5 Things We’d Do If We Were Starting Over in Real Estate Today

0:00Tony:If we were starting over in 2026, we wouldn't be looking for the perfect market, the perfect strategy, or the perfect deal.

0:07Ashley:We'd be focused on one thing, making the decisions that actually get a rookie to close on their first deal instead of staying stuck in analysis paralysis.

0:22Tony:This is the Real Estate Rookie Podcast. I'm Ashley Kerr.

0:25Ashley:And I'm Tony J. Robinson. And in today's episode, we're going to focus on five key things that we would do if Ash and I were starting over in our portfolio today. And the goal is that for all of the Rickies listening, you can take these five things, implement them into your strategy to make sure that you're, by the end of this year, hopefully one of the folks we can bring on as a guest to the podcast, say, hey, I listened to this episode and now I'm the proud owner of my first real estate deal. So five key things. The first thing that we do is we'd start by asking the right questions. And what I mean by this is that oftentimes we see rookie investors who just are kind of focused on the wrong thing when they're starting off their journey of real estate investing.

1:08Ashley:And sometimes it could be focused on steps that are maybe too far ahead. Like, hey, well, how am I going to buy my second deal? How do I scale? And then, well, okay, well, you haven't done your first deal. Why are you worrying about scaling today? Or what does the legal structure look like? And I need this holding company based out of the Cayman Islands and all these crazy things. And they're just asking the wrong questions. So the core questions that I would focus on first are, what is my time availability? How much time can I allocate toward my goal of investing in real estate? What is my risk tolerance?

1:44How much purchasing power do I

1:46Ashley:have, which is my cash on hand and my ability to get approved for a mortgage? And then what's my motivation? So time availability, risk tolerance, purchasing power, and motivation. For time availability, the reason that I start with this is because this is a limiting factor for the type of deals that you should be focused on. Now, I will put a big caveat to this is that I hear oftentimes people say that the reason they want to invest in real estate is because they want to at some point in the future, have the ability to have more control over their time. Because right now they feel like they don't have a ton of time, but they want real estate investing to be the thing that gives them more time.

2:24Ashley:But then in the same breath, they say, well, I don't have time to actually do all the work that's required to be a real estate investor. And if you hear that being said out loud, you can see how that's just like this closed loop where you're going to be stuck in this space of not having time, right? Because in order to do the thing that will give you the time. You need to be able to allocate some time, but you don't have time. So you can't start that thing. So you'll never, never be able to get out of that loop. So I think first you got to be able to make some sacrifices in your life to free up a little bit of time if you feel like you're truly maxed out.

2:52Ashley:But that's the first one is the time availability. The risk tolerance is everyone sleeps differently at night, depending on the kind of risks that they take on. There are some people who are totally fine with the super risky deals because they're like, Hey, I'm going to swing for the fences. And there are other folks who like, man, I just want to get on base. So I think understanding what your risk tolerance is and how easily are you going to be able to sleep at night as you take these first steps. The cash and your purchasing power is important because how much cash you have on hand and your loan approval amount will also dictate the kind of properties and locations that you can focus on.

3:30Ashley:If you've got a million dollars cash and you can get approved for a$5 million loan, you've got a lot of options. But if you've got$10 ,000 cash and you can get approved for$100 ,000, that limits more so what kind of opportunities you should be pursuing. So having clarity on that piece first, I think is really important. And then the motivation, we talk about this a lot, but understanding why you're doing this is super important because it makes sure that as you take steps on finding properties, finding markets, that it actually supports whatever goals you have in place. Because if you're doing this for appreciation, well, then you better make sure that the properties and the markets you're focused on do really well when it comes to appreciation.

4:09Ashley:If you're doing this for cash flow, well, then you better make sure that whatever opportunities you're looking at are really focused on maximizing cash flow. So understanding your motivations, I think, are first. So those are the big questions I'd ask.

4:20Tony:Yeah. The only thing I would add to that is don't get too caught up on pursuing your passion. And I don't want to sound like a buzzkill, like, oh, you know, you want to get away from your W2 job. It's not your passion. You want to feel fulfilled. You want to manifest your dreams. Like if your why is because you want to make money or you want to build the wealth, like, yes, at some point in time, that can probably be correlated to your passion. But if you want to expedite that, you really want to pick the strategy that goes in line with what Tony already talked about, but also where you have resources, opportunity, and advantages.

5:01Where you have

5:02Tony:resources, opportunities, and advantages. So for me, I worked as a property manager. The only person I knew that invested in real estate did long-term rentals. And those were my opportunities and my resource to get started. If I would have started in flipping or short-term I didn't have anybody around me that was doing that to ask for help, to guide, to follow me or for me to follow them. It would have taken me a lot longer to be successful if I didn't have these advantages and opportunities already in place. And I was able to build a really solid foundation by sticking as to what was actually the path that would give me the most progress towards this wealth building.

