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