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A
If you've been learning about real estate but still haven't done your first deal, this episode is for you.
B
Yeah. Because a lot of rookies aren't stuck because they don't know enough. They're stuck because they don't know what to do next.
A
So today we're breaking down a simple 90 day roadmap to get your first investment property under contract week by week.
B
And this is based on the framework from real estate rookie 90 days to your first investment, which is the lovely book written by my co host, Ashley Kerr. And we're turning it into a practical checklist you can actually follow.
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This is the real estate rookie podcast and I'm Ashley Kerr.
B
And I'm Tony J. Robinson. And with that, let's get into the very first step, which is laying your foundation. So, Ash, what does it mean to quote, unquote, lay your foundation as a rookie real estate investor?
A
Yeah. Before you even think about analyzing a deal or finding a deal, you need to set your foundation and you need to understand why you're investing in real estate. What is your goal? What do you want out of it? And you also need to build a personal finance foundation. So when I say that it's, you need to be able to know where your capital is coming from. You need to understand finances, because a lot of investing is finance, okay. Whether it's stocks, whether it's a real estate investment. So there's all these things that you need to do ahead of time before you actually continue on your real estate journey. So let's start with first, why do you want to get into real estate? Because that can really shape and tailor what strategy you're going to do, how much time you're going to put into it, what deal you're going to find. Then what are your goals? Do you want to acquire one property in the next year? Do you want to retire within five years from real estate? Then your personal finance foundation, you want to be able to manage your own money before you're going to go and take on this business, this investment, and, and have to, you know, manage the money that this property is bringing in and the money that is going to go out from this property with the expenses. So I think those are really three things that you need to lock down and set a foundation for before we even continue on your journey to get a deal in 90 days.
B
Yeah. And I think a big piece of laying that foundation too, is just understanding what your motivations are because you can't optimize for all things equally. And like the biggest Things that we have to look at when we talk about investing in real estate or like, the biggest motivations are typically tax benefits, cash flow and depreciation. And it's not common that you can find a deal that equally satisfies all three of those. So it's important as you're getting started to understand what is it that I'm trying to optimize for and what is it that I'm willing to maybe take a little bit of a less, you know, quote unquote return on, because I'm optimizing for this other thing. So if you really want cash flow, then maybe those markets that are great for cash flow aren't as great for appreciation. But if you're in a situation where you love your day job and, and, and you're fine with what you do day to day and you're really investing for retirement, well, then that, that strategy looks a little bit different. So I think just having a really clear picture on not only what are your motivations, but how would you rank them from most important to least important.
A
And we're going to give you a couple action items as we go week by week. And the first thing I want you guys to do is block time on your calendar right now, you know, maybe two to three hours. And this is where you're going to sit down and you're going to answer all these questions. You're going to define your why, you're going to understand your goals, you're going to set, you know, you know, the foundation. A really great dashboard that I use for my finances is Monarch Money. And so, like, I can get a picture of my own finances and know where my money is coming in and out, but I think sitting down and actually thinking about this and putting it in writing, whether that's typing it up on your computer, whether that's writing it down in a notepad, a journal, but actually taking time to really put that vision together of what real estate is going to do for you and where you want it to take your, your finances in general.
B
And I think the last piece that I would say is that you've got to identify what your strategy and your niche is. When I say niche, I mean, like, what asset class or what type of real estate do you want to buy? Do you want to buy single family homes? Do you want to buy small, multifamily? Do you want large multifamily? Do you want mobile homes? Do you want. Man, we've had people flip and sell and buy all kinds of things, manufactured homes. We interviewed A guest who all she did was buy manufactured homes. So identifying what type of property you want to buy, and then what's your strategy that you're going to layer on top of that specific niche? So I can go out and I can flip single family homes. I think that's what most people associate flipping with. But we've also met people who go out and they flip nothing but condos, right? Like that's a different process than flipping a single family home. Or at a larger scale, people who flip apartment complexes, they buy them, they renovate them, then they sell them, you know, 12 to 24 months later. So understanding not only what your niches, but what strategy makes the most sense for you on top of that niche.
