From STR Side Hustle to Full-Service Property Management Business

In this episode of the Hospitable Hosts podcast, we chat with Josh Difani, Licensed Realtor and Owner of Hidden JEM Hosting, offering full-service property management in Northeast Oklahoma, Northwest Arkansas, and Kansas City, KS.

With over a decade of experience in real estate investing and sales, Josh specializes in selling real estate and managing short-term rentals for clients who want to make their investments passive. Currently, Josh manages 26 STR properties and uses Hospitable to streamline operations (he is our Mogul plan user).

Josh shares how he and his wife first got into short-term rental hosting, why they started managing STR properties for others, their business goals, and how they vet property owners to work with. He also shares what he loves about hosting and what makes their business different.

Press Play now to learn how Josh has turned his side hustle into a full-service property management business and what tech stack he uses to make his business more efficient.

If you prefer to read the highlights, we’ve got a summary of the key takeaways below.

How Josh Got into the STR Industry

Josh says he sells real estate (he has been a realtor for about 8 years now), and he loves investing in real estate.

“My wife and I have been investing in long-term rentals and have had a few long-term rentals. And I’m a visionary dreamer, always looking for the next thing, not very content. So, I thought I’d try my hand at short-term rentals. We selfishly wanted a place that was kind of a weekend retreat for ourselves and that we could also short-term rent when we weren't there.”

They discovered a new cabin that was under construction in a small community on Grand Lake in Oklahoma, approximately an hour and 15 minutes from their home. Josh hired a property manager to run his STR property for him, but it was a bad experience, and within about 30 days, he had to let them go.

Then Josh found a local cleaner and a handyman and started self-managing the rental. “We had a lot of bumps and learned a lot in that first 3 to 6 months, but we figured it out, and realized that we could do a better job at it than anybody else.”

Starting a Property Management Business

Now, Josh has a co-hosting business and manages 26 short-term rentals. He says it all started 3 years ago with a friend who had a short-term rental and was unhappy with their property manager, so he asked Josh to help them.

That was their first client. Josh says he did not intend to start a business. “But we blinked, and within 6 months, we had 6 B&Bs. We were co-hosting for just friends, really just word of mouth. We weren’t even really spreading the word.”

Then they realized that there was a significant need for co-hosting services in the market, so they decided to turn it into a business officially. They created social media accounts that Josh’s wife manages, started marketing their services, and within a year, they had gone from 6 to over 20 properties.

Vetting Properties and Owners

“We were just taking anything and anyone who wanted the help, and we didn't know how to vet owners yet or even really vet properties,” Josh reveals. So, they grew quickly and then realized that they didn’t have “great relationships” with some owners.

“It just wasn't a right fit between us and some of these owners. Our vision and values didn't align. And then some properties just weren't the right property or in the right place or didn't have an owner that was committed to furnishing or stocking well.”

So, they dropped some of their clients. “We started casting more of a vision for what we wanted, and what the ideal client was, and the ideal property, and just learning a ton each day.”

Josh says they have three criteria that a property needs to meet to have success as a short-term rental: location, uniqueness, and amenities. “You've got to have 2 of the 3 to have success in our eyes,” he notes. “That’s our biggest initial evaluation of a property, and then it goes deeper from there.”

Their Tech Stack

In addition to Hospitable, Josh uses other technology tools to help manage their short-term rentals. He says that Schlage Encode is a lifesaver for them. “It’s a huge security advantage, and it’s a time saver too. And then, it integrates so seamlessly with Hospitable.”

They also use QuickBooks for bookkeeping and PriceLabs for dynamic pricing. “I was just evaluating yesterday the new dynamic pricing with Hospitable, and I’m very interested in that,” Josh adds.

What Josh Loves about Hosting

“What I love about hosting is, honestly, that my wife and I work in it together. I handle most of the day-to-day work, and I'm the face of the company, but she’s involved in it a lot with me. She’s my sounding board for everything and plays a huge role in the business too,” Josh reveals.

He also says that they are hospitable people in general and love to host family and friends at their house. “So, I think it’s a natural fit for us. We pour ourselves into these B&Bs, wondering, what would we want if we were hosting people here?”

“And I always say short-term rentals are less real estate, more hospitality, but then it’s also an investment because it can generate cash flow. And someday, if you turn around and sell it, hopefully, your equity gains will have increased. I’ve always been a nerd on the real estate side, too. So I get two sides of it, the hospitality and the real estate.”

Tune in to the full episode of the Hospitable Hosts podcast to get inspired by Josh’s journey into short-term rental property management and learn about the strategies that help him succeed.