50 000 Guests Later: My 10-Year STR Journey & What's Next

Well, welcome to Short-Term Rental Riches. Today is an extra special episode because it's number 300. Almost six years have passed since I first started putting out content each and every week, starting on the podcast, but now, of course, on YouTube as well. And my journey as an STR operator and owner and investor has really changed over the last decade since I first started with that small forplex and now owning properties in multiple countries and multiple cities and managing those alongside hundreds of other properties with our

amazing virtual team that is spread out all over the world. Today I'm going to be sharing how this journey unfolded, how we get excellent results no matter where we are, and also break down the pros and the cons in the industry, and my most influential resources. Whether you're just starting with your first short-term rental or you're growing your portfolio, the lessons in today's episode are going to help you along your journey. So, here we go. Let's jump into 10 years of short-term rental history in one

jam-packed show. I'm going to rewind just a little bit for those of you new to the show. The whole reason I got into short-term rentals is because they were making more money than my long-term rentals. But of course, this was over a decade ago, so a lot of things have changed. I got into real estate really in the first place after reading that purple book, Rich Dad Poor Dad by Robert Kiyosaki. I'm sure like many of you. And over the years, I've had the pleasure of

meeting with him multiple times, having dinner with him. He's been a huge influence on me, but it hasn't stopped there. I think the reason that we've made it to 50,000 guests and then we're going to make it to 100,000 very soon, and pretty soon we're going to be at a million guests. We're just going to keep growing because we've fallen in love with the problem. And this idea comes from a book written by the founder of Ways. In the book, he encourages entrepreneurs to relentlessly look

at the actual problem and not the solutions. Right? We know in this industry we have a lot of software solutions. We have a lot of management options, but to actually fall in love with the problem and understand it is what's going to create true success. And so our team has the benefit of owning our own properties alongside the hundreds of properties we manage. So, we're in this day in and day out improving our operation. And I know one thing for sure after 10 years in the

industry with short-term rentals is that the better you operate your properties, the more money they're going to earn and the better your guest experience is going to be. That, of course, is easier said than done. It requires a lot of experience. Of course, we're not going to achieve what we want if we're not taking steps each and every day. And so this leads me to really the biggest influence I've had in my life. It came from a book called The Slide Edge by Jeff Olsen. And

I'm not going to break the whole thing down here. I just want to break down the main point is that we're either getting closer to our goal or we're taking steps away from it. Everything we do is either moving us closer or further away. like we know the things that we need to do, but they're also easy not to do. And because they often take a long time, we don't see the results and we stop. So, I'm going to give you my top seven books in

the order I would read them that I think is really the blueprint for achieving whatever you want. Whether it's short-term rentals or whether it's something else, I promise you, these are gamechanging books. When I started over a decade ago with that forplex, there was just a little over 1 million Airbnbs in the whole world. And today, fast forward, there's over 8 million. So, eight times more. So, that's one of the biggest changes, right? Just in the number of sheer short-term rentals available and in the way

that we use them. But when it comes to operations, well, we know that that has gotten much more challenging as well. So, going way back, my first short-term rental was easy. I literally put it online and people were booking it. It was staying occupied and I was earning way more money than I was as a long-term rental. The reality today though is that it's much more challenging to find a cash flowing investment because prices are higher and interest rates are higher and the amount of rent

that we can get hasn't gone up that much. And if we're in a market that's overs supplied, well, then it's actually gone down, right? all these new units driven up the amount of supply and if the demand hasn't kept up, which it hasn't in a lot of these places, then it's much harder to make money with short-term rentals today than it ever has been. Management has gotten much harder just because there's much more units and demand has not kept up. And this has also led to

much higher guest expectations. So, these are some of the cons of what's happened over the last 10 years, right? And some of these might be obvious to you, but I just want to reiterate how important your operations and your management is because we see all the time there's lots of data. You can have two properties very similar to each other in the same market, same neighborhood, same amenities, and one can earn quite a bit more than the other property. Now, one other challenge that might not

be so obvious to most of you is that when it comes to our revenue management, they don't show the whole picture. And so, what do I mean by this? They don't bring in your reviews, for example. They don't show you the difference between multiple channels, which today you absolutely have to be on all the channels if you really want to outperform. They don't show you how many people are actually visiting your property online, how many people are seeing it, how many views you're getting, how many

people are clicking on it. And all of that information is incredibly important. So, I would say today, this is one of the biggest challenges because markets have gotten so much more competitive. Dynamic pricing is really a given now, right? You could be using Price Labs or AirDNA or Wheelhouse or any of the pricing tools. That's pretty easy to turn on, but then you got to know how to use it, and they're getting more and more complex. And then you have to account for all this data

that's not actually in those pricing tools. So, yes, today the industry is much harder than it was 10 years ago, but there's still lots of opportunity. We see it each and every week. And if you're managing your properties really, really well, then you can outperform your competition. All right, let's talk about the positives now. So, AI is all the buzz these days, and it's made its way into the short-term rental industry, and it's not going anywhere. It's going to pick up steam. It's going to provide

more and more tools for us to make the operation easier, to make the guest experience easier. So, I'm really excited about that one. I'm also excited to see that the supply is tapered off in a lot of markets and that people are still going to continue to use short-term rentals. But I did an episode recently where I talked about how supply in one of the markets where I am in Tennessee has actually come back down and so my revenues going back up. So, a lot of

changes over the last 10 years. Definitely some pros, definitely some cons. And there's been a lot of changes in my personal portfolio. So, I want to break down this part of the journey real quickly. When I first started partnering with other owners really across the world, a lot of listeners that had reached out from this show and asking, "Hey, Tim, can you help me manage my properties?" That wasn't the intention for a long, long time, but a few years ago, I decided to start doing that.

