From Marketing Pro to Professional Property Manager

In this episode of the Hospitable Hosts podcast, we welcome David Hillar, Co-Founder of Casa Co-Host, a short-term rental management company operating in Southern Ontario and Alberta. David is also a Hospitable user and investor.

Chatting with Miles, David shares how he got into short-term rental management, how he and his business partner built processes and procedures, and how Hospitable AI-powered automation enabled them to focus on enhancing the guest experience, growing their partner base, and scaling their business.

Press play now to learn how David turned his side hustle into a full-time STR property management business and how technology helps him scale.

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

How David Got into STR Management

As a strategic and creative marketing professional with over 20 years of experience, David entered the short-term rental industry by happenstance. It was David's business partner who introduced it to him.

"He was doing some lead generation marketing for someone in the short-term rental space. He realized that the leads were quite plentiful in this market and that they were very cost-effective to acquire. And so the person for whom he was doing the lead marketing ended up saying that this was a very teachable business, something anyone can do with a bit of smarts, know-how, and understanding of how the market dynamics work. And so we took an education from him initially to get into the space."

David and his partner started managing STR properties as a side hustle and turned it into a full-time business. Now, they manage approximately a hundred properties in Ontario and Alberta, utilizing Hospitable to streamline their operations. "We're committed to scaling the business now, to growing a partner base, and to evolving the processes and procedures we have behind them as well."

Building Business Processes

David admits that when they started, they didn't know much about hospitality, so everything was in a state of "scramble mode." They were focused on convincing property owners to trust them with their investment properties or home suites. Since David has worked in marketing and sales for 25 years, that was the easier part of the business for him.

The more challenging aspect of the business was determining the best approach to communicating with guests, offering them good value, and meeting their needs and expectations. So they had to learn about "the softer ends of hospitality."

"As we evolved with some of the tool sets (Hospitable is a great example), as we could compartmentalize things like messaging on an automated basis with cleaner reminders, we could focus more on how we can improve the experience for people physically on the property and how we can build better marketing and sales chops as well to tighten up those processes."

David points out that using the right software enabled them to do what they do best—sales, marketing, and overseeing a business — instead of spending all their time completing routine, repetitive tasks.

Hospitable's Features That Make Hosting Easier

David relies on Hospitable's automated messages to ensure fast and clear communication with guests and considers automation "the number one feature" for their business. He also thinks that integration with smart locks is fantastic because it makes check-ins and checkouts easy for guests and is "a trust-inducing factor" for property owners. They also utilize Hospitable's channel manager functionality and integrations with AI-powered pricing tools, enabling them to update calendars and prices across multiple booking channels quickly.

Finding the Right Property Manager

David also shared some advice for property owners considering hiring a property manager for their short-term rentals. He recommends that property owners take into account some critical factors to ensure they can benefit from it:

• Understanding what's involved in property maintenance and how to make a rental look appealing to guests;
• Having the systems and processes in place to ensure seamless day-to-day operations;
• Having people responsible for performing essential tasks.

"I think there can be a great manager who can manage 5 or 10 properties really well, but can they manage 40? Can they manage 50 effectively? Just relying on the tools and one body 24/7 is a tough sell for me. Knowing that many people behind it have your back if something goes wrong and that they have the right experts on board is important. So that's how we've scaled our business to where it is."

Deciding Which Property Owners to Work With

David reveals he doesn't say yes to every potential client that comes along. "A lot of it comes down to the conversation and the reason someone is looking to this space in general," he says. Many property owners choose to be in short-term rentals because they want to get consistent income and "maintain that flexibility with their home as well," and David thinks these are good reasons.

"If you have a professional manager, you're to have responsible guests in there. Your monthly payments are almost guaranteed as long as they're doing their job. So my first question is always, why are you in this? And if their answer is money above all, I take caution there because things can be inconsistent.

It's also important to establish trust with the owner and be sure they won't micromanage you. "You don't need to be peering into the platform to say, "Why did we say this and not that?" I'm OK with those questions, especially initially. However, you've got to trust that we've been doing this for years now, that we have a team in place that is well-briefed on their responsibilities, and that we know what we're doing. So if I can't establish that level of trust with an owner as well, that's a warning sign for me going into that as well."

Listen to the full episode of the Hospitable Hosts podcast to discover how David transformed his STR side hustle into a thriving property management business and what skills and tools helped him succeed.