Intro to the STR Pros Podcast with Jeremy Werden

Quick Summary

The podcast, now titled “Short-Term Rental (STR) Pro Podcast,” is hosted by Jeremy Werden, a 26-year-old entrepreneur running a seven-figure short-term rental business. The episode introduces the purpose, format, and Jeremy’s personal journey, aimed at educating and empowering listeners to succeed in the short-term rental industry.

Key Points

• Transition to a New Podcast Format: The podcast has evolved to focus solely on the short-term rental (STR) industry, offering actionable advice and tips.
• Jeremy’s Background: Jeremy shares his journey from failing as a basketball player to building a thriving business, highlighting his struggles, failures, and ultimate success in STR.
• Insights into STR Strategies: The podcast will cover diverse STR opportunities such as Airbnbs, glamping, boat rentals, and arbitrage while emphasizing financial literacy and independence.
• Mission and Purpose: Jeremy aims to inspire listeners to achieve financial freedom, offering practical guidance on running STRs and fostering a supportive community.

Full Transcript

Check out the full podcast on:

• YouTube
• Spotify
• Apple Podcasts

Check out the Full Podcast here.

What’s up, guys? Welcome to the Short-Term Rental Pro Podcast. I’m your host, Jeremy Werden. I’m a 26-year-old seven-figure short-term rental business operator, and let’s get to it!

This is the first episode of the podcast in this format. Previously, it was the Jeremy Werden Podcast, but we’re niching in, guys. I’ve been listening to you, hearing what you want to hear about, and that is short-term rentals—whether it’s my Airbnbs, my boats, or my glamping campers.

That’s what you guys want to know! You want tangible tips and advice to help you grow your business and take it to the next level, whether you’re starting from scratch or you’re already full-time.

So, that’s what we’re going to do. I want you guys to know what you can expect from me: I’m going to give you guys my all. You’re going to learn a ton about short-term rentals—whether that be how to start from scratch or grow your business from millions to multi-millions.

I want you guys to learn from my personal trials and tribulations, as well as other experts in the field. I want you to get tangible tips and hear motivating stories. We’re going to bring each other up and be there for one another, along for this ride—not only in the short term but the long term.

So, what is this show about? It’s about becoming a Short-Term Rental Pro. Whether it’s Airbnb or other creative short-term rental businesses, it’s about helping you succeed today and into the future.

Whether you have a lot of money or a little, it’s about discussing, comparing, and contrasting the various Airbnb and short-term rental strategies. With Airbnb, you can buy properties, rent properties from landlords, or manage properties for homeowners. You can do boutique hotels, glamping properties, or resorts.

There are also other short-term rental businesses: there’s Turo, which is car rentals; boat rentals—I have seven boats that I rent out; and there are camper rentals—I have an Airstream camper I rent out. I actually don’t let guests move it; it stays stationary. But I have friends in this space, peers who rent out camper vans, and have made a ton of money, reaching financial freedom through van rentals.

What we’re going to do is think about how to quantitatively and qualitatively analyze deal opportunities. That’s something that was very important for me early on. When I was getting started, every single deal and decision—whether it was a new business or a new property—had to be incredibly well-thought-out. I had to be precise with my projections and execution.

We’re going to think about short-term businesses for long-term investing. Ultimately, guys, we’re in this for the long haul. If you’re listening right now, you don’t want to retire when you’re 75 years old. You don’t want to rely on that 401K.

You want an alternative. You’re just like me. You couldn’t sit at your desk from nine to five every day, watching the clock, waiting for freedom when you have gray hair. You want it now.

So, if that’s you, you’re tuned into the right place. You’re tuned into a place where we’re getting out of that nine-to-five grind and creating ventures and lifestyles that give us time and location freedom.

What is the format for this podcast? I’ll do solo episodes on specific topics that you guys request. It could be anything! Shoot me a DM on Instagram. Go to my profile, @JeremyWerden, and send me a message. If you give me a topic request, at some point, I’ll go deep.

We’ll do solo pods on topics you guys request, and I’ll also do interviews with thought leaders and experts in this space. This might be Airbnb hosts, service providers, or other folks doing different types of short-term rental businesses.

I’ll have conversations with interesting people who are action-takers and who have perspectives that will be valuable to you.

About me—who am I? What is my background?

