He “Stacked” 5 Properties in 6 Years: Now He Lives and Travels for Free!

8 Dec 2025 · 45 min · 22 chapters

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In short

Episode topic: Ross Alcorn explains how a 2018 $12,000 tax bill pushed him to use real estate for tax shelter and long-term wealth, then “stack” five properties in about six years to fund freedom and travel.

Guest background

Ross spent 10+ years as a medical device/healthcare software sales rep (high commission). He started investing while W2-employed, reading real estate books and networking with a partner who had real estate experience (commercial buildings/flooring background).

Key claims

Real estate’s biggest early unlock for high earners is tax benefits (not just cash flow). Getting started beats overanalyzing. House hacking and taking action (even sight-unseen) can accelerate momentum. Credit cards can fund furnishings/rehabs via welcome bonuses and 0% interest cards without “bad debt” if paid on time.

Notable examples

Charlotte house hack bought via FaceTime; roommate covered 1/3 to nearly 1/2 of the mortgage. Later he bought Lake Wiley waterfront land (about 130 feet shoreline) and negotiated around an easement restricting dock building; he plans an ADU. Portfolio timeline: first house hack 2019; second property under contract June 2020; land closed Oct 2020; townhome closed May 2021; long-term rental then medium-term rentals using Furnished Finder; additional condo Oct 2023; moved into new home Feb 2024. Credit-card tools: “Wallet” and “CardPointers”; payment integrations: Melio (business) and “Plastique” (personal).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Turning Point: Ross's Tax Bill Experience

0:45 to 3:54

Ross shares how a hefty tax bill in 2018 prompted his journey into real estate investment.

“So yeah, really excited to dive into kind of how you guys helped, as well as just some strategies that I learned along the way.”

Understanding Real Estate Investing Benefits

3:54 to 6:34

Discussion on the overlooked tax benefits and long-term appreciation of real estate investing.

“Because if you're making 500 grand a year, the cash flow you're going to make from real estate is probably going to be negligible in the very short term.”

Mindset Shift: From Stocks to Real Estate

6:34 to 9:45

Ross explains how his mindset evolved from stock market investing to real estate.

“And there's appreciation availability and there's prices are going to be lower and potentially cashflow.”

The Importance of Filtering Advice

9:45 to 11:29

Ross emphasizes the need to evaluate the source of financial advice.

“of, man, I read this headline or had knew this guy once who knew this guy once who lost all their money in real estate.”

Starting Out: The House Hack via FaceTime

11:29 to 13:20

Ross recounts his unique experience of buying a property over FaceTime as a first investment.

“And I started my own business went on my own.”

Taking Action in Real Estate Investing

14:01 to 17:04

Learn the importance of taking action and avoiding analysis paralysis in real estate.

“And that really gave me that confidence to buy.”

Taking Action in Real Estate Investing

17:08 to 18:43

Learn the importance of taking action and avoiding analysis paralysis in real estate.

“If you're heading out of town and your home is sitting empty, you could list your space on Airbnb while you're away and turn those unused nights into extra income.”

Taking Action in Real Estate Investing

18:47 to 18:58

Learn the importance of taking action and avoiding analysis paralysis in real estate.

“and support our show by saying you heard about Indeed on this podcast.”

Building Momentum in Property Investments

19:38 to 22:56

Understand how early successes lead to confidence in expanding your real estate portfolio.

“So went, saw that property and actually around that same time, it was brand new construction.”

Structuring Partnerships in Real Estate

22:56 to 28:01

Learn how to effectively structure partnerships in real estate investments.

“sellers all the time with mailers and, and text and all that asking for the property.”
Show all 22 chapters

Building a Partnership for Real Estate

28:01 to 29:56

Learn about the importance of alignment and communication in forming real estate partnerships.

“we're figuring out what's important to one another.”

Building a Partnership for Real Estate

29:57 to 30:34

Learn about the importance of alignment and communication in forming real estate partnerships.

“When you're just getting started in real estate, it feels like every dollar has a job, down payment, reserves, repairs.”

Building a Partnership for Real Estate

30:37 to 31:12

Learn about the importance of alignment and communication in forming real estate partnerships.

“quietly dropped while my day-to-day spending crept up a little bit.”

Building a Partnership for Real Estate

31:13 to 31:50

Learn about the importance of alignment and communication in forming real estate partnerships.

“People love to call real estate passive income, which is interesting because most of the investors I know are very busy.”

Building a Partnership for Real Estate

31:55 to 32:24

Learn about the importance of alignment and communication in forming real estate partnerships.

“With Avail, rental listings can be published to 24 top rental sites with one click, completely free.”

Building a Partnership for Real Estate

32:25 to 32:56

Learn about the importance of alignment and communication in forming real estate partnerships.

“Most investors only think about insurance when something goes wrong.”

Leveraging Credit Card Points for Real Estate

33:03 to 37:44

Explore strategies for using credit cards to finance renovations and maximize rewards.

“You've actually pivoted Ross into working for yourself and you've got a business around credit card points.”

Payment Solutions for Vendors

37:45 to 41:22

Find out how to pay vendors who don't accept credit cards using innovative tools.

“So what is the system or tool that you use to keep track of all of your different credit cards and the kind of bonuses or intro bonuses that you're on?”

Understanding Fees and Payment Systems

41:23 to 42:01

Discuss the hidden fees in payment systems and how to optimize your payment strategies.

“You know, I was wondering about that fee.”

Maximizing Credit Card Points for Travel

42:01 to 44:00

Learn strategies to effectively use credit card points for travel savings.

“It's like a 7 % fee they're charging me to pay my cleaners through this.”

