Pod Insights BiggerPockets Real Estate Podcast If I Had to Start Over in Real Estate in 2026, I’d Do This Now About this episode If we had to start our real estate portfolios over again in 2026, this is exactly what we’d do. If you’re just beginning to buy rentals or want to overhaul your current portfolio, this is the episode to listen to. Tim Yu went from zero rental properties to a dozen in just four years, but looking back, he would have done things very differently. He could have made more passive income, stressed less, worked smarter, and saved himself from a ton of headaches. Now, he’s sharing with you what to do instead, so you don’t make the same mistakes. Fast forward to today: Tim is now buying properties that cash flow $3,000-$5,000 per month thanks to the lessons he learned. Why does Tim regret scaling fast with single-family? Why do most people quit their jobs too soon after their first taste of real estate success? And why is Tim only trying to buy one solid investment property per year? His answers go against most real estate advice, but following his lead could accelerate your path to financial freedom. In This Episode We Cover The easiest first rental property new investors should try before scaling How to “test” new strategies so you don’t lose money (like Tim did) Why Tim kept his job even while making serious money in real estate The real estate analysis mistake Tim made that cost him time, sleep, and money Why you only need to buy one solid investment property per year (scale slower, make more!) And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1251 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email [email protected] . Learn more about your ad choices. Visit megaphone.fm/adchoices
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Dave Meyer? If we had to start over in real estate investing in 2026, here's how we would do it. No rentals, no giant piles of cash, only the knowledge we've gained from years of investing success and a couple of failures along the way. These are the properties we buy right now and the blueprint you can follow too.
0:23 Dave Meyer? Hey, everyone. I'm Dave Meyer, Chief Investment Officer at BiggerPockets. Henry, what's up, man?
0:28 Henry Washington? What's up, Dave? I am excited to talk about this because I think more people need to think through how to invest, starting from scratch, based on a lot of the experiences that we have. Because I tell you, I've learned a lot.
0:43 Dave Meyer? Yeah, learn from our mistakes and successes. They're not all mistakes, but man, I didn't start by listening to a podcast or reading a book. I just jumped right in and the amount of dumb stuff I did that I could have avoided had I just listened to experienced investors. Man, I don't want to tally up what I've lost in terms of money, but just trust me, you'll be better off just listening to a couple of lessons from grizzled old investors.
1:10 Henry Washington? Amen, brother.
1:11 Dave Meyer? Today, you don't have just me and Henry. We have a great guest joining us today. It's investor Tim Yu. Tim has been on the show before. You can hear his full investor story in episode 1090 from March 2025. And not to spoil it, but if you listen to that show, you'll hear that in only five years in real estate, Tim has built up a sizable portfolio. He's tried almost everything in just the last couple of years, flipping, wholesaling, rental properties. So we thought it'd be a good person to toss around today's topic because Henry and I can talk about our original days, but that was a totally different era. So now we have people who started in three different eras of real estate investing, bringing you advice about how to start or scale.
1:52 Dave Meyer? This isn't just your first deal, how to like build a portfolio from scratch. Hopefully this is going to help you see the path that worked for us and avoid some mistakes we made along the way. Henry, you ready?
2:04 Henry Washington? Yeah, heavy on the avoiding mistakes part.
2:08 Dave Meyer? All right, you can see where this conversation is heading, but let's bring on Tim and get right into it. Tim, welcome back to the BiggerPockets Podcast. Thanks for being here.
2:17 Speaker 02 Hey, man. It's always good to see you guys. So I appreciate the invite.
2:21 Dave Meyer? Yeah, we did a great show with Tim about a year ago. It's episode 1090, if you want to go check it out. But Tim, for those people who haven't listened to it yet, maybe give us a brief background of who you are and your real estate journey so far.
2:33 Speaker 02 Yeah, so I started investing in 2022. That's when I bought my first property ever. I started doing this, working full-time in the military, active-duty military. And over the last four years, we've done different strategies, wholesaling, flipping, buy-and-hold rental portfolios, and then moving into the commercial space nowadays. And I'm actually in the transition of getting out of the military now. So it's been a crazy four or five years, man.
2:59 Dave Meyer? Congrats, man. And the plans to go into real estate, I assume, now that you're transitioning out of the military?
3:04 Speaker 02 Yeah, I got the taste of it during the last four years, so it's pretty exciting to go full send now, you know?
3:10 Dave Meyer? That's awesome. So maybe just fill us in, Tim. What does your portfolio look like today?
3:14 Speaker 02 Yeah, so when we first talked, we had 12 properties, single families in the portfolio. But we actually sold quite a bit of them. So we sold six of them in the last year or so. Not because of the market or whatever the case may be, but you know, as time progressed, I started to realize that I didn't really like the single-family model.
3:35 Dave Meyer? Okay.
3:35 Speaker 02 And it was a lot of headaches for me personally, just dealing with all the single families across the country. So we focused on more commercial-based assets and then more active income. So we still do the wholesaling and the flipping side of the house. And then we want to shovel the money into commercial assets, which is a little bit better fit for us. So after selling those properties, we have six properties in Kentucky right now. And then we still have those Iowa deals going on. So we have six houses out there. So we're trying to sell those off as well. So we're just free of all the Midwest stuff going on.
