The Remote Host Bootcamp with Hailie Marie Anderson

A recorded webinar session (May 2025) where Hailie Marie Anderson explains how she built a fully remote, scalable Airbnb arbitrage business. She covers automation, delegation, hiring and retaining remote teams, time audits, CEO vs operator mindset, and operational roles; shares her personal background (started at 19, scaled to dozens of rentals) and recommends outsourcing guest communications, cleaning, pricing, and maintenance.
Questions this video answers
22 years old.
19.
58 properties.
A little over two years.
About 20 different countries ("up to like 20").
Chapters
Can we all just say, hi, Hayley, show some love, because I'm really looking forward to this session. Today. We've got 45 slides. Four, five slides to. To really crack on with today. Feddy had 44 yesterday, so we'd be in it by 2. Well done, Hayley. And we're gonna absolutely flow through. What I realized yesterday is it's sometimes you take a little bit to get going with the questions in the zoom. So please don't be shy. There's no silly questions. This is such an important topic because again, so many people struggle when it comes to building a business that is truly one that they feel like can be run like clockwork. And I've gone through the presentation and it is unbelievably good. I'm so glad that we're able to put this to the world. So, Hayley, thank you very much. So I'm going to pass the floor over to your good self. Before we do, can everybody please let me know where you are? Tuning in from around the world. We've had some Saudi Arabia, we've had Dom, Dominican Republic, we've had obviously the us the uk. I'm looking for those lovely. We had Kenya. So worldwide audience. Worldwide audience. Rob's in Florida. Hey, Rob. An's in southwest Scotland. Matt in Michigan. We've got New York, North Carolina, Dallas. Somebody's also dropping in their website domains. I love that. All right, Ms. Haley Marie Anderson, the floor is yours. Thank you for doing this. I'll let you go.
Yeah, well, thanks for having me. I'm so excited. It's the last day, so hopefully everyone is still feeling motivated and excited. But yeah, I have a lot of slides to get through, so we're just gonna start. And if you have questions, don't be shy. There's no such thing as a dumb question. I will answer all of them. So, yeah, let's get started. Today I'm going to be covering how I built a five star business, fully remote. So for those of you who maybe have never seen me before, there's probably three big things. You're wondering, who am I? Why am I up here? Why did Mark asked me to do this and what are you going to learn and what can you expect next slide? So also, I don't have control over the slide guys, so don't mind if there's a little lag. We're still getting the flow together, but this is who I am. I'm Haley. I am 22 years old. I have been doing Airbnb Arbitrage for A little over two years. So I rent all of my properties. I don't own any of my properties. And I started at 19 in high school, and from then I have scaled to 58 properties, fully remote. I basically am a digital nomad. The last four weeks I've been traveling. I've been home for like two days in the last four weeks. So this is completely remote. I am not physically required to be anywhere except where my laptop or my phone is. And with these slides, I'm going to teach you to do the same thing. Life before short term rentals definitely did not look like what it looks like now. I've always had some sort of, like, entrepreneurial spirit, I like to say, but I've worked at Target, I was a leasing agent, I started a yard card sign business in the peak of COVID I've done drop shipping, UGC agencies, I've done it all. But nothing has stuck quite like Arbitrage has for me. And, yeah, it's completely changed my life. So what to expect? There's going to be three big things that I'm going to cover in these slides. First is how we're going to automate. Second is how to delegate. And third is how to scale with all three of these. I mean, you have. You have to do all three to be able to scale successfully. And scaling can be really, really good or really, really bad if you don't do the first two steps. So I'm going to make sure that we cover both of those so you can scale successfully. Okay, this is a little question I have for you guys. If any of you in here do Airbnb already and you already have units, I'm curious, do you operate locally or do you operate remotely? You can put this in the chat and obviously I can't see the chat.
But I will let you know. I will let you know. So we've got a nice mix of locally and remote. I would say it's about 50%. 50. 50, right.