5:54Tony:So that's something you should be thinking about too. If you're thinking about buying a deal in 2026, don't get too focused on what your dream job is or your dream investment. Think about what is going to build you wealth the fastest. And I don't want this to get confused by, oh, they're posting about self-storage and how you can make so much money. That's the way to make the most money. I'm going to do that. don't get caught up on the get rich quick. And I'm not going to say they're schemes, but I'm going to say that it may work for somebody to get rich and to build wealth, but that may not work for you.

6:34Tony:And it may not really be as quick as you think it is. They could have made$100 ,000 on that flip because for some reason, they ended up buying every single material they put into that house from a wholesale clearance place. And they did all the DIY themselves. They didn't hire any contractors. And you might not have the time to actually spend six months rehabbing a property and just shopping wholesale outlets to find the cheapest materials. So don't look at Instagram. Think about what is actually going to move the needle for you when you're picking a strategy.

7:14Ashley:Yeah. I couldn't agree more, Ash, about not focusing too much on what you see on Instagram. Obviously, the purpose of social media, a lot of times is to encourage you, inspire you, even this podcast to an extent, right? But you don't always see the hard work behind the scenes that goes into that. And you shouldn't make super big life decisions. And you shouldn't make super big life decisions based on a snapshot you see of someone's life on social media. So you really got to make sure that, again, you're asking the right questions, which is what we just walked through to help you make a more informed decision around what strategy, what asset class, what type of real estate investing makes the most sense for you.

7:52Tony:I mean, even right now for you guys watching on YouTube, here I am looking all glamorous and beautiful. But in reality, I got sweatpants on, a heated blanket on my lap, level four heating right now and slippers on. So you never know what's actually going on behind the camera on YouTube, Instagram, things like that. So once you stop asking the wrong questions, the next mistake rookies make feels productive, but it's the reason most first deals never actually close. Next, we're going to talk about why chasing the best deal keeps you from buying any deal. Starting something new is terrifying. When I launched my business, I kept thinking, what if I fail?

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10:24Tony:Welcome back. Once rookies get clear on their situation, the next trap shows up immediately. They start hunting for the perfect deal instead of one they can actually execute. So number two is we pick the boring deal that still moves the needle. Yeah, I am too tired. I'm too exhausted to be chasing the perfect deal. And the longer you wait to actually get started, the less time you're actually building equity in a property. And that is really the opportunity that I have seen over the last 10 years of buying properties and holding them and waiting and seeing all that equity build up. And if I'm spending the full year chasing the perfect deal, I'm wasting out on all that time of already getting baked in appreciation and mortgage pay down by my tenant.

11:17I'm wanting to take action on a deal that works.

11:21Tony:It doesn't have to be the best use of my money. And I see this posted in the BiggerPockets farms all the time. And it's a great question to ask. I mean, I ask myself questions like this every day, but it's like, I have$50 ,000. I don't know how to invest. What is the best thing I can do with it? And everybody wants to know where are you going to get the best value of your money or the best value of your time? And sometimes that first deal, it doesn't need to be the best and you don't need to overanalyze and get stuck in that analysis paralysis of like, I'm not spending this$50 ,000 unless I know that I'm getting the max return.

12:00Tony:And I've looked at every possible deal and every possible option. And that really is just going to stall you and delay you. So I'm not going that route. I'm going to look for a deal that works, even if it's not a home run deal and not super amazing. And if someone interviewed me, my YouTube thumbnail isn't going to be, cash flow is$5 ,000 on her first deal. It's going to be the slow and boring investment with Ashley Care.

12:29Ashley:My very first real estate deal, I think it was cash flow in like 150 bucks a month, something to that effect. That's not life-changing money.

12:38Tony:That's what I thought mine was going to be, but then I forgot to account for snow plowing. So it was even less.

12:43Ashley:Snow plowing. And now you're a break even, right? So I couldn't agree more. I think oftentimes if we just focus on that first deal being as boring and simple as possible, that simple decision will unlock your ability to actually get the first deal done, right? So I think boring and simple is often the approach that most rookies should take because there's a difference between a deal that looks good and a deal that you can actually close. Because, yeah, I can take you to the hoarder house that's got a bunch of deferred maintenance. It probably needs to be renovated down to the studs, but it's a really, really good deal versus a house that's mostly turnkey, has a tenant in place already that's slightly above a break even on cash left.

13:29Ashley:You account for all of your expenses and vacancy and outbacks and all those things. And the first deal definitely seems a lot better, but which one will you actually pull the trick around? Which one will you actually be able to execute on? The hoarder house is down to the studs or the turnkey property that you'll cashflow a little bit, which will cashflow on day one. So I think the goal is not necessarily just to look for the deal that looks the best, but it's which one can actually move forward on today. So to Ashley's point, instead of prioritizing a big home run, we want to try and prioritize this first deal, something that's clean and easy to finance, right?

