Tailwind Talks
Tailwind Talks is a podcast for high-performing professionals who want to build serious real estate portfolios without leaving their careers. Hosted by an airline and military pilot turned investor, it dives into actionable strategies for scaling your real estate portfolio while balancing the demands of a full-time job.
Tailwind Talks
I Bought $700,000 of Real Estate With 2.5% DOWN (Here Are the Closing Statements)
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Want a real look at how “no money down” strategies actually work when the ink dries? Cole, a legacy airline pilot and part-time investor, opens the books on a six-month push to acquire five properties with hard money, then roll them into a $504K portfolio loan appraised in the mid-600s by income approach and likely near $700K by market value. We unpack every lever: high-cost points, 14 percent interest-only payments, seller credits, rent and deposit prorations, and why timing—not magic—made a $200K equity spread possible with modest cash out of pocket.
We don’t just celebrate wins; we study the costs. You’ll hear how underwriting with a fast hard money lender ran into thousands per property, why a credit union later charged only $756 to originate the entire refinance, and how that delta can make or break a deal. We break down a wholesaled single-family with a steep assignment fee that still pencils thanks to strong rent and ARV, plus a duplex negotiated $30K under ask by self-representing and walking from a commission to win the price. Credits helped one standout close at just $995 out of pocket—paired with a reminder that credits aren’t free, they’re deferred obligations.
If you want a grounded playbook for scaling with minimal cash, this conversation delivers the tactics and the warnings. We cover packaging properties for a portfolio loan, why lenders favor the income approach on rental bundles, how to manage balloon terms, and what to do when stabilization drives $50–60K expense months. The message is simple: speed costs money; knowledge and discipline pay it back. Listen, take notes, and decide where this strategy fits your market and your risk tolerance.
If this breakdown helps you think bigger and smarter, subscribe, share it with an investor friend, and leave a review telling us which tactic you’ll try—or avoid—next.
Why I Went Quiet And What Changed
SPEAKER_00What's up everybody? My name is Cole. I'm a part-time real estate investor, full-time legacy airline pilot and a part-time military instructor pilot. For those of you who've seen my videos before, I apologize for my hiatus. Life has been really busy lately. I applied for a different job in a different branch of the military and had my dreams crushed. So there was that. There's obviously the holiday season, and I hope everybody here had a great holiday. So there was all that going on. There's a loss in the family. There's just a lot going on. And then I was also working, obviously. And this time of year is very busy for my military evaluations for flying. And then uh I was also flying my normal airline job. So all of that, plus all the real estate stuff. So it's just chaotic, and I just I can't dedicate a lot of time to this sometimes because this is not an income-generating thing for me. So I have to sometimes focus on that stuff, aka work and or family and all the other things that come with life. So apologize for that, but uh I'm back on it today. I'm here to kind of update you on a deal that I put together over the last six months. I used hard money, I use wholesalers, I put very little money into this deal. I think it totals out to somewhere around 17,000 between all of these properties. Got about a half million dollars worth of purchase prices, and it appraises out to about 660 to 680. I'd have to look and double check. Um, market value, that's income approach. Uh, market value is probably about 700,000, so about 200,000 in equity with almost no money down, right? How is that possible? Is that real? And to show you all this, I'm basically just gonna go through all my closing statements so you can see exactly what they look like, what the numbers look like, how much does a hard money lender charge? I'm gonna show you my favorite hard money lender and uh what they charge me to do business with them. And so uh you can get an idea of what this stuff actually looks like because on TikTok, on YouTube, on Facebook, people are talking about getting properties with no money down. It's so easy, a caveman could do it. What does it actually take? And is it something that makes sense? Uh, I think it's a decent idea. It can be, and in this case, it worked out. In a lot of cases, it doesn't work out for people. I would caution a new investor from doing it because it can be very expensive very quickly. And you're talking about thousands of dollars in just lending fees just to get the loan underwritten, and then you're gonna pay 14% interest only payments for six months. And if you're not ready to refinance by the end of that six-month term, guess what? You're refinancing for another six months, and you're gonna pay them another lending fee and another six months of interest only payments at 14%. So you can get yourself into deep trouble really, really quickly, but use correctly, use for the right deal, it can be really powerful. In this case, it was so uh that's what