777 Training And Real Estate Juggling

I’m in that uncomfortable stretch where everything matters at once: learning a new jet, keeping my airline job safe, staying current in the military, and still moving real estate deals forward. I just wrapped up Boeing 777 ground school after years on the 737, and I walk you through what training looks like now from touchscreen cockpit trainers to a systems test built from a massive question bank. We also talk about the bigger shift happening in aviation: iPads, electronic checklists, and a training culture that leans less on deep “walk me through the system” knowledge and more on executing under pressure when the scenario goes sideways.

Then I switch over to the real estate investing update with real numbers. I closed a three-bed, one-and-a-half-bath single-family for $105,000 using hard money financing, including the upfront fee and the 14% interest-only structure. I explain why I’ll still pay that price for short-term capital, how the refinance plan works, and what “stabilizing” a rental really means before a local bank or credit union will want the loan. If you’re into BRRRR strategy, bridge loans, cash-out refinance decisions, and the tradeoffs between speed and cost, you’ll hear exactly how I’m thinking about it.

We also get into scaling: multiple houses under contract, appraisal delays, portfolio momentum toward 100+ units, and why you can’t build at scale with a single lender. I share how to handle bank rejection without spiraling, when to internalize the feedback, and when to move on. I wrap with the most practical advice I keep repeating to new investors: keep your day job early, reinvest cash flow, and treat a great management company as the foundation that keeps the whole operation standing.

If you got value from this, subscribe, share it with a friend who’s trying to buy their first rental, and leave a review with the question you want me to answer next.

