From Extreme Job Burnout to Breakthrough with 2 Rentals (He Quit His W2)

Ashley:
He survived the 2008 crash, $300,000 underwater. He pulled the air brakes on a fire engine while his engineer went into cardiac arrest at 35 miles an hour. And after two decades of running into burning buildings, PTSD, and 400 hour work months, he walked away from the fire department and bet everything on short-term rentals.

Tony:
Today’s guest, Brian Flint, didn’t just pivot into real estate. He’s actually done it twice, first in 2009 when everyone else was running from the market, and then again recently when he launched two short-term rentals on a co-hosting business from scratch. So if you’ve ever felt stuck in a career that’s breaking you down, this episode is your playbook for building something new.

Ashley:
This is The Real Estate Rookie Podcast. I’m Ashley Kerr.

Tony:
And I’m Tony J. Robinson. And with that, Brian, welcome to the Real Estate Rookie Podcast. Brother excited to have you on.

Brian:
Yeah, thank you very much. I’m excited to be here. Big fans.

Ashley:
Now, Brian, take us back to 2005. You were 30 years old, a fairly new firefighter. You were three properties deep. What did the future look like from where you were standing at this point in time?

Brian:
The future looked phenomenal. I finally landed my dream job and was getting married the same year. And in 2005, I felt like everything was rolling in the right direction. And we had owned three properties at that point. So the sky’s the limit from my eyes. And so we were doing well. We were happy. We were newly married. And then as you guys know, a few years later, things started to decline, everything kind of unfolded. And that was a very challenging time, both to be a firefighter. And once you hit the 2008 crash, everybody knows what happened to property values that lived through that and owned property. So yeah, at that point it was a lot of struggle and we just tried to figure out what our next moves were.

Tony:
It’s interesting how you don’t always know when you’re about to get smacked in the face. And I was just about 30 years old and I lost my job at Tesla, but it was the same thing. My wife and I had literally just gotten married I think six weeks before I got fired. It was the most money I’d ever made in my life. And just everything felt like I was like, “Man, I finally made it. ” And then literally you get smacked in the face and “Hey, Tony, you don’t have a job anymore.” And it kind of forces you to jump into something else, which we’re going to get into your story because it’s an incredible story. But I think first, just in that pre- 2008 financial meltdown, what did your real estate portfolio look like? Because you had purchased several properties between 2005 and before the crash.

Brian:
Yeah. So we had owned a property in Kyle, Texas, and that was our first property that we purchased. And that one, we went to a Marshall Reddick seminar back in the day, which Marshall Reddick is still around, or at least their network is still operating. And we thought, “Hey, a lot of people have done really well in real estate their entire lives, and if you build that portfolio.” So my wife and I, we bought our property, a rental property, before we bought our first condo. After that, that property cash flowed maybe $100 a month. It depends on how many repairs or what you had to put into it. But after that, we bought a condo and we bought it for just under $200,000, which in Camarillo was a pretty good steel. It needed a lot of work. And so we just did the sweat equity and put in the money into that and then decided to rent it out.
And we were breakeven on it. We were underwater a little bit on it, but we knew we wanted a bigger home to raise a family. And so then we bought another property in Camarillo and that was a four bedroom, three bath house that we paid 720, which I went to the fire department and I was on probation and my captain, I talked to him about it. He looked at me like, “You’re crazy for doing this. ” There’s no young guys that are coming in here buying $700,000 homes. Both my wife and I, we worked, she was gainfully employed as well. So I just believed it’s that sky’s the limit mentality. We’re going to do great. And so we had those three properties and we were paying down our mortgage. Everything was going great. We looked at buying more rentals. We didn’t. But yeah, then that kind of leads us into that 2007 scenario.

Ashley:
Yep. Brian, then the market crashes. So what did the math look like after the market crashes on these three properties?

Brian:
Yeah. So I’ll start with Kyle Texans. That one dropped, it roughly went around 10, 15% decline in value, but the big one was our condo. So we bought it for around 200,000, and then it went all the way up to about 440 in the peak. And I consider selling it. I talked to my property manager about it and the renters in there, they wouldn’t let people in or out of it very often. And so we kind of started to drive the price down a little bit, and then it dropped all the way down to about 160,000. So we were underwater on the condo. And then the house we bought, 720, that one dropped in the mid-fives. So now we’re really underwater, $300,000. And at the same time, being at the fire department, it was good because it’s stable job and we still had our jobs, but we couldn’t go out to grocery stores because people would talk to us there and say, “Hey, what am I buying you guys dinner for?
And I lost my … It’s great to have retirement. That must be nice for you guys.” And so we all just kind of shut it in to the fire stations. You had to be courageous or we started bringing our food to work to cook at the fire station. So everything kind of changed. And so we’re underwater $300,000. We’re losing money on our rentals. We’re barely break even in Kyle, Texas. And now we’re sitting on top of these notes that we can’t refinance. And there was a lot of people handing their keys back and they called it jingle mail. But what was interesting is kind of the pivot point for my wife, Jillian and I, was I got in the mailbox Time Magazine. I subscribed to Time Magazine at the time and it said, “On the cover, it’s better to rent than own.” I thought, “Okay, well, let me take a look at this.
” And this is in 2008, beginning in 2009. And I thought, no way. And so my entire career, I always went the opposite direction. When people are running out of buildings, I’m running it. When people are leaving wildland fires, I’m going the other direction. So I thought there’s no possible way. And so I started to really research what housing markets have done over 50 to a hundred years. And that’s when we really pivoted. And I told my wife, “The one way out of this is we’re going to buy our way out. ” And she thought I was nuts, but she believed in me. And so yeah, that was kind of a turning point for us at that time.

