Rachel Evans [00:00:00] I would say the number one thing to take away from this is get QuickBooks if you don't have it. And if you do have QuickBooks, then get a good bookkeeper. Those are the two best things that you can do to set yourself up to really act like the CEO of your business rather than essentially trying to learn and manage a whole business of your finances in itself.

Madeleine Raiford-Holland [00:00:22] That is amazing advice.

Hey there, I'm Madeleine and welcome to The Luxe and The Short of It podcast. I'm a military wife, mom, and entrepreneur that went from a stressed out nine-to-fiver to now a present-minded seven-figure business owner and investor, all through the power of short-term rentals. Here we believe the Luxe life means having the time and financial freedom to be present for the moments that matter most. And I'm here to teach you the exact mindset shifts, insider expertise, and business strategy to make that a reality for you today. So are you ready to actively create the life you want? I'm Madeleine and this is The Luxe and The Short of It podcast.

[00:01:10] Welcome back to this episode of the Luxe and the Short of It. Today I have a very special guest, my CFO, Rachel Evans. And one of the things I love about Rachel is she actually came to our mentorship program as a client. That's how she started. She has been a short-term rental host, so she understands the inner workings of it, but has a wide array of background in bookkeeping, accounting, and all the things necessary to be a CFO. So she understands the inner workings of all of my businesses because she runs all of the money through that. And I say that she is my money boss. Period. End of story. I don't do anything with money. She handles it all for me. So I wanted to bring her on as an amazing resource for you guys so that we could talk through because we're coming up towards the end of the year. We're recording this about mid-November. And I wanted to give you guys, one, the rearview mirror of what we have done in our business this year, monthly, quarterly, annually, to make sure that we are prepared when tax season comes, but also give you the foresight into the things that work for us and the things that we are taking with us into 2026 and the things that we are leaving behind. So without further ado, Rachel, thank you so much for being here.

Rachel Evans [00:02:32] Thank you so much for having me. I think Money Boss is my favorite title of all.

Madeleine Raiford-Holland [00:02:38] I love that title for you. And for a while there, when Rachel first started with us, she was coming in and just auditing everything which is what we love. We teach it as part of our mentorship process. We figure out what's going on, where you are, and where you want to be. And she did the exact same thing when she came in with us and figured out what was going on. And she was auditing a lot of our expenses and figuring out where the leaks were in our bucket. And for a while, we were saying she needed a sign that she could give me that just said, "Rachel says no.".

Rachel Evans [00:03:13] No more spending.

Madeleine Raiford-Holland [00:03:17] No more spending. If you need this, Rachel says no. Rachel says no. So she takes on the role of good guy a lot of the times because she always has the fun conversations about people getting raises and compensation structure. But she also gets to hold up the sign that says Rachel says no quite a bit. So tell folks a little bit more about you.

Rachel Evans [00:03:39] Yeah. So I am born and raised in North Carolina. I got my accounting degree from a small private school and started right out in my accounting career. I always had this pull towards real estate, short-term rentals. I had some family ties and all of that. And so it's kind of always my dream to somehow incorporate my business acumen, my day job with this short-term rental dream. And I found you after having gone through a couple of different programs, which is I always tell people like just save yourself the heartache. Do Madeline's program first because I think I had already paid for like two other programs and I didn't even have a property trying to figure out how to open a short-term rental. So I found you on Instagram and just absolutely fell in love with the program. And at the time I was working in a finance job. So I have a unique combination of accounting and finance background, which is accounting is backwards looking. It's looking at what's happened. Finance is looking forward. It's looking at projections and what might happen. And so it kind of put me in a very unique position where I could not only look back at the history and say, okay, here's what's been going on in the finances, and then to also be able to help create models and charts and predictions of what might be happening in the future and steer us in the way we wanted to go. So while I was doing your program, we started talking and I'm like, hey, I have this experience if you ever need it. And it just completely worked out. Of course, just a wonderful combination of being able to come on and have that background knowledge of what it takes to, what kind of money you're spending in the short-term rental space, as well as just the overall finance knowledge to be able to say, hey, this isn't okay. This is what your current bookkeeper is doing. This is not a great thing. And then we can fix it and do things differently in the future.

