LGBTQ+ Entrepreneurship & Short-Term Rental Mastery with Jason Muth

Mattias
(0:03) This is The Wealthy Investor Show, where we don’t just talk about your wealth. We also talk about your holistic health. I’m your host, Matthias.

Erica
(0:10) And I’m Erica. And this is The Wealthy Investor. Welcome back to The Wealthy Investor.

Mattias
(0:17) It’s just Matthias again, guys. I am sorry. Erica is with the kids.

Two of our kids are home right now, so if you hear some pitter patters upstairs and some yells, that is what she is doing. That’s our life right now.

But it’s a good thing in the sense that we realized yesterday—yesterday was Sunday—that we had two podcast guests scheduled today, and we had been recording everything off our dining room table.

So we were able to quickly decide that we’re going to paint my home office downstairs and create a more official studio. We are excited about having a more official studio set up that we can just come down, be separate, be away from the chaos if there are kids at home and everything, and be able to hit just record and go.

I apologize for watching our video. One thing I need to figure out is the recording thing. It is obviously glitching out and going crazy right now.

But anyway, we had a really fun guest today. Jason Muth, Erica was a supporter. She could not be on the phone conversation or on the Zoom conversation with him.

Jason is out of Massachusetts. He owns Airbnbs along with his husband Rory. They created a business called Prideaway Stays for Provincetown, Massachusetts.

Basically, they want to provide a service for people that really want to have a welcoming experience for the LGBTQ+ community for short-term rentals. Provincetown, I wasn’t aware of this, is a really awesome destination for people.

A lot of people want to buy property there. They’re very expensive as second homes, so people often seek to rent them out as an Airbnb on the side to make it more affordable. They are seeking to provide that service for people who don’t want to take it on themselves.

They are experienced operators and clearly understand what it takes to do this job well. We got into some different things. We got into how being a workforce, being an employee, can actually seem like a safe option, but it can be a more dangerous option if you’re only thinking about your career.

One of the ways that happens is that you become very specialized in your education and work experience, but if you’re laid off or something happens in that industry, all your eggs are in that basket.

We talked about how it’s interesting that people think entrepreneurship and doing your own thing seems more risky than having a steady job with a steady income. There are obviously pluses and minuses to both, but being laid off, which Jason will get into, is a reality with big businesses.

If all your eggs are in that basket, you can find yourself in a pretty bad position. So, Jason was laid off two years ago today, as he said. He took that as an opportunity—he was going to quit anyway—to transition full-time into real estate.

Since they had been buying and managing Airbnb properties since 2016, if you are not financially literate, it’s definitely something worthwhile looking into, no matter what your career is. If you are a realtor listening to this and you don’t understand what it means to be a real estate professional tax-wise, if you do not own rentals and you’re not taking advantage of being a real estate professional, that is one of the best things you can do to minimize your tax liability.

I highly recommend you look into this a little bit more. One of the goals of this channel is to help educate realtors about that. You don’t have to personally oversee renting properties for forced appreciation.

Again, going down a rabbit hole, look into accelerated depreciation, bonus depreciation as a tax strategy. You don’t have to buy property necessarily to do that, but you can invest in syndications, things like that, which will allow you to take full advantage of being a real estate professional. Jason said he went to a conference and they said the biggest tax strategy you can do is marry into having a real estate professional as your spouse.

If I’m talking Greek to you as a realtor or as a real estate professional, someone who mainly does real estate for their work and income, you definitely owe it to yourself to find out more about how you can take advantage of this designation that many high-income earners wish they had.

So, going back to Jason, Jason was a great conversation. He had a lot of great insights. If you are in the Airbnb space, it is very interesting. We spoke a little bit about how the market shifted through COVID and how it is now and some of the traps people fell into post-COVID with the numbers being really good.

So, yeah, stay tuned for this conversation. It’s great. Without further ado, Jason Muth. Jason, you’re coming out of Provincetown?

