
Loading summary
A
What if rising rates made every deal feel impossible, your cash flow no longer works, and you're starting to wonder if real estate investing is even worth it anymore. Or maybe you're brand new and asking, how do I even break into this industry when I have zero experience?
B
And when tax season rolls around, what should you actually ask your CPA to make sure you're not leaving money on the table? Today we're breaking down all three of these listener questions that get to the heart of what rookies are struggling with right now, but financing, experience, and taxes.
A
This is the Real Estate Rookie Podcast. I'm Ashley Kerr.
B
And I'm Tony J. Robinson. And with that, let's get into today's first question. So today's first question comes from Ray in the BiggerPockets forums, and Ray says, I'm a newbie looking to purchase my first rental property and I am in need of some advice. My main goal going into real estate investing is to gain some cash flow so I can scale down. Not necessarily quit, but my day job, which seemed fairly attainable based on the deal analysis on the site and discussions on the BP podcast. But recently I've seen several forum posts stating it's no longer possible to have cash flow and that you'll be lucky to even break even. Is this true or does it just take more careful planning and knowledge in today's world? I've heard high interest rates are one thing that are hampering cash flow, but my plan was to tap into the equity from our home to cover the first rental, understanding that we could get a better interest rate on a HELOC than with a traditional loan and therefore create more cash flow. Is that correct or does it all depend on the LTV ratio on the HELOC as to how low the interest rate will be? The other option is to withdraw money from our Roth IRAs to pay in cash, which would give us decent cash flow on the first property, but we will still need to finance the second, third, fourth, etc. Through a HELOC or traditional loan and would then face the same question of whether we can find a deal that gives us some as in 2 to $300 per month in cash flow. So I'd like to figure out, is cash flow still an option and if so, what is the best strategy if that's my goal. Great question, and I feel like there are probably a lot of people listening right now who are thinking about investing in real estate but are hesitant for a lot of the same reasons that Ray just said, right? They're just hearing a lot of chatter about what real estate investing looks like today. Today, I think first is maybe just have like a quick history lesson and then, you know, Ash, we can both give our take. Interest rates are high right now, right? A lot higher than what they've been, you know, in my adult life. You know, and I think a lot of folks, even when BP got started, like BP got started, like right around the Great Depression. And there are a lot of folks who are investing when it was probably one of the best times in the, you know, history of mankind to invest in real estate. But even as the market stabilized and before COVID it was still a good time. There are unique challenges today. Inventory is constrained in a lot of places. That's pushing prices higher in a lot of places, and interest rates are making it more difficult. That said, I think anytime that we make blanket statements about real estate investing everywhere, across every strategy, it becomes a lot harder to say things that are actually true. And while some markets and some strategies, maybe it is difficult or maybe impossible to cash flow, there are definitely markets and opportunities and strategies that still work. And I'll give a quick example. I was just talking to a real estate investor last week, and she's based on the east coast in Jersey, but she buys duplexes in Philadelphia, and her strategy is burying duplexes in Philadelphia and then putting in Section 8 tenants. And she said her average cash flow across those deals, even for deals she's buying Today, it's about 1,000 bucks per month. 1,000 bucks per month on a duplex in a C class neighborhood in Philadelphia. So the question isn't, does it work or can I get cash flow? The question is what? What market should I be focused on? What strategy should I be focused on, what niche should I be in? And it's the combination of those things that I think will help you find the cash flow. So that's my initial take. Ash, what are your thoughts?
