Updated on April 27, 2023

University and military service took brothers Evan and Phil Wilburn in different directions after growing up together in Tennessee.

While stationed with the Air Force in Colorado Springs in 2016, Evan bought a five-bedroom house and started renting out rooms on online short-term rental platforms to help cover the mortgage payments, maintenance, and improvements.

Not long after that, fresh out of the Air Force and ready to start university classes, Phil joined him there and also bought a house and started renting out rooms for short-term stays.

When Evan tried to find a property manager to help him manage the short-term rental in his home, he learned that there were few property management companies in town that specialized in short-term stays.

With about 1,500 short-term rentals in Colorado Springs, the two brothers realized they had discovered an unfulfilled need in their community and had an opportunity to start their own property management business.

“At the time, I didn’t know the whole vacation rental industry existed; I thought it was mainly homesharing,” Evan said.

Their first business model was to manage rooms for rent in people’s houses, but they quickly started receiving requests to manage entire homes.

“It was a side hobby we were going to start, and there ended up being a flood of business,” Evan said. “Phil was going to school while cleaning units, taking guest calls, and communicating with owners. I was working nights and weekends while I was still full-time with the Air Force.”

Building a short-term rental property management company

In 2017, the brothers officially founded Hostē, which stands for “host easy.” The company has since evolved into a full-service solution designed for owners who don’t have time to do the hosting themselves but still want stellar professionalism, customer service, and quality for their guests.

In a short period, Evan and Phil had to figure out how to hire employees; lead their team; develop cleaning, maintenance, and safety protocols; set up 24-hour communication with guests; and manage thousands of transactions and funds to owners. 

“It’s a more challenging business because it’s essentially five businesses in one,” Evan said.

By the end of 2018, the Wilburn brothers were managing about 30 properties. That same year, they and other short-term rental operators faced new regulations.

Advocating for short-term rentals during regulation-making

Colorado Springs City Council initially proposed restrictions that would have put Hostē in jeopardy, including a proposal to allow short-term rentals only in primary residences.

So, the Hostē team sprang into action. As part of an advocacy campaign by the Colorado Springs Short-Term Rental Alliance, they produced a video featuring STR operators and their employees who told their individual stories of how STRs had impacted their lives.

In the video, a housekeeper described how working at Hostē allows her to make a living, and Evan noted that Hostē paid housekeepers higher wages than a well-known luxury resort in Colorado Springs.

“I have bills every week, I have birthdays every three months, so I’m just trying to do whatever I have to do to keep me happy, keep my family happy, keep people at work happy,” said Janay, a housekeeper at Hostē. “I need my job; everyone needs some kind of income.”

The final ordinance in 2018 set up a fee, permit, self-inspection checklist, and minimum liability insurance requirements.

The following year, however, City Council members implemented more restrictive measures such as limiting short-term rentals to certain zones. While zones were eventually implemented, many of the existing STR operators were grandfathered in.

Educating others on responsible short-term rental management

Hostē now manages nearly 200 properties and 26 employees, not counting housekeepers who are contractors.

Building Hostē from the ground up was an educational transformation. The Hostē team now shares their knowledge and knowledge of vacation rental experts with others in the industry through their podcast, STR Intel.

The podcast often focuses on responsible renting practices such as guest screening, accessible design, and safety.

“We basically just wanted to hold ourselves to a high standard of safety and to make sure that our guests are not only having a great experience but that they’re also safe when they’re at the home,” Evan said.

Justin Ford of Breezeway helped the Hostē team develop a 100-point safety checklist and quarterly preventative maintenance that includes checking for safety items.

Part of Hostē’s focus on safety means having the right insurance policy for their properties. They primarily use Proper Insurance.

Proper specializes in short-term rental properties and has a la carte products geared for the industry and specific risks.

“Proper is the gold standard when it comes to insurance in this industry,” Evan said. “They know this space well and write really good policies unlike some of the bigger insurance players. I can always trust that our clients and Hostē are getting the correct coverage. 

“Short-term rentals are a difficult space to navigate, and Proper almost has a product for everything,” he said. “As far as safety, guest screening, and a lot of the risks that come with short-term renting. Having the correct insurance is really that last line of defense everyone should have if they are going to get into this space.”

“Luckily, we haven’t had an event happen, but if you’re getting to 50-100 homes, the probability that something might happen increases,” Evan said. “If you want to rent responsibly, the key is to make your home safe first.”

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This article is a part of our Forward Thinkers series powered by Proper Insurance

Proper Insurance leads the nation in short-term rental insurance, with over 100,000 policies written in all 50 states. Their policy covers vacation homes, townhouses, condos, duplexes, cabins, cottages, apartments and more. With expert vacation rental underwriters, they can tailor a policy specific to your short-term rental property.

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