In short
Ashley and Tony discuss Tony’s real estate portfolio update and “big changes” to his short-term rental strategy, focusing on scaling from 26 single-family Airbnbs into a 13-room boutique hotel, plus lessons on market selection, deal analysis, and execution.
Guests
Ashley Kerr (host, Real Estate Rookie Podcast). Tony J. Robinson (guest; full-time short-term rental investor/operator; runs education company Alpha Host Academy; builds apps/tools for Airbnb analysis).
Key claims
The hotel validated the “proof of concept” that Airbnb ops translate to a smaller hotel; scaling too big too early increases stress. For new investors, start smaller, then repeat. Market selection should prioritize data (listing growth, demand growth, occupancy, ADR, RevPAR, competition), not just where you like to vacation.
Notable examples
Hotel in California/Tennessee/Utah; bought for $950K; 2025 first full calendar year; labor/turnover is the biggest struggle due to a smaller town with a 45-minute nearest population center. Example underwriting process: Indianapolis—design upgrades, proximity to Speedway/Cambridge Fieldhouse, and flat backyard amenitization.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOPortfolio Overview
0:45 to 2:42
Tony shares the current state of his real estate portfolio, including holdings and markets.
“We've sold off a couple over the last couple of years.”
Insights from Hotel Operations
2:42 to 6:06
Discussion on the operation of the hotel and lessons learned in management and customer service.
“And obviously just like, hey, is this something that we want to continue to do?”
Challenges in Labor and Management
6:06 to 8:52
Tony talks about challenges faced with labor turnover and the difficulty in finding reliable staff.
“And we've been making steady strides toward that figure.”
Future Acquisition Strategy
8:52 to 11:34
Exploration of what Tony is looking for in future hotel acquisitions and the importance of market size.
“But, you know, hey, math did math for her.”
Lessons from Ownership and Decision Making
11:34 to 14:00
Discussion on the lessons learned from managing the hotel and the importance of starting small in investments.
“I mean, I think honestly, Ash, that goes back to the whole reason why our buy box was the way that it was.”
Starting Small in Real Estate Investing
14:00 to 14:54
Learn how to approach real estate investment with a smaller, more manageable strategy.
“Even if you are doing everything correctly, there's so much stuff that comes up that you don't even expect to have.”
Teaching Unique Short-Term Rental Strategies
17:50 to 21:00
Toni discusses innovative market selection and analysis for short-term rentals.
“What is the one thing that you are teaching people right now about short-term rentals that maybe other people in the same realm are not teaching?”
Improving the Buy Box Research Process
21:00 to 25:01
Toni details the importance of market analysis before property selection.
“Now, what about what system or process are you building right now?”
A Day in the Life of a Full-Time Investor
25:01 to 28:00
Toni shares insights into his daily life as a real estate investor and family man.
“It's crazy how like probably three, four years ago, like we interviewed Ariel and she was talking about how she was scrubbing data and doing all these things.”
Balancing Work and Family Life
28:00 to 29:22
Learn how to achieve flexibility in your work schedule and prioritize family time.
“was able to take him you know pick him up after school and took him to that and you know that's what we did.”
Show all 16 chapters
Partnership Dynamics in Real Estate
29:22 to 31:32
Explore how to manage personal and professional relationships in a business partnership.
“So I think that's one of the really great things.”
Effective Termination Practices
31:32 to 35:17
Understand the importance of clear communication and documentation when terminating employees.
“And I'm like, oh, my God, he's not going to say anything.”
Effective Termination Practices
35:59 to 37:07
Understand the importance of clear communication and documentation when terminating employees.
“realizing that scaling rentals shouldn't mean creating more work for yourself.”
Content Consumption for Real Estate Investors
37:07 to 37:50
Discover the best strategies for consuming real estate content effectively.
“plus of the equity in each investment right alongside accredited investors.”
Content Consumption for Real Estate Investors
37:53 to 42:00
Discover the best strategies for consuming real estate content effectively.
“Maybe you bought a few rentals 20 years ago.”
Identifying Your Short-Term Rental Motivation
42:00 to 43:51
Learn how to determine the right motivations for investing in short-term rentals.
“there because or else I'm going to have FOMO that I'm going to miss out on learning some strategy and making some connection with really no plan in place as to how this is going to actually make me a better investor.”
Transcript
Automatic transcript. May contain errors.0:00Tony:This is the Real Estate Rookie Podcast. I'm Ashley Kerr. And I'm Tony J. Robinson.
0:09Tony:Well, Tony, today I want to do something a little different. You and I talk every week, but I feel like I haven't gotten a proper update from what you are doing recently in your real estate investing journey. And every time I hear you talk about your portfolio, your real estate investing journey, I always learn something. So today I want to get an update and see how things are going. Let's get into it, Ash. We'll give the update for the people. Okay. So the first thing is kind of give us the current snapshot of where your portfolio is today. What holdings do you still have? What type of property are they?
