Jeremy Werden is a 26 year old with a 7-figure short-term rental business and software startup. Sub to learn the biz! He likes creating businesses that provide memorable experiences for others like vacation rental Airbnbs and boat rentals and those that help empower the next generation of investors such as bnbcalc.com. He have learned soo much in the last several years while building my 7-figure STR portfolio.
Episode Highlights Here:
Jeremy
With long term rentals, it’s really, really challenging, especially in today’s climate with home prices, where they are with interest rates where they are, it’s just very difficult to really cashflow where short term rentals if you do it right, and I want to caveat it with like, you gotta do it right, there’s definitely a right way of doing things and a wrong way of doing things.
Brett
Think what is the number one secret to the key to freedom with short term rentals?
Jeremy
Yeah, so the thing that’s really unique about short term rentals as compared to a lot, you know, real estate investing as a whole, or just like many of the different ways to make a side income, you know, if you’re potentially looking to quit your job and want, you know, you want that cash flow that’s going to be at or higher than maybe what your job was, it doesn’t take a lot with short term rentals. Like, if you have a couple really high performing properties, it’s easy, you know, are relatively easy to get to that, you know, 567 $1,000 a month cash flow range, like you can do that with maybe one or two properties. Whereas with long term rentals, it’s really, really challenging, especially in today’s climate, with home prices, where they are with interest rates where they are, it’s just very difficult to really cash flow, where short term rentals if you do it, right, and I want to caveat it with like, you gotta do it, right. There’s definitely a right way of doing things and a wrong way of doing things. And, you know, for me through trial and tribulation, I’ve learned the right way to do things. But I also, you know, I work with others and help show them the right way of doing things. But if you do things the right way, you find the right property. And, you know, again, you’re trying to really supplement or take over your W two job like short term rentals is the way for that. At least I haven’t seen anything else. That’s better and quicker.
Brett
Fantastic. So the key is making sure you’re doing it right. You didn’t, right? And if you do it right, you can get that quick cash flow. And that, you know, and even just superior cash flow sounds like the number one secret there. So I guess, I guess it leads into the next question, what’s the number one secret to doing it? Right? Yeah, so being really, really good. So it’s definitely a whole process, it’s
Jeremy
an A to Z, at the first step, you gotta be able to identify what I call a winner, like a property that can just be a potential home run, you know, one that’s going to outperform and do 1000s More than, like, you know, the other ones around it. So, you know, there’s a variety of quantitative and qualitative ways to gauge that the software I use, you know, BNB calc that I built, it helps you quickly run the numbers. So, you know, be able to gauge if things are potentially a winner or not a winner, but that’s just the tip of the iceberg, you know, it is just identifying. There’s data, there’s data providers out there, but even the data providers, like the thing with short term rentals is not an exact science thing with long term rentals, a lot of times, you can have a really, really good idea of what a property is going to rent for on a long term, monthly basis, especially if you’re in a city with a lot different houses that are or apartments that are similar short term rentals. Like there’s huge variability, like I can buy a house and Brett you could buy a house, and we might buy the same exact house. And you might do $25,000 Better than I’ll say, you probably won’t, I’ll probably be the other way around at this point. But my point being is like, there’s just a lot of variability. And when there’s a lot of variability, there’s a lot of opportunity, the caveat being you have to do things the right way. So, you know, underwriting it, knowing what the amenities you need in the property are gonna allow you to beat out the competition, because ultimately, that’s what it is, if someone’s gonna Airbnb, you know, they’re looking between three houses. Why are they picking you know, my house first breads or why weren’t Oh, Brett’s house has a heated pool Where it mine just has a pool? Well, then they’re gonna go with Brett’s. So did that, you know, did that heated pool cost that much money? No, it was $5,000. If you’re gonna spend $5,000.20 $1,000 More in annual bookings, it’s a no brainer. So it’s just being able to identify what those key amenities are that are gonna allow you to outperform, and then creating the property and creating the experience that’s going to satisfy the client’s avatar that you’re looking for. So that’s, you know, setting up the property the right way, finding the proper the right property, and then it’s managing, you know, you got to make sure that you’re very attentive, it’s a hospitality business that’s different than long term rentals is, you know, it’s more akin to a hotel in the sense that you need guests to love staying there, you know, you need five star reviews, you need to know how to price your property, you need to know how to market it. You need to know how to, you know, have your, your local handyman and your local cleaners synced onto your system. So, you know, it’s not like you have to go there every day and clean it and take care of it. So it’s just the whole process from A to Z, but it starts with being able to identify and underwrite properties.
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About Jeremy Werden

Jeremy Werden is a firm believer in the democratization of alternative asset classes. During his time at the University of North Carolina, he was a passionate basketball player but realized that he wasn’t athletic or skilled enough to make the varsity team. After feeling lost and having tried different businesses, he decided not to leave his future in anyone else’s hands. So, at the spike of a pandemic, Jeremy invested in a single boat that solidly propelled his success and revealed to him an opportunity to invest in something more.
Nowadays, Jeremy is a full- time Airbnb investor with a 22-list portfolio. He does Airbnb arbitrage and co-hosting as well as buys properties for short-term rental, having a profit of over a million dollars per year. He has also built a software called Airbnb calc which helps Airbnb investors analyze properties. With over 117k followers on Instagram and 52.2k followers on Tiktok, Jeremy has called people’s attention.
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