The podcast episode tackles three rookie investor questions from the BiggerPockets forums. First, a 23-year-old asks the best way to learn real estate—whether to invest in courses or rely on free content. The hosts advise building a strong foundation through books, podcasts, and forums, but note that coaching can accelerate growth if you have the capital and know your learning style. They recommend asking how much time and mistakes you're willing to accept, and ensuring you don't blow savings on education that could fund a deal. Second, a new investor in Minneapolis seeks deal leads. The hosts suggest joining local Facebook groups, attending meetups, and connecting with wholesalers and other investors who may share off-market opportunities. They also challenge the idea that no deals exist on the MLS, urging listeners to ignore list prices, analyze numbers, and target properties with long days on market or price drops, especially in current buyer's markets. Third, a newlywed couple with free tiny house housing weighs options: adding to the tiny house (ruled out as a sunk cost), buying a small single-family home, an out-of-state short-term rental, or house hacking a duplex. The hosts eliminate the tiny house addition and the out-of-state rental, as neither solves their space needs. They lean toward house hacking, encouraging the couple to explore all rental income strategies—long-term, by-room, or short-term—to make a duplex affordable, while using market leverage to negotiate better purchase prices.
You're ready to start investing, but now you're staring at the three questions every rookie hits first. How do I actually learn this? Where do I find a real deal? And if I finally have some money saved, what should I do with it? Today's questions come straight from the bigger pockets forums, and they're still all about getting out of the research phase without rushing into a bad firstly. This is The Real State Rookie Podcast. I'm Ashley Kier. And I'm Tony J. Robinson with that. Let's get into our first question. So question number one today comes from OME in the bigger pockets forums. And OME says, I'm 23 and I'm looking to build a buy and hold the rent app portfolio in the Midwest with markets like St. Louis, where I'm based Kansas City, Indianapolis, Cleveland, and Columbus on my radar. I've started doing my homework. I've read quite a bit, listened to podcasts, and started talking with investors and professionals, but I keep landing on the same question. What's actually the best way to learn this? Well, instead of piecing it together from a bunch of different threads, for those who started from zero, is you pay for a course or coaching or go the free content plus trial and error route. If you paid, what was it for and was it actually worth it? If you didn't, which books, podcasts, YouTube channels, and forums actually move the needle for you bonus question, if you were 23 and starting today, knowing what you know now, what's the first move that you would make? Not fishing for a shortcut. I know experience is the best teacher. I just want to invest my time in money wisely, whether that's yourself study, mentorship, or quality course alone. I don't just want to blow three to five K on a course that BP could have replaced or spend six months reading and missing something a good course would have flagged. On day one. It's a great question. And probably one of the more heated debates in the bigger pockets forums. And, you know, I'll give my take first guys is that I think like anything in life. There's probably pros and cons to paying for assistance. And different people need different resources. Now, what I will say is that regardless of whether or not you choose to go join a course, get a mentor, whatever it may be, you still need that strong foundational knowledge. Like you still need to be listening to the real estate rookie podcast. You still need to be reading books, watching the YouTube videos and laying a strong foundation. Like I don't think anything replaces that. But once you have that foundation laid and you're thinking about actually taking that next step. I think there's a couple of questions to ask yourself to say. Just paying for guidance actually makes sense. The first question that I'd ask yourself is how much time are you willing to invest and how many mistakes are you willing to make to get it right on your own. Because as much as you watch YouTube videos as much as you can read books, it's still difficult to times to take that information and distill it in a way that makes sense for your unique situation. And there's no feedback loop there from the author to say, hey, Ashley and Tony, if you get stuck here, here's what I would actually do. You have to infer what the right next step would be based on the knowledge that you've gained. So that's the first reason how much time are you willing to spend and how many mistakes are you willing to make. And then I think the second piece is the capital, right? Like if you are very capital constrained, I would never want someone spending their only $5,000 in the course and then rebuilding their capital trend and get the deal done. Like you've got to make sure the capital is here to cover that and still have enough leftover to go buy the actual deal. For me, I didn't start with a chorus or coaching. I was pretty much solo and then that was in 2013 and then 2017. I found bigger pockets went into the forums was just consuming information and I was able to triple my portfolio in that year just from reading and learning from what other investors were posting. I don't even think I like posted that much myself, but just reading through the forums. So that was such a big help for me. And I think you need to before you even decide if you should do a course or if you shouldn't, you need to ask yourself a couple questions. Not