Tony:
Brian, I’m curious because for obviously global financial crisis, there were a lot of folks who lost their shirts. What did the plan look like for you guys? So you said you’re going to buy your way out of this, but was there in that moment any sense of like, oh sh*t, what did we get ourselves into? And do we just sell everything? Like you mentioned the jingle mail. Did you have those thoughts also of just trying to just give the keys back and walking away from all of those properties? And if you did have those thoughts, why didn’t you actually act on them?

Brian:
Yeah. There wasn’t a single person that probably went through that timeframe that didn’t think about just mailing their keys back. And then really I did the research to go, “Okay, what does that look like? ” Because I had friends that had done it. I had a lot of people that had started sending those back. And I thought, “Okay, you’re going to damage your credit score. You’re going to go into some type of foreclosure program. You’re not going to be able to purchase for six to seven years.” And I thought on a short sale, I thought, “Well, where am I going to be if I’m almost 40 years old and I have terrible credit and I have no house and what am I going to do at that point? That doesn’t seem like a very good idea.” And then my wife and I kind of went back to our ideals to go, “Hey, what do we believe in?
Who are we as people? ” You really dig into that honesty, integrity, and you really want to kind of … That was a big challenge for everybody at that time. And we really dug into who we were and how we wanted to be in this world. And we thought, you know what, let’s hold. Now the whole, “Hey, I’m going to go out and buy my way out of this thing.” Didn’t pop up right away. But it’s interesting, after that Time Magazine came out, I started to research other areas and we’re not too far from Phoenix. We live in Southern California and properties in Phoenix were going from 300,000 to almost 380,000, and now they’re for sale on foreclosure list for 80 to $110,000. And so I thought, okay, even if we buy at 30 cents on the dollar and then we sell, my formula was buy it at 30 cents on the dollar, sell at 80% value of what the peak was, we’re going to win.
How long is that going to take? And so that was the move that we did. We transitioned over to Phoenix and that was our new strategy. And we just held with it. And we thought, okay, I’m going to work hard. We’re going to continue to invest our money. All of our 457s, 401ks, they were cut in half, just like everybody else. And a lot of people lost everything. But for some of the younger listeners on this, they say, oh, and I hear this like, oh, I should have bought a house when I was in kindergarten in 2010, 11 or 12. Nobody was doing it. Nobody was buying. And so it’s really hard to look at it. Nothing is always going to line up perfectly for you. It’s not like the homes are going to be cheap and the interest rates are going to be 2% and there’s a market crash or the appreciation or any combination.
It’s always, and you guys talk about this regularly, get in where you think it’s going to work best for you. And that’s the path that we did. So I’m happy to kind of go over how that went and then go from there, if that makes sense.

Ashley:
Well, Brian, I’m curious, how many rentals did you actually end up buying in Arizona?

Brian:
Yeah, for Arizona, my goal was 10. And we bought our first one in Surprise Arizona in 2009. I met the nicest property manager. We bought it for right around 115,000 and it was on Madison Elise Drive in Surprise, Arizona. And we literally drove out there and my wife and I, and we had a new baby at the time in the back of the car, six hour drive, drove out there, took a look at it and said, “Okay, I’ve got to paint it. I got to do this. I got to do all these things.” And we did this, or I did the sweat equity. My wife, she went with me.
So we bought that first rental. That one, it cash flowed about 50 to $100 a month, but our big bet was on the appreciation. And then after that, I started … And they were all VA foreclosures and you didn’t have to be a veteran to get these loans. But what the initial one was is 5% down and they would give you 3% back on closing costs. So you’re coming in with 2% down. And so I think I bought the first one for about $7,000. And so I would just work overtime and people thought I was crazy. So I worked on a truck company at the time, and there’s seven of us in the same station and house, and they would walk by and laugh at me like, “What are you doing?” And I’m planning my trips to Arizona and I’m loading up my Toyota Tacoma with painting supplies and ladders and all this stuff.
And they just thought I was nuts, except for one of my good friends, Ben. He goes, “Okay, I want to see where this goes.”

