I had the pleasure of sitting down with Jason Muth, a former media executive turned thriving short-term rental entrepreneur. In this conversation, Jason opens up about transitioning out of corporate life after decades with powerhouse companies like NBCUniversal and iHeartMedia. We dive deep into his first real estate deal (which included a casino win!), building a successful STR business from the ground up, handling nightmare water leaks, navigating complex regulations, launching a co-hosting company, and what it really takes to succeed behind the scenes. This is a candid, practical, and inspiring conversation for anyone who’s thought about using real estate to create freedom and flexibility—especially while still working a full-time job.
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Hello everyone and welcome back to another episode. I am excited to have with me Jason. Welcome to the podcast.
Thanks for having me. That is so much more exuberance than I have on my podcast when we launch the very intro of ours. I’m going to have to take a page out of that. Thank you for the intro. Your setting is great. We were just talking off camera about where you’re recording this from—a house that’s older than the United States. How inspiring is that? Whatever is behind you looks beautiful. I have boring drywall, right?
I’m trying something new. I’m lucky in this one that I’ve got something kind of scenic for recording. I’m not always that fortunate, but it is something I appreciate today. I’m excited for you to share your story because I know like so many listeners that I have, you’ve transitioned from that corporate world. You were with media powerhouses like Comcast, NBC Universal, iHeart Media, and you made that jump to real estate investing. You were able to get that financial freedom to walk away from that W-2, so I’m so excited for you to share that story with us today.
Sure. Thank you for asking. I did work in the media business—I say over 25 years, but it was longer. The grays that are coming in a lot right now show my actual true age, despite the fact that I still feel like I’m a 16-year-old, as I’m sure we all do. I found my way into the media business back in the 90s. I worked on the research side for almost 10 years with companies that eventually became iHeart Media. I transitioned to the digital world shortly after. Then I worked on the sales side—as a sales manager and a sales director for almost 13 years for local media companies here in New England.
Between those two kinds of roles, it was over 20-something years of working around broadcasters, studios, talent, and people behind the scenes. When I got into the business, I only thought it was people on camera and behind a microphone. And here we are behind a microphone again, in a very full-circle moment.
I loved that industry, and I decided there were behind-the-scenes jobs that probably paid much better than some of the on-air jobs—and that’s what I did. That’s how I funded my life for many years and a couple of decades. Eventually my parents stopped asking if I was going to go to med school and stopped worrying about me because they weren’t sending me money. Whatever I was doing seemed to work out fine despite the fact they had no idea what it was. They probably thought I was still a DJ. Probably to this day. Who knows?
When I entered my 40s—which was last decade—I decided I wanted to diversify my investments. Life was not just going to be the one condo we owned in Boston and my 401(k) or whatever investments we had. So we started listening to BiggerPockets over a decade ago. My profile dates back to 2015. We used to listen to the podcast all the time. It was inspiring to hear people’s stories.
I remember the very first couple of months after we bought the place, we knew there was a pipe at risk of freezing. We stupidly told our guests, “Can you leave this faucet on a drip because it might freeze?” Sure enough, they didn’t—and it froze, it burst, and it flooded the whole place. One of many, many issues I’ve had with water over the years. That one wasn’t that difficult to solve though—a lot of towels, drying, some drywall repair—and we got it back up and running.
We made a lot of mistakes. No one was teaching us how to do it. We were doing it on the weekends while we worked full-time jobs. It eventually worked into where we are today.
There’s so much to pull out of that. One of the first things I wanted to talk about was the fact that you said you’ve got that same mortgage. Now, when you first bought the place, how did the numbers look as an investment? Did it look like an amazing knockout deal? Or was it like, “Hey, this is going to be good enough and it’s something we want personally?”
We did want it personally also. We wanted to be able to use the property, which we did a lot those first few years until we eventually bought some other properties. And we still could use it to this day. It’s a great home. I’ve had friends up there. I’ve hosted Thanksgivings. We have great memories. When my daughter walks in the home, she still wants to watch Cocomelon. She remembers watching a lot of Cocomelon back during COVID when we came up to the house and lived there for three years.
I think we just took a leap and a risk with the numbers at the time. We purchased the house for $192,000. We put 20% down. Half of that—or not quite half, maybe a third—I won in a casino, which I’ve talked about on other podcasts. I got super lucky and hit a royal flush on a game called Let It Ride. I bet $15, and Let It Ride allows you to pull back your bets if you don’t like what you see. I was dealt three cards to the royal flush, and the other two community cards turned out to be the rest of the royal flush.
