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 Own $5M In Real Estate... But I Still Rent
Challenging conventional wisdom, I take you through my controversial but pragmatic approach to real estate. Despite owning millions in rental properties, I've made the strategic choice to rent my own home—and there's solid financial logic behind this decision.
The current real estate market presents a perfect storm of challenges: sky-high interest rates, inflated property values, and diminishing affordability. For $2,000 a month in Milwaukee, my rental provides flexibility that would require significant sacrifice or capital to match as a homeowner. Rather than sinking funds into an overpriced primary residence, I'm deploying that capital where it generates better returns—in my investment portfolio.
This approach offers something invaluable that never appears in traditional investment calculations: peace of mind. Financial mobility means having resources available when opportunities arise or emergencies strike. Physical mobility means I'm not anchored to a property that might take months to sell if life circumstances change. Together, these freedoms provide a security that overextended homeowners simply don't have.
Society constantly pushes the narrative that homeownership equals success—that taking on massive mortgage debt somehow represents achievement. I've bought and sold houses before, so I'm not anti-homeownership, but I refuse to participate in what feels like financial theater. A house that drains your finances is more liability than asset, regardless of what conventional wisdom suggests.
For those starting their real estate journey, consider whether pouring everything into your primary residence truly serves your long-term goals. Sometimes patience is the most powerful investment strategy. Don't let Instagram-driven pressure push you into decisions that limit your financial freedom for decades to come. What housing choices have you made that went against conventional wisdom but served you well?
What's up everybody. My name is Cole. I'm a part-time real estate investor, a full-time airline pilot and a part-time military instructor pilot. Today I'm talking about how I own multiple millions of dollars worth of real estate, yet I still rent my very own place. I don't own it, I'm renting right now. I've owned houses, I've sold them and I'm currently renting. And why do I choose to do that when I have rental properties? I'll tell you right now.
Speaker 1:I think right now is an incredibly expensive time to buy a house and a very uncertain time too. I think there's the aspect of the current interest rates and where things are going, but then there's also the aspect of what does the future hold? Where are we going with all this? And to me right now, affordability is extremely low. So you have the uncertainty aspect combined with the unaffordability of houses. The cost of things relative to what you're getting, I think, is extremely lopsided, and for me, to buy something for the same price that I'm paying for this apartment $2,000 a month in Milwaukee you're not going to get a whole lot, not at seven and a half percent interest, not with the property taxes the way they are. So then it's okay, I'm going to have to pay down a larger purchase price to meet the same rough monthly cost. And when I look at that I'm like, okay, I'm gonna go tie up $100,000 or $150,000 or $50,000 to buy a house that I don't necessarily really want, but I just want to be able to say I have a house To me. That makes no sense. So I'd rather go take that money, deploy it into the market with the rentals and then come back when the coast is clear, because I'm not buying rentals that are in the same price range as what I would be buying for a single family residence for myself. So I don't really think that the two necessarily correlate. So I'm taking that money, I'm deploying it into the market and what I'm doing is just sitting on my hands. Sitting on my hands for maybe 12 months, 16 months, 18 months, something like that. See what it looks like from there.
Speaker 1:And a lot of people are gonna say, oh, it's just gonna be more expensive. You should have bought now. The best day to buy was yesterday. But I'm okay. I'm okay with taking that risk. I don't really care.
Speaker 1:I think that there's eventually going to be something that has to break to make this all more affordable for the average buyer like myself and I'm not going to overextend myself like a lot of people do, just to post on Instagram and say I bought a house, look at me, like, look, how amazing I am, I got a loan basically is what people are saying and they pat themselves on the back and they are so excited for that. And I'm not saying that you shouldn't be excited to buy a house, but if you're getting over leveraged and you're pushing yourself to the very edge just so you can have a quote, unquote nice house and show everybody on Instagram that you made it, then you're fighting a losing battle and I'll just I'm going to weigh that out so that way I can get something I actually want and I won't have to leverage myself to the maximum to try to pull that off. So when I'm looking at that's one of the lenses I'm looking at this through Another lens I look at this all through is mobility and ease of movement. If I have a house, it's obviously very hard to just sell a house overnight. They're not very liquid. Even if you find a cash buyer, you're looking at a couple weeks to close, but in most cases you're gonna be waiting for the entire transaction to play out with a normal traditional loan and get an appraisal and a home inspection and all these things, and that's usually about 45 days.