Tony:
Brian, where did it go? Because I mean, man, $7,000 to get into a deal, even if it’s only cashflow and 100 bucks a month, that was an incredible return on $7,000. How many did you end up buying during that brief period as the market started to recover?

Brian:
So I held onto that one, I stabilized it, and then the next six to eight months later, I made offers in Santa Clarita, Bakersfield on these same VA notes, and I was getting beat on every property. So I probably lost out on 30 or 40 properties and even in Arizona. And so I would check my VA foreclosure lists every day I would check it. And so what happened was a couple popped up and I called the realtor and I said, “Hey, I don’t need representation. If you want to get both ends of it, I’ll do that. Just kind of you can represent me as the buyer and you can represent the VA as a seller.” So I bought two within a week at that point. So I got two more and then I came in. That one, I think the loan terms changed a little bit.
It’s been a long time, but I think I had to put between four and 5%

Tony:
Down. Brian, one last follow-up question. You said you checked your VA foreclosure list. Now, was that something that was maybe just unique to that time or is that even today, is there some sort of database that exists of these VA foreclosures that Ricky’s can still go look at?

Brian:
I don’t believe it exists in the same format. At the time, the VA … And they had requirements and conditions of the home. The homes had to be in decent condition, no broken windows, doors had to operate, appliances had to work. So you weren’t going to places that had … And a lot of people, when they would do the jingle mail back in those days, they’d rip out the toilets, they’d take sledgehammers to the kitchen, to the counters, all of that because they were angry. Everybody was angry at the housing market. So these VAs, they held up well. I don’t believe they have it today. You could probably search for a VA foreclosure list and see what you come up with, but it’s not going to be anything like what we found in 2009 and 10.

Ashley:
Over the next several years, you ended up selling these Arizona rentals one by one, and then even selling your condo and eventually your primary residence. So what happens next once you’ve started selling these properties? Did the appreciation actually happen for you that you were hoping for in Arizona?

Brian:
Yeah. In Arizona, the first one that I sold, we made about 100K on it, maybe a little bit more, about 120. And again, I was looking for that 80%, and all of them had peaked at about 300K. So I was looking to sell them at about between 240 and 260. So the first one, I had so many carryover losses from our condo and the loss rent and everything that when I sold them, that triggers those as well. So you do your carryover losses because I didn’t have reps at the time. We were both W2s. And when that happened, I got a nice tax return. The first giant tax return I’d ever gotten, and I remember specifically it was $36,000. And I thought, okay, I’m going to get audited. And you know what? I did. I got audited and we were so clean on our books that we ended up getting another $3,000 back.
There were missed

Ashley:
Items. I owed you.

Brian:
So I went through everything with a fine-toothed comb and said, “Hey, should we go after this? ” And my accountant was like, “Yeah, let’s absolutely go after it. ” And so they ended up cutting me a check for an additional three grand. So yeah, we sold all of our properties in Arizona. We sold one a year and then I think it was like 15, 16, 17. And finally the condo, it never went back to the value that it was at the peak, but we sold it for about 319, and that was about a $30,000 profit. And I just wanted to get out from underneath the negative cash flow of that property as well. But everything in Arizona, we took all the money, we paid down our primary residence, we put some into savings. And then in 2018, my wife was looking for a new property out in Santa Rosa Valley where we live now and we purchased our property and it was a rental in a neighborhood of like 26 properties and we got it for a million bucks.
And so it was the most beat up house in the entire neighborhood, but we took everything we made from the condo, from all of our learning lessons, and then our properties in Arizona and we parlayed it into our dream home and it’s incredible. We love it. So we’re very happy. And good thing we bought in 2018. We timed that one pretty well also.

Ashley:
So Brian, you rebuilt from $300,000 in the hole by going against every piece of conventional wisdom, but just when things were stable, something happened at the job that changed everything and had nothing to do with real estate. This story is next. We’ll be right back after a word from our show sponsor. Okay, so welcome back. Brian had rebuilt his finances and actually in the story, he’s now fire captain. Life is stable on paper, but what happened next is something no spreadsheet can prepare you for. So Brian, you were a captain leading a crew and one day you’re rolling code three and you look over at your engineer behind the wheel of a 50,000 pound fire engine and he’s in full cardiac arrest. Take us into that moment.