A
And after you decide what investing strategy you're going to do in that niche, we actually have a buy box resource for you guys to help you build out even, even more detail as to what strategy, what type of property you actually want to purchase. And this, when you get further down the road into deal analysis, will really help narrow down the type of properties that you analyze to really cut out the fluff. The properties that you know you don't want or don't make sense anyways. So you can go to biggerpockets.com resource and you can check out the resource hub there. We have beginner resources, tons of things, but you'll find the buy box there, among other things.
B
So once we knock that out, Ash, when we got the foundation laid, the next piece or the next big step is choosing the market to invest into. And I think I'll open this point by saying that the biggest mistake that rookies make when it comes to choosing a market is they fall victim to the Goldilocks syndrome where they're looking for the city where everything is just right, everything's perfect. But in reality, guys, there are 20,000 plus different cities across the United States. So chances are there's not just one city that's the best city for you to invest into. There are hundreds, if not thousands of cities that would make sense for you to invest into. So the goal isn't to necessarily identify the one city that is the absolute best for you. The goal is to identify multiple cities that align with your goals and support what you're trying to do as an investor. So I think just switching that mindset from the beginning is a big change that most rookies need to make.
A
So as we're identifying a market, we have a ton of resources also for that. You can once again go to the resource hub, but also on BiggerPockets, we have a find a Market section. So you go to the top of the page, you can click on Find a Market and this will actually walk you through finding a market that works for what you want and what you're looking for and will give you the data and the statistics on that market. Another great resource is Neighborhood Watch, Bright Investor and even ChatGPT. Just putting in, you know, a prompt as to I'm looking to invest in this market. Can you please tell me this specific data about the market? So you know you're going to be looking at job growth, average home prices, average rents, how do the property taxes compare to other states, how do the landlord tenant laws compare? So you're going to gather all of this information. The really hard part is if you have no idea where you're going to invest, what market you're going to invest in. And is I just picking out of the millions of markets that are available out there. So I think a really great resource is to find like top 10 list to go into the Bigger Pockets forums. Look, where are other investors, you know, getting deals? Where are they making it work on social media? But I say this with caution. Just because you're going to go, it works for somebody else in a market doesn't mean that it's going to work for you. These are just starting points somewhere for you to start to start looking at these markets and then you're going to go and you're going to verify and you're going to do your own due diligence to make sure that market works for what you want to do. Tony invests in Joshua Tree. I have long term rentals. If I see Tony's successful there, I'm going to go and look for a long term rental. Tony, I'm probably not going to be successful buying a property there and listing as a long term rental. Correct.
B
And same for me, like if I tried to go into your neck of the woods and put a, you know, a really crazy short term rental, you know, next to the cow farm actually maybe that would do well. That actually might do well. So that actually might be a really good idea. So ignore that point. But you guys get where I was trying to go with that.
A
You can open the windows in the morning, get a beautiful draft of manure. Actually that's an add on. And do you want fresh manure or liquid manure? There's two different.
B
I didn't even know that liquid manure was a thing so I just learned something new about it.
A
The worst I can Handle like fresh manure but liquid manure when they sounds.
B
Like something to make yourself crawl. Oh my goodness.
A
So okay, now we need somebody to tell us in the comments if they are, you know, making it work with a high end luxury short term rental next to a farm. Okay. So now that you've we analyzed and looked at markets, once you've actually selected a market or maybe you've selected two or three, you're going to start looking at the listings. You want to look at at least five to ten active listings for this week. So we're into week four at this point. Okay. And you want to even more than that will be better. And even though you could look at the listing and say I already know this isn't going to make sense, practice analyzing them. Look up what the rent would be for each property, estimate the expenses, what would the insurance cost be. This right here, another great plug of why I love Biggerpockets because they actually have an insurance estimator on the website. So I think it's like under analyze deals section and you can go and you can just put in the property information and it will give you like an estimate of what the insurance would be. Also too now that you, you can use the deal calculators from bigger pockets and if you don't have a I think you get like five free Tony the calculators to use to analyze. If you need to use more than that, which I highly suggest you can use Ashley or Tony. I think either one of our names will give you 20% off a pro membership. But you're going to pull these listings and you're going to practice analyzing these deals. And after looking at the deals you're going to get a really good kind of foundation as to what works in this market, what doesn't work. Maybe a duplex is actually better than getting in a single family or you know what, all of these don't work at all or not even close. So being able to compare these properties, you could even go as far as like every deal you analyze, take the calculator reports, start a spreadsheet writing down what you notice, what worked, what didn't work and start writing down those patterns that you notice. And that can actually help you really tighten up your buy box too.