Transcript

How Airline Training Has Changed

Simulator Phase And Failure Scenarios

Closing A $105K Single-Family Deal

Deals Under Contract And Appraisal Delays

Why You Need Multiple Lenders

Cash-Out Refi Strategy And Deal Discipline

Protect The Day Job And Reinvest Cash Flow

Management Company As The Linchpin

Questions Welcome And Sign-Off

SPEAKER_00 0:10

What is 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. Today is one of the days that I'm back home from training. I just finished ground school training for the 777 transition course in Dallas. And so what that looks like for me, uh, I was a 737 guy for a while for the last three years or so. And now I'm going to the triple, which includes a transition. It has two weeks of ground school, two weeks of simulator, and then a bunch of operating experience, which means going out and flying actual trips with Czech pilots to make sure that you know what you're doing, right? So I just finished the ground school portion, which is pretty exciting. That included basically two to four hours a day of sitting in front of computer screens that are touch screens that emulate what the cockpit looks like. And you do fake takeoffs, fake flights, fake landings, um, all pressing buttons and turning switches in the same way that you would in the actual airplane. And I did get a couple hours of actual simulator time, which is always nice because it's more realistic and you get more used to where your hand position is going to be and how everything actually works and looks in the real airplane. So I got through all that in the free time after class, uh, you would um basically be studying for the next day and the systems test that happened at the end of class. So the average day was about two to four hours, like I said, in front of the fake uh airplane computer screens, and then another probably two to four hours of ground instruction, which covered everything from the engines, hydraulics, flight uh controls, fire protection, emergency equipment, pretty much anything that it takes to operate the airplane, it was covered at some point to some level of uh depth in the ground school portion. But the airlines have started to transition away from deep systems knowledge that used to be really important. I mean, even when I went through flight training for the military, deep systems knowledge was uh basically a non-starter. Now, with the airlines, with the advent of the iPads and the their use and their integral use to the flight deck, the electronic checklist that the 777 has, um, these different things uh make the systems knowledge less of a priority for them. And I'm not sure if that's a good or bad thing. I mean, I think understanding your airplane and how it works is really important, just like understanding the real estate stuff is really important. But at the same time, like you basically just do what the checklist tells you to do. So I can see an argument for saying you don't need to know how every nut and bolt is attached to this airplane because you're not going to have really much choice when it comes to the checklist. So uh it's kind of interesting, it's a weird transition to see because, like I said, starting in the military, uh, there's a lot of people that would say, I'm an atom of fuel, you know, walk me through how I get through the fuel system in the aircraft. And you'd have to kind of know all that stuff and be able to at least articulate it to the point that it they could see that you understood it. So now it's just a hundred question test, and you have all the answers available to you. It's a bank of probably, I would guess, a thousand questions. You'll get a hundred of those, and you need to get an 80% to pass, and that's it. There's no oral, there's no, you know, sit down with the the instructor and they say, Hey, I'm an atom, I'm an atom of air, talk me through how I go through the engine and the different stages and compression and exhaust and all this stuff. They they don't really talk about that. So you pass the the test and then you just move into the simulator phase. And the simulator phase is really a validation or um increase in depth in your knowledge on how to operate the aircraft, especially in its you know, extended envelope training. So you're talking about stalls, you're talking about uh terrain um and how to avoid you know impacting the terrain and just like you know, all these different things, engine failures, bad weather, snowy conditions on the runway. I mean, there's a million different scenarios that you see, but that's the shift in focus now. So it's gonna be less about the normal operating procedures, and this next five days of simulator training should be more focused in on how to operate the airplane when things go wrong or when you do something wrong. So it's kind of interesting. It's just that's the way of the world now. When you have so much information right at your fingertips with the iPad, some of the information that used to be really important is a little bit commoditized now. So all that to say, I was gone training, pretty focused on that, didn't have a lot of time to dedicate to the videos, but I did get a closing done yesterday. The only business day that I was free and in Milwaukee, I got a closing done for a single family house. And that house uh I made a video about just previous to this one. And basically the idea three bed, one and a half bath,$105,000 purchase price. I financed it, of course, with Mach 1. I've talked about them in other videos. They're a hard money lender, so you pay them 4% funding fee up front, which is uh just over, you know,$4,000. You know, in your brain, you can do quick math and say, okay,$4,000 for every$100,000 you borrow. And I borrowed$105,000. So just over$4,000 to get the loan with them, and then it's 14% interest-only payments for the life of the loan until the six-month term comes comes due, basically. I've talked about them before. I've talked about why I do it that way, even though it's uh it costs an exorbitant amount of money to borrow money from them. But the reason I do it is because I can now uh have a little bit less money committed into the deal, I can focus on repairing it, getting it stabilized, and then refinance it with a landmark or a summit credit union, somebody local to me that will take on the loan. So that's a kind of a quick update with that one. Like I said, the last video talks about the actual house itself. I walk through the whole thing, so it might be a good one to go check out if you haven't already. And now what is coming up? We've got six single families that are under contract right