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.
The badge
While I was still at Berkeley, I went on a ride-along with the Oakland police department. That night changed my whole path. I fell in love with police work, and I knew right then it was what I wanted to do. I finished my degree in legal studies and set my sights on becoming a detective.
I started out in Silicon Valley working the jail, then patrol, and I made detective at twenty-eight. I started on the cases nobody wants, the fraud and the elder abuse, and worked my way up to major crimes, including homicides, sexual assaults, and Internet Crimes Against Children.
Every cop has war stories, and I'm not going to sit here and drone on about mine. But I will say the one thing most of us won’t. That work fucked me up. The cases involving kids stick with you. It took a piece of me, and it took time from my family I won't get back. I was good at the job and proud of it, but it was taking everything I had, and I didn't fully see that until later.
The turn
Alyse and I started buying primary homes when we were twenty-two because we understood two things early: the power of appreciation and that, as a married couple, we could shield up to $500,000 in gains from taxes when we sold a primary home.
The strategy was simple. Buy the right house, live in it for at least 2 years, put in the work to add value, then sell. Doing that, we forced more than a million dollars in appreciation.
It all started with a $300,000 condo Alyse insisted we buy before anything else. We had almost no income at the time, so we even needed a co-signer to get it done. She saw what real estate could do before I did.
By the time short-term rentals came onto our radar, we were well-versed in real estate and had built real wealth in it. However, short-term rentals were a different animal, and honestly, we knew nothing about them.
Then one critical incident on the job forced the doctors to put me off work. That was the wake-up call. I realized how much of our life was riding on a single government W-2 paycheck, and that it was time to go all in on real estate. We invested in the right mentor to learn short-term rentals, and we launched our first one.
The first property
Our first short-term rental was a $325,000 house in Atlanta that I bought sight unseen.
Because I was hurt and on disability, my income wasn't guaranteed, so the only loan I could get was a no-doc loan at almost ten percent interest. The down payment wiped out our entire rainy-day fund. We had nothing left after that, so we furnished the whole place on two zero-percent credit cards, about forty grand between them, and still ran out of money before we could touch the backyard.
So we flew out to Georgia with the three kids and lived in the house for three weeks while we set it up. Alyse took point on the design and built most of the furniture, night after night. I handled the guest setup and systems, pitching in on the build as much as my injuries would let me. Five bedrooms, and we put it together ourselves because we couldn't afford not to.
We listed it on Airbnb, and it worked. The second month it cash-flowed, and that was the moment we knew this was real.
The point of no return
Not long after, I got news that had a massive impact on both our immediate and long-term future. The doctors told me it was too dangerous to ever go back to the job. The career was over, and the one steady paycheck our whole life ran on was gone.
So we made the most uncomfortable decision of our lives. We sold what we thought was our forever home, moved our family to another state, and rented for a year while we poured almost everything we had into short-term rentals. We had no safety net, just a calculated bet on ourselves. Once things stabilized and the income was real, we bought our actual forever home. We bet big, and it paid off, because we knew exactly what we were doing.
Building it, then teaching it
That first house in Atlanta is still ours, and it runs better now than it ever has. It turned into a second property, then a third. Today I run a portfolio of five properties, doing over a million a year in gross revenue, and I run it from home, which means I actually get to be around my kids.
Somewhere along the way, I started coaching. It began alongside the mentor I'd learned from, and it grew from there. Since then, I've personally coached over 200 people through the process of buying and running their first short-term rental, and helped launch more than 100 properties across 30 states and three countries. That's enough deals to know a good one from a bad one on sight, and enough wins and failures to know what actually matters.
A lot of the people teaching this are in their twenties and caught the easy years, back when you could throw almost anything on Airbnb, and it worked. I did this with a wife and kids depending on me, after a full career spent dealing with people at their worst. Hosting is a people business, and staying calm while you put out a fire is a skill I already had.
That's why I built The STR Operator Circle. I got tired of watching beginners get handed a fantasy. The whole "you're one property away from quitting your job" just isn’t reality.
What I will tell you is that the compound effect is real, and the sooner you start, the sooner it actually changes your life. I'm not going to sell you dandelions and rainbows; I'll show you how to actually do it, honestly, from someone who's done it more than a hundred times, and I’ll tell you the truth even when it costs me the sale.
What it's all for
None of this works without Alyse.
We've been married ten years, and she's in every part of this. Her background is in design; she's worked on projects you'd recognize, and she designs most of our properties herself. This is a two-person operation, and it always has been.
Now we have four kids, all under ten. For a long stretch, I was a dad who was barely around, first because of the job, then because I was trying to get our short-term rental business off the ground. I don't live that way now. I still work hard, harder than most people would guess, but I can stop in the middle of the day and actually be with my kids.
So when I talk about short-term rentals, I'm not really talking about real estate. I'm talking about building something that hands you your life back. I teach because I've watched it change people's lives when they do it right.