even regarding real estate or courses, but how do you learn? Think about back when you were in school or maybe you're still in school. Was it a torture to sit through a class and listen to the teacher talk? Do you love to read? Is it easy for you to read to to scroll and read the, you know, news on your phone, sit with a book. Are you more engaged when it's a bunch of people, such as doing a Zoom call where there's a lot of other people in the call and they're asking questions and you're engaged into the chat. What is the best way that you learn for me. I went to a seminar about a month ago. It was a horrendous for me because I was taken back to my college day is sitting in a class from we were there from 8 am to 6 pm. Those two days I was there and I could not sit still. I could not focus. I dreaded it. I realized once again, it was a great reminder. I do not learn that well. So I can't attend courses and things like that. We're here in a classroom setting and you're sitting just listening to someone talk and talk and talk and talk. If it was a workshop setting where it's hands on, I can learn that way. I know that it's engaging. You're actively doing something that I can handle. Zoom calls. I can also handle Zoom calls. If it's not a webinar format. I can't sit there and I can't watch a webinar. If it's engaging where there's people coming on to the call to ask questions, if there's a chat going and you know you're being engaged into the call that I can do. Self-paced stuff. I cannot do. I used to try to take the real sit exam to get my real estate license. I started the online course probably about four times. I paid the 99 feet to restart the course and I just couldn't do it. I wouldn't make the time for it wasn't priority. So I can also do self-paced courses. So really think about yourself and how you actually learn. And also, you know, who the instructor is what the topic is, things like that. And if that will actually benefit you. But I think taking that first step to is how do you learn and maybe scrolling forums and things like that is actually going to be more beneficial than paying for a course that self-paced where you're supposed to watch the videos. I think the last thing I'd add is that some of the biggest jumps in my life both personally and professionally came and I hired like an actual coach. Like I got in the best shape of my life when I hired a fitness coach to tell me what to eat and when to work out and when to sleep and when to do all those things. Even as a business owner, like entrepreneurial, not even just real estate, but as an entrepreneur. I think my biggest leaves came and I invested into the right coaching. So I'm going to sit down and look at my specific situations. I hear here's what you should do next. And as I look at the people who are far more successful than I am, they spend even more money on coaching and people telling them what to do than I do. So I think my aspiration to spend even more of my money on a coach who's done what I've done telling me exactly what it is that I need to do because I've seen that be the path for success. I think that the person got to make sure that the pedigree is there, but generally speaking, the folks who have found more success than I have have also invested more themselves and I have as well. And go into it with a plan of what you want to get out of it. So what do you want to get out of whatever course or coaching that you're doing and make sure that's what you're actually going to get out of the course that you sign up for. Coming up learning is great, but how do you actually find your first property when Zillow feels picked over and every good deal seems to go to someone else first. That's next. All right, so we've talked about how to learn without getting stuck. Now let's talk about where deals actually come from. Our second question comes from Samuel and Minneapolis. Hey, all I'm a new investor looking for leads on potential flips or burr properties. I've joined a few Facebook groups and I'm on Zillow a little too often, but in my experience, the best opportunities often come from the right connections. So here's my ask where have you found opportunities to invest. Can you recommend anyone I should connect with. Yeah, first let me answer for you, Ashley, because you would say in line at the grocery store at the mailbox, checking the mail at my kids football games. Those are the places that Ashley goes to find all of all of her best deals. I always say I'm not going to buy anything. And then like the perfect deal just comes to me, which is not a strategy to actually find deals. Those are just bonus opportunities that come up. But that happens from not working and talking about what you're doing and not talking about going to meetups or there's other investors, but also like your friends and family and people you're around letting them know what you do, what you're looking for and things like that. And deals will come to you over time. Maybe it's a bit of manifesting. I don't know. I'm not a big manifester, but I guess I'm not manifest and hard enough. I think for me, and it's a great question, right? And look, guys, like good deals are, we call them good deals because like they're not abundant, right? Like you've really got to do some some like work to get there. But if I'm a new investor starting out, I think what you laid out here, Samuel is a great starting point going into local Facebook groups posting what your buy boxes like who it is, you know, like what areas you're focused on price points, things like that. And you just, you know, go in there once a week and repost that same message across all the Facebook groups. And you'll just by default. Whole sellers are in those groups just like scraping looking for people that they can go, they can go message. I think that's an easy way.
