#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. Subscribe for weekly episodes on business, money, and the entrepreneurial lifestyle. Hang out exclusively with 7+ figure founders in DC BLACK https://dynamitecircle.com/dc-black CHAPTERS (00:00:00) The local business story — same problems, every time (00:04:23) AI as a thinking partner — and why context is everything (00:07:30) Q1: What is the ROI on your biggest expenses? (00:11:22) Q2: Where did your last 10 customers come from? (00:12:43) Q3: If you had to raise prices 20% tomorrow, how would you? (00:14:15) Q4: Do you have a product your best customers can pay 3–10x more for? (00:14:35) Q5: Who owns which decisions — and is it written down? (00:16:38) Q6: What are you doing that isn't sales or delivery? (00:19:16) Q7: How would you 2x revenue in 90 days? (00:22:44) Bonus: What is your business actually worth? (00:23:49) Closing: The hard thing that makes everything else easier (00:24:41) Community & events: Mexico, Barcelona, Bangkok, New York CONNECT: Dan Andrews is the co-founder of Dynamite Circle, author of Before the Exit, host of the Tropical MBA podcast, and an entrepreneur who has successfully launched and scaled multiple 7-figure businesses. Email [email protected] PLAYLIST: The $10K Projects You Never Do (AI Just Changed That) How to Build a 6-Figure Digital Business with Claude Code We Got Claude-Pilled