Okay. All right, that's good to know. Hopefully if you are operating locally currently, and you want to, you know, branch out and grow and operate remotely by the end of this, I guarantee you you will. And if you are operating remotely, I guarantee you probably will learn something new as well. So this is perfect. I will ask again at the end of the slides. Yeah, so I don't live where I host, and I think that's the whole entire point of creating a business. I was very adamant on the fact I didn't want to create myself another terrible job that I Hated. So with this job, obviously it's still a job, but I don't have to be tied down to a specific area. This is me in Italy living my best life. And I have traveled. Like, I think I'm up to like 20 different countries. I'm never home, really. And that's just like what I enjoy. If I want to be home, I can be, but this is fully remote. And I think that's the beautiful thing about this. Next thing I want to talk about is CEO versus operator mindset. I think this is something that I've been kind of. I have struggled with in the past before. Everyone preaches, oh, I'm a CEO, oh, I'm a business owner. But there was a lot of times where I caught myself being more of an operator than a CEO. And I think this is a universal kind of thing where you start doing these little things and you're sitting there and you're like, what am I doing? This is taking up so much of my time. I'm being more of an operator in the day to day things than managing and scaling and growing. And I think it's good to recognize when you're being an operator and when you should really be a CEO. And kind of pivoting from that operator role to a CEO role has completely changed the growth and scale of my company. And it's still things I have to recognize now. Sometimes I'll catch myself doing things. I'm like, okay, this can be delegated or this can be automated. And recognizing that is just the first step. And the problem with doing it all yourself, which a lot of us probably either do it all ourselves now or have done it before, are three really big things. Obviously, the first one being burnout. You are just one person. Is quite impossible to do everything on your own. Micromanaging, literally, you're going to catch yourself doing micromanagement for forever. And no one wants to do that. And also limited scalability, since it is just you. There is no way in the world you can reach these big goals that are greater than you alone. You need a team. And the second you recognize that, hey, hiring a team or delegating and automating is not a reflection of my inability to do something and simply the fact that to reach those new levels, you need a team. Every single big company has teams. And if you want to grow, you need a team. So recognizing that is huge. Yeah. So the solution to doing that is to build a remote team to scale. My team is 100% remote. I have team members in the Philippines I have team members in the States. I'm all over the place, but we're all remote, and we run a seven figure business every single day for the last two and a half years. All right, so this is a little reflection. And if any of you maybe have pen and paper or you have your phone out, I highly recommend maybe taking a screenshot of this and doing this later. But I think doing time audits are really, really important. I do these not only for myself, but I also do this with my team as well. So there's a couple of things in a time audit that I recommend you do. The first one is to track your time with this. I recommend setting a timer for like, say an hour, 60 minutes. Set your timer and within that hour start working. Start working on whatever you're working on. And after you're done working for that 60 minutes or whatever you choose, categorize every single thing that you did within those 60 minutes. So say you spent 20 minutes doing guest communications. You spent 20 minutes managing the cleaners. Whatever it is, categorize it. That way you can easily see which ones are your biggest time wasters. And by time wasters, I mean if you spent 40 minutes within this one hour doing guest communications, that is a red flag that, okay, you can delegate this out for cheaper than what it would cost you per your hour, and then from there it makes it really easy to see what you can delegate, and then you can delegate it to someone else and remove it from your workflow. So you could do this for yourself and you can also do this for your team. But I highly recommend everyone to do a time audit. It makes seeing what you can outsource a lot easier than just trying to come up with it on your own.
I've just asked a question in the Zoom chat, and I'll ask it now so we can all start to type this in again. We've got nearly a hundred people watching, which is amazing. So the question is, are you currently doing this? Are you? So this what Hayley's put in front of you, are you currently tracking your time? Are you able to identify, identify where these time wasters are? We've got sometimes new idea doing this. No, but I guess I should be. So this is good. This is really good.
