What's Working Podcast

“For people who might not know you, can you give us a brief intro?”

This is a standard opening to establish the guest's background and credibility for the audience.

“What was your personal journey to becoming a founder in this space?”

The hosts often ask about the transition from prior roles (like corporate jobs) to entrepreneurship.

“What was the key factor that drove your rapid growth?”

A core question to uncover the 'secret sauce' or primary lever behind a guest's success.

“What's your framework for evaluating a new market or business opportunity?”

This question seeks to extract a repeatable process for strategic decision-making.

“What's a common mistake you see founders making in your space?”

This question surfaces common pitfalls and provides actionable advice for the audience.

“Can you walk us through the thinking behind a recent major business decision?”

Used to understand the strategic rationale behind significant pivots, like pulling sponsors or changing markets.

“Can you tell the story behind a specific marketing tactic or stunt that worked?”

Drills down into a single, memorable campaign to understand its execution and impact.

“How did you allocate the capital you raised?”

A direct question about capital allocation, usually asked of guests who have recently fundraised.

“Who else in the industry do you think is executing well right now?”

This question helps map the competitive landscape and identify other best-in-class operators.

“What's the biggest external risk or bear case for your business model?”

The hosts use this to pressure-test the guest's business and explore potential vulnerabilities.

“You've made some provocative statements online. What's the story behind that?”

A technique to broach controversial topics by referencing a guest's social media presence.

“Who are the founders or companies you look up to for inspiration?”

This question reveals the guest's influences and sources of inspiration.