4:06 Dave Meyer? Oh, interesting. Okay, so you've done 12 single-family homes, you've done wholesaling, you've done flipping. Now you're moving into commercial. So you've done a little bit of everything at this point?
4:15 Speaker 02 Yeah, I love trying things at least one time. The flipping side of the house is difficult on its own too, especially with like the market changing all the time. But for me, Me personally, buying the single families that I was buying and only making like three, four hundred dollars a month on them each. It's not really a sustainable model for me to like quit my job. And that's kind of how we ended up here today was like, okay, if I can sell these properties off, buy one or two commercial deals that that make pretty good money and can appreciate quickly. And then still have that active income to supplement that W two. I would feel comfortable like leaving. So it's kind of how we've shifted like the mindset over the last like year or two, shrinking that footprint of properties that we have so we can focus on like one or two good assets.
4:58 Henry Washington? The single family rental space, you're right that the cash flow is typically for, you know, between a hundred and five hundred dollars a door in a single family space. And that's not life changing money. What you learn as an investor is it's the equity, the debt pay down and the appreciation that truly help you build wealth. And so typically, most single family investors learn that they have to produce some other kind of income in order to replace their job income, or else you gotta get a whole lot of one to three hundred dollar rental property doors in order to replace that actual income. So was the goal from the beginning to always build up a portfolio big enough for you to leave your job? Or was it just to supplement retirement?
5:42 Speaker 02 When I first started, I knew that it was a long term plan with real estate. Like I knew that it wasn't like a get rich quick type of thing. My goal was to buy five houses and retire off my pension like in the military. And, you know, thirty years pay off the rest. And that plan is awesome. And I think that it's a really, really awesome strategy for people that are slowly accumulating wealth and there's nothing wrong with that. For me, I just knew that once I started buying properties and getting into investing that I really want to do this full time, just because. You know, being your own boss and, you know, running your own business is awesome and it's super rewarding in its own way. So I guess it really depends on the goals of the individual
6:24 Speaker 02 person. But for me, yes, I always wanted to use this vehicle to quit my job.
6:28 Henry Washington? Yeah, I totally get that. I think it doesn't matter what your strategy is. You have to figure out a strategy that's going to produce the cash that you need to produce in order to make some sort of job change or job shift. Yes, I retired, air quotes, from my corporate job, but I flip houses now to create income, which in itself is another job, right? And it sounds like what you're doing is instead of flipping houses or some other real estate strategy that requires active income, you're looking at more commercial because you can get higher cash flow returns in commercial and then that allows you to be able to live off of your rental portfolio. But at the end of the day, the goal has to be like, how do you create
7:12 Henry Washington? income from your real estate business? And then you can use that income to offset your lifestyle.
7:17 Speaker 02 Yep, spot on. Buying one commercial asset will make you X amount of money per month and having one or two of those can actually replace your income relatively quickly. And for me, having all those single families, you know, I was still doing all that craziness, managing those properties and then still showing up to my job every day. And I was like, this is just not worth it for me personally. So that's why we made the shift in like, late 2024 of like selling off those properties. Yeah, spot on, man.
7:46 Henry Washington? For your commercial assets, are you planning to manage those on your own? Or are you having professional property management? Because I have owned a commercial asset before. I've owned Bertha Commercial Strip Center and a mobile home park and both of them are still management intensive. I would almost argue that my commercial asset is more management intensive just because of the types of tenants and the types of things you get to do with the leases. And yes, they can be more lucrative, but it's not necessarily any more hands off than managing a single family rental property.
8:23 Speaker 02 No, that's a really good point, man. So, so we thought. What about that too? Um, number one would be, we would rather GP and manage that bigger asset um, because of the return, but also number two, the, the asset class that we're looking for is more of strip malls.
8:38 Dave Meyer? Oh, interesting.
8:39 Speaker 02 Yeah. So my business partner right now, he actually owns three strip malls throughout Virginia. His asset classes are relatively passive in terms of what type of tenants they are.
8:49 Dave Meyer? A triple net?
8:50 Speaker 02 Yeah. So he has tons of triple nets. He's got the US post office in one of his units.
8:54 Dave Meyer? Oh, that's a dream.
8:55 Speaker 02 And they have like, they have a 30 year lease. So, you know, it just really depends on, you know, what type of tenants you do put into those strip malls. But for us, like, we're okay with managing those type of assets because we're only dealing with a small few versus just dozens of different tenants across the country.
9:11 Henry Washington? Well, just like regular real estate, our job as landlords is to be very good at tenant selection. And that doesn't change with commercial real estate. You're just looking at the tenants a little different. But one of the saving graces as well is the leases tend to be a whole lot longer when you find these good tenants. So you can underwrite people into your building in 10, 15 year leases, which is a whole lot different than just a one year lease in a residential space.
9:35 Dave Meyer? But the turnover costs are big.
9:37 Henry Washington? Turnover costs are very expensive.
