A SW Ontario Success Story with Jason Castellan of Skyline

Jason Castellan is the CEO and Co-Founder of Skyline Group of Companies and joins us on today’s show. The company is located in Guelph, but also has additional offices spanning throughout Canada.

Skyline’s beginnings trace back to the early 90s when Jason and his brother started purchasing single-family homes in Guelph. Jason explains how the company has grown to the size it has today, and also talks about how they decide where and what to invest in.

Topics covered include:

• Jason and his brother’s interesting business strategy when they started in the 90s.
• Why Jason says a lack of originality led to the business being named Skyline.
• What was learned while building up a portfolio of homes in Guelph.
• The help that Skyline received from lenders when capital was hard to come by.
• How Skyline determined what areas to focus in.
• Avoiding competition that is present in larger markets.
• Shifting from the GTA to the GTAH.
• How separate funds came to exist at Skyline Group of Companies.
• The types of retail properties that Skyline gets involved with.
• What goes into deciding to invest outside of Southwestern Ontario.
• Why Jason is so happy that Skyline doesn’t have any office exposure.
• Seeing the return to office as undoing a bad habit.
• Looking back at when Jason and his brother realized real estate could be their career path.
• Collaboration being one of the major keys of Skyline’s success.

More about our guest….

Jason Castellan has been in the business of purchasing, owning, managing, and financing income-producing real assets since 1991. His passion for asset acquisitions, management, and investment has served him well as the CEO for Skyline Group of Companies since its inception in 1999. Recognized for both his entrepreneurialism and industry expertise, Jason believes that although Skyline has its roots in real estate, it is in the people business. By never losing sight of the fundamentals that spurred Skyline’s early growth, Jason has built a major Canadian real estate company spanning coast-to-coast, consistently attracting passionate, like-minded investors and employees with “star” qualities. As Skyline continues to expand its national presence, Jason maintains a belief in providing accessible and personal service to the business’ investor client group that is an integral part of the company’s growth and success. A graduate of the Ivey School of Business’ exclusive Quantum Shift Program, Jason has been named one of Canada’s Top 40 Under 40, as well as one of Canada’s 40 Most Promising Entrepreneurs. He was also designated a finalist for the prestigious EY Entrepreneur of the Year award.

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