I’m a full-time short-term rental investor. I’m 26 years old. I started my short-term rental businesses at 23. Within a year, I was able to quit my job, and within three years, I grew my annual revenue to over a million dollars.

I have 25 Airbnb listings that pull in over a million a year. I have seven boats and one camper. I’m continually adding to my portfolio, looking at new opportunities and new business ventures.

I’m going to discuss everything I’m doing with you guys so you can stay updated to me and my growth in real-time, and that is going to contribute to and help facilitate your growth as well.

What is my story? What is my background? How did I get to where I am today?

For those of you watching on YouTube, I’m in New York City at a recording studio. I’ve got my producer, Wolf, in the house—a total beast. Check him out. He’s a stud.

So, what’s my background? Who am I?

I was born in New Jersey. I was initially a Jersey boy, born in Trenton, and then I moved to North Carolina when I was almost nine years old. I grew up in North Carolina, grew up loving sports, and loving basketball.

I went to the University of North Carolina, where I was on the junior varsity basketball team. For most of my life, basketball was my passion—that was pretty much the only thing I cared about. I’m extremely appreciative and grateful to my parents that they let me put my passions first.

I did have to work growing up. I had a landscaping business, and I babysat because they didn’t give me money—I had to make money myself. But in terms of eating, the necessities in life, and their support—like driving me to practices and games, stuff like that—huge props to my parents.

In college, I went to the University of North Carolina and played on the junior varsity basketball team. My goal was to make the varsity team, to really make it to that next level. I dedicated myself to my craft, but it did not work out for me.

Unfortunately, my peers were better and more athletic, and they made it. A couple of them made it, whereas I did not.

When I knew I wasn’t going to make the team—and really, my life’s goal and ambition up to that point wasn’t going to play out the way I wanted it to—I needed a new goal, dream, and aspiration. That’s just the way I am. I need a passion, I need a purpose.

So, for me, the first thing was: All right, I need to get a good job. I need to get a good internship.

At the time, I actually had pretty decent grades. I was studying computer science. On paper, I thought I would’ve been a good applicant for a lot of different roles at different tech companies.

I was totally wrong. I got rejected for every internship I applied to. I even actually got rejected by the company my dad had worked for the entirety of my life—literally since I was a baby. My dad had worked for a tech company.

I thought, again, I was qualified. I did not get the internship. I did not get the other ones either. I literally was stuck that summer without an internship, so I had to start reaching out, looking for different things to do.

This kind of initially put me down my path to entrepreneurship. I went to San Francisco, where I worked with a program there, helping them do marketing and video editing services.

At the same time, I was starting a digital kind of—I would, you know—I had a computer science background. I had friends who were graphic designers, so I partnered with them to start an agency called Darkroom.

We actually built an internal tool software that failed. That was like the first thing we built. We built a company called Syllabi. It was a digital syllabus application, and that failed, too.

So, I was kind of working on a business here while also trying to help out another business. Really, I was just trying to get involved in that entrepreneurial world—not even by choice, but rather by necessity. I didn’t get any internship. I didn’t have basketball anymore. I needed to do something.

So, I tried my own business. It failed. We had clients that we would help out and started experiencing what real business was like, working with actual companies, which was really cool.

It was definitely hard at first. We had no track record, no credibility, but we were able to eventually start proving ourselves and gaining real clients. A year later, Darkroom was a legit business.

By myself, again, my junior year of college, I gave myself to that business. At the end of the year, I was going to actually move in with my co-founders and really go at it full-time. But essentially, that did not work out.

Not to get too much into it, but there were four of us. I had a vision for the company and the way we should go. The other three had a different vision. I was outranked, so I left.

I ended up doing freelance on my own. At this time, I was really hurt and thought, I gotta do my own business. I had no money, no resources, so I started working on my own for clients again.

I actually had decent success. I had a couple of bigger projects—at the time, for me—worked for a lumber company out of Atlanta and rebuilt their website. I made a little bit of money, which was good for my senior year in college.

Actually, one of my clients was a finance startup in New York, and I joined full-time, so I thought. I was really excited, working for a cool startup and learning about investing. To me, I never really knew much about investing. Obviously, as a kid, I played with stocks a little bit, but not with serious money, and, honestly, I was not very good at it.

