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
Why I Haven’t Quit My Job (Even with 60 Rental Units)
Ever wondered why someone with 60 rental units would keep their day job? I'm breaking down exactly why I've chosen to maintain my career as a legacy airline pilot and military instructor while building my real estate portfolio.
The foundation of successful real estate investing isn't about quitting your job—it's about leveraging it. My steady income provides the financial safety net critical for those early investments. When I bought my first duplex, knowing I could cover the mortgage even if both tenants stopped paying created tremendous peace of mind. This stability allows for conventional financing rather than risky 100% LTV products that often lead investors astray.
Time management becomes your superpower when balancing multiple careers. I've learned to work efficiently during flights, leverage partnerships with friends who can check properties when I'm unavailable, and find service providers who align with my schedule. Getting my real estate license eliminated middlemen and finding responsive lenders who don't require constant attention freed up mental bandwidth. Most crucially, hiring excellent property managers transformed my business—they're not an expense but an investment as important as the properties themselves.
The math matters. Looking at my portfolio today, the 8% I pay in property management fees pales in comparison to my pilot's salary. Simply put, quitting doesn't make financial sense yet. I've witnessed investors lose control of 100-unit portfolios through poor management, creating financial death spirals impossible to recover from. Success in real estate isn't about timing the market perfectly or overnight results—it comes through consistent, methodical action maintained day after day, year after year. What's your wealth-building strategy, and how are you balancing immediate desires with long-term success?
What'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. Today I'm talking about why I have two-day jobs basically, yet I still have 60 rental units. Why haven't I quit? Why don't I do real estate full-time? Here's exactly why. First one, when you're first getting started in real estate and even now having a good-pay to get this duplex as my first foray into the real estate world, I'm just going to try to get my feet wet here. It's a good deal, but if no one pays rent, if both the tenants stop paying, I can still cover this with my day job. That's a huge benefit for you.
Speaker 1:No-transcript simple. I know a lot of people are going to talk about how you can finance this and finance that 100% loan to value, blah, blah, blah, blah. But in reality those things are tricky products and usually lead, lead people down the wrong path. They end up being screwed in the long term. So if you need money to put down on properties, it's as simple as that. If you don't have any money, then you need to go get money, and the best way to do that is to trade your time for money, which would be having a job. So in my case, trading my time for money, I'm all about it. You give me the money, I'll continue to buy rentals and I'm just going and I can take this business on its own. That's the plan. Long-term I don't know when that will be it's gonna be really hard for me to justify quitting my job as a full-time legacy airline pilot. Right now I'm in the infancy of my career and still doing okay, and I know that as I stay there longer, it's only going to get better. For now I'm just going to keep doing what I'm doing and eventually it will either be big enough for me to quit and then that question is answered on its own. So that's something that I look at.
Speaker 1:If you're just working a menial job and you don't care about it, the one thing that I always thought when I was working jobs I didn't like like at the post office, when I was working at five guys or dishwashing things like that I hated those jobs. But I always had in the back of my mind like this is moving me towards something that I really want. So I just was able to frame it in a way that actually made it okay for me and it wasn't really the end of the world. I still had days where I really hated especially the post office. I really hated that job. I felt like I was not using any of my potential, any of my brain power. I was just mindlessly walking through the streets of Milwaukee and I absolutely hated it. But I was able to frame that in a way that was productive for me, because I was saying I don't like this job, but I need this money to be able to buy some flooring for the flip house that I was doing at the time, or I needed to do it to go get some paint for the exterior or to redo the kitchen or a bathroom or whatever Like that stuff wasn't going to pay for itself. So I took but what?
Speaker 1:It wasn't a great situation for me. This is post flight school, so I was flying Blackhawks on the side and I'm delivering mail during the day, and it was just a really tough transition to go from flying and flight school every day to now. You're just, you're a nobody. You're back on the streets and I'm delivering mail in Milwaukee. I had to do it. There was no other choice. I didn't have another job to do at the time and that's how I framed it so it got me through those times.
Speaker 1:No-transcript. It's not beautiful, it's not pretty, it's not fun, and I wish that not everybody had to do that, but that's just the way it is. You have to accept the fact that these are the circumstances that you're in and then just continue from there. So that's what I've done for myself. And now it's not so bad because I'm doing a job I like and I feel like I'm getting paid appropriately and whatnot. But when you're not getting paid what you think you should be and your potential is being wasted on kind of a job that isn't really worth a shit, that's really hard to get through. So I can empathize with that for sure.
