How Jeremy Manages a 7-figure STR Biz Remotely

Quick Summary

Jeremy outlines his strategies for managing a seven-figure short-term rental (STR) business remotely, highlighting the importance of automation, delegation, and strategic oversight. It provides insights into streamlining operations, leveraging technology, and using virtual assistants to handle day-to-day tasks while focusing on high-value activities like pricing and portfolio growth.

Key Points

• Use property management software to automate guest communications and booking processes.
• Employ virtual assistants (VAs) to handle guest messaging, coordinate with cleaners, manage maintenance requests, and order supplies.
• Develop standardized checklists for cleaners and require photo documentation to ensure quality.
• Maintain oversight on critical issues, such as emergencies or complex maintenance, but delegate routine responsibilities.
• Build systems that support scaling without adding stress, such as integrating suppliers and leveraging tools like dynamic pricing software.
• Define personal and business goals to align daily operations with long-term aspirations.
• Use tools like OpenPhone for team communication and guest support to maintain professionalism while staying remote.

Full Transcript

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We are live with the Short-Term Rental Pros podcast from Positano, Italy. Today, I have a very special episode for you guys. It is going to be a solo pod about how to manage short-term rental properties entirely remotely from this handy-dandy device over here in my hand, called the telephone, or to not even need your phone or to be connected at all with the internet—with your guests, with your cleaners, directly.

So, the first thing I want to do is take a step back and reflect on the first rental I ever had. This was several years ago. It was on a lake—my first, you know, first listing at a rural property on a lake in North Carolina.

We were super excited when the guest booked. I literally drove to the lake with the set of keys for that property and handed the keys to the guest. I walked around the house, showed the guests how to do all these different things, kind of gave them the lay of the land, and then left. So, I spent an hour driving, two hours there, and then an hour driving back.

That was several years ago. To think about how far things have come—even my own thoughts—I didn’t think this was possible. This week, the week of September 10th, has been very busy. Today is September 15. We had almost every property booked for almost the entirety of the week. We had about 20 or so, 20-plus, check-ins and checkouts, hundreds of messages, and multiple maintenance requests. And still, I really haven’t had to put much time into it.

I’ve been on a boat multiple days this week. I’ve been on—I don’t know—how many hikes or runs we’ve been on together. I’ve had countless dinners every night, and it’s been really refreshing just to know that while I’m doing all these things, the business is still operating. We’re still, for the most part, getting five-star reviews on every guest stay. The payouts are hitting our bank account.

That’s why short-term rentals in real estate are awesome. You can be across the world, and the business is still operating itself. These assets are able, in many cases, if you do it right, to run themselves and put cash in your pocket with or without you physically being there or being that attentive.

Again, for that first guest, I literally handed them the keys. How did I get to where I am today—having 25 listings, pulling over a million bucks a year, and hosting probably thousands of guests a year? How did we automate that?

I want to say "automate" for the most part. I want to be very clear that I feel as if my business is like 99% automated. But I still like to be in tune with things and make sure the quality stays super high because no one’s going to care as much about the quality and the guest experience as you are, as the owner of the business. So, I still like to check in every day to make sure things are going well. If there are any issues or inefficiencies, how do we deal with them? How do we make things smoother?

For that first guest and first booking, I was super excited. I started growing the portfolio. I kept adding—Arbitrage, co-hosting, purchased properties—adding, adding, and adding. At first, I didn’t have any help. It was really just me. The first thing I did was, obviously, hire cleaners.

The first cleaner I had for my first property was not great. She was not a good cleaner. She wouldn’t do all the little extra things. For example, if there was something she deemed outside her responsibility, she wouldn’t do it. If there was dog poop in the lawn, she wouldn’t pick it up. We kept getting bad cleaning reviews, usually for little things that would have taken her a minute to do but she didn’t do.

What did we do? We got new cleaners. We found ones that seemed to be more passionate and cared more about making the guest experience great and addressing all the little things that needed to be done.

That’s the first thing: your cleaner is the most important. That’s how you automate 75–80% of the business. You just have a good cleaner who, when cleaning, looks around, checks things out, and makes sure that not only is the place clean and the beds are made, but that if there are any issues—let’s say a deck board is rotten or broken—she tells you.

The best cleaners are the ones who have additional abilities, like a handyman partner, maybe a husband-wife team where one can fix things, or they have a colleague or friend who can handle little repairs. At the bare minimum, they need to tell you when there’s a problem with the place.

