3 Reasons Why You Haven’t Bought Your First Rental Property (Yet)

Ashley:
Most rockies believe there’s a moment coming when they’ll finally feel ready to buy a deal. When the market makes sense, the numbers feel safer and the fear goes away.

Tony:
But the truth is that moments almost never comes. And in 2026, that belief alone is the biggest reason most rookies will stay stuck on the sidelines.

Ashley:
This is the Real Estate Rookie Podcast, and I’m Ashley Kehr.

Tony:
And I’m Tony J. Robinson, and today we’re going to break down the reasons why most rookies will not buy a deal in 2026. And as we go through these reasons, we’re also going to call out how you can be the exception. So if you hear yourself being echoed in some of these points, don’t worry, we’ll try and show you how to fix it as well. All right? So the first reason that you probably won’t buy a deal in 2026 is because you’re confusing comfort with confidence. And we’ve talked about this in the podcast before, but oftentimes rookie investors want to feel comfortable with the idea of buying their first rental. They want this comfort when they submit the offer. They want this comfort when they sign the closing docs. They want this comfort when they welcome in their first tenant or their guests or their first flip or whatever it may be.
But here’s the truth, guys. It is physically impossible to be comfortable and to be growing at the same time because by definition, growth only happens when you’re stepping outside of whatever comfort zone you currently exist in. So if you’re waiting for this moment of this comfort to appear in order to do this thing you’ve never done, you’ll get stuck in this endless loop where you never actually take action. Now, confidence on the other hand is something that you can build towards. The more deals that you underwrite, the more people that you talk to who’ve already successfully done the thing you’re trying to do, the more agents you talk with, the more property managers, the more general contractors, the more data points you have to support your decision, that’s how you build confidence. So that’s the first one for me. Stop confusing comfort with confidence. Focus on confidence, not comfort.

Ashley:
A big part of this I think people don’t look at is you go to a W2 job most likely every single day and you feel safe. You feel comfortable taking on a job and that provides you that comfort. And going into real estate and buying a property feels uncomfortable. It feels like a risk. You have to look at the differences of these because you feel comfortable in your job, but you could literally be fired at any moment, any day and lose your income. But yet people see a job as they’re comfortable with that, but somehow real estate and buying a property is a bigger risk and has greater potential to fail. But if you look at the two different scenarios, having a W2 job is really not that safe at all. Where if you’re buying an investment property, you have more control over that asset and more options as to how you can actually make it profitable, make it an opportunity for yourself than your own W2 job in most cases.
So I think having that control piece is a big difference of being able to lessen your risk and to provide an opportunity for yourself that you can control and not your boss or the owner of your company that is controlling your future.

Tony:
And what this costs you when you’re stuck in this loop of trying to feel comfortable before you take action is that you never actually get the reps in that build the confidence. The only way that you build confidence is by getting the reps in, using the data that’s in front of you to actually get the reps in. So I always tell folks, it’s like the first glass ceiling you have to break through is submitting that first offer. And I would encourage every single person who’s listening today to just go submit an offer on something and just make it an incredibly low, almost insulting offer because the goal isn’t that you actually get the offer accepted. The goal is that you stop being afraid of submitting an offer. So when you get stuck on comfort versus confidence, you lose that ability to get your reps in.
But in terms of how you can be the exception, the first thing is to take action before comfort shows up. Just walk into this knowing that it’s going to feel a little uneasy. You’re going to be second guessing yourself a little bit. You’re going to be like, “Am I doing this right?” Now, I’m not telling you to jump in ill-equipped or unprepared, right? Still do all the work you need to do to feel that you’re taking the right next step, but just know it’s going to feel a little uneasy. It’s going to feel a little maybe nauseous as you submit that first offer. And then I think the next piece is to define the one uncomfortable action that you’ll take. Already talked about submitting the offer. I think that’s a great big one to take. But even before that, simple things like picking up the phone and talking to agents.
How many agents can you talk to to help you get to your first deal is a great thing to do. How many general contractors and quotes can you get for a potential property that you’re looking at? The more action you take, the easier it becomes to take that next step. And I think if we measure our progress based on the actions that we’re taking, not necessarily whether or not the deal is done, that’s how we make sure that we’re making progress over time. So that’s the first one. Stop confusing comfort with confidence.