A
Yeah, I think the combination is key as far as not only your market, things like that, and the property type, but also what other benefits you can get with real estate. Because I think a big comparison right now is should I invest in real estate, should I invest in the stock market? And you're not going to get the same benefits like tax benefits, tax advantages, appreciation, things like that that you would with the stock market. You're just going to get the value of the stock price going up, or maybe you'll get dividends, things like that. But real estate has its own specific benefits. So first, outweigh what other things are important to you? So if you want to reduce your taxable income, real estate may be a better option for you than the stock market, even if you could get the same return on either one. So I think those are two, like major investments that you could be looking at to choose between. And I think you have to look at not only the performance in the long run, but also look at the other benefits that you can get from either one. And I like real estate because I believe it has more benefits that, you know, benefit me right now in my journey. I want to hold properties for a long time and then sell them way down the road. I want to get the tax benefits right now to decrease my income and keep more money in my pocket now. So I think looking at that is really important too is what other benefits do you have? Your tenants paying down your mortgage, you're not even paying for the property appreciation, building that equity in the property and then just the, the, the tax benefits that rental income is taxed different than W2 income and being able to use things like the short term rental loophole or you know, doing cost segregation studies on a long term rental or short term rental and also being able to get that real estate professional status for you or maybe your spouse to really be able to decrease your taxable income. So that's something I think you also need to consider when looking at real estate as to like, oh, this is only going to cash flow, $300 a month, but what if that same exact property could actually decrease you not having to pay $20,000 in taxes that year, that's almost, you know, a little over $1,000 a month that you're keeping back into your pocket that you're not paying into taxes. And that's the one thing that took me a long time to realize is this benefit besides just cash flow. So I think take that into consideration too as to how much money overall can you keep in your pocket.
B
Ash, how have your maybe expectations around cash flow shifted, you know, from when you first started investing to today? Because I think that's a big part of it too. It's just like having realistic expectations around what's here. So yeah, how, how, how has that shifted for you?
A
Yeah, cash flow is everything. Cash flow is king. Cash flow is how I was going to quit my job. Cash flow is how I was paying off my student loans. And for a while it worked. It was great. But like I realized some of the really great cash flowing properties were headache properties. They were like in class C areas and they Needed a ton of just attention. There were headaches, a lot of turnover, things like that. And I realized over time that yes, cash flow, cash flow is really good and you should not ignore it and you should not buy a cash flow negative property. But there are so many other benefits. Like, like, there's just like, I feel like one day where I just looked at this property I'd bought in 2017 for $143,000 and looked at what the rents were when I bought it compared to how much I had been able to increase the rents over the years and then what the value of that property was now. Like, I could probably sell that property for 250 to $300,000. The tenants have paid the mortgage down to like 95,000. I had put, I think like a 25,000 down payment maybe on it, maybe 30,000. And just looking at if I sold that property now, how much money I would get, how much I'm cash flowing on that property. So really though, I was like, I was like in shock when I like had that realization one day, like the aha moment of like, wow, those, you know, 10 years, eight years went really, really fast. And now it's like, okay, if I keep doing that, there's so much more value than just the cash flow. So again, the cash flow built my strong, steady foundation and now I can focus more on that appreciation and long term gain too for the properties. What about you, Tony?
B
Yeah, I think for me just, you know, like my expectations around the type of cash flow that we can get today has definitely shifted. Like, you know, if you go back to like on my wife and I, we have a YouTube channel, the Real Estate Robinsons. And if you go back and you watch some of those earlier videos and we talk about the types of deals we were looking at buying, we typically, you know, like, there's, there's a 1% rule, the 2% rule in the long term rental space. And you know, I had like a 30% rule where it's like, man, if I can get my annual revenue to be at least 30% of the purchase price and it's a really good deal. So if I bought a house for, you know, for round number sake, let's say I buy a house for $100,000. If I can do $30,000 in annual revenue, then it's a good deal, or $1,000,000. Property does 300k, it's a good deal. Today that number is probably closer to like 15 to 20%, you know, and it's because rates have effectively doubled. Since I bought my first short term rental. Right. So that means that we've got to see the, the returns probably go down a little bit as well. So I think the, the question isn't should I be investing in real estate or should I not be? The question is what is the best way for me to do it today. And we just entered, you know, we interviewed Thatch Wynne and James Dainard as two investors who have been doing this for decades and they both echo the same exact thought. The people who say now is not a good time to buy are the people who are probably never going to get started because there's always a reason or some data point that you can point to to say now is not the right time to buy. But it's the people who understand that every time it's the right time to buy it's just adjusting your strategy and adjusting your expectations is how you continue to get ahead. So I, I get the fear guys and I, I, I get the hesitation, but you've got to be able to separate who you're taking advice from. And if the folks who, who are telling you don't buy real estate are people who've never bought real estate or maybe people who have done it without the proper guidance and education and they're not really part of the bigger pockets ecosystem and they're not actively doing this, you gotta kind of filter that, that advice out. So yes, now is still a good time to do it. You just gotta figure out the right way to do it.