I think getting active in your local real estate meetup scene, super helpful as well. A lot of times you can connect with the big wholesalers and maybe the newer guys on the scene who are still hunting for their first deal and they're hungry for a buyer, right? They're asking the same question, but how do I find buyers for these deals that I'm finding as a wholesaler? So I think getting into the room, getting into the physical space with other investors will be big. And then if you can meet maybe other flippers or, you know, burr type investors in your market, they also don't have unlimited capital. So sometimes maybe a deal comes across their desk or like, doesn't quite fit my buy box or, you know, I'm maxed out right now. Hey, let me pass this off to Tony Nash and see if they want it, right? Or maybe they're open to sharing with their wholesalers, right? So I think building your connections both digitally in the Facebook groups, great places start, but also kind of pound in the pavement in real life and trying to meet people in shakans. We have a good way to get started as well. I'm also very anti. There's no deals on MLS because I've found lots of deals on MLS and I'm going to challenge you to like why are you saying there's no deals on MLS? Is it because there's like physically no properties listed for sale that fit your criteria? Or is it because the asking price when you analyze the numbers doesn't work, it's a negative cash flow because you don't actually know if it's a good deal or not until you make an offer to see if your offer is accepted. So a, remember, a property, what it's listed for, doesn't mean that's what it's going to sell for. You can actually buy a property for less the money. So you don't actually know if it's a good deal or not, you know, unless maybe there is maintenance rehab, things like that, doesn't fit your criteria that needs to be done. But as far as if you're saying that because it's listed at a higher price point than you think it's worth, then you need to run the numbers, go to the bigger pockets calculator reports and play around and change the purchase price until the numbers do make sense. So that means you have to you know, offer $20,000 last $50,000 last like in a lot of markets right now across the country, we are in a buyer's market. One thing that I really like to do is I go in Zelo and I like to sort the properties by newest. So the ones that have just recently hit the market. So by days on market, and then I go to the very last page and I look at what has been sitting for a long time. And usually those are more motivated sellers than somebody that just hit the market. I go and I look at the pricing. So okay, how long has it been on the market since they listed it? Have they done any price drops? How many have they done? Something I'm seeing happen a lot in two vacation towns that I keep my eyes. One is the ski resort town, one's lake house town. Is I am seeing them list the property and then de-list it over the winter and then listed again. Some of these properties have been listed. This is their third summer being listed. And you want to know that because the days on market only shows the most recent listing. You have to actually go back and look at the history of the property that's available on Zillow. But I think that's a great starting point for actually looking at the properties on Zillow to find some deals. I couldn't agree more. I just want to highlight that is that right now, at least as of this recording, we're talking like summer 2026. Right now is a great time to ignore the purchase price. Like whatever the list price is on any property you see on the MLS completely ignore it and go in with whatever numbers make the most sense for you. Like sellers are having a little bit of a hard time right now. And I know that because I'm selling a property right now, a flip that we've been sitting on for way too long. So sellers are not having the best time right now, but you can use that as leverage. And if somebody came to me with a really kind of insulting offer, I would at least consider it today because it's like I've been sitting on this property for too long and I'm sure there's a lot of sellers who feel that who feel that same way. Right. So don't worry about what the list price is. Focus on where does number make sense for you and then just offer even below that number. All right, guys, we're going to take a quick break. But when we're back, a listener has what a lot of rookies want free housing and money save. The question is whether to buy now, keep saving house hack or trying out a state rental. We'll walk through it right after this. All right, guys, welcome back. Our last question comes from Derek and this one has a minute bit of a crossroads in a bit of a sticky situation. But here's what Derek says about what's going on in his life. So he says, my wife and I just got married and have an interesting situation in regards to real estate. We currently live in a tiny house for free as part of compensation for my job while we are extremely grateful for the free housing is starting to become too small and we're hoping to upgrade toward a bigger space in the near future, especially as we were hoping to have children within the next two to three years. For context, we can comfortably put down 30K on a property and qualify for state assistance of an additional 15K down payment. And we make about 95K annually combined. So we have a few options. Option number one is that we build an additional tiny house and join them together at our own expense. This