From Renting Out a Single Basement Unit on Airbnb to Managing 60+ STR Properties

In this episode of the Hospitable Hosts podcast, we welcome Tracey Choy, CPA, and Aahil Matcheswala, CFA, Co-Founders of Dongle Capital and Hospitable users. They started by renting out their basement's single room on Airbnb and built a successful property management business. Today, Tracey and Aahil manage 60+ properties across Canada and have an Airbnb Superhost status.

Chatting with Miles, Tracey and Aahil shared how they remotely manage STR properties in different provinces, using technology to overcome challenges and provide quality customer service for guests and property owners. 

Press play now to learn more about Tracey and Aahil's journey and how they scaled to manage over 60 short-term rental properties nationwide.

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

How Tracey and Aahil Got into STR Management

Tracey reveals that they started their journey without any hospitality background. It all began at the end of 2020 when they both worked corporate jobs and decided to list a room in their home in Kitchener, Ontario, on Airbnb to supplement their income.

Their Airbnb hosting experience was a success, and soon, their friends and family asked them to manage their properties. "So it was something very organic. It was nothing, moved to a side project, and quickly became a passion for us."

Tracey and Aahil quit their corporate jobs, did rental arbitrage for about a year, and scaled to 50 units within that year. Then, they pivoted to a full-service property management business. Now, they manage STR properties in 3 provinces: Ontario, New Brunswick, and Nova Scotia.

Want to see one of their amazing Airbnb properties? Watch the video in which Tracey and Aahil talk about their experience hosting guests at The Rosé House.

Challenges of Remote Hosting

Tracey admits that remote hosting can be scary initially, but once you start managing your first remote listing, you feel more confident. "It's all the same, and once you have your processes in place, you know what needs to get done."

As they onboard a new property, they ask the owners to give them a video tour of the rental space—that helps them "set the landscape for things" and document all their processes. Then, they hire cleaners and handymen to take care of the turnover cleanings, repairs, and maintenance.

"Even for our basement short-term rental, we rarely attend to it in person. We're not the ones cleaning it. It doesn't matter if you're remote or on-site; as long as you have strict processes in place, everything runs as it should be," Tracey underlines.

Aahil thinks the biggest challenge in property management is finding the right people "who want to grow with you" and "care about the quality of the work they provide." But managing listings remotely isn't a big issue. "The remote aspect, that's where technology comes in. We have tools like Hospitable, PriceLabs, and Turno to help with everything technology can do."

Qualities of a Good Property Manager

Tracey shares three qualities that property owners should consider when choosing a trustworthy property manager." First of all, they have to be tech-savvy. If someone tells you they do everything manually, it's just impossible these days."

Although you can't solely rely on technology, it helps you save a lot of time. Using the right tech stack in your business ensures you can manage multiple properties efficiently. "You have to make sure that you are systemizing and that there's consistency in your service."

Property managers must also be good problem solvers and have strong communication skills. "It's about having high EQ and being able not just to answer questions but anticipate what other follow-up questions there are or what other things a guest or an owner should think about. It's important not just to give them the answers they're asking for but also to foresee what they would expect and tell them what could happen."

What Makes Them Passionate About Property Management

Tracey loves meeting people from different walks of life and impacting their lives, which she never experienced when she had a corporate job. "I'm not just talking about guests, but it's the property owners. You know, helping them give a lift to their property because they've had a long-term tenant overstay, and now they're in the red for a long time, and now they need something better, and we're that solution for them."

Aahil likes property management because he enjoys new challenges and building new things. "For me, it's more the technological aspect, being able just to systemize everything in the business, have an SOP for everything, have a process, have a system."

Business Goals for 2025

Aahil says they want to continue growing their business sustainably, allowing them to keep their existing customers happy. "50% of the units that we've added in the last 14 months, they've been through word of mouth. So if you keep your existing clients happy, the growth takes care of itself."

Tracey and Aahil have a team of virtual assistants—they call it the second line of defense. Their big goal is to move up to the third level of defense. They've already recruited a person who can help them lead the virtual assistants and "remove all the silos between different departments."

"And then we're moving up when that second line of defense has questions, and we're there for them. So, prepare them for success. So that means having all the right documentation in place, educating, and training them on all the right decision criteria. I feel like a lot of information is right now in our heads. So just putting it down on paper," Aahil explains.

Tracey and Aahil also created their own YouTube channel. "We feel like much of our content is better suited to longer-form content. And also, on top of education, it's just a good source to show our work and how we help clients."

Listen to the full episode of the Hospitable Hosts podcast to get inspired by Tracey and Aahil's journey into short-term rental management and discover the secret of their business success.