Ashley:
Comfort actually keeps most rookies from starting, but next we’ll break down why chasing good deals keeps them from ever finishing. We’ll be right back after a word from our show sponsors. Okay. Welcome back. So once rookies push past comfort, the next trap looks productive, but still prevents buying. So let’s get into why you won’t buy a deal. And that reason is because you’re waiting for a deal to just fall into your lap without actually going out and finding a deal. And I’ve definitely been guilty of this myself. Even over the years, I’ll just sit and think, “You know what? I’m not going to chase a deal. Maybe I’ll get one this year or something.” But I think that if I really, really want to find a deal, I have to go out and I have to put in the work. I have to put in the effort of finding the deal and not just scrolling the MLS waiting for the perfect deal to appear to me.

Tony:
Yeah. You can’t manifest a good deal into your life. You can’t positive think your way into a deal.You’ve got to actually do some work. And our good friend, James Danar from the On the Market podcast always talks about deals aren’t found, but they’re built or they’re made or he phrased them in a certain way, but it’s like basically you have to go out there and manufacture the right deal. And for him, what he talks about a lot of times is, “Okay, what does a business plan look like on this deal that would allow me to turn into a good deal?” So maybe I’m buying it as a three bedroom, but I’m converting it to a five bedroom, and that’s how I make this deal work. We’ve interviewed Laka Davetha and she’s built an incredible portfolio in the Seattle area, but what she’s focused on a lot recently are ADUs.
And for her, it’s like, “Hey, I can go out here and buy a single family home and maybe it doesn’t work that way, but if I do a detached ADU, that completely changes the economics on this deal. And now I’ve got two properties for the price of one, which allows me to go out there and generate more revenue.” The Nawsums, Shannon and Christian, who we interviewed in the podcast, they do room rentals and they’ll go out and buy a three bedroom home and convert it to a seven bedroom home and then they’re renting to students. So it works for their business model. So I think we’ve got to get out of the idea of just, I’m going to look on Redfin or Zillow and that’s where I’m going to find the perfect deal, but it’s how can I maybe get a little bit more creative?
How can I put a little bit more work? How can I view this from a slightly different angle to try and find the right approach for me that allows me to get a good deal?

Ashley:
And I think even before that, if you’re waiting for the right deal to fall into your lap, do you even know what the perfect deal is? Do you even know what deal you want to fall into your lap? Have you defined your buy box? Do you know exactly what strategy you’re going to do? And that will really help you narrow down your focus and be able to actively go after what you’re looking for instead of just waiting and looking and like, “Oh, you know what, that doesn’t look great. No, not that, not that. ” And waiting for what’s going to be perfect for you, I think really defining what is the deal that you’re looking for first and then trying to actively go and search for that. And it’ll be easier to search for it if you actually know what you’re looking for too.

Tony:
Now, Ash, you make a great point. And two things I’d add to that. Number one is that if you’re just waiting for an agent to send you good deals, it’s not that that approach won’t work at all, but it is that that approach is going to be a significantly slower route toward finding your first deal. Of all the properties in my portfolio, I think maybe my first, the very first one that I bought, I think might be the only one that an agent actually sent to me where they were like, “Hey, here’s one that kind of pops up that meets your buy box and your criteria. Here’s where I think we should submit our offer,” so on and so forth. Every other deal has been me out there searching, hunting, underwriting, analyzing, and then going back to my agent saying, “Hey, here’s my offer. Here’s what I’m thinking.
What are your thoughts? Cool, you’re on the same page. All right, let’s move forward.” So I think first you’ve got to change the role that your agent is playing to more of an advisor than your straight deal finder.

Ashley:
It’s just a bonus if you get a deal brought to you. I’ve gotten a ton of deals from word of mouth referrals. “Oh, my cousin’s selling a property. Let me give you their number. I know they want to get rid of it. “Those should just be bonuses and you shouldn’t depend on the agent bringing you deals or the word of mouth deals or referrals from other people to lock in a deal.