would be relatively inexpensive about 15K. But it would be a sunk cost. It would let us continue to enjoy free housing for the next few years and save more for a down payment. But would be extremely challenging to have kids in. Number two, buy a small single family in our area. We live in Rhode Island and the housing market is essentially out of our price range everywhere except for those areas where we do not desire to live. So we could buy a small single family living it for a few years with the hope to sell the refining something bigger while keeping it to rent as a long term rental. At least we will be gaining equity with this option though. I worry we do not have enough saved for this to make sense given how expensive our market is. Option three, buy an out of state short term rental. This is the most interesting idea to me as out of state properties are more affordable and the upside is much stronger. We've been looking at upstate New York. However, this option means we are stuck in the tiny home we live in until we have enough equity to either borrow against the SDR or sell it. And then option four is house hacking a duplex. This I would love to do however, I've been unable to find any duplexes that we can afford in our area though I do look daily. All right. So just just a recap because this is a great question. So they've got free housing right now but the place is really really small. They're thinking about either put in 15k to add on to their existing footprint but they wouldn't own that at all. Like once they don't have the job that they lose that they buy a single family in their current area and a place they don't want to live in right like it's not the best area. They buy an out of state short term rental where they house hack something maybe in their their local area as well. Those are all good options. Or I guess each option kind of has like its own merit. One of them I'd rule out immediately. I'm curious if you say the same thing Ash but like the 15k to add on to the tiny house that isn't theirs. I wouldn't do that. I feel like that's not a good use of their funds to dump it into an asset that they don't actually control. What's your take on that first one? 100% agree. Like you're not going to get that money back. You're not going to get any tax advantage to doing that. I would say no because also what is the guarantee that you actually can live there for a few more years? Like your job could go away. They could not renew your lease on the property. I'm not sure how it set up with work but jobs come and go. There's no such thing really as job security in a lot of cases. So I would agree with you on that Tony. So of the other options we have left, buying a small single family in their area but in a part of town that don't want to live in, buying an out-of-state short-term rental that's more affordable or house hacking. I think I questioned the house hack because if they can't afford a small single family would they be able to afford a small multi-family area. So I wonder if they kind of fall into the same sticky situation but between those three options which one are you leaning more so toward? Well I'm actually going to eliminate the out-of-state short-term rental and I'm going to do that because this doesn't solve their problem. They want more space. So even if they want to bought the short-term rental I feel like they're still not going to be you know trying to achieve what they actually want is to get a bigger house but not have to pay full price for it I guess. I'm actually going to lean towards house hacking and duplex and when they say they can't afford that I'm curious as to how much has gone into actually looking at how much rent they would receive for the other side of the property and by doing different strategies. So did they compare with you know what long-term rent would be, what renting by the room would be for that other unit, what a short-term rental would take in in that other unit. So I'm going to say house hacking and duplex and also you know why can't they afford it in their area have they looked at all of the options of renting out that other unit. I'm going to throw a curveball and give them an option that they didn't even list here. I think the fact that they're three years away from like really really needing the space I try and stretch out a little bit longer because it's free housing like they're living for free which oftentimes is going to be your biggest expense and with the 30k that you've got saved up. I wonder if instead you could take that maybe go go flip some houses either locally in your area or maybe even try and do it remotely somewhere else where your budget will stretch and you
use that 30K as a foundation to get a bigger chunk of cash back on one or two house flips. And now with the money you're saving from the rent, in addition to the money that you're making from the flips, can you maybe now, in the next 24 months, gotten by a bigger property that kind of checks all those boxes in the actual part of town that you want? So I think let's leverage the free housing, but let's go deploy that capital in a way that's going to multiply two or three X for the next couple of years. If you're in that beginner stage, today's episode should be permission to slow down in the right places and speed up in the right places. Don't rush into the wrong deal, but also don't spend the next year only learning either. You have to take some action. This has been an episode of Real Estate Rookie. I'm Ashley, he's Tony and we'll see you guys on the next episode.
