
20 Minute Investor This “Dirtbag” Hiker Built a Boutique Hotel & Real Estate Portfolio
He lived in an RV behind a duplex. He hiked both the Appalachian and Pacific Crest Trails. Now he runs a boutique hotel in Montana — and built a real estate portfolio that funds a life of freedom.
In this episode, I sit down with Joe Jimenez, a hospitality entrepreneur, adventurer, and real estate investor who proves you don’t need 100 doors to win.
Joe shares how he and his wife Katie started out living in a retirement RV park (in their 30s!), transitioned from dirtbag hikers to boutique hoteliers, and learned to host short-term rental guests better than most landlords manage tenants.
We talk about:
- House hacking with a motorhome (literally behind a duplex)
- Why he left long-term rentals for hospitality
- Building a guest experience that actually meets expectations
- Making the leap into partnerships and handling the pressure
- Designing a business that fits the lifestyle you actually want
If you’re thinking about short-term rentals, partnerships, or how to build real estate around your ideal life — this one’s for you.
00:30 Introduction
02:03 Building a Real Estate Portfolio
07:06 House Hacking Journey
13:35 Transition to Hospitality
24:33 Defining the Ideal Guest
25:30 Learning from Early Experiences
27:08 The Importance of Taking Action
30:01 Balancing Vision and Action
38:10 Partnerships
