like I felt like I'm the one who found the deal, put together the numbers, like made this plan. If I need $10,000 to $15,000 more because of choices I'm making for my aesthetic, I can't ask them for more money. Like they're gonna be like skip the wallpaper and like maybe get cheaper throw pillows. And I'm just like, that's not an option for me. So, like, to get through this weird era, I'm gonna spend my own money and like justify it as like a marketing expense, you know, because I'm spending this, the photos are gonna be better, the next investor pitch tech is gonna be nicer, my Instagram posts are gonna do better.

SPEAKER_05 23:29

Yeah, there's been like a lot of justification for the Rocky situation, which I don't think it's necessarily a bad thing, like it has caused stressful nights for us, but in terms of like we got actually a uh question on stage yesterday of like, what's your guys' like skin in the game? And we don't put any of our own money. We put our own money into one of the eight deals so far. Our first one. Um, but I almost like don't like that question because it's like our skin in the game is like literally anything this house needs. We are not gonna come asking for more money, we're not going to come ask for anything else. This is what we promised you guys, and if we go over budget or we have to do extra things, like that's our skin of the game.

SPEAKER_02 24:04

Yeah, yes.

SPEAKER_00 24:05

Also, our skin in the games, you come to it. Like you come just do one. Yeah, you'll see our skin really fast. 100%.

SPEAKER_04 24:12

Yeah, you're like our literal skin. Actual skin.

SPEAKER_00 24:15

Not money, actual skin. Yeah, yeah.

SPEAKER_04 24:18

Well, and I think too, one thing that um really speaks to how you guys have built this is now we're at a point where we've got investors who are reinvesting the money that they've made from this back into this. And that is something that is the loudest testament to how good this has gone or how their perception of how this has gone. Yeah. Um, and so I just think that like you guys have created something that's extremely professional. They're not, in my opinion, when I am thinking about from an investor perspective, what they're getting with investing in for the love of upstate, they are investing in this portfolio of properties, but they truly are getting you.

SPEAKER_02 24:53

Yeah.

SPEAKER_04 24:53

And I don't think that investors really understand that when they're walking into it. They're looking at the portfolio, they're looking at the numbers, but it is like it is your baby. You said that on stage yesterday, and I'm like, you guys treat it like your baby. Like, this is not something that you're like, it's not that serious about. Like, I have this, it's not that serious personality, and that gets me into trouble sometimes. But this is you're like, no, this is serious. Like, this is we're putting everything on the line for this. And so I just think that like for investors, there is no safer place for their money to be because you guys would literally rather die than go. Literally. So, literally.

SPEAKER_03 25:28

That's always been when we did our first deal. I remember we were in LA and people we were doing like some mock interviews and like trying to say, like, what would you say to convince someone to invest with you or not convince, but to portray the kind of person you are to like hold on to their funds. And I remember just like thinking or saying that like I would sell my house, sell my car, bankrupt myself before I let anything happen to your investment. Because I tie it so much to like me as a person, yeah, I would do I would go bankrupt myself before I let anything happen to like someone else's money. I feel like we take it too seriously, like honestly, to the detriment of our of our own finances. Let me start that again. To the detriment of our own finances, like sometimes even our relationship, like having arguments about like how we handle this, but we really do take it very, very seriously.

SPEAKER_04 26:22

Yeah. Yeah. It's like having the world's greatest financial advisor on your team. You know, it's like you need someone who like feels like it is their own and you guys embody that. Yes. It's really intense, but I'm really proud of you.

SPEAKER_00 26:34

Yeah, yeah. I think we mentioned somebody mentioned to us the other day, or maybe it was us talking to one another, but we had mentioned that like short-term rentals, although of course they pay, it's hard. Like it is difficult. And so it, you know, it's just one of the things that like if we can make it through building this short-term rental business that we're building, it's like I literally think we could do anything. Yeah, yeah. Like, we've done one of the hardest things, in my opinion, out there.

SPEAKER_03 27:03

Yes.

SPEAKER_00 27:03

And so, whatever's next for any and all of us, I just think that it shouldn't be near what we've got.

SPEAKER_05 27:12

We picked like real estate, a hard industry, and like one of the hardest things to you. Yeah, it's sort of sick.

SPEAKER_02 27:17

Right. Yeah. Love that for us.

SPEAKER_00 27:19

Yeah, we we we did the hard thing first, right? And so hopefully moving forward, everything else should be significantly easier. It's gotta be. Hopefully, that's what I'm holding on to, at least.

