102. From Small-Town Roots to $9 Billion in Assets: Jason Castellan’s Journey with Skyline

In this powerful first part of a two-part conversation, Dwayne Kerrigan sits down with longtime friend and business leader Jason Castellan, Co-Founder & CEO of Skyline Group of Companies.

Jason shares how growing up in small-town Walkerton, Ontario, instilled humility, resilience, and a relentless work ethic that carried him from hockey rinks and hayfields to co-founding one of Canada’s most respected real estate investment firms.

From his first student rental at the University of Guelph to overseeing $9 billion in assets under management and 1,000 employees, Jason pulls back the curtain on what it really takes to scale a business: financing hacks, the importance of partnerships, knowing when to let go, and why trust and relationships are more valuable than capital.

This episode is a masterclass in grit, community-driven leadership, and building wealth with integrity.

Timestamps

00:00 – The myth of the straight path in business & near-bankruptcy moments

01:30 – Introducing Jason Castellan & Skyline’s $9B journey

04:00 – Lessons from Walkerton: humility, farming roots & mentorship

07:00 – Childhood, hockey dreams, and how sports shaped his competitiveness

13:00 – The first student rental at Guelph and early entrepreneurial lessons

15:30 – Scaling to 52 houses: financing, sweat equity & creative problem-solving

21:00 – Financing strategies: trust, relationships, and building a social network

27:00 – Building your own legend: why life outside business matters

30:00 – Person vs. story: what investors really buy

33:00 – Facing doubt, trust, and learning to scale through partnerships

39:00 – Business battles, resilience, and “one more round” perseverance

42:30 – Experience creates strategy: when to let go & hire experts

46:00 – Leveraging talent: how Skyline attracted top-tier leaders

50:00 – Roadshows, raising capital & building Skyline’s REIT structure

55:00 – Closing thoughts: responsibility, growth, and investor trust

Notable Quotes

• “Build your legend. Be more than just a businessperson—have stories, have character, have a life that’s interesting to share.” – Jason Castellan
• “Face-to-face relationships are the currency of real estate—and of business.” – Jason Castellan
• “I wouldn’t have a fraction of what I have today if it wasn’t for partners.” – Jason Castellan

Resources & Mentions

• Skyline Group of Companies → Skyline
• Skyline Apartment REIT → Learn more
• Skyline Industrial REIT → Learn more
• Skyline Retail REIT → Learn more
• Skyline Clean Energy Fund → Learn more

Key Takeaways

1. Business is never a straight line – resilience and adaptability are everything.
2. Partnerships can multiply success – sweat + equity =...