Brian:
Yeah, that was February 26th, 2017. So I remember the date, I remember the tie, I remember the call, I remember the street adjust that we were going to and we pulled out of the engine and turned right and I look over and I go, “Hey, Bob, we’re going to 1426 Saranac.” And I looked and I thought, “Bob?” And his name’s Robert, but we have such a good friendship now that I call him Bob. And so yeah, he slumped over the wheel and this guy was 54 at the time, the fittest guy in the department, six foot four, he’s got all his hair, which I’m a little envious of, and great family man. And so he slumped over the wheel and we probably go another 150 yards at 35, 40 miles an hour in this fire engine. And all I can think of was, number one, don’t die on me today, Bob.
And number two, I got to figure out how to get this thing stopped. And so yeah, I unbuckled, climbed over, and there’s an emergency air brake that now we have them installed on the right side, specifically because of this incident for the captain to pull, but we didn’t have it and I didn’t even really go through the process. I just acted. And some of it, I don’t even really remember. But yeah, we pulled that and we missed two cars as we were going code three right through an intersection by inches on both sides, ran around, Brandon and I pulled him out, which 6’4″, 190 pound man is pretty difficult to climb up inside a fire engine and pull him out, but he came out with these, we got him out just in seconds, laid him down and started CPR. And before we left the scene, he had a viable rhythm, which gave me hope.
And so yeah, he went code three to the hospital. I followed up and the battalion chief’s rig, code three. We had another crew from Ventura County that was nearby having breakfast. So they heard my voice on the radio. I’ve had to listen to it. I don’t remember what it was, but I listened to the recording and they could tell that something was seriously wrong. And so they were like two minutes away. So we had help. We had two additional engines to help us within probably three minutes of when we got him out and started CPR.

Tony:
So your engineer survived and walked out of the hospital fully intact, which is a miracle. But honestly, Brian, most people will call that like a career highlight of a lifetime. You saved someone’s life, like one of your close friends, but you also said that it was actually the beginning of the end of your fire career. Why did saving someone’s life break something for you instead of kind of building you up?

Brian:
Yeah, it’s a good question. And one, a lot of people, and I still struggle with even today, all these years later, but what happened was I took an oath to protect my crew and the citizens and the community that I serve, and I felt like I failed, even though everybody else had said, “Oh my gosh, look at what you did.” And it was notorious in our county. And then I ended up flying to San Francisco and won a Medal of Meritorious Award from the governor’s office as well, but it was never really complete. And Robert ended up retiring a year later. He wasn’t coming back to the fire service after that. He had done enough. And so what happens is for, I probably have run 20,000 medical calls and fires and traffic accidents and anything you can imagine I’ve seen. And that is a bucket that continues to fill up.
And I didn’t know that what PTS was or a post-traumatic stress injury, I didn’t even know what it was at the time, but they just told me, “Hey, let’s get back on the horse and put you back on the engine as soon as we can. ” And then six months later, I went and met with a psychologist because I would just have these moments. I’d be standing in a store and I would think everybody around me or somebody’s just going to drop dead and I’m going to have to go to work again. And that’s kind of a psychological break that happens with PTS. And so I went and saw a psychologist with the help of my wife. She said, “You should go get some help and talk to somebody.” And I went through it and he told me, he goes, “Well, number one, you should never work again.
And they told you to get back on the engine in a few days. You needed months or years off.” And I thought, “Well, that’s not me. I’m a fireman. I’m a captain,That’s not who I am.” And so you fight through that. But the good part about it is we had a peer support team with the fire department, and then I spent the next year building it up. And so we built a team and we brought people on because I didn’t want that to happen to anybody else what happened to me. I didn’t have any resources and I had to go out and find them all on my own. So I hired a doctor, psychologist to work with the department. We did peer review meetings. I did battalion level training with peer support. But funny enough, as I was building it, I ended up using more and more of these resources.
And then eventually that was where I say that was the beginning of the end, that I ended up going out. We lost another firefighter medic when I was in Kauai and he was on Maui and he went into cardiac arrest and I was considering going over there and helping him with his wife. That was on his 30-year anniversary. I lost my captain before that time to cancer. And so we had just seen a lot in our small department and I kind of felt like that was my future. It wasn’t going to work out. If you work in the fire service for basically forever, and there’s a few that have divide all the principles, but if you do 30, 40, 50 years, it’s not going to end well. It’s a great job, make no mistake. And I love the service that I provided, but within a few years after Bob’s incident, I needed a transition and I needed to do something else.
And then I did take time off for the PTS, so I took about a year off.

Tony:
Yeah, Brian, I think it’s incredible. And we see the folks in the fire engine and we understand what comes along with their job, I think from the outside looking in. But to your point, you said 20,000 service calls and you’ve seen everything under the sun. I think we as folks who aren’t in the fire department don’t realize the weight that actually comes along with that. And yeah, it just kind of opens my eyes up a little bit more into what that actually looks like. So I appreciate you sharing that with us. But as you have this realization that this, you said it was your dream career, the thing you’ve been building towards, you realize that, hey, maybe there’s a better path for me here. How does that start to bring you back into real estate? Because you basically started from zero. After you sold all of the Arizona properties, you kind of parlayed that into your dream home in Santa Rosa.
How do you get restarted? What’s the next step after you have this realization?

