
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
Flying Jets By Day... Living In My Moms Basement By Night
The path to real estate wealth rarely looks like the glamorous stories we see online. Sometimes, it means making the uncomfortable choice to live with your parents well into adulthood or finding roommates to slash your biggest expense. That's exactly what I did – working as an airline pilot, flying military missions part-time, and gradually building a rental property portfolio while living in my family home.
Was it embarrassing? Absolutely. I was probably "the only instructor pilot in the Army living in his mom's basement." Did people make fun of me? Constantly. But I was playing the long game, looking through a 5-10 year lens while saving $10-15K annually – enough to purchase a duplex each year in my market.
When you're starting your real estate journey, those first few deals determine everything. They create the foundation and momentum for everything that follows. With modest income from regional airlines ($40K) and military service ($15K), controlling my housing costs made the difference between building wealth and merely dreaming about it.
For those unable to live with family, roommates offer similar financial benefits. During flight school, sharing housing with two others not only reduced expenses but created lasting friendships and memorable stories. The principle remains the same: housing typically represents your largest monthly expense, and controlling it creates immediate capital for investments.
This strategy becomes even more powerful in today's economic landscape, where inflation has outpaced wage growth. When you're early in your career with limited leverage to increase income, reducing expenses offers immediate results. Nothing should be off-limits when you're serious about building a portfolio – whether living at home, finding roommates, or reducing social spending.
The equation is simple: make more money or spend less. Since significant income growth takes time, especially early in your career, strategic expense reduction creates the financial margin necessary for meaningful investing. No one is coming to rescue you financially – only your consistent actions will determine your results.
What uncomfortable but strategic choice could accelerate your path to financial freedom? Share your thoughts in the comments, and subscribe for more practical, no-nonsense advice on building real wealth through real estate.
What's up everybody, welcome back. Today I'm talking about one of the things I did to spring more of my career, starting out living at home, which was not really fun at all and isn't a sexy topic, but it is super practical for people that are looking ahead. And even if you can't live at home, living with roommates, there's a lot of different ways you can kind of reduce your monthly expenses. And I think, starting out, if you want to get into real estate investing, that's one of the best things you could do for yourself. So, starting out, I literally graduated flight school, came back I was working for the post office delivering mail.
Speaker 0:Eventually I got a job with an airline and I was flying for this airline slash delivering mail before then and still flying for the military part-time, and I was living at home for the most part. I moved away a couple of times but eventually moved back and it wasn't really cool. It wasn't fun, like nobody's going to respect you because of it. But I didn't care because I'm looking at this in a five, 10, 15 year lens and I know that it's going to work out. And so there was periods of time where I was flying for an airline by day, flying for the military by night and I had maybe a couple dozen rental units and I was still living at home. So, like I, the value of my portfolio was bigger than probably the house that we were living in with my family. But to me it made sense because I was reducing my monthly expenses and I was able to just redeploy all that money back into buying more rentals, fixing them up, doing whatever I could to try to grow that business, starting from basically zero. I mean, I was working for maybe 40 grand a year at the regional airline I was at. This is pre-COVID and the military is paying me maybe 15 grand at the time a year to do the flying for them. So it wasn't like I was just destroying it out there. And I know that some people may listen to that and be like, oh man, you're making so much money, but in the grand scheme of things I wasn't really crushing it Right.
Speaker 0:So, living at home, if you can do it, I really would recommend, if you're younger, watching this and you're trying to get into real estate, investing living at home and buying rental properties. That's a flex, if you ask me, and honestly I'm doing this for me and for the people that are close to me, so I don't really care about the judgment. Anybody that's judging me is probably not somebody I'm taking advice from anyway, so I don't really give a shit. But the other side of that is, if you don't have parents and I was super fortunate that I had parents that allowed me to come back in my mom and stepdad they were pretty cool about letting me come and go because I was, you know, keeping a relatively low profile and not bothering them. So if you don't have that available to you, though and a lot of people don't 18 years old comes and they get kicked out or they have to move on, you know, some way somehow into life.
Speaker 0:So if you don't have that available to you, the other thing you can do is find roommates, and in flight school I did this. I had two roommates, you know three bedroom house, and it wasn't like perfect, but it was fine for what it was and we were all able to save money, and again, that was another thing that helped. So I think, if you're looking ahead and you're trying to figure out a way to kind of get yourself in position to buy rentals or to try to grow what you already have like, getting a couple roommates is not a big deal and usually it's kind of fun too. You know you have people to hang out with. You guys gotta build a whole friend group together if they're good roommates. I guess, and honestly, beyond all that, there's just always awesome stories like I have some hilarious stories from the roommates that I had in flight and I don't think I would have ever been able to get those kinds of stories without having some of the characters that I live with. So that kind of stuff to me is really powerful because at the beginning of your career you're making the least, you have the least amount of money possible to deploy into the market and so you need to make every dollar count right, like you can't waste money, you can't make bad deals, you really can't make too many mistakes at the beginning. I mean you can. It's just going to make everything take that much longer than so. I think this is a simple hack that you can do to save yourself 1015 grand a year maybe. And if you can save 1015 grand, I mean that in my market that's a duplex, that's a duplex a year basically, and starting out that's not very, you know, it's not very exciting Like, oh man, one duplex, like I want to get hundreds of units, but the way you get hundreds of units not that I've done it, but the way that I believe that you get them is by starting with one and making that first one a good deal and then progressively building from there. So that's exactly what I've done. I think it's.