now, and those will be closing hopefully in the next week or two. We haven't gotten the appraisal back, so nothing happens with the bank unless you get the appraisal done. You can have all the offers in the world, you can have all the money in the world, but if you can't get the bank to get their appraisal back from the company that conducted the appraisal, you're kind of dead in the water until that happens. So uh we got that going. We got another five single families after that that are closing that are all on the same street. I did a quick little video of those on the outside, and you can look back and see that. And then after that, we're not really sure. Um, I'm gonna do a portfolio update at some point to show you guys what everything looks like, how things have moved around. I mean, after all the dust has settled here, we should be at 106 units, which is cool. We're not bankrupt yet, so that's good. But as you guys know, I'm still working my day job, still flying for the military. It's this a lot, it's a big juggling act right now. We've got the possibility of refinancing one of our four families that we owe maybe 170,000 on. It's at a really good interest rate, but it's only on a five-year term, and the five-year term is coming due in December. So we're in the last year of that loan, and we don't plan to stay with the bank that we're with right now. For whatever reason, we're not a great fit for each other right now. And sometimes that happens. That's uh kind of a quick note, maybe to talk about is don't just have one lender because if you want to grow to any amount of scale, I'm in the midst of trying to do that. If I was committed to just one lender, I would miss out on a ton of deals, a ton of opportunity because not every bank wants the product that you're offering them, and vice versa. You might not want every product that the bank is offering you. So, this bank in particular, uh, they were awesome for a while. They were our we were going to them for every deal for probably three or four deals in a row. And this is back when we didn't really have many properties at all. This is while I was still, I don't know if I was still working at the post office at this point. I was past those days, but it was still in that influx of not making a lot of money at our jobs and didn't have a lot of properties. But this bank was willing to work with us, and the tide has turned. The guy that I was working with there retired, and so now we're working with somebody new who's awesome, but they just they didn't like the last couple deals that I offered to them, and Summit took them right away, Landmark took them, and I reached out to them recently and they said, Yeah, we're just not interested in your growth mode, basically. So sometimes you're gonna get that feedback from banks. It's not that we're insolvent, it's not that we don't have any money, it's just that some banks don't like the product that you're offering. Some banks want the nice and easy you've you know, you've owned it since the 1980s, you own nothing on it, and you just want to take a little money against it. They want something that they know that they absolutely cannot lose on. And when you're in the growth mode, they're you're taking a little bit more risk than others out there. So the one thing I would say about that though is if you're if you're getting feedback from bank that says, Yeah, we're not really too keen on this deal or on you, that's a moment where you should be pausing and saying, Okay, am I the problem or are they the problem, right? And you really should consider whether or not you might be the problem. Because if you're getting feedback from banks saying, Yeah, we don't want to lend on that, we don't want to lend on you, there might be a reason to that, right? It might not, it might not just be because they don't like you. It might actually be because uh you're doing something or you have too much risk somewhere that they don't like. So take that feedback and internalize it. Don't get too beat up about it. There's an unlimited amount of banks out there, so you don't have to be beholden to one and you shouldn't be beholden to one, but definitely take that feedback, internalize it, and then decide who's in the wrong, right? Or who's off a little bit. In my case, I determined that I was in the right and they're in the wrong, and it stayed true. I mean, I've done probably three, four, five deals in a couple dozen units since they kind of almost ruined a deal for me. And I went back to them just recently just to see, you know, just to poke around and see if uh it's back on the table and it's not. So I'm just gonna leave them in the dust and keep moving. And it might turn out that they are right in this whole situation. I maybe I'll make a mistake, but right now I just think that they're a little bit risk adverse, and that's okay. But, anyways, back on to the topic at hand. Uh, the idea basically is that we have this four-family, it has a lot of equity. We want to refinance, cash out refinance the equity and deploy it into a new deal to buy more properties and continue this trend. We need to get them at a good price, right? Obviously, you don't want to get overextended, you don't want to borrow money against one of your existing properties to then buy overpriced other properties because now your risk has just gone way, way up. So it's got to be the right deal, it's got to be the right price, gotta be the right cash flow. But we're looking at duplexes and single families mostly right now. That's where I see the opportunities. Single families, especially, have such low expenses compared to a lot of these bigger buildings. The eight family that I used to own. It had a boiler, I was paying for everybody's heat, I was paying for electricity, I was paying for basically everything. And those expenses added up just for heat alone, it was seven, eight thousand dollars a year. So that it can really impact your bottom line cash flow. Not to mention the buildings like that that are in nicer areas and whatnot, their property taxes are insane. When I sold it, the property taxes were about$8,000 a year. Now the property taxes are like$14,000,$15,000 a year for the new owner. So that's a risk that you have to accept. Uh, things are always changing. Not every day is not the same as the last. Things are always going to change. You're gonna have to adjust fire as required. But I see the opportunities with the single families, with the duplexes, because everybody's chasing the multifamily, everybody's chasing that stuff. And I bought some of myself. I mentioned that in a previous video, and