Jason Muth
(6:01) No. Provincetown is where we have some properties, but we’re coming out of Newburyport, which I did not tell you beforehand. So I don’t fault you for that.

But yeah, we’re about 40 minutes north of Boston.

Mattias
(6:14) And so you own Airbnbs in Provincetown.

Jason Muth
(6:17) Yes. We have four up in New Hampshire, not too far from here. Three of them are in Farmington, one is in Guilford, and then we have one in Provincetown.

The one in Provincetown inspired the business we launched last year called Prideaway Stays, which services Provincetown.

Mattias
(6:33) And that’s management for Airbnbs in Provincetown.

Jason Muth
(6:37) Yeah. I mean, we’ve been doing our own properties since 2016, which is when we bought our first investment. We bought into Provincetown in 2018.

I’m in a short-term rental mastermind group called STR Secrets, where we learn from the best people across the country with lots of amazing operators who run their own properties and co-host other people’s properties.

The mastermind connects people, builds our mindset, builds our network, and teaches us how to run co-hosting businesses. When I joined, I just wanted to meet people in the space and run my own businesses better, you know, the houses we had.

But once I realized I wasn’t fully optimizing what I’d been learning, I thought there was an opportunity in Provincetown. So, last November, a business partner and I built a brand and a website and started promoting the fact that we were going to manage other people’s properties.

We now have clients in Provincetown.

Mattias
(7:31) Okay. Cool. And what got you started on the path of real estate investing in general?

Jason Muth
(7:36) We started following Bigger Pockets back around 2015. In fact, we have a podcast ourselves, the Real Estate Law Podcast. We’ve interviewed several Bigger Pockets people on that podcast, including Dave Meyer.

I was telling Dave that my relationship with Bigger Pockets almost predates a lot of the people who work there now, because we built our profile back in 2015. I was interested in figuring out a way to diversify our income streams and invest some money that we’d been saving up.

I’d worked a W2 job my whole life until two years ago today, when I worked for someone else. We started doing real estate on the side in 2016. You can probably Google my name and find a podcast I was on by a gentleman named Kevin Amals, who we had on our podcast.

He titled the episode, “I Won My Down Payment Gambling,” which is kind of true, but not fully. We won about $15,000 and put that toward a down payment for a property. That has been a wildly successful investment that has turned into a wealth of understanding what the short-term rental space is.

It gets very addictive—once you buy one property, then another, and another, you start seeing things appreciate, you get good reviews, and good things happen on both the hospitality and real estate investing sides. Short-term rentals involve both; it’s not just buying a family home, installing tenants, renovating it, and refinancing it again.

We were accidental investors, half purposeful, half accidental. But once I realized how good it was, I was looking for a way out of my job. My job gave me that exit two years ago, literally two years ago today.

It was the exit I needed because now I do this full-time, and I’m wildly happy and life is amazing.

Mattias
(9:33) That’s fantastic. And so you said the first one was in 2016?

Jason Muth
(9:38) Yes.

Mattias
(9:39) We saw a flood of interest in short-term rentals during COVID. How’s that impacted your portfolio?

Jason Muth
(9:48) When COVID hit in 2020, we owned two properties and some land we aspired to build on. We had full calendars booked for the summer that got totally unbooked.

It kind of freaked us out because one of our properties had just been purchased a year and a half prior, and we had just gone through one full season with it. Suddenly, we were not paying multiple mortgages, and we wondered how the money would come in to pay

those.

But as the world has changed over the past four years since COVID started spreading, there have been many changes. The way we operate has changed. We needed to figure out a way to re-book our calendar and see what happens going forward.

So, it was a momentary freak-out, and then suddenly, once things started to reopen that summer, we realized that people were going to be doing more local travel.

Mattias
(10:57) It’s better ultimately for you.

Jason Muth
(11:00) Yeah, I mean, like the biggest year in short-term rentals was 2021. This has been documented by lots of studies. A lot of people are talking about it now.