Brian:
Yeah. So I met with psychologists throughout my year when I was off and under the diagnosis, and I continued to get better. And the first six months, I thought there’s no way I’m going back to the fire service. But as I got closer, I thought, okay, I can go back. I want to end on how I want to end my career. And I’ve never heard a psychologist say this, but they actually said, “You’re crazy.” Said, “You’re crazy when you’re going back.” And they go, “Okay, I support you, but if you have any issues, let me know, ” which was great. But with that, we had always loved Mammoth Lakes, California. And we’d been snowboarding up there. We go during President’s Week and we go during Christmas holidays and then the summertimes are really fun. And so we mountain bike up there and we do all these things and I thought, okay, I told my wife, Jill, why don’t we buy a vacation home because there is this bonus depreciation and I still pay attention to real estate through all of this even though we sold.
And I thought, okay, so if we do this, you get bonus appreciation, I have to work a hundred hours into it. We can make it a short-term rental. Can you please, let’s get on board and give, let’s do a little project so I can stay busy with my mind and really envision what my retirement would look like of the hiking, the biking and the snowboarding and all of that. And she was 100% supportive. And so we went up there and started looking at places and we bought in June of 2024. We bought a two bedroom, two bath with underground parking, great little condo, which we have, but we turned that into a short-term rental and that was the next pivot point of where we’re at today.

Tony:
And Brian, I want to get into the short-term rental component of it because I know you’ve gone on to do some additional things there, but we’ve got to take a quick break to hear we’re from today’s show sponsors. And when we’re back, we’re here how this short-term rental transition works out for you. All right, we’re back here with Brian and Brian just walked us through the struggles of the early real estate investing, the triumphs of actually buying the right properties in Arizona and other places and using that to buy his dream home, but then having this realization that maybe his dream job isn’t what he thought it was, and then transitioning into short-term rentals. So Brian, you mentioned the property in Mammoth, which for those who don’t know, is a very big vacation destination here in California, but you said you bought, what year was that in?

Brian:
Oh, we bought in 2024. We closed in June of 2024.

Tony:
Okay. So that is also a time when a lot of people are maybe waiting on the sidelines because rates are kind of going crazy at that point. Prices have somewhat exploded after COVID. Why did you, I guess maybe walk us through why you still pulled the trigger and what those first few months looked like when the property launched?

Brian:
Yeah. So I listened to Dave Meyer on the market and I went against Dave Meyer and he still has proven to be right.

Ashley:
We’re going to tell him.

Brian:
He’s going to hear this or don’t tell him or tell him. It doesn’t matter. Smart guy, but I thought, okay, I would expect that the interest rates probably would’ve come down quite a bit in 2025 or started to come down a little bit, which they didn’t at all. And so what happened is we got out there, our first weekend was July 4th and we cleaned it up, listened on Airbnb, and then I went to a market to get something in the morning at like 7:30 in the morning. And then I came home and my wife told me, “Hey, good news and bad news. Good news? We’re rented for July 4th. Bad news is we have to leave tomorrow.” And I thought, okay, so we’re in. We’re in the Airbnb game. And so that was ultimately why we bought and why we were up there was that lifestyle, the bonus appreciation.
And I thought, okay, let’s do this so I have a project that we can work on. But yes, everybody was sitting on the sidelines at that time. And so from that point moving forward, I became a little bit more involved with the fire department. I wasn’t giving it the true love that we needed to make it a really good short-term rental. The bonus depreciation worked out phenomenally well. We ended up getting a tax check back for about 60 grand at that time, which is great. And that was with 60% bonus appreciation. So again, with the cost egg and doing that, it’s like, okay, so we can carry this, but we were losing money every month and we knew that, but we were using the property as well. And so Jill, bless her, she got into the operations of running the short-term rental while I was back at the fire department and she was doing a good job.
But what I found was guest communication, five star reviews, dynamic pricing, all of this really matters and it’s everything to make a short-term rental operate and operate well. And so we did pretty good. We did about 7K a month through December, January, February, even though it was a pretty poor winter, we were at about 280 inches of Snow, and the years before the operators, they did about 60 to 70K and they had 700 and 800 inches of snow. So now we’ve got everything’s bending against us, right? The interest rates and we’re in an eight and a half.

Tony:
Even the weather’s going against you right

Brian:
Now. Now I’m going, okay. But I believe, because back in 2009 and 10, I did everything opposite. Well, I wouldn’t say it’s working out great now, but we still bought, we had an eight and a half note on it. We put 10% down, but we did the bonus appreciation. We made that all work. We were bringing in about 7K a month during the peaks. And then when I started to retire, I had a couple more injuries happen and I thought, okay. And that was in May of last year. And we only brought in about $600 for that month. Now that’s a shoulder season, but we didn’t put a whole lot of effort into it. We were more focused on our lives and what we’re doing. And then the minute I retired, I went all in on optimization and then I ended up hiring a revenue manager because that was the only thing my wife and I fight about is if it’s vacant, do we drop the price?
How far out do we start moving the price around? So now it’s optimized and I can tell you it’s a pretty different story. Now we’re at 72 reviews. We have a 4.93. We did have a couple hiccups on cleaning about a year ago. And so now we follow the process of deep clean. But Tony, I do want to give you a shout out. I joined the AlphaHost group to go, how do I do this? How do I get coaching to make it right? And in the fire service, I always coached people to successfully complete their captain’s exam and their simulators. And I thought, well, if those people are out there, let me find a coach that I can work with. And your program was phenomenal. And so we did that. And then I’ll share with you guys some numbers if you’re ready for where we’re at now today.

