The Dwayne Kerrigan Podcast 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
- Business is never a straight line – resilience and adaptability are everything.
- Partnerships can multiply success – sweat + equity = scale.
- Stay interesting – your life outside business helps you connect and build relationships.
- Leverage talent – bringing in experts early allows sustainable growth.
- Resilience is learned – like hockey, business teaches you to get over losses quickly and move on.
Connect with Dwayne Kerrigan
Disclaimer: The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.