0:44Yeah. So we're at 26 single family Airbnbs. We've sold off a couple over the last couple of years. And we have our 13 room hotel. We're in three different markets across the United States. So California, Tennessee, and Utah. So that's the support folio today. And then we've also got some flip inventory that has been the bane of my existence, but maybe we'll talk about that later.
1:09Tony:Okay. So first let's talk about the hotel. So you've had one full year of operation, correct? It's been like a year and a half, but one full calendar year? Yeah. 2025 was our first full calendar year. So So 2026 will be our second four year. Has the hotel been what you expected? In a lot of ways, yeah. I think for us, the thought process, well, first, let me back up. The thought process for us going into the hotel was in order for us to scale our portfolio, we could continue to buy single family homes as Airbnbs, or we could, like many investors do, we could graduate up to larger properties. And the hypothesis that we were trying to test is how much of our single family short-term rental operations and underwriting and just like everything that we've learned, how much of that will translate into a small kind of midsize, not even midsize, a smaller boutique hotel.
2:04And that's what we were trying to test. Like, hey, everything that we've learned, will it translate? And I think the answer was a pretty strong yes. a lot of how we run our operations. If anything, I think we maybe even had a better system than some of the hotel operators that I found because reviews are so important in Airbnbs that we do things maybe other hotel operators don't do. We get photos of every single turn and we can look back at certain things. So a lot of the foundational things we set up on the single family side translated incredibly well into the hotel. So that was the goal. So I think we checked that box.
2:43And obviously just like, hey, is this something that we want to continue to do? And I've joked about this before, but the hotel is 13 rooms and managing those 13 rooms in that hotel is significantly easier than managing 13 separate single Airbnbs. So there's definitely some pros to making that jump.
3:01Tony:What do you think has been the biggest struggle? Hands down, it's been labor. We bought in a smaller market and that's probably something that we won't do moving forward. I think the next hotel that we purchase will need a larger population center to kind of support running the hotel. But we've just had a tremendous amount of turnover. And it's not unique to us. It's just something that the entire city kind of struggles with. Like the nearest population center is about 45 minutes away. So the town really just does kind of sit by itself and kind of like a little island. And, you know, there's not a large permanent resident population.
3:44So just finding the right people to do things like clean the pool, you know, you know, landscapers and trades folks and all those things. So we got a really, really good price on it. But part of the reason that we did is because it wasn't a smaller city.
3:58Tony:I think this would make like a great HGTV, you know, series as to like you and Sarah pack up the kids and you move out to Utah and you manage this hotel for your by yourself for like six months or whatever. And there you are out, you know, do the pool and you know, the kids are running around and welcoming guests. That TV show does exist. It's called Motel Makeover. And yeah, Sarah and I tried to pitch ourselves for that actually. So you know, if you got the connection as let me know. Okay, but what about what's next for acquisition? So are you actively searching for a deal and what is your buy box?
4:35Tony:What are you looking for? Yeah, we definitely want to take down another hotel. My partner who I worked with on that deal, his name's Xavier. He honestly did a lot of the heavy lifting in terms of finding the property and kind of doing a lot of negotiations. And then we kind of worked together on the underwriting. And then me and Sarah really took over once we closed. And he welcomed his first baby last year. So all of his real estate activity kind of slowed down. He still has a full-time job that he works as well. So for him, after he welcomed his daughter, he was like, hey, I've got to hit pause for a little bit.
5:07But luckily, we just caught up maybe, I don't know, three weeks ago. And his daughter's a little over a year now. He's like, hey, man, I'm ready to jump back in. So hopefully, we can start putting some rubber to road on finding that next deal. But yeah, the buy box for us on the first deal was we wanted 10 to 30 rooms, a purchase price of about$1 million to$3 million. And we wanted a strong value-add opportunity. And we were really avoiding cities that were maybe too rural. And we were more so focused on vacation markets. For the next deal, definitely something that's bigger. Actually, I won't necessarily say bigger, but something that'll generate more revenue.
5:49When we bought this hotel, again, we bought it for$950K. So it was just under a million bucks. When we bought the property, I think that last year, the previous owners did like, I don't know, I think like 250 in revenue somewhere in that ballpark. Our projections at SETI State will have a student about a little over 400K as we're projecting. And we've been making steady strides toward that figure. So I'm somewhat confident that we'll get there. But I think for the next deal, it'd be nice to be able to have something that does like 3X that. The room count isn't as important, but if we can get a hotel that's doing over a million on an annual basis, that gives us a lot more room in the budget to A, hire a really strong general manager because Sarah, my wife, and I are still effectively the general managers for this property.
