#281 The Worst Acquisition I Ever Did and What It Cost Me, Jeremy Earnshaw, GrowCFO Mentor

#281 The Worst Acquisition I Ever Did and What It Cost Me, Jeremy Earnshaw, GrowCFO Mentor

From GrowCFO Show by Kevin Appleby

April 28, 2026 · 39 min

About this episode

Jeremy Earnshaw discusses a failed acquisition and the lessons learned from it.

https://open.spotify.com/episode/55cBmmBgaKb7MGUsUgPtNT In this GrowCFO Show episode, Kevin Appleby sits down with Jeremy Earnshaw , GrowCFO Mentor, to unpack one of the most painful but instructive topics in corporate life. Rather than celebrating a headline-grabbing success, Jeremy walks through a deal that went badly wrong—financially, culturally, and strategically. The episode emphasizes why leaders often learn far more from failures than from smooth, textbook transactions, and why understanding what not to do in M&A can be a powerful competitive advantage.  Drawing on more than 20 M&A deals across his career, Jeremy dissects an acquisition from 30 years ago where he joined mid-transaction, found due diligence to be dangerously superficial, and discovered too late that the target’s core direct-to-consumer channel was fundamentally unprofitable. He and Kevin explore how poor diligence, misaligned incentives, cultural blind spots, and weak integration planning combined to destroy value. The conversation offers CFOs, founders, and boards a candid look at the real costs of a bad acquisition and practical lessons on how to structure deals, probe assumptions, and…

People in this episode

Host: Kevin Appleby

Guest: Jeremy Earnshaw

Topics covered

  • acquisition failures
  • M&A lessons
  • due diligence
  • corporate culture
  • financial strategy
  • leadership insights

Keywords

  • acquisition
  • M&A
  • due diligence
  • corporate culture
  • financial loss
  • leadership
  • business strategy

Mentioned in this episode

Organizations: GrowCFO

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