the idea is for this video. I've got a ton of other ideas with other videos. Right now, we're down to 73 units with another four to be sold off uh that are under contract. I've sold a bunch of stuff, and we've got about 30 units under contract, so it's gonna net out to be about 99 units uh by the end of February, middle of February, I'm hoping. And that's pretty exciting. That's a there's a lot of stuff happening. We're very we're super close to the 100 unit goal that was originally set. And now I'm setting my sights on to what might be down the road. I'm thinking probably 500 units is the next number that really speaks to me and really feels like it will make a appreciable difference in my life and my family's life. So that's uh where my mindset's going, and I'm not stopping anytime soon uh unless I die, which is certainly possible, or I go bankrupt. Uh so I'm gonna keep going. And uh this is what I hope to be the start of something really interesting. But I could also go out of business tomorrow, so who knows what's gonna happen. We've had a ton of expenses lately. The 10-unit package that I bought that I made a video about and got some decent traction on. Uh that deal has cost me tens of thousands of dollars in rent, aka we've had to put a bunch of money. We've taken rent money that we brought in other places and poured it into fixing these places to get them rented out. Shout out to my management company, they've done basically all the hard work for this stuff. I'm just making deals up, but it costs a lot of money. And the bills from the lenders, the bills from the insurance companies, that none of that stuff stops. So uh it's been a tumultuous time as far as the cash goes. But uh the light is at the end of the tunnel. We're gonna make it through this, and uh maybe I'll make some videos about exactly what the last couple months have looked like because it's been like$50,000,$60,000 expense months per month. And even though I'm working on an airline and whatnot, that is expensive. It adds up really fast. And uh, as you can see, I'm still living in an apartment, so not much has changed for me, but we're growing the business. It should be almost$10 million worth of real estate by the time this is all said and done, you know, end of February. Uh, and from where I even started doing YouTube videos, I think that's almost double as far as the overall value goes. So um that's interesting and something worth talking about, maybe. So uh if you've watched my videos before, you've interacted with me, please leave comments, thumbs up, thumbs down, talk some shit. I'm happy to hear it. I'm excited to interact with everybody again and hopefully leave things better than I found them last time. So, whatever you guys got, I'm happy to hear about it, happy to talk about it. And if you want more insight and stuff deals like this, let me know if this is a good video, bad video. The last time I did a screen share on my computer, it seemed like people liked it. So we'll take a look and see what happens. Appreciate it. All right, everybody, welcome to my computer. Here's the five closing statements, and then finally the loan statement at the end uh for these properties. I paid a total of 504, I believe it works out to be for these properties, and uh the value on the appraisal was 665 or 685, maybe. Um, that was using the income approach just based on what the properties generate as far as revenue. If you actually did it in terms of uh value, I would say they're closer to 700,000. But everybody thinks what they own is worth more than what it really is, so who really knows? At the end of the day, these properties, I bought them all with hard money using different types of tactics, some with closing credits, some with um not taking a commission, some representing myself, some having somebody else represent me. I'm all over the board, whatever it takes to get a good deal. Um, but I want to show you some of the tactics I use and what it looks like on the closing statement. Hard money is extremely expensive to use, uh, but you'll see how it kind of offsets itself uh with rent deposits and credits that you get. And none of that's free money. None of the credits you get on a closing statement are really free money. You're paying for it somehow. It's just a matter of when, really, and that's a timing thing. So sometimes it's worth taking credits, you know, for rents and things to offset uh an expensive lender like Mach One, who is an excellent hard money lender. Um, sometimes it's worth it uh because in the long run I know I'm gonna be buying into several hundred thousand dollars worth of equity, and uh I think that's a worthy trade-off. But anyways, I won't get too much into the weeds. We're just gonna go through each one, kind of give you a top-down idea of what I'm doing here, and then we'll talk about the loan at the end. I didn't include the appraisal, I probably should have done that, but uh you know, you're welcome to not agree with me with whatever number I spewed. I think it's 665 or whatever. It doesn't really matter. This loan's already been underwritten, and appraisals are kind of just BS, honestly, but that's for another day. Superior title is who was used for this. This is in Lautosa, Wisconsin, in the Milwaukee area. And this first one, Mach 1 lending, I blocked out some of the information. You guys know I