6:35So I think just a little bit more revenue, we can get the right staffing in place to handle a lot of day-to-day. And then again, hopefully buy in a market where there's just a little bit more people living there to support it.
6:48Tony:I'm in the trenches with you, Tony. I'm the manager of my liquor store now and you think it's going to be like, oh, okay, I can run payroll. I can do this. But like, it's all the little things that come up that like interrupt your day that are for real, like, and having to make quick decisions. Like it's more than you think. Yeah. We actually just had someone quit yesterday. And, you know, Sarah, my wife, she handles most of that, but, you know, she's like, you know, just recently graduated from high school, I think like two or three years ago. So, you know, she's newer into the world of, of, I think working.
7:21And, um, we, again, turnover, she's been with us now almost longer than anyone else. Um, it's been, I think a little over a year for her. And, uh, we, we, we had some new folks that were training and she was like, Hey, I'm fine to train people, but I need, I need a raise of like$2 per hour. And, you know, we're like, Hmm, you know, we don't know how we feel about that just because the way that she kind of presented it was kind of like an ultimatum, like, Hey, I'm not going to train these people if you don't give me this raise. But again, limited on labor. So we're like, hey, she's been with us for a while.
7:49She does a decent job. Let's give her that. And then we reopened the pool. We closed the pool down during the winter months. And now the sun's out, we reopen the pool. And we update all the cleaners to say, hey, now the pool's opened again, just like it was before, part of your task are to make sure that you're checking the pool and doing all these things. And very small things like, hey, if there's leaves, can you grab the skimmer and And skim, wipe down the pool furniture that's outside. Super minor things. And then she came back to us again and said, I'm happy to do that, but I need another raise.
8:19And that was kind of like the line in the sand for us. And we were like, hey, this isn't going to work. If we can't have someone who's a team player, then this just isn't the right team for you. So we had a mutual parting of ways yesterday. But that is a challenge, right? Is just finding good people in that market.
8:34Tony:And this was somebody that was hourly? Yeah, hourly. The whole team's hourly. It's not like you're paying them salary and then saying, here's a ton more stuff you have to do, which in some cases you should be a team player to take on those things. But this is like you're going to get paid more because you're going to be working more to do that. 100%. Yeah. But, you know, hey, math did math for her. So wish her all the best. But that is the challenges that we face managing it ourselves. Let me ask you this because this is something that I realized. So on this deal, you decided not to do a syndication and you didn't raise money.
9:12Tony:You did seller financing on this. You have one partner on this? There's four of us in total. Okay. But you guys are all active partners of this or whatever, okay? With my liquor store, I have one partner on it. And me as the new manager, we had a situation where somebody needed off. And we only have two employees right now. One works all during the week and then one person works Saturdays. And originally they were supposed to switch days or something. Then last minute, they couldn't. So I had somebody else, a friend that filled in once before for somebody and like kind of knew how to work the cash register.
9:51Tony:I said, I need another big favor. I pay him. I'm like, I just need you to go ahead and, you know, can you work this day? And he was like, no problem. him. And then he was like, only I could do half day. So then my brother, who's never ever worked there in his life, he's like, I can work the second shift. I'm like, thank you so much. I'm in Florida. I go and look at the security cameras. We're supposed to open 11. I look at 1230. The lights are off and no one is there. My poor friend forgot, forgot to go there. And I was like, I wanted to be mad, but I really, really wasn't mad. This was my own fault.
10:28Tony:This was my own fault for asking for a favor from somebody who isn't employed there, who's not an employee. I should have a backup person that is available to cover shifts. And I decided, you know what, I'm just going to close the store down. It's going to hurt me. My partner is okay with it because he knows I'm doing whatever to try to make this thing profitable again. But that was like a big realization is if I had investors that were, you know, getting a profit share, getting a return on this, and I did not open on a Friday, which is the busiest day, I would be hurting them. Where this was my decision and was like, okay, I'm hurting me.
11:10Tony:And I'm making that decision to do that. And I think that was definitely a lot easier to do. And but also a big realization. So I'm just curious, do you ever find that with the motel where maybe you're making certain decisions knowing that it's going to affect you instead of if you had a syndication and you had a whole bunch of investors that are looking to you? Yeah. I mean, I think honestly, Ash, that goes back to the whole reason why our buy box was the way that it was. I didn't want to go so big on that first deal because I really wanted proof of concept. And way, way, way back when, like if we rewind to, I don't know, I think this was like 2021, when I first had the idea of buying a hotel, I did try and go bigger.