14:00Ashley:Because oftentimes these big heavy rehab jobs are super complex things. They get a little bit more tricky on the financing piece. Simple to no rehab removes the big obstacle of having to manage a rehab for the first time. And something that's just like a very clear path systematically for you to move through to actually get the deal done. There's so much talk out there right now about different sexy strategies and subject to and settler financing and renting by the room and conversions to ADUs. And we've interviewed a lot of these folks with these different strategies in the podcast as well. So I'm not knocking those, but I am saying that those are slightly more involved than just the strategy of buying a house that's basically ready to go on day one that's got a tenant in it.

14:46Ashley:Or even if we want to talk about flipping, what's an easy way to flip a home or short-term rents? So it's an easy way to do it that way, right? Buy something that's tricky and closer to being ready. But I think just trying to move away from some of the super complex and overly sexy strategies to want it's a little bit more black and white, cut and dry on that first deal.

15:04Tony:I think like a great starter property is looking for, you know, a single family home or a duplex, a small multifamily that has, you know, a tenant in place. And it's somebody, you know, the tenant wants to stay there long term. and maybe the property isn't updated, but it's in good condition. If you could find a property that it's not completely renovated or up to date, but it's very well taken care of by the tenant, and maybe the tenant's already lived there for 10 years and wants to keep living there, that could be the easiest first deal that you ever have. Already having a tenant in place, it's already cash flowing from day one, even if it's only$150 a month, depending on how much of money you're putting into the deal.

15:50Tony:But you already have somebody in there that you know is going to take care of the place. Your chances of having a long-term renter in there are great. You don't have the cost of vacancy and turnover. And then you can just have your, know that you're going to save. And at some point, if the person does move out, then you're going to go ahead and renovate the property. Or over time, which I've done with tenants that say a long time, is like, I'm going to do an increase this year, but we're also replacing the carpets or we're going to repaint or we're doing this upgrade to the property too to justify why we're increasing your rent a little bit more than what we usually would.

16:34Tony:So I think that is also a great opportunity. I have a friend that did that. She invested out of state. And anytime I ask her, how's that rental doing? She's like, I think good. I mean, she just, she pays a rent and it was a tenant that lived there forever. It's just a little single family house. And you know, if there's a maintenance issue, she will, you know, just message about it. And then my friend calls, you know, someone to go out and take care of it. And that's it. And it's said and done.

16:58Ashley:Number three, the third big thing is we'd focus on financing early on. I think that one of the first questions that we kind of touched on this on the first point, but one of the first things that we need to understand is what kind of financing do we have access to? There are, I've used this metaphor, this analogy before, but the lending industry is a lot like the ice cream industry where I can go into different ice cream shops. I can go to Dairy Queen. I can go to Baskin Robbins. I can go to Cold Stone. And they all sell ice cream, but they all sell slightly different flavors. And it's the same thing in the mortgage industry where I can go to lender A, lender B, lender C, and they all sell loan products, but the flavor and how they deliver those loan products is slightly different.

17:45Ashley:So I think making it a point early on to try and talk with as many lenders as possible to understand all the different flavors of loan products that are available to you. That way you can identify, okay, what is the actual best product for the type of deal that I'm going after? Because the lender who really understands traditional single family long-term rentals is different than the lender who understands small multifamily. And that lender might be different than the lender who understands flipping. And that lender might be different than the lender who understands short-term rentals. And that lender might be different than the lender who understands large commercial properties and RV parks and motels and whatever it may be, self-storage.

18:23Ashley:So understanding the loan products that are best for the deals that are in front of you, I think is one of the big things that I would focus on as well. Because I've seen plenty of deals, get to the 11th hour with the lender who says, yeah, sure. I write loans like this all day. And then when it comes time to actually close, you're like, oh man, this is actually, you know, underwriting pushed back on this because of X, Y, and Z, or actually don't think I'm going to be able to get this loan closed. So having those conversations early on, I think is a big thing that Ricky should be focused on as well.

18:53Tony:Yeah. And even if you're not going with bank financing, you know, lining up your private money lender or where you're pulling cash out of, you know, from if you're borrowing from your 401k, like make sure you talk to your employer and you understand what the process is to actually get that money out. So one thing that I actually just learned with retirement funds is I didn't know this is with a Roth IRA, you can actually pull out, I think it was up to like$10 ,000 without like a penalty. And since it's a Roth, you've already paid taxes on it. So no taxes, but without penalty for a first time home purchase, So if you're looking to purchase your first home, you can actually tap into your Roth IRA and pull out$10 ,000 to put into a property.

19:40Tony:I thought that was cool. But anyways, have that plan in place of how are you going to actually access the money that you're going to need and use. There's been a lot of times where I've found a deal and then I've went and got the money. And And yes, you can absolutely do that, but it is so much easier to have the financing, have the money lined up first than to do it the opposite way. And it makes the deal goes faster and a lot smoother and less headaches and things like that along the way to actually get the deal done.