A
So if you can't make the math work yet, what if your day job was your training ground? After the break, we'll talk about which jobs actually teach you to invest smarter. We'll be right back. Thinking about wholesaling or flipping your first property, but not sure where to start. The truth is deals don't just fall into your lap anymore. You need to go out and create opportunities. That's where PropStream comes in. With Propstream, you get instant Access to over 160 million properties nationwide. Use 20 rebuilt lead lists such as pre foreclosures, tax delinquencies and vacant homes to find motivated sellers fast. And now Propstream has integrated batch leads and batch dialer to provide you with a complete all in one solution. That means you can not only find motivated sellers, but you can also reach out right away. Skiptrace phone numbers free on select plans, then send postcards, emails or call sellers directly. Worry if you're new. PropStream also gives you AI powered insights and comps that are over 99% accurate so you know you're making smart offers. Plus, you'll have access to Propstream Academy to guide you step by step. Start your seven day free trial and get 50 free leads@propstream.com BP that's P R O P S T r e a m.com BP don't just dream about real estate. Make it happen with Propstream.
C
What if I told you you could forget everything you know about investment property loans? Because Because Host Financial is rewriting the rulebook, tossing out those pesky DTI restrictions. They focus on your property's income potential. No tax returns or personal income statements needed. Simple, efficient and tailored for investors like you. Imagine a lender that sees the gold mine in your property, not just the numbers on your paycheck. That's the Host Financial difference and they're approved in 47 different states, so your next big deal could be just around the corner. Ready to unlock your property's true potential? Visit hostfinancial.com don't let old school lending hold you back another day. That's Host Financial Landlords Here's a quick tip.
D
A standardized checklist for property inspections can save you time, money and headaches. Preventative maintenance means fewer expensive surprises later. Want to save even more? Rent Ready helps you stay on top of rent collection, lease management and maintenance requests all in one easy to use platform. And right now you can get six months of rent ready for just $1 with promo code BP2025, visit rentready.com that's R E N T R E D I.com and use code BP2025 to get started.
A
Okay, welcome back. Our next question is from Taylor in the BP forums. I'm a brand new investor with little to no real estate experience. My wife and I are moving back to Birmingham this summer and I am planning to invest in real estate. When we do, in your opinion, what is the best job that will teach me the skills necessary to be a real estate investor? Little Background My wife is a high income professional in the medical field and I am an educator. Our plan is for me to leave the teaching field and invest in real estate full time when we return to Birmingham this summer. I don't have any work experience in real estate, but I started reading and trying to learn what I could back in 2020. I've read a few of Brandon Turner's books and a few others, about five or six in total. So I would like to obtain a job in real estate where I could work full time while we begin buying rentals. Our Initial strategy is to buy single family homes for buy and hold long term rentals in or around Birmingham. We are looking at buying at least one home per year for the next 10 to 15 years. I assume our plan can and will evolve over time as we are interested in small multifamily as well. So back to my question. What would be the best job for me to gain valuable experience? After a little online research it seems something in acquisition so that I can learn to analyze deals or property management so that I can learn the day to day operations. What would be the best position fund thoughts? I actually have a hot take on this. I think.
B
Yeah, oh, Ashley's got a hot take. We need like a hot take, you know, sound effect or something. What take?
