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

1. Leadership evolves, values don’t – stay true to your integrity as the business grows.
2. Succession is not retirement – restructure roles but never retire from purpose.
3. People are the business – investors, employees, and community matter more than assets.
4. Face-to-face relationships still...