And I started a company called Midtown Stays. It was modeled after the fact that most of my personal properties were in Midtown areas. But of course, we branched out. But we started managing properties all over the world from coasts and lakes to mountain retreats and ski resorts, all types of properties. And so that Midtown stays name didn't really fit any longer. And a good friend of mine came along during this journey, someone I had known for years and that also had a lot of success in

the real estate world. He built a hotel. He had multiple properties in multiple countries operating them as short-term rentals. And he said, "Hey, Tim, have you ever thought about partnering with someone?" And I had thought about it, but I didn't think I was quite there yet or I didn't think I would find that person so soon. And so, long story short, we partnered up and it's been an amazing journey since. If you go back to episode 278, we talk about how Justin and I both believe

that virtual management is the future of all property management. And we both share the same passion and we've been growing the company since, improving every little thing. Again, focusing on the problem. Justin has been instrumental in helping us grow to where we are today, but so has the rest of our team. We have an expert team, a lot of people with a lot of different backgrounds and expert skills. It's really divided into three individual teams on the back end. So we have our guest experience team

which helps us with all things related to guest experience and not just communication which is what a lot of us think about uh when we think about reception but there's all kinds of pieces in that guest experience right we have to make sure that all their questions get asked in a really timely manner we need to manage the reviews we need to manage housekeeping we need to manage support with Airbnb or Booking.com or whoever it happens to be and then we have an awesome listing specialist

team which helps us get all of our listings online, keep them optimized, keep them updated, and manages that whole process really to make sure that our listings stand out and we maximize all those views, which of course turn into reservations, but they wouldn't turn into reservations if they're not priced properly. And so that's our third team, which is our revenue management team. And they do an amazing job using all the available tools that we have in the industry today, but also some of our own internal

tools. And we're looking at every single piece of the puzzle there. We're looking at not just our market data or properties that are competitive to the subject property, but we're looking at how that property performed last year or how the market performed last year, how it's performing the next 7, 30, 60, 90 days further out into the future. We're looking at booking windows. We're looking at minimum night stay setup. We're looking at all these sorts of discounts. I mean, there's really a lot that goes into

it. And we do that on a regular basis. Of course, as I mentioned before, these tools don't show the whole picture. They're really missing some pieces. And so, we built our own tools on the back end to help us view all the other important pieces that don't go into dynamic pricing. And to help us do that, we also have a couple developers on our team. And we're using all the best technology out there. We don't want to reinvent the wheel, but the reality is there is

no single perfect program out there to help you with the whole operation. So, we use the best of what's out there and then we use our developers to piece together the backend for the things that are currently missing. So, we have an amazing amazing team and that's how we can get excellent results and how we can keep growing and how we have word of mouth and all of these things that are necessary to grow a good business. It's been an awesome awesome journey and I'm really

excited to continue bringing on properties. I love talking with owners really across the world and understanding their unique situation. We fell in love with the problem because this is the same problem that we have. So, our whole team is excited, but I don't think we ever would have gotten here if it weren't for some incredibly influential authors and books that I've read along the way. So, I want to share my top seven books just with a real quick one-s sentence explanation so you can get an

idea of what it is. And I promise you, if you read these books, they will change your life. And if you already know what you're passionate about, maybe it's short-term rentals. Well, it's going to help you along your journey. No doubt about it. Some of these books I've talked about in prior episodes. So, if you're new to the show, you can go back to strries.com. You can see all of our prior episodes. We've talked about every little piece of the short-term rental operation. We've had amazing

interviews with some of the the tech leaders and and our website's packed full of helpful ebooks and all kinds of things. So check out strriches.com if you haven't already. If you've been enjoying the show and the content, I'd really appreciate a thumbs up or a like. It's going to help us spread the word, help us reach more owners around the world to help them have less headaches and earn more money with their short-term rentals. Okay, so here we go. And I'm just going to read off

my list here. Uh, and these are in order of how I would recommend reading them. The first one I've talked about before. It's The Happiness Advantage by Shaun Akor. And the whole idea of the book is exploring how a positive mindset fuels success in performance and life and in your skills. And so starting with a positive mindset really provides more success. And one of the big takeaways from the book is that happiness is learned. It's not something like we're born unhappy and we just stay that

way. But we can actually improve it. It is a habit. I've got another book here on habits. So number two is mindset. And this is by Carol Dwek. The whole idea of the book, it introduces the idea of a fixed verse growth mindset and how adopting a growth mindset can transform your potential. So your intelligence is not fixed. Your success at whatever you're doing is not fixed. If you took the SATs years ago or if your IQ score is lower, that doesn't mean that it has