Partnerships and Point Allocation

44:01 to 47:38

Discover how to split credit card points and benefits in partnerships.

“And part of it was because it was a partnership.”

Ross's Journey and Resources

47:39 to 48:59

Explore Ross's journey in real estate and learn about useful resources.

“I think the business idea, Ash, that we need to go out and execute on is just how can we get all the people that we know that do renovations to use our credit cards?”
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Transcript

Automatic transcript. May contain errors.

0:00Ashley Kerr:A$12 ,000 tax bill and 200 hotel nights later, Ross Alcorn swore he'd never trade time for commissions again. Five years later, his house hacks fund his freedom and his side hustle pays for his first class flight.

0:14Tony Robinson:Today's guest proves that getting started really isn't as complicated as you think.

0:24Ashley Kerr:This is the Real Estate Rookie Podcast. I'm Ashley Kerr.

0:27Tony Robinson:And I'm Tony J. Robinson. And let's give a big warm welcome to Ross. Ross, thanks for joining us today, brother. Hey, thanks so much for having me, Ashley and Tony. This is a pretty surreal moment. Got to listen to both your podcasts from past five years. And I know we connected out at an in-person event. And I would have been kicking myself if I didn't come say what's up. So yeah, really excited to dive into kind of how you guys helped, as well as just some strategies that I learned along the way. So excited to be here.

0:54Ashley Kerr:Yeah, and we're excited to learn from you too, Ross. I want to start off with, you've said that 2018 tax bill was your breaking point. What was going through your mind then? And what did that moment teach you about actual wealth building? Yeah, absolutely. So I was a, just for some background, I was for 10 plus years of medical device and healthcare software sales rep. And as a lot of people know, you're very high commission based. and in 2018 had a really good year, was renting with three other guys in the Northern Virginia, DC area. And yeah, at the end of the year, saw how much I made, saw how much I owed in taxes.

1:33And then when January came around, realized I still had to stroke a massive check to the IRS. And I was like, okay, what's going on here? Like I invest in stocks. I invest right in index funds. I have the foundation in place from the beginning, but I had heard a long time that real estate was a great way to just shelter that. And through different conversations that my partner and I, one of my business partners now on some of the properties had, he came from more real estate background. So we had been talking for a couple of years. And really after that, it kind of paired with wanting to buy a house.

2:10And that's when really the mindset got going. And that's when I started to dive more into real estate, reading the books, listening to podcasts, figuring out how do I save some money?

2:21Tony Robinson:Ross, I think one of the biggest things that people overlook when it comes to investing in real estate is the tax benefits. And obviously, there's a long-term appreciation. There's the cash flow, which I think a lot of people understand. But one of the real unlocks in real estate investing, and part of the reason that so many successful people who make their money outside of real estate eventually end up investing in real estate, is because of those tax benefits. Um, I guess if you know, like off the top of your head, what was like your, your tax bracket, you know, like, like, what did that look like for how much were you actually spending in taxes?

2:55It was the highest amount. I think I on, uh, I think I had to stroke a check in January for 33 grand. And then we, we, we turned to that. We had an inside joke with our friends. We would just say taxes. Cause we're like, it's, it's stuck with me. Right. Um, so that was what I had to pay outside of, I think it was like 175 grand on my tax bill. So I had made over half a million that year. And it was, yeah, it was pretty insane. That was really eyeopening where I was like, all right, I know I'm going to try to perform at this level over the coming years, which that was my highest earning year. And now I think to myself, wow, there's some years where I've made less than that.

3:32And I paid in taxes every year after, right? So that's when it really was that wake up call. And that's, yeah, that's when I started to realize, like, I need to figure out a strategy to shelter this. And that was prior to thinking anything about starting my own business, entrepreneurship, right? Those things that was I'm a W2 earner, I'm going to be a high commission sales rep for a long time.

3:53Tony Robinson:And Ross, I think it's an important point, because, especially for people who are high income earning, I think that there's potentially maybe more benefit for investing in real estate from a tax perspective and a long-term appreciation than there is from immediate cash flow today. Because if you're making 500 grand a year, the cash flow you're going to make from real estate is probably going to be negligible in the very short term. But the bigger benefit that you'll get is the ability to reduce your taxable income by half or maybe even more. And I know we'll get into strategies and things like that later, but it's just an important point that I want to call out because I feel that so much of social media today it's just about cashflow, this and profits and all those other things.

4:33Tony Robinson:But when you take a big step back, I think taxes are a big part of that. So how did your, your first exposure to real estate education shift your mindset from just kind of stacking money aside to actually starting to build that real estate portfolio? Yeah. So I think first it was just understanding the things that you mentioned, you know, tax benefits, equity buildup long-term having, you know, if you're owning those properties, having people paying down the loans, the mortgage, and it wasn't what is, you know, framed on Instagram and TikTok that we get hit with ads every day about, right? Go buy a couple properties, go chill on the beach, you know, drink, you know, Mai Tais, that's not how it is.

5:11So that is what got me thinking. And then if I could shelter that while at the same time investing, you know, in the stock market for some of those, some more risky, but more, you know, rewarding, as well as index funds, that just built out a diversified portfolio. And that's really what got me thinking. And then I never even thought, hey, I'm going to have five properties be a landlord. It was just, hey, I want to move to this market where it's very affordable. I'll buy one, maybe I'll rent it out. And over time, this is a growing market. And when I traveled as a sales rep, I always laughed. And this is what got my mind going.

