Interview questions Jon is ready to dig into. Copy them, tweak them, or bring your own.
1What do most business owners misunderstand about preparing for an exit—and when should that preparation actually start?
2Can you walk us through the mindset shift an owner needs to make when moving from growth to exit planning?
3You work with a lot of founders in the 5–10 year phase—what’s unique about that stage, and why do so many get stuck there?
4How can a business owner tell if they’re “lender-ready”? What red flags do banks or investors look out for?
5What’s the difference between building a profitable business and building a business that someone else would want to buy?
6You talk about legacy not just as a financial outcome but as an emotional journey. What does that look like in practice?
7What are some of the biggest financial blind spots you see in business owners who come to you for help with raising capital?
8How do you help business owners who are emotionally attached to their company begin to think about life after ownership?
9What practical steps can an owner take today to reduce burnout and step back from the day-to-day without losing control?
10You’ve worked in banking, real estate, and now coaching—how has your own career journey shaped the way you guide clients through transitions?