Invest Like The Best

“What is the kindest thing that anyone's ever done for you?”

This is his signature closing question, asked in every interview to surface a personal story of gratitude.

“What's the origin story of you getting involved with [company/field]?”

He often opens with this to ground the listener in the guest's personal and professional history.

“What did it feel like on day one when you arrived at [company]?”

This question is used to capture the initial state and emotional texture of a major career transition or turnaround.

“What is the central strategic question you're focused on today as a leader?”

He asks this mid-interview to shift the focus from the past to the company's present and future challenges.

“What's your premortem for this opportunity? What has to go wrong for it to fail?”

This question probes for risks and the bear case, especially after a guest outlines a bullish thesis.

“How does your personal history or mindset shape your professional work?”

He frequently links a guest's background, like an immigrant story or a personal philosophy, to their business strategy.

“What have you learned about managing your own stress or psychology in a chaotic situation?”

This question explores the personal resilience and mental models required for high-stakes leadership.

“If I shadowed you for a week, what would I learn about how you operate?”

A unique question that asks for self-reflection on one's own daily principles and habits.

“Can you describe your framework for [investing, capital allocation, etc.]?”

A core question used to deconstruct the guest's repeatable process for making key decisions.

“What has to be true for your company to win in [a future market, e.g., AVs]?”

He asks this to understand the key variables and dependencies for a long-term strategic bet.

“What did you learn from your mentor [e.g., Barry Diller]?”

This question seeks to uncover foundational lessons from influential figures in the guest's life.

“What have you learned about the craft of [e.g., marketing, research] as your business has evolved?”

This question focuses on the evolution of a specific business function or skill.