Tailwind Talks

Building a $5.5 Million Portfolio While Working Full-Time as a Pilot (Tailwind Talks 001)

• Cole Baltz • Season 1 • Episode 1

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Ever wonder how to build substantial real estate wealth while keeping your day job? Meet Cole, a full-time airline pilot, part-time military helicopter pilot, and real estate investor who's built a $5.5 million portfolio spanning 63 units—all without quitting his aviation career.

Cole's journey began humbly washing dishes as a teenager, using minimum wage earnings to fund his passion for flying. His first real estate purchase was a modest $100,000 HUD foreclosure bought with just $3,000 down. That single property became the foundation for his multi-million dollar portfolio. Unlike many real estate personalities advocating for immediate large-scale investments, Cole shares a refreshingly practical approach focused on gradual growth and strategic positioning.

One of his key insights is the critical importance of your first few deals. While experienced investors can weather unexpected expenses, newcomers need particular caution to avoid burnout. Cole also reveals practical hacks like obtaining a real estate license to earn commissions on purchases and save when selling. For busy professionals juggling careers with real estate aspirations, his time-efficient approach to property analysis—completing evaluations in under 20 minutes by focusing only on fundamental value drivers—provides a realistic framework for success.

What makes Cole's perspective valuable is his commitment to authenticity over hype. He's building a community for real operators rather than selling courses or promoting get-rich-quick schemes. Whether you're contemplating your first property purchase or looking to scale while maintaining your career, his journey demonstrates how disciplined investing and patient positioning can transform modest beginnings into significant wealth. Ready to see how your first $100,000 property might change everything? Join Cole as he documents his continuing real estate journey.

Speaker 1:

Hey, my name is Cole. I'm a part-time real estate investor in Milwaukee, wisconsin. I'm a full-time legacy airline pilot and a part-time helicopter pilot, so I'm juggling a lot of things. But this is my attempt at trying to talk about real estate in kind of a way that maybe would be beneficial to people that are just getting their foot in the door, looking at real estate from the outside and saying, man, I would love to get into that, but I don. I started as a dishwasher at the open hearth and worked my way from there. So we built into 63 units. I've got partners. I'm the majority partner but we've got some minority partners. It's about 5.5 million or so, plus or minus a little bit, for total asset value Not the biggest portfolio out there by far but I'm trying to get ahead of it and say, document where I've been and then catch up to present day and then go from there with what we're doing today. Just this morning I toured a single family house with my buddy and stuff like that I think would be awesome to talk about to somebody who might be looking at the real estate market, saying I'd love to get into that or find a way to get my foot in the door. This is hopefully going to bring a lot of value to those people and for absolutely zero dollars. So we'll see what happens.

Speaker 1:

So, basically, background started as a dishwasher at a place called the Open Hearth. It was a lovely restaurant. I never actually ate their food, but I worked there as a dishwasher for about a year, 14 to 15. And then 15, I upgraded and I got picked up at Five Guys Burgers and Fries, flipped burgers there and hung out there for a while. Awesome people I met some awesome characters out there, really had a blast considering what it was, and then I moved on from there. But during that period of time, while I was in high school, I was using that money to pay for flight lessons. So it was costing me, I think, maybe $130, $140 an hour for one hour of flight training and in return I was giving them all my hard-earned dollars at Five Guys or previous to that, the open hearth, and I was making $7.25 an hour or whatever. From that point forward got to near the end of high school and I was like man, I want to fly, I love flying, it's awesome, but it is freaking expensive. So I was like I need to figure out a way to offload that cost and move it somewhere else. And I moved that onto the shoulders of the military somewhere else. And I moved that onto the shoulders of the military. Uncle Sam was looking for some pilots and it just so happened that I was looking to be a pilot. So we found an agreement there and they sent me off to flight school.

Speaker 1:

I had about a year wait after high school to actually make it to flight school, so I graduated slightly early, like about a semester early from high school, and I ended up working at the post office. So I was slinging mail in the inner city of Milwaukee, getting harassed by people and just having a blast. So I was slinging mail in the inner city of Milwaukee, getting harassed by people and just having a blast. So I was delivering mail until I went to flight school. Go to flight school, graduate flight school, come home and that's my first taste of getting my foot in the door with the real estate stuff.