5:50And I think it goes back to my creative days when I was starting my entrepreneur journey, knocking on doors, starting my grass cutting business. And I would see how I would target yards. And this is, you can probably see the sales going on in my mind, but I would target yards that had high grass because I'm like, all right, they're lazy. I need to go cut their grass. And that's how people in the creative finance world, right? Find deals. But that being said, when I was flying to and from DC to North Carolina, Northern Virginia had so many houses and there wasn't a lot of dirt. You're flying over Lake Norman and Charlotte, it was all dirt.

6:24And I'm like, oh my gosh, there's so much opportunity here. So that's when it kind of clicked that I need to figure out a way that I can move to a area that is growing and right. And there's appreciation availability and there's prices are going to be lower and potentially cashflow. But that was kind of that long-term mindset that really made it, made it happen.

6:43Ashley Kerr:Now, Ross, during this time, were you doing any kind of research on real estate or any kind of education? Was there some kind of aha moment for you maybe where you're like this book or this podcast or doing this is like, I need to follow this. So yeah, some of the first books that I started to read was my buddy who, you know, now we own two properties together. He said, Hey, go check this out. Flip your future by Ryan Pineda. And then there was also the ABCs of real estate investing. So that kind of just got the foundation going before diving into every single strategy. I know most people, you know, they, they, they read rich dad, poor dad.

7:25You know, I read that later just because everyone recommended it. But luckily my dad, you know, they were, hey, go invest long term, whether it's in stocks, whether it's somewhat in real estate, but they were more in the market, not real estate. So having my friend who's now my partner, kind of us having those conversations long-term, giving those books, that's then, right, what kept it going.

7:47Ashley Kerr:So with this shift with your dad and then meeting your partner, was there any kind of mindset shift you had to have from your dad, you know, primarily investing into the stock market and now you're kind of trying to adjust your mindset to real estate investing? Yeah, I think it was a lot of questions, right? It was just asking my partner, understanding, you know, what are the reasons, you know, behind it. And he had some family, um, that were his uncles who had commercial buildings, you know, his parents had flooring companies, like they were really on the real estate side. So it was that blend.

8:19And it wasn't just saying, okay, I'm going all in. It was just diving deeper, doing the research, asking the questions. Um, and, you know, and he hadn't said, Hey, they have all these buildings. This is how they do it. And it did have to change that mindset of, you know, and I think a lot of times people grow up and they are told one thing and they don't expand that. I think one thing that I always try to do is listen to what everyone else who's doing things successfully and study their business and study different areas. And that's where then that helped me get outside of that narrow mindset of, oh, I can make all money in stocks to, hey, real estate.

8:59Other people have done it. 90 % of millionaires are made out of real estate. So doing those kind of gave that leap and got me to start listening more. And that's kind of what transitioned into where we are now.

9:12Tony Robinson:Ross, you just made an incredibly important point that I hope every single person listening paid attention to. We all have well-meaning, well-intentioned people in our life who want to give us advice. But that advice is always based on their set of experiences and their worldview, and their own successes and their own failures and their own fears. And sometimes the person giving the advice about becoming a real estate investor or building wealth, maybe hasn't done that themselves. And their advice is coming from a place of fear, or a place of, man, I read this headline or had knew this guy once who knew this guy once who lost all their money in real estate.

9:54Tony Robinson:So I think it's important for rookies who are listening to filter out the advice that we get based on the level of experience that person actually has in implementing that advice, right? And well-intentioned advice can be bad advice, right? Nothing about the person, but just make sure we can filter that out. So I appreciate sharing that. I want to talk about your first deal though, because you started with what Ash I think, and what we highlight on the podcast oftentimes is one of the best ways for Ricky investors to get started. And that's what the house hack, but yours was kind of unique because you, you bought this house hack via FaceTime, which I think might be one of the first stories you've heard of someone buying a property over FaceTime.

10:32Tony Robinson:So walk us through that story, Ross. Yeah, for sure. And before I dive into that, there is one point I do want to make just around what you had said, Tony, because I think it is very important. If you are getting started, whether in your W2 job, whether you're starting to invest in real estate, like one of my favorite things to ask people who were successful, you know, who were 30, 40, 50, 60, right. Different areas of their life is what are things that you regret? What are things like mistakes that you made? Like in talking to people who were successful because they could give you those advice and then taking that and not just trusting, right.

11:01The people who were your age, who you're going out to the bars with, or you were doing this right. Or who weren't where you wanted to be. So always kind of putting yourself in the right room and asking the right questions. So that's a, I wanted to just touch on that.

11:14Tony Robinson:But yeah, Ross, really quick. It's a really good point. And I'm curious now from the folks that you've spoken with, we've kind of guided you in this direction that you've gone on. What was some of that advice like, like, you know, enlighten our rookie audience with some of the same knowledge that you were able to get? I wish I worked less. I wish I invested earlier. I wish I traveled more. So what did I do when I was 23? I traveled as much as possible. That's why I have a travel company. Now I invested all my money. And I started my own business went on my own. So I could obviously work a lot now, but work less down the road.

11:44So I think it's just asking the right questions and building out that life that you want to. And that's a lot of the reason why a lot of people listen to the show is they want that financial freedom. They want that ability to go do what they want. And that's what real estate does provide.

11:58Ashley Kerr:Now, Ross, with this first house hack that you found on FaceTime, was this in a different market as to why you weren't physically there? Yeah. So it was in Charlotte. So I was living in Northern Virginia. Um, I remember very clearly I was down here. I was, I had the North Carolina territory when I was a sales rep. Um, so I was down here and I had a lot of friends, half my friends moved from or moved to Charlotte, half moved in Northern Virginia. So I was watching the Alabama Clemson national championship game. My buddy said, Hey, I bought my condo for 230 grand. And I'm like, Oh my gosh, the crappy houses that the neighborhood that we live in are like 800 grand.

