Turn your first short-term rental into income, then turn it into a portfolio
Learn from a former detective who stopped trading his life for a paycheck and built his way to real freedom
Everything I have today, I built while being there for my wife and four kids, all while living real life. A lot of the people teaching this caught a couple of good, lucky years and started selling a course. What I teach in this course I've lived and proven myself, and I've helped hundreds of others prove it, too.
I own my portfolio, and I still run it today.
I built The STR Operator Circle to give people a real path to their first property, or their next five. The real process, the real numbers, with someone in your corner who's done it and will tell you the truth.
About Kyle
I'm Kyle. I spent more than ten years in law enforcement, most of it as a detective. These days I buy and run short-term rentals. I coach other people through this business, from someone buying their very first property to operators scaling their existing portfolio.
If you're going to trust me with something this big, you should know who you're actually dealing with, so here's my story.
What The STR Operator Circle actually is
The STR Operator Circle is a course and a community for people who are serious about short-term rentals. Some of our members are buying their very first property; others already own a few and want to run them better or scale up. Either way, you're in a room full of people doing the exact thing you're doing, learning from each other, experts I bring in, and me.
I built it to be A to Z. Everything from how to pick a market and underwrite a deal, all the way through launching it, running it, and keeping it from turning into a second job. There’s none of the "one property, and you're free" nonsense you hear everywhere else.
There are two ways to join, depending on how involved you want me to be.
TIER ONE
Course + Community
Everything you need to buy and run your first short-term rental the right way, plus a community you get to stay in.
The course
The full course walks you through the entire process, start to finish. It's pre-recorded so you can go at your own pace and come back to any piece of it whenever you need to. It covers:
- Market research: How to find and analyze a market, including exactly how I use AirDNA to figure out where the money actually is.
- Underwriting: How to run a deal through my own spreadsheets and market-discovery tools, so you can tell a good deal from a bad one before you ever put money down.
- Pricing: How to set your rates and keep them working for you as demand shifts.
- Listing optimization: Learn to make your listing stand out and get booked when ten other places are competing with you.
- Guest communication: The messaging templates and systems that keep guests happy without you glued to your phone.
- Management and automation: How to get a property running mostly on its own once it's set up right, so it doesn't take over your life.
- Interior design and setup: How to design and set up a place that actually gets booked, what works and what doesn't, so you can do it yourself or know exactly what to hand off.
- Tax strategy: Get the big-picture on how short-term rentals are taxed and where the advantages actually apply to your situation.
- The STR tax loophole and cost segregation: Understand how the "short-term rental loophole" lets you use losses against your income, and how a cost segregation study creates those losses in the first place.
- Lending: Know your financing options going in, so you walk into a lender conversation on your terms instead of taking whatever you're offered.
- Legal and structure: Understand the legal and entity side, so you can set it up right from the start and know what you need before you talk to an attorney.
To be clear on what this is: The course teaches you to do all of this yourself, so you can make smart calls on your own property. It's not a done-for-you service.
The community
This is a living, active community of people who are actually doing this, first-timers and experienced operators in the same room, trading what's working, asking questions, and posting their real wins and numbers. When you're figuring out your first deal, there's real value in being surrounded by people a few steps ahead of you.
The live calls
I run live calls throughout the week:
- Deal Breakdown calls, where we break down actual deals members are looking at.
- Listing Review calls, where we tune up listings and pricing.
- Automation calls, where we get your systems running so the property doesn't run your life.
- Expert calls, where I bring in people most beginners never get access to. A short-term-rental designer, my lender, who breaks down financing and where the market's heading, and a real estate attorney, with more experts to come. They host monthly calls to teach you real, usable stuff, and that teaching is what's included. If you want to hire any of them for the actual work later, that's separate and up to you; by then you'll know exactly what to ask for.
Everything is recorded. If you can't make a call live, you get the replay to watch whenever you want. And when you join, you don't just get the calls going forward. You get access to the whole library of past calls too, so there's already a mountain of material waiting for you on day one, and it only grows from there.
One important note: an AirDNA subscription is required, and it's not included in the program. It's a core part of how we work; I lean on it heavily in the group calls and one-on-ones to break down markets and deals with you. You'll also use it for your own research and underwriting between sessions.
It's evergreen
Your access doesn't expire. You keep the calls, the experts, the whole library, and everything I add later comes with it at no extra cost. This business changes. Pricing shifts, the market moves, and new strategies come up. So, a year from now, when you want another set of eyes on your listing, you hop on a group call, and we go through it together.
TIER TWO
Course + Community + One-on-One With Me
Everything in Tier One, plus direct one-on-one access to me for six months. This is for people who are ready to move now and want me personally in their corner while they do it.
How the one-on-one works
We start with an in-depth onboarding session, about an hour, just you and me. We go through everything. Where you're at right now, your immediate next steps, the homework I'm putting in front of you, and the bigger picture. By the end of it, we've mapped out your full six months, so you know exactly what you're working toward and what you need to do to get there.
From there, you can schedule a 30-minute one-on-one call with me once a week if you need it. Some weeks you'll want to jump on and work through something. Other times you'll just be getting things going on your own. It's there when you need it.
I want to be straight with you. I'm not going to find your deal for you or hand you a property. What I do is give you the tools, the framework, and the roadmap. I then review your work and steer you as you go. You bring the effort, you do the homework, and you execute. I'll make sure you're doing it right and not walking into a bad deal. I teach you the skills to do this right so you can apply them to your next one when you feel it’s time to grow.
Why it’s worth it
Tier One teaches you everything it takes to find, launch, and run your first short-term rental the right way. The course, community, group calls, and the expert calls give you the full playbook and the room to ask questions as you go. Bring a deal or your property to a group call, and I'll work through it with you right there. People close good deals and fix real problems.
Tier Two puts me at your fingertips between the calls. For six months, you have direct access to me, so when something comes up and you need an answer before the next group call, you can reach me.
It also goes deeper into your specific property. On a group call, I'll pull your place up and give you real answers in the time we've got. One-on-one is where we get into the details that don't fit a group setting: the specific quirks of your property, the day-to-day of running it, and the small tweaks that keep it from turning into a second job.
Hosting doesn't run on business hours. A guest problem at 9 PM doesn't wait for the next group call, and neither do the judgment calls that decide how your first year goes. One-on-one is having someone who's done this hundreds of times reachable when you're in it, so you're never stuck guessing on the stuff that actually costs you.
The launch guarantee
The weekly one-on-one access runs through your six months. But the guarantee is separate from that timeline:
When you're ready to launch, I will personally sit down with you and launch that first property. We will go through the whole thing together: the listing, the algorithm, the pricing, and the automation, until your property is live on Airbnb and running right.
And "when you're ready" means when you're ready. If you've done the work and you're launching eight months in, or even a year in, I'm still there for it. The one-on-one coaching window has a start and an end. Me showing up to launch your first property with you does not.
Who this is for, and who it isn't
I do not want anyone to waste their time or money.
This is for people who are ready to put in real work. Once a property is set up and automated correctly, it gets close to passive. Getting it there does not, and anyone who tells you otherwise is selling you something. If you're not willing to get a little uncomfortable and do the work up front, I'm not your guy.
You also need real capital to do this. Plan on at least $100,000 for your first property, between the down payment and getting it set up right.
If you're not there yet, the one-on-one side of things won't be worth your money. But the course and community are a great place to start. Learn it now so that when you do have the capital, you already know exactly what to do with it.
This is not arbitrage. I don't teach it; I don't believe in it for beginners, and it's not what this community is about. If you're here to lease someone else's place and flip it on Airbnb, this isn't the room for you.