SPEAKER_04 27:29

Yeah, it could be the internal optimist.

SPEAKER_00 27:32

I have nothing left to give.

SPEAKER_04 27:34

But I do remember something that I go back to that you said probably three, maybe four years ago at this point, is we were, I think we were in the Hamptons and we were having a conversation about like playing this out and us understanding that we were in a spot where we were taking on debt for these properties, student loan debt, credit card debt, we'll have months that are a ton of success and have months that were like literally, how are we gonna pay rent? And I remember you specifically saying, if we are not unreasonably wealthy at the end of this, something in the world severely went wrong. Like, there is such a small chance that that is not the outcome of this effort. And that's something that I constantly think back to every single time we hit a brick wall where I'm just like, This is it, you know, is this worth it? Like, you know, do we just go back to getting W-2s? Because we have had conversations with you about fantasizing about W-2s now, yeah. And like really being like, Are we absolutely crazy or is this gonna be worth it? And I always go back to that sentiment of like, no, Maddie's right, Maddie has to be right. Like, we are going to be unreasonably wealthy because what other options? That's right.

SPEAKER_03 28:43

We've really, really held on to that too. Like, I think no matter how bleak things have looked, because we have had months where we were like, I we're gonna pay rent late this month. Yeah, because we put everything on the line for these properties, and through all of that, like we've never wavered from that belief that I don't know how long it's gonna take. And hopefully it doesn't take any day now much longer. It could be tomorrow.

SPEAKER_02 29:07

We're ready. I'm ready, yeah.

SPEAKER_03 29:09

Universe, I'm ready whenever you are. Yeah, catch me working. Yes, we've always held on to that faith.

SPEAKER_04 29:16

Yeah, you have to, like, what other options?

SPEAKER_03 29:18

Yeah, what other option do we have, honestly?

SPEAKER_05 29:20

Yeah, I feel like when we've talked about it too, I feel like recently, like even me, someone who we talked about the two boats on stage yesterday, too, like really difficult, but you're crazy enough to still stay in it, or like you don't, you this was horrible. I never want to do this again. But every time I think about going to get a job, I'm like, I don't know if I could look myself in the mirror the next day when I accept the job, like, hey, I'm done with this company. Yeah, I'm walking away. Like, I I know I wouldn't actually be able to do that. Yeah, literally.

SPEAKER_00 29:47

So I'm currently, like I mentioned to you guys, applying for some high-ticket sales positions or for a job. And uh, you know, you start thinking about going back to work for somebody, and it's like the first question they ask you is like, like, can you work nine to five? And I'm like, every day? Like, I don't know, I can I can give you a day or two, you know, but like, no. And so that's just that re-reminder, just that question of somebody asking me that. I'm like, never mind. It's all worth it. Yeah, never mind. Yeah. No, I can't.

SPEAKER_04 30:25

Yeah, you are so quickly reminded of like the benefit, even with all the struggle of choosing to be an entrepreneur.

SPEAKER_00 30:31

I'm good, thanks. I'd rather work my 6 to 11. I'm good, thanks. So funny.

SPEAKER_03 30:41

I I feel the same way. We do have one friend, her name's Steph, and she just recently transitioned from like, she had built one company, sold it, built another company, and we're just kind of like at a point where she's like, Okay, I did my dream twice, and now I have all of this like knowledge and expertise, and like I'm financially stable, I'm gonna go work for someone else's company, like in a mind frame of like help them make their dreams come true. And I do feel like maybe in like 10 years, like I can see myself doing that, where like I did my whole shebang, and now I'm like financially secure and have a lot of knowledge and could like see myself doing that in a way to give back to another person who has a dream. Yeah, that's great, and to no longer have to carry the weight of it being all on you, yeah, and like being able to like take a vacation.

SPEAKER_04 31:27

We've done a few of those. So real it hurts. The last question I've got for you guys if if you guys could go back to younger Maddie and Skyler and give them a piece of advice, what would it be?

SPEAKER_05 31:42

Don't do it. No, no, it would be have patience, I think. Like, I we're so impatient. It's ridiculous. Um I feel like we have every single month like why the hell do we not have this amount of money in our bank account yet? And so it's been a struggle to build the portfolio, but it'd be so long tail of, you know, we always say, like, oh, retirement's kind of taken care of now, but like now I want money now. Yeah. And so um having the patience to just like get through those times, I think is what I would say.

