THE FLIP SIDE w/Andy Mai

“How did you know you wanted to become a [profession]?”

He often asks this early on to understand the guest's core passion and origin story.

“How long have you been running this [business/store]?”

A standard opening question to establish the timeline and history of the guest's venture.

“What was your [career/role] before this, and did you transition any skills?”

This question helps connect the guest's past experiences to their current success.

“Why are [your product/service] so expensive?”

A direct question used to demystify the costs and value behind a guest's business.

“How did you go about monetization for [your company]?”

This question targets the specifics of the guest's business model.

“What was the reason for [major business decision, e.g., going public]?”

Used to uncover the strategic thinking behind significant company milestones.

“What happens to [your product] after [an event]?”

A curiosity-driven question about the lifecycle or waste stream of a product.

“What makes a [profession] a good [profession]?”

He asks this to distill the key skills and mindset required for excellence in the guest's field.

“How do you balance marketing for [customer segment A] versus [customer segment B]?”

Aimed at guests with two-sided marketplaces to understand their growth strategy.

“What's your advice for someone starting in [field] without a budget?”

This seeks to provide actionable, low-cost advice for the entrepreneurial audience.

“What are your thoughts on the new era of [industry trend, e.g., short-form content]?”

He poses this to get an expert's take on current and future industry shifts.

“How do you handle the stress of [a specific business pressure]?”

This question explores the personal and psychological challenges of entrepreneurship.

“How do you balance the stress of managing people with your personal life?”

Aimed at leaders, this question delves into their work-life philosophy.

“What's happening right now?”

Asked during on-location interviews to get a real-time explanation of the guest's creative or technical process.

“What's the last thing you've added to your daily routine?”

A signature closing question to get a personal, non-business insight.

“Over the next six months, any goals that aren't work-related?”

A favorite closing question to understand the guest's personal priorities and life outside of work.