Speaker 1:

I had gotten my real estate license to operate as a realtor in Wisconsin but I have to tell you I absolutely hate sales. So I am not the realtor that you would want. It has that same used car salesman vibe to me and I just really hate that. So I do it for friends and family and primarily for myself. Fun fact, kind of a hack for some of you who are looking at trying to get into investment properties get your real estate license and if you buy your own property you get paid a commission and vice versa, if you go to sell a property you can do it for $0 commission. So if you're trying to save some money and make a deal just a little bit sweeter, that's one way to do it. It's only a couple percent, two, three, four percent, but two, three, four percent does add up, especially when you're starting out and you don't have a lot. So that's something I always suggest to people because it costs money and you have to take a test and you have to study and everything. But if that's going to be the barrier that stops you from getting into real estate, then you're probably not a good fit for it anyways, because there's going to be a lot more kicks in the teeth than taking a test and trying to study for it if you really want to dive into the rental property world.

Speaker 1:

So first, property as a HUD home foreclosure online I think it's called like hudhomestoreorg or something like that. It's government foreclosures basically, and what a government foreclosure is, at least in the case of this house, was a FHA loan that somebody defaulted on and then the government ended up with it back in their hands. So FHA loans are kind of government-backed loans, whatever. And I went and toured this house and it was a little scary because I'd never really been in like a really beat-up house like that. But I kind of took some people that I trusted with me one of my friends' dads and him, and then my parents. Some people had good feedback, some people didn't, and I decided to roll the dice. So the initial property was $100,000, single family three bed, one and a half bath, put $3,000 down. I was a first time home buyer and got all the credits and all this stuff. So this is 2017. And then, rolling forward from there, that single family was the catalyst for everything. It's a hundred thousand dollar house, basically nothing, but it rolled into five plus million dollars and a lot more coming down the pipeline here of real estate. And it all started with that one house.

Speaker 1:

So if I was to say anything to anybody is it may seem like a small deal. Your first deal is like man, this is nothing. There's such bigger players out there but it's. It really could be the difference of me doing everything or doing nothing. So take it seriously and I always tell people like your first five deals, that's where your money is truly made, because I can weather and people bigger than me, way bigger than me, can weather the storm of a bad deal. Right, you get a bad duplex, for example, I bought and it was like $40,000 I was not expecting to spend and we were able to weather that storm. But if this is your first deal and you get hit with that bill, that could be the thing that puts a bad taste in your mouth for real estate and also kind of ends your career before it even began. So just think about that and say, hey, you know what I'm going to, maybe I'll pass on a couple of deals. I really want to find basically the perfect deal or as close to perfect as reasonably you can get. So something to think about.

Speaker 1:

I just saw a video Grant Cardone put out where he's I wouldn't even start with a single family, I'd start with a hundred units. You know I'm going to go. You know go big and 10, x and this and that, and it's like man, if you're, if you're the average person listening to this, I'm from a. You know I'm from the Midwest, like if you're an average Midwestern, you know you don't worry about the money, just find the deal. You find the deal Like you don't know anybody that has any money either. So it's like what do you do? So I'm going to try to totally flip that on its head and I'm going totally practical things you can do to try to save money, try to make money, try to get your first property, and then we'll just kind of go from there, preach about what I haven't done. So hopefully that will bring some value to those of you who end up watching this video and the future videos to come. And if you're just listening to audio, I'm going to try to do my best to kind of make them coalesce and not really do too much for the visuals. That way the audio listeners aren't losing out on too much. But if I end up doing one or the other, please let me know. And same with the video. I'm not a videographer or a photographer. So if you see something that's egregious, please help me and I'll help you by you helping me, I guess, and making better videos.

Speaker 1:

I'm going to talk a lot about trying to manage real estate, whether that means buying, selling, actually managing the properties, whatever it may be, and doing a full-time job. My full-time career at the airlines and flying for the military takes up a lot of time. Sometimes it kind of ebbs and flows. I've had a couple of days here where I didn't have a lot going on, but then some weeks I'm like every day I'm either flying in the jet or I'm in the helicopter and that takes a lot of my brain power. So it's like how can you continue to build a portfolio but also keep your job? Because a lot of people the answer they want to hear is, oh, just quit your job and just go all in on real estate and hey, that works for a percentage of the population, but it's not a cure-all for everybody. And in my case, for me to leave where I'm at now is really challenging and it's something I think about a lot, but it's just not quite where it needs to be to be able to really consider that.