SPEAKER_03 32:18

I would agree. I think that's a big one for me. And then also, I think it's a very similar thing, but this is gonna take a lot longer than you think. Yeah, I think it's the main thing I would tell myself. And then I think I also, and I tell this to people a lot if they like come up to me and ask me, like, oh, do you think I should quit my job? I wish I would have stayed at my job longer or like saved to have a nest egg for us to build this because not only did we have the pressure of like building a business and making sure that was successful, but that business literally paid for our groceries. So, like the pressure I feel like was doubled because we had to build this for building a business and we had to build this so we could survive. And so I think had we had a nest egg or like some other source of income that was covering our basic living costs, we probably would have be been able to build a little bit differently and have like a better experience building the business.

SPEAKER_00 33:08

Yeah, yeah. I don't know if my algorithm, if it's just that or if you guys have been noticing, but here lately it seems like everybody's been saying hold on to your job a little bit longer while trying to get into the entrepreneurship game. And I thought that was wise advice because it's easy for us to just say see you. Literally, we all did that. Yeah, all figured it out, goodbye.

SPEAKER_04 33:29

Well, and now we're all paying the consequences of it. Yes, you know, it's like I I don't know if you guys feel this way, but I feel like we did it backwards. Yes.

SPEAKER_03 33:37

Oh, 100%.

SPEAKER_04 33:37

Not only from like a difficulty standpoint of like, you know, short-term rentals just being one of the most complex forms of real estate investing, but it is a long-term game. And I think that when we first entered into the space in 2019-2020, the narrative online was that this was both the long-term and the short term. Like this was gonna make you rich and it was gonna make you wealthy, and that just is true to an extent. You know, it's like a little true, but it's not the full truth. Yeah, and so I feel like we did it backwards in the fact that we were like, real estate's it, it, it, it, we sold the insurance company, and then we realized immediately we were like, wait, we had this cash flowing thing that was like paying us 10 grand a month that like took very little effort, and like now it's gone, you know, and now we're left with just the income from the real estate. And I don't know, it's just one of those things where if I could go back to my younger self, I would have been like, focus on the cash flowing business first or keep the high W-2 longer and then pour all of that money into real estate, and that just wasn't the approach that we took. None of us took.

SPEAKER_03 34:40

Yeah, we were just very impatient, and like the dopamine from like, I quit my job, like I'm full-time in real estate, but like, can you pay your rent?

SPEAKER_00 34:47

No, okay, we don't go there. That's none of your mistake. I don't have a house, but I just bought a house. Yes, yeah.

SPEAKER_05 34:59

Yeah, yeah, sorry.

SPEAKER_00 35:02

Maybe one of these days. I think I was talking to Patrick the other day. Yeah, and he no, no, no. Patrick, me, and Fede were talking, and uh Fede was telling Patrick that he bought a house that he just moved into, and Patrick was like, wait, are you gonna like short-term rent it? And Fede's like, no, I'm just gonna live in it. He's like, Oh, whoa, we're not there, dude. Now we know you've made it. Yeah, yeah. No guests at your house. Wow.

SPEAKER_04 35:29

It's not a construction zone.

SPEAKER_00 35:30

I know. Right?

SPEAKER_05 35:32

There's no guest house, nothing.

SPEAKER_03 35:34

No idea.

SPEAKER_04 35:35

No idea.

SPEAKER_00 35:36

You don't live in the tiny one.

SPEAKER_04 35:39

There's not a man in the driveway because it's dead.

SPEAKER_00 35:44

Literally done it.

unknown 35:45

Oh real.

SPEAKER_04 35:49

It hurts. We're laughing, but it's like drama dumping your screenplays.

SPEAKER_00 35:57

Well, this was excellent. I'm so glad we came on and did that.

SPEAKER_04 36:01

Well, guys, thank you for coming on and chatting with us. Thank you for sharing a little bit of the behind the scenes that isn't so sexy, even though the portfolio that you have built is. Um, my shout out to you guys, as always, is if you are listeners and you have experienced a lot of this pain of bringing these BBs to life, and you either went back to your W-2 or you built another business, or you just don't want to continue being involved in the day-to-day, as someone who has been on projects that investors have invested in that have gone poorly, and projects that have gone well, your money is safe with them. Like it just is it's one of the most well-put-together portfolios and investor experiences that I've ever seen. You guys should be super proud of it. People who are considering investing in it should not hesitate twice to do it. So I just want to give that plug at the end for you guys because it's just a huge testament to the amount of sacrifice that you guys have put in to build what you've built. So thank you. Thank you for coming on. Thanks for having me. Yeah, thank you so much. Absolutely. And to our listeners, thank you for listening to another episode.