11:59And it was like a$5 million raise. I can't remember what the purchase price was at this time. Was this one in Big Bear? It was the one in Big Bear, yeah. And there was like 30 different cabins and the revenue was significantly bigger. It was just a much bigger operation. Now, granted, I think we could have done well with that. But as we struggled through that deal and then we started to kind of revise what our buy box looked like, I really came to the conclusion that the purpose – and I say this all the time on the podcast, right? But the purpose of this first hotel deal isn't necessarily to maximize cash flow.
12:31It isn't necessarily even to get the greatest returns. The goal was just proof of concept. Like, hey, does this thing actually work? And can we take what we learned? And I was super transparent with our partners when we did that, when we brought them into the deal. So me and Xavier as the operators, and we had two capital partners. It's like, hey, guys, I've never done this before. you know it's like i have no idea if this is actually going to work out and if you're not comfortable with that then i totally understand like hey this deal isn't for you but they were both like hey yeah i just want to also get some experience in this space and see how it works and let's let's see what happens right so i think the fact that i really framed it correctly at the beginning um has allowed me to to kind of have some uh not i wouldn't say flexibility but just i'm not as stressed about making decisions because we all went into it with the right with the right mindset.
13:21Tony:I think that's a great way to put it. My situation is a little different where in New York State, you can only own one liquor store. And so I probably will never go and raise money to buy another one. But I think you put that very well. And I think that's a lesson to rookie investors that if you want to go and do something that is new to you, start smaller because you most likely will make mistakes or there will be decisions that are hard to make. And maybe you're not ready to make those hard decisions or don't have the time to take the action or whatever it may be, instead of going and raising money on your first deal and making all these promises that you know you can do it, and then you don't even have room for the hiccups and the roadblocks.
14:03Tony:Even if you are doing everything correctly, there's so much stuff that comes up that you don't even expect to have. Couldn't have anticipated. Yeah. And Ashley, I tell people all the time, when I coach them through our program, it's like, even if someone has, say you're pre-approved for million bucks and you've got, you know, 300K liquid that you want to go deploy. Oftentimes cell folks, it's like, why don't you cut that in half? You know, instead of buying a house, it's a million dollars and investing 300K, go buy a house that's half a million and invest 150K instead. And if you can prove concept with that, well, then you can go do it again and make the next one a little bit bigger and a little bit bigger.
14:39But I think sometimes people get so caught up or so paralyzed with the idea of getting started because they immediately think that, well, I've got 150K or 300K. I guess I have to invest all of that. When the answer is no, you don't. You can start as small as you want to start.
14:53Tony:Well, we have to take a short break, but when we come back, I want to talk about some lessons you've learned and also what you are teaching right now. We'll be right back. Everyone loves talking about big returns, but here's the problem. Returns don't tell you how efficient your investment actually is, Because once taxes hit, that great deal can look pretty average. That's why a lot of experienced investors focus on multifamily, not just for cash flow, but for the tax advantages. Depreciation can help offset income while the property is still producing. BAM Capital builds its strategy on that reality, focusing on active asset management and tax aware structuring to help accredited investors navigate complex markets.
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17:43Tony:Thank you guys so much for taking the time to check out our show sponsors. It's our sponsors that help make the show happen, and we love them. So, Toni, what are you teaching people? You post on YouTube. You post on Instagram. You have Alpha Host Academy. What is the one thing that you are teaching people right now about short-term rentals that maybe other people in the same realm are not teaching? What do you think is unique to you that you're telling people to do or not to do right now? I think there's two things. And the first one relates to market selection. The second one relates to deal analysis.
18:21on the market selection side. Now, and I guess I'll preface this by saying that market selection does somewhat depend on why you're investing in short-term rentals. If you're doing it because you just want a vacation house that someone else is going to help you pay for, well, then ignore this advice. But if you're looking for cash flow, if you're looking for a true performance property, something that's going to give you a good return, then this is the guidance that I give you. But I think the first thing is that people make the mistake of solely choosing Airbnb cities based on the places that they like to go.
18:57And 99 % of the time, especially for anyone that's like Midwest to East Coast, that means they want to buy in Florida. It's like, that's where everyone likes to vacation. That's where they think of when they want to buy an Airbnb. And because of that, a lot of the markets they initially think about are these markets that, yeah, they are great places to vacation, but they are also places where, A, there's an incredible premium on price because so many people want to go there. There's oftentimes an imbalance between supply and demand. So even if demand is incredibly strong, if supply has consistently outpaced demand, well, then we're going to see that reflected in things like lower ADRs, lower occupancies, and ultimately lower revenues.
19:39The next piece is that the level of competition in a lot of these markets is generally pretty strong as well. And you're now competing with hosts who maybe have five or 10 listings, and they do this for a living, and they've really got it dialed in on how to put together a really, really strong short-term rental experience for their guests. And you're competing with the pickleball courts, and you're competing with the in-ground heated pools, and you're competing with the golf simulators and all these other really strong amenities. So there's a price premium. There's oftentimes an imbalance of supply versus demand, and the competition is just stronger.