Really, a lot of the conversations today about short-term rentals focus on how people are down compared to previous years. And that is true. People can now travel internationally again. They have more options with inflation where it is and prices where they are.

A lot of people have gotten into these properties over the past couple of years, and they’re having to charge more than people are willing to spend. When you look at the perfect combination of occupancy and rates, 2021 is the year people are measuring against.

It poses a challenge for many who have purchased properties in the past couple of years. We included, because we bought one of them in the past couple of years, and that is the laggard in our portfolio.

The problem right now is that people just can’t fill these places up like they used to with the rates they want to charge, and they have these high-interest loans to pay down. But anyone who bought before 2021 has seen tons of appreciation.

If you’ve optimized your systems, you’ve found a way to give a better experience to your guests, thereby getting better reviews and being able to charge more. We’re grateful we got in when we did because it’s been a pretty decent acceleration since then.

I just ran my numbers last night since we’re halfway through 2024. We’re actually up in our portfolio from last year, which I think is a pretty decent accomplishment because last year, most people were down. Some of our properties are down, but collectively, our portfolio is up.

Mattias
(12:55) That’s interesting. And yeah, you’re addressing exactly what I was getting at. I’m a realtor who services a vacation area with many vacation homes, and that’s the market that makes me a bit nervous.

That’s because I think a lot of people were buying. Prices went up in 2021, people had an influx of money, and money was cheap. There was a huge demand for Airbnbs, exactly for the reasons you mentioned.

People started running numbers based on those analyses. They saw amazing numbers, and this property was performing super well. So, they’re paying high for this investment property. If they come in and don’t see the same success in the next few years, with higher interest rates and all, it can start adding up.

I’ve seen more properties being listed, but I’m anxious to see if you think there will be a trend in some markets.

Jason Muth
(14:01) So, we know the Lakes Region in New Hampshire, specifically Guilford, New Hampshire, which is basically a Lake Winnipesaukee community, a classic vacation destination.

We’ve chosen to invest in places with a history of renting property short-term. Provincetown, people have been going to Cape Cod for a century. Where we are in Farmington is a lake area, so the town itself isn’t a destination, but the lake is.

We got in really cheap, frankly. We bought at the right time in Farmington and built a beautiful place. Our top-performing property is one we built two years ago.

We built it specifically for short-term rentals. It looks fantastic, and everyone loves it when they stay there. Things have come up, including a massive flood this year and a big insurance claim.

Thankfully, I had good insurance with a company that specializes in short-term rental insurance called Proper Insurance, not paid to say that. They certainly did everything they promised when I took a higher premium policy with them.

Guilford’s an interesting one. I was just looking at Guilford today, and another property came on the market yesterday. It’s a direct comp of mine, but it’s had a bunch of price reductions.

They priced it about $100,000 more than we paid two years ago. I wish appreciation was more than that because 5% a year can be achieved with a high-interest savings account with no frustration. But if I can get that as a comp, then you just keep going.

We have a high-interest rate loan on that property, which is the one dragging a little because we bought it in 2022. It was comped against 2021 numbers using AirDNA, a standard platform that financiers use.

We haven’t been able to hit the numbers AirDNA projected. We’re doing everything right, except putting in a hot tub, building a game room, or making it a mega property, which requires additional capital investment that we don’t think we’ll get back yet.

I think we’re fully optimized with this property. One thing we did well the past couple of years is getting fully optimized. We’ve squeezed as much as we can out of each of these properties, and hopefully, each year, it incrementally increases.

Our initial property, the first year when we had no idea what we were doing, brought in $24,000, and the same one did $72,000 or $74,000 last year. This is an under-$200,000 home that we bought. We optimized that one really well.

I think I got Guilford up to cruising altitude immediately because I knew what I was doing, was in the right network, and had my systems right. If last year’s performance is the best I can get going forward and it was 20% less than AirDNA’s projection, I’m not alone in that dilemma.

There are other people who are not as good operators as I am, using the same numbers, and they’re probably really underwater with those properties. So yeah, I think you’re onto something with what’s happening in some vacation markets. Let’s see what happens.

