PODCAST EP46: Big Announcement: Transitioning Airbnb on Autopilot with Madeline Raiford Holland

Jul 09, 2024

Welcome to Podcast Episode 46: Big Announcement: Transitioning Airbnb on Autopilot with Madeline Raiford Holland

In this episode of the 3 Day Workweeks podcast, I am joined by my longtime friend and business partner, Madeline Raiford Holland. We reveal a major announcement regarding our joint Airbnb venture. We cover our extensive history and collaboration in the short-term rental space, the evolution of our businesses, and our strategic approach to scaling Airbnb operations. We also discuss the importance of systems and processes for efficiency, Madeline's coaching services for short-term rental entrepreneurs, and an upcoming live training event.


00:00 Introduction and Special Guest Announcement

00:29 Madeline's Journey and Collaboration with Kate

02:15 The Birth of Airbnb on Autopilot

05:39 Scaling the Business and Personal Challenges

07:42 Transitioning to Full-Time STR and Consulting

12:31 Market Challenges and Strategic Decisions

19:19 The Big Reveal: Course Transition

24:13 Future Plans and Live Training Opportunities



  • Streamline Your STR WorkshopUse code KATE50 for 50% off a VIP Ticket to Madeleine's Streamline Your STR Workshop on July 25th and 26th. 

Talk to you soon!



Owner + Founder, Kate Waldo + Co. 

Creator of the Smarter Not Harder: 3-Day Workweeks for Millennial Entrepreneurs©  Program

P.S. Curious how you can grow your 6-figure business while slashing your workweek in half? Click here to learn about the Smarter Not Harder© program!

Some of our content contains affiliate links which provide us with a commission at no cost to you. Kate Waldo + Co. only recommends affiliates that we know, use, and love. 


Welcome back to another episode of the 3 Day Workweeks podcast. I am so excited to be joined by Miss Madeline Raiford Holland. We have a really exciting announcement for you guys.

We've been itching to tell you for a long, long

Really long time.

But but we're here and we're going to give you a little bit of the backstory and then tell you what's been going on. So, Madeline, welcome.

you so much for having me. It's long time coming.

I know. And for those of you who haven't listened to past episodes with Madeline, go back and listen to those. But a lot's changed in her life and my life since we've talked last. And Madeline is a savant at short term

That's generous.

Thank you.

all the things. It's true. It's true. So Madeline's been, we've worked on a lot of projects together over the years.

It's true. All sorts of things, from her blog as a, like, fashion and lifestyle blogger, to her government contracting business, to an Airbnb course, we've just come full circle,

We have, I think I was doing the math yesterday and I think we started working together in one shape or form of another, like eight years ago, which seems, yeah, we're almost decade long friends at this point.

I know, that's so

I think the statistic is if you stay friends for seven years, like you're stuck with them for life.

So you're stuck with me now, Kate.

Well, we are what do they call it? Partners by now. We're domestic,


domestic business friend partners.

I love it. I love it.

So funny. Well, so Madeline, you are in Athens, Georgia and from Vidalia, Georgia,

Yes. And I had a little stint in Virginia for about 12 years. So I claim Virginia partially as well, but Georgia has my heart.

Yeah, so we met when I was still living in Savannah, not too far from Vidalia, and now you guys probably know I live in Pensacola, Florida, so we are mostly virtual friends right now.

I wish we got to see each other more, but one day.

I know, I know. Let's share with everybody we started on this Airbnb process. Yeah.

in order to come full circle here, Kate and I were working at the time on a project with my government contracting company where I was COO and she had come in and absolutely revolutionized the way that we did all of our systems and digital operations. And so my Airbnb business was an offshoot of my lifestyle brand, Moderately High Maintenance.

I knew that as my short term rental and Airbnb business grew, that I needed to add the systems in place. And Kate obviously came to mind to help me think through that operational side. And so we started working together a little bit on that and Kate saw the success and how fast my business was scaling over there.