usually do that. Uh, most of it's to protect the sellers. I really could care less about my stuff. It's mostly the sellers and anybody that's living at the property, you don't want to blow up their spot, and and they didn't ask to be in this video. So I bought this duplex for$112,000. Pretty decent duplex. The outside has wood shake siding, uh, you know, cedar shake siding on the upper, which I don't love, but the property itself was totally fine. Um, gets good rents, and I bought it for$112,000. I put uh some, I think the$2,000 of credit that's just earnest money, the credit that I put down. I end up paying Mach 1$4,400 to underwrite this loan, which is crazy because all these properties, all five of these wrapped up at landmark. The underwriting cost was like$750,$750 for those for a half million dollar loan. This is just$112,000, and they just charge up the ass for their lending. But they really are a great option. I mean, all I have to do is send them a simple email and they're on it. I don't have to deal with them too much. They're really, really easy to work with. They've been really good to me, but I've also given them a ton of money, so they you know, I guess they should be good to me. I'm probably not even one of their bigger clients. I'm sure they have other people giving them way more money, but forty four hundred dollars for a$112,000 property is kind of painful. But you'll see that I did get some credits up here for taxes and water, and all these statements look the same. So feel free to pause the video at any point in time and look through the line items. I don't want to spend too much time talking about it, but you'll see the the broker actually got paid 4% on this, which is above average. And that's because they represented me and the seller. They're somebody that's actually been pretty helpful to me. I've listed properties with them, even though I have my license. I've listed with them and given them money, probably about$40,000 over the last year because I like working with them and they get me deals from time to time. So it's an equitable relationship, I'd say. And it takes some pain off of my shoulders because I still have normal jobs, right? I don't really have a whole lot of time to dedicate to selling my stuff. So it's better to have somebody that knows what they're doing handle it, at least right now. Uh, and this one you'll see$2,500 is what I had to bring in plus the$2,000 of credit. So I brought in about$4,500 for this deal. This is a again a duplex. This will be the most expensive property I bought as far as money out of my own pocket. Next deal, this is a single family, got it for$68,000, put a thousand dollars down. Got a bunch of credits that you can look at.$2,700 I paid to Mach 1 to underwrite that loan. Tons of money, but they're really, really useful. And I end up bringing another$500 to close, so$1,500 on the single family that rents for about$1,100 a month. Moving on. Got ourselves a lovely single family here. This one's gonna be one that I actually bought through a wholesaler, so you'll see what they made on this deal. But uh the actual sale price is$45,000. I paid$65,000 for it. You can guess if you want what the difference is. I'll tell you right now, it's what the wholesalers made off of me. Got some credits, no credits for rents on this one because this was a single family house that was vacant when I bought it, so nobody was living there. I made a video about it, what it looked like when we started. I think it's rented for$15.99 or$14.99 right now. So at$65,000 plus another$10,000 in rehab, you're in it for$75,000. It's worth about$130,000 and it rents uh you know for$1,500. Let's say not a bad deal. But again, I'm paying for it.$2,400 for the initial cost of lending. This is just to get these loans started. So I'm already at like$8,000 of lending costs, and I haven't even made one payment to them. So they charge 4% of the value that they're that you're funding with them, and then another 14% interest-only payments for six months. So it adds up fast. But if you're using rent income and profit to pay for it, it's kind of a wash. The way I look at it is like I said, I'm buying into these places and they're now worth a combined value of about$200,000 more than what I paid for them. Almost a quarter million dollars, it cost me$10,000 or$15,000 in lending costs and plus the interest-only payments. But honestly, it's a it's worth the cost of emission, if you ask me. Continuing on, a bunch of different title fees and whatnot, these are all normal, but this is the miscellaneous section. This is what they got paid for me. Uh, one of them got paid$8,800, and the other one got paid$7,200. So if I could have gotten this house for$45,000, my god, that would have been a slam dunk deal. You could have made almost$80,000 off of this deal, probably. But instead, I had to pay the wholesalers, so I lost out on some profit there for sure. But as far as cash flow and long term, I think it's going to be a good buy and hold. Uh, so I brought another$179 to closing, and with my$4,000 down here,$4,100 of what I brought in on that one. The next one here is this is a beautiful duplex in bad area, but the duplex is awesome. It's got a beautiful garage, beautiful siding. The lower was already rent ready, so that was a plug and play$9.50 a month, I think, for that tenant or maybe almost