Real Estate Market Too Hot? Go South…Way South | 2021

May 28, 2021

In this crazy hot market, where can an investor still find cash-flowing assets?

Not many, especially when you’re alone. Real Estate Podcaster, Tyler Sheff has his eye on a national icon, Key West, Florida. His 20 years of experience in real estate management and investing have discovered tremendous opportunity, but at a high entry cost.
The good news?
Accredited investors around the country will be leveraging Tyler and Mike’s team, pooling their resources to sharing all of this pirate island’s bounty. More videos to come as Tyler shares how he sees an opportunity when other’s look the other way.
Interested in picking Tyler and Mike’s brains for your own advantage? Book a call with us at:


Hey, I’ve been in your shoes and I love sharing stories of my journey and how I got money working for me. I’ll show you how too!


My goal is to experience with you, what’s on the outside. By sharing what we learn, we can all do our part to keep doing what we love, flying, without the threat of loss of income.

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Pilots make excellent money and we love what we do. We are used to being in command and control in the flight deck. But it’s our financial future, managing cash flow, wealth, and passive income that can often seem OUT of our control. It can be a risky gamble to put your money into retirement funds and the stock market. No one gets held accountable if there are significant losses. And so it feels like you run out of options. 

After entering the world of Real Estate Investing, I’ve found a path to security, passive income, and feel in control again. 

Real estate investment stands on the solid foundation of homes and buildings, which is in high need. We have control of the tenants we have, screening them for reliability and long-term viability. We can take measures if someone isnt working out. We create the system and safeguards for our investment, and all the income comes straight to us. Our return on investment (ROI) is high and steady.

As a pilot and real estate investor I am passionate about helping other aviation professionals fly towards financial freedom through investing in multi-family properties. Let me show you how to put your money to work for you. 

Do you want to see your money multiply, creating financial freedom for your future? Are you interested in increasing your income through passive means? If so, book a briefing with me, and let’s talk.  


– Guess what? After you watch the next six minutes of this video, you’re gonna have questions about one of the last few places in America where you could still buy cash flowing assets. That’s right, the land of Jimmy Buffet, Key West, Florida. Now, in the next six minutes, you’re gonna learn a little bit about what Tyler’s thinking, and how he can profit. And if you’re like me, and you’re curious, you wanna pick his brain, see how he does it, schedule a call with us at All right, pilot investors. So we’re down here in Key West with the host of “The Cash Flow Guys” podcast, Tyler Sheff, with over 20 years of real estate investing experience. So as I’ve been teasing you the past few weeks, here he is. So we’re setting up a fund so pilot investors who are accredited can join in Tyler’s expertise down in Key West as he takes his expertise and experience to utilize opportunities that most do not see. Key West is a pretty expensive place, isn’t it, Tyler?

– I’d say.

– Yeah.

Expensive is really a state of mind, right? What does that mean, expensive?

– Exactly. So without putting my money into the fund, it’d be really hard for me, Tyler and I to get into Key West. But if we pool our money into this fund with accredited investors, now we can work some magic with his expertise. So Tyler, can you talk about what opportunities you see right now?

– Yeah, and I’ll start with that. I thought the same thing for many years, expensive. What does that mean, what does expensive mean? Yeah, a house here in Key West starts at probably 600 on the very low side, and the average selling price is between 800 and a million dollars. So is that expensive? Well, I ask you differently. When you pool a group of people together and you can buy an asset, whether it’s cash flowing or it’s a single family home that you’re gonna fix up and repair, you’re gonna invest some money into it to increase the equity, it’s not expensive if it’s within your purview, right? Things are only expensive if they’re outside of our reach. People buy apartment buildings all the time. People get together, they buy 100 unit apartment buildings. Mike, I don’t think you have probably enough money in your checking account to write me a check for a 100 unit apartment building, do you?

– Definitely not here.