So I won $15,000. It was a thousand to one on each of my $5 bets. I wasn’t betting big—I’m not a high-stakes gambler—but I won $15,000. I would’ve won $400,000 if I’d bet the progressive, but I didn’t. Long story short, I got about $12,500 in cash and said, “I’m going to invest this.” And sure enough, it turned into part of the down payment for the house.
It was almost $700 a month extra plus expenses. I was nervous to tell my parents that we were doing this because they’re very conservative. They said, “Where are you going to get the money for that? How are you going to pay for that along with everything else?” But we made it work. Then we saw the property going up in value. It started making money. And quickly thereafter, we decided, “Let’s just do this again. And again. And again.” You keep finding your way with additional investment properties. It gets very addictive.
Even if you’re not a gambler. What I love—because I just had a conversation this week with someone from the Northeast—is that she wants to do short-term rentals and get the tax benefits. And yet, when you look at those numbers for year one, it can be daunting. It can be scary—especially when someone is like you were when they got started. They don’t know how to do things yet. They have full-time jobs.
So it can feel like, “Okay, this is something I don’t know anything about. I have a full-time job. The numbers don’t look great in year one. Why am I even doing this?” Can you speak to why they are doing it? That long-term vision?
Yeah, it’s really hard to find deals that will cash flow immediately these days, right? Given where interest rates are, where prices are, just the general economy—some people are scaling back. Our places are doing well. We keep going up in terms of revenue because we’re fortunate, we’re good at what we do, and we’ve made good choices.
But for people buying right now, it’s going to be very hard to get first-year numbers that put you in the black. So we always tell people, “Why are you doing this?” Is it a house you want to use? Is it in an appreciating market? Do you think you’ll enjoy it?
There’s value in that—even if it’s not monetary. But don’t just buy something to buy something. You could rent someone else’s place and avoid all the headaches. That said, real estate over time has been a solid investment.
In the Northeast especially, it’s been steady. It’s not like one of those boom-and-bust COVID markets. It’s been a steady increase. I saw a study just yesterday about real estate markets outside Boston. Beverly, Massachusetts was rated the number one community by whatever metric.
We’ve had success in New Hampshire. It’s a multi-season property—summer, fall, winter. Spring is kind of muddy, but everything else people go to New Hampshire for: leaf peeping, lakes, skiing, ocean. We think it’s been a good investment. But people listening from all over need to ask: is there a market near you that people have always gone to? Somewhere you could enjoy with your family, and over time it could pay you back? That was the risk we took—and it seemed to pay off.
Now, one thing you’re making me think of as well—a little bit of a tangent here, but I think it’d be helpful—is how much did you consider regulations? Like, with New Hampshire, did you initially consider how friendly it was for short-term rentals? What does the regulation environment look like where you’re investing? And what do you recommend to other investors in that sense?
New Hampshire is very town-by-town. We operate in Farmington and Guilford, New Hampshire. Farmington has zero regulations at this point. Guilford is regulated, where I have a license issued through the town. It was voted on by the townspeople. I couldn’t vote on it because I don’t live there full-time. So basically, the residents vote on behalf of all of us that are short-term renting our properties.
It’s good to know what the rules are. There’s a little bit of risk in one of our markets where we don’t really know what the rules are—and they could become anything. But so far, so good there.
I have mixed feelings about it, because a lot of other communities in New Hampshire are putting up really restrictive regulations. Some of them have been challenged in courts. I’m not sure the outcome of all those court cases, but this is probably typical of markets all around the country.
We’ll abide by the rules. Our other market is Provincetown, Massachusetts. That’s always been a regulated town. Now the Commonwealth of Massachusetts is also adding things on top of that. So with our new certificates, we have to get inspections by the fire department or a representative from the state. That’s not something we’ve ever had to do in Provincetown until this new cycle.
I had to do it in Guilford too. The fire chief came out and checked everything. I get what they want to do, but they’re not doing this for long-term rentals. That’s frustrating. Someone could rent to anybody for 365 days a year and they’re not checking that the garage door swings closed—like they did at ours.
If people from Guilford are listening to this, I don’t think they really have a plan to uphold the regulations they put in place. They voted on it, but they’re not coming down on people who didn’t get licenses. That part is a little disconcerting.
Yes, if they’re going to have something, it needs to be fairly applied to everyone.
