How to Start Your Rental Portfolio in 2027 (No Experience, Little Money)

Ashley:
If you want to start building a real estate portfolio in 2027, watch this.

Tony:
We’ve interviewed hundreds of real estate investors and have scaled our own portfolios to replace our incomes. Now we’re financially free. So what would we do if we were starting over in 2027 with little money and no experience, which is exactly how we started initially.

Ashley:
We’re about to share exactly what we do starting on day one to not only buy rentals and start building our portfolios, but what we would do to do it way faster and smarter than we did it when we first started.

Tony:
So this episode will be split into three main parts. The initial setup, which is just getting you ready to buy your first rental, the strategy, how to buy your first rental in 2027, and then the streamlining. So how do we make a system so you can scale even smarter?

Ashley:
If you are serious about building wealth through real estate, replacing your income with rentals, or being the first in your family to kickstart generational wealth, we’re sharing how to do it starting in 2023. So let’s start with the setup. There’s things that you have to do before you can actually buy your first property. And I think one of those things is to actually submerse yourself into the world of investing by not working with people who are actually doing it.

Tony:
Yeah. So step one is just getting into the right rooms with the right people. And we’ve talked on other episodes before where part of the challenge of being a rookie investor is that you’re by yourself. And chances are you’re probably not listening to this podcast episode in a group setting with five of your closest friends.

Ashley:
And if you are, that’s so cool.

Tony:
That’s fantastic. Let us know. We want to come to the listening party. But chances are you’re walking your dog or you’re at the gym or you’re on your way to work in the car by yourself. You’re consuming this content in a very kind of isolated setting. And I think sometimes while you’re building the knowledge base, you’re not yet building the confidence because you haven’t actually met a lot of people in real life who have done this themselves. So if you can get into the right rooms with people who are one step ahead of you, who you can shake their hands and say, “Hey, tell me your story,” that builds the confidence in your ability to replicate what they’ve done. So just getting into the right rooms, local real estate meetups, BiggerPockets, the RBPCon conference, just getting into the right rooms with the right people.

Ashley:
But I think it’s also important to not just attend and see what will happen or who you will meet. Actually go to these meetups, attend these events with intention, as in what are you bringing to the table? What can you share? And if you literally feel like that’s nothing, what is your current job? What are you currently doing? That’s something you could share with someone. But what do you want to learn about? What do you want to get out of the meeting? Do you just want to meet people? Do you want to understand something you don’t know about real estate investing? A lot of good meetups, the very beginning of the meetup or when it starts, they’ll have some kind of open forum where you could… Sometimes everybody gets into a big circle and you say who you are, what you’re doing there and what you need from somebody.
So a lot of ways before you even start connecting with people as to you’re looking for a lender. Okay. Your goal at that meetup is to talk to as many lenders as possible about what you’re trying to do.

Tony:
And getting in the right room doesn’t necessarily just need to be in person either. I think that’s the goal is to get in person to get in real life, but you can also do it virtually, getting active in the Facebook groups, getting active in the BiggerPockets forums. If you don’t know, there is an entire forum ecosystem on BiggerPockets with a ton, a ton of great information from very, very experienced investors. So even if you can’t necessarily get in person often, at least invest the time, the effort, the energy to go find the digital place. If you want to join a paid community where other people are paying to be in the same room, it’s another great opportunity, but just find the place where other investors are congregating and get there, whether it be digitally or in person.

Ashley:
And if you want to find a meetup, you can go to biggerpockets.com/meetups. And I mentioned this as you want to be prepared going into these situations and you want to provide value also. You don’t want to be the person just asking everyone for help. So what can you do that will provide value for someone that… And you may be thinking, “I know nothing about real estate. This is my first time listening to this podcast. I know nothing. I have no value to bring.” And Tony knows I love to bring up this story. We were at a networking event for rookies and someone raised their hand and said, “I have no value. I have no experience. I’m just starting out as a rookie investor.” So he said, “Okay, what do you do for your job?” And he said, “I’m a project manager.” So Tony and I said, “Okay, everybody here who would love to have a partner that could manage the rehab project?” Almost every single hand shot up in that room.
And so I think there’s a lot of skills that you may have from past experiences, even from your childhood. Your dad’s a contractor, you walk job sites with him your whole childhood, but

Tony:
There’s – I though you were talking about how fast I could ride my bike as a kid, that might be somehow valuable as a real estate investor.