Ashley:
Yeah, I would love to hear.

Brian:
Okay. So now that we’re optimized from December 2025 to March of 2026, those are our highest months. We brought in about 45,000. So we do 11-3 per month. Before that, we did 28.7 at 7,100 a month. So we did about a 57% increase in where we’re at today. Now, as we’re recording this, it’s 90 degrees in Santa Rosa Valley, as you know, in Southern California. So the snow is melting, but we did months in last summer where we did six and $7,000 a month because it is still a good time of year to go. And then working with our revenue manager, one trick we did was we extended our length of stay. So as you know, the gross revenue might be 11 or 12,000 a month, but you might pay the cleaner 10 or 12 times. Whereas now we focus on four, five, and six day stays.
So we pay the cleaner four times. So your gross is much better or your net is much better. And then the hard part about Mammoth, and I’ll tell you, if anybody’s thinking about buying for cashflow in Mammoth, I can tell you there are better places to do it. Don’t do it. You will not cashflow unless you bring in 30 or 40% and put it down and then you use it as tax strategy and appreciation. But we’re in it for the appreciation plan long term. And then the use-

Ashley:
And the tax benefits, don’t forget.

Brian:
And the tax benefits, they were huge. So that kind of really got us off the ground. And then we believed in what we can do and what we have accomplished. So even though we’re barely breakeven, we’re still for a two bedroom, two bath and Mammoth, we’re one of the highest producing in our area, obviously in our little market area there. We’ll do 80 to 90,000 in our trailing 12 months once we get through the end of next year, for sure. That’s kind of our projection. Right now, including that really bad May that we had last year where we put everything kind of stagnant, we’re at about 74,000 in gross revenue.

Ashley:
And do you get to use the property at all for yourself, for your family?

Brian:
Yeah. We went up there-

Ashley:
Another benefit.

Brian:
Yeah, another huge benefit. We went up there for Presidents Week, and even though those are six and $700 a night properties, I wanted to stay in ours. And so-

Ashley:
And you’d be paying to stay somewhere else if you’d be paying that to stay somewhere else. And it’s nice to be in your own property. Oh,

Brian:
I was just going to say, and then you got to factor in that Airbnb takes 15 and a half, and then the town of Mammoth is 16%. So you only get less than 70 cents on the dollar. So yeah, it makes it a little bit challenging. And so we just go, “Well, why go rent somewhere? Let’s go stay at our place. It’s

Ashley:
Fine.” You think first of like, “Oh, I don’t want to lose out on that income.” But if you think about what you would be spending to actually stay somewhere else, you’re way better off staying at your own place. But after that, Brian, you went on to Blue Ridge, Georgia, so across the country. So tell us about this property. And this was your second short-term rental, I believe?

Brian:
Correct. Yes. So because we were losing money initially in Mammoth and now we’re getting closer to breakeven, I still believe in short-term rentals, but we couldn’t buy another one. And I needed one that was proof of concept that could produce a financial gain. And so I started looking all around the country and trying to figure out where we want to go. And what I figured out was you want to be two hours from a metro and then you want to work backwards, reverse engineer your pricing. So I had about $160,000 that I wanted to invest and I wanted to put down 20% this time because last time we’re in 10%, there’s not as many options for refinancing out. And so I wanted 20%. We got a great rate. We ended up in Blue Ridge, Georgia. We looked at Poconos, Pennsylvania, Virginia. We looked at a lot of different places, and Blue Ridge kept coming up over and over again for a few different reasons.
So I figured with 20% down, I want to put 80,000 in and I want to keep my 80,000 for design, amenities, contracting costs, holding costs, and the cost that it takes to get these things launched. Because on day one, you’re not making a lot of money. You got to get your reviews up. And so we’re still following that formula. And all in on Georgia, we’re at about 120K. But yeah, we bought that and closed in November of just 2025. And then I’m happy to share that story with you too a little bit on that. That was kind of a wild ride.

Tony:
Yeah, please give us the story.

Brian:
So I hired contractors to paint it, sand the floors, stain the floors, and do all the painting. And I hired a design company as well to design it for me. So first off, the designer said, “Hey, it’s really expensive for us to hold it and then bring it to you. ” So another one of my good friends, Brian, lives in Tennessee, so I shipped everything to his house in Tennessee. And so remember, you guys say it all the time, but find out what your superpower is, find out your network. And so I called him out of the blue and we’ve been friends for 20 years in fire service. He goes, “Yeah, I got a full garage, man. I’ll just keep it all in there.” I go, “No, you’re sure about couches and patio furniture and everything.” And he goes, “Yeah.” So then I hired contractors, but I wasn’t hearing back on what they were doing and I wasn’t really getting the proof that the work was being done, but we flew out there and I flew up with my good friend, Ryan, who wanted to help me and see this project come to fruition.
So we flew to Tennessee, loaded up a U-Haul, drug a trailer all the way to Blue Ridge, Georgia, 10 o’clock at night, drove up these mountain roads at one o’clock in the morning and then walked into our place. And it was, I say maybe 30% of the work was done, kind of what I thought.