Speaker 1:

But even back when I was making no money, I mean, I was flying for a regional airline and we're getting paid like $30 per flight hour as a first officer and like that sounds like a lot 30 bucks an hour, especially in 2018, 19 timeframe but at the airlines you're only getting paid for the hours you fly on an average trip. You're not flying 24 hours a day. You're not even flying six hours a day, maybe. So it was a really, really challenging time, but I was finding ways to make it work. And even back then, when I didn't have money, I got that first house. It took me almost two years to actually fix it up and make it nice and then I rolled that money that I had maybe 50 grand with another 20 grand from a friend of mine that I took on as a partner and he rolled the dice on me and we bought an eight unit and then we ended up selling that eight unit down the road and, clear to check, that was almost 300 grand.

Speaker 1:

So just because you're not making a lot of money doesn't mean you don't have the ability to go and enforce that equity somewhere within the market and find an arbitrage somewhere, because they're everywhere. You just have to either have the knowledge to know how to find them and or spend enough time in the market that eventually, something just falls in your lap, which it does happen like that sometimes, but a lot of it has to do with putting yourself in the position. The reason I got that deal is because I got my real estate license back when I was just graduating high school. I was saving up money working at the post office slinging mail, and I was flying helicopters at night because I didn't have enough hours to go get a real flying job. So I was doing that kind of stuff to put myself in the position for that opportunity. But those things didn't make the opportunity happen, if that makes sense. I just was available and ready when it did come. So that's the one thing that you can do is try to put yourself in the best position to win when that time comes. It's not going to be maybe tomorrow, it may not even be six months from now, but if you don't have all your ducks in a row when that opportunity comes and you have to pass on it, it hurts down the road when you see what that could have been and you're just on the sidelines just watching.

Speaker 1:

Is real deals? People talk all these hypothetical numbers and a lot of people are using things that I really don't think are important into looking into deals and people are overanalyzing deals. They're showing people how to do all this paralysis by analysis, type, deal making and to me, I can get in and out of a property in probably five minutes and have a pretty good idea of exactly what I need plus or minus a couple thousand dollars maybe and I know what the market value is. I can do all this stuff. I can do an analysis on a property in 15, 20 minutes easily and I think that those skills it's not even a skill really, it's just knowing how to look past the BS and not get hung up on it and just look at the things that really matter. So I'm going to be doing a lot of shorts and a lot of TikToks, probably of those kind of deal day by day deals. But I do plan on doing some longer form content of stuff that I've bought and what I saw on those properties and how it played out wins and losses. I've had some losses for sure, and I'm going to do the same thing with deals that I'm looking at.

Speaker 1:

Today, like literally today, I went and looked at a deal at 930 this morning with my buddy. They wanted, I think they wanted 80. I offered 70. They came back at 76 and I ended up offering 74. So we'll see if I get it, but that deal would be an interesting one to talk about and I think that people that haven't bought a deal would find some value in that.

Speaker 1:

I hope to bring on guests at some point too. I don't want to do it until I have an established audience and people that actually want to see that, because I know for a long time I'm probably looking at years of single digit views on these videos and I understand that's just the name of the game and I may not even be providing that great of content. I'm going to reserve the guests until I have something established and I prove to myself that I can stick to this, because otherwise I think you're putting the cart before the horse, and I'm a big one of my big things is not doing that. So I really try not to, and I'm in that case. I'm just going to wait for now, but we have a lot of content that we can talk about just myself. So that's the plan. I'm really looking forward to it. That's generally.

Speaker 1:

The idea is basically just bringing what's real, what's going on, and trying to bring value to people that are either looking at real estate as an option, are currently in the market and building some sort of community around that I'd love to really bring together like real operators.

Speaker 1:

I don't really want to be involved with the course selling and the gurus and the this and the that, like, I'm just going to be real. Some of it's going to be good content that some of it's probably going to be bad, but I'm just going to give you what's going on for me, for real, and we're going to build a community from there. That's the plan. Really appreciate anybody that's taking the time to watch this and put themselves through the agony of listening to this. Right now, I've got a lot of learning to do, especially on the YouTube side. The last YouTube video I ever uploaded was like 2012. So I'm way out of the loop right now. I'm an old, 29 year old, so forgive me, but if you have any feedback of any kind, you have any interest in leaving a comment, please, please, leave a comment and I will totally get back to you. We'll talk in the comments and then we'll go from there. Really appreciate everything that.