Mission-Driven Hosting: How Crewdogs & Hospitable Empower US Military-Connected STRs

In this episode of the Hospitable Hosts podcast, we welcomed Adam Hill and Tony Romeo, US Veterans and Co-Founders of Crewdogs, a travel platform for the military community to share homes, rooms, and spaces. Adam and Tony shared how they created an exclusive online platform to help the military community support each other and the causes they believe in.

We were also joined by Hospitable customers Jena Hartman, Mike Costello, and Pat Walsh, who are military community members and list their properties on Crewdogs. Jena is currently a T1 instructor, and together with her husband, she manages STR, mid-term rental, and long-term rental properties. Mike Costello, an Air Force veteran, and Pat Walsh, currently on active duty in the Air Force, are Co-Founders of CoHostTexas, which offers co-hosting services.

Jena, Mike, and Pat shared their experience hosting on Crewdogs and how they use Hospitable to streamline operations. Our guests also gave some advice for military families or veterans considering hosting and shared their plans for growing their business in 2025.

Press Play now to learn what inspired Adam and Tony to build a travel platform for the military community, what inspired Jena, Mike, and Pat to start hosting, and how Hospitable helps them manage their rentals efficiently.

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

How Adam and Tony Came Up with the Idea of Crewdogs

Adam has a deep passion for the military community because he comes from a military family—his grandparents and father served in the Army. "And what I saw throughout my service was a disconnect from our ability to find and talk with each other. We're just fragmented across a bunch of different platforms. And then, especially as it pertains to travel and housing, how do we find extra rooms? How do we connect to those we trust?"

When Adam met Tony, they started to build a platform to bring the military community together, focusing on the trust aspect, to support each other. "We're excited to connect people like Jena, Mike, and Pat, and bring them in, and give them a platform to reach that community. And then also give them a way to pour back into some of the causes that support us."  

Last year, Crewdogs partnered with nine nonprofits and started distributing donations to support those causes. "This is about the military community; it's about all of us coming together for the same reason, and that bond is because we all served or our spouse served," Tony says.

How Jena, Mike, and Pat Started Hosting on Crewdogs

Jena and her husband started with long-term rentals but knew little about real estate. But they wanted to keep growing their business, so they added short-term rentals. This strategy allows them to make more money and build their portfolio faster.

Jena started hosting on Crewdogs because she loves giving back to the military community. "But on the other hand, you have to think of it like a business owner. The more places your property will be on, the more people you'll reach, and the more bookings you'll get."

Mike's first hosting experience was during a 2018 deployment when they lived in Rapid City, South Dakota, a natural tourist destination. In 2021, Mike partnered with Pat, and they jumped into the short-term rental space, starting with just two properties.  

"And we realized we've got Hospitable, PriceLabs, Rankbreeze—a tech stack, and we think we're good at this. Why not try this for other people?" And that's how our venture into vacation rental property management began there."

Last year, they found Crewdogs on Facebook and joined their group because they love hosting military families. "So anytime we can get more plugged in with the military community and provide a safe, clean place for military and their families to stay is just awesome for us," Pat underlines.

"Crewdogs reaches a part of the market not tapped into by Airbnb and Vrbo," Jena adds. "It's funny because we have more trust in the guests, and the guests have more trust in Crewdogs."

How Hospitable Makes Hosting Easier

Jena underlines that Hospitable is key to their business. Her husband and she are pilots, so they're very busy, but they can still run STRs because Hospitable automates almost all operations. She likes that Hospitable automatically syncs calendars on different platforms and sends automatic notifications to her cleaners. Her favorite feature is team collaboration. It allows her to connect her team members and owners to her Hospitable account, giving them direct access to the necessary information and features.

Mike is impressed with the Hospitable team's progress in building new advanced features, "different aspects of direct bookings," brand development, and marketing. He thinks Hospitable is the most advanced tool in their tech stack. "And it's super impressive that you guys don't rest on what you've got, but you continue to build."

Advice for New Hosts

Jena thinks that to build a thriving STR business, you should "get into the game" and learn from experience. "Just make that next step and buy a property, get into STRs, and get going, and then learn along the way."

"There's probably a lot of myths around STR that it's easy money," Mike points out. He thinks it's crucial to treat short-term rentals like a business. "Run it professionally; respect your own time and the time of your guests, clients, and local team on the ground."

"Know your numbers," Tony adds. You must estimate your upfront and ongoing expenses, as well as potential income, before you jump in to ensure it's a good investment.

"It's never been a better time to start a company," Adam underlines. "In the age of automation, there are so many tools out there. You can build a tech stack and automate many things that, a decade ago, took hours and hours a day. So do your research on the tech side and then partner with somebody like Hospitable, who's turning out new features and updates every week and makes your life a lot easier."

Listen to the full episode of the Hospitable Hosts podcast to discover how Crewdogs and Hospitable empower military community members to grow a successful STR business on the platform while supporting veteran foundations.