One easy way for things to normalize for short-term rental operators is for inventory to be pulled off the market and become long-term residential properties, but I don’t foresee that happening with some of these mega houses.

Mattias
(17:46) Especially if you’re in a vacation spot that has always been popular. That makes a lot of sense. When you say optimize, what are some ways you can optimize your vacation rentals? I imagine there are things like price fluctuations, up and down, with other strategies that might be helpful.

Jason Muth
(18:10) Dynamic pricing is a big thing people should use. Many people aren’t using dynamic pricing; they’re just setting one price and letting it go.

People also think about longer-term minimums and stick with them, being very rigid with how they’ve operated for many years. The basics right now: if you’re going to buy a property now or have bought it in the past couple of years and want to optimize, you need dynamic pricing.

We use PriceLabs for that. You need to understand the market, look at market data, price your property against that data and comps, and not over- or under-price your property. Figure out where you stand: are you a 50th percentile property, a 75th percentile property, or a 20th percentile property?

Then see what the market is selling at and position your property in that range using market intelligence. PriceLabs helps with that, and there are other tools that can tell you where you should be priced.

It’s not perfect, so you also have to use your intuition, which is hard to develop if you’re new to a market. It takes a couple of full calendar years to understand the market cycle. I recommend underwriting properties with about 45%-50% occupancy.

I met an influencer at a conference who thought every market should sell at 85%, but I’ve since seen some of his stuff and think he’s insane. I won’t name names. But those are the basics.

Realize that you need to up your game with customer service. We automate a lot of messaging, from booking to asking for reviews, to save time and frustration with rinse-and-repeat messages. We respond to all questions in real time and recommend others do the same.

There are many good hosts, but the bad hosts make it easy for good hosts to stand out. Bad hosts have grainy photos, don’t caption pictures, don’t describe the property well, and set poor expectations.

Delivering what you promise, or more, is a basic requirement these days. The reason people don’t get five stars all the time is that guests are underwhelmed by what they thought they were booking.

We have a 4.95 rating on Airbnb with 330 reviews because of consistency. The more five-star reviews you get, the more it balances out the occasional bad one. Optimizing your property is crucial.

If you don’t have professional photography, you’re leaving a ton of money on the table. Your iPhone won’t cut it. You can supplement your listing with a few iPhone photos, but professional photos are essential.

When I see people without professional photos, I think I’m going to run circles around their property.

Mattias
(21:49) Thank you. No, man, what a 101 for customer experience in general—over-deliver on what you promise and set expectations. That’s key to many business avenues, real estate sales included. That’s

excellent advice.

Tell me a little bit about how you maintain your mental health and wellness as you pursue your goals. You seem like a high-achieving person. What are your processes and systems for making sure you’re right to achieve more?

Jason Muth
(22:34) Yeah. That’s an amazing question. I’m glad you focus on that in your discussions on this podcast. Before I started working for myself, which was two years ago today, I only knew to work for others and try to get ahead there, work hard for someone else, and hopefully get that incremental raise or praise.

But we all have an expiration date if we work for someone else, whether we expire mentally and don’t want to work there anymore, or the company decides to go in a different direction. It’s always good to have a plan B.

I didn’t read a book on how to live my life building a plan B, but I was lucky to find the real estate side, and things were going well for a couple of years. So when my job ended, I transitioned directly into real estate without missing a step.

I invested more in myself and made a declaration to bet on myself for 18 months to see how it goes, launch this thing, get it off the ground, and scale it higher. It worked really well. I spent money on education and building a network.

We invested wisely, built that new house, optimized all our properties, and came out making much more money than I was earning working for someone else. We talked off-camera about real estate professional status, a tax strategy many in the real estate investing community use.

We didn’t optimize that initially. My husband is a real estate attorney and broker. A real estate attorney alone doesn’t qualify for the status, but being a broker does. So for a while, we filed as real estate professionals, with me having the W2 job and him having the real estate professional status.