B
We've covered the first few steps you need to take to get your first deal in the next 90 days. We're going to take a quick break and when we get back we're going to talk about the numbers associated with buying that first deal. So we'll Be right back afterward from today's show.
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B
All right, guys, we're back. We talked about laying your foundation. We talked about finding the right market. But now once you know where to go, you've got to find the deals within that market to actually buy. And that's where we get to our next step. And this will take you about two weeks, which is the actual analysis of deals in that market. Now, my strong recommendation to everyone is to challenge yourself to analyze a lot of deals in a very short period of time. You could do seven deals in seven days. I like the idea of 30 deals in 30 days, but the goal is that most people do not find deals simply because they're not analyzing or underwriting enough. And if you can compress a lot of activity into a very short period of time, you increase the likelihood of you actually finding a deal. So that's my challenge to you. 30 deals in 30 days. Now how do you actually build that skill set of analyzing deals? Well, we've got the calculators in the Bigger Pockets website, which are great tools to show you what data needs to go into it. But in terms of finding the data and it'll vary from strategy to strategy. So I'll like, I'll hit on short term rentals, right. I like to look at things like average daily rate and occupancy and overall revenue and expenses and cleaning fees. And we put all those together to try and understand what the revenue and the expenses and profitability might be. Ash, what about for you on the long term rental side?
A
Yeah. Well, the first thing I wanted to bring up, Tony, is with the real estate Robinsons, you did 30 day deal analysis challenge before, didn't you? And what was the result of that? Like, how beneficial was that?
B
Every time we do that, we find that someone is under contract on something. Right? Like without fail, when you can compress that much activity into a very short period of time, you are almost guaranteeing that you'll find something.
A
So on the long term rental side, one thing that I've always struggled with when I first started out was like missing expenses and not having them. So I think like following the deal calculator is really beneficial because it literally tells you all of the expenses that are in there. But then also looking at, you know, like it's not going to say snow plowing specifically because that's very market dependent. So that's where it pays to go into the bigger pockets forums, to go into Facebook groups, to ask in the market that you're investing in, what are some other expenses that I'm not aware of? Another thing is to look at the property and understand where any other expenses could come up. So like if you have a pool, okay, so you may need to have pay for somebody to maintain the pool. Your insurance may be more because you have a pool. Looking at the, you know, if there is some kind of water system in the property that needs to be upkept in or the furnace filters need to be changed, are you going to be paying for that or the tenant's going to be paying that for that. So there's a lot of additional items that you may not think of for a long term rental just because it's, oh, I got my mortgage payment. The, the tenant is taking care of everything else. But make sure that is written into your lease agreement then. Or if you're inheriting tenants, make sure you understand from their lease agreement what they are and aren't responsible for. Because like if you find out they're actually not replacing the furnace filters and you have to replace those every six months. If you find out they're not buying salt for the sidewalk, if you, you know, all these other little things that need to be done to upkeep your property. We do have a recurring property maintenance guide in the Resource Hub also. And this guide goes through things like cleaning out gutters, when should you do it? You know, the maintenance on your furnace, your hot water tank, all these little things that you probably do as a homeowner, but you may not think of as your rental property because somebody else is living there and it's like out of sight, out of mind. Not that you mean to ignore the property, but you're not living in it day to day to look and say like, oh man, that furnace filter is getting filled. I need to, you know, replace that. So those are some of the challenges that I have experienced when analyzing deals for long term rentals is not thinking of all those little nuances that come along. So practice, practice, practice your market and then going to your meetups, connecting with other investors and you know, find somebody that will look over your deal analysis that's in your market. Tony and I could sit here all day long and you could give us your calculator reports, your deal analysis and we could look and point out at things, but there are going to be things that we don't know about your market that somebody who is investing in that market will know way better and know more about and say these little nuances and things like that and be able to point them out to you.