So, that’s the first thing: a cleaner who not only cleans but tells you what’s wrong.

The best ones are the ones who can take care of the things that are wrong. But nevertheless, at bare minimum, at least tell you. So, that's the first step—got better cleaners and then realized the importance of having good cleaners.

So now, at this point, I'm in probably about—I think I have like six different sets of cleaners.

Not only that, you know, I got rid of that first one and got a new one, but I have six sets of cleaners across different locations. I've probably been through about 14 or so cleaners. So, it's really important that you find a good cleaner who cares and is someone you can say, "Hey, look, I want to scale my business here. I want to have more properties, and I want you to be my partner. But in order for that to happen, you need to help me—help me help you."

So, cleaners having that synergistic relationship is super key. What you can definitely do with the cleaners is provide a checklist—everything they need to do, everything they need to look at, send you pictures, and give them a list of everything they need to take a picture of after each clean. This way, you can use your own eyes to tell that the place is good. Also, if a guest complains, you have pictures to reference.

That's what I did first—made sure I had good cleaners as I was scaling the portfolio. Once, but at this time—I'm going to go back—this is still 2020–2021, I was still doing all the guest communication myself.

I was sending every message to every guest. I didn't even, at that time—I don't even think I had property management software. So, I literally had notes where I would copy and paste, like, you know, the messages—the common FAQ messages I had. I would literally, you know, be there responding on my phone. I was always on edge. I was always glued to my phone because I wanted to give that under-one-hour response time that Airbnb has as a super key metric.

I was doing all that myself, probably up to—I would say—I was probably up to like five, six properties when I then enlisted a property management system (PMS), a software that could help with the messaging.

So, if someone reached out, I would automatically send them a message back saying, "Hey, thanks for reaching out. Please share some more information about your group. What are your ages? How many of you? What brings you to the area?" Then, you know, check-out messages, trash messages, and things like, "Hey, just checking in to make sure everything's okay. Is there anything we can be helpful with?" It just automates kind of the cadence of messages. That, I think, took at that point maybe, I'd say, about half the messaging burden off myself. But by no means can a property management system take away 100% of that messaging burden.

So, five properties—myself and the PMS. Then I got to probably about 10 properties towards the middle of 2021. That is when I hired my first virtual assistant.

What is a virtual assistant? Well, just like you and me, a virtual assistant is a human being. Oftentimes, what makes them virtual is, you know, they're probably in another country, and you're probably going to interact with them over your phone. Maybe you'll go visit them one day. Maybe they'll visit you. But that's what a virtual assistant is. Oftentimes, they're in countries like the Philippines, Pakistan, or India.

The first virtual assistants I hired were from the Philippines. Previously, in, like, previous jobs, I had worked with Indian developers. So, to me, the concept of working with someone abroad was not a new concept. You know, that was something I had been doing in previous jobs. But this was the first time I'd done it for an Airbnb or short-term rental management responsibility.

So, virtual assistant—got them, and at that time, I didn't really know how to train them. This is something I've learned and refined—the processes to really optimize them.

The first virtual assistant I had—it was really her job. I added them as a co-host on every property and really just wanted them to respond to frequently asked questions, you know, things, add a little human touch. I see people over-automate with property management systems where, you know, you can make it so if someone says a certain word in their question, it automatically responds.

Someone says "airport," you know, it'll tell them how far away the airport is automatically. But really, you don't get that human touch. Also, oftentimes, you kind of respond wrong when you try to over-automate with the PMS. So, you need a human to actually, you know, show empathy, show that you're actually listening to what they're saying.

The first VA was purely just messaging. The second step was getting them to coordinate with our cleaners. So, you know, we have our cleaners integrated with our property management system, meaning, you know, they're plugged in. They, you know, can see the calendar, they can see the schedule. But sometimes, there are last-minute bookings. You know, oftentimes, today's Saturday. We might have a property open today, and it gets booked at 2 PM. Check-in is at 4 PM, and, you know, cleaners aren't necessarily going to check the schedule that often. They might be cleaning somewhere.

So, what you need is a VA who can just call the cleaners, ping them, send them a message. That was really the first step. First was messaging; second was connecting with the cleaners so they could communicate with each other.

The third step is getting them to communicate with your maintenance vendors and do supply ordering. So, you know, things break. For instance, yesterday, a guest had pulled down one of the curtains in one of the bedrooms of one of the houses, and we needed that curtain back up. You don't want a guest arriving and seeing a curtain fallen on the ground.

