In this episode of Inside the Rope, David Clark sits down with Chris Aylward, a veteran of Australian property markets whose career spans more than five decades. From leasing office towers in Melbourne in the 1970s to founding APN Property Group and navigating multiple financial crises, Chris has seen every phase of the real estate cycle.

For investors trying to make sense of today’s market - rising rates, expensive assets, private credit growth and uncertainty around office property, Chris offers a rare long-term perspective.

This conversation explores what today’s market gets right, what it gets dangerously wrong, and why experienced investors are becoming more cautious even while liquidity floods into property and private debt.

Chris also reflects candidly on the biggest mistake of his career - a European property fund that went badly wrong, and the lessons it taught him about partnerships, leverage and risk management.

For listeners managing wealth, allocating capital, or investing in real assets, this episode is a great learning episode in cycle awareness and disciplined investing.

If you’ve recently had a liquidity event, inherited complexity, or are quietly wondering whether your portfolio is truly built for the next 30 years — this episode is essential listening.

In this conversation, Ian Macoun, founder of Pinnacle Investment Management, joins David Clark to unpack what actually drives sustained investment excellence — and what quietly destroys it.

With over $200 billion under management across 19 affiliates, Pinnacle has become one of Australia’s most successful multi-affiliate investment firms. But this episode is not about scale. It’s about structure, incentives, character, and long-term alignment.

For sophisticated investors managing significant capital, this discussion goes directly to the hard questions:

• Why do some fund managers endure for decades while others fade?
  

• How do you distinguish confidence from dangerous ego?
  

• Is private credit a structural allocation, or the next bubble?
  

• How should wealthy operators think differently about portfolio construction?
  

• What does AI mean for growth investing?
  

• Where are private markets heading next?

Ian’s philosophy is simple but demanding: excellence is the only standard.

And that applies to both managers and investors.

Inside The Rope's episode with Ian Macoun will release next Tuesday, the 3rd of March 2026.