102. From Small-Town Roots to $9 Billion in Assets: Jason Castellan’s Journey with Skyline
102. From Small-Town Roots to $9 Billion in Assets: Jason Castellan’s Journey with Skyline  
Podcast: The Dwayne Kerrigan Podcast
Published On: Wed Aug 27 2025
Description: 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.Timestamps00:00 – The myth of the straight path in business & near-bankruptcy moments01:30 – Introducing Jason Castellan & Skyline’s $9B journey04:00 – Lessons from Walkerton: humility, farming roots & mentorship07:00 – Childhood, hockey dreams, and how sports shaped his competitiveness13:00 – The first student rental at Guelph and early entrepreneurial lessons15:30 – Scaling to 52 houses: financing, sweat equity & creative problem-solving21:00 – Financing strategies: trust, relationships, and building a social network27:00 – Building your own legend: why life outside business matters30:00 – Person vs. story: what investors really buy33:00 – Facing doubt, trust, and learning to scale through partnerships39:00 – Business battles, resilience, and “one more round” perseverance42:30 – Experience creates strategy: when to let go & hire experts46:00 – Leveraging talent: how Skyline attracted top-tier leaders50:00 – Roadshows, raising capital & building Skyline’s REIT structure55:00 – Closing thoughts: responsibility, growth, and investor trustNotable 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 CastellanResources & MentionsSkyline Group of Companies → SkylineSkyline Apartment REIT → Learn moreSkyline Industrial REIT → Learn moreSkyline Retail REIT → Learn moreSkyline Clean Energy Fund → Learn moreKey TakeawaysBusiness 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 KerriganFacebookInstagramLinked InWebsiteDisclaimer: 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.