Our cleaners probably don't have the tools, like drills needed to drill back in drywall anchors and put up curtains. So, we needed to get one of our handyman vendors out there. We have our virtual assistants. Got them a phone number with OpenPhone so they can call our handyman, call our maintenance vendors, and just say, "Hey, we need you over there. This is what you need to do. Here's a picture of it from our cleaners. Can you do it?" If they can't, we ask, "Who's our backup handyman? Who's our backup maintenance vendor?"

That's just an example from yesterday. But what you need—that's what I call maintenance requests. You need your virtual team to be able to handle maintenance requests. When things go wrong, you need a process in place to make sure things go right. So, you need close communication with your cleaners, with your virtual team, and with your maintenance vendors.

If you've done all that—I know, I think we've only been talking for 13 minutes, 45 seconds here—that's really going to automate about 90% of your business. However, you know, that extra 10%, that's things like bookkeeping. You know, your virtual assistants—a lot of times, you can get one who might have a background in accounting or bookkeeping, and they can do guest communication and bookkeeping.

One of the things I actually touched on earlier that I'm going in on is ordering supplies. You can have your virtual assistants—let's say the cleaner says, "Hey, we're out of dish soap and toilet paper." For me, I have one of my virtual assistants plugged into my Amazon business account.

They order supplies directly to the cleaner's house so they can bring them during their next clean. We usually have backups of supplies in the owner's closets. And that's a key here: always have supplies—backup supplies. Always have an owner's closet, or if you're doing apartments, have a storage space or something where your cleaners, on short notice, can go in and get the extras.

Then, you want to be able to have your virtual assistants order supplies either to the house or to the cleaners. That's what we have. Also, at one of my bigger locations, my cleaners literally have a credit card. I gave them one because it's harder to get supplies quickly in some areas. Amazon and Walmart do deliver, but it takes four or five days, whereas in most places, Amazon Prime might take one day for the essentials. So, my cleaners have a credit card. At the end of the month, they tell me what they spent it on and send me pictures of the receipts.

Supply ordering is something that you don't need to do—that your virtual team can do. I used to have automatic orders set up where every month, the same supplies would be sent to the property. What I have found, though, is that oftentimes we would get too much supply, and our owner's closet would just get completely overfilled. You spend more money that way versus complete lean efficiency—ordering as needed, ordering as needed to the properties.

So, supply ordering—that's taken care of. Guest communication—that's taken care of. Even so, relatively recently, guests have been calling me because I personally felt that—you know, again, for me, I do have 25 listings now.

But I like to have extremely high quality. And again, I always felt that if I gave too much of the realms up—like gave too much responsibility in that guest communication—that my reviews would go down. You know, I’d go from 4.88 to 4.6. But I’ve actually gone up in the last year. I think I’m like 4.92 or something since I’ve really kind of handed the keys over.

And one of those aspects is the phone number. So, we have a message that gets sent to every guest: If you have any issues that can’t be resolved via message in this chat, call this number. And that number is not my phone number; that is an OpenPhone number for my team. So, phone calls—you know, that’s something that your virtual team can do too.

So again, I think that right there, what I’ve just told you, constitutes—we’ve got bookkeeping, we’ve got ordering supplies, dealing with cleaning, dealing with maintenance. We’ve got, you know, calendars.

Really, the things left are, I would say, pricing. I still do the pricing. To me, that’s like the most important thing I can spend an hour a week doing—pricing. And I’m going to be better than anybody else at it. A lot of it is like, you know, pricing is not a perfect science.

You have different properties and different—like a lot of people do PriceLabs, set it, forget it, you know? They use a dynamic pricing software. To me, I use dynamic pricing software such as PriceLabs, but I also go in, and I set a lot of customizations. And, you know, sometimes the customizations I set might not be working as I like, so then I change it. I test them.

To me, pricing is an art and a science, and because of that, I can’t really explain to someone how to do it. If you can’t explain how to do something, then a virtual assistant won’t be able to do it as well as you. I’m constantly changing my pricing, testing, doing new things.

And that’s something I like to be at the forefront of, and one of the reasons why, you know, our properties, I think, are always, you know, 90th-percentile earners, is because I’m so on it for all of our properties in terms of pricing.

And that’s also one of the things you can automate. At the bare minimum, use a dynamic pricing software. Most markets, you’re going to have enough data where they’re going to be good. In some rural markets, they’re not. They’re just going to suck because there’s just not a lot of data for the pricing software to use.