I didn’t go to school for finance and actually had no formal finance training, but working for this private equity startup was my finance 101. I was blessed to be working alongside very bright people who were thought leaders in the investing field, in private equity.

I learned about leveraged buyouts and how all these pioneers had made so much money in the last 30 years utilizing leverage. It was a really great experience, and I learned a lot.

However, in 2020—so I graduated school in May of 2019—and then in 2020, the world changed. COVID hit. The startup that I worked at we were facing challenges in raising more funding. For those of you who know that time, a lot of people’s outlook on things was just bleak, and companies needed to conserve cash.

I was one of the only salaried employees at the time, and I got a text one day that my salary would need to be cut immediately. This was a gut punch for me—a realization that I needed to do my own thing. No more doing things for other people where they have the say, they have the control. They were the ones really in power over my happiness, financial freedom, and destiny.

I didn’t even care at the time what business I was going to do—I just needed to do a business. So, I reached out to some of the former clients I had and started doing more freelance web projects.

At the time, this was March 2020, and I had a lot of time. I was watching Ozark. For those of you who don’t know, Ozark is a TV show that takes place in a rural lake area in Missouri—or “Missoura” if any of y’all are from there.

In the show, the character Marty Byrde has to start businesses to funnel money for the Mexican drug cartel. That part of the show wasn’t what intrigued me, but the part just doing business at a lake did.

I lived in North Carolina and had moved back home with my parents when my salary got cut. The lake that I had grown up going to looked very similar to the lake in Ozark. That got me thinking: What business could I start at this lake?

The idea that came to mind was a boat rental company. I felt like there was demand. We had wanted to rent boats before but hadn’t been able to. So, on a whim, I bought a pontoon boat started renting it out. Bought it for $5,600 and started renting it.

A lot of the folks renting the boats either owned lake houses or were buying them. I got into conversations with them about helping with rentals for their properties. Literally, just through talking to customers, talking to people, building connections, and building relationships, things started to grow.

I would take people out for beers, you know. I would actually meet them in person, and they would trust me—hand me the keys and say, “You got this. You can be our rental guy.”

At the time, honestly, it was more like VRBO. Like, “You can be our VRBO guy.” Later, I kind of really dove into Airbnb. So, I started by leveraging other people’s properties, renting them out, and I was eye-opened. Holy crap, these properties were making a lot of money. Geez Louise!

As a co-host or property manager, you get a percentage of that money, which is cool—you know, a great 20%. But you don’t get the same benefits as owning. For me, my goal was: I gotta own. I want to own real estate. I don’t want to rent real estate. I don’t want to manage. I want to own.

So, really, in 2020, I started trying to figure out ways to go out and buy properties. What I figured was, hey, I don’t have the cash. I put all my money into boats.

I started with that one $5,600 boat. By the end of the summer, I had three. I literally reinvested all my cash into boats. I bought two more, and then I was managing other people’s properties to make additional cash.

So, I needed to raise money from people, and I needed to have banks give us financing. I had to be very creative about how to raise money and how to buy real estate.

Again, my background from the year before—working within an investment company that was raising money—was super valuable. So, guys, what you’re doing today can develop skills that will help you in the future. My previous experiences have really helped drive the knowledge and business that I have today.

I started buying properties. In addition, I would rent properties from landlords and re-rent them. This is known as Airbnb Arbitrage. The benefit of that is it’s a much lesser cash investment than buying.

You can put a lot of the expenses just on a credit card. You don’t have to pay a mortgage, you don’t have to pay a down payment on a home. You just need to pay that deposit, pay that first month’s rent, and then, a lot of times, you can put that furniture on a credit card. Which is what I did.

So, I really got into buying Airbnbs, co-hosting Airbnbs, arbitraging them, and I got into glamping—which is high-end camping. I bought and renovated an Airstream camper and put that up on Airbnb.

Today, I now have a 25-listing Airbnb portfolio. This is composed of about eight properties that I am a co-owner of. The rest are arbitrage, co-hosting, and glamping.

I have also grown the boat business to include seven boats. The boats are now only on a lake where we have houses. We did expand the boat business to two lakes, but I decided to actually focus on the Airbnbs and growing that while consolidating our boat operation to the place where we have a lot of houses.

All this being said, I have grown this business in the last three years. I have partnered with other people, raised money from them, and shared skill sets to really take this thing to the level we have taken it. I’m going to continue to take things to the next level in the future.

