Scaling Property Management Business: the Story of Brendan Thompson

In this episode of the Hospitable Hosts podcast, we welcome Brendan Thompson, entrepreneur, real estate investor, and Co-founder of Oikos Property Ventures. Brendan manages 27 short-term rental properties and uses Hospitable to streamline operations (he is our Mogul plan user).

Brendan shares his unique journey into the short-term rental space, starting with his background in the non-profit world, then developing software for short-term rentals, and ultimately growing a property management business. He also discusses the benefits of hosting and being a property manager, emphasizing the importance of having the right tech stack to ensure smooth operations.

Press Play now to find out how Brendan scaled his property management business in just 18 months and what software tools he uses to keep the business going and create a solid foundation for growth.

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

How Brendan Got into the Short-Term Rental Industry

“I did not come with a background in short-term rentals, real estate, or anything like that,” Brendan says. “I was actually in the nonprofit world for over a decade, and being in the nonprofit world, you just don’t get exposed to a lot of the ins and outs of real estate.”

When Brendan was looking for a career change, he found a friend who was developing short-term rental software, which helped people determine whether the property they were buying was a good deal or not.

“That was one of those eye-openers for me where I started to think to myself, are people making this kind of money in the short-term rental world? That seems a little crazy,” Brendan notes. So after a season of working on that software, he and his wife bought their first property.

Brendan met his business partner at a short-term conference. They had very similar visions and were at a similar stage in their business, so they went in together. Shortly after that, they picked up their first co-hosting client. “Since then, it’s been almost two years, about 18 months at this point, and we’ve just been scaling like crazy.”

How Their Business Has Evolved

Brendan admits that when they were starting, they had no experience and didn’t know what they were getting into, but they knew they had to have the right systems in place. Now, they manage up to 27 properties, and their business has evolved as they have had to grow and scale alongside their portfolio.

“We have robust mechanics that help us operate and do things at scale, or at least at 27 listings. Certainly, some people have 100 houses or 150 listings, and that’s a completely different level. But where we are right now is that we’re preparing our systems to grow toward that, so I hope that what we have now actually will scale with us.”

About Their Business Plans

Brendan emphasizes that they serve a highly niche group of people who rely on real estate for their income.

“I came out of this world where we were training people who were going all over the world doing mission work. So they'll work in an orphanage here, or they might do something overseas. And a lot of these people are leaving their homes, and they don’t know what to do with their homes. So that’s where we stepped in.”

Since Brendan had a background in this area and many connections, they have been able to scale quickly. They hope to continue serving this type of property owners and expand their property management portfolio. Brandon’s ambition is to manage 35 or 40 STR properties by the end of this year.

Brendan reveals that he loves helping others and serving them, so they’d also like to shift their focus to assisting co-hosts and property managers who are struggling because they lack the right systems or need a breakthrough in a particular part of their business.

“We’ve done some coaching on and off for different property owners, but that’s something I think we’d like to get into eventually, of course, scaling up our investments through funds and syndications.”

Advice for Property Owners

Brendan shared his ideas on the questions property owners should ask when looking for a property manager.

“Probably, I'd be asking lots of questions, but I think number one, you want to make sure that they like people. You want to make sure that they enjoy the art of hosting. Because if they don't enjoy people and hosting, it's going to be tough for them to be a good man. I mean, they're just going to be salty all the time.”

Brendan also recommends asking property managers about their tech stack and revenue management. “If you ask them how they plan to do revenue management and they don't have an answer, I would probably start to probe and have some deeper questions there. Because if their job is to maximize your revenue, you need to know how they're going to be doing that and what they think.”

About Tech Stack

Brendon uses Hospitable as a property management system with a channel manager, and he likes that there is a public roadmap so he can see what’s coming up. “So, some of the technology that we use, whenever Hospitable has that feature ready, we’re switching as fast as we can just because we like to keep it all contained.”  Brendan thinks that introducing a dynamic pricing feature is a significant step.

He also utilizes the strIQ app for underwriting and helps property owners understand the value of their homes, as well as tools for listing optimization and Breezeway to manage operations.

“I always recommend people right-size their tech stack to where they are,” Brendan says. “But I do think if you’re going to be serious about hosting, one of the first things you need to do is get a good, proper PMS. And Hospitable is mine of choice. I do think that's important because from guest communication to the dynamic pricing, it will reduce your workload substantially.”

Tune in to the full episode of the Hospitable Hosts podcast to learn more about Brendan’s short-term rental journey and the strategies he uses to achieve his business goals faster.