Tony:
And I think the second piece to your point, Ashley, of you won’t know what to look for until you start taking some of this action. One of my strong recommendations for folks is that before you even start hunting for a deal to purchase, first do the research on what’s already working well in your market. And this can apply to long-term rentals, short-term rentals, midterm rentals flipping, but let’s say that I’m a flipper. I can use Zillow, I can use Redfin. There are websites like PropStream or Privy where you can make the search a little bit easier, but I can go back and find properties that have recently been flipped in the market that I’m looking at and I can very quickly start to identify, okay, well, where are the areas where the majority of the flips are happening? So then I can go from an entire city or an entire county, maybe down to a specific zip code or certain blocks within those cities that actually work well.
Then I can start to see, okay, well, what are the bedroom counts and kind of square footage ranges that are usually moving the fastest? And then I can say, okay, well, maybe the one bedrooms don’t sell all that well. Or man, if I get below 1000 square feet, those tend to sit a bit longer. But if I’ve got a good starter home, three bedrooms, two baths, even up to four bedrooms, those tend to move pretty quickly. But man, if I start trying to sell like a five or a six bedroom, those tend to settle a bit longer as well. So you can start to engineer what your buy box looks like by simply looking at the data of what’s already been successful in your market, and then that gives you a better sense of, okay, now what do I need to go look for in this market to be successful?
So if you’re trying to find deals, one of the best places to start is by looking at what’s already sold in your market. I think an additional point to add to this too, Ash, is that as you start to do the work of actually sourcing the deals, one of the other points that you should be focused on is better understanding the seller. And I think that’s where a lot of Ricky investors also get caught up is that they see the list price for a property and they take that as gospel, right? It’s like that seller is only willing to accept that list price. And I was just talking to someone yesterday who’s looking to buy their first Airbnb and he was looking at a pretty expensive property in upstate New York. I think it was listed for like $1.69 million and the deal worked for him at like 1.3.
So there’s like a $300,000 gap, which is not a small amount of money, but the property had been listed for the better part of a year. So this guy who’s looking to sell this property has been sitting on a $1.7 million property for over a year and it’s just been sitting empty and he has been renting it during that time. So for me, it’s like, hey, there might be some motivation for this seller to actually budge off of that 1.7 purchase price. But the guy who I was talking to was like, “Man, I just don’t want to offend this seller.” And what I shared with him was I would be more concerned about locking up a property at the wrong price than I would be about offending the seller. So I said, “Man, just submit the offer, whatever number makes the most sense for you.
” So he went to the agent, his starting number was 1.2 million, and the agent came back and said, “Hey, look, it’s listed at 1.7. I know the seller will probably come down to 1.5. 1.2 might be too much of a stretch.” But even there, we went from 1.7 to 1.5 with one quick conversation. So I think the biggest thing for rookies to understand is that you’ve got to put the ball in the court of the seller to either accept, reject, or alter whatever offer you’ve submitted to them, but don’t try and get in their head and make that decision for them. So I think that’s one important point when it comes to finding the right deal.

Ashley:
I think too, if you don’t know this person personally, if you offend them, will you ever talk to them or meet them again or even think about them again? In most cases, no. Okay, you offended someone, you will never interact with them again because they’re not selling your house, you’re not buying it and you move on to the next deal. But if they negotiate with you or they bring it down, now you’ve got yourself a deal. Trust me, I’m the worst person to ask about confrontation, but even that, I am okay with

Tony:
It. But Ashley, let me even ask you, let’s say that you were selling that property for 1.7 and someone came and offered you 900K, would you even respond to that offer?

Ashley:
Yeah, I would at least counter offer. I would at least do a counter if I would say the 1.5 or whatever, I would at least counter and say that’s the lowest I’m willing to go.

Tony:
And what if they came back after you countered it at 1.5 and they’re like, “You know what, Ashley, since you countered me, I’m actually going to reduce my price to 500K.” What would you say next?

Ashley:
Then I probably would just tell my agent, either don’t respond or … So

Tony:
At that point, you might be considered insulted by their offer, right? Let’s say that same seller came back to you and they’re like, “You know what, Ashley? I have some time to reflect. I realized I was wrong for that offer of 500K. I want to now offer you a full price offer at 1.7.” Would you be okay with that? What would you say to that?