It flipped a couple of years ago when I started doing this full-time. We continued filing with that real estate professional status. There’s plenty of information online about real estate professional status, but I learned about cost segregation studies at a Bigger Pockets conference, which was worth every dollar I spent going there.

We hosted people from Cost Segregation Authority on our podcast, which we use for our cost segregation. We’ve done a couple of them, allowing us to defer significant taxes to the future by taking bonus appreciation, which is 100% legal based on the tax code, and offset some of our active income.

We had to restate one of our tax returns from 2022, and it took 16 months for the government to send us that check back. Real estate professional status is something many real estate investors use.

We weren’t optimized because we didn’t know about it. It’s our fault. We had no idea that we were in that exact situation where a high W2 earner could be married to a real estate professional and offset some of that tax.

The joke at the conference was that the best tax strategy is marrying a real estate professional. We didn’t plan this.

Mattias
(26:34) To your point, I’ve noticed that many realtors I work with don’t fully understand that either. It’s a huge opportunity. I know that people who aren’t real estate professionals often use Airbnb as a loophole to try to get that real estate status.

It’s something else I can’t really talk about, but it’s worth researching if you’re not a realtor or a full-time real estate investor.

Jason Muth
(27:06) Yeah. Going back to your question about mental health and happiness, quiet quitting was a big thing a couple of years ago. People were giving up on their jobs and not really caring.

I wasn’t that deep, but I’d been doing it for so long and had reached the maximum I could get with that company and in the industry. If I wanted to go to another company, I could have, but I didn’t want to rebuild everything.

At some point, you start looking at the endpoint of your life. In your 20s and 30s, you’re building, accumulating, forming relationships, living your best life. Hopefully, you’ll live your best life until your final day, but let’s face it, I don’t know when my final day will be.

I’m in my late 40s now, so I’ve probably lived over half my life at this point. Now I can start looking at how I want to spend the rest of my days. I think I have a good 10 more years of building if I want to.

At some point, I want to stop doing all this and have someone else manage it for me, but I’m not fully there yet. I’m driven by my personal gratification that I’m doing a good job for myself.

I think it’s important to be a productive member of society, to be a provider for your family. We have a dual-provider household and a five-year-old daughter. We want to set a good example for her and be around a lot for her.

I don’t understand how people can work full-time jobs and be around their kids. It’s a huge struggle. We just sent our daughter to pre-K at the local school, and her day ended at 1 o’clock.

I was doing a lot of the pickups and drop-offs, and I don’t understand how I would have done that with a full-time job. It’s hard, really hard.

Mattias
(29:16) It’s so hard. Having the mental energy and the stress-free ability to be there for your kids in the right way is also challenging. A demanding schedule only increases that difficulty.

Jason Muth
(29:32) Yeah, and we’re not just sitting back, letting our investments do what they do. My daughter picks up on the fact that I’m working a lot.

If she sees me at the computer or on my phone, she knows I’m working. She’s started giving me a lot of verbal cues about the amount of work I’m doing, which is a bit of a bummer, but I’m trying to instill a work ethic in her.

I think it’s important that she sees how we earn money. She’s used to having multiple homes. We had seven properties at one point; we just sold one.

She goes with the flow and sees different houses. We’re fortunate to have that many properties. Most people either own their own home or don’t own one. I don’t want her to think it’s normal to have this many houses to randomly show up at and live in.

Not having that job anymore is great for my mental health. I don’t begrudge people who work W2 jobs. There are many online who say, quit your job and make billions drop shipping or whatever.

I think it’s important to build work skills. It might be my generation, Gen X, who had one foot in both the boomers and millennials. We saw the best of both and carved our path.

I met many people and learned a lot about what I wanted to do with my career. I worked in the media business for a long time. It was a great run.

The media business is tough, as you know. It’s very unforgiving. I always say it’s like a game of musical chairs where they take away a couple of chairs a few times a year.