Madeleine Raiford-Holland [00:05:48] I so appreciate that about Rachel because it is just such a beautiful combination of two skill sets with the accounting looking backwards and the finance looking forward. And it's been an absolute game changer across the board in my businesses, having Rachel come in and be my money boss because quite frankly it's not my zone of genius. And what we always say is figure out what you love and outsource the rest. And Rachel loves all things accounting and finance and money. And I would just rather have somebody tell me this is what you can spend. No, you cannot. And it actually has been pretty revolutionary in the way that John, my husband, and I work together in our business and have Rachel come in. And John credits Rachel quite a bit for the improvement in our relationship. And I think I'm having John on the episode next week. So you guys stay tuned because I'm sure that will come up in a part of our conversation of how we figured out how to work well together. And Rachel has truly been instrumental in helping curate an environment that works well for both me and John as business partners. So I was going to go a different direction with the monthly, quarterly and annual thing, but I think I'm going to hold off on that a little bit because you alluded to it a few minutes ago with figuring out what my bookkeeper was doing wrong. And the importance of setting it up the right way from the beginning and not having cleanup bookkeeping. So you have free reign here to give the good, the bad, and the ugly, but talk a little bit about what you came into when you came into my businesses and my books and that giant cluster, if we're being frank.

Rachel Evans [00:07:44] Sure. Yeah. Well, I think it's a testament to how a lot of short-term rental hosts start out. It's you're just trying to keep the lights on. And so if you have the luxury of hiring a bookkeeper, you're hiring someone that you hope you can trust, but maybe you don't know a ton about them and you're hoping that they have things covered and you're just kind of plugging away. And a lot of times I feel like what happens is a bookkeeper maybe they're super busy. That happens a lot of times. Is that bookkeepers get a ton of business and they all have to produce statements at the same time every month. So they get so busy with so much work that they don't have time to really dive in and ask the right questions. And sometimes you get people who don't necessarily know enough about short-term rentals to actually be doing your books well. And so one of the things that you and I talked about is, hey, if you're not getting monthly financial statements from your bookkeeper, that is a big fat red flag of something's not happening. Because if they were doing their job correctly, they would be reconciling your accounts, making sure everything was clean, and then submitting essentially a final product to you for review. And that would be how you would keep tabs on things and make sure that everything was categorized in the right place and that you were actually able to use your financial statements to make decisions for your business and understand where your money was going. So that was one big red flag I feel like we came up on. It doesn't necessarily mean that they're doing anything wrong, but that's the first thing I want to see, is that you're getting monthly financial statements so that you are able to review what's going on. And so, yeah, once we kind of dove in, I just feel like it wasn't anything terrible, at least not at the start. It was just like, hey, this could be so much better. And I think that's another place that bookkeepers sometimes fall short is I very much believe in a managerial style of accounting where your books are actually useful to your clients. And so some bookkeepers are just like, hey, this is where it's supposed to go and this is where we put it there. But if your statements aren't actually helpful to you in making decisions, if you just have one big fat bucket that says property expenses and you have no idea what's in that, then they're not really going to do anything for you. And sure, maybe will it be okay for taxes? Great, but you're not able to make educated decisions based on that kind of information. So that's one of the things that we also did is we started talking about like, hey, how do you think about your business? What expenses are you spending on and how would you like to see them split out so they make the most sense for you? So I feel like we really went in. We did have some cleanup work to do. Just stuff of not asking the right questions, not getting all of the information, not being up to date on what they should and shouldn't be doing kind of thing. But the big thing we did is we made your statements usable for you so that you could base your decisions off of what had been happening in your business.