20:11Now, that doesn't mean you can't do well in those markets, but the bar is just higher. It's a higher bar to actually succeed. What I typically instruct folks to do is include those cities that you'd like to go vacation to, but also open up your perspective a little bit to maybe markets that you wouldn't have considered. Like places that maybe you personally would never even think about going. And if the data suggests that those markets are strong, well, then put aside maybe the emotional connection to Florida and instead go buy something in a market where the numbers actually work. And the things that I'm looking at are listing growth on a year-over-year basis, demand growth on a year-over-year basis, occupancy, ADR, REF PAR, and how strong the competition is.
20:51And if I can look across all those categories and see things moving in the right direction, I'll go buy something in the middle of wherever if I feel the numbers actually make sense.
21:00Tony:Now, what about what system or process are you building right now? Um, you've told me, you know, a couple of times that you're like coding and building apps and things like that, but what's like the, the biggest thing you're working on right now to put into place? Um, so when it comes to analyzing Airbnbs, and this is like one of the tools I've been kind of working on the background, um, historically, like I have like a, like an Excel based, like a Google sheet based calendar, um, that I use, but, but there's a lot that I do to kind of get to that point of actually running something through the deal.
21:32So this is actually the second thing that I kind of preach that I think a lot of folks get backwards. But whenever a lot of people think about buying an Airbnb, they start by going into Zillow and they scroll through Zillow or Redfin until they find something that kind of quote unquote looks nice. And then once they find this property that looks nice, well, then they start asking the questions, how much do I think this property can actually do in terms of revenue? What we typically teach folks is that you've got to do it the other way around. instead of starting with the property and saying, I found this property.
Read the full transcript
22:02Now let me back into how much money I think it can make. We start with the market and the listings that already exists in that market. And we identify all the properties in the top 10%. What are the commonalities there? The properties in that kind of middle 50%, what are they missing from the top 10 % has that they don't have? The properties in the bottom 25%, they must be missing a lot. So what are those things? And for those properties, maybe look like they should be doing better, but they aren't like, What's the differences there? So we do a very thorough analysis on the market first. And then we're able to build out what our buy box is based on those best practices that we identify across those different ranges of revenue.
22:38And now when we go into Zillow, we're not just searching for something that looks nice. We're searching for something that can actually check the boxes of what it is that we want. Like, I'll give you a really quick example. I was working with a student who was looking in Indianapolis. And they were looking at a four-bedroom. And what we found was that, A, a lot of the four bedrooms in Minneapolis, four and five bedrooms really, didn't have really great design. So that immediately is an opportunity for us just to professional design. That's going to make a big difference. But in terms of location, we needed to be somewhat close to the Speedway.
23:13We found that a lot of the top performers were in like walking distance either the Speedway. Or there's also like a thing, it's Cambridge Fieldhouse, just like their basketball stadium there as well. So that was another place that folks would congregate around. And then having flat land to amenitize your backyard correctly. There are some markets where flat land doesn't really matter. People aren't really using it that way. There are some markets where it's more important. Indy happened to be one of those markets where if you're buying a four-bedroom, having a large backyard where the kids can go play and do all those things, that was important.
23:41right? So we basically asked without even looking at Zillow or Redfin for what's for sale today, just by looking at the data of what's already performing, we were able to build out what we think that buy box should be. And then we just took that buy box and we layered it across what was for sale to try and find something that matches. So it's a small difference, but it's like the impact is astronomical in terms of the confidence you have when you underwrite. So I share all of that to say that that process is very manual of like clicking through all of those listings and looking at things like design and location and does it have views, does it not?
24:17And, you know, the construction quality and the architectural style, like there's so many data points we look at. And I've been working on a tool that helps me kind of synthesize some of that information. It's not perfect, but basically I can go through and do my initial just kind of like brain dump on every single listing. And then the AI tool can kind of go in there and synthesize everything that I put together. And there's also this piece where it'll go into that market, scrape all of the reviews from some of the top listings in that market, the bottom listings in that market, and help me identify, hey, who are the folks that are traveling here?
24:48What do they typically like about the properties in this market? And we're able to take that back in and pull that into our buy box as well. So I'm really focused right now on how do we improve the buy box research process of buying an Airbnb? be.
25:01Tony:It's crazy how like probably three, four years ago, like we interviewed Ariel and she was talking about how she was scrubbing data and doing all these things. And we were just like, oh my God. And now like with AI and everything, like here you are doing like setting up the same exact thing. Yeah. Probably even better. We should honestly bring her back on Ash because now with everything that's happened, I can't imagine the things that she's built. And for, for, for, for rookies that don't remember, we interviewed Ariel Herrera. We actually brought her on as a guest first. Then we brought her back because we liked this one piece of her story.
