In my experience great advice can move across industries in several categories; cash flow management, human resources, process improvement, systems and measurement.

Ask him questions relating to how he measures, rewards and retains his best staff.
Ask about how he ensures proper cash flow management, how he extends payables for instance.
Ask about how he tracks the efforts of employees to know who is contributing to the bottom line and who is not.
Ask him how he knows when it's time to make changes in how things are done.
Ask him how he responded to the last new competitive threat.
Ask him how he plays a role in different aspects of his business; sales, purchasing, marketing, etc.

Good luck. Simply taking the time to put some thought into what you should be asking will help make this meeting into a great opportunity. Don't get too scripted though and ask him what he thinks you should learn about what he's been through.

Cheers
David C Barnett

I’m a finance and strategy professional with experience working with founders, CEOs and business owners on scaling, financial planning and operational decision-making.

When you meet a highly successful business owner, the goal isn’t to get generic financial advice, but to extract the principles and mental models behind how they make decisions. Great questions are specific, practical, and focused on their thinking, not their industry.

Here are strong, high-value questions you can ask:

1. Decision-making & strategy
• What has been your most reliable way to choose which opportunities to pursue — and which to ignore?
• What was the best long-term strategic decision you ever made, and why?
• If you were in my industry today, what would you focus on first?

2. Risk management & financial discipline
• How do you decide when to reinvest vs. when to take profit?
• What financial metrics do you watch weekly or monthly?
• What was your biggest financial mistake — and how did you correct it?

3. Growth & operations
• What systems or routines helped you scale without losing control?
• How do you build loyalty — with customers or employees?
• What bottleneck slowed your growth the most, and how did you solve it?

4. Personal lessons & mindset
• What habits contributed most to your financial success?
• What would you do differently if you were starting today?
• Who influenced your thinking the most — and why?

5. For actionable advice
• Given what you know about my business, what’s the one thing you would focus on for the next 90 days?
(This gives you the most concrete, relevant insight.)

For you the answer might be a little late but for everyone else in a similar situation, I can help you prepare the conversation so you walk in with a clear structure and get maximum value from the meeting — happy to discuss it briefly on a call.