B
I think the last thing I'd add to the underwriting is that you have to understand that the first several deals that you analyze, it's going to take you a, you know, painstakingly large amount of time to actually get through those deals. But as you do more, the time it takes you to do one is going to be this much. If you're listening to this, my hands are very far apart right now. And by the time you get to deal number five, it gets a little bit smaller. By the time you get to deal number 10, it gets even smaller. By the time you get to deal number 20, you're now flying through this because you've already analyzed 19 other three bedroom, two bath properties in your specific zip codes. You have a sense of what the revenue is, what the expenses look like. So now you're kind of flying through it. So you've got to, you got to build that momentum, build that flywheel, really trudge through those first five or ten. But by the time you get to again, 15, 20 deals analyzed in a specific market with a specific buy box, you'll be flying through it.
A
So then after that we're going to head on to building your team. So some of the important team members that you'll need is if you're going to do finance, you're going to need a lender or a private money lender. Wherever you're getting money from, to actually purchase the property, you need that person on your team. You could need a wholesaler or real estate agent, depending on how you are purchasing properties. Even if you're doing it off market, like if you're in New York, like me, you need to use an attorney to close. So you'll need an attorney on your team. You'll, you could need a title company. So building your team, you can go to biggerpockets.com team and we have Connections with these team members, accountants, bookkeepers, lenders, anything you can think of for real estate property managers that we can connect you with in your market. You basically like a matchmaking service so you can go and check that out. If that's something you are missing, then another thing is asking for referrals, connecting with other investors in that market, in that area, putting it on your Facebook. You never know who you're friends with on Facebook that is also an investor. So then you start making those connections. Reach out to a real estate agent, reach out to an insurance agent, reach out to a contractor and handyman. And I know this may be awkward as to you don't even have a deal yet, but like starting that process with a contractor or insurance agent. But still, an insurance agent could be the person that you have for your home and auto insurance and you already have an established relationship with them. A contractor, handyman. Just for getting an idea, just call them, let them know what you're trying to do and that you're looking for a handyman to take care of a property. Once you get in under contract and see if that's even something they'd be interested in. What are the rates, things like that ask for, start building a list. So like Daryl's super good at this. Whenever we see like a truck or something that has, you know, like Tony's painting company, he'll take a picture of it and you know, it usually has the website or the phone number and he then he has a little spreadsheet that he updates and then eventually I put it in Monday.com because he likes his spreadsheet better. But we just have this whole list of contractors and like huge majority of them we've never even used, but we have them there and we just keep this database of contractors if we ever need them.
B
Great minds think alike. I have a iPhone album where like as I'm driving, I just snap photos and I save it to that specific album. And that's how I, how I add folks to my, my Rolodex. But also on the Bigger pockets website, you guys, we have the agent finder, the lender finder. There's a place where you can find tax professionals, property managers, people to do 1031 exchanges. So as you're starting to look for these folks to build out your team, going to Bigger Pockets first is one of the, you know, probably a good first step.
A
Okay, so once you've got your team built, you've analyzing deals now it's time to actually take action and make the offers. Okay. Now there's a couple things you need to get comfortable with to make your offers. You need to have some kind of trust with your agent if you're doing on market deals. You or you need to have somebody that actually understands a real estate contract, like an attorney that can help you if you are doing off market. Because you'll still need to have a formal contract together. And I do not suggest just finding one online or having ChatGPT create a contract for you to put together so once you have that, you can start making offers on properties and negotiating deals. One thing that I had struggled with for a while was I would be embarrassed to do lowball offers. I would feel like I was offending the person and now I have no problem at all. The worst thing that has happened with making a low ball offer is that they just say no and that's it. And maybe something like, no, that's too low, that's an insult to us. Okay, no big deal. And then I usually follow up. Well, let us know if you change your mind. Sometimes I get, you know, they'll negotiate back with me. I get a counteroffer, sometimes it's accepted. So if you're analyzing deals and it looks like no deals are, are working for you, try lowering the purchase price. That's the easiest thing to manipulate, the easiest number to change. If you change any other numbers, you might make your deal not accurate because you're manipulating the numbers. So decrease your purchase price until the deal works for you and start throwing all out those offers.
