Most founders spend twenty years building their business and about twenty minutes preparing to sell it.

The result? Millions left on the table. Bad deals. Regret. And in too many cases, starting all over again when they should be retired.

Jonathan Sherrill has been on every side of a business exit. He helped his father sell. He ran a company for private equity. He built his own company from scratch and sold it for twice what he expected. And then he wrote a book about all of it called The Extraordinary Exit.

In this episode of CEOs Unscripted, Jonathan sits down with Jane Gentry to share the unfiltered truth about what it really takes to get an extraordinary exit, and why most founders are completely unprepared for what comes after.

Key Topics Covered:

• The critical difference between building a company for income and building one for wealth
• The full advisory team you need before going to market and why most founders skip half of them
• Why the emotional preparation for selling is just as important as the financial preparation
• What happens when an unsolicited buyer approaches you and why it almost never ends well
• The seven levels of why exercise that reveals the real reason founders want to sell
• Why ego and pride destroy more deals than bad financials ever will
• What to do if your deal falls apart and why it is not the end of the story
• How to know if you are emotionally ready to sell before you ever go to market

📌 Episode Timestamps:

• 00:00 — Cold open: I had no idea you could sell a company for a multiple until I lived through it
• 00:55 — Welcome to CEOs Unscripted
• 02:35 — Meet Jonathan Sherrill, author of The Extraordinary Exit and founder of Waypoint Founders
• 03:15 — Jonathan’s backstory: small town Florida, metal roofing, private equity and his own exit
• 04:38 — What was different about the second exit vs the first
• 05:06 — Learning the exit world from the inside out while working for private equity
• 06:33 — Building a company from day one with the intention to sell it
• 08:16 — Building for income vs building for wealth, the trap most founders fall into
• 09:22 — Why being too important to your own business will kill your deal
• 09:55 — The full advisory team you need before going to market
• 13:18 — Who is the quarterback of the deal and why it matters
• 14:52 — What Jonathan did differently the second time around
• 16:19 — Why bad advisors cost founders millions and how to avoid them
• 18:50 — Do not wait until you are exhausted to start preparing to sell
• 19:11 — The stat that should scare every founder: most are unhappy within 18 months of selling
• 21:09 — The exit why exercise and why your first answer is probably not the real reason
• 23:32 — The emotional void that hits after a great exit and why founders are not prepared for it
• 25:07 — How the book The Extraordinary Exit came to be
• 27:26 — What Waypoint Founders actually does and who it is for
• 30:56 — The seven levels of why exercise explained
• 33:49 — Why learning from other founders is the whole point
• 35:09 — Do not let a friend who sold one company be your only advisor
• 36:43 — What makes deals fall apart and what you can do about it
• 38:24 — If you are not coachable do not waste money on great advisors
• 39:56 — How ego and pride destroy deals worth tens of millions of dollars
• 41:19 — It takes ego to build a company, just do not let it be your downfall at exit
• 42:18 — The exit readiness assessment on the Waypoint Founders website
• 44:10 — How to connect with Jonathan Sherrill and get the book
• 44:44 — The unsolicited buyer trap and why it almost never ends in your favour
• 46:26 — What Jane has seen happen to founders who got bad advice
• 47:52 — Jonathan’s closing thoughts on what he genuinely cares about
• 48:09 — Jane’s closing thoughts

🎙️ About CEOs Unscripted:

CEOs Unscripted is a bi-weekly podcast for mid-market CEOs, no fluff, no jargon, just real conversations from leaders who have been in the trenches.