a thousand. I put$3,000 down on this. This one I represented myself, so I was my own agent here, and you'll see that down here under commissions. Only one side got a commission because I represented myself and did not get paid a commission. Father's son owned this property. The son was the listing agent, so he actually got paid three thousand dollars to sell his own place minus whatever his broker takes from him and taxes, of course, so maybe like$1,500. But uh, you know, they wanted like$130,000 for this place. I got it for$100 uh because of two reasons. I represented myself and got rid of a commission. And honestly, the commission is not that big of a deal because three thousand dollars minus taxes in my broker's cut is really not that much money, honestly. And so to me, it's a psychological thing, though. A lot of people automatically are interested in your offer more if you take out the commission portion just because they feel like they're getting a one-up on you, and I'm cool with that. You can have that win all day long. Yeah, I didn't get paid a commission. Darn, how will I survive? Meanwhile, I'm getting this thing for a hundred grand. It's gonna rent for$1,900 a month once it's stabilized. The upper is kind of low right now. I think it's like$600 a month. And they they previously got evicted from my management company that's now managing this property. So when she found out I bought this, she called me and was like, Oh my god, please don't evict me. This and I was like, Hey, no one, nothing's happening. But she had been evicted by them in the past, so um, anyways, uh interesting situation. But when you look at this stuff, to me, it's like, oh yeah, I'll leave my$1,500 net commission off the table if that means I can get it for$30,000 cheaper. You know, that's 10 times more money. Anyways, that's just one way to look at it. I'm a big numbers guy, the little numbers like that. I'd rather forfeit that for the long-term gain. But you have to be a long-term-minded person, and it can be really hard to think of it in that context. I've got some people in my life that they cannot stand to think about things in the long term. Um, and in this business, you really, really need to because you're gonna get burned if you if you try to live for day-to-day. Um, I brought 642 here, so my total in was$3,600. Next one and the last one for this deal is a duplex, beautiful duplex in a great area, bunch of credits. I got some credits on this one. So I talked about I wasn't getting some seller credits for this deal, and one that's not included in this refinance. I got a total of$5,000 in seller credits. Seller credits, um, you know, it's not life-changing money, you know,$2,500 for this deal. But I didn't put an earnest money down on this deal at all. You look, you can look through the statement. I never put any money down on this, and guess what I brought to close?$9.95. So yeah, I paid Mach 1 their huge lending fee,$6,400. I paid all these people their money, but in reality, the money that came out of my pocket was$995. So they got paid their fee through all these credits. And again, this isn't free money because I'm not getting August rent then. You know, I'm getting not getting the security deposits. When these people move out, I'm gonna have to give them back their security deposits. Like this money is not free, it's just deferred payment, right? So I'm deferring the payment on this stuff till later, and in the meantime, I'm getting uh a duplex for$160,000 with$995 out of my pocket. And as you can see, it is extremely easy to get high on your own supply with this stuff, right? You could get these loans underwritten non-stop and you could be buying stuff like crazy. Um, the reason I bought this stuff is because I thought it was all relatively undervalued, and it proved to be correct. You could also buy stuff that is overvalued and do the same exact thing and have no equity to play with. And when the time comes to refinance with a big bank, they're gonna make you bring another 20% and pay down. And when you add that into the lending fees and all the other fees, it ends up being horrible. It ends up being a terrible deal and it could put you out of business. So please take this all with a grain of salt. Understand that this is a this is not a a deal that can be made every single day. This is a one-off kind of situation. I end up accumulating a handful of these and was able to package them together and present them to a bank that I love or a credit unit that I love and uh let them go to work on it. So again, you can get high on your own supply, you can put yourself out of business before you even started with this stuff. At the same time, if you can find a decent deal and you're a newbie and you're just starting and you only have$995, you can structure a deal like this and get yourself into a duplex that's worth maybe$210 on a beautiful day for$160,000. That does exist out there. And these other deals, some this deal above, I got this off MLS. This was just sitting on MLS. Anybody could have bought this deal. I just happened to email the guy and say, Hey, this is what I can do. Is that something that's interesting to you? I can close in two weeks because I have Mach 1 on my side, right? I don't, you know, you can say it's a cash offer. They don't care where the cash comes from as long as it ends up closing on