B
Yeah, Ash, I could not agree more. I think the biggest mistake that rookie investors make is that they take whatever the listing price is as the lowest acceptable price that a seller is willing to entertain. When in reality they might be overpricing just knowing that they're going to get a lot of lower priced offers. So get the offers out based on where it makes the most sense for you. But just like how on the previous step we talked about analyzing a lot of deals, the same thing is true for getting your offers out. When we were super, super heavy in acquisition mode, I would Send my agent 10 to 15 properties with my listing price attached or with my offer price attached to each one. And majority of the time all 15 would say no. But every once in a while I get one that says yes. And that's how we built our portfolio specifically for the on market deals. So don't, don't worry too much about what your offer price is. Just get it out where it makes the most sense for you.
A
We have to take one more quick break, but we'll be right back after this to talk about what happens when you get a deal under contract.
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This episode is brought to you by Indeed. Stop waiting around for the perfect candidate. Instead, use Indeed's tool sponsored Jobs to find the right people with the right skills fast. It's a simple way to make sure your listing is the first candidate C. According to Indeed data, sponsored jobs have four times more applicants than non sponsored jobs. So go build your dream team today with Indeed. Get a $75 sponsored job credit@ Indeed.com podcast. Terms and conditions apply. Okay, welcome back. So the last part of this process is you got your offer accepted and now you have the property under contract. So you've submitted offers and you get one accepted. Okay, like, yay, this is exciting. Let's pop the champagne. But now the real work begins. You don't get to celebrate right away. You have to do your inspection, which I highly, highly recommend doing in today's market. And as a rookie investor, a couple years ago, it was hard to make an offer and do an inspection and get it accepted because it was so competitive. But that things have changed. I'm doing an inspection on every single offer that I've been putting out, and they're getting accepted with the inspection. So then you're going to have to go through and line up your insurance on the property, start working on the financing details, work with the lender, get your commitment for your loan, things like that. So once you're under contract, there's a lot of things to do. If you do have tenants in place, you want to do an estoppel agreement. This is where you're getting information from, from the tenant. We also have this in the Resource Hub for you on Bigger Pockets. But it's basically a letter you're sending the tenants with the seller's permission, asking for information like, do the. Basically what you're putting on there. Do the lease agreements that the seller is telling you. Is that information the same as what the tenant is saying? Are they verifying that information? Because you don't want to buy a property, Find out. The seller said the tenants are actually paying $1,000 per month. But then this, you know, once you close, the tenant says, no, I pay $500. They, the landlord pays all utilities, things like that. So it's always a great idea. And then just getting your utilities into your name or make sure they're in the tenant's name, if that's how the lease is written, finalize your loan. We do have a closing checklist too, that you guys can check out in the Resource Hub. And if you're going to use property management, start getting that set up, start planning for that day that you close and take over. How are you going to notify the tenants? How are they going to contact you if you're going to manage? If they need to get, if you need to get property management software in place, now is the time to set it up. All of these things you need to do while the property is actually under contract. And if you're doing a rehab, now is the time to get the dumpster set up to get the demo guys ready to, to take that first step right when you close.
B
The only thing I'll add to that, Ashley, is don't be afraid to walk away from the deal during this period either. If things come up during your inspection, during your due diligence. That is the entire reason that a due diligence period in a contract is to give you the ability to either renegotiate or walk away from the deal. So do not get so emotionally attached to the first offer that you've actually gotten accepted that you end up stepping into a deal that doesn't make sense long term. So don't be afraid to walk away if and when it's needed.