Speaker 1:Let me know in the comments what you're doing right now, if you're trying to build a real estate portfolio, what you're doing by day to try to get that thing going. One thing I would say on top of that is that a lot of people want to quit their job and then go full in on the real estate stuff. But you have to have a larger portfolio for it to really be something that you need to be hands-on all day, every day, with If you have two duplexes or one duplex or a single family house. That's not gonna be enough for you to justify quitting your job and occupying that same amount of time if you're working, let's say, 40 hours a week. So really think about it in a fact of okay, I might need to have a handful of duplexes or maybe 20, 30, 40 units before it really makes sense for me to do it full-time. And then also, what I think about is like right now I'm paying 8% to a property manager to run everything. If I was to take that 8% off the top and then give it to myself, let's say, as a full-time manager, how much is that per month? And I compare that to what I'm making in my normal day job and I'm like, yeah, I can't quit, which is a great place to be. I'm very thankful for that, but it is something to think about. If you're going to quit your job, that's making you 10 grand a month to save yourself $350 on property management fees. It doesn't make any sense, right, and you might just be trying to sell yourself a dream that doesn't make sense at this time. It doesn't mean that it won't work out down the road, but it might be something to shelf for now and revisit later. There's some time management hacks that can be done.
Speaker 1:I'm a terrible time manager. Anybody that knows me pretty well will know that I get everything done, but I'm very sporadic in the way that I do it. I'm very efficient at night, but I'm not very efficient during the day, and I know these things about myself. But a lot of things that I do is when I'm working. When I'm gone on trips, email and texts and calls and stuff. I try to have people that are around help me out, for example, when I was having other people do it for me because I needed it and they were gracious enough to help me out and take a look for me. So that's something that I always think about is trying to leverage other people that are also trying to get to the same goal as you or interested in the same thing. Trying to use friends, family and things like that to help achieve a goal together is amazing. That's what goes in hand with the partnership thing. I found partners that were home when I was not and I could reach out to them and say, hey, I'm not home right now, but could you take a look at this property for me? I know it's a pain, but would you just take a peek at it and let me know what you think? And that stuff has worked wonders, especially for a job like mine, where I'm gone a lot and I'm not always home to be able to do it myself. Doesn't always work out that way.
Speaker 1:The next thing that I would go with, on top of the time management stuff, is go get a property manager. I can't stress this enough, that getting a property manager is going to be, for the most part, the key to your success. If you're a one-off person that wants to manage everything themselves and you love the game of property management, then that may be for you, but for the majority of people it's going to burn them out, they're going to hate real estate and they're going to end up selling too early and they're going to end up leaving a lot of money on the table or taking a loss. So I can't stress this enough Go find a property manager. Go meet a hundred property managers in your city or in your town, whoever's out there operating and that you can find readily on the internet. Go meet with them. Go talk to them, explain your goals, see what they do.
Speaker 1:No-transcript, huge benefit. They're doing it day in and day out. They know the ins and outs of every property. They know the ins and outs of the laws and the rents. They understand what rents should be. They understand turnovers, they have crews to do gutters and siding and roofs and unit turns all these things that can eat away at your profit margin and or cause a good deal to go bad. I can't tell you how many deals I've seen. As a matter of fact, I almost took on management a while ago with my buddy. We almost took on management for 100 units that were owned by outside investors from Texas and somehow I got in contact with them. I don't exactly remember how, but I get in contact with them and they tell me yeah, we've got these. 100 units are being managed by one person and these are all in the hood. So they're all very challenging to deal with if you're not doing it full and day in and day out and you understand the game.
Speaker 1:And they wanted property management to come fix it and at the time I think they had about 15 to 20 units that were occupied and of those, maybe 50% of those were paying tenants. Otherwise no one was paying. People were just living in the properties. It was complete disrepair. It was insane.
Speaker 1:And these people had these properties for maybe four years, but they had slowly let them fall out of their control and eventually, once you get through the tipping point, you're not going to be able to afford to get the properties back to where they need to be, because the cash flows slowly start getting decreased, all the expenses start adding up and eventually you just can't even cover your bills, let alone try to fix things up, and then it just keeps feeding itself. It's a death spiral. Honestly, it really is a death spiral and we watched that one unfold and I don't know exactly what happened. I know they sold the properties to the biggest investor in Milwaukee, yusuf Barada, but I don't know what happened to it after that. I just know that they were in a terrible situation. They took what was a really great deal honestly and turned it into just a horrible situation. Sometimes there's no recovering from that. You'd love to think that you can always recover from these situations, but a lot of times if they get too far out of hand, it's game over. So I cannot stress that enough. Go get yourself a property manager and go meet with people and talk to them and try to get an understanding of the game and see who's real and who's legit and who's just blowing smoke, and then invest in those people. They're an investment, just as much as the property itself is an investment. So look at it that way. Don't look at them as they're trying to steal money from you or whatever. They're running a business just like anybody else. You just got to find the best operators in your city and go with that.