9:39 Dave Meyer? Yeah, that's the problem when you bet wrong.
9:41 Henry Washington? Yes.
9:41 Dave Meyer? There's pros and cons for sure.
9:43 Henry Washington? It's interesting. I like hearing different perspectives and different people's approaches to real estate. It's one of the reasons why I love real estate as an asset class is because you really do get to choose your own adventure based on the life that you're trying to create for yourself. It sounds like a lot of the things you're experiencing in your life are pushing you towards a certain investment strategy. If you don't like a certain aspect of an investment strategy, you can choose something different that allows you to create the kind of life that you're looking for. So I'd love to get more into learning about what you would do if you had to start over today, since you've done so many different strategies. And we will learn what you would do when we come back from the break.
10:22 Dave Meyer? Most investors only think about insurance when something goes wrong. A tenant injury, storm damage, loss of rent. Then suddenly, the cheapest policy doesn't feel like the best one anymore. That's why a lot of BiggerPockets investors use steadily for landlord insurance, designed specifically for rental properties. Whether you own one property or a growing portfolio, they make it simple to get covered properly. And BiggerPockets Pro members get an extra 5% off their landlord insurance premiums. Visit biggerpockets.com/landlordinsurance to get a quote today.
10:56 Henry Washington? Here's a strategy that most W2 employees have never heard of. Normally, if you want to write off a rental property against your regular income, you need real estate professional status. That means tracking hundreds of hours a year. Rent2Retirement just launched a program that skips all of that. It's called the STR loophole tenant placement program. Here's how it works. You buy one of Rent2Retirement's Class A new construction investment properties. You set up an Airbnb listing and self-manage it for the remainder of the year. Rent2Retirement then rents the home as a short-term rental to establish it as an STR for the year. No furnishing required, making this the easy button to save five or six figures in taxes this year.
11:38 Henry Washington? And because you're the sole manager, there's no hourly minimum to meet. That lets you use a cost segregation study to accelerate the depreciation and potentially write off over $100,000 against your income, even on your first rental. Add in cash back up to 13% of the home price, which exceeds $60,000 on some properties. With this massive cash back incentive, investors are seeing total returns up to 126%. New construction, A-class properties, and inventory is limited. Learn more at biggerpockets.com/retirement or text REI to 33777. Again, text REI to 33777.
12:20 Dave Meyer? I just booked a backpacking trip through Olympic National Park. Two nights out on the trail, no cell service, nothing to do but eat trail mix and stare at mountains I'll never get tired of. That's the whole appeal. But while I'm off grid, my place doesn't need to sit empty. I can list my space on Airbnb and make a little extra income while I'm away. And with Airbnb's co-host network, I could partner with a vetted local co-host to help take care of the details, from guest communications to onsite support, so I can fully unplug and enjoy my time out in the backcountry. If you've got upcoming travel plans, you can find a co-host at Airbnb.com/host.
13:02 Speaker 03 At Edward Jones, we believe rich is more than caring about the latest and greatest. It's also taking care of what gives your life meaning. That's why your dedicated financial advisor meets you where you are with personalized financial strategies that help protect what matters, so you can preserve your progress while creating a path forward. The key to being rich is knowing what counts. Let's find your rich together. Edward Jones. Member SIPC.
13:35 Henry Washington? All right, we're back on the BiggerPockets Podcast with Tim Yu, and we're learning about what he would do if he had to start over in real estate. Tim, you've done a lot of different things when it comes to real estate investing. So if you had to start completely over, would you pick the same strategy as when you started out? Or would you pick maybe a new strategy based on the experience that you have? Commercial real estate is lucrative, but the barrier to entry can be a whole lot higher than just buying a single-family home. So I'm curious to know how you would start over and why you would make that choice.
14:08 Speaker 02 Okay, so if I were to start over today, I probably wouldn't change anything, just because, yes, I'm going into the commercial space now, but I think single-family rentals truly built me a foundation, like, understanding how to underwrite basic properties, how to make offers, how to structure deals. You know, everything in the commercial side is still that stuff, but everything is just bigger, right? Um, you add more zeros, you have a couple more things to look at when you're underwriting and structuring deals. But what I would say is like, I probably wouldn't have gone as fast as I did if I restarted just because it's not really a race, right?
14:48 Speaker 02 And I think, I think a lot of people like just watch videos online or they listen to podcasts like I did. And I was like, I need to go buy a ton of assets as fast as possible so I can quit my job. And that wasn't the recipe to me quitting my job. It actually gave me so much more stress than I like, thought it was gonna be. But I wouldn't change the actual strategy. I would still buy single families and you know, like I'm in the military. So the VA loan is like absolutely insane. Like there's so many awesome vehicles to buy single family properties or multifamilies, whatever. I would just take my time. It's okay to say no to a ton of deals. Like I feel like I was saying yes to deals just to make them happen. You know, especially with creative finance, like I was making
15:32 Speaker 02 bad deals into like okay deals. But when you like rewind the clock and you really look back, you know, it's not really worth it to like chase those deals till oblivion, right?
