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Ashley Kerr
If you've been learning about real estate investing for months or maybe even years, but you still haven't bought your first property, this one's for you.
Tony J. Robinson
Most rookies think they need more money or more experience, but sometimes you're already ready. You just don't realize it yet. Today we're breaking down the four clear signs that will tell you that it's time to buy your first rental property and what to fix if you're not quite there yet.
Ashley Kerr
So if you're stuck in analysis paralysis, this episode is for you. This is the Real Estate Rookie Pot podcast and I'm Ashley Kerr.
Tony J. Robinson
And I'm Tony J. Robinson. And with that, let's get into sign number one, that you are finally ready to buy your first real estate investment. So sign number one is that you have a strong personal finance foundation. I, I guess let's just define what we mean when we say financially ready. And we just interviewed Liz Carroll on a recent podcast episode. And, and it was a lot of that conversation was about the personal finance story behind your first real estate investment. So you guys can go back and listen to that episode if you want a deeper dive into this. But really what it means is that it's not necessarily about being debt free, right? Like, you know, I invested with student loan debt. I had my own primary mortgage, I had car debt. Like, I had just the debt that's kind of associated with living your life. But I was still financially ready to pull the trigger on my first investment because I had really good active income. I had money saved in the bank to cover my down payment of my closing costs and, you know, reserves and all those things. So the first piece is, are you financially ready? If you are living paycheck to paycheck and there's too much month at the end of your money and that happens every 30 days, then maybe it's a sign that, hey, let me get that fixed first before I jump into it. But again, if you can, on a very consistent basis, take care of all of your short term consumption, right? Like all the things, just keep your household running. You're saving for your long term, right. You know, you're saving for retirement. You know, you've got investments that are and stock market, whatever it may be, and you've got money set aside for maybe the medium term. You know, think emergency fund safety net. If you're checking all those boxes, there's a good chance that you are actually ready to get started.
Ashley Kerr
Yeah. Financial foundation. I a big thing that I always like to hit home is it's not about how much money you have. Like, we're talking about the surplus, you know, savings, things like that. It's about how you manage the money you do have. So living within your means, making sure all your debt payments are made on time. I think those are some of the mindset shift you need to have, is that you don't need to have a ton of money to get started in real estate. Yes, you want reserves and things like that. But what's more important is that you know how to manage your money. You know what's coming in and you know exactly what's going out and where it's actually going. What are those categories? And a favorite app that I love to use is Monarch Money. This is what I use. I link all of my accounts, my credit cards, my mortgage, my retirement accounts, my bank accounts, all linked in there. So I have one dashboard where I can go in and see, okay, where am I at every single day? And then it also categorizes my transactions. So I know how much I spent at the grocery store for the month, how much I spent going out and having an idea. Like if you're sitting there thinking, like, I don't know the exact amount and I don't want to go and look because it's probably going to terrify you and you're afraid to actually look at what the balance is in your bank account or how much you spent going out last month, then you definitely need to look.