Just naturally had an opportunity to fall into her lap to do the same thing down in Pensacola. So at that point, we were like, we have really done some really good work here. The systems, the processes, we're like, nobody's really doing this in the Airbnb space. I wonder if we could teach people how to do this.

Because I was already having so many people come over and say, hey, can I take you out to coffee and pick your brain? And, you know, I, now I always say, you can pick my brain after you pick your payment method. But, that was kind of our mindset. It was just, I don't know, So many people were coming and asking.

So we decided to co create Airbnb on autopilot while Kate was beginning her Airbnb journey, we were like, there's no better time to document the systems, the processes, and really teach how to like go about this while she's, well, I'm essentially teaching her what I've done so far in this process.

Which is a great way to learn because at the time summary of what you had going on in your life, Rhett was like, maybe six months old?

you start your first one before he was

No, I did he was six months old when I started my first one No, he was nine months old when I started my first one. So timeline October 2021 We opened our very first property and then over the next six months We opened five more and I was pregnant with Rowan like in most of the videos where Kate and I were Filming for Airbnb on autopilot.

I was actually wearing the same shirt Kate has on right now. If you guys are watching the video, we have the same shirt, always like twinning.

Blog Societies. I think

Yes, everyone has that shirt. Grayson, I think it is, but I was wearing that shirt and I told Kate, I was like, I wonder if people can tell I'm pregnant because I was pregnant with Rowan at the time.

So yeah, we, W I had like, COO responsibilities, had a new baby, was pregnant with another one. Kate had all of her various businesses going on at the time. We, we had a lot going on. Like looking back, I don't know how we did it all.

You had a lot going on. And that was part of having the systems in place was like, all right, you still have to do your COO job. It's not just a W 2, you were COO, kind of CEO of the business managing a huge team, a huge business with, you know, lots of responsibility. Plus, you had your children, you had baby on the way, and just like, life and family.

So I figured if you could do it with all that going on, teach me, and that way, because you were getting all these questions from people about how do I do it, you recognized an opportunity for an online program where you could say, here you go, this is everything, this is my whole brain,

Just take it.

teaching me, I was able to put it into a, like, online program format



I think it was just one of those situations where it was like, let's just brain dump this entire thing. And

the time it was not really ever my goal to leave the COO position. And my goal was to retire John. So I was like, I have to build this in a sustainable way with the systems and processes in place to be able to.

Not add another full time job to this. This has to fit into the in between moments of life.

Right. And clarification, we both have a husband named

Oh, yeah. That's, I to share.

So yeah, you wanted your John to be able to retire and, cause he was both Reserve Marine Corps and he had a sales

Where he was traveling all over Kingdom Come. I mean, it was, it was ridiculous at that point. We were both traveling in opposite directions all the time. And so we were just like, something's got to give here. And that's, we eventually came to a breaking point after our second. Our second son of just saying, Hey, we've got to, we've got to make a shift here.

One or both.

what changed? What did you decide to change at that

It was kind of an evolution of things. We knew that we needed to get John out of his W2. And so we really started focusing on growing the STR business in a pretty quick way.

Of through this, this process we realized, okay, an online program that's kind of like a static program is great to get you started, but you were having all these people come to you and say, hey, I need more one on one help. I need some hand holding.

I need some direction.

as I was scaling, I was looking for my own education of this, of, Hey, like who's somebody that I can go to, to get like one on one help because there's so much generalized information out there. And so what I found was there wasn't a lot of, there weren't people doing that.

Yeah. You and I are both big believers in working with online coaches, joining online programs to learn as much as possible. So you did that. You

I, I spent over 50, 000,

this stuff is missing!

50, 000 in courses only to be disappointed because it was just very generalized vague information out there that this business is so nuanced. Like it's so nuanced.

It's market specific. You have to know how to take those generalized principles and bring it back down to home.

And if you're like me and you, and like data and numbers, like, it's sometimes hard to extrapolate that and know, like, the art and the science piece of it. That part

have all the data you want, but what does it even mean? Right.

good data? Yeah. Is like, is this a true cop? Which is, which is why you need somebody in your corner.