A
I don't think that's what you should be concerned about. I don't think that you should worry about that. I think you should take the highest paying job to increase your income, to increase the amount of money you have to invest in real estate. And also that gives you the time to invest in real estate. So I would say being a teacher, okay, if you were to keep, you know, a teaching job, teachers can be well paid. I will say it's not the highest paying job for the amount of work that they have to do. But you're working school hours, you're getting vacation days off, you're, you know, over holidays, you're off during the summers. So if that is like a better paying job than working at a property management company where you're working 40 hours a week for the whole time throughout the year, maybe keeping a teaching job is actually the better solution for you. So I think I, the reason, I think that is because you don't need to learn a skill set to actually invest. I do think it is very valuable to get paid to learn. That is how I started. I did, I worked as a property manager for an investor and I learned everything and felt it definitely gave me the confidence. But I don't think that you need to do that or that it's going to set you apart than someone who isn't doing that. I think you are still as capable of learning everything online at your home without actually physically working that job. If you are set on getting a job that's in real estate, I would say not a real estate agent, it's not consistent enough. You're going to Most likely be 1099. It's not going to help you get loans for, you know, investment properties, property management. You're. Unless you're in a lot of states if you're not a licensed real estate agent, you can't actually be like a property, property manager, but working in the office you'll probably, you know, you'll have access to the lease documents, things like that. What I would suggest instead, instead of getting like a full time job, I met someone who went and worked as one of the, I can't think of what it's called but they would like be the person that answered the phone for work orders and assign the work orders to people and so they'd move to their full time job to doing that. What I think what you could do instead is keep your consistent job as a teacher, maybe pick up a shift a night or on weekends, leasing an apartment or you know, doing maintenance on a property. I had met a sheriff before who he, as a part time job would do maintenance on properties. The investor that owned the properties would text him, this was before there was great property management software. Text him, here's your. The work orders that need to be done. And then he would schedule them and set up times that worked for him to go and meet the tenants and complete the work orders. So I would say like, if you can get paid more money to switch careers into something that's like in the property management field, even project management, usually you need to have some sort of experience or a project management degree. To get into a field like that can be super beneficial, especially if you're going to be doing rehabs, maybe even in construction, you know, working for a builder or something like that where you're learning more about the rehab process. But I would say my recommendation would be to keep whatever job is going to be consistent income for you and that you enjoy too. But property management, you just hear complaining all the time, it's not enjoyable and then try and pick up something on the side or just your part time job is going to be just mentor, shadowing an investor or something, not even get paid to do it. So I think there's many other options rather than just like completely switching careers.
B
Ash, I'll, I'll agree with you, but I'll also disagree with you and, and I think the advice you gave I would agree with for most people. But there's a caveat to what he said that I think is, is important. He said my wife is a high income professional in the medical field. So it kind of sounds like his wife is able to hold it all down for like what they need for their life and everything. So I actually do think that in that unique situation, him going and taking a very you know, kind of riskier job in the real estate space might actually be a really good idea. And for me, I feel like most investors like, like if I was in his position, I would try and go find like the biggest wholesaler in my market and go work for them. So I can understand how to build deal pipeline, like how to build my pipeline of deals. Because whatever strategy you end up wanting to go into, the ability to find a good deal is foundational to be able, being able to execute doesn't matter if you're flipping long term, buy and hold, short term, midterm, whatever, name it, you still need a good deal in order for these, these, you know, for these deals to work. So I think only because he's got the spouse who's a high income earner, they can, it seems like, take care of everything. I would invest all of my extra time, effort, energy into getting really, really good at finding the best deals and then scaling up from there.
A
If you guys are watching this on YouTube, let us know in the comments which way you would take if you were this person or if you totally disagree with both of us and have your own solution, let us know in the comments.
B
Right, so from your perspective, if you think about all the different pieces that go into like making a real estate transaction happen from acquisition through management and everything in between, for a rookie, which one do you think they should focus on most or first?