Podcast Summary
Key Points:
The first question addresses learning real estate
The second question focuses on finding deals, suggesting local Facebook groups, real estate meetups, networking with wholesalers, and analyzing MLS listings beyond list prices, especially in buyer's markets.
The third question involves a couple with free tiny house housing weighing options: adding to it (ruled out as sunk cost), buying a single-family home, buying an out-of-state short-term rental, or house hacking a duplex.
The hosts recommend eliminating the tiny house addition and the out-of-state rental, leaning toward house hacking as the best fit for their space and financial goals.
They stress evaluating rental income potential (long-term, by-room, or short-term) to make a duplex affordable, and using market conditions to negotiate lower offers.
Summary:
The podcast episode tackles three rookie investor questions from the BiggerPockets forums. First, a 23-year-old asks the best way to learn real estate—whether to invest in courses or rely on free content. The hosts advise building a strong foundation through books, podcasts, and forums, but note that coaching can accelerate growth if you have the capital and know your learning style.
They recommend asking how much time and mistakes you're willing to accept, and ensuring you don't blow savings on education that could fund a deal. Second, a new investor in Minneapolis seeks deal leads. The hosts suggest joining local Facebook groups, attending meetups, and connecting with wholesalers and other investors who may share off-market opportunities.
They also challenge the idea that no deals exist on the MLS, urging listeners to ignore list prices, analyze numbers, and target properties with long days on market or price drops, especially in current buyer's markets. Third, a newlywed couple with free tiny house housing weighs options: adding to the tiny house (ruled out as a sunk cost), buying a small single-family home, an out-of-state short-term rental, or house hacking a duplex. The hosts eliminate the tiny house addition and the out-of-state rental, as neither solves their space needs.
They lean toward house hacking, encouraging the couple to explore all rental income strategies—long-term, by-room, or short-term—to make a duplex affordable, while using market leverage to negotiate better purchase prices.
FAQs
Start with free resources like podcasts, books, and forums to build a strong foundation. Then, consider paid courses or coaching if you need structured guidance, but first assess your learning style and capital to ensure you don't spend money you need for deals.
It depends on your learning style, time, and capital. Free content works if you're disciplined, but paid coaching can accelerate progress if you need feedback and accountability. Ensure you have enough money left to actually invest after any course purchase.
Join local Facebook groups, attend real estate meetups, and network with wholesalers and other investors. Also, don't ignore the MLS—analyze properties by running numbers, and look for motivated sellers by checking days on market and price history on sites like Zillow.
There are deals on the MLS, but you need to ignore list prices and offer based on your own numbers. Look for properties that have been listed for a long time or have had price drops, as these sellers may be more motivated to negotiate.
House hacking a duplex is often better if you need more space, as it solves your housing needs while building equity. Out-of-state rentals don't help your immediate space problem and add management complexity, so prioritize local options first.
No, avoid spending on improvements to a property you don't own, like adding to a tiny house for free housing. You won't recoup that cost, and you could lose access to the property if your job situation changes.
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