12:35What the heck? And I don't want to, I was 27 single. I was, I was like, I don't want to live out in the suburbs yet. I want to live in the city. So immediately my wheels got turning and he actually said, hey, my neighbor who is a loan officer is actually selling her property. Two bed, two bath condo, seemed perfect. But there was an HOA cap for non-rentals. I wanted to have the flexibility, right? But the good thing is she was a lender and she then was able, I used her as my lender for my first property. She introduced me to a agent. When I came down for the next time, I met the agent, we went out and toured different properties.

13:10And I had said my budget was about 250 to 300K. But as I did more research, started to realize, here's the good markets that you want to be in. If I have to pay another 50 grand to acquire that property, I'll do it. And at the same time, while I was thinking through, hey, maybe I get a three bed new townhome because then I can rent it out to a roommate, have an office because I work from home. I was also at the same time having conversations with people that I knew, like, and trusted, trying to figure out, Hey, are there people, you know, who might need, or who might want to rent? And it actually worked out very well that one of my close friends was like, yeah, actually I need somewhere to live for about a year or so.

13:48Um, why I look to buy a house. So that worked out great. He covered, you know, a third to almost half of the mortgage. Um, and then it worked out where I got an office, I got my bedroom, he got his own bedroom. And that really gave me that confidence to buy. And yeah, I built that trust up with her and she kind of knew my buy box. And I just communicating with her said, hey, you know, if you find something, I trust you, we have the, you know, my buy box in place. if you say, yeah, let's do it. FaceTime me. And, you know, I think the biggest thing, and I know we'll probably get to this is not having analysis paralysis, right?

14:26Taking action, I think is the biggest thing. And I see it so much from a lot of my friends where like, oh, I wish I bought in 2020, 2021. And they wait. And then they got, you know, a rate that's double what I got on two properties because kind of took that leap and say, it's going to work out. You know, I'm 30 years old and 30 years is probably going to be right more than it is now. So I think that's, that's probably that lesson is just taking action and not overanalyzing things. You know, when you have trust and you have, you've done your homework.

14:57Ashley Kerr:That's great advice, Ross. So we went over how Ross took the leap, bought sight unseen, and it's going to pay off big, but how do you go from one FaceTime deal to negotiating a lakefront property and using 0 % cards to fund furniture. We'll go over that right after a word from today's show sponsor. When you buy your first rental property, there's usually a moment right before you pull the trigger where your brain starts spiraling a little. What if I'm making a mistake? What if I can't figure this out? What if this whole thing becomes way more complicated than I expected? Honestly, building any business feels like that at first.

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18:24Ashley Kerr:And speaking of results, in the minute I've been talking to you, 23 people just got hired through Indeed Worldwide. There's no need to wait any longer. Speed up your hiring right now with Indeed. And listeners of the show will get a$75 sponsored job credit to get your jobs more visibility at Indeed.com slash rookie. Just go to Indeed.com slash rookie right now and support our show by saying you heard about Indeed on this podcast. That's indeed.com slash rookie. Terms and conditions apply. Hiring Indeed is all you need. Okay. So Ross, after that first deal, you caught momentum fast. You started stacking properties and even buying land on Lake Wiley.

19:07Ashley Kerr:Let's unpack that next step. So how did that first property success give you the confidence and where did you get the capital to keep going? Yeah, so it gave me the confidence of, okay, Charlotte's a good market, having conversations with other people, starting to network with the right people and just continuing to have those conversations with my buddy who now is a partner on two properties of, hey, let's maybe buy something. My roommate moved out after a year. I thought, okay, why don't we try to go get another property and I'll live in it. We can house hack. and we both put 50 % down. So went, saw that property and actually around that same time, it was brand new construction.

Read the full transcript

19:49Again, taking action, knowing this is an up and coming neighborhood. It's exactly what we want. We went under contract on that property. First time we walked through in a hard hat, got a great deal on it. So that didn't close for another nine months, but at the same time, having that confidence was, we were a Lake family. So My grandparents had a lake house that we built a ton of memories on for 25 years. I have a boat out on Lake Norman that I was like, you know what? If I'm going to have a forever home, I want it to be on the lake. If you're familiar with Charlotte, there's Lake Norman, 25 minutes north.

20:25Lake Wiley, 25 minutes south. Lake Norman is where MJ, you also have the NASCAR drivers, all the Hornets, all the Panthers players live. It's a lot more expensive. It's also more saturated. So for me as an investor and someone who's trying to get a good deal, I'm like, okay, let me go to Lake Wiley. It's also on the South Carolina side where there's the bottom 5 % in taxes. So I'm thinking that way strategically and just started to look at things. My same thing, business partner who has uncles who have bought property, sat on it for five or 10 years. I had conversations with them. I had no idea what to look out for right in land.

21:06So they said, hey, here's the things you want to do. Here's the questions you want to ask. These are the things you want to go through with your agent as well as the others. And then you can vet those things out. So going through that process, went and saw some, found a property that I really liked. And threw out a lowball offer. It was at$300 ,000. And I said, Hey, let's go to 50. And I was, but it was during COVID. So I knew that there was probably pressure on right, the seller, and it had been sitting there for a while. So I knew there was probably pressure on the seller to offload it. And I, you know, building that relationship with the agent, understanding his priorities, why he owned it, come to find out his son was the one who spoke too soon and threw back the offer at two 50.

