How Three Friends Turned a Student Rental House to Billions in Assets May 14th

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…