Tony J. Robinson
That reminds me of me, like in my early 20s. You know, it's like you go out and you have a night out and you wake up the next morning like, oh my God, how much should I spend? So we don't want you guys living that life, but guys, there, there's really kind of three key things that you want to check to know if you're ready. So one, I already talked about it, but it's your. Your personal financial situation, right? So do you have money in the bank saved up to cover your own personal emergencies? You're saving maybe 401k in the stock market, whatever it may be. Does that box get checked? The second is, do you have money to cover your down payment, your closing costs for whatever property unit buying, and I guess maybe another piece to that second part is not only your down payment, but do you know how much you can get approved for? Like, are you in a position to actually get approved for a loan? And the third number is your reserves. Like, do you have enough in case things don't go according to plan? You buy the property on day one, you know your H Vac goes out, right. Or, you know, Ashley was always afraid of the roof blowing off. Like if you buy the property and then the next day the roof blows off, can you fix that? So if you can check all three of those boxes, then financially it feels like you're pretty darn ready. And I just want to also cover maybe some of the myths that rookies have when it comes to being financially ready. A lot of people say I'll buy when I make more money. And again, I think that's true to an extent. But once you've crossed a certain threshold, waiting is actually just working against you. There were a lot of people, I'll give you guys a real life example. We bought our primary home back in 2018. And since that time, the value of that home and we're in California, you know, have the appreciating market, the value of that home has gone up roughly $300,000 in seven years. Right. So a good amount of equity gain in that time frame. As we were shopping for our home, I was telling everyone that I knew. Like I had, you know, cousins in laws who were also in that phase of buying their homes. Like, guys, look, we're buying in this new construction subdivision. Prices are pretty reasonable for what we're buying. You guys should come by with us. And none of them listened to me. And they all ended up buying homes a few years after me. And now their mortgages are double what mine are for less home. And that's what happens when you wait too long, that the market can shift on you. So never try and time the market. Just look at where you're at right now and make do with what you have. And then the second thing that I think is a big Ricky myth is the amount you need to put down. Traditionally, yes, 20% is like the number that gets thrown, thrown around a lot. But you know, you don't necessarily need 20% if you're house hacking. You can get in for 0% if you've got a VA loan. NACA is the loan product that I've talked about a lot where you can get them for zero down. Fha, very low down option.
Ashley Kerr
The USDA loan too is zero down.
Tony J. Robinson
Ashley's favorite usda, which I didn't know existed until she became my co host, actually.
Ashley Kerr
Real quick as right now when this is being recorded, we're going through the government shutdown and they are actually going to stop funding USDA loans.
Tony J. Robinson
Interesting.
Ashley Kerr
Right now until the government starts back up. But I thought that was so Interesting, because I didn't like think of that as being a repercussion and it said for now, like VA loans, FHA loans are still going to go through, but they're stopping USDA loans.
Tony J. Robinson
Interesting, right? So yeah, I mean all the more reason guys, like if you were had the ability to get one six months ago, maybe you should have pulled the trigger. Right. I think the point is though is that there are a lot of options out there to help you buy your first property with low money down options. Even from an investment perspective, the 10% second home loan still exists and you have to use it personally for a percentage of the year to qualify for this. But it still exists. There are investor loans at 15% down and I know people who have used those loan products. So don't think you have to wait to get to 20% down to get that first deal.
Ashley Kerr
Now if you feel like you're financially ready or maybe you need to do a couple more things, here's a little action item list that you can do to get yourself ready. So first, building that financial foundation. Make sure you're living within your means and you know where your money is going, where it's coming in and out. Get an app to track it, use a spreadsheet, whatever works for you. Also, I want you to know what your credit score is. You can use credit Karma. You can actually each year pull your own credit report for free without having it ding your credit. Then you go to, you know, it's like a, it's not even a government website. So be very careful as you're like googling. It's like freecreditreport.com or something. But make sure it's actually the legit website. And don't put your Social Security number into the wrong website please. So you can pull your credit for free. You can see what's showing up on your credit card report. Make sure there's not some utility bill from eight years ago that's in collections that's sitting on there. That happened to a partner of mine when we tried to get a loan before. Know what your credit score is so you know you can actually get approved for a loan or if you need to do some work to actually rebuild your credit and then where is your down payment coming from or how are you funding the deal? You know, go get a pre approval. You can go ahead and you know, start building your savings. What's the amount that you actually need for reserves and a down payment too on the property. Okay. But even perfect finances won't help you if you're still stuck in in the research mode and analysis paralysis. Next we're going to talk about the moment you've officially learned enough to take action. And that's most of you guys listening right now. We'll be right back. In real estate, I used to juggle five different tools just to stay organized. One for leads, another for listings and a pile of sticky notes in between. It was chaos back then. I really wish I had today's sponsor, pipedrive, the number one CRM tool for small to medium businesses and real estate agents. Everything's in one place, from notes on listings to key information on leads, so I never miss a deal. Real estate teams using pipedrive can handle four times more inbound leads. It's a powerful, simple CRM built by salespeople for salespeople. With pipedrive, you're not just managing your sales, you're supercharging them right now. If you use my link pipedrive.com biggerpockets you'll get a 30 day free trial. No credit card or payment needed.