maybe I'll throw up some pictures of it here. I bought some of that myself in a 1031 exchange, but I don't think it was a great deal. I think it was a good deal, and I think it'll be okay for the long run, but it wasn't amazing, it's it's not gonna change everything for all of our lives overnight. So you have to kind of ebb and flow. And right now, I think single families and duplexes is where where all the deals are at. So that's what I'm focusing in on. So the next couple deals are almost all single families with maybe five or six duplexes thrown in there. And that's gonna require some refinances, that's gonna require some cash out going up on the risk scale. But I think it's a worthy risk to take, and time will tell if that's true or not. So that's kind of what's coming up ahead. My focus, admittedly, is on the simulator. If I don't pass the simulator and the airline I'm with fires me, that would be a detriment to everything I'm doing right now. So I cannot be fired. I cannot have any problems in the simulator. So when I'm out there, I'm pretty much completely focused on that. Doing a couple proformas and doing a little bit of deal making here and there, but for the most part, I'm focused on trying to make sure that I don't mess that up because that is my livelihood, and uh that is what keeps the wheels rolling right now. Because the real estate stuff, like I've told you guys before, is on its own island. No one's touching it, no one's using it, none of the none of the profit is being used to fund anybody's lifestyle. It's all just feeding back into the system because uh it takes a long time to build something that's worthwhile and can replace your own income. So everybody's committed to that cause. Everyone understands the mission that we're on, and right now that means that I cannot get fired at the airline. So I'm gonna do my best to keep my head above water. So far, so good, but anything can change any given day. So that's what's going on. And basically, once that's done, I'll be back here and uh get back to life as normal. That means I'm gonna have to get back into the military flying. I can't neglect that for too long because uh if you don't use it, you lose it. Those skills fade over time. And if I don't get back in the aircraft, I'm gonna lose those skills. Airline flying, it's more of systems managing, so it's not really flying. So just because you fly in an airline doesn't mean that you're good at flying in the military. They're kind of totally different things, in my opinion. And then it'll be back to deal making, they'll be back to more closings, refinances. Hopefully, cash flow will start to stabilize. We've already seen that this month because a lot of those vacancies that I had that you guys know about have been filled. We bought a lot of stuff that was vacant and needed work, it costs a lot of money, but now we're getting back to stable. So we'll hopefully be able to pay down some of the debts that are owed to me and to elsewhere while trying to stabilize everything. So that's kind of what it looks like. In the midst of all this, I really think uh one of my biggest recommendations if you're starting out, keep your day job. Do this on the side. Don't make this your full-time income. If you're dependent on everybody paying their rent on time, uh month by month, you're setting yourself up for potential failure. So keep that in mind. If you're just getting into this, if you just started, if you haven't even started yet, just get comfortable with wherever you're working at because it will pay dividends down the road. If you can delay using any of the rental property income, any of the cash outs, any of the sales, if you can delay using any of that for your own lifestyle for as long as possible, it's gonna allow you to grow as fast as possible. Imagine it like a 401k. If you kept taking loans against your 401k throughout your career and throughout your progression through life, it's gonna stunt the growth of that 401k. It's the same idea here. If you take money out and deploy it to your own life, it's gonna slow things down. And that doesn't mean you shouldn't enjoy your life. But if you have a normal nine to five job that's being able to pay the bills and fund the things that you want to do, just chill with that, enjoy it, and revisit it down the road because the snowball is slow, especially at the start. The last, the first 20 units are the hardest ones, right? You have no money, uh, the deals are hard to find, you don't know anybody, you have nothing, and you're trying to build from nothing. And that's what we did with that single family house that I mentioned. And it takes so much time. So just leave it alone, let it be its own thing, and it really reduces your risk then, too. You're not as concerned about bankruptcy and not being able to pay your bills because your bills are just being they're just within the real estate circle. They're not your car payment, they're not your house payment, they're not your vacation. It's all within that ecosystem. And I think that's one of the biggest pieces of advice I could give to a new investor if you can withstand it. If you if you absolutely hate your job, uh you know, there's people that have quit their jobs and have done better than me. So don't take my advice as gospel. But if you can tolerate your job or if you even like your job, stick it out, get a management company, a good management company. That's the key part. That's your probably biggest deal that you're gonna do is find a good management company that takes care of you and that understands your interests and you understand theirs. Um, I know this is like rapid fire information, but this is some of the stuff that comes to mind while dealing with some of my friends and people that know me that are trying to get into rentals. When they ask what kind of advice do I have for them, that's like one of the biggest pieces I have. The management company is the linchpin to everything. So that's just a quick update. I'm in the midst of 777 training. If you have any questions about that, let me know. I'm happy to talk about it. I tend to talk more about the real estate stuff, but I'm trying to incorporate a little bit more about my normal life because real estate, believe it or not, is not my normal day-to-day life. It's sitting in the simulator, it's flying the jet or in the military, whatever. So let me know if you guys have any questions about the deals, about anything. I'm happy to go into really long detail in the comments. I appreciate everybody's time to watch this video and support the channel, and I'll talk to you guys soon. See ya.