Speaker 0:One of the things, though, was literally living at home. I was getting made fun of by people Anybody that was with me in my unit. If they ever see this, they know I was living at home. I was getting made fun of. I was like, at one point I was joking with people. I'm like I must be the only instructor pilot in the army that lives with their parents at home, like in their mom's basement. Basically, like I, on one hand, I'm doing something that I think is like impactful and fun and interesting, and the other hand, I'm like a, a loser in my mom's basement. But I was willing to delay satisfaction, you know, through those couple years to then execute on the other side, and I think I'm going to have a pretty interesting career from this point forward because I was willing to do that. And, again, it's not fun. It's not fun telling anybody that you live at home like any. Anybody that hears that automatically assumes that you're up to basically nothing in your life. But those are the people that are close to you and the people that you actually care about. They'll understand.
Speaker 0:I think in this environment it's important because right now inflation is so high, or has been historically high in the last couple of years. Maybe it's coming down now, but the damage is already done in some ways. Wage growth hasn't kept up with that at all, really. I mean, except for a couple of small industries, a lot of people are still getting paid, you know, with pre, you know pre COVID type money, even though the world post COVID has been totally turned upside down. And so when you're looking at that, especially as a younger person, how, what can you do to mitigate that? Well, you're not gonna be able to grow your wages very quickly because you don't have any experience and you're just starting out. So you don't have a lot of. You don't have a lot of leverage there. But you can leverage the things that you're spending money on.
Speaker 0:And I'm not a huge, I'm not a Dave Ramsey guy. You know you need to eat rice and beans and sit in a cave, but I would say, like, if you can control your housing spending or at least limit it by living at home, by living with roommates, I think that's one of the simplest hacks that you can do and you can still kind of still have the same quality of life, but you're not going to be overextending yourself, we're not going to be paycheck to paycheck trying to cover your costs, because if you are living paycheck to paycheck, then this real estate investing thing is basically impossible because you don't have enough money to buy anything. And I know there's so many people out there oh, you don't need any money down, we'll finance everything. But if you want to build something sustainable and something that actually grows and builds into something important, you're not going to be able to get there with this type of scenario. When I look at all this, that's kind of the first thing that comes to mind is as a simple place to pull out a lot of money, because for most people, their housing expenses their most expensive monthly, occurring, reoccurring bill. You know, you got Netflix, you got this, you got that. That's $10 here, $20 there and I get that. They all add up to bigger numbers down the road, but the biggest expense for most people is their housing, and so if you can eliminate that right off the top and you can focus in on educating yourself and starting to get your first couple of rentals, then I think that's the game plan that's gonna work right now.
Speaker 0:And the other side of the coin is go make more money right, but it's not that simple. If everybody could just go make more money, they would make more money, right. So it's not that simple. But that is the other side of the equation is. Okay, if you don't want to limit your expenses, then you need to increase the rate that you're shoveling in money, and so to do that, you're going to need to either be in a niche that pays a lot of money, or get experience, or offer something that other people can't provide, or that somebody sees in you that they're willing to invest that kind of money, and so that's something that is totally dependent on what industry and or what you're doing, and I'm not really going to touch on that. But that is the other side of the equation. Make more money or reduce the money that you're spending those are like kind of the two choices. It's pretty simple. It's a kind of a binary thing. So those are my thoughts right now.
Speaker 0:That's just a side note to kind of get myself ahead, and that was one of the things I did. It was really boring, really kind of not cool, but it works, and I think that if it works and it's not broken, then don't fix it, and so I think I would pass that advice off to as many people as possible that are starting out. If you're in your forties and you're watching this, obviously it's probably not applicable. You could still get roommates, you know it's still a possibility, but living with your parents probably not possible. But, honestly, anybody that really wants to get into it and is really dedicated to trying to build a portfolio, nothing should be off the table for you, because you should just be trying to do anything possible to grow and make smart deals, especially starting out.
Speaker 0:You know, those first five deals is what I always tell people is like the first five deals are what really matters, because if you jack up your first five deals, everything else is going to take you so much longer that you're just going to eventually either give up or you're going to be in a situation where you just don't see the light at the end of the tunnel and you just kind of fizzle out and you get a couple of duplexes and you ride into the sunset. There's nothing wrong with that. But I'm specifically talking to people who want to build a large portfolio. Nothing should be off the table. You should be willing to do basically anything to get it done. That may be working extra, that may mean living with your parents, that may mean not going out three days a week and maybe maybe you only go out once a week.
Speaker 0:You know there's a lot of things that you can do to try to move the needle in the right direction. You just have to be willing to do it and actually do it. I mean, that's literally what it comes down to is like actually doing these things. Talking about them, watching on YouTube all that stuff is great, but if you don't actually do anything, then nothing will change and no one's really going to come to save you. You know there's nobody coming to the rescue for anybody. That's not actually doing anything out there, because in this world it just keeps moving. So either you're going to do something and make it happen for yourself or nothing's going to happen and nobody's going to care.
Speaker 0:So, on that uplifting note, I hope everybody has a good day If you're watching this, still, I appreciate it. Leave a comment. I think I got one, maybe two comments now. One of them was one of my friends, though so it doesn't really count, but any other comments or whatever, I really appreciate it and we'll make some more videos and keep talking about what's working and what's not, and try to help people build portfolios. So we'll see you.