Ashley:
But take some of those things that, I guess, what can translate into real estate because there are so many skills that people already have that translate into this industry.

Tony:
And even aside from your skills in the workplace, oftentimes even if it’s just like how much time do you have on your hands? If you are someone who has an abundance of time, that in and of itself, even if you currently have zero skills, can you be the person that just walks over to the house that the flipper wants to bid on and you take photos of the exterior and the interior? Do you have an iPhone? Do you have a means of transportation? You got some free time? You can be of value. Can you run to Home Depot to pick up whatever materials they need picked up so that way the crew can keep working and be efficient? Then you can bring value. So even if your only value today is that you have some excess time and bandwidth in your life, that can be extremely valuable to the people who are maybe successful but lack time.

Ashley:
Yeah. And that also made me think of social skills. If somebody wants to partner with me and I will literally never have to talk to anyone, they’ll do every phone call, they’ll talk to every seller, they’ll talk to every vendor, contractor. You have those communication skills and you are extroverted and that is something you’re really good at is communication. That to me would be a huge benefit to being a partner for me. All

Tony:
Right. So just to recap, we had step one was just getting into the right rooms. Step two was just when you get into those rooms, you make those connections, bring as much value as you can. And then step three is just partnering up and learning. We actually just interviewed Vibov and Vibov had a story where he started off in single family rentals, graduated up into multifamily syndications, like larger multifamily properties. And the very first syndication that he did, he partnered with another experienced syndicator and he brought capital into that deal. He was like, “Hey, I’ll give you the cash, but I got to learn along the way.” And like, “Okay, sure, come along.” And from there, he did several more deals and now he quit his job and he’s doing syndications full time. So if you can simply partner with the people who have the skill sets, that is how you really started to build expertise in an area.
And I think it’s one of the best ways to really cut your teeth and give yourself the confidence to do it on your own.

Ashley:
So I actually, when I started in real estate investing, I took on a partner and that was the way that I started. I had a friend who had money and he was also interested in investing in real estate. And so we partnered fifty fifty on the deal. He brought the capital, I found the deal, I was going to manage it. And we also did it set up so that he also got his capital back in the form of basically a mortgage payment. So he got 50% equity, got 50% of the cash flow, but also he was getting his capital plus interest, five and a half percent interest back every single month on this deal. So it was a sweet deal for him, but also he was taking a lot of risks. This is my first time ever doing this. And so I definitely don’t do those types of partnerships anymore, but we still partner on stuff today.
So it ended up working out very well.

Tony:
Yeah. And I think that’s one of the elements of a partnership is one person has maybe the time, the other person has the capital. Okay, cool, let’s come together. Sometimes both of you have a little bit of capital and maybe by yourselves you can’t really do much, but together now you can do something. So I think it’s understanding what’s the value that each person can bring into that partnership. And we talk about partnerships a lot. So if you guys don’t know, Ashton actually wrote the book for BiggerPockets on partnerships. It’s called Real Estate Partnerships. And if you go to biggerpockets.com/partnerships, you guys can find the book. But in there we talk about the different ways you can bring value and the things you can do. And again, sometimes it’s money, sometimes it’s your sweat equity. We have deals where we didn’t bring capital, but we managed the properties.
And some of these we bought six years ago now. And our partners, all of their work was signing some loan docs and wiring in some funds and they carry the mortgage, which is a big responsibility. But when the guests can’t get into the property, when the washing machine breaks, when the cleaner calls out sick, when all those different things happen, our partners are dealing with those. We are, and we have been for the last six years. So it’s our sweat equity that allows us to really bring value to that partnership. So just there’s different ways you can position the partnership as well.