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Ashley Kerr
A R okay, the Dreaded Analysis paralysis. So we actually met someone at bpcon who came up to us and said they had been stuck in analysis paralysis. And each time we had some Guest on a rookie investor that talked about how they overcame it, it motivated them, gave them that oomph. Like, you know what? I do know enough. And one thing Tony and I always talk about is if you are listening to these episodes and you are already starting to know what some of this information is, is like, oh, yeah, I already knew that. I already knew that. I already knew that. Then you are ready to take action. So sign number two, you've learned enough to take imperfect action. If you've heard the majority of the lessons in this podcast, you're probably ready.
Tony J. Robinson
And I, we say this often, but it's like, to Ashley's point, if you're listening to the guest interviews or when Ash and I do the Rick applies, and you're like, I actually knew that already. Oh, you know, I. I knew that too. You know, I've. I remember that. And if you're saying that as you're listening to the podcast, that is a sign that you are ready. You can never get to the point where you know everything. Ash and I, to this day, we are still rookies compared to people who have been doing this for 20 years, and they're still rookies compared to people who've been doing it for 40, right? Like, we're all rookies in some sense. So it's never about knowing everything, but it's about knowing enough to make an informed decision about the best use of the resource you have available to you. So if you can't get off of that ledge, then you'll never be able to get started. One of the things that I like to say, guys, is that what stops us often from taking action is this feeling of discomfort, right? Like, the fear really boils down to, I don't feel comfortable with this decision. But the truth is, when you're doing something new, something that's outside of your normal skills scope, right, when you're doing something new, by default, it's going to be uncomfortable. So if you are always seeking the actions that make you feel comfortable, then you'll always be seeking things that are currently within your. Your skill set, which means you will not grow. Put another way, it is impossible to be growing and to be comfortable at the same time. Growth requires discomfort, right? Growth requires discomfort. So if you're listening and any of this resonated, shut up, hit pause and go analyze some deals and get some offers out.
Ashley Kerr
You know, I don't let my kids say that word, Tony. And now when they're listening to this episode in the car, they're gonna tell.
Tony J. Robinson
Them, uncle Tony said, it's all right. Just in this one specific use case.
Ashley Kerr
Along those lines, if you can analyze the deal, if you can estimate rent, if you're looking at comparables, if you're spending every night scrolling through Zillow and saying, you know what, I can tell this would make a good deal, this wouldn't make a good deal, and you have some sense as to the properties you actually be underwriting, then you need to build your buy box. You need to start putting, you know, properties together to, you know, make an offer. Even if you're not formally submitting an offer. Run the analysis and understand, like, okay, this is, this is the type of property that I actually want. This is my buy box. And kind of building it out from there. And that leads us into sign number three, that you're leaning towards a clear niche or strategy. And you really want to focus when you're building that buy box on what you actually want to undertake because there's shiny objects all over the place and you will get distracted. Like, there have been times in my life where I have a tab open looking at self storage, I have a tab open looking at campgrounds, and then I have a tab looking at a cabin in the middle of the woods. Okay, so you don't want to be like that. You want to niche down, especially to build that foundation.