21:48And I was at a friend's wedding and I started laughing. I'm like, there's no, or 270, sorry, encountered. And I just started laughing. I'm like, wow, this really worked. All right, let's go lower and went back. And then he got kind of pissed and went, tried to go up to 75. We landed on 270. But the funding piece came from, again, going back to building the right foundation was investing 10 % of every paycheck from my Philips account from my W2 each quarter we got, or each time you bought, you got 15 % off the stock. So I already knew I was walking into money at a 15 % discount. And over that five year period that I was there, I was able to double that stock.

22:29So I used that for 43 ,000 of the down payment, and then took out a HELOC on the other, on the first town whom I bought to use as that other part, just because I didn't want to get capital gains taxes from selling my stock since I was in that higher income bracket at the time. So there was a lot of pieces, but that's how I funded that. And yeah, I think it just, again, it was just like, you got to take action. I get hit up by sellers all the time with mailers and, and text and all that asking for the property. And yeah, some, sometimes I want to text something funny back and I'm like, no, I'm just not responding.

23:06Then they're just going to hammer me. So that's, that's kind of how I, uh, how I got into it. And yeah, it's, it's been a great investment and, you know, looking to build on it three to five years, you know, whenever we decide the time's right.

23:17Tony Robinson:So Ross, let me understand. So it's a, it's a single family home, but there's also land to build on it as well. Am I understanding that correctly? So it's just land. So it's three floors. Yeah. Yeah. So three fourths of an acre. It's about 130 waterfront, 130 feet of shoreline and it's waterfront in a cove on Lake Wiley. So I saw that as right. It's going to be able to build on it. I think the cool part is, is there's another half acre next to it that the owner owns as well, but there was an easement on it. so he's been holding on to that now and the agent now has come back to me and said hey are you interested in it because I could potentially build an ADU on that and that's you know that's where the creative part of building those relationships comes into play Ross can you explain what an

24:03Ashley Kerr:easement is and why you didn't purchase it at first because of the easement I'm gonna say I gotta go back and it's it's not it's not great um do you know do you know what the easement like the restriction is for the easement? So you can't build a dock on that property. So that was one of the biggest red, not red flags, but one of the reasons I didn't buy it. Cause I wanted to build a dock, build a house on it, but it's cornered next to it, but there was an easement from some water runoff. But if you were to purchase both lots, it doesn't matter. Cause you could build an ADU on it, but to build your own home and not be able to build that dock, that's kind of where it could be a challenge.

24:41Ashley Kerr:So that easement is for you to have water runoff onto their property. Yeah. Then for the land you own now. Yeah. So it makes sense for you to buy it rather than it'd be a lot harder to sell it to anybody else because you already have access to the property because of that easement. Yeah.

24:58Tony Robinson:So Ross, what's the plan then? Because I know obviously it's like a kind of long-term buy and hold, but at what point, or maybe if I frame the question this way. What do you think needs to happen in order for you to say now is the time to build? When we want to move out of the city. We're a mile from the city and all our friends. So we're just kind of still at that stage of life. And yeah, when when the time comes, being part of my own business. Yeah. So Ross, just for our viewers that are coming along with us, just give us like the 30 ,000 foot timeline of your portfolio. So you started with the house hack and just walk us through what happened from there to kind of where you are today.

25:37Yeah. So bought the first house hack 2019, um, went under contract on the second property in June of 2020, uh, purchased the land in October of 2020 closed on that, you know, second town home that we went on our contract, um, in May of 2021. Um, and then from there lived there, started renting out the first house as a long-term rental. And then, um, me and my, But as my partner and I learned the ropes, decided, hey, let's go and buy another property. When the market and rates went up, we saw it was a good buying opportunity. And in October 2023, purchased a two-bed, two-bath condo and started to do medium-term rentals.

26:20My wife actually had one. So when she moved in with me in January 2023, she actually started doing hers. So I had been studying Furnish Finder. being in the healthcare industry, knew that and started to do that strategy. And then her and I purchased the home that we're in now in February of 2024 and moved a mile up the street because we needed more closet space because it wasn't just me as a guy. And then we got a two and a half year old bulldog and we needed a little patch of grass out back for him to run around.

26:50Tony Robinson:So I think one of the big questions that we always get from our rookie audience is, how do we structure the partnership? And you've taken down a couple of deals with someone else. How were you structuring the partnership and what conversations went into trying to identify the best way to structure that partnership? Yeah. So I think the first thing is you always mean, you always want to be aligned with your partner on trust. That's the number one thing, no matter what the numbers say, no matter, Oh my gosh, this is a great deal. It's like, do you know, do you like, do you trust that person? Because this is a huge decision.

27:21And And even if they're friends, right, do you trust that they're going to be, you know, if you're both type A and you're both really organized, like you might butt heads. But if one's really good at one thing, one's really good at another, like that's where it's a really good partnership. And you have to be able to have those candid, open, honest conversations because life changes happen. So that's probably the most important point before you get started, because I've heard horror stories from people that I know, obviously, you know, people in the business. So that's number one. but I think if you go back to like what I was talking about, these conversations started in 2016, right?

27:58We didn't purchase our first deal until 2020. So those were those we're learning, we're figuring out what's important to one another. And we're seeing like, we want to build a future together. And yes, we're best friends, but at the same time, like we both know what one another is good at and one another is not great at. So aligning those things and just, We had Tuesday weekly calls every single week at 5 p.m. And he had a brand-newborn daughter, a W-2 job, right? So we made sure that we were doing those things. And we aligned it where even though we house hacked, we put 50 % down each. And then that's where we both were on the deed and then for both properties.

28:41So loan was out in my name for the first one. we had his name on the deed. And then from there, you know, if you wanted to roll it into an LLC, you could, um, there's a specific thing we can get into on that property since we're at a 2.75 rate that right. There's, there's sometimes they may not want you to, but yeah, there's, there's strategies of, even if you have that partner, you know, do you roll it in LLC or how do you structure that? So happy to dive into, you know, how we did that.