But using the pricing software, again, that by itself, you know, gets you to that 80th percentile of pricing automation. And then that last 20% is manual configurations. You know, you see, Hey, my next three weeks are open. Why is that? Look at the competitors. Oh crap, they’re pricing a lot lower than we are. We’ve got to drop below them.

That’s kind of what I call the manual touches. So now, we’ve got pricing, we’ve got guest communication, we’ve got maintenance issues, we’ve got bookkeeping, we’ve got ordering supplies. That right there, I said, gets you to about 95% of Airbnb automation.

So, what is that last 5%? Well, I would say it’s growing your portfolio. You know, if you want to keep your portfolio the same, yeah, you can probably automate most things. But if you’re like me, you want to grow.

So, what are things that you should be doing? Well, one—coming up with a strategy for your next investment. What is it going to be? If you’re doing arbitrage, you know, reach-outs. You can have your virtual assistants do reach-outs. You definitely can, and you definitely should.

I have mine—one of my VAs—what they’ll do is they’ll literally send messages to every property in different markets that match our high-level criteria. They’ll just send a message, and they’ll start sending emails back and forth.

However, the sales calls or the phone calls—whether it be a co-host, you know, owner, whether it be a building—the actual calls and the sales and the pitching of yourself, that is something I like to do.

I think that is one of the highest and best uses of my time. Thus, it is something I do. Analyzing new properties to buy—we have our VAs scraping, you know, a bunch of different listings, trying to find unique properties in different places. And when they find them, they send them to us. But as for, you know, the intangibles—the floor plan, the kind of the look and the feel—that is something I think is a high use of my own time.

So, if we have a property under contract, I’m gonna go look at it. I’m gonna go check it out. Obviously, someone across the ocean in the Philippines—granted, technically, I’m across the ocean right now—it’s going to be hard for them to fly over to look at a property.

So, there are things that you should be doing, but you need to be thinking about what is the highest and best use of your time. Again, if your goal is to, you know, grow the business to a certain place and then F off—you know, be in Positano, Italy. We’re going to Paris, France, next. Or where are we going? Sunday—Sunday to Paris. Then I’m going to be speaking at a conference in San Diego.

Sure, you know, you can get it where maybe all you have to do is just check in and make sure things are good, and then deal with emergencies. What might emergencies be? Emergencies—you know they do happen. You have 25 listings. Random things are going to happen, and they are things that you should definitely be available for.

For example, I had one of my furniture assemblers drop off all the cardboard with my address on it at a grocery store in their trash banister. The grocery store called the cops because there was a ton of cardboard, and they just took a U-Haul over and dropped it.

Cops showed up at the door. You know, my VAs noticed on the Ring camera that a cop showed up. I got in touch with the police and just made sure, "Hey guys, just want to make sure everything’s okay." By that time, I didn’t even know that the trash had been dropped off at the grocery store. I just saw the police that showed up.

So, I dealt with it. You know, I called in. I was like, "Hey, I just want to make sure everything’s okay." They told me the situation, and we got it dealt with.

That’s just a recent example of a quote-unquote emergency. But, you know, emergencies could happen all the time. You know, if you have a—say you have a really high-end water heater that’s broken, and you’ve got to find, you know, someone who has a very specific part for that water heater. You might have to call, learn about the water heaters, learn about, you know, who the suppliers are, make a couple of phone calls, and get things taken care of.

You can’t have local crews that are able to do that. I do, a lot of times, have folks who deal with, you know, even the more complicated maintenance requests. But sometimes, like our air conditioning in Florida, just is having super complicated issues. It’s not just like, "Oh, we send an AC guy there, and he fixes it." It’s, "Hey, it needs some part to regulate some other part."

Actually, my business partner in this case took that lead. But there are instances where it’s just kind of complicated, and you’ve got to use some brainpower to figure it out. Right now, actually, in Florida, we’re dealing with kind of like a permitting, paver, Tiki hut situation. And, you know, I’m drawing up the specs of what we want done.

But that’s something I also like to do. I like to do landscape design. I like to renovate houses. So, that’s something to be thoughtful of—what is the highest and best use of your time, and how do you optimize for doing that? If the highest and best use of your time is being on the beach in Italy, all right, get your business to the point you want it to be. Get it so, you know, maybe just check your phone once a day, make sure things are okay, and then enjoy yourself.

And that’s totally cool. But if you’re like me—you know, you want to grow. You know, I’m not trying to add a thousand properties tomorrow, but I want to grow over time and just keep moving in the direction that I want to go.

