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.

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 → https://www.skylinegroupofcompanies.ca/

Key Takeaways
1. Business is never a straight line – resilience and adaptability are everything.
2. Partnerships can multiply success – sweat + equity = scale.
3. Stay interesting – your life outside business helps you connect and build relationships.
4. Leverage talent – bringing in experts early allows sustainable growth.
5. Resilience is learned – like hockey, business teaches you to get over losses quickly and move on.

Connect with Dwayne Kerrigan
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Linked In: https://www.linkedin.com/in/dwayne-kerrigan-998113281/
Website: http://www.dwaynekerrigan.com

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.