15:43 Dave Meyer? This is why I hate door count. This is why I hate the idea of counting how many doors you own because it incentivizes the wrong behavior, right? Like you learned it faster than I did. Damn, so good for you. But especially when you see your first one go well, you're like, oh, I'm just gonna do a million of these. But like you were probably super disciplined with the first one, right?
16:03 Speaker 02 Yeah, I mean, the first one was a primary residence, but I mean, obviously that was my first one. So I was like asking my realtor like 6,000 questions and then I flipped my first house. That didn't really go well, but when I started to buy like actual buy and holds, you should see the checklist I was going through, like trying to make these numbers work. And then as I started to like do riskier things with creative and all that stuff, I started making deals like out of nothing. I think that's when it got really dangerous for me because I was like, oh, well, I can buy this, you know, on terms or like I can buy it on order of finance and property tax, insurances. That goes up every year and like the numbers change. And some of my properties that were making five, $600 a month, only were making $200 a month
16:48 Speaker 02 because of all the rates, right? And all that stuff. So for me, like the $200 a month and having a bad tenant was killing me.
16:55 Henry Washington? First and foremost, Tim, thank you so much for the honesty and the transparency. Yes. Like, that is rare when people come on podcasts and say, hey, I did this. It didn't work out that well, but here's the things I'm doing to pivot. And a lot of what you're saying are realizations that investors come across and not all of them know how to recover from them. I also fell victim to the growing for growing sake. There were several doors that I bought probably between 2023 and 2025 that just don't perform well. They weren't the best deals. They weren't terrible deals, but interest rates were bad and expenses started to rise. Rents didn't go up like you expect rents to go up. And now you're sitting on this property and it's eating
17:40 Henry Washington? away at the cash flow from your good properties, right? That's just a realization of real estate. Now, the good part about real estate is if you have enough cash reserves and you hang on long enough, yeah, in 10 years, I'll look like a genius for buying those properties. But you gotta get yourself to that point. Yeah. And there's a lot of stress and sleepless nights that can come with, you know, having to hang on to something that's not performing well. Yeah. But when I look at that deal now, I've learned things. I learned it was too far away. I've learned it was too old of an asset to buy. Yes, the numbers work, but the asset's old and the maintenance was kicking my tail. And so now I'm realizing that it's a better
18:21 Henry Washington? decision to buy a better quality asset at a good deal price point rather than chasing a asset that may be older, that's an okay deal, because I now know my end goal is to own properties for the long haul that I can pass to my children. And if you buy a crap asset, even though the numbers work, at some point, you're probably going to look to sell that asset because it's old unless you're going to completely remodel it from top to bottom. So Yep. What I'm trying to get across to people here is take your time, just like what Tim said, like, you don't have to chase every asset and don't just look at do the numbers pencil. Yes, the numbers are the most important part, but there are other factors. How is it going to impact your lifestyle?
19:05 Henry Washington? Is it further away from your other properties? Is it going to be harder for you to manage? What's the age of the asset? Is it something that you want to keep forever? Are you only keeping it for a few years? Like you have to think about your lifestyle and how that property may impact your lifestyle, whether or not the numbers work. And, and, and that's just something that's hard to teach a new person when you're starting out. So it's good to hear an investor talk about those things.
19:28 Speaker 02 Yeah, I, I talked to a lot of my friends who are in the military that are looking to get and start in investing. And they're all trying to start short-term rentals. And, you know, one of my friends bought a million dollar house in Disney, which is a really bad spot.
19:42 Henry Washington? That sounds scary.
19:43 Speaker 02 Yeah, and, and she makes less money than one of my long-term rentals. She like barely breaks even, you know, managing that short-term rental because it's so competitive there. Right? And there's so many rules there with Airbnb and that location specifically. But people are chasing what they think that they can make. And they're rushing into these deals without really thinking about, does it fit their lifestyle? Like she moves every two years, just like I did in the military. So she's managing all this stuff virtually. And I'm not trying to like spread fear. I'm just saying like, you know, take your time.
20:15 Dave Meyer? It's spreading reality. Yeah. And I, it is like, I was talking to a guy last night. I had someone over working on my house and I was just chatting with him. He was talking about, yeah, he got convinced in 2022 to go out and buy a short-term rental. He had to long-term rental, he's still losing 600 bucks a month. And he's like, now I'm going to sell it. I don't want to be in real estate anymore. It's what we talk about all the time. Like he had the right intent. He rushed into it. I think he would admit that he was saying this. He didn't really think about it that much. And then you're doing the one sort of cardinal sin as a real estate investor, which is just like not setting yourself up to stay in it the long run. That's the only thing you need to do with the first deal. And if you're rushing into it, that is the biggest risk, that a hundred percent the biggest risk
20:59 Dave Meyer? and much bigger risk than waiting six months to learn a little bit more, three months to find a better deal. Like I know it's exciting and you just want to do it. But the number one thing is to stay in the game, not to get the deal as quickly as possible.