Yeah. That's awesome. Yeah. And like I said, I do this myself too. So everything in here I do myself. And I just. I recognize it's helpful and it's always good to continue doing. Just because I've done it once does not mean there's going to be new time wasters in my business. As I continue to grow and delegate things, there's always going to be new time wasters that I can then outsource again. Great, great, great. All right. Yeah, this is a little question too. I have a couple of these. So I'm sorry, but it's good to get your brain working and I kind of want you to reflect n words as I go through these slides. But what is your number one time waster? It might be easier after you do the time audit, but usually you have an in cling of like what it could be. So it's good to just think about what you probably are wasting the most time doing.
So this is. We've got pricing alignments by hard pricing alignments. We've got lots of other ones coming in. I feel like the number one for me at the present moment in time is going over transcriptions. I have lots of people doing calls on a daily basis and my biggest time waste is going through transcriptions. But, but client reports, customer communications, updating pricing, you name it, it's all there.
Yeah, yeah. And they're all, they're all very value like they're all very real and they all, they all can be delegated or automated in some way to make it take up less of your time so that you can go spend time doing something else, which is the whole goal. All right, so some of the most popular that I hear on a regular basis are a couple of those that you mentioned. And I think these are the four easiest ones to outsource from the jump. So you have guest communications, cleaning, coordination, pricing optimization and maintenance request. These are the four ones that are the simplest to outsource or automate, delegate. And also the most common. Guest communications and cleaning by themselves take up like the majority of my time, my team's time in the beginning, but now I obviously have systems and people who do it for me, but they're so easily outsourced from the jump that you shouldn't be wasting your time doing them. So these are the four most common ones, but obviously as you grow and scale, there'll be new ones as well.
It's so funny. The four that you've put down here on the slides are literally the ones that people have put in the chat. It's like you force shadowed what was coming, which is brilliant.
All right, so next, which I love talking about this, so fun, but I'm going to cover three really big things. So how to hire, how to train and how to retain. It's one thing to Hire a VA or a team member. It's another thing to train them. But the biggest thing is retaining them and keeping them on your team long term. All of my VAs and team members have been with me for probably over a year. I think there's a couple newer ones obviously as we grow, but most of them have been with me for over a year, some a little longer than that. And that all there's value in retaining your team. You never want to hire someone and have them leave three days later. There's a whole process and I'm going to cover all three of these.
Here we go.
Okay, so there is four major roles in the beginning that I highly think that everyone should outsource. They're the easiest to hire. So first one being is your virtual assistants. I currently have a team of six virtual assistants that run every single aspect of my business on a day to day. I barely am in there for any time. All I do is just be there for support if they need anything. Now these VAs can do whatever you want them to do, whatever you feel you need support in. But mine do everything. So a couple of those things could be your guest communications, they can do your dynamic pricing, they can do your cleaner management, they can even do your direct booking management and any of the day to day operating task within the company. That is the probably biggest role in my company is my team of virtual assistants followed along my cleaning team. Those two are like support each other like this, like glue. So your cleaning teams are responsible for maintaining those five star turnos. You need a cleaning team, you need a good cleaning team and you need to be able to rely on them. The next role is your handyman and your runners. So typically these can also be hired within your cleaning teams at times. So if your cleaner is like a wife and she has a husband, many times I have the husband become the handyman for me and it's just a dream team. So your handyman will be responsible for fixing anything that the maintenance on the property may not be responsible for. And then you also have those runners if you're like hey, because again we're remote. Hey, this happened and I need some support. Can you run to the store and go grab batteries for me or whatever it may be. If you need a runner you have the option to have one or there's also amazing things like doordash or multiple times I've ordered batteries on doordash. We have a lot of tech these days so some of these things are not needed. But it's good to have the option.
I've got some really good questions I just want to throw at you while we're going through this, and I think it's really topical to this. So the first one is, do you have virtual assistants that are around the clock, 24 7? How does that work?
Yes. So I have a team of six.
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