A
Maybe that's a good question. Like I do think that acquisition piece is important, but I do think like there's so many investors that are successful that don't have to acquire property from scratch like that you can use a real estate agent to walk you through that process to find a deal for you to, to help you with all that. Or you can buy from a wholesaler. So I think it really depends on the person and what their goal is in real estate and what they want to actually get into. Like I have no interest in going and soliciting off market deals by cold calling or texting or door knocking. So I mean I wouldn't take the time to learn how to do that. Like I've sent mailers before, I do a lot of off market deals just from referrals, things like that. But I am not physically out there soliciting deals. So I think that that makes a big difference, that it's not useful for me to learn too much into how to spot a motivated seller, things like that. I definitely do think it's a big thing and probably can propel you and 10x you and get you better deals. But I, I don't want to put the time into that. So I don't know what I like. For me, property management definitely was really useful. I think it gave me like the confidence of like not being scared of, you know, actually managing the tenant and knowing what to do and things like that. But I actually, you know what, I, I'm changing my mind. I know it would be the best thing, handyman skill set that I think would be the greatest, one of the greatest things if I was getting started because I think that's like one of the biggest. Not feeling confident about doing the rehab on the property, not feeling confident about getting maintenance things. So that's what I would do.
B
You know, I like the handyman idea, but I think your initial point, Ash, is maybe even more important because what you're basically saying is you've got to understand who you are as an individual, where your natural kind of skills and abilities lay. And what, what do you really want to focus on as you become a real estate investor? Because you're right there, there are successful real estate investors who do just use, you know, networking with agents and wholesalers to go out there and find all their deals so they can focus on the other element. So I, I guess you've got to ask yourself what part of that, you know, cycle of a deal do you really want to be, be focused on and build your expertise in and then probably go, go do that. So yeah, it's a great point, Ash. I guess the answer does kind of vary depending on the unique individual.
A
And like, for me it was property management. But also like it's so easy to hire a property management company. So if you already know you're going to do that, it's not worth your time. So maybe asset management is the best answer. Knowing how to manage your assets, you.
B
Know, like for me I, I'm good at property management, but I don't like it. You know, like I do not like being a property manager. That's why my wife handles most of the day to day in our real estate business. But I do like underwriting deals and you know, kind of building that pipeline and doing that piece first. So yeah, I guess it does kind of depend on where your, where your skill sets lie.
A
I have to say, for short term rentals I do not like it either. Until I finally grew up and got like good property management software. And now that I use Hospitable, I love it because it like does everything for me. So I like feel like I'm so accomplished as a host of my Rentals now but literally just because it's doing all everything for me.
B
Shout out to the Right tools. So guys, DM me and Ashley on Instagram if you want like all the tools that we use because it makes a, it makes a big difference in being able to run both your long term and your short term rentals the right way. So there, there's plenty of them out there.
A
And again, if you're watching on YouTube, tell us your favorite tool for investing because I am obsessed with software apps, anything that will help me run my business. So I'd love to see what are some of your guys favorites.
B
All right guys, so we talked about where to get started but what happens when you actually find the deal? At some point you gotta pay taxes. So how do you navigate the world of taxes? A real estate investor? We'll cover that right after we're from.
A
Today'S show sponsors Thinking about wholesaling or flipping your first property, but not sure where to start? The truth is deals don't just fall into your lap anymore. You need to go out and create opportunities. That's where Propstream comes in. With Propstream, you get instant Access to over 160 million properties nationwide. Use 20 rebuilt lead lists such as pre foreclosures, tax delinquencies and vacant homes to find motivated sellers fast. And now Propstream has integrated batch leads and batch dialer to provide you with a complete all in one solution. That means you can not only find motivated sellers, but you can also reach out right away. Skip trace phone numbers free on select plans, then send postcards, emails or call sellers directly. Don't worry if you're new. Propstream also gives you AI powered insights and comps that are over 99% accurate so you know you're making smart offers. Plus, you'll have access to Propstream Academy to guide you step by step. Start your seven day free trial and get 50 free leads at propstream.com BP that's P R O-P S T R E A M dot com BP don't just dream about real estate. Make it happen with PropStream to tired.
C
Of traditional lenders holding you back? Host Financial is here to change the game. They've ditched the DTI restrictions and they zero in on what really matters. Your property's income potential. So no more chasing papers for tax returns or personal income statements. Think about it. A lender that values your property's worth over your paycheck, that's the host financial difference. Approved in 47 states. They are ready to help you make your next big move. Curious if you qualify? Just head over to HostFinancial.com and find out. Stop letting outdated lending practices hold you back. That's HostFinancial.com where your your property's potential meets Unlimited financing.