21:12 Henry Washington? Absolutely. And you said that you would. Start the same way again by doing a single family home because it allows you to learn the skills necessary that you would apply to a larger, more risky, more dollar sign value asset. Right? And you're absolutely right. You've learning how to underwrite single family is a great baseline for learning how to underwrite other deals, learning how to select tenants properly, learning how to manage tenants properly, learning how to operate your business are all lessons that you're going to learn and we're all going to trip and fall and screw up. But when you do it on a single family home first, you protect yourself because you're
21:54 Henry Washington? probably not going to go bankrupt if you make mistakes on one single family home.
21:58 Speaker 02 Yeah.
21:58 Henry Washington? If you are, then you probably shouldn't have bought that single family home to start with. Probably weren't in a good enough financial position to buy it. But most of the, starting a single family allows you to learn, grow a baseline so that now you can go and pursue larger assets and take on more risks, especially for someone like you who's considering raising capital and syndicating a deal because now you're playing with somebody else's money. And I would be much more comfortable lending money in a syndication to somebody who's been there and done that, who's gotten their reps in.
22:32 Speaker 02 Yeah.
22:32 Henry Washington? Right? Versus somebody who's just starting out on a commercial asset. They've never done a deal before. That just, it's also going to help you be able to raise money, but, but using other people's money is a massive responsibility.
22:43 Speaker 02 Yes.
22:44 Henry Washington? And so getting your reps in on single family is huge. And again, can you go directly into multifamily? Sure. I mean, you can even go directly into commercial, but I would say if, if that's something you're going to do, you need to have a superpower like Tim has, right? Like you need to have like a partner who has experience in that, who's going to do the deals with you if you're just going to skip over the single and small multifamily to start out with.
23:10 Speaker 02 Totally.
23:10 Henry Washington? But if you have no experience, it's so risky.
23:14 Speaker 02 Yeah.
23:14 Henry Washington? To just jump off and do that because you can go bankrupt if you do a bad, large scale commercial real estate deal. That can hurt you substantially.
23:24 Speaker 02 Yeah. And you're losing everybody else's money too. I would not do commercial, honestly, if I didn't have my partner. I still think it's scary.
23:32 Dave Meyer? Yeah.
23:34 Speaker 02 You know, just looking at the numbers and stuff. So yeah, I 100% agree. Just building that credibility too.
23:40 Dave Meyer? It's big numbers and just complexity. You're giving up the, I think the best part of residential real estate or real estate in general is this 30 year fixed rate debt, which is incredible. Like you're giving that up, you know, it's a lot to think about. You can make a ton of money, but it is, it is something serious. So Tim, love the fact that you would do your first deal over again. I think if it was up to me, I would do my first deal all over again, but that's not available anymore. But I'd love to get some specifics from you. Like what about your first deal did you really like? So our audience can learn from what you've done, whether or not they're looking for their first deal or just trying to scale like the way that you have over the last couple of years. Let's get to that, but first we got to take a quick break. We'll be right back.
24:23 Dave Meyer? For my wife's birthday, I wanted to make her a new website for her landscape design business. So I researched a lot of different options. I tried out a couple, but honestly, it was really overwhelming. It was pretty time consuming and still the site wasn't coming out the way I wanted it to. Then I tried Hostinger and everything was super simple. I asked Hostinger's AI to build a clean site for her business and it had a working version up in minutes. No coding or designer needed. Plus it's AI agent helps with SEO, website copy and email marketing after launch. You get domain, website, email, all in one account. And right now you can get Black Friday and Cyber Monday pricing through December 14th.
25:07 Dave Meyer? So snag Hostinger services at their lowest prices before the sale ends. Create your website today for just a dollar 99. Go to hostinger.com/real estate and use code REALESTATE for an additional 10% off Black Friday and Cyber Monday pricing.
25:23 Henry Washington? Buy smart, drive for less, and trade for more. That's Toyota Fordability. And it all starts with a great deal from your local Toyota dealer. Make a smart buy on an all-wheel-drive Camry, Corolla Cross, or get a Corolla sedan packed with the latest features, advanced tech, and head-turning style. Take a test drive in two of Toyota's most popular SUVs, the spacious, family-friendly Grand Highlander and adventure-ready RAV4. And with so many hybrid and plug-in hybrid models available across the lineup, plus efficient all-electrics like the BZ, BZ Woodland, and all-wheel-drive CHR, you can drive your way and skip the pump. And long after you leave the lot, your Toyota keeps delivering with legendary resale value built on a reputation for quality and reliability.
26:08 Henry Washington? So when it's time for your next Toyota, you could trade in for more from a great deal today to a great value tomorrow. A Toyota is right for you. Shop toyota.com for deals and details, or stop by your local Toyota dealer today. Toyota, let's go places.
