I didn’t set out to build a rental business. I was just gone most weekends and didn’t want my house sitting empty — so I started renting it out and crashing at my parents’ place whenever it was booked. That’s it. That was the whole plan.

How It Started

That first booking turned into steady income. I had zero real estate background — pricing, furnishing, talking to guests, all of it I figured out as I went. A year in, I’d saved up enough for house #2.

What I Learned

Going from one house to four taught me more than any course could — mostly by messing up. It gets easier every time, and if something can go wrong with a mid-term rental, I’ve probably already lived through it.

The biggest shift was ditching the short-term, Airbnb-style hustle for mid-term (30–180 day) stays — more stable guests, way less turnover, a lot less day-to-day headache. Somewhere in there I also noticed a real gap: people who wanted to do this too and had no idea where to start.

Today

I don’t technically have a primary residence anymore — I live in my own rentals and bounce around the country. Selfishly, I just wanted cool places to stay. Turns out it also built real wealth on top of a full-time job I still love.

I’ve helped a few friends start their own mid-term setups, and honestly, more competition just makes it better for guests. 🙂

Midterm Mastermind is me sharing the model — and the mistakes — so you don’t have to learn it the hard way.

The Quick Version

• 4 mid-term rental properties
• $100K+ in annual rental income
• 8+ years doing this
• No fixed address — I live in my own rentals full-time
• Still clocking in at a full-time job I actually love
• Favorite hike: Angels Landing
• Favorite city to visit: Bozeman