25:32But yeah, this was like pre AI explosion. She had built all these custom kind of web scrapers to help her identify kind of outsized opportunities. And I remember one, specifically one of the things that she had was she had this tool that would like scrape through Zillow and find mismatches between square footage and bedroom count. So she was like, man, this is a two bedroom, but it's square footage is like, you know, X percentage higher than the median square footage for all two bedrooms. Let me go look at that one. So we definitely got to get her back on. That was a great idea.
26:02Tony:Now, Tony, how long has it been since you left your job? Three, four years? No, no, no. It was December 2020. So just over five years now. Oh my gosh. Wow. That long. Okay. So during that time, your life has changed. Not going to a W-2 anymore, becoming a full-time real estate investor. What does a normal Tuesday look like for you? Not what you want it to look like, But what, like today, like what is a Tuesday look for you? And we don't record podcasts on Tuesdays usually. So it will be a different day than what I see. Yeah. I mean, I try, I try and look at like, like an overall week, right? Like, like what does my week look like and how do I spend time?
26:43So like, I'll, I'll tell you what my week this week looked like, right? A portion of my time goes toward content, right? Like us recording this podcast, you know, YouTube, Instagram, like there's a lot of content that we put out. So a portion of my time goes toward content creation. Um, running our, our education company, Alphonse Academy, right. Like in assisting there and, you know, running all those pieces that, that takes up a portion of my time. Um, the actual real estate side, luckily my wife handles most of the day to day in managing our portfolio. I'm more so focused on the next deal, uh, optimizing some of our systems and our processes, things of that sort.
27:16Right. So that, that gets a portion of my time. Um, and then really the, the rest is like me, you know, uh, you know, uh, spending probably way too much time in tools like cloud code and trying to build new things like that. Um, and then the rest is like family, right?
27:30Tony:Your awful men's league basketball team. Yeah. My, my terrible, which I'm actually sidelined right now. Cause I pulled my hamstring and, and last week's game. So currently on, on, on the IR for, for the, for the adult league right now. Um, but like, like this week, like yesterday, uh, my nephew, he's a, um, he's a, he's an eighth grade and he's going into high school next year. and there's this thing called dual enrollment where high school students can take local classes at the local community college and the community college had like this open house and you know I was able to take him you know pick him up after school and took him to that and you know that's what we did.
28:05Monday night me and Sarah you know and my in-laws without the kids went to Disneyland for this like a you know adult's day at Disneyland. You know it's like every every day we kind of get to pick and choose what it looks like and you know every Thursday at 10 o 'clock I take my daughter to ballet, right? So from 10 to 12, whenever Thursday, it's daddy and daughter time, right? So I think it's just the freedom to choose what the weeks look like. And if I want to clear my calendar for a day, I can do that. So it's really just the freedom of choosing what each day and week kind of looks like.
28:36Tony:I think also along with that, but having the flexibility in your day to know that like something may come up or you may need to pivot or change what's happening too. because like as much as I love being a real estate investor, like my attorney can call at any time and say, this house we have under contract, there's an issue. Now you need to get this, this and this and do this and whatever. And like the sooner you get, take care of it, like the sooner we can move on. And so I think that having, you know, being able to choose and pick your schedule is amazing, but still like having that flexibility to be able to take care of it.
29:12Tony:And the same goes with your personal life too. Like your kid gets sick at school, being able to be the one to go and pick them up and it's not be an issue at all. You can cancel what you have going on. So I think that's one of the really great things. Okay. So you mentioned that Sarah runs the day-to-day stuff for the short-term rentals. What does the partnership look like for you guys personally? Okay. So how do you separate work life from home life or do you not? Is it you're making dinner together and you're talking about things or is there some kind of separation? Give us a little insight into what this partnership looks like while being husband and wife.
29:53Yeah. Sarah, make sure that we don't just devolve into talking about business nonstop. But even for me, I feel like I don't want to talk about that as much either. But I think again, we're five and a half years into doing this full time together. So we've mostly found our rhythm. And, um, like there's a lot of things that happen where I don't, I don't even know that they happen and she, you know, she's just handling them. Uh, in the same way on my side of the business, like I just handle things. Right. And sometimes we'll loop each other in if it's like a bigger issue. Um, like also yesterday we hadn't, we had the employee quit, but one of our short term rentals, um, I actually got a call from like the water department saying like, Hey, there's been some irregularity in your water usage.
30:34We think you should check in on it. And then Sarah, you know, she called a bunch of different plumbers and folks. Now we've got a, you know,$1 ,000 or repair one of these properties. If there are things like that, we'll loop each other in. But honestly, I think because both of us really know our lanes and we've taken ownership over that part of the business, we don't have to share a lot with each other about what it looks like unless there's a big financial thing that we need to do. Sarah manages all of our VAs, manages our cleaners, manages all of our vendors. One thing she does always loop me in on is when we have to fire people typically.
