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

Ashley:
Most rockies imagine there’s a second coming once they’ll lastly really feel prepared to purchase a deal. When the market is sensible, the numbers really feel safer and the concern goes away.

Tony:
However the reality is that moments nearly by no means comes. And in 2026, that perception alone is the most important cause most rookies will keep caught on the sidelines.

Ashley:
That is the Actual Property Rookie Podcast, and I’m Ashley Kehr.

Tony:
And I’m Tony J. Robinson, and at this time we’re going to interrupt down the the reason why most rookies is not going to purchase a deal in 2026. And as we undergo these causes, we’re additionally going to name out how one can be the exception. So should you hear your self being echoed in a few of these factors, don’t fear, we’ll try to present you the best way to repair it as properly. All proper? So the primary cause that you just most likely received’t purchase a deal in 2026 is since you’re complicated consolation with confidence. And we’ve talked about this within the podcast earlier than, however oftentimes rookie traders need to really feel comfy with the thought of shopping for their first rental. They need this consolation once they submit the supply. They need this consolation once they signal the closing docs. They need this consolation once they welcome of their first tenant or their friends or their first flip or no matter it might be.
However right here’s the reality, guys. It’s bodily not possible to be comfy and to be rising on the similar time as a result of by definition, progress solely occurs whenever you’re stepping outdoors of no matter consolation zone you presently exist in. So should you’re ready for this second of this consolation to seem as a way to do that factor you’ve by no means finished, you’ll get caught on this countless loop the place you by no means truly take motion. Now, confidence then again is one thing which you could construct in the direction of. The extra offers that you just underwrite, the extra folks that you just discuss to who’ve already efficiently finished the factor you’re attempting to do, the extra brokers you discuss with, the extra property managers, the extra basic contractors, the extra information factors you need to assist your determination, that’s the way you construct confidence. In order that’s the primary one for me. Cease complicated consolation with confidence. Give attention to confidence, not consolation.

Ashley:
A giant a part of this I feel folks don’t have a look at is you go to a W2 job almost definitely each single day and you’re feeling protected. You are feeling comfy taking over a job and that gives you that consolation. And going into actual property and shopping for a property feels uncomfortable. It appears like a threat. It’s a must to have a look at the variations of those since you really feel comfy in your job, however you possibly can actually be fired at any second, any day and lose your revenue. However but folks see a job as they’re comfy with that, however someway actual property and shopping for a property is a much bigger threat and has larger potential to fail. However should you have a look at the 2 completely different eventualities, having a W2 job is absolutely not that protected in any respect. The place should you’re shopping for an funding property, you’ve extra management over that asset and extra choices as to how one can truly make it worthwhile, make it a possibility for your self than your personal W2 job most often.
So I feel having that management piece is an enormous distinction of with the ability to reduce your threat and to supply a possibility for your self which you could management and never your boss or the proprietor of your organization that’s controlling your future.

Tony:
And what this prices you whenever you’re caught on this loop of attempting to really feel comfy earlier than you’re taking motion is that you just by no means truly get the reps in that construct the boldness. The one approach that you just construct confidence is by getting the reps in, utilizing the information that’s in entrance of you to truly get the reps in. So I at all times inform people, it’s like the primary glass ceiling you need to break by means of is submitting that first supply. And I might encourage each single one that’s listening at this time to only go submit a suggestion on one thing and simply make it an extremely low, nearly insulting supply as a result of the purpose isn’t that you just truly get the supply accepted. The purpose is that you just cease being afraid of submitting a suggestion. So whenever you get caught on consolation versus confidence, you lose that capability to get your reps in.
However when it comes to how one can be the exception, the very first thing is to take motion earlier than consolation reveals up. Simply stroll into this realizing that it’s going to really feel somewhat uneasy. You’re going to be second guessing your self somewhat bit. You’re going to be like, “Am I doing this proper?” Now, I’m not telling you to leap in ill-equipped or unprepared, proper? Nonetheless do all of the work you’ll want to do to really feel that you just’re taking the fitting subsequent step, however simply understand it’s going to really feel somewhat uneasy. It’s going to really feel somewhat possibly nauseous as you submit that first supply. After which I feel the subsequent piece is to outline the one uncomfortable motion that you just’ll take. Already talked about submitting the supply. I feel that’s an ideal massive one to take. However even earlier than that, easy issues like selecting up the cellphone and speaking to brokers.
What number of brokers are you able to discuss to that can assist you get to your first deal is a good factor to do. What number of basic contractors and quotes are you able to get for a possible property that you just’re ? The extra motion you’re taking, the simpler it turns into to take that subsequent step. And I feel if we measure our progress based mostly on the actions that we’re taking, not essentially whether or not or not the deal is completed, that’s how we make it possible for we’re making progress over time. In order that’s the primary one. Cease complicated consolation with confidence.