29:08Tony Robinson:I mean, I just appreciate that you started with before the structure, just, Hey, here's everything that happened before we even had that conversation. And I think that's a point that Ash and I try and drive home often is that without the alignment, without the communication, without getting to know, like and trust each other beforehand, it's hard to even have a good foundation for a partnership. And ideally, you want to date a little bit before you jump into something. Like you said, it was four years of you guys going back and forth before you actually made the decision to buy together. And I do think that's the best approach.

29:39Tony Robinson:Now, Ross, you've built a system around building your business. But you've also got a really unique skill set when it comes to credit cards and points. And you found a unique way to merge your business and your credit card points in a way that I think more Rickies need to know about. So we're going to go over what that strategy is after a quick word from today's show sponsors.

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32:31Tony Robinson:A tenant injury, storm damage, loss of rent. Then suddenly, the cheapest policy doesn't feel like the best one anymore. That's why a lot of BiggerPockets investors use steadily for landlord insurance designed specifically for rental properties. Whether you own one property or a growing portfolio, they make it simple to get covered properly. And BiggerPockets Pro members get an extra 5 % off their landlord insurance premiums. Visit biggerpockets.com slash landlord insurance to get a quote today. All right. So you bought some homes, you bought some land, but you didn't just stop there. You've actually pivoted Ross into working for yourself and you've got a business around credit card points.

33:10Tony Robinson:And I want to talk about that. Credit card points, maybe we can start with a quick definition, but how can a rookie investor safely use credit cards to finance things like renovations or furnishings without going into bad debt? Yeah. So there's two sides, right? If you're buying your personal home, using a card to purchase those furnishings, I always recommend depending on, and this just depends on where you're at and level of spend. There's different cards. So one of the best ways to earn the most points is by a welcome offer. So if you have a$5 ,000 expense and you spend that in the first three months, you then can earn, let's just say it's 80 to 100 ,000 points.

33:54You're getting a big bang for your buck. If you're for another example, that's what I did when I bought my first townhome is open Chase Sapphire Reserve because I was traveling a lot. You know, most of my income goes towards travel. So I was able to earn that, you know, big welcome bonus. Another example, though, is from a from a strategic standpoint and also not going into debt would be when my wife and I bought this house. We had just gotten engaged. You know, we knew we were about to pay a lot of money for a wedding. Um, and right. Like for us, we were putting down money that we again, took action.

34:30We weren't even planning on buying a house. And the fact that we did enclose within 60 days, like we weren't trying to bring another 10, 15 grand to furnish the property right then and there. So being able to understand there are 0 % interest credit cards that you can get. So my suggestion is don't go to whatever the furniture store, home Depot finance the card with them, get the cards that have the right amount of points, whether that's Chase, Amex, Capital One, because those are the banks that you then can use those points to go transfer and travel. But that 0 % interest strategy is very key.

35:05If you want to have just an additional float, a little bit of leverage, those type of things to then not have to come up with that capital right then and there. And then you have to make sure one, that you have the minimum balance paid off on auto pay. And that's really it. But But if you miss that, then that money is due at that time. So just always make sure that you have those things in place. So that's on the personal side. And we're happy to dive into the business side and how my partner and I learned that, how I help investors now, those more strategic ways. But yeah, if you're wanting to do that, that's very simple on the furnishings.

35:43And then there's some other fun stuff that's coming out around mortgages, landlording, all that stuff that we can dive into.

35:49Ashley Kerr:Well, I think too, with a 0 % interest credit card, not only just furnishing, but rehab materials. That's what I've gotten the 0 % cards for is to do the rehab. And then either when I sell the property or I refinance it, I just pay the card off. And like some of them, like I think the most recent one I had done was like 12 months, 0%. But if you made like your on-time minimum payment for like six months, they would extend it to 18 months. That's a really long time, especially if you're not doing a huge, huge project to be able to, you know, refinance or, you know, sell the property to be able to pay that off before the interest kicks in on that, that card.

36:34I was going to say the renovation is key, right? And if you're doing prime example, when we first moved into this home, we wanted to, you know, the other homes that I owned, you know, I bought on my wife wasn't there. So we were sticking with the flat white paint, but when we moved in here, right, she wanted to have the drenched all, you know, same color, right? Do it all, which it looks great. But what we had to do is pay contractors with cards. And again, when we had those expenses, we had to decide how do we want to do that. So having that 0 % interest was really key on the personal side. And same thing when we did when my business partner, Mike and I did a rehab, a light rehab floors, you know, cabinets and paint, same thing.

37:16We did the Chase Business Unlimited Inc., which is 0 % interest. We were able to get that$100 ,000, well,$100 ,000, I wish, 100K welcome bonus and points from Chase. And then that translates into one business class flight worth$5 ,600 on Qatar Q Suites in a lay down seat that I just took in April on our honeymoon. So like that's where, right, maximizing and optimizing those is really key.

37:44Tony Robinson:Ross, let me ask, because I think just hearing all these different cards you're throwing out, like I'm already overwhelmed. So what is the system or tool that you use to keep track of all of your different credit cards and the kind of bonuses or intro bonuses that you're on? How does someone do all this without losing track of everything? Yeah, for sure. So there's a couple tools, but just to keep it simple for tracking, you have a ward wallet and then you have card pointers. So a ward wallet, you can keep all your cards. You have all your cards, you have the different points in there. And if you have different banks like Chase, Capital One, Amex, or if you just have one, you can track it there.