Eventually, there are just a few seats left for everyone. But it was great with great memories and everything. Now I’m in my chapter two.

I haven’t looked back. A lot of what I wanted to do these past couple of years was rebrand myself into what I am now. It feels so natural to have these discussions about enjoying life, being around for your family.

We’re in a new community; we moved here two years ago to Newburyport. We feel really ingrained in this community. I also have a foot in the gay world in Boston.

We talked about that off-camera. I still referee in the gay flag football league in Boston, which just had its 25th anniversary. It’s a big part of my identity as well.

I have a lot of friends there. It’s important for me to have that escape. In the spring and fall, Saturday is my day to go there and see my people. It allows me to live a well-rounded life.

We all need things outside of work that we like to do. Those things really help keep me focused.

Mattias
(32:27) That’s interesting. My wife, a licensed therapist who couldn’t make it today, always talks about having a third space.

You have your home, work, and a third place where you have a community. It sounds like that could be your space. It’s a crucial energy-giving thing for us as tribal people. I have two follow-up questions.

Do you remember the moment you got the news about your job? Was it immediately seen as an opportunity, or was it hard?

Jason Muth
(33:17) Two years ago today, I got the call in my car after dropping my daughter off at daycare. We had just moved to Newburyport. Here’s the honest story.

We didn’t tell anyone we were moving here because it was none of their business. The office was moving farther away from Newburyport, and I had zero intention of spending more time there.

I wasn’t going to stay at that company because they were calling everyone back to the office. I did everything I could, but I wanted to move, close the mortgage, and then see what happened.

The craziest thing is if my job had ended before I closed, I couldn’t close the loan. But

if I closed the loan and the job ended shortly after, I could close the loan. It’s insane qualifying for conventional financing.

I got the call, received the package, looked at it, signed it, collected unemployment, looked around for a job because I had to, but I really wanted to try entrepreneurship next.

When I got home, I told Rory, “Oh my God, they just cut the job.” My next words were about the HELOC because we were applying for a HELOC on one of our properties. It was a quarter-million-dollar line we wanted to use to invest in other properties.

I thought I wouldn’t get that HELOC now, but I called the lender and explained the situation. They couldn’t qualify me for the loan without the W2 job. I couldn’t get that loan, but I didn’t care.

Real estate investors find a way. The equity is still there; I just can’t tap it. Let me find another source. The two things that bugged me were not closing on that loan and not hearing from certain people afterward.

There were people I expected to hear from, senior levels in that company, who didn’t reach out. It spoke more about their character than mine. I moved on, but I’ll never forget that.

Mattias
(36:38) Exit interviews and all that are things people probably avoid because they’re uncomfortable, but they’re essential. You can’t just ignore having built professional and personal relationships with people for many years.

Jason Muth
(36:59) Some people can, though.

Mattias
(37:02) You shouldn’t. The other question I have is, now that you’ve gone through your chapter two, what would you tell yourself at around age 20?

Would you want to be in this position sooner? What advice would you give yourself?

Jason Muth
(37:30) My generation wasn’t taught through the internet like many are today. There weren’t influencers. My first email address was in college. Social media didn’t exist until MySpace and Facebook.

It’s been 15-16 years since then. There wasn’t much information about financial independence and retiring early, the FIRE movement. If you don’t know what that is, you can look it up. I’ve told neighbors about it.

I would have tried to speed up by investing in real estate sooner. I was taught to work hard, go to a good college, and work my way up to retire at 65. Nobody told me there was another way.

Maybe I should have found out myself, but I think financial education is severely lacking in schools, high schools, and colleges. They’re teaching the wrong stuff sometimes.

I went to an Ivy League school, Brown University, and didn’t get that education. I think the generations after me have been instilled with more entrepreneurship. Brown was a great school, but we’re not teaching people the right tools to succeed independently.

The college culture is to go into the workforce, as it should be, but it’s always to work for someone else. I might have tried to find my way to entrepreneurship sooner.