Tony J. Robinson
Yeah, I think it's natural in the early part of your real estate investing journey to want to explore all of these, these different options because, I mean, that's part of trying to identify what resonates with you most. But at a certain point you'll start to say, like, man, I love the idea of flipping. Like, the idea sounds great, but man, I hate the idea of, you know, all of this active income that I'll have to chase. And it's like it's just one deal after the next. And I'm not making any money from not doing any deals. You might say, man, I love the idea of short term rentals, but man, the thought of, like talking to, you know, 15 different groups of people every single month for as long as I own this property, that's not super exciting for me. And as you start to have these different conversations with yourself, you'll naturally start to lean toward the idea of what makes the most sense for you. And you're like, well, hey, I really like the kind of renovation part of flipping right where I get to take it from, you know, an old beat up house to something that's beautiful. I like the idea of short term rentals where I get to give a really good experience. So maybe I'll do midterm rentals, or I can still buy old homes and I'll burn midterm rentals and I'll buy old homes, I'll fix them up and then I'll place a midterm rental there. So I still kind of get the short term rental pizzazz, but I get the increased cash flow and I kind of get to meet, right? So you'll start to have those kind of conversations with yourself. And as you find that focus, it'll give you more confidence on what you need to do. And I think the, the goal here is that you're able to match the strategy to who you are and what your resources are. Right? So for example, if you have very limited capital, then maybe house hacking makes the most sense for you. Because house hacking oftentimes allows you to get into a deal with the least amount of cash out of pocket. If you have maybe a lot of cash on hand, you can get access to a lot of cash and you want to be super hands on and you like the idea of projects, then maybe flipping makes a lot of sense. If you like creativity and you're, you're, you're an artist in your heart and you want to build beautiful things, then maybe short term rentals makes a lot of sense for you. If you're super risk averse and you don't have a lot of time and you just want something steady, then maybe turnkey long term rentals makes a lot of sense. But the goal is that you want to match the strategy to where you are in your life and what your resources are, your time, abilities and desires to make sure that you're, you're leaning into the right niche, into the right strategy.
Ashley Kerr
One mistake that I made along my journey was not sitting down and doing this. I started thinking, okay, I've got my long term rentals set, I'm bored, I want to go and chase something else. And it's okay to pivot, it's okay to change your strategy and things like that. But I didn't have a clear goal or understanding of the lifestyle or what I wanted out of real estate. I was just looking at, oh, this is, this looks fun, this looks exciting, this looks like it can make money. And I actually pursued a campground where I'd be doing a syndication. And along the way I realized I do not want to do a syndication. I do not want to have investors, you know, reaching out to me, like to find out how is the property going and do like that, and I understand that you can set up, you know, communication restrictions and stuff like that, but I didn't want to. To deal with a huge, huge property, it would have had to take a million dollars in renovations. And I realized, like, I'm lazy. I don't have the work ethic or the time commitment to put in what it would have taken to take down this property and to get it fully operational and get it running. So I think I needed to, like, be clear with myself and understand, like, you know what, I just want to build the slow and simple. I'm not looking to become a billionaire. I just want to build wealth for myself that I can enjoy and also have some leftover for my kids someday. So I think once I came to that realization that I didn't have to grow and scale and become this, this huge investor and build this huge empire, that actually what I was building was working for me in the lifestyle that I wanted today and for in the future too. So that was definitely one mistake that I had made, was not fitting that strategy I pivoted to within my lifestyle.
Tony J. Robinson
And some of it is, is experimentation, right? Like we're going to try certain things, we're going to go down certain paths. And you might be far down that path before you make that realization that actually this doesn't really align with what I want. And that's okay because it is almost a process of elimination to clearly identify what niche and strategy makes the most sense for you. So even if you're not fully committed, if you're leaning towards one, that's why we said leaning right. If you're leaning towards a strategy, then it's time to start taking action to really validate whether or not it makes sense for you. So even when the numbers make sense and your niche feels right, one final sign separates the dreamers from the doers. And it has nothing to do with money. And we'll cover what that is right after word from today's show sponsors.