A
And once you've closed down the property, it's time to celebrate. But once again, there's still work that needs to be done. Now you have to manage your tenants or manage your property if you're doing a short term rental and make sure you have your operations in place. And now maybe you're furnishing the property. So this is where the fun begins, the real work begins. And you are now a real estate investor. Thank you guys so much for joining us today. I'm Ashley, he's Tony, and we'll see you guys on the next episode of Real Estate. Rookie. At some point, your little real estate side hustle stops. Feeling little rent's coming in. Maybe you've got a couple properties now and suddenly the money part gets real. Your tax bill's going up, you're googling LLC versus S Corp at midnight. And you're just hoping you didn't miss something that'll cost you later. That's where Collective comes in. Collective is the first all in one financial solution. Built exclusively for solopreneurs. Saving you time and money, they help you structure your business for success, whether that's forming a single member LLC or adding an S Corp election. Collective's AI engine, backed by expert oversight, automatically categorizes every expense. You never miss a deduction beyond bookkeeping. They handle quarterly tax estimates and prepare both your business and personal tax returns so you never miss a deadline. You'll also get integrated invoicing plus seamless payroll for S Corp owners, which can unlock thousands in self employment tax savings. And with Collective's community and support. You can finally take the solo out of solopreneur. Right now, Collective is giving you 50% off your first two months when you go to collective.com rookie. That's 50% off your first two months at collective.com rookie.
B
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. So 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
Date: February 18, 2026
This episode of Real Estate Rookie is a comprehensive, actionable blueprint for anyone looking to purchase their first, second, or third rental property within the next 90 days. Targeted directly at new or "rookie" investors, Ashley and Tony walk listeners step-by-step through the process, from clarifying your goals and financial foundation to making offers, closing, and finally managing your new investment.
They pull from Ashley's book, "Real Estate Rookie: 90 Days to Your First Investment," but deliver the roadmap in an approachable, week-by-week checklist with lots of personal experiences and practical tips.
(Starts ~00:36)
Clarify Your Why:
Ashley emphasizes that before analyzing or finding deals, you must get clear about why you want to invest in real estate.
"You need to set your foundation and you need to understand why you're investing in real estate. What is your goal? What do you want out of it?" – Ashley (00:47)
Personal Finance Prep:
Know your capital sources and have a solid grip on your finances. Utilize budgeting tools (Ashley recommends Monarch Money) for a full financial picture.
Rank Your Priorities:
Tony explains the core motivations in real estate—tax benefits, cash flow, and appreciation—and recommends ranking what matters most to you, since few deals maximize all three.
"It's important as you're getting started to understand what is it that I'm trying to optimize for..." – Tony (02:13)
Action Item:
Block out 2–3 hours to write out your goals, motivations, and plan, either on paper or digital doc. This visioning step is foundational.
(Starts ~04:06)
Asset Class & Strategy:
Decide what type of property (single family, small multifamily, condos, mobile/manufactured, etc.) and strategy (flipping, long-term rental, short-term rental) fit you best.
"Identifying what type of property you want to buy, and then what's your strategy that you're going to layer on top of that specific niche." – Tony (04:06)
Buy Box Creation:
Use the "buy box" resource from BiggerPockets to define specifics (property type, price, location, etc.) for your ideal purchase—this narrows focus during deal analysis.
(Starts ~05:40)
Avoid "Goldilocks Syndrome":
Don’t get caught searching for the "perfect" city; there are hundreds of viable markets. Start with a few that align with your goals.
"There are 20,000 plus different cities... chances are there's not just one city that's the best... There are hundreds, if not thousands..." – Tony (05:40)
Use Data:
Access tools like the BiggerPockets "Find a Market," Neighborhood Watch, Bright Investor, and even ChatGPT for data (job growth, rents, taxes, landlord/tenant laws).
Validate With Your Strategy:
What works for one investor or strategy might not work for another; don’t blindly copy social media trends—verify based on your own plan.
"Just because you're going to go, it works for somebody else in a market doesn't mean that it's going to work for you." – Ashley (07:36)
Memorable Moment:
Lighthearted banter about luxury short-term rentals next to manure-laden farms adds warmth and humor to the conversation.