Ashley:
Yeah, especially if this is an investment property, I don’t care who I’m selling it to. Even my own house, I don’t care who’s buying it or what you’re going to do to it. Yes, someone that’s lived into their house and taken care of it and built beautiful gardens and everything, and then maybe they want to drive by once a week and make sure everything’s wonderful, wants to sell it to a family and blah, blah, blah and stuff like that. But as an investor, I do not care what you do with the property after you’ve written me a check.

Tony:
And I think that’s the scenario or that’s the mindset for a lot of people. And that’s why I went through that little thought exercise because it’s like, even if you offend a seller with your first offer, there’s usually some number where that offer is no longer offensive. You’ve just got to figure out if you can get as close to that number without going over where the deal makes sense for you.

Ashley:
And one thing too is follow up with them. So you do your low ball offer, whatever, they don’t respond or they get mad, whatever happens. Three months later, follow up and ask their agent or would they be willing to come down anymore or what’s going on with the deal? Follow up. There’s probably been two circumstances I can think off the top of my head where I’ve put offers on a property, they said no, and six months later it closed for less than what I had originally offered. But I don’t know if it’s either just them thinking I’m not interested anymore because it’s been so long or them if they really were insulted and didn’t want me to buy it because of my first offer, but yet they sold it because of that. But I think continue to follow up. Even if you do insult the person and they’re mad, continue that follow up with them or their agent at least with your agent or something like that.

Tony:
And I get why so many Ricky investors are worried about quote unquote insulting the seller, but guys, just know if you come back with a better offer, that insult, it usually goes away pretty quickly, right? So understanding the seller, trying to get a better understanding of their pain points. One other piece on that too, Ash, and we’ve interviewed a lot of folks who have talked about this. You mentioned that the seller who wants to drive by and see their garden every time. And it’s because we’ve interviewed folks who’ve gotten incredibly great deals because they offered something that seemed super insignificant to you as the buyer, but was very significant to the person who was selling it. We’ve interviewed folks who have gotten big discounts because they helped the seller move. They’re like, “Hey, I’ll get a moving truck for you so you don’t have to worry about moving everything out.
” We just interviewed someone who got a deal because they promised to take care of the garden that this little old lady had been cultivating in her backyard. So there are so many, like Ash, even you, you said one of your deals, you promised the seller that you would keep one of the tenants in place because she had been there for so long. So every seller has a different motivation and the better you can understand what’s important to them, the better offer you can craft that’s not even related to the price of the property that might allow you to actually close on that deal. So we could probably do an entire episode just in negotiating with sellers and understanding motivations, but just now high level, super important to focus on.

Ashley:
BiggerPockets also has a great book for negotiating deals written by J. Scott, and you can find that in the bigger pockets of bookstore. Last

