The Property Funder Podcast

“How did you get your start in specialist lending or property?”

This is a frequent opening question used to establish the guest's backstory and entry into the industry.

“What is [your company] and what was the origin story behind it?”

Used early in the conversation to understand the guest's current business and its founding principles.

“How did you find the transition from the [lender/broker] side to the other?”

He asks this to compare and contrast different roles and cultures within the property finance ecosystem.

“What does a typical [data center/prime renovation] deal actually look like?”

This question pushes past generalizations to get concrete details on specific, often niche, project types.

“What are the key differences between a successful and an unsuccessful project?”

This question seeks to extract practical, experience-based advice on development strategy.

“Where do people often go wrong when trying to [work with family offices/get funding]?”

Aimed at identifying common pitfalls and extracting actionable advice for the professional audience.

“What key advice are you giving to new people joining your team?”

This reveals the guest's management philosophy and the core principles they instill in their staff.

“What advice would you give to your younger self?”

This is the host's signature closing question, used across multiple episodes to end on a personal, reflective note.

“What's your view on [a contentious practice, e.g. brokers hiding clients from lenders]?”

Dean uses this to explore industry tensions and ethical gray areas, leveraging his insider status.

“How do you see the [broker/lending] landscape evolving in the next few years?”

A standard question to elicit forward-looking predictions and trend analysis from experts.

“Is [new technology, like AI] a threat or an opportunity for the industry?”

He asks this to gauge expert opinion on the impact of technological disruption on their field.

“What are the hot-button topics people are talking to you about right now?”

A way to take the pulse of the market and uncover current industry-wide concerns and opportunities.

“What's the smallest development loan you'd consider?”

A direct question to clarify a lender's specific appetite and lending parameters.