That would be one thing I’d tell my 20-year-old self: listen, you’re getting into this industry, which is rough and not growing, but it’s fun. Look for your plan B sooner rather than later.

I was fortunate everything worked out. There were a few job stumbles along the way, but I always found the next step. But nowhere along that way did someone say, start building your plan B.

I found that out myself. I wish someone had shaken me and said, build your plan B, build your plan B. I see a lot of my former coworkers who don’t have their plan B, and it’s going to be on them if and when that day happens.

That happens to a lot of us in many industries. That’s what I would say.

Mattias
(40:29) Yeah, I’m writing a book right now, and I’m rereading “Rich Dad, Poor Dad” by Robert Kiyosaki. He talks about ultra-specialization, which is what universities and schools train you to do.

You get into your career and become ultra-specialized. He argues that it makes sense for unionization in that area because if you lose that, what do you have? That’s exactly what you’re talking about.

He also talks about building up your assets and having a side hustle or plan B. It seems like the more secure route is to get specialized and get education, but it’s less secure in many ways if you think about it.

Jason Muth
(41:20) Yeah, companies will look out for themselves, and that’s always been the case. Company culture is important, and it’s important to build a great resume by working for amazing employers.

People can make a ton of money working for others, especially in high-level roles, VP roles, sales roles. Money isn’t the driving factor for many people. What drives me financially is seeing the numbers and feeling secure that I can do what I want.

I don’t live an extravagant life. My car has 118,000 miles on it, but I love it. It’s an orange Jeep Cherokee. Everyone knows I’m there. I’ll drive it until it doesn’t want to drive me anymore and then find another car.

Some people are driven by possessions. We have a nice house and rent out nice houses. We took a cruise a couple of weeks ago that we booked two weeks prior because we wanted to. We can do that kind of stuff.

But we don’t live over the top extravagant because that doesn’t matter to me. I don’t need that level of material possessions. But some people really need that, and again, to each their own.

What drives me is feeling I can afford the things I want when I want them.

Mattias
(42:43) Yeah, and like you said, the freedom. That’s what motivates me too. I like having nice things, but the freedom to do things, like taking our family to Spain for a year, is a big motivator for me.

Tell us more about Prideaway Stays and what you aim to achieve there.

Jason Muth
(43:15) Prideaway Stays launched last year. We saw a gap in the market for an LGBTQ+-owned short-term rental co-hosting business in Provincetown. Provincetown is one of the gayest places in the country, unabashedly.

Many people aspire to own property there if they’re regular Provincetown visitors. They want to retire there or have a place in Palm Springs and Provincetown, or Florida and Provincetown, and go back and forth.

Real estate is very expensive in Provincetown, and your dollar doesn’t go far. You’re not getting a palatial estate; it’s a lot smaller, but it’s a magical place where you can be who you are.

It’s an old fishing town with a lot of Portuguese heritage. It’s a classic Cape Cod vacation destination with great restaurants, vibrant atmosphere, and scenic views.

Our thesis was that some owners in Provincetown don’t know short-term rentals as well as we do and might want to work with an LGBTQ+-owned company. National companies have been experiencing layoffs and customer service issues, as seen in their earnings reports.

We could do a much better job with better customer service and local relationships. We own property in Provincetown, pay taxes there, and are frequently there. People don’t invest in Provincetown for strict cash flow; it doesn’t behave that way, especially with current prices.

When people buy into that market, they’re looking to use their properties and offset the mortgage and taxes by renting them out when not using them. Many recent buyers need rental income to afford their property. That’s just a fact.

Unless they’re paying cash or are independently wealthy, most people need to rent their properties out. We want to help them if they want our help. If they want to self-manage, fantastic.

But many people don’t have the time, effort, or understanding to self-manage.

Mattias
(46:18) Right. There’s a clear skill in optimizing rentals, as you mentioned.

Jason Muth
(46:25) Not everyone feels that way. Many self-managers do a great job because they have the time and interest in it.

