Welcome to the CRE podcast. 100% Canadian, 100% commercial real estate. What if the global geopolitical churn is actually creating opportunities to realign your portfolio?
In this episode of the Commercial Real Estate Podcast, powered by First National, hosts Aaron Cameron and Adam Powadiuk are joined by Jason Castellan, Co-Founder and CEO of Skyline Group of Companies, to explore how Skyline has built a $10.5 billion real estate portfolio by focusing on secondary and tertiary markets across Ontario. Jason shares the investment philosophy behind identifying resilient communities, why markets tied to strong local ecosystems create long-term opportunity, and how municipal partnerships are unlocking major development projects.
The conversation covers navigating affordability challenges, building trust with investors during market uncertainty, and using technology and AI to improve property management. Jason also explains why patient capital, community-first thinking, and disciplined execution continue to drive sustainable growth in commercial real estate.
What you will learn:
- How to identify recession-proof secondary markets using a simple thesis
- Why direct investor relationships are your competitive moat
- The municipal negotiation playbook
- How to reverse-engineer affordability into pro formas
- Why AI adoption today determines competitive advantage tomorrow
- How supply-demand fundamentals favor patient capital
Jason Castellan is the Co-Founder and CEO of Skyline Group of Companies, where he leads the company’s strategic direction across real estate investment, development, asset management, and investor relations. With experience in acquiring, owning, managing, and financing income-producing real assets since 1991, Jason has helped grow Skyline into a major Canadian real estate organization. He is known for his community-focused investment philosophy, emphasis on long-term investor relationships, and entrepreneurial leadership. Jason is also a graduate of Ivey Business School’s QuantumShift program and has been recognized as one of Canada’s Top 40 Under 40.
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