I’m super stoked to have you guys along with me for this ride. What I think is very important is to tell you guys—what is my purpose? You know, what’s my purpose in life?

You know, guys, we’re all here. We’re on this Earth at the same time, which, if you think about it, is pretty crazy. The Earth has been around for billions of years—or millions, I’m not sure, honestly. But the universe has been around for, I don’t know, tens of billions of years, and we’re on this Earth together right now.

I’m kind of under the belief that if you’ve got one life, you’ve got to give it your all. There’s no reason to be stuck in the system, stuck at your desk. You’ve got to create your own destiny.

So, my goal is to empower you guys to change your life. I’ve taken that first step, and I’ve been blessed to see success so far. Don’t get me wrong—there are going to be trials and tribulations moving forward, but I think you guys don’t want to live a life that you have no control over.

You want to go on the road less traveled. So, my purpose is to give you guys the knowledge and resources that you need to succeed.

I’m a big believer in financial literacy. I think, you know, the U.S. is a capitalist country. You hate it, you love it—it’s the case. You know, before my time, before your time, that’s how they built the system.

You can argue about the pros and cons of everything all you want, but I think our country has lasted several hundred years, relative to some other countries in the world that have had a lot of issues. You know, we’re in a decent spot, and you’re in a spot to create your own destiny within the framework of the country and the capitalist society we have.

But what don’t they do when you’re young in school? They don’t teach you financial literacy.

I never had a financial literacy class. I don’t know if any of you guys listening—well, did you ever have a financial literacy class? Yeah, it’s crazy because we live in a capitalist country. Like, we live in a very specific system. Why aren’t there tools and resources instilled in you at a young age to succeed in the system that we’re currently in?

So, that’s my point to you guys—just to give you the tools and resources to succeed. That’s my ambition, that’s my purpose, that’s why I’m here.

If you guys are going to take anything away from this, I want it to be tangible—tangible knowledge, tangible tips, and motivation to get the job done.

So, my goals for the future are to bring you guys along for the ride and have us come up together. We’re all on the come-up. Stay tuned.

I’m going to be posting once a week. I’m going to be consistent with this, so you guys can count on me. Hold me accountable, but I’m going to be a reliable source of information for how to grow a short-term rental business.

And, guys, I want to get into why short-term rentals—why I believe short-term rental businesses are the best type of businesses to start.

There’s obviously, you know, drop shipping, and there are all these other things, but to me, invest in the tangible. That’s something I’ve said for years. I’ve been consistent with this. \

Back in 2020, there was all the hype with crypto. You know, everybody was making all this money with crypto—they didn’t even know what they were making money with.

Real estate and short-term rentals are tangible things. They’re consistent. You are creating experiences—real-world, life experiences—for people.

Drop shipping? Sure, you’re giving products to people, finding little arbitrages online. I haven’t done it myself, so I can’t speak to it, and I’ve heard from other people that it’s gotten a lot more difficult.

But with short-term rentals, you are creating real-life experiences. Whether that’s Airbnb-furnished rentals, boat rentals, or camper rentals—whatever it is—you are providing experiences. People pay for experiences, and that’s only going to increase over time.

People want connection, and what better way to connect than to rent a house with 10 of their friends and enjoy life together?

People really want Instagrammable experiences—things they can take photos of. So, again, boats—you’re out on the boat with your family, snapping some photos. That’s lifelong memories.

Airbnb experiences? You’re staying at a cool property that’s really unique, and you’re there with your loved ones, snapping photos. That is a lifelong memory. So, that’s what we’re tapping into. That’s really the only business where we are essentially creating happiness and lifelong memories for people.

Obviously, that’s a qualitative thing, but think about it—that’s really neat. If you can start a business that is creating happiness for people, to me, that’s amazing.

As for the economic benefits of starting a short-term rental business, they are there. The main thing is predictable monthly cash flow.

You underwrite these properties. Whether you’re doing co-hosting, arbitrage, or buying, you can get into an opportunity and have a pretty good idea—if you know how to run your numbers the right way—of how much cash it’s going to put in your pocket each month.

Obviously, I don’t want to take away the importance of execution, because execution is key. You have to actually deliver. It’s not just because you put a pen on paper and wrote down that it’s going to make money that it actually happens.