Speaker 1:How did I make it work for my first couple of deals? First house was a flip house, so it's pretty simple. I could do that while having a job. I was working there doing stuff after hours when we're done with work for the day and whatnot, and that's a thing that you might have to do. It may not be convenient. You may not be able to do it on a Tuesday at whatever 10 am. It's going to be at Saturday night when you want to go out with your friends and instead you're at this stupid house working on it at 9 pm. And those are the kind of sacrifices that I was more than willing to make and I did and, granted, it still hasn't necessarily paid off in the same way that I was hoping it would at this point, but I have a feeling that I know where this is all headed. So I do think it's going to pay off and in a way it really did, because that house turned into an eight unit, turned into multiple duplexes, turned into, you know, 60 doors now, plus a bunch of places I've sold along the way. It was cheaper for my friends and I to do it versus hire it out, so that's what we ended up getting my real estate license and becoming a realtor. I hate sales, but I got my license so I could represent myself and work my own deals, and that stuff is really simple to do on the road and when you have a job. It's a couple of emails here and there filled a couple of forms. It's really not that big of a deal. So that's something else that you could do.
Speaker 1:You can try to eliminate some of these characters that be challenging to deal with by being it yourself Be your own realtor, maybe be your own property manager, if you think you can handle it, and do all these other things while you're also working your job, to try to learn the whole game in and out and then be able to represent yourself in it and make your best decisions on your own. A lot of times I can save some of the conflict that you have with working with a realtor. If I have a job, I need to see this house at 4 pm on Friday. Sorry, I can't do 4 pm is what the realtor would say because of my daughter's soccer game, and blah, blah, blah. Okay, I don't need any of that. I can just go do this on my own. I don't need the help of a realtor because I'm my own realtor, right?
Speaker 1:And so those are the things that you can do to help make the efficiency better and find deals, and of that is finding lenders that are easy to work with. There's some lenders that are going to just be it's me like pulling teeth to try to get them to work a deal with you. And then there's other lenders. I found a lender recently who I just send the information to, and they basically disappear for 45 days and then come back and say, okay, yep, it's approved, here's the appraisals, everything's good to go, we'll see you on closing on Friday night and I'm like, okay, like that's pretty cool. So having people like that are massive for me, because I can set it, forget it and wake up in 45 days and focus on my jobs and being good at my craft and my normal day job. So that's something that's really key, and you'll see that as you start to work through deals, you'll see what lenders really want to work with you and make it easy on you and what lenders make it really challenging and they're going to end up going way overboard with the due diligence.
Speaker 1:Yes, so it means, and what that means is you're going to have to answer a lot of emails, you're gonna have to fill out a lot of forms, you're gonna have to do a lot of things that may be a little overkill. So there's a balance somewhere in between. Obviously, you want to find a good bank that's going to be around for a long time if you're going to build a relationship with them, but you also don't want to be just getting killed with a hundred waiting for the crash. Any minute now, the 2006, 2007, 2008 crash is going to repeat itself and we're ready for it, and those people have been saying it for years now and it still hasn't happened. And it may happen.
Speaker 1:I'm not saying that it won't, but if you're just waiting and waiting for the perfect time to invest, you're going to wake up and you're going to be 70 years old and be like oh, I totally messed that up to myself and so I'm on the opposite side. I'm just going with speed and I'm increasing my speed. The more deals I get under my belt and the more leverage I have to make deals. When I was starting out, I was a little bit more cautious, a little bit slower with my deal making, and now I'm trying to pick the pace back up and start making some moves now that we've built some equity and have a viable business. Don't let life just pass you by because you're waiting for the perfect time. There's never a perfect time. There's never a perfect time. The best time was probably yesterday, so get after it today is what I would say. The next thing, the last thing, I would say it's a big thing.
Speaker 1:In pretty much any industry, the people that rise to the top are those that are consistent and keep that same intensity from day one to day 1000. Those are the people that succeed. There's a lot of people that have gotten into real estate alongside me, or I've seen get in and out of real estate while I've just been staying the course the entire time. Consistency is key. If you want everything overnight, you're probably going to get burned. There's a few cases where people actually make it, but the majority of people are going to get crushed.
Speaker 1:Being methodical but also being quick it's an interesting combination. You can be methodical and still be fast, but that's what I would recommend to people, because if you're just going to sit back, wait for the perfect time, or you're going to get hyper aggressive and want to overnight, you're probably going to get hurt on both of those. You want to be somewhere in the middle and that's what I think I've allowed myself to do by keeping my job. There's a part of me that wants to do real estate full time. It's just not the right time for me, if you know, with that as well, because I'm trying to make better content. Thanks for listening and we'll talk to you soon. See ya.