"Do you want fresh manure or liquid manure? There's two different." – Ashley (08:50)
(Starts ~09:17 and 14:52)
Analyze Listings Early:
By week 4, start analyzing 5–10 active listings per week in each chosen market. Even if a property isn’t a real candidate, practice builds skills.
Track & Spot Patterns:
Use calculators and spreadsheets to document deal outcomes and spot what works or doesn't in your market.
Challenge: "30 Deals in 30 Days":
Tony issues a challenge—analyze one deal per day for a month to accelerate learning and increase chances of finding a winner.
"I like the idea of 30 deals in 30 days... Most people do not find deals simply because they're not analyzing or underwriting enough." – Tony (14:52)
Watch for Overlooked Expenses:
Consider market-specific costs (e.g., snow plowing, pools) and check with local investors for non-obvious but critical expenses.
"That's where it pays to go into BiggerPockets forums, Facebook groups, to ask in the market that you're investing in, what are some other expenses that I'm not aware of?" – Ashley (16:33)
(Starts ~20:19)
Key Team Members:
Lender/private money source, real estate/wholesale agent, attorney (especially in attorney-close states), title company, insurance agent, handymen, property managers.
How to Find Them:
Start Early:
It’s not too soon to contact potential team members—let them know your intentions and begin building relationships before you have a deal.
"Just call them, let them know what you're trying to do and that you're looking for a handyman to take care of a property once you get in under contract and see if that's even something they'd be interested in." – Ashley (21:50)
(Starts ~23:15)
Get Comfortable Making Offers:
Don’t fear low offers—it's part of the business.
"The worst thing that has happened with making a low ball offer is that they just say no and that's it." – Ashley (23:36)
Don’t Fixate on List Price:
Sellers often list high expecting negotiation.
"The biggest mistake that rookie investors make is that they take whatever the listing price is as the lowest acceptable price..." – Tony (25:00)
Action Item:
If numbers don’t work, lower your offer. Submit lots of offers—volume increases your odds.
"When we were super, super heavy in acquisition mode, I would send my agent 10 to 15 properties with my offer price attached... majority would say no, but every once in a while I get one that says yes." – Tony (25:00)
(Starts ~28:00)
Inspection & Financing:
Always do an inspection. Work out insurance and finalize your loan with the lender.
Tenant Estoppel Agreements:
Essential if tenants are in place—verify what the seller says with the tenants directly.
"You don't want to buy a property, find out the seller said the tenants are actually paying $1,000 per month, but then...no, I pay $500." – Ashley (29:35)
Utility Transfers:
Arrange for utilities as per lease (your name or tenant's).
Prepare for Ownership:
Plan for property management, set up software, arrange renovations or hand-off to a manager. Use the closing checklist available from BiggerPockets.
Be Ready to Walk Away:
The inspection/due diligence period exists so you can renegotiate or exit if things aren’t as advertised.
"Don’t be afraid to walk away from the deal during this period...do not get so emotionally attached to the first offer that you've actually gotten accepted that you end up stepping into a deal that doesn't make sense long term." – Tony (30:46)
(Starts ~31:10)
| Segment | Timestamp | |--------------------------------|-------------| | Laying Your Foundation | 00:36–05:05 | | Choosing Market | 05:40–09:17 | | Practicing Deal Analysis | 09:17–14:52 / 14:52–20:19 | | Building Your Team | 20:19–23:15 | | Making Offers & Negotiation | 23:15–25:52 | | Under Contract, Due Diligence | 28:00–30:46 | | Post-Close Operations | 31:10–end |
The hosts are pragmatic but warm and encouraging—never condescending, always rooting for rookies to succeed, and unafraid to make real-world jokes or share their own struggles. There’s a focus on demystifying the process, giving listeners explicit action steps, and providing emotional support for the moments when progress stalls.
For a more detailed roadmap or to find resources/tools mentioned, visit the BiggerPockets Resource Hub.
Hosts: Ashley Kehr & Tony J. Robinson
Podcast: Real Estate Rookie
Episode Title: How to Buy Your First (or Next) Rental Property in 2026 (Step by Step)
Release Date: February 18, 2026