Interview Questions
10+ Questions to Ask Andrew Hathaway
Curated by PodPrepper's AI from real podcast prep sessions. Each question is scored on a viral-hook scale of 1-10. higher scores predict clip-worthy moments. Sample below; sign up free to generate the full brief for Andrew Hathaway or any guest.
Sample questions
#1
9.0
You've publicly talked about having a mental breakdown six years into your first business. Walk me through what was actually happening behind the scenes during that stretch.
General Questions
#2
9.0
You shut down your first business to start Virtual Assist. Most founders white-knuckle a dying business instead of killing it. What should a listener look for to know it's time to pull the plug and pivot?
General Questions
#3
9.0
Here's an unpopular opinion. You disagree that the blue-collar space is safe from disruption. Walk me through where robots and AI are about to gut jobs that blue-collar workers think are untouchable.
General Questions
#4
9.0
Which business guru do you think is completely overrated?
Lightning Round
#5
9.0
This one's a little spicy. You recently partnered with a larger organization to scale faster, which you say most business owners refuse to do. Walk me through why founders resist giving up control and what that partnership actually looks like in practice.
#6
9.0
You've interviewed real estate investors, CPG founders, and estate planning attorneys on your podcasts. Give me the name of one guest whose specific strategy you actually took and implemented in your own business, and what it did for your numbers.
#7
9.0
You publicly said your business gave you a mental breakdown after six years. Walk me through what was actually happening week to week during the worst of it, and what finally broke the cycle.
#8
9.0
Which business guru do you think is completely overrated?
6 more questions
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Generate my first brief freeHow these questions are scored
Every question on this page was generated by PodPrepper, an AI tool built specifically for podcast hosts who interview guests. The scoring system uses a viral-pattern model trained on 5,000+ top-performing creator posts to predict which questions will produce clip-worthy moments. the kind that get pulled into reels, shared on social, and drive new listeners.
A score of 9.0+ means the question hits multiple viral hooks: contradiction, contrarian framing, lesson extraction, vulnerability, or specific-numbers anchoring. These are the questions worth building an interview around.
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