#855 Hard Questions, Easy Business
Tropical MBA: Entrepreneurship & Founder Lifestyle
Dan Andrews; Ian Schoen
4.9 • 527 Ratings
🗓️ 23 April 2026
⏱️ 27 minutes
🧾️ Download transcript
Summary
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
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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 Dan@tropicalmba.com
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Transcript
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| 0:00.0 | Happy Thursday morning, everybody. Welcome back to the Tropical MBA podcast. We're doing this thing one-on-one today. I want to share with you just a thought process, |
| 0:22.3 | a opportunity that was inspired by an experience I had a few weeks ago. I'm going to share |
| 0:28.1 | seven questions that you can bring to your AI friend of choice to help you face down and |
| 0:35.0 | identify the next big opportunity in your business. |
| 0:38.9 | I feel like the vibe online in business opportunity space is that, you know, |
| 0:44.8 | opportunities are easy. |
| 0:46.0 | They're everywhere. |
| 0:46.9 | Keep doing stuff. |
| 0:47.9 | Good stuff happens. |
| 0:49.5 | But in real life, what I often find is that opportunities exist on the opposite side of one challenging |
| 0:56.5 | decision. And often, that challenging decision involves overcoming a fear. That's kind of strange. |
| 1:05.2 | Why is that strange? Because maybe there's a structural element to it. Like, why would you have to |
| 1:09.5 | overcome a fear to have a successful business? |
| 1:13.0 | It's because you're doing things that other people aren't doing. Like, it's sort of a relative thing. |
| 1:18.8 | Like, if you just simply take it as it comes, then you'll get average results. So we're seeking |
| 1:26.0 | asymmetrical results. We're seeking unique results, |
| 1:31.2 | and therefore there's often something that we have to do, even launching a new product, |
| 1:35.9 | declaring yourself responsible for X set of outcomes, being confident about the results your product |
| 1:43.6 | can deliver for a target market. These are not |
| 1:46.4 | normal things. These are things that require overcoming a fear of judgment, a fear of what |
| 1:53.0 | other people will think, a fear of doing the wrong thing. The vibe online will often say that |
| 1:58.8 | starting a business, you just go out, you do X, Y, and Z. |
... |
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