Ashley:
Consolation truly retains most rookies from beginning, however subsequent we’ll break down why chasing good offers retains them from ever ending. We’ll be proper again after a phrase from our present sponsors. Okay. Welcome again. So as soon as rookies push previous consolation, the subsequent entice appears to be like productive, however nonetheless prevents shopping for. So let’s get into why you received’t purchase a deal. And that cause is since you’re ready for a deal to only fall into your lap with out truly going out and discovering a deal. And I’ve positively been responsible of this myself. Even through the years, I’ll simply sit and suppose, “ what? I’m not going to chase a deal. Perhaps I’ll get one this 12 months or one thing.” However I feel that if I actually, actually need to discover a deal, I’ve to exit and I’ve to place within the work. I’ve to place within the effort of discovering the deal and never simply scrolling the MLS ready for the proper deal to seem to me.

Tony:
Yeah. You’ll be able to’t manifest a superb deal into your life. You’ll be able to’t constructive suppose your approach right into a deal.You’ve received to truly do some work. And our good buddy, James Danar from the On the Market podcast at all times talks about offers aren’t discovered, however they’re constructed or they’re made or he phrased them in a sure approach, but it surely’s like principally you need to go on the market and manufacture the fitting deal. And for him, what he talks about numerous occasions is, “Okay, what does a marketing strategy appear to be on this deal that might enable me to show into a superb deal?” So possibly I’m shopping for it as a 3 bed room, however I’m changing it to a 5 bed room, and that’s how I make this deal work. We’ve interviewed Laka Davetha and he or she’s constructed an unimaginable portfolio within the Seattle space, however what she’s centered on rather a lot not too long ago are ADUs.
And for her, it’s like, “Hey, I can exit right here and purchase a single household dwelling and possibly it doesn’t work that approach, but when I do a indifferent ADU, that utterly modifications the economics on this deal. And now I’ve received two properties for the worth of 1, which permits me to go on the market and generate extra income.” The Nawsums, Shannon and Christian, who we interviewed within the podcast, they do room leases and so they’ll exit and purchase a 3 bed room dwelling and convert it to a seven bed room dwelling after which they’re renting to college students. So it really works for his or her enterprise mannequin. So I feel we’ve received to get out of the thought of simply, I’m going to look on Redfin or Zillow and that’s the place I’m going to seek out the proper deal, but it surely’s how can I possibly get somewhat bit extra artistic?
How can I put somewhat bit extra work? How can I view this from a barely completely different angle to try to discover the fitting strategy for me that enables me to get a superb deal?

Ashley:
And I feel even earlier than that, should you’re ready for the fitting deal to fall into your lap, do you even know what the proper deal is? Do you even know what deal you need to fall into your lap? Have you ever outlined your purchase field? Are you aware precisely what technique you’re going to do? And that may actually enable you slender down your focus and be capable to actively go after what you’re in search of as a substitute of simply ready and searching and like, “Oh, you realize what, that doesn’t look nice. No, not that, not that. ” And ready for what’s going to be good for you, I feel actually defining what’s the deal that you just’re in search of first after which attempting to actively go and seek for that. And it’ll be simpler to seek for it should you truly know what you’re in search of too.