Ashley:
Okay. So what’s really important to you is being focused and you can’t focus until you’ve decided on a strategy. If you are looking at properties saying, “Ooh, this would be a good short-term rental, this would be a good long-term rental. Oh, maybe I should flip this house.” That is too broad. You need to narrow it down and you need to really get focused on what that strategy is going to be. And there’s multiple things to think about as to what strategy is best for you.

Tony:
We say this all the time, but guys, no matter what strategy you can flip. And even within the strategies, there’s different asset classes. We know people who flip traditional single family homes.That’s what most of us think about when we say the word flipping, but we’ve interviewed guests who flip mobile homes. We’ve had people who come in and they only flip condos. We’ve had people who flip small multifamily, large multifamily, self-storage. So you can flip anything. There’s people who focus on wholesaling. Again, you can wholesale a single family home, you can wholesale commercial, you can wholesale different things. You can do short-term, long-term, mid-term. There’s so many different mixes of strategies and asset classes that there’s many, many possibilities. And the truth is that there are people who make a ton of money in all of those strategies, and there are people who lose a ton of money in all of those strategies.
So one strategy versus the other is not necessarily better or worse. It’s which one am I more uniquely qualified to execute well? And would I be as good of a long-term rental landlord as Ashley? Probably not. Would she be as great of a short-term rental operator as me? Probably not. We have different skill sets, different things we focus on. Could we both potentially be successful in self-storage? Maybe. But the point is look at your unique personality, your unique skills, your unique character traits, and really trying to understand which strategy aligns best with who I am and what my resources are and what my goals are.

Ashley:
I’ll share mine. I worked for an investor who bought long-term rentals. I was his property manager. I had a huge advantage and a huge opportunity from having that experience. So that’s why, first of all, I had no idea there was all these other different strategies or things out there that you could do. So that’s why I started with that, because I had that advantage. It was a huge advantage to getting started. For you, short-term rentals, why do you think that was the best opportunity for you? And you didn’t start that way. You did try long-term rentals first, but what actually made you decide, why do you think in your situation that was the best strategy for you to pick and focus on?

Tony:
I mean, two things. It was goals, the goals that we had and it was skillset. So from a goals perspective, again, lost my job, needed big income and I needed it quickly, and traditional long-term rentals just weren’t going to solve that problem. So short-term rentals gave us that avenue. So from a goals perspective, very strong alignment. And then from a skillset perspective, my wife Sarah, who really kind of spearheaded the guest management side of things, she came from that kind of background, giving experiences to people. And she worked the green room at the late, late show and she worked the VIP suites at these celebrity events.That was her thing was giving people experiences. So between the two of us, it felt like a really natural fit. She wasn’t excited about the long-term rentals that we owned in Shreveport, Louisiana, but as soon as we got the first short-term, that’s when she got excited.

Ashley:
That’s so funny you say that because before I asked you that question, I was like, “Okay, I know what my advantage is.” And I was very curious as to what you were going to say your advantage was for short-term rentals because I could only think of Sarah. 100%. What did Tony bring to the table?

Tony:
Not a whole heck of a lot, honestly. I’m riding her coattails all the way and I’m not ashamed to admit. All right. So step number five guys is to find undervalued deals. And obviously easier said than done, Tony and Ashley, like duh, we all want good deals. But the truth really is that you make money when you buy. So we’ll talk a little bit about maybe the different strategies that we’ve used to find good deals and maybe even focus in on the strategies that we really focus on today and moving forward.