Correct. I don’t think they understood that when this passed. It was just a vote. “Alright, now what do you do?” They couldn’t even get their application ready by the deadline the law enacted. I asked, “Where’s the application?” They said, “It’s not ready yet.” I said, “I’m supposed to have my certificate by now.” Okay—I’ll just wait until you’re ready.
It’s very Wild West. Usually these things get voted on by a board of selectmen or the town, and then suddenly another group has to administer and process it. I’m sure some markets are really buttoned-up, but others are like, “Now what?”
I will say, because I own short-term rentals in Myrtle Beach, it’s such a long-time vacation rental market that they really had everything in place. It was clear, easy to follow. It’s different in the city limits versus the county, but it’s still clear.
I used to live and work in Chattanooga, Tennessee for a long time, and they were changing their regulations. It was more like what you’re speaking about—inspections, railings had to be a certain height, windows had to be a certain distance from the floor. It was really difficult with some of the older houses there.
Even though we think of short-term rentals as an established strategy, in a lot of towns it’s still new—or it’s grown so fast that governments really don’t have it figured out.
They don’t. And everyone has opinions about short-term rentals. You never know if the person inspecting your property also has a baked-in opinion about whether or not this should even be allowed.
Let’s face it, people aren’t coming to inspect your property just to rubber-stamp it and say everything’s great. If you’re going to give someone the authority to do this, they’re going to find stuff—every time.
Right, like a home inspection. They don’t feel like they’re doing their job if they don’t find something.
Exactly. You hire a home inspector to tell you what to watch out for. They’re never just going to say, “Clean bill of health.” That’s not the job they think you hired them for.
What I’d love to hear now, since we have a lot more of your story to go over—you told us about that first short-term rental, and I know you expanded. What about that experience made you think, “I want more”?
At first, we had additional money to invest and we were looking for a second market. I think I bought the land next door to the house I already described first. The land came up for sale—it was like $28,000. It was a wooded lot. I said, “If anyone’s going to buy this land, it’s going to be me. I want to control what happens on this land.”
I think we took out a HELOC on that property, which I still have open to this day. We bought the land and kind of used that HELOC off and on like a piggy bank. Sometimes there’s nothing drawn from it, sometimes there is.
We did that, paid it off. Eventually we built a beautiful house on that land. But before that, we bought a property in Provincetown, Mass.—a second vacation home loan that I was able to get because of the distance from where we lived.
It was a different lender. They said, “You’re welcome to have multiple vacation home loans because you could be in multiple vacation markets.” I had enough for a down payment for that property. We bought that back in 2018. It’s turned into another amazing investment. That market has shot up in the seven years since then.
We worked our way up to the numbers we’re at now, and we operate a business in Provincetown called Pride Away Stays. Pride Away Stays is a co-host for, at this point, almost 25 other properties in that market. We just launched it about a year and a half ago. We didn’t see anyone local doing it well, speaking to the LGBTQ+ community, or having a real foothold in the marketplace. Because we’re also owners in the market, we wanted to build a business that served the market.
We launched it, and it grew pretty quickly. We just had our best month ever. We’re recording this in the summer—the next month should also be our best month ever.
Not without challenges—running any business is going to have challenges. But we bought into that market. We didn’t know about our daughter at the time. We were getting the property ready and then we found out that we were selected for adoption. She came shortly after we bought it. We decided to use the property less and rent it more.
We still go down there fairly regularly, especially with the business now. We just kept wanting to scale up. Then I wanted to build on the land I bought. We had house plans and sat on them for a couple of years. Eventually, we decided to go forward with it. I got a construction loan for that property and closed on it at the absolute lowest interest rate we’ve seen in the past 20 years. That loan is never getting touched—3%.
It was a great loan product from Lighthouse Credit Union (formerly Northeast Credit Union). It was a 30-year amortized loan with a one-year draw period while building the house. The first year was just draws and interest. Then it converted automatically into the remaining 29 years—no second closing. We got lucky—it closed in November 2021, right at the bottom of interest rates.
That property is doing amazingly. We love using it. It sleeps 14 people. It’s a gorgeous new construction home with beautiful triangular windows. We built it with short-term rental in mind. We wanted to maximize bedroom space, finished the basement from the start, added a solo stove, Adirondack chairs, beautiful deck, and lots of games.
My 2,500 CD collection is there from my DJ years in the radio business—it always gets comments. Building it was a great process. We filmed everything from breaking ground to finishing the property.
