What Buyers Are Actually Looking For with Jonathan Sherrill of Waypoint and “The Extraordinary Exit”

Jonathan Sherrill, Founder of Waypoint, built Quicken Steel from a shuttered sawmill and sold it in 2022. He explains what buyers really test for before they buy.

He co-authored “The Extraordinary Exit” with Andy Harris; the book won the Gold Medal for Best Adult Non-Fiction Informational eBook at the 2026 IPPY Awards. Through Waypoint, Jonathan advises founders on the personal side of the exit.

Key Takeaways:

00:00 Introduction 03:31 What six years working for private equity taught him about what buyers really want 13:14 Why his daughter's diagnosis changed what he was building his company for 19:31 The test buyers quietly run before they'll ever make an offer 20:23 A flat tire question that reveals whether a business can run without its founder 24:33 The leadership team question most CEOs would rather not answer honestly 28:02 Why a coach who pushes back beats an advisor who just agrees 34:51 The charitable commitment that nearly delayed a multi-million dollar closing 37:17 What it actually felt like when the emails and calls just stopped 45:43 His advice for any founder still carrying self-doubt

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Resources Mentioned:

Waypoint website: https://waypointfounders.com/

“The Extraordinary Exit” by Andy Harris and Jonathan Sherrill: https://www.theextraordinaryexitbook.com/

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