Ashley:
And we’ll also tell you about the properties that you could buy from us that are

Tony:
Undervalued. That really good deals. If anyone wants a good deal, I’ve got one for you. But I’ve leveraged, I think, a lot of different ways to find deals. Obviously, the easiest, most abundant way is just going on the MLS. And the MLS gets a bad rap in a lot of different places online because people are like, “Oh, MLS is where deals go to die.” We have, what episode number are we on? 780 something? We’ve had 780 different reasons to show why the MLS is still a great place to start. And a lot of the investors that we interview, they find good deals right on the MLS. Now, does it mean that it’s going to be easy to find those deals? No. Does it mean that what they initially listed it for is going to be the right property? No. Does it mean that the current condition of the property is going to be the end result?
No. But does it mean that you can actually find something? Yes, you can. I think about Ariel Herrera, if you guys go back into the archives, you can find her episode. But a big part of her strategy was she looked for properties. She had this tool that she built to help her do this, but she looked for properties where the square footage for the bedroom count was a certain percentage above the average square footage. And she knew that she found those properties that it would be easier for her to then add additional bedrooms. So she was basically buying a two bedroom that had the square footage of a three bedroom. And then her whole strategy was like, “Hey, let me just go and add a bedroom.” And she could immediately increase the value. The Nawsums who we’ve interviewed, they’re out of the Pacific Northwest, their whole strategy is, “Hey, let’s buy a five bedroom, get rid of the dining room and the living room and turn it into an eight bedroom.” And they did student rentals.
Students don’t need a formal dining room, so they got rid of that excess space to turn it into something that was more usable for them. A lot of those deals came right off the MLS. So depending on your strategy, you can go to the MLS and find a deal that actually works still.

Ashley:
And you can also buy our deals as… In my market, I’ll say this, is there are properties that are selling over asking, getting multiple offers, and they sit within a certain price range. They’re usually single family homes that families are looking to buy within a certain price range that don’t need a ton of work. If they do, maybe it’s just cosmetic stuff. Those are selling so fast. Small multifamily duplexes, they’re not traditionally selling that fast in my market. I just sold the duplex. I sold it in three days, but I listed it low. It was a good deal. I have another duplex that has been on the market for over a year. Went under contract six months, and finally the seller walked away after closing, or on closing day, they walked away from it. Then it was another month that we couldn’t list it again because we had to figure out the escrow, things like that.
But I think in every market, there’s probably a certain property type that is doing the same, that is selling right away, but also those are the ones that are not selling where they’re being listed, they’re sitting, and there’s investors like me that are willing to take a way lower price just to get rid of it.

Tony:
You mentioned some properties going over asking, some going under. We’re shopping for a new primary residence for a new home for ourselves right now, and there were two homes in our neighborhood. They were literally two doors down from each other. One of them, and they’re very similar in size, square footage, super similar. One of them listed at 899. The other one listed at 945. The one that listed at 899 ended up closing at 925, so that they went 25K over, and the one that listed at 945 closed at 915. So it’s like sometimes even if you just… My whole point is that you never know the motivation of the sellers, and just because someone listed at 945 doesn’t mean that’s the number they’re willing to take. And sometimes people do the inverse where they’re going to price low just to get the competition going. But the MLS is still very much a place that you can go to get deals.

Ashley:
And if you have no idea what that range is or what property type that is in your market, easy. Go to biggerpockets.com/agents, connect with an investor-friendly agent in your market who’s actually there to guide you through this information. The reason I know some of this stuff is literally because of my agent, that she’s the one that is selling me this information. And then of course I’m tracking Zillow like a crazy person looking at how many days something is pending. We just did an episode on AI, another thing I could probably have AI do instead of me manually going into Zillow and looking at all of this stuff. But yeah, go to biggerpockets.com/agent and you can find an agent that will actually help you with all of this if you don’t know for your market. And that can also help you build out your buy box.
Is there a property type that isn’t selling, isn’t sitting, because maybe there’s not a lot of people that are investing right now in buying those small multifamily properties. Maybe it is the single family homes. It’s the opposite in your market. Maybe there’s a price range or a rehab level that people aren’t taking on right now that maybe you can find a way to take advantage of that and put in those low ball offers and find those properties that are undervalued.