They might not like their job and want to see if they can make a go of it with a rental property. They’re meticulous with the design, communications, and other aspects. I applaud them for that.

Prideaway Stays aims to have a boutique business serving Provincetown and not get too big too fast. It’s not our primary income stream, but it’s a great supplemental way to build credibility, expertise, help others, and make some money.

We launched with modest goals, picked up clients this year, and will likely do more outbound marketing after summer. Our thought is that people have had either a good or bad experience managing their properties. So, why not be there with another option?

We did a lot of marketing in the first quarter and received a decent number of calls, leading to several clients. We like how things are going so far.

Mattias
(47:48) That’s great. It makes a lot of sense. Everybody dreams of the beach house they’d rent out, but it sounds like your clients are primarily focused on second homes. That’s an interesting niche.

You mentioned your husband is a real estate broker and attorney. Does he help with the sale and purchase of these properties?

Jason Muth
(48:17) Yes, he’s been involved as a broker or attorney in most of our

personal transactions over the years, whether I was buying, we were buying through an LLC, or buying together.

He runs a brokerage, but it’s been quiet lately due to the market. He’s invested more time in the law side, handling closings, land issues, and other real estate attorney work.

I don’t know what he does all day, every day, but we have a podcast together. We launched it in 2019 as a way to build credibility in the space. It’s helped me a lot as well, developing my own expertise.

Some people think I’m the attorney, but I’m not. It’s just the name of the podcast. We’re almost 200 episodes in and continue to stick with it. We think it’s a good listen.

Mattias
(49:26) We’ve found doing the podcast together to be a lot of fun and a way to connect. It’s been a really fun thing to do, and I imagine it’s similar for you all with the business and rentals.

Jason Muth
(49:44) Yeah. We always talk about the podcast and how much we’re each putting into it. I book the guests and deal with the production afterward.

We have producers who handle everything and manage the social media, which Rory doesn’t enjoy doing. Last week was my big podcast thinking week.

I have an AI thinking week coming up. I don’t usually do this, but I wanted to put something on the calendar to focus on this topic. In two weeks, I’ll think about how to improve using AI in all my businesses.

Last week was a deep dive into the podcast—looking at the stats, the guests, and whether it still brings us joy and serves our business purpose. We talked about a few things we could be doing differently with the podcast.

A guest on the podcast said something amazing about podcasts: having a podcast is the ultimate cheat code to building a network. It’s a great way to connect with people you’ve had on the podcast, follow up, and maintain a relationship.

It’s an easy way to be in someone’s inbox, send a text, or connect on LinkedIn. You’re not just a random person selling something; you had a meaningful conversation for an hour and gave them a platform to talk about themselves.

Most people appreciate that, and I promise I’ll take your calls in the future when you reach out.

Mattias
(51:39) Well, it’s 45 minutes in, and I haven’t burned that bridge.

Jason Muth
(51:42) No, I’ve enjoyed this so far.

Mattias
(51:47) It’s been a great conversation. For those who want to use your services or reach out, where’s a good place to follow you?

Jason Muth
(51:55) My website, jasonmuth.com, has everything. Prideaway Stays is the business in Provincetown. If you Google Prideaway Stays, you’ll find it easily.

If you’re curious about our personal properties or looking for mentorship to launch properties without us co-hosting, visit straightforwardshorttermrentals.com. You’ll find our five beautiful homes and more information about us.

You’ll also see my daughter featured in our marketing because why not, right?

Mattias
(52:39) We’ll link those in the show notes. It’s been a great conversation. Thank you so much for being a guest with us.

I hope we can stay in touch as we continue on our journeys toward financial freedom.

Outro
(52:56) Thanks for listening to The Wealthy Investor Podcast, where we talk about wealth and holistic health. If you enjoy our content, subscribe wherever you get your podcasts and hear new episodes every Thursday.

If you really like our content, follow us on social media at The Wealthy Investor, spelled W-E-L-L-T-H-Y.