26:23 Dave Meyer? I just booked a ski trip to Park City, and I've already got the whole thing planned out. Five days, first tracks every morning before the crowds show up, my knees reminding me I'm not 25 anymore by the second run, and an embarrassing number of overpriced burritos at the lodge. I don't even care. This is the trip I look forward to all year. But here's the part I actually appreciate. The practical side of my brain kicking in is that my place doesn't have to just sit there empty the whole time I'm away. I can list my space on Airbnb and bring in a little extra income while I'm out getting humbled on a mountain. And with the co-host network, I'm not the one handling all of it. You can partner with a vetted local co-host
27:07 Dave Meyer? who can create your listing, manage reservations, message guests, and even handle the styling. So I get to fully focus on my trip, and my place is still working for me the whole time. Find a co-host at airbnb.com/host. Investing in real estate has always been smart, but it hasn't always been simple. Now, it's both, thanks to the Fundrise Flagship Fund. The Fundrise Flagship Fund launched more than five years ago. With a mission of delivering low fee access to blue chip private market real estate. Today, the Fundrise Flagship Fund has grown to manage more than $1 billion of real estate on behalf of hundreds of thousands of investors, making it one of
27:48 Dave Meyer? the largest funds of its kind. For those who believe real estate has an important role to play in their portfolio strategy, the Fundrise Flagship Fund has positioned itself as both a simple and a smart option. Whether you're starting with $10 or $10,000, the Fundrise Flagship Fund makes adding real estate's unique potential for both passive income and consistent growth. Just visit fundrise.com/pockets to make your first investment today. Carefully consider the investment objectives, risks, charges, and expenses of the Fundrise Flagship Fund before investing. This and other information can be found in the fund's prospectus at fundrise.com/flagship. This is a paid advertisement.
28:30 Speaker 03 At Edward Jones, we believe rich is about taking care of what gives your life meaning. That's why your financial advisor personalizes your plan to help you preserve your progress and create something that lasts. Let's find your rich. Edward Jones. Member SIPC.
28:49 Dave Meyer? Welcome back to the BiggerPockets Podcast. We're here with investor Tim Yu talking about what he would do over again if he was starting again from scratch. Tim only started in 2022, but he's done a little bit of everything, which makes him a great candidate to talk about in current market conditions, what would you do? Tim, you said before the break that you would basically just do what you did over again. But tell us a little bit about the deal. What about this deal, other than the fact that it was just a single family, like made it such a good, meaningful deal for you?
29:19 Speaker 02 Yeah, so my first buy and hold was actually a duplex. So I guess residential multifamily, but it was a little bit of luck, too. So like, looking at the numbers, it was on market, so it wasn't anything crazy. It was listed by an agent. We just went to go see it. We made an offer on it and we went conventional. So this property makes me like $800 a month. And the reason why the guy sold it to So cheaply is because he actually got married and was moving forty minutes away. And he lived in one of the units, so he just house hacked it. So for us, it was more of like a luck thing as well. The tenants are have been great. I've had the same tenants since I bought it four years ago. And I I keep them in every year. I talk to them every Christmas and I'm like, hey, do you just want to like stay in the property?
30:04 Speaker 02 And they're like, yeah, absolutely.
30:05 Dave Meyer? Great, awesome.
30:07 Speaker 02 You know, we're not trying to raise rents or anything like that because they've been great. And and you guys know raising rents can lose a tenant. And then now I'm paying a mortgage for for two months trying to fill it. But I wanted to say this too specifically was, you know, I bought this on conventional financing because I had a job and I was bankable at the time, so.
30:25 Dave Meyer? Nice.
30:26 Speaker 02 Don't rush to quit your job necessarily because I'm going to go through a lot of pain quitting my job right now. It's I'm losing the salary, I'm losing all the bank loans that I could qualify for. So there's pros to still having your job as well.
30:38 Dave Meyer? Absolutely. I mean, I think this is an amazing choice. I know everyone gets into this for financial freedom, but first deal, if you can hang on and just stay in your job, do it. I rarely give like blanket advice, but just do that. It is just so much better. You're going to be bankable, you're going to have less risk. You know, if you have a job with healthcare, that's going to matter a lot. There's so many things that you need to be learning about real estate. They're not so hard that you can't do them while you're working a full time job. And for me, I would rather do that when I'm not worrying about, am I getting this extra two hundred bucks a month? Because I need that to pay something like if I can live off my salary, that puts you in the position to go out and buy a good deal the first time around.
31:19 Henry Washington? I think people fall in love with the idea of not having to go to work for somebody. And that makes people want to grow and scale quickly because that's the idea that I fell in love with. And then, once you get to the point where you're full time, real estate is a little different because now it's not a side hustle, right? Now it's, I gotta do it to feed my family. And so it makes making good decisions harder. It's a different ballgame. I enjoy real estate wholeheartedly. But if I didn't have to quit my job when I did, I would have kept it longer. I just, it didn't make sense for me to keep my job any longer.
32:01 Henry Washington? But I waited as long as humanly possible before I left that job. Or I would probably still be working it, or I would have at least worked it a whole lot longer than I did. Now, I respect the idea that like, hey, buying a duplex, starting out, great decision. And it sounded like it was a pretty decent deal. But is there maybe a particular good decision that you made that you feel like I would make this decision again? If I were starting out, or maybe is there a particular lesson you learned or something that kinda?
32:32 Speaker 02 Yeah.
32:32 Henry Washington? Kinda hit you the wrong way that you're like, I would absolutely never, ever do this again.
