#855 Hard Questions, Easy Business

Most founders already know what's wrong with their business. The fix is usually simple but scary. So instead of doing the one hard thing that would make everything else easier, they stay busy. It feels like progress. It isn't. In this episode, Dan walks through the 7 questions he uses in $1,000/hour coaching calls — the ones that make the real problem impossible to ignore. And he shows you how to run the same audit on your own business using AI as your thinking partner. In this episode: • The simple but scary problems that show up in almost every business • Why most founders are spending money on 'hopeful outcomes' — and how to stop • The pricing question that reveals whether you actually believe in what you're selling • How to use AI as a founder (hint: context first, questions second) • What does your answer to 'how would you 2x in 90 days?' reveal about your business Resources mentioned: The 7-Question Business Audit The Complete Business Diagnostic More Business Resources Upcoming DC Events Tropical MBA is a podcast for entrepreneurs building location-independent businesses.

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#855 Hard Questions, Easy Business is an episode from The Tropical MBA Podcast - Entrepreneurship, Travel, and Lifestyle by Dan Andrews; Ian Schoen.

This episode is 26:30 long.

This episode was published on Apr 23, 2026.

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