D
Inspecting your rentals again? Here's a pro A simple checklist makes sure nothing gets overlooked. It saves you time and costly repairs down the road. And when it comes to managing your rentals, RentReady makes everything easier. Rent gets paid on time, leases get signed online, and maintenance requests don't get lost in your inbox. And if you're a BiggerPockets Pro member, I've got great news for you. RentReady is already included in your membership for free. Don't leave it sitting on the table. Log into your BiggerPockets Pro account and start using rent Ready today.
B
New year Same extra value meals at McDonald's. So now get two snack wraps plus fries and a medium soft drink for just $8 for a limited time only. Prices and participation may vary. Prices may be higher in Hawaii, Alaska and California. And for delivery. All right guys, we are back with our final question of the day and this one comes from Daniel in the bigger pockets form. And Daniel says, I'm looking to hire a professional to help me with my taxes this year. I've always done them myself, but I fear I'm leaving money on the table. I have W2 income and I own three properties, all long term rentals that I've had for a few years. Are there any questions that I should be sure to ask or anything that maybe you wish you had asked sooner? Looking forward to hearing from you guys. All right, that's a great question. And we are recording this right at the end of the year, but this will release beginning of the year. So it's actually a great time to, to talk about taxes because I think a lot of people wait, you know, until that spring deadline to start thinking about taxes. But really you should be thinking about taxes on January 1st for that entire year, not the following year when you're going to file. We, we got our first cpa. Not, not at our first deal, but it was within like the first, I don't know, 12 months or so because by the time I filed my first tax return, as someone who had several properties, I did have a good CPA that I was working with. I think the first thing. And Ash, let me know if you disagree with this. I think the first thing that you should ask whatever CPA you go work with is what percentage of Your clients own real estate, and you don't want to get into a position where you're educating your CPA on things like bonus depreciation or cost segregation studies or, you know, different deductions you can take as a real estate investor. So for me, I think that would be my first question when I'm going to, to, you know, vet someone as my potential CPA is not, do you work with real estate investors? But, you know, what percent of your client base right now are in real estate?
A
I think that's a great question for any vendor. Like, you know, if you're looking for an insurance agent, if you're a real estate agent, how many investors do you work with? I think that's a great thing. Even contractors, like a contractor that I've used a lot, he really only does stuff for investors or he has his own investment properties. So he's very like conscious that, like, this is a rental, this isn't like my dream home. And we don't need to go over the top with finishes and things like that. So really can make a big difference with using a cpa. I think there is some level of knowledge that you need to have, like, of course you want to hire the right people so you don't have to learn all of these things. But BiggerPockets does have a couple books on tax strategies for real estate investors by Amanda Hahn and Matt McFarland, which I think are a great read just to like, give yourself the basic knowledge. So that way when you are going to your cpa, you have some knowledge about what they can offer you and also to be able to ask these right questions. So, for example, I worked with the CPA for a long time that never ever told me about a cost segregation. Now I know to ask, how many cost segregation studies have your clients done, you know, in the past year or have you done on their tax return or whatever? I think that just having that basic knowledge of what opportunities, tax loopholes, deductions are out there can really, really help you have that conversation with the CPA to see if they are a right fit. Because if they don't know what some of these things are, that's probably a red flag.