Madeleine Raiford-Holland [00:10:55] And I think that is massively valuable. And to be clear, we're not talking necessarily about owner statements because the bookkeepers that I had at that time were not even doing my owner statements for my property management clients. I was still doing that aspect of it. So that portion was reconciled, but what wasn't was the actual books of the company itself. And so I wasn't able to make really clear decisions on which properties were profitable versus this expense looked like it came into this property, but it actually came from this one because the bookkeeper service wasn't attaching them appropriately, and I didn't have a lot of visibility. And being able to track that revenue year over year, month and month, we could track the top line revenue very easily. That book was fine, but what we weren't capturing very well was, okay, this one has this much more maintenance expense than another. Or we're going through supplies at a rate like twice as fast over here versus the other and the difference is the cleaner. And being able to make those small decisions that add up to big profits differences have been huge. And it's one of the things that I really appreciate about Rachel. And the thing that I do want to notate here is I was not being like cavalier or reckless with my choice of bookkeeper. I am big on the Profit First method of accounting. You guys heard me talk about that on the relay financial episode several episodes back, three or four back. And I love the book Profit First as far as accounting goes. And I went on the Profit First website and hired somebody who was a certified profit first professional. I went out of my way to find somebody with that additional certification and not just a bookkeeper. And the challenge was because I had so many different businesses. So I had the property management company, I had the individual properties inside of that. So some entities own the properties, but they are all clients of the property management company. So money's flowing in different ways. And then of course I have the coaching business. And then I have an influencer and content creation business outside of here. And it all weaves in together. But for most of you guys, you will probably have a property management company. And then you may have individual properties that are held in other LLCs beyond that. And that's the extent, but that is still complex for somebody who is not familiar with short-term rentals and how those businesses can be structured. And so the bookkeeper that we were using felt like they had one piece of the puzzle, and then we had another bookkeeper for another aspect. I think we were using-- I forget even the name of it. But Rachel came in for me and looked at it all holistically and how it all was intertwined in the flow of money back and forth. So very specialized, but also helping me understand the flow of the money and where we could optimize and where we could spend, where we could save. And it was really a beautiful thing. So what are the top three to five things that you would recommend somebody ask when they are looking for a bookkeeper in the short term rental space?

Rachel Evans [00:14:29] Great question. I feel like, number one, do you have any experience with short-term rentals? There are a lot of businesses that bookkeepers can get by on without having necessarily any industry knowledge, but short-term rentals is not one of them. Understanding how short-term rentals work, how the income comes in, when to expect it, what the different property expenses may be, the fact that you might have might have different properties for different expenses, different cards for different properties, all of that. I would ask some questions around their attention to detail for example. I feel like that's one thing. There are the bookkeepers who just want to get things done, basically get it off their plate. And then there are the ones who are determined to getting it right. I think that really sets things apart. So finding someone who is asking you like how many properties do you have? How many bank accounts do you have? What bank account ties to which property? And actually putting all of that information down and keeping track of it because that's going to be really important for them to not have to ask you questions later.

Madeleine Raiford-Holland [00:15:39] Great, great advice there. The other question that we get all the time are what are our technology tools that we use inside of our business?

Rachel Evans [00:15:51] Yeah. I have always recommended QuickBooks. Number one, it's fairly easy to get all of your bank accounts and everything linked in. They are the industry leader for a reason. But also most CPAs work with QuickBooks. And so it doesn't even require you to send your financial statements to your CPAs. They can just log in and get it themselves. So that's super helpful. Always recommend. There are lots of options, but QuickBooks, I still think just hits the top of the list. VR Platform is the other software system that we use. I believe it's actually moved to being called VR Trust now. But essentially it helps bring in all of your listings and all of the different softwares that you use for your listings into one place to help automate your accounting. So I definitely as many properties of you as you have, Madeline, like we definitely would not make it without a VR platform, VR Trust, because it pulls in our property management system, it pulls in Airbnb and VRBO and all of the different ways that we get bookings, and it puts it all in the same place and then says, hey, you also got paid for all of this. So it helps us reconcile those owner statements at the end of the month to make sure that we've covered all of our basis, we've looked at all of our income and expenses, and we know that it's correct. So those are the top two.

Madeleine Raiford-Holland [00:17:17] Love that. So you mentioned in there-- and this might be a natural segue for like our monthly, quarterly, annual things that we do. You mentioned the CPA can log straight into QuickBooks and see what that is. And we also talked about having that document at the end of every month, the statements of the business and what it's doing, and the fact that the accountant can see that. What are our team members on the money team for us? And what are we doing with each one of those parties on a monthly, quarterly, annual basis?

Rachel Evans [00:17:54] So I typically tell people you need at least three people on your team. You need your bookkeeper who is in charge of putting everything together and reconciling it and making sure that your financial statements are prepared on a monthly basis. On top of that, you need your CPA who is going to actually file your taxes at the end of the year. You need someone who's familiar with the tax law, can actually file it, ask all of the right questions. And then sometimes your CPA and your tax strategy can be the same person, but more often than not, your third separate person is your tax strategist. And that's someone who is looking forward. So not necessarily just filing your taxes, but looking at what's your estimated income for the year. How can we strategize to reduce your tax liability? Does that mean, hey, you've got so much income on your books right now, we're expecting you to bring in tons, so maybe we need to go buy a new property. Maybe we need to spend more on renovating a current property so that we can type that as a tax write-off. Those are the top three people that you really need on your team and in your corner. Monthly, that bookkeeper again getting your financial statements to you, checking in with your tax strategists at a minimum quarterly to just say, hey, here is our expected income. What are we planning? And even that ramps up more to monthly towards the end of the year for us as we're constantly checking in. I may even just send over our financial statements to our tax strategist of, hey, here's how the books are looking. What do we need to do to make sure that we're paying as little tax as possible?

