I grew up with supportive parents who encouraged me to work hard and gave me room to explore my entrepreneurial side. Business was something I learned by doing. I would see an opportunity, figure out how to make it work, and build from there.
2017One condo in Calgary
In 2017 I started a marketing agency. That was also the year I launched my first property on Airbnb. I had bought my first condo at 21, taken possession at 22, and had it live by July.
Once I saw what was possible, I wanted to do it again. The problem was that I did not have enough money to keep buying properties.
So I got creative. I contacted owners and met them in person. My proposal was simple: I would rent their property and use it for short-term stays. I quickly found an owner willing to give me a chance. The place was across the street from my own condo.
That became my first rental arbitrage deal, in December 2017. At the time I did not even know what to call the model. I had worked out a way to expand using someone else's property before I knew there was a name for it.
Then I ran into my first real constraint. I had not understood the building's bylaws well enough, and I had to stop. That pushed me to find another way to grow without needing the money to buy or lease every property myself, which led me into management: helping owners make their properties work as short-term rentals while I earned money for operating them.
The sequence matters to me. I bought first, then figured out rental arbitrage, then moved into management. I did the work before I taught it.
2018 to 2019Teaching, and the Mrairbnb name
From mid-2018 through the end of 2019, I taught others what I was learning and doing. Education became a meaningful business, and some of the people I taught went on to build substantial operations of their own.
In January 2019 I was invited to New York to teach Airbnb to a much wider audience and help create a course. The Mrairbnb identity grew alongside the business, connecting me with people well beyond Calgary. But the foundation was always practical experience. What I taught came from things I had already done.
2019What if a hotel was on Airbnb?
By 2019 I was thinking about a much bigger opportunity. One apartment was a start. What would happen if I could bring hotels onto Airbnb?
A friend told me he owned a boutique hotel with more than 70 units in Edmonton. Hotels already had rooms, staff and operating systems. What they also had were gaps in their calendars.
I connected the hotel to Airbnb through its property management system and earned a percentage of the bookings that came through that channel. The important part was filling available inventory around the business the hotel already had.
That changed how I thought about scale. I could help an existing hospitality business reach more guests without personally buying or leasing every room.
2019 to 2020Resorts, and thousands of rooms
I wanted to take it further. I partnered with a former student in Eastern Canada who also had marketing experience. Together we pursued major hospitality brands and resort groups.
The process took years of negotiation, contracts and technical implementation. We eventually connected Airbnb into luxury resort portfolios with thousands of units, including five-star hotels and resorts across Mexico.
Our role was to help bring those properties into a new distribution channel. The assets belonged to the owners and resort groups, and we worked alongside their teams.
2020 to 2022COVID, and the drawing board
Just as that work was coming together, COVID hit. Travel stopped. Hotels and resorts faced restrictions and collapsing demand. Years of work ran into a world where the industry was focused on damage control.
For roughly two years I questioned what the future of Airbnb and my business would look like. There was little appeal in teaching people how to expand while so many operators were trying to protect what they already had.
I kept returning to one thought: I would rather own one unit than run ten for someone else.
I had started as an owner. Now I wanted to return to ownership with everything I had learned about marketing, distribution and operations. I also wanted to help other people acquire properties and build something alongside them.
SeoulTen units I have never seen
Another opportunity took the operating model much further from home. Someone approached me whose family developed buildings in Seoul, South Korea. They had a building with ten units and wanted help making it perform.
I became the operational centre behind it, coordinating the team and the business remotely. I still have never been to Korea. We reached the top 1% for that property type in a highly competitive market.
After roughly a year, short-term rental licensing requirements changed, and the building could not obtain the licence needed to continue. We had to shut the operation down. That experience sharpened my focus on getting involved earlier in the property itself: its intended use, its suitability, and how the business would operate over time.
DevelopersDesigning stays into the building
I began working with developers on integrating short-term rentals into their projects, in Calgary, Kelowna and other markets. Some wanted to retain units and create income from them rather than sell everything. That created an opportunity to help turn retained inventory into an operating portfolio.
Our role can span identifying the opportunity, underwriting it, hiring the team, launching the properties and running the day-to-day business. Our involvement is specific to each project and the units within our scope.
2025Back where it started
I also wanted to demonstrate what we could do in Calgary, where I started. In 2025 an investor provided the capital to purchase a new property in the city. We built and launched the operation with the ambition of becoming the leading Airbnb property in Calgary. Reaching number one remains the goal.
This project matters to me because it brings the experience back to the city where it began, and applies it to a property at a scale an individual investor can understand.
TodayFewer clients, more meaningful work
I am much clearer now about the business I want to build. I want fewer clients and more meaningful work with each of them. I want the capacity to deliver well, participate in the value we create, and develop relationships that can last.
For people just getting started, my direction is to share useful information freely. Paid beginner courses are no longer the business I want to build around.
Ross Stays now focuses on three groups: real estate investors who want to own and build portfolios of stays, partners who want to acquire boutique hotels, typically under 60 keys, and developers who want to integrate short-term rentals into their developments.
Each chapter has shaped that focus. Buying taught me ownership. Rental arbitrage and management taught me how to build with other people's properties. Hotels and resorts taught me distribution and scale. COVID and Korea taught me how much the underlying structure matters.
I started by figuring out how to make one property work. Now I am building a business around helping the right partners own, operate and improve hospitality assets.