to stay there, right? These tests were really actually the IQ test was developed to determine how well subjects in school were working with the students. It wasn't determined to come up and and identify how intelligent a person was. They sort of just stuck with it which is pretty sad because a lot of times someone might label someone else and they sort of stuck with that label. But this book is a mindset changer. Basically says we can get better at whatever we want. We can grow at

whatever we want. not just in the business world but also in our relationship. Okay, the third book, Slide Edge by Jeff Olsson. I already talked about this one, but just to recap that real quick, it emphasizes how small daily decisions compound over time to produce either successes or failures. Number four is Atomic Habits by James Clear. So, even though we know we need to do these little steps, they're not easy to do. And so, Atomic Habits makes those steps easier. It makes your habits easier to

do. And here's the one sentence takeaway. It offers a practical guide to making small, easy changes that lead to remarkable results by making habits obvious, attractive, easy, and satisfying. That is key. Number five, I've talked about this one before as well, but this is a classic. You've undoubtedly heard about it before. It's Napoleon Hills Think and Grow Rich. It's over a hundred years old, and the information in that book is as important today as it ever has been. The one sentence takeaway are is that it's

it's about principles for achieving personal and financial success through focus, desire, faith, and persistence. Napoleon Hill studied dozens of highly successful people, and there's clear patterns to how they became successful. So, Napoleon Hill's book is really, really helpful, but it does assume that you know what you're passionate about. You know what your desires are. And so, I'm going to assume that you know what those are as well. and to continue down this journey to help you get to where you may want to be if you're

not there yet is having a team. And so I talked about our team already, but one of the books that helped me grow our team faster is called Who Not How. It's by Dan Sullivan and Benjamin Hardy. And I'm going to read the one-s sentence takeaway here. Basically shifts your thinking from how do I do this to who can help me achieve this for greater impact and efficiency. And another big takeaway from the book is that you probably find yourself procrastinating with quite a few areas

of your business, of your short-term rental operation, whatever it happens to be. Those are very likely the things that you least like doing, but that doesn't mean there's not someone else out there that enjoys doing those and also does them better than you do. And so, if you don't enjoy any part of your short-term rental operation, well, of course, we would love to help you with that. Shameless plug there. Number seven, this is the last book. This is the E-Myth and this is by Michael Gerber.

The one sentence takeaway explains why most small businesses fail and how to build a business that works without depending solely on you. So all of these things are connected. This book is a true classic. Uh and this is assuming that you want to build a business, right? You found something you're passionate about. You set up the habits to get you there. You realize that those habits really do turn into really big results, but they don't show up overnight. you found some people on your team. Well,

finding people is just the first piece. Then you have to train them, right? And that's what we find a lot of times with the property managers that we're working with is that that training process requires a lot of experience really and a lot of time and a lot of standard operating procedures, but the E-Myth will help you discover those standard operating procedures and really put them into place and develop a platform. So, there you go. my top seven recommendations for books that truly changed my life

and also in order of how I would read them. Now, again, I know most of you aren't probably going to go out there and and grab these books. If you want me to do a full episode breaking these books down further, I would love to do that because as I teach about what I'm learning, it helps me learn it even better. That's another reason why I've loved doing this show over the last six years. So, leave a comment down below. Shoot me an email from strriches.com.

Let me know. I'd love to do an episode just on those books. But coming up, what I'm excited about for the future. If you've tuned in for a while, well, you know that I'm building a boutique resort hotel here in Medigene, Colombia, where I currently am. 20 units on the side of a mountain with an amazing view. There's really nothing like it here in this city. I think it's going to be amazing project. It's almost been 3 years now, but we've seen some really good progress.

So, I've got a future episode coming up. I promise. I know I keep talking about this, but I will show you some footage of that project, some of the first units, the designs, uh, and also a breakdown of of how I expect that property to do. So, lastly, just a couple thoughts of how I see the future going. Well, I can tell you what, I'm passionate about short-term rentals and operations and efficiencies and providing better guest experiences and maximizing the revenue for our partners. I have

fallen in love with the problem and I do not see that changing. And so the next steps for me and for our team is to continue growing. We really do want to be the most respected and largest virtual property manager in the world. And so I'm excited for the next 6 years of episodes. I'm going to be back here each and every week. One of the benefits to you is that as we take on thousands and thousands more reservations, our learning curve is much much faster

than yours is if you have a smaller portfolio. And that's one of the things that just kind of dawned on me a little bit more recently is if Airbnb makes a change or if there's some sort of new tool or something that comes along, well then we can test it quicker than we could 5 or 10 years ago when our portfolio was much smaller. There's a fabulous quote by Les Brown that says to achieve something that you've never achieved before, you have to become someone that

you've never been before. So those seven books that I mentioned will help you become someone that you are not currently today. I promise they are lifech changers. I hope you found these last six years of episodes really helpful. This was an exciting episode for me. It's been a long journey. We've learned a lot. Until next time, I hope you have a fabulous week.