No Cap by CRE Daily

“What's your origin story? How did you get into the business?”

This is the standard opening question, used to frame the guest's entire career arc before diving into specifics.

“What was the investment thesis when you first started the company?”

They ask this to understand the firm's foundational strategy and how it may have evolved.

“How much of real estate is just timing?”

A philosophical question used to explore the role of luck versus skill in a guest's success.

“Who were your first investors when you started raising capital?”

This question surfaces the practical realities of getting a new real estate venture off the ground.

“How are you capitalizing your deals right now?”

A direct question to understand the guest's current approach to the capital stack (debt, pref, common equity).

“What are the theses and spots you're excited about right now?”

A go-to question to get the guest's current, actionable view on specific markets or asset classes.

“Why did you choose to invest in [City/State] specifically?”

Probes the market selection strategy behind a guest's portfolio or a specific deal.

“What are the parallels between today's market and the 2008 GFC?”

Used with veteran guests to draw historical comparisons and gauge their current level of concern or optimism.

“Do you have a war story from a particular property or deal?”

This question is designed to elicit a specific, memorable anecdote that reveals the guest's problem-solving style.

“How has the business changed since you started?”

This prompts a high-level reflection on industry evolution from a long-tenured guest.

“What was the inflection point for your company's success?”

Focuses on the key decisions or market events that led to significant growth.

“Why should someone use your product instead of just using [common alternative]?”

A direct challenge to proptech founders to clarify their unique value proposition.