Ashley Kerr
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Tony J. Robinson
All right, so at this point, you have the money, you've got the knowledge and the focus. The last question is why are you doing this? And that takes us to sign number four, that you have clarity on what your why is. Okay, so you know what your why is. Guys, we almost should have started with this. But I, I really, as I've matured as an investor, I think I've found the importance, or I better understand the importance of understanding your motivations and your why as a real estate investor. Because based on what your why is, based on what your motivation is, we could look at the same exact opportunity and come to completely different conclusions on whether or not it is a good deal. Because good is a very subjective word and it's based on what are your goals. And if my goal is to, like Ashley just said when we were talking about the last sign that she doesn't want to be a billionaire. And if you, if you took Ashley and you know, you, you sat her down with a young Jeff Bezos and you gave them the same opportunity, they would look at it differently because of their motivations for why they're doing the work that they're doing. Same could be said. I know, I know a real estate investor who he invests in real estate, but his real passion is he does like these trips to Africa and really all around the globe, but it's all about like environmental advocacy, like that. That's what his passion is. So he really just wants real estate to be able to support that passion of his. So his reasons and motivations for investing are very different than even what Ashley's are. So every person has a different why. So getting back to the sign here, if you know what your why is, if you have clarity on why am I actually investing in real estate, do you want true financial freedom or do you just want extra income? Are you looking for long term wealth where 30 years down the line you can, you know, have a fully paid for real estate portfolio and not worry about anything else? Or, or do you want quick cash flow today so you can quit your Job as fast as possible. Right? But just having clarity on, hey, why am I doing this? Is one of the most important things to say. I'm actually ready.
Ashley Kerr
The. The last piece I'll add to this before we go to break is that all of that is very important. But also for your very first deal for building that foundation, I want you to think about what you would be good at even if you don't enjoy it. So, like, if you really want to build wealth faster, you should be picking a strategy where you will excel at it. So, for example, I love the idea of designing airbnbs and picking out tile and all of those things. I love that idea. I am not good at it. I have stood in Home Depot in the tile aisle for an hour with my children trying to pick out a tile for a bathroom shower. Okay? So that is not an efficient time that is slowing me down in my wealth building process, and I'm just not good at it. Yes, sometimes I will still do it because it's fun and I want to enjoy it. But if I would have started out picking a strategy like short term rentals, where I had no mentor like I did for long term rentals, I knew nothing about it and I wasn't good at hospitality like I was used to. You know, a property manager that's responding with tenants who are constantly complaining all the day. And I was already like becoming a grouchy person because of that, that I probably wouldn't have been this nice, sweet, friendly person responding to the Airbnb guest. So I would have failed. I would have failed. I know, I knew it. So I did the long term rentals and I think that really helped me set up for success was that even though it's the, the boring method and it wasn't exciting, like I knew more about that and I had the opportunity there and I took advantage. So also think about that piece too. Even though you may want to do the thing that will be fun for you and fulfill a passion that can come later. And I, you know, I think it was five years, six years after investing, I bought my A frame and I went $40,000 over budget and failed at first. And now it is great and wonderful, but that $40,000, if that was my first deal at that time, that would have bankrupt me for sure.
Tony J. Robinson
I'm just gonna. We're pretty much done with the four signs, Ash. I'm just gonna finish off with like a, hey, do these things in the next, like 90 days, help you get your first deal. So we can just kind of like riff on that to finish this one out really quick. So, guys, those are the four signs, right? And as you put all of those pieces together, if you can say yes to all four of those, then you are ready. No if, ands or buts about it. You are ready if you can say yes to those. So I want to give you guys a bit of a roadmap or like a challenge to help you actually make some progress here. Okay? What I've seen as one of the biggest obstacles to aspiring investors actually getting their first deal is a lack of activity. It's not a lack of skill, it's not a lack of knowledge, it's a lack of activity. So what I want to focus on is squeezing and cramming an incredible amount of activity in a very short period of time. So what I want all of you guys to do is to, for the next seven days, I want you to analyze and submit on a different property every day for the next seven days. Notice I said analyze and submit on. I don't care what the purchase price is. I don't want you to care what the purchase price is. You do your analysis. It doesn't matter what your strategy is. Flipping, wholesaling, long term, short term, midterm apartments, single family, mobile home, parks, whatever. Find seven different properties, one per day. Analyze it, identify where your necessary purchase price is and submit the offer 10 or 15% below what your max offer is. And the absolute worst thing that's going to happen is that you break through this fear of submitting offers and they say no. That's the absolute worst case scenario. The best case scenario is that one of those people says, yes. They're like, yes, I will take your offer. And the more likely scenario is that there'll be some sort of negotiation in the middle. Right? But the simple act of breaking through that glass ceiling of I'm afraid to submit a lot of offers, I'm afraid to lowball people. If you can break through that, it then makes offer number 8, 9, 10, 20, 30 significantly easier. So that's my challenge. Ash, what do you think? What do you have to add for people to break through the analysis? Paralysis.