Tony:
Now, Ash, you make an ideal level. And two issues I’d add to that. Primary is that should you’re simply ready for an agent to ship you good offers, it’s not that that strategy received’t work in any respect, however it’s that that strategy goes to be a considerably slower route towards discovering your first deal. Of all of the properties in my portfolio, I feel possibly my first, the very first one which I purchased, I feel could be the one one which an agent truly despatched to me the place they have been like, “Hey, right here’s one which form of pops up that meets your purchase field and your standards. Right here’s the place I feel we should always submit our supply,” so on and so forth. Each different deal has been me on the market looking, searching, underwriting, analyzing, after which going again to my agent saying, “Hey, right here’s my supply. Right here’s what I’m pondering.
What are your ideas? Cool, you’re on the identical web page. All proper, let’s transfer ahead.” So I feel first you’ve received to alter the function that your agent is enjoying to extra of an advisor than your straight deal finder.

Ashley:
It’s only a bonus should you get a deal dropped at you. I’ve gotten a ton of offers from phrase of mouth referrals. “Oh, my cousin’s promoting a property. Let me provide you with their quantity. I do know they need to do away with it. “These ought to simply be bonuses and also you shouldn’t depend upon the agent bringing you offers or the phrase of mouth offers or referrals from different folks to lock in a deal.

Tony:
And I feel the second piece to your level, Ashley, of you received’t know what to search for till you begin taking a few of this motion. One among my robust suggestions for people is that earlier than you even begin trying to find a deal to buy, first do the analysis on what’s already working properly in your market. And this may apply to long-term leases, short-term leases, midterm leases flipping, however let’s say that I’m a flipper. I can use Zillow, I can use Redfin. There are web sites like PropStream or Privy the place you may make the search somewhat bit simpler, however I can return and discover properties which have not too long ago been flipped out there that I’m and I can in a short time begin to determine, okay, properly, the place are the areas the place nearly all of the flips are taking place? So then I can go from a complete metropolis or a complete county, possibly all the way down to a selected zip code or sure blocks inside these cities that really work properly.
Then I can begin to see, okay, properly, what are the bed room counts and form of sq. footage ranges which might be often transferring the quickest? After which I can say, okay, properly, possibly the one bedrooms don’t promote all that properly. Or man, if I get beneath 1000 sq. toes, these have a tendency to sit down a bit longer. But when I’ve received a superb starter dwelling, three bedrooms, two baths, even as much as 4 bedrooms, these have a tendency to maneuver fairly shortly. However man, if I begin attempting to promote like a 5 or a six bed room, these are inclined to settle a bit longer as properly. So you can begin to engineer what your purchase field appears to be like like by merely wanting on the information of what’s already been profitable in your market, after which that offers you a greater sense of, okay, now what do I must go search for on this market to achieve success?
So should you’re looking for offers, among the best locations to start out is by what’s already bought in your market. I feel a further level so as to add to this too, Ash, is that as you begin to do the work of really sourcing the offers, one of many different factors that you need to be centered on is best understanding the vendor. And I feel that’s the place numerous Ricky traders additionally get caught up is that they see the checklist worth for a property and so they take that as gospel, proper? It’s like that vendor is simply prepared to just accept that checklist worth. And I used to be simply speaking to somebody yesterday who’s trying to purchase their first Airbnb and he was a reasonably costly property in upstate New York. I feel it was listed for like $1.69 million and the deal labored for him at like 1.3.
So there’s like a $300,000 hole, which isn’t a small amount of cash, however the property had been listed for the higher a part of a 12 months. So this man who’s trying to promote this property has been sitting on a $1.7 million property for over a 12 months and it’s simply been sitting empty and he has been renting it throughout that point. So for me, it’s like, hey, there could be some motivation for this vendor to truly budge off of that 1.7 buy worth. However the man who I used to be speaking to was like, “Man, I simply don’t need to offend this vendor.” And what I shared with him was I might be extra involved about locking up a property on the flawed worth than I might be about offending the vendor. So I mentioned, “Man, simply submit the supply, no matter quantity makes essentially the most sense for you.
” So he went to the agent, his beginning quantity was 1.2 million, and the agent got here again and mentioned, “Hey, look, it’s listed at 1.7. I do know the vendor will most likely come all the way down to 1.5. 1.2 could be an excessive amount of of a stretch.” However even there, we went from 1.7 to 1.5 with one fast dialog. So I feel the most important factor for rookies to grasp is that you just’ve received to place the ball within the court docket of the vendor to both settle for, reject, or alter no matter give you’ve submitted to them, however don’t try to get of their head and make that call for them. So I feel that’s one vital level in the case of discovering the fitting deal.