32:37 Speaker 02 I would probably say, if you're curious about a strategy, go try it, right? You're never gonna learn more than just actually doing the type of deal. Like, I think every deal you do, you learn so much, either good or bad. The reason why I rather wholesale is because I don't like the actual idea of flipping. Because I got my butt handed to me on a few flips when, you know, I bought a house on a main road. I didn't know at the time that when you buy houses on super busy roads, the property value drops. And then like, I couldn't sell the house at the price that I thought it was gonna sell. That was one issue that I learned.
33:14 Henry Washington? Yeah.
33:14 Speaker 02 And then another one was, I don't do full guts anymore. Cause I tried a full gut on a hundred and twenty year old house in Kentucky. Like, everyone in Kentucky knows me about that deal. It's because it like ruined my life. It was so hard to deal with. So as you start trying different things, you start to learn what you like to do, what you don't like to do. If I were to flip houses, strictly cosmetic.
33:37 Henry Washington? Yeah.
33:37 Speaker 02 I don't know how you do it, Henry. I know you do new devs and all that stuff. But me doing that renovation, like, almost killed me.
33:46 Speaker 02 I know what I don't like, so. And then the biggest lesson I learned is if you're buying real estate, you're buying flips. When you do buy a bad deal, because. This does happen. You're never gonna hit a thousand for a thousand. You're always gonna have a bad deal or two. Is that the active income that you have either from your W two or a flipping business or whatever the case may be, that's gonna save your butt down the road. Yeah. So don't rush to quit your job if you have properties because some of the bad deals that I bought, my W two salary saved me. Right? I can eat mortgage payments because I had a job.
34:19 Dave Meyer? So it sounds like if you were starting over, you would do deal number one, the same, but maybe deal two through 12, you would do a little bit differently?
34:28 Speaker 02 I would say the flipping, I could probably live without now, but it was a great skill, right? I know how to renovate properties now, but yeah, not my cup of tea, honestly.
34:37 Dave Meyer? So what would you have done differently, Tim? Would you just gone do more wholesaling? Cause like, it sounds like you made some active income or would you just have gone straight to commercial sooner?
34:46 Henry Washington? Sounds like you needed to learn how to underwrite a little better on them single families you were buying.
34:50 Speaker 02 I would agree with you on that is underwriting way more conservatively. It's probably the recipe to success.
34:58 Henry Washington? No, it's absolutely the recipe to success.
35:01 Speaker 02 When you're like penciling deals, don't like fudge the numbers to like make a word.
35:07 Dave Meyer? No, I do everything I can to not buy a deal. I think that's like just the general approach is like, how can I make this look so bad? And if it still looks okay, I'm like, okay, fine. I'll buy the deal.
35:18 Speaker 02 That's the right mentality, honestly.
35:19 Dave Meyer? I just think that's the way to approach this. Like, why take on risk if you don't have to?
35:24 Speaker 02 Yeah, I agree. I was a young man, just, I was deal hungry, right? I just wanted to stack deals on my bill and be happy that I had all these doors.
35:31 Dave Meyer? I don't blame you, man. Everyone does it. Like, it's just a common thing that everyone does. And we just appreciate you being honest about it. That was kind of the whole idea behind this episode is like, share the real things that you would do differently if you were starting over.
35:45 Henry Washington? I think the real value people are going to get from this is that like you did deals that weren't profitable, but you're still here.
35:52 Speaker 02 Yep.
35:53 Henry Washington? Talking about investing, pivoting strategies.
35:55 Speaker 02 Yeah.
35:56 Henry Washington? Doing something that's going to allow you to live the kind of life that you want to live. Like, that's the best part about real estate. And so, yes, I want to be real with people and say, you can screw up. You're gonna screw up.
36:09 Speaker 02 You're gonna, yeah.
36:10 Henry Washington? I have a deal right now that I am trying to sell that I am going to lose money on, but it is one of several deals that I made money on.
36:18 Speaker 02 You don't have to bet a thousand.
36:20 Henry Washington? You're gonna screw up. Experienced investors make mistakes every day, but how do you pivot? What were the things that saved you and allowed you to continue to be here today? So what would you say is maybe one thing that helped you? You said your W2, having that income steady was one thing that saved you. Was there something else that like really helped you continue to maintain and not just give it all up like the guy Dave talked to yesterday?
36:49 Speaker 02 Yeah, that story alone was crazy, but I would say like, obviously my W2 and then I did active income stuff with real estate, right? So I did flip houses and I do wholesale.
37:00 Henry Washington? Yep.
37:00 Speaker 02 And those quick cash conversion cycles coming into the business, it gave me a lot of space to make riskier decisions in the buy and hold sector. I don't recommend going as hard as I did, but having that cushion in the background always was always kind of a safety blanket for me. So definitely upping your active income, either through working a higher paying job or doing something to make active income in real estate.
37:25 Henry Washington? Yeah.
37:25 Speaker 02 Is super awesome. And obviously with active income, you can buy properties for like tax depreciation, right? I think that's like.
37:32 Henry Washington? Yeah.
37:32 Speaker 02 The cycle of life.