Madeleine Raiford-Holland [00:19:36] That's such valuable information. So I want to go back a little bit to our monthly owner statements because we were talking about how you prepare the full financial statements, but we also have owner statements. And I know we have quite a few property managers who are listening here and thinking, "Do we have multiple cards? Does each property have a bank account? How are we keeping track of all of that regularly?" And do you want to go through our system of how we have the property management company and then how we work with our VAs to keep everything neat and tidy?

Rachel Evans [00:20:13] Absolutely. So if you can, which I think once you get to a certain level, you have to try your best to afford a VA. Like it will totally change your life. And so having your VA in place, it actually makes your bank accounts and your credit cards a good bit simpler because your VA can track where all of those expenses are going. So if they're going to property A, property B, et cetera. So what we have is we just have our business bank accounts, and then our VA has a card with special limits and controls and all of that. So we have visibility into what's being spent. Of course, Summer is incredible. So that wouldn't be an issue, but just covering yourself. And then we actually use Monday.com to log all of our expenses. So Summer's created some really great boards in Monday.com that have property name, owner, all of the information that you could possibly need. And then by expense, how much was spent, what it was for, a place to upload the receipts, everything. So then at the end of the month, when I go to look at our books, and let's say we've got 20 different charges to Amazon, it could be to 20 different properties. But I can just log into Summers Monday.com board and say, oh, this amount, here's the receipt for it, here's what it was spent on, and it was for this property. And I don't have to ever even ask Madeleine for those things because it's already taken care of behind the scenes. So it works out really well to have Summer and her team who typically take care of the ordering and everything to also be in charge of describing what the expenses were for and uploading the receipt because it completely cuts you out of it. It's one less admin thing that you have to think about. I feel like that's really helpful for all of us.

Madeleine Raiford-Holland [00:22:07] That's really important because it's really hard to nail me down to get answers for those things. Nor do I really care to know that somebody ordered toilet paper for a property in Tennessee or Florida, like wherever. That's a $10 task, not a $10,000 task. And I always, as a CEO, want to be focusing on the $10,000 task. And why I'm so appreciative to have all of these systems in place to make it easy for Rachel, make it easier for the rest of the team. And I know the question that we get a lot of times is, well, why don't you just have a different card for each property? And my answer to that is that works with one property, two properties, three properties, five properties. But five properties and beyond, guys, it gets really tedious keeping up with 10 different card numbers. Like the amount of admin it takes to go down a list if you're ordering supplies for 10 different properties, 10 different orders, 10 different cards, the tracking of that, it's whether or not you want to do the admin piece on the front side with separating it out before or having continuity of operations. All orders are placed on the same card and we keep track of it on the backside. And at scale, we have just found that it's easier for them to have one ordering card and us keep track of receipts and attribute that after the fact. And the bank account itself-- again, we use Relay. I'll put you guys a link down there in the show notes. The bank account itself is the gold standard for reconciliation. So we know how much has come in, we know how much has gone out. And that's where Rachel lives and breathes, is making sure that everything is down to the penny correct.

Rachel Evans [00:23:59] That's it. I feel like the beauty of having the property management company take care of your own properties as well is you can consolidate all of that into that one bank account under the EIN of the property management company. And then we can get into talking about credit card points and rewards and how much better if you can put all of those expenses onto one card or a couple of cards and really rack up those different rewards than having to spread it out and having it on a ton of different cards. And heaven forbid if something happens and you get a random fraud charge on a card, but then you've got to go and change all of that stuff. So especially for like recurring expenses, it gets to be really aggravating. So if we've got one central place and really one person or one location that we track all of those things in, it just seems to make things so much easier.

Madeleine Raiford-Holland [00:24:54] I love that. So we're mid-November at this point. What are we doing from now until the end of the year to make sure that everything is ready to go for 2026? And what is one thing that people can take away from this episode that they can do to start off 2026 on a good foot?

