Well, welcome back to the Short-Term Rental Riches Podcast. I’m Tim Hubbard and today is a special day episode. 300. I can hardly believe it. A lot has happened since I hit record on episode one almost six years ago. And more than a decade ago, when I started my first short-term rental, I was living across the hall from my very first guess in my very first short-term rental property, which was a small fourplex.

And fast forward today, I’m proud to own properties in three countries and multiple cities. And really proud to have an amazing team of experts around the world helping me manage my properties, not from across the hall, but from across the world virtually, and to be doing it alongside hundreds of other short-term rentals and all with excellent results.

Today as a special milestone episode, I’m sharing how this journey unfolded. We’ll jump into the pros and the cons in the industry [00:01:00] and my most recommended resources. Whether you’re just starting out or you’ve been in the STR industry for years, this episode is packed with the lessons and resources that have made the biggest impact.

On me, the small habits that compounded into massive results, the books that literally rewired my thinking and the questions I’m asking myself as we head into the next chapter. So here we go. Let’s dive into 10 years of short-term rental lessons and one jam packed episode.

So here we go. The journey to 50,000 guests. I’m gonna 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 lo 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 [00:02:00] 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 that we’re gonna make it to a hundred thousand very soon, and pretty soon we’re gonna be at a million guests, we’re just gonna keep growing because we’ve.

Fallen in love with the problem,

and this idea comes from a book written by the founder of Waze, 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 [00:03:00] 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, and it requires a lot of experience. it has been a long journey so far to 50,000 guests,

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 Olson,

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, 1, 3, 5, 10 years. We don’t see the results and we stop So I’m going to give you my top seven books and the order I would read them that [00:04:00] I think is really the blueprint for achieving whatever you want, whether it’s short-term rentals or whether it’s something else.

And I understand that most of you probably will not want to read these books. That is just the reality. And so you can YouTube them, you can find a 30 minute summary, or you can go on chat GBT, and you can say, Hey, breakdown Tim’s. Top seven books that he swears will change my life in five sentences or less per book.

However you want to do it, I promise you these are game changing books.

Before we do that though, let’s get into the timeline really over the last 10 years and talk about the short term rental industry. When I started over a decade ago with that fourplex, 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.

And of course, this is just Airbnb. We know that booking.com has added millions of short-term rentals. Google Vacation Rentals now [00:05:00] has millions of short-term rentals. 

And so the world has changed and the way that we live has changed. I’m recording this from an Airbnb. Even though I own multiple properties all over the place, I still travel and stay and sometimes live for extended periods of time in short term rentals. I know that my partner does as well, and I know that millions of other people in the world do, and this is new, right?

Remote work has changed the way that we live.

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 ’em. But when it comes to operations, well, we know that that has gotten much more challenging as well.

The reality today though, is that it’s much more challenging. 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 oversupplied, well then it’s actually gone down, right?

All these new units [00:06:00] have 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 wanna 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 neighborhoods, 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. We’re not really seeing the whole picture with our dynamic pricing tools. And now because the industry’s gotten harder, we have to put a lot more focus on revenue [00:07:00] management. But our revenue management tools, they don’t show the whole picture.

And so what do I mean by this? Well, they help you identify what your market’s charging, what market occupancies are, what average daily rates are. Again, these are all average numbers, right? So you need to to dig into the details, but they don’t tell the whole picture. 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’s really a given now, right? You could be using Price Labs or uh, air DNA or Wheelhouse, or any of the pricing tools. That’s pretty easy to turn on. But then you gotta [00:08:00] 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 gonna continue to use short-term rentals. So 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 [00:09:00] 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 wanna 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 have 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. 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 [00:10:00] 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 2 78, 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, 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, not just [00:11:00] 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. So we have an amazing guest experience team that helps us do all that. 

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 [00:12:00] 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 performed in the next.

7 30, 60, 90 days further out into the future. We’re looking at booking windows. We’re looking at minimum nights stay set up. 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 wanna 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.

[00:13:00] 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. Again, we’re, 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’ve gotten here if it weren’t for some incredibly influential authors and books that I’ve read along the way. And so I wanna share my top seven books just with a real quick one 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, if you’re tuning into this show, well, it’s gonna help you along your journey. [00:14:00] 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 st riches.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.

Our website’s packed full of helpful eBooks and all kinds of things, so check out st riches.com if you haven’t already. And if you haven’t, if you’ve been enjoying the show and the content, I’d really appreciate a thumbs up or a like, it’s gonna help us spread the word, help us reach more owners around the world to help them have less headaches and to earn more money with their short-term rentals.

Okay, so here we go. And I’m just gonna read off my list here. But the first one, 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 Sean aor. And the whole idea of the book is exploring how I positive mindset, fuel success in performance.

And life and in your [00:15:00] 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. And I’ve got another book here on habits. So number two is mindset, and this is by Carol Dweck. The whole idea of the book, it introduces the idea of a fixed versus 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 [00:16:00] someone might label someone else and they sort of stick 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 relationships.

Okay. The third book, slight Edge by Jeff Olson. 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 [00:17:00] 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 just 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 Hills studied dozens of highly successful people and there’s clear patterns to how they became successful. Number six. So again, these are in order.

So Napoleon Hills’ book is really, really helpful, but it does assume that you know what your. Passionate about, you know, what your desires are, and so I’m gonna 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 [00:18:00] and Benjamin Hardy. And I’m gonna read the one sentence takeaway here. It 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 on my top seven. And again, this is in order. 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 [00:19:00] 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, 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 gonna 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, [00:20:00] 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 s stl riches.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, future plans.

If you’ve tuned in for a while, will you know that I’m building a boutique resort hotel here in Meine Columbia, where I currently am 20 units on the side of a mountain with an amazing view of the city. There’s really nothing like it here in this city. I think it’s gonna be amazing project, but it also takes a lot of time.

So I’ve been talking about this for a while. It’s almost been three 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 [00:21:00] 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 six years of episodes. I’m gonna 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 five or 10 years [00:22:00] 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 life 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.