Ashley:
And how much were you expecting at that point to be done?

Brian:
100%.

Ashley:
Oh my God, wow.

Brian:
I wanted 100% done. And we walked in and thought, “Okay, well, let’s get out of here, go get a hotel room. Clearly we’re not staying here.” And so the next day I went back and they were there, but they’re just like, “Ah, the sanding’s taking too long. This isn’t getting done. We’ll come back with two crews tomorrow.” So I focus on the outside and we started building furniture and putting that all together. And then the next day, nobody showed up. And I thought, what happened to two crews? I thought, oh man, we’re going to get a team of dudes here. Let’s get 14 guys in here working on this place. Nobody showed up. And so I thought, I called the contractor who initially hired him who did do a good job, but he said, “I have to farm this out because I just can’t do it.
” And he came over and thought, oh my God. And he brought his brother, he’s a big guy and he brought his brother because he thought maybe I was going to be so angry that-

Ashley:
He had to bring him up.

Brian:
I’m not a very big guy, but what happened was I called my contractor and said, “Hey, I’m going to fire these guys.” I called the painters and I fired them, said, “Don’t come back. It’s fine. We’ll figure out. ” And he goes, “Well, I want my money.” And I go, “Well, okay, we’ll figure something out. ” I drove to Home Depot at three o’clock that day, got all the painting supplies, finished the sanding, the stain, all of that. And we worked probably 20 hours a day for the next three days to get it all done. And then when my contractor, Gerardo, he showed up, he couldn’t believe it because I was in such good mood because we were making progress again. And he brought his big brother to make sure nothing went down. But he’s like, “I can’t believe that this is where you’re at.” But I go, “Hey, it’s got to get done.
I do not quit.” And so he said, “I’ll tell you what, I’ll give you my electrician and then I’m going to give you four guys tomorrow night from 5:00 to 10:00 PM, have him do anything he wanted.” And I had him hang TVs, hang drape broads and do some heavy lifting stuff. And he said, “That’s on me. ” And then I ended up paying off the painters for their supplies. And I called my wife on day five and said, almost, “I just don’t think this is … I’m not going to get across the goal line on this. ” And I said, “Hey, I got to stay for at least three more days. I’m going to be home Christmas Eve morning now because to get your depreciation and do your cost saying-

Tony:
You got to get it up and running.

Brian:
Got to get it up and running.” And she said, “Well, I’ll drop everything and fly out there.” And I go, “No, you don’t want to do that. Take care of the kids. We got it. ” And on the 23rd at 11:00 AM, we had finished building the first room and I thought, oh my God, it almost brought me to tears how beautiful it was. And my friend Ryan, Ryan, he’s so good with staging and filming and a creative mind that he went and staged the whole room while I was in another one working and he goes, “Hey, Flint, come here and check this out. ” And I walk in there and that’s when it almost brought me to tears. I was like, “Hey, number one, we’re going to finish this. We’re going to do this. Number two, we got a flight tomorrow. We got to leave at 5:30 in the morning.
So we’re working all night long.” And I go, “Well, let me take some pictures, send it back to my wife, Jill, and we get up on Airbnb.” So she’s at home doing all the logistics. I was going to get a photographer and she couldn’t find one and we couldn’t find one on such short notice. So I bought a $20 tripod on Amazon and then I started filming the bathroom or taking pictures. I thought, let’s start with something easy that let’s start with this. And I could feel Ryan over my shoulder and he’s leaning in and he’s like, “You kind of have the door in here in the picture.” Let me move it this way.

Tony:
Well, man, good thing you brought Ryan with you because it seemed like he had the creative vision to bring the space to life.

Brian:
Oh my gosh, Tony, you have no idea. And I’m more of a who, not how type of guy. And he said a couple other things. It’s like, “Well, get the toilet paper out of the roll. Let me move this. Let me roll these towels up.” And I look back and I go, “Do you just want to do this? ” He goes, “Are you serious?” I go, “Yeah, you can have it, man.” I’m like, “Clearly you’re better at this than I am.” And he started taking photos and I couldn’t believe what he was able to pull off. But I would get back on him like, “Hey, but you got to stage this room now.” And he would take 30 or 40 photos of the bathroom. It’s like, “Let’s get out of the bathroom.”

Ashley:
So did you end up making the deadline then? Did you have it listed in time before the end of the year?