Rachel Evans [00:25:16] So right now I feel like we are hounding our tax strategists. We are checking in almost weekly at this point of here's what we're expecting, what are our moves? We're essentially saying here are the individual outcomes that could possibly happen. Here are the income ranges and tax liability ranges that we're looking at right now. And what are our different options to reduce that? And we're just constantly keeping in contact with him. Obviously still reconciling the books monthly, making sure everything's nice and tight. For those of you who pay contractors as well, we're making sure that we have W9s for contractors, that we have everything in one central place so that it when it comes time to file 1099s in January, we're not running with our heads cut off trying to get that information. We're planning for that right now. I would say the number one thing to take away from this is get QuickBooks if you don't have it. And if you do have QuickBooks, then get a good bookkeeper. Those are the two best things that you can do to set yourself up to really act like the CEO of your business rather than essentially trying to learn and manage a whole business of your finances in itself.

Madeleine Raiford-Holland [00:26:31] That is amazing advice. So typically this is a part of the episode where I tell folks or ask you where folks can find you, but I'm just going to get the elephant out of the room that Rachel is all mine. As my two-year-old says, "All mine." All mine. So as much as I would love to share her with you guys, she works within my businesses as a full-time gig, but she is available in our mentorship. She does twice a month office hours for our mentorship clients and our community to get their questions answered about bookkeeping. So that is where folks can find you. Your Instagram is a private account, right, Rachel?

Rachel Evans [00:27:15] It's not, but...

Madeleine Raiford-Holland [00:27:16] Do you want people to find you there or you want to leave that private?

Rachel Evans [00:27:19] I mean we can just leave it private.

Madeleine Raiford-Holland [00:27:21] Okay, we'll leave that behind.

Rachel Evans [00:27:21] I'm sure they could find me through you if they really, really tried.

Madeleine Raiford-Holland [00:27:25] If they really, really tried. The best way to get in touch with Rachel is through our mentorship, folks. Period. End of the story. Come find her inside of our office hours that she does twice a month. So, Rachel, do you have-- well, I want to ask this question of you because we ask this to everyone. What is a time in your life where change has brought about an unexpected opportunity?

Rachel Evans [00:27:47] Oh my gosh, literally joining your mentorship program has just absolutely changed my life. I really feel like I could be the poster child for join Madeline's mentorship if you're trying to do this.

Madeleine Raiford-Holland [00:28:01] I think you are.

Rachel Evans [00:28:02] Because I really try. I feel like I tried for two years just to even get started, get off the ground. But through that, meeting so many like-minded people in your community, it has provided job opportunities. It's provided friends. I've been to Costa Rica with you on their retreats. These things that you do and you offer as part of your mentorship program would have never come about. It's like a crazy snowball spiderweb effect of all of these different people that I've met, that it's absolutely changed the trajectory of my life. I went from a corporate job and dreaming of short-term rentals and thinking that that could be my way to time freedom, to not only having time freedom through that, but also through an entirely different business. I essentially created a new business because of all of this. And so I feel like it was a lot of change. It was a lot of I have no idea what I'm doing and we're going to figure it out together. But it's taught me that change is definitely not always bad and usually brings something really, really cool out of it if you will let it.

Madeleine Raiford-Holland [00:29:13] If you will let it. The episode a few weeks ago, it can be beautiful if you let it. And I think you are the poster child of letting it be beautiful. So thank you for all of the ways that you have touched my life for the positive. I mean, truly saving my marriage on a lot of fronts. And really just helping me have the visibility to see into my business, know where we can grow, and always being a champion of that and growth. You have been an amazing blessing in my life, and I want to say thank you.

Rachel Evans [00:29:45] No, thank you. It's been a pleasure. It always is.

Madeleine Raiford-Holland [00:29:49] Well, thank you so much for joining us. Folks, any resource that we mentioned, I think we have 30% off of six months for QuickBooks down in the link. We've got some amazing resources with all of the programs that we mentioned. So we want you guys to go into 2026 strong with your finances. And as always, if you have any questions about how you can join our mentorship, you can also find that in the show notes below. Thank you for joining us, and we'll see you next week.

[00:30:23] Hey y'all, if you're loving the show, be sure to hit the follow button or the plus sign on your podcast app to subscribe. This will ensure you don't miss a single episode and I'll see you next week.