Tony:
Aside from the MLS, there’s other strategies. I’ve done direct mail. I’ve gotten deals that way where I’m mailing out postcards. I’ve worked with wholesalers and the entire goal of a wholesaler, the entire reason they exist is for them to do all the work, to hustle up and find these really great off-market deals, and then they go to you and they resell those deals to you for a small margin. So working with wholesalers. I feel like I’ve tried a lot of different things, but just pick the strategy that aligns, again, best with your skillset. If you’re someone who’s comfortable talking directly to sellers, like getting on the phone, then yeah, maybe take your shot at going to source your own deals, hand write letters. I’ve shared this on the podcast before, but when we were looking at long-term rentals in Louisiana, I had a very specific zip code that I was looking at, like a buy box.
It was pretty tight. I hand wrote, I don’t know, several hundred letters to this area and I dropped them all in the mail. I ended up getting a few calls back, but there was one lady who… Mary was her name, I never forget Mary, and she and her husband had built a portfolio in that town. They were looking to sell and they had, I don’t know, 20 houses or something like that they were looking to sell. At the time, the deal didn’t make sense to me because she was just asking a little bit too much and there was too much deferred maintenance. But I remember she ended up calling me two years later, two years later after I talked to her the first time and she’s like, “Hey, Tony, I think we can do your number now.” Two years later. Now at the time I’d already moved on to short-term rentals.
We weren’t really interested anymore and I was like, “Hey, thanks.” But you never know, even just one letter. She had 20 properties she was looking to sell, right? So you never know where even just writing a letter to a homeowner can take you.

Ashley:
Now the next step, so step six, would be actually streamlining your processes. So what does it look like for you to actually do a deal? So like Tony was just talking about, how are you going to source deals? Let’s implement that process. What does that look like? Are you going to be scrolling Zillow? Are you going to use AI to actually scroll Zillow for you? Because when you do these first deals, those systems and processes that you do can be repeatable for every deal after and after. And yeah, you’ll have to fine tune them and things like that, but if you can build out those systems and processes now, it is so much easier than when you’re onto deal five and now you have a portfolio to asset manage and maybe even property manage and to have to pause to put these systems and processes in place, it’s so much easier to actually document it and do it now, especially with AI too.

Tony:
Yeah, you hit the nail on the head because we both experienced that where we scaled super fast. We didn’t have the systems and processes in place, and then we both wanted to pull our hair out. And obviously I was the only one that was brave enough to do it and Ash still has her hair, but that’s what happens when you scale too fast, is that you put yourself in a position where things start breaking around you. So if you’ve got one deal, just document every part of that process. If it’s a long-term rental, okay, what do you do when you first get the keys? What does that checklist look like? For us in the short-term rental space, we have a, I think it’s like a 93 point Airbnb launch checklist that we run through for every property. And the reason that we built the checklist was because there was a lot of things we kept forgetting when we were setting up our properties.
We were like, wait, let’s just write down everything we need to do. So anytime we get a new deal, we know exactly the box we need to check. Whenever we have a cleaning at one of our properties, there’s a checklist that our team follows to make sure that we do all the right things. So focus on the high leverage activities in your business and just put a system that’s repeatable around each one of those, and you will thank yourself as your portfolio starts to grow that you did it early rather than later.