B
I think another one for me to call out is like your, your entity structure. And it's good to give advice both from a CPA and an attorney on this one because they're both trying to optimize for different things. But I'll give you guys like, like an example. The first CPA that I hired, we were flipping homes and we were holding real estate and we were doing it all together. And she's like, no, no, no, no, you do not want to do that. Because. And I can't even remember the reason, you know, like something about, you know, employment taxes or something is like you're getting double tax if you're, you know, running, you know, active income through a passive income and see, like, it doesn't work. So she encouraged us to split it out. So now even to this day, we have one entity that we hold all of our real estate in, right? So all of our buy and hold rentals are in one. Anything that we flip or any of our other active income is in a separate entity. And there was a tax advantage to doing that and she was able to share that with me. So I think just sharing with your cpa, what are your current. You've got three rentals right now, but are you doing anything active? Do you flip as well? Do you wholesale? Do you have any other active income that you're doing to make sure that they can give you some, some insight there? I think another one that's important too is just like exit strategies. Because sometimes maybe you're thinking about selling a property and just having that conversation with your CPA beforehand so they can give you advice on, okay, you bought it for this much. You actually depreciated this much already. You know, if you sell this, here's what you're kind of looking at from a tax perspective. But if you 1031 it, then, you know, here's the benefit of doing that. So I think just keeping them in the loop about not only where you are today, but what your plans are for the future. So they can give you advice on how to make the right moves.
A
And you can also have two people help you with this. But I know you mentioned the attorney. But also like, you don't have to have one CPA that does everything. You can have a CPA that files your tax return and you could have a different CPA that does your tax planning that helps you with this going forward. So, like, they're the ones that are really focused on like, what moves you need to be making, knowing what you're going to have happen. So they can have you do the right things before the end of the year so that when you do go to file your tax return, you have all of the information that you need for the other CPA to put onto the tax return. And I've actually found this to be like, cheaper kind of is to like not have the really skilled person do all of it where they're doing the fine tuning, they're putting it into a package for me of how this is going to be the best tax strategy. And then basically I'm giving the other CPA the fill in the blank information on my tax return, because that's what a tax return is. It's fill in the blank. And then, you know, each year the tax planner actually reviews, make sure it's correct, things like that. So that's another thing too is you don't have to rely on just one person. And it really helps having two people because if there is something that one person brings up, you can talk to the other person about and see what actually is the best benefit to you.
B
That's true. That's actually how we started as well. We had someone for tax strategy and someone else who's doing the actual preparation for us. And on that note, then I think the other question you should ask the CPA as well is like, how often are we meeting throughout the year? Like, am I just meeting you, you know, like the, the first week of April, you know, when I sit down with you to, to do everything, or are we meeting multiple times throughout the year? And ideally, probably like a quarterly cadence, I think is good for you and your CPA to meet to make sure that they can stay up to, you know, up to speed on what you're doing throughout the year and help you plan to make sure that by year end you've done everything within that calendar year to optimize that year's tax returns. Because if you're, you know, if you're, if it's 2027 and you're now filing your 2026 taxes, well, if you're sitting down in, you know, April of 27, it's too late to really change much about 2026. So the goal is that throughout 2026, throughout that year, you can make those changes, make those decisions that will make that tax prep in the next year a lot easier. So I think that's an important one as well. How often are you guys going to actually meet?
A
Well, thank you guys so much for joining us today on Ricky Reply. I'm Ashley, he's Tony, and we'll see you guys on the next episode.
D
Okay, we're going to shift gears for a minute to cover something important, especially for new landlords. The shows often talk about getting stuck doing everything ourselves and the cost of sweat equity. The key question is simple. Is my time better spent elsewhere? I use a tool that cuts down on a lot of landlord hassles. And the wild part is it's just $12 a month. It handles rental screenings, rent collection, maintenance requests, and accounting all in one platform via a mobile app or desktop. It saves me time in tenant communication and keeps me organized for tax season. It's called Rent Ready and you can sign up for a six plan for just $1 with promo code BP2025. Pro users get it for free because we believe in it. Just sign in through your Pro account to get started. Rent Ready helps ensure on time rent with auto reminders, keeps communication professional, and lets you post listings to multiple sites. Check it out@rentready.com BiggerPockets that's rent R E D I.com BiggerPockets hey rookies, if.
B
You'Re watching this, we want you to apply to be a guest on the Real Estate Rookie Podcast. That's right, and 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.
A
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.
B
So head over to biggerpockets.com guest if you want to be a part of our show again. That's biggerpockets.com com guest and we'd love to have you on.