time and the money comes out the way they want it to. But yeah, it was it was a cash offer in parentheses, but mach one's the one that did all the hard work. They were the ones that brought the money. What I'm saying is the deals are out there, but you can, you know, you have to be careful, you have to be diligent, you have to know the market. And if you don't know the market, you need to find somebody that does. So I think there's a lot of value in knowing somebody that's directly tied to the market you're trying to buy in. And I think that's why living in the market that you're buying in might make the most sense in a lot of cases. But people live in places that are way more expensive than here. So, anyways, this is where it all shook out to be. Again, we're redacting some information to protect people and myself at this point, but again, I don't really care that much. It's just, you know, there's people, this either loan officer, and I don't need everybody involved. This is with landmark credit union, as you can see here. 1222-25 is when it started. So just before Christmas, it's gonna go mature in five years, which means there's gonna be a balloon payment. We'll talk about that in a minute. Uh, 6.1% interest,$504,000 is what I owe, and it's uh due 2030, right? So the way that works is when this due date comes, I'll just refinance this into a new loan. That's what people do. Is it when the balloon payment comes, you'll just refinance out of it into something else, either with that lender or somebody else, and keep the kick the can down the road for another five years over and over until the balance is paid off. As you look, you'll see a bunch of lending costs. The one that really matters, none of this stuff really matters. You know, this is all the payoffs for all the properties that I purchased. You can see the exact numbers right there. Um, and this is all extra interest that I didn't pay. That's why the numbers don't shake out exactly as you would figure they might. But the one that I thought was interesting, loan origination fee right here,$756. So they only charge$756 to underwrite a$504,000 loan. Meanwhile, you saw what Mach One was charging me to underwrite those loans. Absolutely out of this world. But that's the cost of doing business. That's the cost of having fast money like that. Um, but sometimes it's it's really applicable and it's really worthwhile. At the end, I will owe$472,000. So in the life of this loan, I'll pay down you know$504 minus$472. The difference of that is basically what I'm paying down. So I think that works out to be what$32,000. I don't even know if that's true. Maybe it is. I'm not gonna spend too much time on it. Um, but this is what it looks like. So this is with landmark reunion, this is who holds that loan now, this is who holds all those properties. I owe$504, it appraised, like I said, for like$665,000 or$685,000. I think that was the income approach. I think uh if you just go actual value, I think you're looking at$700,000. And and that's kind of one thing to keep in mind. Income approach versus like when they just compare to comps. Uh, income approach is basically just looking at what is the what is this property or group of properties bring in in terms of gross income, uh, and the you know, whatever net, whatever the net would be, um, versus the other approach, what most people most people would see with residential mortgages, uh, is based on comps and things that have sold that are similar sizes, similar location, similar lot size. They're gonna look at all that stuff, and that's how they come up with the two different values. In this case, since it's a portfolio loan that brings in, I think, around 10,000 gross a month, they said, yeah, it's worth this much based on the income. So well above what I paid. Um, I could sell this tomorrow, let's say I meet that value and maybe clear 150 grand and I put in 15, 16,000, 17,000. Not a bad return on investment, especially when you're talking about six months. This is six months in. You know, I haven't owned these for even a year yet. And so if I hold on to these for a while, I have a feeling I'm gonna continue to chip away at this mortgage, I'm gonna continue to get better rents and can refinance out of them in the future, cash out refinance, maybe, or maybe I stay the same and just do a rate modification when rates come down, if they come down, of course. Uh, but that's the idea. So, this is a deal that I did, this is a deal that anybody could have done, anybody does do from time to time. Uh, but I happen to pull this one together myself. If you have any questions, any comments, any thoughts, I'm happy to hear them. Again, this is just uh one example. I've got other things to talk about too. I've had some massive, massive expenses in my portfolio lately. So things have been a little chaotic uh because we bought a bunch of properties that you may remember that needed to be fixed up and cleaned out and all this. Uh, but this is uh this is one example. So any Questions, any comments, uh let me know. I'm happy to help. That's why I'm doing this. Is so that hopefully somebody out there gets something out of this and can institute it in their own life and build some wealth for themselves and their families. Again, appreciate all of you spending the time to listen to any of this. And I'll talk to you soon. See ya.