That also had a flood about a year into it when a guest left the faucet on during a power outage and stopped up the sink. I’ve talked about this on multiple podcasts—that $130,000 insurance claim. But we got through it.
Shout out to Proper Insurance. That property is doing really well. It makes a lot of revenue, we love using it, it looks beautiful, and we learned a lot along the way.
I’d love to dig into that insurance claim because that’s something that terrifies people. What tips would you have for investors who face a big insurance claim situation?
From my perspective, I moved all of my policies to Proper Insurance, which is specifically for short-term rentals. The premiums are higher, but I felt better covered. They covered me. The claim process was relatively simple compared to others. No fighting with adjusters—very straightforward.
We had everything documented, submitted on time, and had the right coverages. They covered up to $50,000 in lost income, which is part of their standard policy—though the limit can vary.
My advice: make sure your insurance company knows what you’re doing if you’re in the short-term rental space. A lot of people think they’re fully covered and then find out they’re not. I wouldn’t go with anyone else. I moved all five of our investment properties to Proper because I think they’re the best.
Also, don’t freak out. We got the phone call at 2:30 in the morning from the fire department. A neighbor thought the house was on fire because of the steam on the windows. It was just hot water from an on-demand system running for five hours and flooding the place.
We didn’t freak out. We drove up to see what happened. It was gut-wrenching—this beautiful new house flooded nine months after finishing. But we moved quickly. Got Serve Pro involved within hours. Opened the insurance claim. Called my builder back.
Always pay your contractors on time—or early. I had a great relationship with my builder. There were 6–7 draws throughout the build. After every one, I got him paid within a day—literally running around to get checks. I was low maintenance, trusted his advice, and was easy to work with.
When I called and said, “Rick, we’ve got an issue at the house. Can you do the rebuild?”—he said yes. He got his crew back on site for the next three months. He got paid again. I don’t think he worked at cost out of pity—he appreciated the additional work. I just treated people really well, and it got done.
I was on site often to document. It wasn’t easy—we had to cancel five sets of guests, and that stunk. But the great thing about Proper Insurance is they paid us for those cancellations, plus for time the property would’ve been booked if not for the damage. I had good records to prove it. They paid us at a certain rate for the lost days.
There’s a lot that goes into it. I don’t wish it on anybody. But I felt I had the right coverage and systems in place.
What I’m hearing is the importance of having the right coverage from the start and handling things right away. When something is nasty or unpleasant, people procrastinate—but that only makes it worse.
You also sowed good seeds—paying contractors quickly, being responsible—and when you needed that reciprocity, it was there.
I couldn’t agree more. I try to get things done quickly. We all have our A-list, B-list, and C-list tasks. I triage: is this urgent? A mechanical issue affecting the guest and the property? That goes right to the top.
Like, I had a guest yesterday let me know the kitchen faucet wasn’t working. Water was spraying under the cabinet. I thought it was strange. Turns out that when I had a dishwasher repaired, the hoses weren’t positioned correctly. That friction frayed the sprayer hose. Water wasn’t making it to the spout. I had to fix that immediately—called an emergency plumber.
I had an HVAC issue a few weeks ago when we were on a trip—I was in Iceland troubleshooting it. I do have a team, but for certain things, especially handyman work, I tend to jump in myself. I had to solve that issue. I got an HVAC company over, and it turned out I hadn’t changed the filter recently enough. The filter was so clogged, it restricted airflow, caused the system to freeze, and then there was no air conditioning.
Lesson learned: change your filters more regularly than you think. But I troubleshot that because I had a house full of people and a heat wave was coming. They needed AC. I had to pay for emergency services, get people over there, and solve it. That’s what you have to do when you’re hosting these properties.
It’s part of that urgent-and-important matrix. Some things are important but not urgent, others are both urgent and important—like HVAC issues or water leaks.
Oh my God, water is the death of me. It’s been a constant issue over the past few years. But when you have more properties—more houses, more guests—the odds of something going wrong increase. That’s just the nature of scale.
But also, the money increases too. That’s the flip side.
More money—but in both directions. As we speak, I’ve got a new hot water heater being installed at one of my properties because I had a problem just the other day. We were on a cruise, and I got a call. I happened to be online when it came in. A guest said the tub wouldn’t stop running—the regulator on the tub wouldn’t shut off, and water wasn’t stopping. He said, “Your tub’s going to overflow.”
