How Three Friends Turned a Student Rental House to Billions in Assets

Small-town entrepreneurs behind Skyline’s success, 30 years in the making

In 1991, brothers Jason and Martin Castellan made their first real estate acquisition: a student rental house in Guelph, Ont. Their first investor? Their dad. They were joined in their business venture by their friend R. Jason Ashdown a short time later and continued to grow their student rental housing business. The three co-founders, along with CFO Wayne Byrd, have grown the business into Skyline Group of Companies (Skyline), now managing $5.4 billion in assets in over 150 communities across Canada. How did the co-founders—who all still work together every day—do it?  

“We’re stubborn,” says Jason Castellan, Skyline’s CEO. “We like to see things through, and if it doesn’t work one way, we’ll try it another way until it does work.” While he says their success has been “unbelievable,” it hasn’t happened overnight. “It’s been a lot of grinding and bringing on a lot of really great people who offer new insight and innovation to our processes, which results in those processes consistently improving.” 

After that first investor, Skyline grew by word-of-mouth. Today, more than 4,500 investors are served by Skyline Wealth Management Inc., the exclusive investment dealer for Skyline’s investment funds. Castellan describes these investors as “everyday people like you and me,” stating that more than half have come to Skyline by way of referral from a friend or family member. Initially, Skyline focused on apartment real estate, offering its apartment portfolio as a Real Estate Investment Trust (REIT). As the business continued to grow and evolve, Skyline saw an opportunity to establish a second REIT focused on light industrial real estate, then a third focused on retail real estate properties anchored by national-brand grocery and pharmacy tenants. Skyline’s fourth and most recently launched fund focuses on clean energy. This fund was sparked by the rooftop solar panel systems the company had been installing on its properties to create an additional revenue stream. “We’ve always had a penchant for being efficient—and for finding new ways to surface value,” says Castellan, “and from these solar projects, we saw the potential to bring our investors further value by offering an investment fund in clean energy.” 

Most of Skyline’s apartment and retail real estate assets are in secondary and tertiary markets, a strategic choice that has served Skyline well during a pandemic, which saw an exodus from cramped city downtowns. “Like our business partners, Marty and I grew up in small-town Ontario,” says Castellan, originally from Walkerton, Ont. “We played hockey in a lot of the small towns we now own real estate in, like Port Elgin and Kincardine. Each of these towns has its own vibrant characteristics, and we’ve found the same in our additional communities across Canada.” They also knew that these were the kinds of places where people and businesses tend to be “sticky,” having stable populations without the churn that may be seen in bigger markets.  

Beyond the real estate ownership, Skyline creates job opportunities and strives to become a part of the fabric of its communities by finding ways to give back. For example, in Fergus, Ont., Skyline transformed a large unused retail space into a hub for local community support organizations. “Investing in our communities is a crucial component to our success,” says Castellan. “When we’re doing good things in these communities, our staff can feel good about where they work, our tenants can feel good about where they live or operate their businesses, and our investors can feel good about where they invest.”