Today we sit down with Mark Rolton, property developer, entrepreneur, and founder of Massland, one of Australia’s most successful property development companies. 

Known for his business acumen and no-fluff mindset, Mark goes deep in this conversation, opening up about his personal life, values, and philosophy in a way that most people haven’t seen.

This episode covers much more than business. It’s about parenting, legacy, masculinity, grief, and the reality of building true resilience. Mark shares raw, powerful stories that cut straight to the core of what it means to lead—both in business and at home.

From Chris:

This is honestly one of my favourite episodes to date. Mark’s calm, grounded nature combined with his perspective on parenting, growth, and loss really stuck with me. The topics we explored here are some of the most important and meaningful I’ve ever had on the podcast and I truly believe everyone can take something from this.

Key Discussion Points:

Enjoy and be sure to share this on your stories or to a friend who you think will love the show.

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Timestamps:

0:05 – Why Mark doesn’t share problems

0:11 – The tunnel analogy for challenge

0:16 – Business as a tool for growth

0:22 – Masculinity and personal development

0:27 – How over-giving harms kids

0:33 – Mark’s upbringing and money drive

0:38 – Starting in property with no capital

0:44 – Lessons from Keith Cunningham

0:49 – Wealth, values, and true success

0:55 – Losing his daughter

1:00 – Processing grief and finding purpose

1:06 – His approach to fatherhood today

1:11 – Raising sons vs. daughters

1:17 – Leadership, loneliness, and legacy

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