Ashley:
I feel too, should you don’t know this individual personally, should you offend them, will you ever discuss to them or meet them once more and even take into consideration them once more? Normally, no. Okay, you offended somebody, you’ll by no means work together with them once more as a result of they’re not promoting your own home, you’re not shopping for it and you progress on to the subsequent deal. But when they negotiate with you or they carry it down, now you’ve received your self a deal. Belief me, I’m the worst individual to ask about confrontation, however even that, I’m okay with

Tony:
It. However Ashley, let me even ask you, let’s say that you just have been promoting that property for 1.7 and somebody got here and provided you 900K, would you even reply to that supply?

Ashley:
Yeah, I might at the very least counter supply. I might at the very least do a counter if I might say the 1.5 or no matter, I might at the very least counter and say that’s the bottom I’m prepared to go.

Tony:
And what in the event that they got here again after you countered it at 1.5 and so they’re like, “ what, Ashley, because you countered me, I’m truly going to scale back my worth to 500K.” What would you say subsequent?

Ashley:
Then I most likely would simply inform my agent, both don’t reply or … So

Tony:
At that time, you could be thought of insulted by their supply, proper? Let’s say that very same vendor got here again to you and so they’re like, “ what, Ashley? I’ve a while to mirror. I spotted I used to be flawed for that supply of 500K. I need to now give you a full worth supply at 1.7.” Would you be okay with that? What would you say to that?

Ashley:
Yeah, particularly if that is an funding property, I don’t care who I’m promoting it to. Even my very own home, I don’t care who’s shopping for it or what you’re going to do to it. Sure, somebody that’s lived into their home and brought care of it and constructed stunning gardens and every thing, after which possibly they need to drive by as soon as every week and ensure every thing’s great, desires to promote it to a household and blah, blah, blah and stuff like that. However as an investor, I don’t care what you do with the property after you’ve written me a test.

Tony:
And I feel that’s the situation or that’s the mindset for lots of people. And that’s why I went by means of that little thought train as a result of it’s like, even should you offend a vendor along with your first supply, there’s often some quantity the place that supply is now not offensive. You’ve simply received to determine if you will get as near that quantity with out going over the place the deal is sensible for you.

Ashley:
And one factor too is comply with up with them. So that you do your low ball supply, no matter, they don’t reply or they get mad, no matter occurs. Three months later, comply with up and ask their agent or would they be prepared to return down anymore or what’s happening with the deal? Observe up. There’s most likely been two circumstances I can suppose off the highest of my head the place I’ve put affords on a property, they mentioned no, and 6 months later it closed for lower than what I had initially provided. However I don’t know if it’s both simply them pondering I’m not anymore as a result of it’s been so lengthy or them in the event that they actually have been insulted and didn’t need me to purchase it due to my first supply, however but they bought it due to that. However I feel proceed to comply with up. Even should you do insult the individual and so they’re mad, proceed that comply with up with them or their agent at the very least along with your agent or one thing like that.

