So you want to buy your first short-term rental?

Everything you need to know about The STR Operator Circle

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I'm Kyle

Former detective, now a full-time short-term rental investor, and I coach people through buying and running their first one.

I've personally coached over 200 people and launched more than 100 properties across 30 states and three countries. I run my own portfolio of five properties doing over a million a year in gross revenue.

I put this together so you know exactly what you're walking into before we ever get on a call. I won't tell you short-term rentals are easy, and I won't tell you you're one property away from quitting your job. You'll hear that from just about everyone else in this space, and it's not true. What I will tell you is that done right, this is one of the smartest things you can do with your money, and I'll show you how to do it right.

What it is

The STR Operator Circle is a community and course for people buying their first short-term rental, or scaling the portfolio they already have.

I walk you through the whole thing. How to find a market, buy the right property, launch it, and run it without it taking over your life. You've also got a community doing the same thing, plus live calls with the experts I bring in and me.

Before you go further, read this

This works best if you've got at least $100,000 to $150,000 to put toward your first property, between your down payment and getting it set up. That number scares some people off. It's what it realistically takes to buy and furnish a property that actually performs, and I'd rather be straight about it up front than waste your time later.

If you're not there yet, the one-on-one side of this won't be worth your money. You can still get in the room, go through the whole course, and sit in on every call while you get ready.

The other thing to know: this takes real work up front. Once a property is set up and automated the right way, it gets close to passive. Getting there does not. If you're not willing to put in the hours to do this right, I'm not your guy.

Tier One: Course + Community

Everything you need to buy and run your first property, plus an evergreen community.

The course:

Finding and analyzing a market, including how I use AirDNA
Underwriting a deal, with my own spreadsheets and market-discovery tools
Pricing strategy and listing optimization
Guest messaging templates and communication systems
Property management, plus the software and automations that keep it from taking over your life
Short-term rental tax strategy
Interior design that actually gets you booked, which matters more than most people think
The legal and entity side, set up right

The community:

A living, active room of people actually doing this, first-timers and seasoned operators sharing what's working and posting their wins and numbers. Real value when you're figuring out your first deal.
Live calls where we break down real deals and tune up members' listings and pricing
Group calls where I bring in experts to teach and answer questions: a short-term-rental designer, my lender, a CPA, a bookkeeper, and more coming. These are teaching sessions, not free done-for-you services, but you'll learn straight from the people who do this at a high level.
Every call is recorded. If you miss one, you can catch the replay, and when you join, you get the whole back catalog of past calls plus everything going forward.

Tier Two: Course + Community + Six Months With Me

Everything in Tier One, plus six months of weekly one-on-one time with me.

This is for people who are ready to buy now and want me in their corner through the whole thing. It starts with an hour-long onboarding call where we map out your full six months. From there, you've got a thirty-minute one-on-one with me once a week when needed, to work through deals, get feedback, or problem solve.

My Guarantee: The weekly one-on-one runs for six months only. Whenever you're ready to launch, I'll personally sit down and launch that first property with you, until it's live and running right. The coaching window ends. My showing up to launch with you doesn't.

If this sounds like you, fill this out before we talk

Tell me a bit about where you're at so I can point you in the right direction.