31:08I think yesterday might have actually been the first time she fired someone on her own. But aside from that, it's usually me jumping in and having those conversations with her also. But aside from that, I mean, yeah, we both kind of know what our jobs are. We're staying in our lanes mostly.
31:21Tony:With my business partner for the liquor store, when we had to fire our manager, I was like, you need to come with me. I can't do this alone. You need to come. And so like we get there and we're in front of her and we're just staring. And I'm like, oh, my God, he's not going to say anything. I'm going to have to do it. That's not what I meant by coming with thee. And so it's, you know, like we, you know, the store is not profitable. It's losing money. You know, go through the whole thing or whatever. And like he did not say one word the whole time. Not the whole time. Just there. And I was like, this is not what I meant by you coming along.
32:01Tony:I got it out of my system though. So, yeah, but I just want to share that this is more so for folks who are listening. Um, and, and I learned this mostly my first, you know, I'll try and be concise here, right? But my, my first job out of college, I was, you know, 23, I think. Um, and, um, I was a frontline manager in a warehouse. And I think on that team, I'm, I think I had maybe like 60 hourly team members who reported to me. Um, some were younger than me. Some were much older than me. um there was a wide range of age personalities backgrounds and everything um part of the way that we had to fire people um at that job you know i was working for target um you know big corporate like like they have all of their hr systems very well documented we couldn't fire someone without really really really strong documentation right like you know target being such a big corporation people sue target all the time right for like wrongful termination so it was a very strong policy that there had to be a very very clear paper trail anytime we fired someone and so like we we have to document hey here's the first conversation here's the second conversation okay now now this is the third conversation so we're putting you on like a performance improvement plan or like a pip um and then now they're on the pip and if hey here are the things you need to do while you're on this pip to make sure that it doesn't progress from here okay hey you failed the pip you've got 30 days to correct performance okay hey 30 days and everyone always knew when someone was getting fired because uh the way the warehouse worked there was only uh one main interest everyone had to badge in and if you were getting fired your manager would be standing there at the door uh with you and there were like offices right off to the right so people always knew like if they saw their manager when they were walking in and they were on they were on a pip they were getting fired right and that always stuck with me ash because as a people leader people should never be surprised when they're getting fired and the the goal for me is always like someone should just like if they're getting fired they should just like kind of nod their head and say yeah yeah i i knew that this was coming so for me i always try and make sure that i reset expectations every step of the way but i also let them know where things are progressing and what you know my go-to line is like hey here here's here's what my issue is here's what i need to see from you and if it doesn't improve i just want to let you know what happens next that way there's no that they can't even push back because it's like yeah this is what you told me right so for all the folks that are listening you know even as you work with contractors even as you work with that's what i was saying it's great contractors yeah folks on your team right like like set that same expectation for everyone and it's like hey if this doesn't improve you know this is what's going to happen next right so just just my word of advice for all the folks that are listening well we have to take our last ad break but we You will be back with more from Tony after this.
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38:46Tony:Okay, welcome back. So, Tony, another thing that I want to touch on is where are you spending your time online now? Besides in Claude and building out ads, where are you looking on social media to consume content? And where are you also delivering out that content? Where should rookie investors be looking to actually consume content for real estate investing? Do you believe that one platform is more reliable or better than any other one? I think there's two stages of content consumption. And depending on where you're at, one stage might be better. There's the initial stage of just general awareness.
39:26You're just trying to really initially introduce yourself into maybe certain ideas or topics. And for our rookie investors, that's probably going to be real estate investing. So I think short form content is great for that because you can kind of get quick snapshots of different ideas and people's stories and what it looks like, and you can get the inspiration. But I think deep learning is very, very difficult on short form content, right? Because you're getting 60 seconds maybe at most. It's hard to really deeply understand something from a 60 second reel or TikTok. So I think short form can be great about introducing you to the people that you want to learn from.
40:05It can be great for just general discovery. But once you get past that initial stage, you've got to move to some form of long form content. It could be YouTube videos, right? Like you just true kind of talking to camera YouTube videos. It could be podcasts, whether that's on YouTube or Spotify, Apple, wherever it may be. In-person events, I think are fantastic. Probably one of my most, like my favorite ways to learn because not only are you now consuming content, but you're also doing in a group setting where you can have conversations with people and hear their stories. So like, I think in-person events are the absolute best, but for me, that's kind of like the sequence of events that I would move through.