Again, you’re providing these real-life, tangible experiences. You’re having guests who love you, love your properties, and love what you have to offer. They’re giving you five-star reviews, so others are now going to trust you and see you as a reliable source to park their dollar.

The money is great—it’s predictable cash flow. If you’re going to buy properties, there are huge tax advantages and huge appreciation advantages. But if you’re getting into an Airbnb strategy like arbitrage, it’s predictable monthly cash flow.

For me, for context, pre-COVID, I was making $3,500 a month. It was a startup. I got equity, so I definitely sacrificed how much I was making in return for believing that this business could grow and become a really interesting, big business.

So, that was my calculus at the time. But then my salary got cut to twenty-five hundred dollars. I bought a boat that first week for fifty-six hundred bucks and rented it out. I rented it out that first week. So, I bought it for $5,600, and then I rented it out that first week for two thousand dollars.

For me, I was like—and I, you know, I dropped the keys. At that time, I did a little bit of orientation. I showed the folks how to use the boat, and then I left. I just left. I went home and thought, Holy crap! I just made two thousand dollars, which is as much as I make in a month, by literally just dropping keys and showing the folks how to use the boat.

To be frank, I don’t even think they— it was March, so it was kind of cold—I don’t even think they used it that much. But to me, that was mind-boggling.

And that’s the nature of this business. You know, I rent properties for fifteen hundred dollars that make forty-five hundred dollars a month in revenue. That’s, you know, after expenses, two thousand dollars a month of cash flow.

And it’s properties where I haven’t been there in seven months. I was there. I set it up. Now we have a cleaner. Now we have a handyman. I don’t actually know because that’s an arbitrage property, so the homeowner—a lot of times the landlord—does a lot of the maintenance items.

So, it’s crazy. I just set up the property, I ran the numbers, and I made it look nice. Our design is really, really good. So, I set it up, and now it just makes me two thousand dollars a month—cash in my pocket.

I don’t really have to do that much for it. You know, every once in a while, something happens. Don’t get me wrong, I’m not going to make everything appear like total sunshine and rainbows.

But really, for the most part, I don’t do all that much. It just puts cash in my pocket. And again, I have 25 listings now and seven boats. So, I have 32 assets that literally just sht happens, I’m sure more sht will happen, but for the most part, their jobs are just putting cash into my pocket.

My job is to create the teams, systems, and processes to ensure that our customers—the ones paying this premium for this turnkey experience, are having a great time and leaving us five-star reviews.

If something happens, let’s say there’s some sort of damage, we have processes to deal with that. If an issue happens with a neighbor or something, we deal with it. We just deal with things. That’s what we’ve built—the infrastructure to optimize our pricing, guest communication, and maintenance. And when sht happens, we take care of it.

It’s a crazy business in that sense because you can do it from anywhere. Right now, I’m in New York City. None of my properties are in New York City. My girlfriend is in New York City, which is the reason I live here.

It’s a business you can do from anywhere in the world. I have my laptop on my lap right now because this table is too low, and I can’t see my notes, but I could be halfway around the world. I could be in Bali. All I’ve got to do is have my phone available in case something happens—which, honestly, doesn’t happen all that often.

That being said, short-term rental businesses are ones that give you location freedom, which is something super important. If you do it right, you’re not locked down to a specific geographic area.

In the last, just to tell you guys where I’ve been, since, I’ll start from October of 2021. In October, I set up a property in Florida and had it finished right before Christmas.

It was a pretty extensive renovation. It was one of our Florida houses with a pool—really beautiful. I did that property, left, and then I was actually planning to go to France with my girlfriend for the next few weeks in January. But then, actually, she had an ACL issue, so I didn’t do that.

I did travel, though, over the next couple of months before setting up two more properties—one in the Smoky Mountains and one again in Florida.

At that time, I also set up two arbitrage properties. So, I was really setting up properties even before that, but up until May. Then, in May, I was like, You know what? Buying properties is pretty extensive, with renovations and stuff like that. I want to take a chill pill on buying and just focus on arbitrage.

I did that for a few months, adding more portfolio properties, and then in November, I bought another one. I actually bought the property while in Paris, France.

So, I ended up going on that France trip. I also ended up going to Montreal. I learned French, which was one of my goals. From a cultural perspective, I’m trying to connect with new people in new places, and learning languages is a great way to do that.