Ashley Kerr
Yeah, I think everything along the lines that you said. And one thing I want to add in is partner alignment. So is this your spouse, your significant other? Maybe you have a partner in the deal is to. As you're going through this, this analysis paralysis of like trying to get started and things like that, even if it's not your spouse, significant other, or somebody you're partnering on the Deal like an accountability person to add into the mix. Like, find somebody who maybe is also stuck in analysis paralysis and, you know, hold each other accountable. Like, go get on a zoom call, go through each deal you're looking at and have the other person call you out and say, I don't see anything wrong with this deal. I think you should do it. Or maybe they will say, you know what, I think you missed this. Or you should look at this more and maybe this isn't a good deal. And it kind of gives you that reassurance. This could be another rookie. It's another set of eyes, somebody who's going through the same exact thing you are, but also that alignment of like, as you're listening to this episode, maybe there was a couple aha moments of like, you know what? I have been thinking of this strategy. But. But Ashley's right, per usual, and I don't think I'd actually be good at that. So go ahead and, you know, align with your. Your spouse, your significant other, and make sure that you are on the right track for what fits both of you. Because if you go down this rabbit hole and you're got all these ideas and stuff like that and you go ahead and implement them, maybe you love the idea of working nights and, you know, going and doing the rehab to build wealth from your family, you're gonna do it. But maybe your. Your spouse does not like the idea of you not being at your kids soccer games or you not being home for dinner or things like that. So having alignment and then also an accountability person to. To kind of help you through this analysis paralysis. Okay, well, thank you guys so much for listening to this episode. I'm Ashley, here's Toni, and we'll see you gu the next one.
Tony J. 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.
Ashley 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.
Tony J. Robinson
So head over to biggerpockets.com guest if you want to be a part of our show again. That's biggerpockets.com guest and we'd love to have you on.
Episode Title: 4 Signs You’re Ready to Buy a Rental Property (Sooner Than You Think)
Hosts: Ashley Kehr & Tony J. Robinson
Podcast: Real Estate Rookie by BiggerPockets
Date: November 19, 2025
In this episode, hosts Ashley Kehr and Tony J. Robinson outline the four key signs that indicate you’re ready to buy your first rental property—even if you don’t quite believe it yet. With energetic encouragement and actionable advice, they help rookie investors break through common myths and analysis paralysis, so you can move from learning to doing. The episode is packed with practical tips, candid anecdotes, and motivational challenges for listeners who are ready to take the leap into real estate investing.
| Timestamp | Segment/Topic | |-----------|--------------------------------------------------------------------| | 00:33 | Sign 1: Strong personal finance foundation | | 06:13 | Down payment myths, loan products | | 11:02 | Sign 2: Overcoming analysis paralysis/taking imperfect action | | 15:01 | Sign 3: Clarity on niche/strategy (“buy box”) | | 23:30 | Sign 4: Clarity on your “why” and its impact | | 27:51 | Roadmap/challenge to break analysis paralysis | | 30:09 | Importance of accountability/alignment with partners |
The hosts maintain an upbeat, supportive, and practical tone, sharing both personal lessons and direct advice in a way that’s approachable for rookies. Both Tony and Ashley use humor and real-world examples to make their points memorable and actionable.
If you can affirm:
You are ready to take action. The difference between dreamers and doers is activity—so take the challenge, submit those offers, and get a trusted accountability partner for support. Your real estate journey starts now.