40:42Initial kind of discovery, right? Just kind of getting the warm and fuzzies about the idea. Commitment to say, hey, I want to learn more about this and going deeper with long form content. And then really the pinnacle is getting in the room with other people and learning it together. Now, the last thing I'll add though, Ash, is that I think that folks should also shy away from consumption for the sake of consumption. And sometimes people, just to make themselves feel busy, they'll just watch more and read more and learn more. But at a certain point, you have to flip the switch from learning to application and just being really, I think, acutely aware of when that tipping point comes for you to make sure you don't just get stuck in that hamster wheel of learning more, learning more, and learning more without actually doing.
41:25Tony:I think that also goes for in-person events too, meetups, conferences, masterminds, things like that, because I did that. I spent a year going to every single in-person event. Yes, this was like right after COVID. So, you know, everybody wanted some kind of socialization, even me. And it was honestly a waste because it was just jumping from thing to thing to thing with no intention, with not what am I going to prioritize? What am I going to get out of this? What do I want to get out of it? What connections do I make? It was just I have to be there because or else I'm going to have FOMO that I'm going to miss out on learning some strategy and making some connection with really no plan in place as to how this is going to actually make me a better investor.
42:15Tony:And so I think that goes along with not like even just consuming content, but also the in-person things too. It's like really going to it with intention. We know the conference junkies, right? They're at every conference, but they aren't doing a whole heck of a lot, right? So you got to make progress. So last thing before we wrap up here is someone listening to this, Maybe they're a brand new investor, never done a deal yet, or they're looking to pivot into short-term rentals. What would you have them ask themselves before they took the leap into becoming a short-term rental investor? Same thing I say all the time in the podcast.
42:48What's your motivation? Are you looking to get into short-term rentals for the increased cash flow? Are you looking to get into it for the incredible tax benefits, the short-term rental tax loophole? Appreciation? Do you just want a vacation house? And I think once you can answer that question, and you've got to rank them, you have to identify which one are you optimizing for first, because there are no deals that exist where you're going to get an equally high amount of cash flow and appreciation. And it's a place that you want to vacation yourself, right? So you've got to pick and choose which ones you're optimizing for.
43:23And then once you're optimizing for whichever one, well, then take the first step of just trying to decide what market actually supports that goal. And then once you've got the market, then you start looking for the deals. And then once you've got the deal, then you focus on the setup. But I think where most people kind of start making mistakes when they jump into short-term rentals is that they do it without clarity on those motivations. And they do it with a very poor execution framework on how to choose the right cities, how to analyze deals correctly, and how to set those properties up. So one step at a time for each one of those.
43:52Tony:Well, rookies, thank you so much for listening today. I'm Ashley. He's Tony. And if you guys haven't already, make sure you are subscribed to our YouTube channel, Real Estate Rookie. Well, Tony, thank you so much for sharing your journey with us today. We'll see you guys on the next episode. Hey, rookies, if you're watching this, we want you to apply to be a guest on the Real Estate Rookie podcast. That's right. Ashley and I are looking for amazing stories just like yours to be a part of our Real Estate Rookie podcast. Now look, you don't need to be an expert. You don't need to have done thousands of deals.
44:23Even if you've done one deal, your story could help inspire the next listener.
44:27Tony:As a rookie investor, especially if you just got your first deal, it is all fresh in your minds and you are the best person to tell your story, give your experience on how you got it done to help someone else get their first deal. So head over to biggerpockets.com slash guest if you want to be a part of our show. Again, that's biggerpockets.com slash guest and we'd love to have you on.
From the publisher
Many rookies think things become easy once you’ve built a large real estate portfolio, but that’s far from true. Even with 26 short-term rentals, a 13-unit hotel, and a few house flips under his belt, Tony deals with many of the typical rookie challenges. In today’s episode, he’s sharing the lessons he’s learned and the rental pivots he’s making so YOU can grow and scale like him!
Welcome back to the Real Estate Rookie podcast! Last time we checked in with Tony about his real estate business, he was in the process of stabilizing his new hotel. Now, with an entire calendar year in the books, we’ll revisit the property and how it’s performing today. We’ll also hear about Tony’s next hotel investment and how he’s approaching it differently now that he has proof of concept.
Tony also outlines the best course of action for new investors who want to break into the short-term rental space in 2026. Finally, what does a day in the life of a full-time real estate investor look like? Tony gives you an inside look at the flexibility he enjoys by owning rental properties that you don’t get with a nine-to-five job!
In This Episode We Cover
Rental pivots Tony’s making in 2026 for even bigger returns
Updates on Tony’s rental portfolio and his 13-unit hotel investment
The biggest pain points when investing in a smaller real estate market
What Tony’s average week looks like as a full-time real estate rental investor
First steps for rookies looking to invest in short-term rentals in 2026
How to build a real estate business that gives you more freedom and flexibility
And So Much More!
Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/rookie-729.
Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com.
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