Speaker 1:So you're not very mobile as far as selling the house and moving, and for me that's a priority right now. I don't know that I'm going to or that I need to, but I would like the option to right now and having a lease. It gives me the ability to move or maybe adjust to changes in my life without having to be like oh man, like now I'm upside down on this house but I have to sell it because I need to move somewhere else or I need to make an adjustment somehow. So this gives me a lot more flexibility and at the same time, I think that saving that down payment money and using it to either invest with or just have for a rainy day is another sense of mobility. I have the financial mobility too now. Not only do I have a lease that I can break or I can get out of in the military's case, I can get out of the lease, let's say they put me on order somewhere but on the other side of it I have the financial mobility. So now I have money in the bank that I can use for whatever, but I'm not worried about. Oh man, I just got this house, I spent every penny I had and now if anything goes wrong in my life, I get laid off, I get injured, something happens to the house, I crash my car I have no money to deploy to fix those things.
Speaker 1:So I think there's something to be said for the peace of mind aspect and that's never captured in anybody's math. When they do ROI return on investment mathematics it's not captured in that. The peace of mind factor is something that really matters, but I don't think that it's captured often. That's another thing. That kind of plays into it for me. And this isn't all.
Speaker 1:To say that I'm anti-homeownership I don't think that's the case. I just I'm not so focused on the homeownership thing. To say that I'm a homeowner and to tell everybody and to be like all, to feel like I achieved the American dream, I feel like it's a farce and I'm not going to overextend myself to try to check that box. I've already done it before. I've bought and sold houses. It doesn't really do a whole lot for me at this point, especially because of what I want is outside of realistic possibility right now. Could is outside of realistic possibility right now. Could I leverage myself and do something crazy to pull it off? Of course everybody can do that and everybody does do that in America but I'm not planning on doing that. It's not worth it to me, I don't care enough to do that. So I know the option is available to me, but I'm choosing not to do that, and I think that's something really powerful.
Speaker 1:There's a lot of people that don't have that fortitude to actually hold back when they have some of that available to them. They're just going to go for it, and I think that hurts people a lot in the long run, especially when you look at what you're paying on interest on a house in the long term. People are talking about how much equity they have and this is their biggest asset and whatnot. I look at your house as like your biggest liability, like it literally generally costs you the most out of all the things that you pay for. With post-tax dollars, it's probably the biggest expense for most people. So when you look at it through that lens, it's like really hard to justify that this is your biggest asset when it literally costs you the most amount of money, and the compounded interest that you're paying over time is an incredible amount.
Speaker 1:That's not to say that homeownership is bad. That's just to say that you should probably not leverage yourself to the maximum to pull it off. And so that's where I'm at. I've got literally millions of dollars worth of real estate and I'm renting, and that's all. I don't care. That's totally cool with me.
Speaker 1:I'm not saying that's the right choice for everybody, but it is a choice that you can make and for those of you who are younger, looking at getting into real estate, especially specifically rental properties, and owning them long term, it's not a bad idea and it's something that I would probably recommend to a lot of people. Again, it depends on your situation. It's case by case basis, not one size fits all, but it's a really powerful thing, I think. Especially if you get roommates, you start doing that house hacking type thing. But with a rental you're saving money in a whole bunch of different directions and you can use that to help get yourself kick-started, to start your career out, and the sooner you get started obviously, just like any other investment is generally the better. That's kind of my thoughts today.
Speaker 1:I was just thinking about it. I don't know why. I just felt right to talk about it and that's what I'm doing right now, just going with what feels right in the old heart. Yeah, that's why I don't own my own home right now and if I do in the future, I'll definitely talk and break down the expenses and costs and what I'm making to justify that purchase price. But for now I'm renting. Don't let society pressure you into doing something that's really dumb for you long term is my advice probably to somebody if they ask me. But if you have any anecdotes to add to this, definitely welcome to throw them in the comments. I still am like one legit mid comment outside of some spam stuff, so I'm eager to get one more comment to respond to. I could probably make a video in response to it. That'd be cool. So if anybody's watching this, appreciate it if you made it this long and we'll talk to you soon, see ya.