You’ve got to figure out what you like doing and how you, you know, automate the things that: A) you don’t like doing, and B) aren’t actually helping you grow your business. I like talking to investors. I think it’s a good use of my time. I like analyzing properties. I like working with my mentees and helping them—helping them, you know, do the same things, helping them automate their businesses, helping them figure out what’s a winner investment, helping them use our resources to design the properties.

Speaking of design—that’s something that’s super important, and you can automate as well. There are various degrees of automating design. There’s using design toolkits.

For example, we have design toolkits that we’ve made over the past, and our mentees use them. Or, you know, it could be having a designer. We have designers we work with who will do it for you. They’ll figure out what to order, and then you can just have a furniture assembler.

You know, you have your designers designing and ordering the furniture, you have your furniture assembler putting together the furniture. Bang! You’ve just pretty much, you know, 95% of home setup has just been automated.

So, I think—I hope—you guys found that valuable. Before I leave you guys today, I want to just recap. We just went from where I started—so first property, first rental ever, literally handing over the keys. The guy’s name was Aussie Dave. He was a professional motorcycle driver, which is pretty cool. Great guy.

I’m not gonna lie—it made me, like, you know, I think a lot of people are like, "Who’s gonna stay in my properties? I’m scared they’re going to be terrible people, and they’re gonna trash my property." For me, having this really cool professional motorcycle driver be my first guest, he actually had his sponsor fly him on his private jet to the area. Just seeing that, I was like, "Damn, I actually might be interfacing with some pretty cool people by doing this line of work." And I totally have.

I’ve hosted executives at Fortune 500 companies. I’ve just hosted cool people, nice people. You know, some people who see an issue and fix it themselves. They say, "Hey, heads up, there was an issue here, but I’m just gonna let you know. I had tools," or, "Hey, do you have a screwdriver? I’m gonna fix this." Like, you deal with good people, which is really beautiful to see.

But again, I went from that first guest—spending, not even the messaging, just the actual driving and handoff aspect, handing keys aspect—four or five hours to having 20-plus rentals this week. Probably a $40,000 revenue week. Again, this was a good week because there were some compression events, meaning some high-demand things in our markets. The reason they’re high demand is because there might be a music festival, which we had one of those this week.

So, probably about a $50,000 revenue week with pretty good margins. So, you know, my take-home—probably about 40%-ish margins this week—which paid for this super expensive vacation, fortunately.

Busy week, but I’ve been here. I’ve been present. I’ve been going out on the boat, running every day, hiking, going to meals, enjoying myself. And, you know, just checking in on my phone and computer.

Something that I like to do—again, guys, it’s like, I think it’s about finding out what you like to do, what’s important. Like, don’t just automate your business so you can, like, sleep all day. You know, that’s not the point of it. You want to automate your business so you can do things that are going to lead to personal growth.

Our software company, BNBCalc—we have some really exciting things coming up. I’ve been talking to our Asian business partners, who are in Asia. I’ve actually been closer in time zone to them, which has been helpful. So, communication’s been easier. But we have some really exciting new product launches or features that are about to come out. We’re about to have more data providers that we work with to help our users have more value, have a more valuable tool.

That’s something I like doing. You know, that’s a tool that I’ve enjoyed building, and it’s awesome seeing people use it. And, you know, also, I’ve been texting. You know, I’m lying on the beach, but a mentee reaches out and has something exciting to talk about. Like, you know, we’ll chat.

So, it’s about doing what you like to do with your time. And that’s—before you do any of this—that’s an exercise you should do for yourself. If you currently have an Airbnb business, and you know, you might feel that it’s a stressor on you, there are ways to negate that. Build out your systems and operations. Get them in a place you need them to be, and then that’ll free you up to do what you actually want to do.

So, I feel like I was at a point where my Airbnbs were bogging me down—probably 2021, when I had about 10. I was like, "I can’t just keep growing if this is what the result is going to be—more stress." But now, I’m at a point where it’s like, I just want to grow and get new, awesome properties because I don’t feel that same weight on my shoulders or that same stress. Adding new properties isn’t gonna, like, make my life worse.

So, I hope that was helpful. We walked through going from nil to, you know, a seven-figure year, 25-listing portfolio, 97% automated Airbnb business. If you guys have any questions or if there are any specific topics you want me to dive into deeper, I’m always happy to do so. And again, I always appreciate you guys tuning in.

This is the Short-Term Rental Pro podcast. Stay tuned for next time.