Hosts: Ashley Kehr & Tony J. Robinson
Release Date: January 9, 2026
Podcast: Real Estate Rookie (BiggerPockets)
Episode Goal: To answer listener questions on how new investors can navigate high interest rates, learn key skills, and optimize taxes to still build cash-flowing rental portfolios in 2026.
Ashley and Tony answer three common rookie investor questions:
Their tone is practical, encouraging, and candid, aiming to reassure rookies that real estate investing is still possible—and profitable—with smart adjustments and planning.
Question:
Ray from the BiggerPockets forums worries that high rates make cash flow impossible and wonders about using a HELOC or Roth IRA to fund rentals.
Markets & Strategies Matter More Than Ever
“So the question isn’t ‘Can I get cash flow?’ The question is ‘What market, what strategy, what niche should I be focused on?’ ...it’s the combination of those things that’ll help you find the cash flow.”
Look at All the Benefits, Not Just Monthly Cash Flow
“What if that same exact property could actually decrease you not having to pay $20,000 in taxes that year? ...That’s a little over $1,000 a month back in your pocket that you’re not paying in taxes… That’s what took me a long time to realize.”
Adjust Your Expectations for Cash Flow
“The people who say now is not a good time to buy are probably never going to get started... The right time is always ‘how can I adjust my strategy and expectations to the current market?’”
Key Takeaway:
Yes, cash flow is possible in 2026—but you must target the right markets, use creative financing, and appreciate the full benefits of real estate ownership, not just monthly profit.
Question:
Taylor, a teacher, is moving to Birmingham and asks what job (acquisition analyst, property management, etc.) will build the skills to become a full-time investor.
Ashley’s “Hot Take”: Get the Highest-Paying, Most Flexible Job
“I don’t think you need to learn a skill set to actually invest… You are just as capable learning online from home.”
Tony’s Counter: If You Have a Financial Safety Net, Go All-In
“If I were in his position, I’d try to find the biggest wholesaler in my market and go work for them... The ability to find a good deal is foundational for every investing strategy.”
What’s the Most Useful Skill or Experience for Rookies?
Key Takeaway:
There’s no single “best” job; maximize income and flexibility, and supplement with experience where possible. Skills in deal finding, property management, or handy work all help, but self-awareness and a supportive job situation are most important.
Question:
Daniel has W-2 income and three rentals. He wants to ensure he isn’t missing tax savings by doing his taxes alone and asks what he should discuss with a CPA.
Choose a Real Estate-Savvy CPA
“You don’t want to get into a position where you’re educating your CPA... For me that would be my first question.”
Self-Education Is Crucial
“I worked with the CPA for a long time that never told me about cost segregation. Now I know to ask, ‘how many cost segregation studies have you done for clients?’”
Ask About Entity Structure and Planning
“Share with your CPA not only where you are now but where you’re going so they can advise you on making the right moves.”
Consider Multiple Advisors
“You don’t have to rely on just one person. And it really helps having two because if there is something that one brings up, you can talk to the other about.”
Prioritize Frequent Communication—Don’t Wait for Tax Season
“How often are we meeting during the year? …If you’re waiting until April, it’s too late to really change much.”
Key Takeaway:
Proactively seek out tax professionals who understand real estate, learn enough yourself to ask sharp questions, and make tax strategy a year-round habit—not just a spring afterthought.
Tony on filtering advice (10:35):
“If the folks who are telling you ‘don’t buy real estate’ are people who’ve never bought real estate… you gotta kind of filter that advice out.”
Ashley’s “aha” moment (07:53):
“I was like in shock when I just looked at this property I bought in 2017 and what it’s worth now… So much more value than just the cash flow.”
Both on personality fit (22:40 & 23:43):
Ashley: “For me, property management gave me the confidence… But it’s so easy to hire a property management company, so maybe asset management is the best answer.”
Tony: “For me, I’m good at property management, but I don’t like it.”
Hosts Sign Off:
"Thank you guys so much for joining us today on Rookie Reply. I'm Ashley, he's Tony, and we'll see you guys on the next episode." (34:56)
For further resources, visit BiggerPockets.com, and consider Amanda Han and Matt MacFarland’s tax books as recommended by the hosts.