37:33 Henry Washington? All right, Tim, you're now moving more into commercial. Can you maybe give us some specifics around like, how much cash are you looking to generate on a monthly basis that's going to allow you to not have to work a day job versus kind of where you were in the single family space?
37:52 Speaker 02 The asset classes that we're looking for is obviously the commercial strip mall area and we're looking at the Sunbelt location. So down south, super favorable market and all that stuff. And we're looking for outside of metro cities. But what we're looking for is if we can get an asset class that can generate three to $5,000 a month in net cash flow. That's after debt service and all that stuff. That is very possible.
38:16 Henry Washington? Nice.
38:16 Speaker 02 With the passive income of the properties that we have already, and then the active side won't really stop. Having that property that fits that that buy box is ideal.
38:25 Henry Washington? Yep.
38:26 Speaker 02 Which kind of sums up everything that we talked about is we're not rushing to go buy a deal right now. We're taking our time and we're doing our due diligence on that.
38:33 Henry Washington? So three to five K net income a month after all expenses. About what kind of purchase price point does that put you around for a commercial asset for people's reference?
38:45 Speaker 02 I would probably say if, obviously, we're trying to buy at a 10 cap. So the purchase price would be ideally like three million or under. But obviously sellers nowadays are not going to sell at a 10 cap. But that's the price range that we're looking for is probably the three to five million range.
39:01 Henry Washington? So a three to five million purchase price, is there expected renovation? Like is this value add similar to single family? If you want to get to those cash flow numbers or are you able to just buy something that's already producing that kind of net income for that price point?
39:15 Speaker 02 So most of these strip malls don't really require any renovations because the tenants themselves most of the time will be on triple net leases. So most of the time we do a triple net lease, like you can negotiate that the actual business owner that comes in can actually renovate the unit themselves. So it becomes more of like a mailbox money type thing. Once you have the right tenant in place.
39:38 Henry Washington? And then for financing these assets, I know most people use some sort of commercial loan for local banks. Are you looking to raise capital for the entire purchase? Or are you going to raise capital just for maybe what your down payment would be for that property? And then get local financing from a regional bank?
39:56 Speaker 02 There's two ways that we're going to look at it. So one way is since that strip malls are commercial, a lot of the owners actually are open to owner financing. We obviously prefer doing an owner financing deal and then raising the capital privately to do like the down payment and whatever holding costs and reserves are. If we do go the more traditional commercial banking route, we would do the 75% loan to value of the property and then we'd still raise that down payment privately. So that's our idea of how we're going to structure it.
40:25 Henry Washington? And real quick, before we get out of here, what kind of time horizon are you giving yourself to build up this cash flow? And this is just, are you looking to buy one asset that produces three to $5,000 a month? Are you looking to buy two assets that do that? Like, what's the time horizon? How many of these properties are you looking to purchase?
40:41 Speaker 02 Yeah, our goal is just to buy one this year. That's the beauty of commercial as well, is you don't need to buy a ton of deals every single year. You know, one deal a year, one deal every two years can change everything for you. So our goal is to close one this year. We're actively looking at marketing right now. So we'll see where that goes.
40:58 Henry Washington? I love it.
40:59 Dave Meyer? Awesome. Good for you, man.
41:00 Henry Washington? This man has learned from the past mistakes. This is, this is wisdom you hear speaking, folks.
41:07 Dave Meyer? We all get there eventually. It's just a matter of how quickly. How many times you gotta touch the fire before you learn? Well, congrats on your success, Tim. And, you know, I just love that you have thought about this and are building a portfolio that is designed for the life that you and your wife want. That's what it's all about. There's no right way to real estate investing, but your thought process is the one that I encourage everyone listening to adopt, which is like, what works for me? What do I need right now? No right answers, cash flow, appreciation, markets, strategies. The world is your oyster. That's the beauty of real estate, but you gotta have some discipline to figure out what works for you. And I really appreciate how you're doing that for yourself, Tim.
41:46 Speaker 02 Yeah, I appreciate hanging out with you guys today. Saw you guys in Vegas. So hopefully I'll see you guys sooner.
41:50 Dave Meyer? Awesome. Thanks again, Tim. And thank you all so much for listening to this episode of the BiggerPockets Podcast. We'll see y'all next time.
41:57 Speaker 03 At Edward Jones, we believe rich is about taking care of what gives your life meaning. That's why your financial advisor personalizes your plan to help you preserve your progress and create something that lasts. Let's find your rich. Edward Jones. Member SIPC.
42:13 Speaker 04 New and exclusive holiday decor just launched online at The Home Depot. Check out the viral Grand Duchess Collection with smart holiday lights you can control from your phone. Easily customize the twinkle across trees, wreaths, and gardens to match your holiday vibe. Create stunning light effects, then switch it up with the tap of your fingers. Even the man in red will be impressed. Shop the holiday decor you want, online only, at homedepot.com.
Previous The Financial Freedom "Stack": Start with No Rentals, Retire Decades Early Next I Had 4 Kids, No Cash, and a Traveling Spouse: Now I've Got 4 Rentals Page updated October 31, 2026 · transcript and summary are machine-generated