Brian:
Yes, we did. We finally got everything up. We finished filming and shooting the place in the dark at two o’clock in the morning. I finished up a few more projects. We worked till about 3:30 that morning and then drove to Atlanta at 5:30 on the 24th to fly out. And we already had it booked by the time I landed December 26th through January 4th.

Ashley:
Wow. Oh my gosh. By the time we landed, wow.

Brian:
We made it. Yeah. And that’s also helped to my wife who I would just send her a bunch of photos like, okay. And I had this Shell Airbnb built before we went out there. And so had we not done that, it would’ve just been more work. And then I came home, fine-tuned it, and that one is doing, it’s doing really well now. That one is where I believe all I ever wanted to make on it was $1,000 a month, 800 to $1,000 a month. And I think we’re going to get there. We just added a brand new spa, so it took eight guys to get it around the house and then lift it up. And so there’s kind of those unforeseen costs, right? I had to pay them another 1,700 just to get it up around, installed and set, and then shoring up the deck from underneath.
But yeah, I’m happy to run through those numbers. Those are pretty interesting too, if you guys are ready. Okay. So we put down 80 grand. We put about 20,000 of furnishing, the hot tub, 6,500, 10K in repairs. I’m going to paint the exterior and we’re going to do it like a black exterior and then kind of a wood trim deck on it. So we’re at about 120K. That one, our totally monthly cost is 3,700 for pest control, internet, electric, propane, trash, water, all of that. And then our scenarios look pretty good because our purchase price was 409. We got a 6.375 note on it. If we do 65K in revenue, we’ll cash flow about 5,000, but that doesn’t include any CapEx, 5,000 for the year. If we do 75K, we’ll cash flow. There’s my magic number. There it is, that thousand dollars a month. And I think we can get there.
With all the sweat equity, I’ve talked to a realtor and we’re probably up about 50 to 75K in appreciation already, which is great. But with the bonus depreciation, here’s where it gets really interesting again, I just did my cost seg and finished it and we did 105 back in depreciation costs on that 100%. It’s

Tony:
Like almost everything you put into the deal, Brian, you just got back.

Brian:
Yeah. Yeah.

Tony:
It’s like free money. And guys, that’s what a lot of people don’t understand about tax strategy. I see so many things online where people talk about tax strategies that aren’t real tax strategies that might get you, like you’re just begging to get audited by the IRS. People turn in every vacation into a business trip or they’re writing off their Gucci suits because they have their logo on it. And those sound cool for social media, but what Brian’s talking about here is an actual tax strategy supported by the IRS tax code. And I mean, you got back almost every single dollar you put into this deal, which it allows you to keep recycling the same process, produce more cash flow, get more appreciation, and the cycle just compounds. So man, I love a happy ending to a story.

Brian:
Yes, we’re there. I feel pretty good about it. The cap rates look good. I love the property. People love the property. We’re at 10 five-star reviews already on it. And that’s what it is, is that guest communication, you’ve got to stay on it. And people talk about the Airbnb bust, which is if you’re not actively in it. It’s a full-time job to run these Airbnbs, as you guys know.

Ashley:
Well, Brian, you actually are doing co-hosting now for other people, correct? I think this is such a great way for people to enter real estate without having to actually purchase real estate is by doing a co-hosting business.

Brian:
Yeah, absolutely. Thank you. As much effort as we put into it, and then I just happened to be, when I flew home from Georgia, I was on the sidelines of a soccer game and our good friend Robin was standing there and we started talking about properties and she’s like, “Your face just lights up when you talk about this stuff.” We have a place in Park City that we’ve been talking about getting on Airbnb for eight years now. And I thought, “I can do that. I’ll help you. ” I love it. I love going out there and putting these places together. So we were able to launch that one and they’re very happy. And then I co-host for them and then I’m bringing on another one in Mammoth. And then I’m focused specifically in Mammoth, but there’s as of right now, but I’m looking to branch out back into Park City and even Blue Ridge.
But I know the Mammoth market better than all of these other ones. So yeah, that’s what I’m doing full-time now, which is hosting.

Ashley:
Well, Brian, thank you so much for joining us today. Can you tell us where people can reach out to you and find out more information about what you are doing?

Brian:
Yeah, absolutely. So the easiest way, the one I track the most is just [email protected], B-R-I-A-N, and then Highline, H-I-G-H, linehosting.net. Have a website that we built through the company. It’s highlinehosting.net, and then I’m on Instagram kind of @flintighline, Facebook, Highline hosting. And then realistically, the easiest way is just to text me. So if people are needing help with their properties or they want to have us manage them as an owner, 805-797-1374, and I’m happy to help.

Ashley:
Well, Brian, we appreciate you taking the time to share your story with us and the lessons you have learned and also your success as a real estate investor. So thank you so much for taking the time to share with us and the rookie listeners. I’m Ashley. He’s Tony, and thank you for listening to this episode of Real Estate Ricky. We’ll see you guys next time.