Tony:
And I get why so many Ricky traders are nervous about quote unquote insulting the vendor, however guys, simply know should you come again with a greater supply, that insult, it often goes away fairly shortly, proper? So understanding the vendor, attempting to get a greater understanding of their ache factors. One different piece on that too, Ash, and we’ve interviewed numerous people who’ve talked about this. You talked about that the vendor who desires to drive by and see their backyard each time. And it’s as a result of we’ve interviewed people who’ve gotten extremely nice offers as a result of they provided one thing that appeared tremendous insignificant to you as the customer, however was very vital to the one who was promoting it. We’ve interviewed people who’ve gotten massive reductions as a result of they helped the vendor transfer. They’re like, “Hey, I’ll get a transferring truck for you so that you don’t have to fret about transferring every thing out.
” We simply interviewed somebody who received a deal as a result of they promised to handle the backyard that this little previous woman had been cultivating in her yard. So there are such a lot of, like Ash, even you, you mentioned certainly one of your offers, you promised the vendor that you’d preserve one of many tenants in place as a result of she had been there for thus lengthy. So each vendor has a distinct motivation and the higher you possibly can perceive what’s vital to them, the higher supply you possibly can craft that’s not even associated to the worth of the property that may assist you to truly shut on that deal. So we may most likely do a complete episode simply in negotiating with sellers and understanding motivations, however simply now excessive stage, tremendous vital to concentrate on.

Ashley:
BiggerPockets additionally has an ideal e-book for negotiating offers written by J. Scott, and you could find that within the greater pockets of bookstore. Final

Tony:
Piece I’ll hit on this level right here is it’s additionally vital to grasp the completely different financing choices which might be out there to you as you look to purchase, as a result of that may additionally have an effect on the affords and the offers you possibly can truly shut on. If Ashley and I are each wanting on the similar precise property, however Ash has simply gone to Financial institution of America to get her debt and so they’re like, “Hey, Ashley, we want 30% down on this deal.” And I am going to my native credit score union or I am going to twenty completely different credit score unions and so they’re like, “ what, Tony? Truly, should you get this deal and also you make investments one other 50K into the rehab, we expect it’ll be price much more as soon as it’s finished. We’ll fund the entire thing You simply received to go on the market and discover the deal.” Identical precise property, however very completely different mortgage merchandise goes to permit me to execute in a approach that Ashley wouldn’t be capable to execute on.
So one of many greatest errors that we see rookies make that will get them caught on the sideline goes to at least one financial institution or one lender and pondering that that individual has the entire potential mortgage merchandise which might be out there to you as you look to go purchase this deal. So store round extra, try to get extra choices when it comes to mortgage merchandise, concentrate on these small, native, regional banks who’ve extra flexibility in the case of financing funding properties, after which choose the fitting one which matches for the precise deal that you just’re . All proper. So even realizing how offers work isn’t sufficient. And proper after the break, we’re going to speak about why studying nonetheless isn’t translating into motion. We’ll be proper again after this. All proper. So at this stage, the issue isn’t info, it’s execution. So the ultimate cause why most rookies received’t purchase a deal in 2026 is since you get caught studying and also you by no means begin executing.
And this half is, it’s a sticky, form of slippery slope as a result of studying feels tremendous productive. You’re listening to the Actual Property Rookie Podcast, you’re watching YouTube movies, you’re saving random little clips on social media. All of this feels vital and it feels such as you’re making progress, however the factor is that studying doesn’t truly carry any threat. There’s zero threat related to listening to a podcast or watching a YouTube video or saving issues on social media. With out clear deadlines or stakes, schooling simply can form of flip right into a delay. I met somebody a number of days in the past who had been excited about shopping for an Airbnb and her and her husband had been excited about it for over two years. And whereas I dedicated them for like, “Okay, hey, it’s nice that you just took your time to coach your self.” There’s not that a lot. It ought to take you 24 months to truly soar in and take motion.
So that you’ve received to determine how do you make it possible for the buildup of information doesn’t result in in motion. And what I usually share with people is that should you get to some extent the place you’re listening to the Actual Property Rookie podcast or regardless of the podcast you hearken to and also you’re studying the completely different books and also you begin to notice that you just already know nearly all of what we’re discussing, you realize the phrases, the frameworks, BER, you realize ARV, you realize this, you realize that. You’re like, “Hey, Tony, I do know. I’m presupposed to go discuss to the native banks as properly. Hey, yeah, I do know I’m presupposed to submit a suggestion that’s going to be somewhat bit decrease than what I’m comfy.” If you realize all of these issues, then that’s a very, actually good signal that you just’ve already absorbed sufficient data and now it’s time to step into truly taking motion.