So I

evolving to, is adding this on to the business of doing this consulting. And in the process, things were really busy with Orchid Organizing, things were really busy with Kate Waldo and Co.,

with all of our courses and programs and coaching and all the things. And then where the Airbnb that we started came into play was John and I were both renting and he had his property and he said, My property is in a really great neighborhood.

Why don't we try? Madeline's having such great success with this and you're learning how to do it, so why don't we try using my property? And so that's what we did. It was a really cool experience and very nice to have that tactile, something to work with while we were creating this program. So, while you were, in the process of going full into STR for yourself, and it, I mean, by spring of 2023, how many properties did you have?

have a 23, I think we were up to 10 at that point. Now we're getting close. Well, by the end of August, we'll have over 15. So we own.

coaching business starting to go

Yeah, it was. It was a lot of fun. It was, it's been a wild ride and the consulting piece of it, I realized that there was a need for it when people were just like, yes,


And it got to a point where


really felt like it was my calling and my passion, because in the, in the, in the middle of all that, John was able to leave his W2. The consulting piece really was just lighting a fire in my soul that I hadn't felt as an entrepreneur in a really long time and being able to help other people and families achieve not only the financial, but the time freedom that we were able to achieve just was the most fulfilling aspect of that whole thing.

And so. While it was never my intention to leave the government contracting business, it was like, this is the right move. Like, this is what I am called to do and teach other people,


achieve that in their life. And so we ended up both leaving our W2s and now we're fully self employed and have that time and financial freedom, which we, we really wanted out that out of that, but it's just kind of a wild ride.

has been. would never have thought that we would end up where we

Right, right

John and I's property kind of just fell into our lap and we figured why not try it, we're in a great neighborhood. Well, there were a lot of factors though that had we gone into this with a little more strategy, we would have considered that we didn't this time. We ended up in a market where over one summer we. Let's see, we decided that we were going to turn his property into an Airbnb around, I think, May. And then we wanted to have it launched by summer and we had it last week in June ready to go. And it went gangbusters, which was awesome. But at the same time over that summer, everyone else had the same idea. Because where we are, there's no laws in place to Prohibit anyone from having an Airbnb literally anyone can do it in the neighborhood that we live in Anyone can have an additional dwelling unit on their property So a bunch of people saw this opportunity and there went from having 4, 000 Airbnbs to 7, 000 Airbnbs in one summer. it was kind of

Insane Insane, and I think that other thing about the time that you guys were getting started We are still kind of riding that post COVID wave and

thing was that long term rental rates

They were starting to come up because the interest rates were coming up.


And so at what point in your situation did your landlords decide to raise the rent on you guys?

Yeah, so if you guys aren't familiar, there's several different ways that you can have a short term rental property. And the way that we did it was we did an arbitrage, which is where you have a contract, a corporate contract, with your landlord and your LLC to, that you're allowed to rent the property as a short term rental.

So that's what we had. And we, we had an agreement with them. But Because of just the world and all the things that were happening, their property insurance went up and so they increased our rent significantly, like 30%. It was just kind of a time where John and I personally, business wise, had a whole lot going on.

We knew that we were probably going to get engaged pretty soon and then shortly after start planning an elopement. And so it really crunched our margins when we had the rent going up like that and we had a very, very competitive market. the stars kind of aligned and Madeline was like, Hey, I've got another property opening.

What if, what if I take everything in your house put it in my property? I'll buy it from you. And we're like, you know what? I think that might

Why the heck not? Well, you know, in our coaching program now, I speak a lot to the different types of short term rental businesses and ways to get into it. And you alluded to that. There's property managing somebody else's short term. Then there's arbitrage, which you guys did. And then, of course, there's owning your own property each one of them has their own benefits.

Owning definitely the tax benefits, arbitrage it's a lot less capital to get in and there's less commitment. But then property management, there's pretty much no capital to get in. But One of the things I speak to now and one of the things I love about arbitrage and one of the ways that I utilize it in my own business is to test out a market.