It’s a below-grade bathroom, so everything pumps upward. The pump couldn’t keep up, so water was pooling in the tub. What do you do? You shut the water off to the building—even if it irritates the upstairs neighbors. I wasn’t going to flood my place just so they could shower. I had to figure it out.
It required a whole new regulator, emergency service, cutting into drywall, solving it from the backside, and smoothing things over with my upstairs neighbors because I had to cut the water for a couple hours. But life goes on.
We could do a whole episode just on multifamily—sharing walls and water lines. It can be a blessing or cause real trouble. That’s for another time.
Yes, I was very unwilling to flood my unit just to spare some inconvenience upstairs. A couple of hours without water is worth avoiding a disaster.
We’ve talked for a while now and it’s time to wrap up, so we’ll jump into closing questions. First: what is your go-to tool for managing operations?
We use Hospitable for our property management software. I’ve used them for three years. I can’t believe I operated without them. Even when I had just five owned properties—which I once said was all I’d do, and then we launched a co-hosting business. Now when I open Hospitable, it’s just scroll, scroll, scroll with all the properties.
They’ve been a great partner. We’ve spoken with their leadership. We appreciate their product roadmap, everything they’re adding. Not without issues, but they’ve been terrific.
We also use PriceLabs for dynamic pricing. Hospitable has its own dynamic pricing now, but we’ve been with PriceLabs for a couple of years and trust their system. We’ll stick with them for a while longer. Those two tools really help us operate and grow.
I could write sonnets about my love for both those systems. Next question: what advice would you give your younger self when you were starting out?
If we’re talking about real estate investing, I’d say: I should’ve started sooner. My first investment property came when I was 41. I thought I needed to stay on the straight and narrow—work hard, be a reliable employee, eventually retire.
But when my job ended three years ago, it forced me to do this full-time. I was planning on it anyway, but this accelerated the timeline. It was a big blessing in disguise. I’ve been killing it compared to where I was. I’m grateful we were smart about investing when we did.
That said, I don’t think it’s smart to just quit your job cold turkey and jump into this. I’m glad we had a long transition—we were investing for six or seven years before my job ended. So yes: get started sooner. Those early deals might not make tons of money in year one or two, but play the long game. They’ll pan out.
Right—so many people sit on the sidelines waiting for a home run. But if you hit a single, you’re still on base. You’re in the game. It’s better than being on the bench.
And finally: what’s a book or resource—podcast, blog, etc.—that’s been transformational in your investing journey?
Honestly, I haven’t been on the book train lately. I’ve read many financial freedom and mindset books, and they often say the same thing. I don’t have the patience or time right now.
I’ll go back to BiggerPockets. They set us on our current path. I don’t listen to the podcast religiously now, but I know it’s there if I need it. It’s familiar, and I fully trust what they say.
I think Dave Meyer does a fantastic job with his insights. I follow him more on Instagram now than through full podcast episodes. But BiggerPockets is my reliable go-to—something I always know I can return to for inspiration or motivation.
Well, and I think you bring up a good point. There is a lot of real estate investing education happening on Instagram.
Yeah, we’re really amping up our Instagram as well. We’ve had you on our podcast—SmartStay Show—and by the time this airs, your episode will be out too. We’ve recorded about 270 episodes. It used to focus more on real estate law, but we transitioned it about a year ago to focus fully on short-term rentals.
We also have a coaching business—SmartStay Coaching—and we’re working to publish more content on Instagram that’s valuable and helpful for people. We’re leaning into Instagram because there are great creators on there. The challenge is sifting through who’s actually doing the work and who’s just creating a personality.
For us, it’s the opposite. We’re doing the work. We’re just not taking credit for it on Instagram. So it’s a bit begrudging for me to constantly talk about myself online, but apparently that’s how you build an audience—how you get people to trust you and want to work with you. So we’ll be doing more of that.
And that leads perfectly to my final question: if people want to continue the conversation or learn more, what’s the best way for them to reach out?
You can find me at @JasonMuth on Instagram. There’s a link in my bio that will take you everywhere else you need—website, podcast, coaching. If you want to follow SmartStay Show, check it out on Spotify, Apple Podcasts, or YouTube. We also do video versions of each episode.
Perfect. Listeners, you can find that link in the show notes. Thank you so much for this great conversation. And if you loved today’s episode, please subscribe—we drop a new episode every Monday. This way you won’t miss our next amazing guest and their wisdom. Also, leave a review! Tell me what you loved, what helped you, and think about who you know that could benefit from Jason’s story. Send this episode to them right now—and I’ll see you next week.