Ashley:
If I used to be a health care provider, I might diagnose you with evaluation paralysis. And I feel that is simply an enormous factor. You need to really feel again to the start of this episode, you need to really feel comfy and assured and also you suppose that the extra you study and the extra data you’ve, the higher you are feeling. Give it some thought. You go to high school and examine for what number of years simply to get your first job and so you are feeling assured and prepared. You’ve received all of this education, all of this finding out below your belt and now you’re able to do the job. And I feel in actual property that may be detrimental to you typically. Sure, I’m not saying go forward and simply soar into it with out realizing something, however you don’t must have 4 years of education to grasp the best way to buy a property and to function it as a rental.
And I feel that’s the place most individuals get confused is that they should take in all of this information. They should know every thing, however you don’t. You’ll be able to take into consideration the individuals who change into unintentional landlords. Take into consideration the people who find themselves going by means of some form of vital life influence that’s detrimental to them, however they’re nonetheless with the ability to purchase a rental property. Take into consideration any individual who didn’t even go to school recent out of highschool, purchased their first home hack. Take into consideration the folks which might be with the ability to do that with out spending years and years doing analysis or excited about it. And you might be most likely already forward of most individuals that get began by having two years to speak about it, by having two years to soak up data to study. Take into consideration should you purchased a property two years in the past, how a lot farther you’d be forward, how a lot fairness that property would have collected, how a lot expertise you’d have already obtained.
In order you hear, particularly when we now have the rookies on and to a few of the obstacles and the hurdles that they’ve overcome to do that, numerous you listening are most likely in a approach higher place to truly begin due to possibly time, cash, the data you’ve already absorbed. And I feel an enormous telltale signal is should you go into the BiggerPockets Boards, you possibly can reply a query, a pair questions, as a result of you realize the reply, you’re already rather a lot farther forward than different rookies too.

Tony:
And I feel step one is often the toughest. And it’s this quite common factor that we see amongst the oldsters that we interview and simply the those that we meet in life that the primary deal, like from the time you commit to truly closing that first deal, someplace between a 12 months to 24 months is fairly widespread, however that second deal by no means takes so long as the primary deal. And that’s as a result of when you get that first deal finished, every thing else turns into a lot simpler. So simply know that step one is often the toughest. So if you wish to be the exception right here on this final cause that almost all rookies received’t purchase a deal, right here’s the one problem. Set a purpose on the variety of offers that you just’ll analyze in 2026 and the variety of affords that you just’ll submit in 2026. And should you simply work actually, actually onerous to hit these two issues, likelihood is you’ll find yourself discovering at the very least a number of offers which might be adequate so that you can actually need to transfer ahead with.
So what number of offers are you analyzing? What number of affords are you submitting? And the purpose is that you need to use each of these actions to get you to your first deal.

Ashley:
Effectively, thanks guys a lot for listening to this episode of Actual Property Rookie. I’m Ashley, he’s Tony, and we’ll catch you guys on the subsequent one.