The Dwayne Kerrigan Podcast 103. Beyond Billions: Jason Castellan on Leadership, Legacy, and Canada’s Future
In Part 2 of his inspiring conversation with Dwayne Kerrigan, Jason Castellan, Co-Founder & CEO of Skyline Group of Companies, goes beyond the growth story to share his philosophy on leadership, risk, and building a multi-generational business.
Jason opens up about succession planning, why staying people-focused is Skyline’s greatest advantage, and how he balances growth with responsibility to over 1,000 employees and 6,000 investors. He also provides candid insights on Canada’s economic headwinds, the housing crisis, energy infrastructure, and the future of clean energy.
This episode is not just about real estate—it’s about resilience, responsibility, and redefining what it means to lead with integrity.
Timestamps
00:00 – Believing in yourself & taking risks when young
01:30 – What separates Skyline from its peers
05:00 – Succession, leadership, and the “piss and vinegar” test
09:00 – Building a multi-generational business
13:30 – The obligation of leading thousands of employees and investors
16:00 – Canada’s economic headwinds & the housing affordability crisis
20:00 – Lessons from the U.S. & why Canada needs a wake-up call
23:00 – Bureaucracy, red tape, and the need for real solutions in housing
29:00 – AI, energy demand, and Skyline’s role in future infrastructure
33:00 – Solar, biogas, and battery storage as scalable solutions
39:00 – Evaluating risk: from speculation to disciplined growth
44:00 – Advice to young entrepreneurs on risk-taking
46:00 – Staying grounded: Jason’s unchanging values despite growth
49:00 – The power of face-to-face relationships in a digital-first world
50:00 – Closing reflections on legacy, integrity, and inspiring the next generation
Notable Quotes
- “When you lose your piss and vinegar, get out of the way.” – advice Jason received from a mentor
- “We gave up on saying we’re in the bricks and mortar business a long time ago. We’re in the people business.” – Jason Castellan
- “Take all the risk when you’re young. At 21, you can recover. At 65, you may not.” – Jason Castellan
- “It takes 25 years to build a reputation and 25 minutes to lose it.” – Jason Castellan
- “Face-to-face bonds are stickier and last longer than any digital connection.” – 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
- Leadership evolves, values don’t – stay true to your integrity as the business grows.
- Succession is not retirement – restructure roles but never retire from purpose.
- People are the business – investors, employees, and community matter more than assets.
- Face-to-face relationships still win – especially in an increasingly digital world.
- Canada must wake up – red tape, underutilized resources, and lack of competitiveness are holding the country back.
- Energy is the next frontier – scalable solutions like solar, biogas, and battery storage are key to powering AI and future growth.
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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.