And we actually did that in the Orlando market to see if we would like it. And similar to you, like we, the property was profitable, but we ended up not buying it. And we ended up really liking the type of guest that our property was attracting. It was a beautiful villa, private pool, five bedrooms, like 15 minutes to the Disney game, but because the market was so competitive, we were always having to compete on price.

And so after a year we said, you know what, we're glad that we tested out the waters here before we purchased. And I think that's a really good perspective to have in this business. And especially with arbitrage is test it out. See if you like a specific market, I'll say, Hey, I'm going to try an arbitrage before I purchase here.

And another reason I like arbitrage is a lot of times when you're in an area that's has really high real estate prices, like even here in Athens, I own and I arbitrage because downtown walking distance to the football stadium has been gobbled up by a bunch of commercial investors and high rises.

Like. numbers don't work. So being able to get into a two bedroom, two bath apartment at a rent that's priced for a college student, those numbers work all day long. So there are different ways to get into this business. And I don't think that you guys did anything wrong or that it was a failure on your part.

You said, Hey, this property is like fell into our laps. Let's give it a shot. See if it's going to be worth it for us to invest longterm. Things in the market shift and you guys had minimized your risk because you hadn't purchased that property in that area and you were able to get out relatively scot free.

Yeah, what was so nice about it was that because you had come up with a way that you do all of your properties where they're extremely well appointed and there's, there's a standard set for everything, we followed that, we created systems around that, and everything was so orderly and standard that it was easy, it was like, it was like you moving one of your own


taking everything from the inside and moving it somewhere else. So it worked out really well. The systems in the organization were a major part of that. And we worked early on on your properties of organizing them. And that was something that you carried into of

It's still part of our brand standard. Like all of the things that you teach in Airbnb on autopilot is still something that we to this day have as part of our brand standard. So. So.

a standard. So

Well, and that's what we talk about is having an elevated guest experience, an elevated brand standard. So you're not competing on price.

Mm hmm. And this is an aside, but the organization, especially having my own property, what I recognize the value of having everything labeled and in, especially having labels, but having everything very organized, having, inventory of where everything was made my job as the host and the owner of the property so much easier because it made everyone else's job easier.

The cleaner knew exactly where to put things back. Even the guests, they would put things back where they go because things were labeled. It made a huge difference.


What a crazy year last year was. This was, like, I don't know, June, that we talked, and we were like, Hey, I think this'll work, let's do a switcheroo, you're gonna buy all the stuff from the house, we're gonna load it up in a pod, and shout out to my husband and my brother in law, and one of my amazing organizers in Pensacola, Everybody was a part of getting that done and packing it up and shipping it to you. And then, what you didn't know at the time was that I was in final negotiations for selling my professional organizing business. you came to me and were like, Hey, I'll buy all your stuff and I have an idea. And so this is where we get to the surprise is that Madeline was like, I am doing all this STR, short term rental, Airbnb stuff, full time.

It's my thing. I love it. It's like the passion that I've found in my life. I'm full time and I'm all in on this. What do you think about selling me the course? And I was like, you know what? I think it makes

it makes sense. And so we started that process of transitioning everything over to my platforms. And,


We're partly here on this episode to kind of tie it with a pretty little bow for our existing students who originally joined us when it was hosted on Kate Waldo and Co. We are finally bringing you guys over to madeleineraifordholland.Com and giving you guys so much more content. I mean, I think


course is Almost tripled with the amount of content that we have completely redesigned. And just giving you guys so many more resources to understand all of the intricacies of all of the different types of ways to acquire best practices for setting it up systems for scaling, making your property shoppable.

We have just fully expanded it from all of our consulting piece because I had the full time energy and now


to devote to building this out. And so we are so excited to bring everybody over into the the new the new realm over here.

