Bigger Assets, Better Leverage

Jason Castellan

It all started in 1991, when University of Guelph student Jason Castellan and his brother, Martin, were just trying to make a little extra money through property ownership. Twenty-three years later, Castellan is CEO of the Skyline Group of Companies, which oversees three real estate investment trusts (REITs) valued at more than $1.6 billion. Here, in numbers, is how he and his partners made it happen.

2 brothers

The Castellans started slowly. After renting for one semester in university, they bought a small house with their father’s help, living in the basement while renting the upstairs to three roommates. Then, when the house across the street came up for sale, they decided to repeat the process.

52 houses

Seeing the benefits of an income stream, the brothers decided to broaden their scope and teamed up with another friend, Roy Jason Ashdown. Together, they did some “market research,” which wasn’t hard, given their university’s nightlife. “Going to keg parties from Thursday to Sunday, we saw a lot of houses,” Castellan says. “And the first thing we’d ask was, ‘How much do you pay in rent, and what does it include?’”