38:23If you want it simple, stay with one bank, makes it easy, right? But I recommend Chase, Capital One, Amex. and then for bonuses, offers, all that, card pointers. It's an app that you can go download. We've had, we just actually released our podcast episode with Brooke, who's a director of marketing there. She does a live demo, kind of explains that on our podcast. So if you wanna listen to that, go check that out. It's really helpful. And then a word wallet we have coming on as well. So those are just two simple tools to track. And then obviously you have your different bank apps, but yeah, it can get overwhelming.

38:59at first. So I think it's always just like figure out again, what's your budget? What do you feel comfortable using it on? And if you just want one simple solution, that's totally fine. Don't, again, like real estate, don't go down the rabbit hole on Reddit and shiny card object syndrome, because you will dive into the hobby very deep. But I think it's always, again, going back to what's most important to you and what's going to fit your lifestyle the best.

39:24Tony Robinson:Ross, one follow-up question for me, because sometimes we work with, as real estate investors, we work with vendors who maybe don't invoice, you know, and maybe you're paying them from Zelle or Venmo or whatever it may be. And obviously I can't use Zelle and use a credit card. Do you have a solution for folks that maybe aren't from a vendor perspective, aren't sending invoices? Yeah. So we have a product integration with a company called Melio. So they, you can actually, so from a business standpoint, you can utilize that. If you aren't, if you don't have an LLC or if you're doing it from a personal standpoint, there's one called Plastique.

40:01It's with a Q at the end. And that's actually a couple of guys from Amex who created that one. But you can pay if you're just doing like a personal home for that. Like, so the example that I use when my wife and I repaint our house, we use Plastique. If I have any, just say something goes down with a boat or something that's personal, use Plastique. Melio for anything else on the business side. And you get hit with a 2.9 % fee. But at the end of the day, if I'm looking at that fee, the example that I used for the 100 ,000 chase points to business class, right? I'm getting five, six, seven times my points.

40:39I'm not worried about that fee, right? And if you're a business owner, that fee can be written off. So that's just another tax strategy that you can utilize. And for people who are doing more real estate investing, like we work with clients who there's developers who have materials, labor, right? a lot of that where their vendors may not take card. So if you're doing some of those flips, rehabs, like that's where there's big money. And I mean, I see people who are missing out on, you know, six figures, seven figures a year of doing that and just stepping in and making those minor shifts. You translate that into vacations for your family where you weren't getting rewarded at all.

41:17So it just comes down to asking the vendor or just figuring out what's the best way to go about this.

41:23Ashley Kerr:You know, I was wondering about that fee. I didn't know how much that would be as I haven't used either of those companies or heard of those websites before. So I'm definitely going to check that out. But like you think about it in like almost on any other payment platform, you're paying a fee anyways. Like I pay a lot of my contractors through like a payroll. It's like gusto, but you can do 1099. And like, I'm getting charged a fee anyways. Like I have to pay a monthly fee anyways to them to do that. The way I pay my cleaners, I just found this out yesterday. I've only been paying them through this one software for two weeks.

42:00Ashley Kerr:So it hasn't gone through a full month yet. It's like a 7 % fee they're charging me to pay my cleaners through this. And I'm like, okay, I got to figure out if this is worth the convenience that it offers or change it to something else. But it's like that 2.9 % doesn't sound that bad. I mean, how many people actually pay with cash for anything anymore. They're paying that fee anyways with markups that people do at different, you know, restaurants or retail, things like that. So everywhere you're getting charged. Yeah. And there's, yeah, you'd be surprised how much, how many dollars sometimes are being missed.

42:37But Ashley, to your point, if you spend more and you're an established flipper or developer, um, and you're starting to do more of that and you're spending over thresholds of, let's just say a million, we partner with Melio and have specific product integrations that you can then negotiate that rate down, right? If they know you're funneling in a ton of money, right? You, right. We have the connections that we can make and say, Hey, this person's spending, they're getting business. They're going to happily do that. And then also there's some strategies too, where sometimes if you're already paying via ACH, you could say, Hey, I'm going to pay it with a card.

43:12And then you could also then go back to them and say, well, well, you know what, maybe I want to pay with ACH. Could you just take that 3 % fee off? And then if they cut that 3 % fee, go to Emilio or Plastique, pay it. You're coming out net even and you're getting six figures or however much you're spending on points. So there's different creative solutions that you can do. Everything's negotiable as you guys know.

43:33Ashley Kerr:I think another point to hit on this too is if you're going to take the vacation anyways, you're going to spend that money anyways, but why not get it way discounted paying that 2.9 % for getting at least minimum a thousand dollars if you get the 100k bonus points plus whatever you spent to get that you get those points on top of the the hundred thousand so uh yeah i love credit card travel hacking and my family has been able to do a lot more travel than i ever imagined

44:05Tony Robinson:because i am definitely not as advanced as you are uh ashton it comes to the travel points and And as we're talking, I'm like kicking myself because my wife and I, we renovated a hotel last year and we probably spent 350K or so renovating the hotel. And we did it all with a debit card. And part of it was because it was a partnership. There were multiple people involved and we had this new LLC that we had set up and there wasn't a credit card for this new LLC with all these partners. So like, hey, let's just put it all into the bank account. We'll swipe it that way. And afterwards, it's like, man, I should have just like used my own credit card and reimburse myself, you know, but I guess, Ross, let me, let me ask, right?

44:40Tony Robinson:Like you have a partner on some of these deals. So how do you guys split the points? Like, what do you get? What do you guys do with the points if it's a partnership? Yeah. So at the end of the year, we just split them down the middle. So you're able to, so like for Chase, for example, he's able to call them and say, Hey, I want to, you know, send these to Ross Alcorn since that's a, that's a business unlimited ink. If you have a Chase Sapphire preferred or reserve, you can connect those and send those points to that other person.