– But I bet if you and I and 20 of our friends got together, we could probably buy a five, $10 million building, and put that in our portfolio, and then share the asset, or share the equity in that property, but more importantly, we share the cash flow. I mean, there’s a reason why I call myself the cash flow guy, right? It’s about predictable streams of income over time. What does that mean? That means that someday, those of you that are pilots, you can step out of the cockpit for a minute, join us on the beach right behind me, just kind of chill out and have a good time, and more importantly, not worry where your money’s coming from. That’s why Mike and I got together, because him having the experience of working with pilots, and also his experiences owning real estate, and investing in the circles and taking the time to educate himself impressed me. Mike’s the kind of guy that makes happen, right? Actually, he holds me accountable, and thank you for that, because Mike’s not the kinda guy you wanna hang around with if you’re that person that doesn’t perform. If you say you’re gonna do one thing and then don’t do it, I wouldn’t waste your time talking to this guy, ’cause he makes things happen. Fortunately, I have that same feeling. I’m not the guy that stands around and thinks about what might happen, I go out and do it. So Key West, what does that mean? It means cash flow opportunities. Well, let’s boil that down a little bit. Yes, duplexes here sometimes cost hundreds of thousands of dollars. Here’s the thing, a lot of them are under market rent. A lot of the properties are falling apart, they have deferred maintenance, and more people than just the people that work here want to come to Key West and live. For example, I’m renting a place right now. I have a one-bedroom, and I’m paying $2,200 a month for a one-bedroom. You move into Chicago, how much is a one-bedroom, five, six, 700? Indiana, that type of place. So it’s a different market. Is it expensive? Perhaps if that’s your mindset, but at the end of the day, if you’re owning a one-bedroom place that takes down 10, or you own a couple of one-bedrooms together and in one building that brings in $50,000 a month in cash flow, is it still expensive? I don’t think so.

– [Michael] No.

– And far as the rehab thing goes, one little thing I’ve learned about down here is that people get a little complacent. When you’re in paradise, you get complacent, and what I see is the people that are buying property down here are predominantly local. There’s a lot of local purchases and sales happening, which tells me that the rest of the world doesn’t know enough about Key West, or it doesn’t know these opportunities exist. These things get sold before they even hit the MLS. So how are we doing that? Well, marketing is the answer. We’re direct marketing to sellers, and we’re making friends and building relationships with the realtors, the movers, and shakers in Key West, the people that predate me for decades and have been here for a long time. And these are the people that have their finger on the pulse, they control the market. How are we successful? How do we get contractors, right? We’re in the middle of the COVID crisis. People have run for the hills. The worldwide unemployment, massive poverty, there’s all kinds of crazy things going on, and those of you that invest in the stock market, in Bitcoin, you’re seeing things like Elon Musk has a bad day and you lose 50% of your retirement plan. It’s crazy. A lot of weird stuff going on. How do we insulate ourselves? Team. What I’ve done for the last year since I’ve been here in the Keys, I’ve spent a lot of time talking to people, shaking hands, interviewing people. I’m trying to figure out who are the best people in the business? I may be really good at what I do as a real estate agent, but I’m only as good as the people that help me get the thing over the finish line. I’ve been working with the same title company for a decade. When I came to Key West, I could make friends with new title companies, but when you already have an existing decade-long relationship for the company that rocks the house, and consistently allows me to succeed in what I do, guess what I did? I brought him on the team, introduced him to Mike, brought him on the team, had a good conversation with him. Matter of fact, we were talking to Kevin yesterday. Those of you that are coming to the summit in July, Kevin is committed to be there, he’ll be there. He can answer all your title questions. I don’t have all the answers. Mike, I don’t think you have all the answers.

– No.

– But with our team together, we’re hiring the best of the best, circling our wagons and making sure that we can produce the answers that are gonna produce results. And that’s how we’re gonna do this, and we’d like to talk to you and see if this is something that makes sense to you.

– Fantastic. Everybody knows, it’s no secret, Key West is a moneymaker, but it’s a high cost of entry. That’s why we all wanna pool our finances, pool Tyler’s experience, and the experience of our team members. So we’re gonna be announcing at First Flight Brewery over here in Key West. We’re gonna try and get everyone down so we can introduce you to our team, and open up Tyler’s mind so you can understand what opportunities he sees, both to learn, and if you’re interested in making money off of it, come on down.

– See you soon, guys.