Yeah, so it was crazy that it all happened so quickly, like selling three businesses within 30 days. never would have thought, I teased it a little bit, but what we decided was to kind of keep it under wraps until we were ready to get everyone who was in the Kate Waldo and co hosted version of the course over into Madeline's and so we've spent a lot of time, especially Madeline's team, has spent a lot of time building that out for you guys and we wanted to make sure it was 100 percent ready for you before we spilled the beans.

and we wanted you to enjoy your honeymoon and you know, all of the other lovely things that you had going on in the fall.

Yes, so now secret's


it's really exciting. And we wanted you guys to know too on a personal note that Mal and I are great. We are still very much friends. Everything is good.

Yeah. There's no like bad blood.

Yeah. We just wanted some.

No bad blood whatsoever. And yeah, I think it's good to process and do things on our own terms and like make sure that, you know, both mine and Kate's standard of doing business is doing it with excellence and we would never want to rush something for the sake of just like getting it off.

And I want to commend Kate for that because she has done an amazing job of finishing. This well just supporting us through this transition and always like being willing to answer any Kajabi questions or things like that. I mean, she's wonderful at all of the business systems and processes, as you guys know, that's why you're here.

So yeah, it's just been a wonderful, like smooth transition of everything. And we just can't wait to have you guys over on our side of things.

Yeah, we're very excited and it's been quite a process of like things on my end. I think that's something that we're going to do an episode on Madeline's podcast where we'll kind of talk a little bit more about like knowing when it's time to step away. What does that look like? What does that mean? And just know that if you're listening to this, that this is like your permission, not that you need it. But if something's not serving you in your life you can move on from

huge proponent of having that element of flexibility in your business so that you can have it in your life for whatever you've got going on.

I love that. Love that.

Well, Madeline, thank you for being here. What can people expect from madelinerayfordholland. com and your business right now? What are you, what are your main things that you're up

Yeah, our main thing is coaching and helping people start or optimize short term rental businesses and helping them create it in such a way that they not only have the financial freedom, but the time freedom along with it, because

like you said, there's nothing more important than being able to choose how you spend your time.

And our last thing is want. We want is to have people making all this money, but they're being glued to their phone and they're not able to fully direct the way that they spend their time and have habit to spend with what they, what matters most to them. So on our Instagram, we are doing our best to educate people in the short term rental space, but we're also doing a lot of live training, which makes the one on one support a little bit more accessible because people can get on live and, Join a group and have my teaching live with them.

And then we also have a small cohort program for people who already have a property, but want to add those systems and operational efficiencies into their business. And for people who are just like, Hey, I need to make a change. I need to make a shift who were where I was a few years ago where Kate has been in certain aspects of her business of just like, I don't know what it is, but something's got to change.



help people start from literally, I've got this much to invest. What can I do? What strategy is best to me that we help them through the acquisition, the physical setup, and then the digital setup through

one coaching and mentorship. So you guys aren't. In my shoes, we're spending thousands upon thousands upon thousands of dollars with generalized information.

Our students are most successful with me and my team in their corner. So that's what we're focusing the majority of our time on is just spreading the message and saying, Hey, if you're tired of the rat waste, you can make a change. So

Yes, and that's where we always align is like working smarter

harder and having that white space in your life because what's the point of all this if you don't have

Exactly. Exactly. So for those of you who are Part of our original Airbnb on autopilot group. We have a ticket to one of my live trainings that we are gifting you as we celebrate this transition over. So Kate will be sending you guys an email with how you can get a free ticket to one of my live trainings.

If you're ready to take that to the next level and for the rest of you guys, if you are curious about the short term rental space Kate has a discount code for a ticket as well. So. We would love to have you join us. Our next live event is going to be July 25th and it is a one day workshop where we will literally tell you everything like from start to finish for you to explore and see if it is right for you to enter into the SDR space.

Awesome. And we're going to have those linked below for you guys. So you have your discount code and if you want to join the workshop, it's going to be super, super helpful. Even if you're just an ounce curious, this is so worth joining and, and hearing from Madeline and her team about what they do because it is truly incredible. is very, very impressive.

Kate. We'd love to have you guys join us. So

Amazing. Well, thank you for being here. Yay. For the secret


getting to share. Yay.



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