Tony:
Piece I’ll hit on this point here is it’s also important to understand the different financing options that are available to you as you look to buy, because that can also have an impact on the offers and the deals you can actually close on. If Ashley and I are both looking at the same exact property, but Ash has just gone to Bank of America to get her debt and they’re like, “Hey, Ashley, we need 30% down on this deal.” And I go to my local credit union or I go to 20 different credit unions and they’re like, “You know what, Tony? Actually, if you get this deal and you invest another 50K into the rehab, we think it’ll be worth a lot more once it’s done. We’ll fund the whole thing You just got to go out there and find the deal.” Same exact property, but very different loan products is going to allow me to execute in a way that Ashley wouldn’t be able to execute on.
So one of the biggest mistakes that we see rookies make that gets them stuck on the sideline is going to one bank or one lender and thinking that that person has all of the potential loan products that are available to you as you look to go buy this deal. So shop around more, try and get more options in terms of loan products, focus on those small, local, regional banks who have more flexibility when it comes to financing investment properties, and then pick the right one that matches for the specific deal that you’re looking at. All right. So even knowing how deals work isn’t enough. And right after the break, we’re going to talk about why learning still isn’t translating into action. We’ll be right back after this. All right. So at this stage, the problem isn’t information, it’s execution. So the final reason why most rookies won’t buy a deal in 2026 is because you get stuck learning and you never start executing.
And this part is, it’s a sticky, kind of slippery slope because learning feels super productive. You’re listening to the Real Estate Rookie Podcast, you’re watching YouTube videos, you’re saving random little clips on social media. All of this feels important and it feels like you’re making progress, but the thing is that learning doesn’t actually carry any risk. There’s zero risk associated with listening to a podcast or watching a YouTube video or saving things on social media. Without clear deadlines or stakes, education just can kind of turn into a delay. I met someone a few days ago who had been thinking about buying an Airbnb and her and her husband had been thinking about it for over two years. And while I committed them for like, “Okay, hey, it’s great that you took your time to educate yourself.” There’s not that much. It should take you 24 months to actually jump in and take action.
So you’ve got to figure out how do you make sure that the accumulation of knowledge doesn’t lead to in action. And what I typically share with folks is that if you get to a point where you’re listening to the Real Estate Rookie podcast or whatever the podcast you listen to and you’re reading the different books and you start to realize that you already know the majority of what we’re discussing, you know the terms, the frameworks, BER, you know ARV, you know this, you know that. You’re like, “Hey, Tony, I know. I’m supposed to go talk to the local banks as well. Hey, yeah, I know I’m supposed to submit an offer that’s going to be a little bit lower than what I’m comfortable.” If you know all of those things, then that’s a really, really good sign that you’ve already absorbed enough knowledge and now it’s time to step into actually taking action.

Ashley:
If I was a doctor, I would diagnose you with analysis paralysis. And I think this is just a huge thing. You want to feel back to the beginning of this episode, you want to feel comfortable and confident and you think that the more you learn and the more knowledge you have, the better you feel. Think about it. You go to school and study for how many years just to get your first job and so you feel confident and ready. You’ve got all of this schooling, all of this studying under your belt and now you’re ready to do the job. And I think in real estate that can be detrimental to you sometimes. Yes, I’m not saying go ahead and just jump into it without knowing anything, but you don’t need to have four years of schooling to understand how to purchase a property and to operate it as a rental.
And I think that’s where most people get confused is that they need to absorb all of this knowledge. They need to know everything, but you don’t. You can think about the people who become accidental landlords. Think about the people who are going through some kind of significant life impact that is detrimental to them, but they’re still being able to buy a rental property. Think about somebody who didn’t even go to college fresh out of high school, bought their first house hack. Think about the people that are being able to do this without spending years and years doing research or thinking about it. And you are probably already ahead of most people that get started by having two years to talk about it, by having two years to absorb knowledge to learn. Think about if you bought a property two years ago, how much farther you would be ahead, how much equity that property would have accumulated, how much experience you would have already obtained.
So as you listen, especially when we have the rookies on and to some of the obstacles and the hurdles that they have overcome to do this, a lot of you listening are probably in a way better position to actually start because of maybe time, money, the knowledge you have already absorbed. And I think a big telltale sign is if you go into the BiggerPockets Forums, you can answer a question, a couple questions, because you know the answer, you’re already a lot farther ahead than other rookies too.

Tony:
And I think the first step is usually the hardest. And it’s this very common thing that we see amongst the folks that we interview and just the people that we meet in life that the first deal, like from the time you commit to actually closing that first deal, somewhere between a year to 24 months is pretty common, but that second deal never takes as long as the first deal. And that’s because once you get that first deal done, everything else becomes so much easier. So just know that the first step is usually the hardest. So if you want to be the exception here on this last reason that most rookies won’t buy a deal, here’s the one challenge. Set a goal on the number of deals that you’ll analyze in 2026 and the number of offers that you’ll submit in 2026. And if you just work really, really hard to hit those two things, chances are you’ll end up finding at least a few deals that are good enough for you to really want to move forward with.
So how many deals are you analyzing? How many offers are you submitting? And the goal is that you can use both of those actions to get you to your first deal.

Ashley:
Well, thank you guys so much for listening to this episode of Real Estate Rookie. I’m Ashley, he’s Tony, and we’ll catch you guys on the next one.