45:10Ashley Kerr:As long as they're like a member of the LLC. Exactly. So I'm an authorized user on that card. So he opened the card and that's a strategy too is have one person open the card and then you can start to strategically align because there's things with, and we're going down a rabbit hole here, but with Chase, there's something called 524 where if you've opened five personal cards within 24 months, they won't allow you to, and that's for Chase only, they won't allow you to open another card. So when you start to get into the points game, you kind of want to figure out like, hey, Chase is my bank that they give 0 % interest cards.

45:46They have the best transferable points. Like, make sure you're doing that. That's I've been solely focused on that. Now I'm getting more into other ones. But like those are some things. And you can do the same thing with Capital One and Amex. So like when partners, right, we have, you know, developers, you know, flippers, people that have partners. And at the end of the year, they say, hey, Ross, we want to go on a vacation. whether that's a quarterly retreat, whether that's end of year, or we want to just take our families, right? Maybe it's not together. How do we mix, you know, how do we get those points to each partner?

46:18There's ways to strategically do that with people on those. So that's, you know, that's a little bit more advanced, but that's another strategy. So there are ways to split it where it's not like partner one gets card. All right, Ross, you're screwed. You don't get any points, right?

46:35Ashley Kerr:my partner I'm the one that times it up I'm the one that does the people I just have before we wrap up Tony I have one more like quick thing real quick is that I think that old strategy also works really well where you can like divvy up the points it's like say you know I'm my partner and I like I have Hyatt status or something where like maybe he can take the the Hyatt points and then transfer them to me if it's like our mutual credit card but he was the main person that opened it, but like I have the, you know, the benefits or whatever that I could book in stuff too. So, and that's what's nice too.

47:10If you're doing a partnership with someone that you're friends with and you like to take those vacations, like we get to benefit from those. We got to go to Greece last year, right? We get, we got to go celebrate like next year. We want to do Turks and Caicos for our 35th birthday together. So it's like, those are the type of things, right? Where it's not just like, Oh, we're getting the best deal. We're credit card hacking. It's like, no, They create actual cool memories. And actually, like you said, you're flying business class live flat to and from Europe.

47:34Ashley Kerr:Yeah, my kids don't know yet. So it's going to be a surprise to them.

47:39Tony Robinson:I think the business idea, Ash, that we need to go out and execute on is just how can we get all the people that we know that do renovations to use our credit cards? And then they just pay us the cash and we get all the points for their transactions. If we can figure that out, then we're set for life.

47:52Ashley Kerr:I was just going to say, why don't you buy another hotel? I'll open a credit card in my name and you can just use the credit card. I'll get you a nice big credit limit spend on that credit card and you go ahead and use it. And I'll be like a private money lender. There you go. If you guys need and if you guys need business bankers to up the credit limits, let me know because I work directly with those and they can get those. Well, Ross, thank you so much for coming on today. We loved talking about your journey, your experience and the credit card hacking. where can people find you and reach out to you?

48:25Yeah. So you can just find me at itineraryboss.com. All my social medias, itineraryboss. And then we actually have a free points and miles cheat sheet. That's going to get you right. How to start earning points, how to start redeeming, maximizing. And then it also comes with a transfer partner cheat sheet, which shows you how to transfer those chase Amex capital one points. And then it also has a multiplier where it really just breaks down each of the cards and you can decide which one's right for you. So we make it super simple. That way you can go do that. And yeah, itinerary boss. And if you want to connect, that's where you can find me.

48:59Thanks so much for having me, Ashley and Tony. It's been great.

49:02Ashley Kerr:Yeah. Thank you, Ross. I'm Ashley. He's Tony. And we'll catch you guys on the next episode of Real Estate Rookie.

49:08Tony Robinson: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. Even if you've done one deal, your story could help inspire the next listener.

49:26Ashley Kerr: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.

49:39Tony Robinson: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. I'm Glenn Washington, host of Snap Judgment, the award-winning storytelling podcast from KQED. And every week, Snap deals a new card, like jumping on Rihanna's private plane, or the accidental bank robber, or even the man who was swallowed by a hippo. What? Pick a card. Any card. Tap to listen now to Snap Judgment from KQED on Spotify.

From the publisher

Most rookies buy rental properties for monthly cash flow or long-term appreciation, but for today’s guest, the enormous tax benefits were the biggest driver. Whether you’re looking to achieve true financial freedom, leave your W-2 job, or keep more of your hard-earned money from the tax man, this episode is for you!

Welcome back to the Real Estate Rookie podcast! Ross Alcorn was very good at his medical sales job, but he was slowly burning out. His breaking point? Paying over $175,000 in taxes (in one year!) and still getting hit with a surprise $33,000 tax bill. He knew there had to be a better way to not only make a living but also build long-term wealth, and after a few conversations, he plunged headfirst into real estate investing—taking down five deals in just six years!

In this episode, you’ll learn how real estate tax benefits often outweigh cash flow, appreciation, and loan paydown in many cases—especially if you’re a high-income earner or full-time investor. But that’s not all. Stick around, and Ross will also share the real estate side hustle he uses to furnish and renovate his rentals and travel for free!

In This Episode We Cover

How Ross went from job burnout to building a five-property portfolio

How to potentially save thousands on taxes with rental properties

The real estate side hustle that could help pay for your next vacation

The biggest keys to a successful real estate investing partnership

How to drastically reduce your living expenses with the house hacking strategy

And So Much More!

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