Ashley:
And there’s so much software out there that can help you with a lot of these systems. And if you’re a BiggerPockets Pro member, so if you’re doing a long-term rental, RentReady, you get RentReady for free as a BiggerPockets Pro member. You get to use Baseline for your banking and bookkeeping. It’s free that you can implement. Setting this all up now with property one makes it so much easier to implement these softwares for property two, three, four, five, six, because you already have it instead of that pause. Now I have to add five properties into RentReady, which still they make the onboarding easy for you, but it’s definitely way easier to do with property one. Also too, even estimating rehabs with being a Pro member, you get great pricing with Home Depot. Usually if a contractor would have to spend $100,000 per year to get this type of pricing, you can get that.
But what they have is a bid room and a quote room. So you basically build out a quote with all of your materials. I actually used to physically do this with a spreadsheet. Then I would go and add everything into my cart and then I would say, “Okay, this costs this much.” But now you can build that all into Home Depot. So you add your things to cart that you, okay, I need X amount of square footage for flooring. I need a faucet. I need a vanity. You add it all into there and then you now have a quote, a rough idea of what your cost will be for materials. And you also can save it all right in there so you know, okay, every time I’m doing a unit, I know that I’m using this paint color. I know that I’m using this flooring and I know what it’s going to cost me.
But then also too in Home Depot, you can take it a step further and actually submit it to them for bid where you can get even bigger discount, especially if you’re buying at bulk.

Tony:
And then the final step guys, step seven, is just helping other people. I think Ash and I both benefited tremendously from just giving away a lot of free content online. Even before the podcast, we were both giving away things on social media and just being present. The first time we ever property managed for someone, we didn’t do a ton of this, but the first short-term rental where we did third-party property management, it was someone who I met at a meetup and he was like, “Hey, Tony, you seem like a great guy. Do you want to manage this Airbnb?” I’ve had deals brought to me at meetups and places like that and people on my DM to send me things. It’s like if you just give, give, give, give, people reciprocate that and you become the person that’s top of mind for a lot of those opportunities.
So obviously I’m not saying that you need to go start a podcast, but even if you’re just a person who hosts a local meetup, what an easy way to build your network and give value to all of the other real estate investors and real estate interested people in your local city. You become that linchpin that connects everyone else. Great way to provide value.

Ashley:
Tony, you have a calculator, a short-term rental calculator you give out for free that people can download at realestaterobinsons.com.

Tony:
Realestaterobinsons.com/calculator.

Ashley:
Yeah. And then I have a little storefront with free downloads, so buy box, different things like that, acquisition checklist. So you can find that the link in my bio at wealthfromrentals on Instagram, but biggerpockets.com/resources. Us and other investors have made an incredible library of free resources that you can go to and download to that are all available to you to use, checklists, templates, calculators, different things like that to be able to use. So maybe there’s something you’re already doing, trying to find deals or understand your why, and you could post about that, you could share that, and that could help one other investor even. And then too, as you’re going about your journey, think about the people that are using the team that you’re building and referrals, your agent, refer your agent to other people, share your contractor with other people, share your lender with other people.
That is a huge way that I work with people is referrals. This lender was referred to me. The contractor referrals are a huge thing for me is that’s how I’m finding my contractors and working with them is referrals. I have another investor in Buffalo, and most of the time I am texting him and saying, “Hey, what contractors do you use for this?” He’s also a GC and an investor, and I rely on him to get a lot of my referrals, but he adds a lot of value to me from that.

Tony:
So guys, there’s always a question of is now the right time to buy real estate? There are some years where it’s easier, there are some years that it’s harder, but the answer to that question is always yes. Honestly, the best day to buy real estate was yesterday. The second best day is today. So the goal for our episode today was to simply give you a quick framework that you can use to give yourself confidence that you can actually do this, right? And while there are lots of people who are maybe screaming doom and gloom and saying like, “Oh man, interest rates are too high, inventory is too high,” whatever it may be, we don’t take advice from people who haven’t done the things that we want to do, right? So focus on the people who are actually doing it, who are living it, and take your advice from those folks.

Ashley:
Well, thank you guys so much for joining us today on this episode of Real Estate Rookie. If you’re not already, make sure you subscribe to our YouTube channel and you can follow us on Instagram @wealthfirmrentals and @TonyJRobinson. I’m Ashley, he’s Tony, and we’ll see you guys in the next episode.