I spent a lot of time in these foreign countries and was even able to create a process for buying a property remotely and setting it up. That’s really cool because three years ago, I would’ve thought, There’s no way in hell I’m going to close on a property from Paris, France, renovate it, and set it up. I would’ve thought that was absolutely inhumane or just unrealistic. But it happened.

So, that’s where I’ve been—traveling and setting up properties.

This year, I’ve set up several more arbitrage properties. We’re in April now, and I’ve already set up several more. I’m going to buy another property soon. We’re gearing up for the high season right now.

I generally don’t grow the portfolio as much during the peak season of the year, just because things are busy. This is when we really, really make the majority of our money.

I’ve also built software, BNB Calc, to help myself initially run the numbers on deals. Guys, I think I said this earlier: For every opportunity or deal you do, you want to be precise with your analysis.

The old way of doing things sucked for me, which was Excel spreadsheets. It was very hands-on and slow. I knew there must be a better way to underwrite Airbnb deals.

So, shoutout to Parker, my college buddy. We partnered together and built innovative software that makes it as quick and easy as possible to run the numbers on Airbnb properties. We got that up and running, I think, in August.

So, when I say I took a chill pill on buying and setting up properties, what I mean is I made it so my virtual assistants could handle everything with the houses.

For example, I’ve been here talking for two hours and haven’t responded to a single guest message or anything like that. My virtual assistants cover that. They handle ordering supplies, putting in maintenance requests—they just deal with the things I don’t need to be dealing with.

So, when I did that, I was like, Now I can build a software company. I can travel while building a software company.

So again, really, the freedom component—I’m not trying to understate the freedom component—of short-term rentals: location freedom and financial freedom.

The software company, BNBCalc, I talk about it a lot—check it out. It’s the easiest way to run the numbers on properties at scale, which is super important if you’re getting into the game. Making sure that you have all the revenue and expense variables as known variables, versus like, I don’t know what’s going on here.

It’s about the brass tacks, guys. It’s about the dineros.

So, I built software, and I’ve been growing the portfolio. I actually do have a coaching program where I work with very select folks and help them accomplish their goals. That’s really the purpose of the program—helping folks accomplish their goals using short-term rentals and, again, achieving that financial freedom and time freedom through short-term rentals.

We’ve had so much great success so far. Actually, on one of our mentorship calls yesterday—I think there were eight of us on the call—we had a variety of updates. Two folks on the call were literally assembling furniture at their new properties. Three others had listed properties in the last two weeks, and the properties were doing well.

They shared their success so far, with the amount of bookings and how much cash flow they project in the first few months. Someone else had another listing from a couple of weeks before.

It was just crazy seeing that this is actually a community of action takers, which is awesome. That’s who I want to be working with. That’s who I want to be talking to—people making it happen.

We did an in-person mastermind about four weeks ago, which was awesome. I loved meeting people in person. I hope some of you guys listening here—I hope to connect with you virtually and in person. That would be awesome. That’s where I think real, meaningful, lifelong connection happens.

Actually, during that mastermind, I was going through kind of a tougher time. My dad was going to have a heart procedure that upcoming week. To be frank, my dad—that dude’s my rock. He grinds. He’s super supportive, a great listener. He’s my absolute rock.

I might start crying here talking about that, but he’s had heart issues. One of the folks in our mastermind is a doctor, and he knew exactly what my dad’s procedure was. He knew everything about it, and he just assured me that it was going to be all right.

I’m going to respect and love that dude forever because I wasn’t in a good place. Again, that’s just the value, to me, of in-person, real connection.

I hope some of you guys listening—this is only the start—but I hope we have that connection. I hope we help each other grow and become the best versions of ourselves, from a business and short-term rental standpoint, but also from a human standpoint.

I know this has been a lot, and I appreciate you all being locked in with me still.

For this podcast, you’re going to get tangible tips, tangible advice, and hear from real people who are building short-term rental businesses. They’ll also share real-life stories that might help motivate you and help you take your journey to the next level.

So, thank you guys for tuning in today.

Again, this is the STR Pro Podcast—no longer the Jeremy Werden Podcast. We’re going all in on short-term rentals, and y’all should stay tuned and go all in on short-term rentals with us.

Super excited for this and super excited for you guys to be along for the ride. Stay tuned for next time!