#281 The Worst Acquisition I Ever Did and What It Cost Me, Jeremy Earnshaw, GrowCFO Mentor
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 retain the courage to walk away.
Key topics covered:
- Jeremy explains how he joined an acquisition mid-stream and immediately saw that the “due diligence” was little more than an updated audit pack.
- Kevin and Jeremy break down why buying “a balance sheet” instead of a future business led to a badly structured deal, with 90% of the consideration paid in cash at completion.
- They expose how cultural issues, aggressive lawyers, and late negative disclosures undermined trust and should have been clear red flags to pause or walk away.
- Jeremy reveals that the acquisition’s main focus—the direct-to-consumer channel—was actually loss-making, while an overlooked export dealer channel was where the real profitability lay.
- The episode highlights how weak integration planning compounded the initial mistakes, turning a flawed deal into a value-destroying one.
- Jeremy distills the lessons learned: insist on thorough due diligence, structure earn-outs intelligently, interrogate culture and people risk, and always be prepared to walk away.
Links
Timestamps:
- 0:00:00 – Kevin frames the episode around learning from “the worst acquisition” and introduces Jeremy Earnshaw and his M&A background.
- 0:02:00 – Jeremy describes joining halfway through the deal and discovering that due diligence was basically a thin audit update.
- 0:06:23 – Deep dive into due diligence and valuation: why paying 90% cash up front and underweighting earn-out was a structural mistake.
- 0:19:35 – Cultural and legal challenges emerge: aggressive lawyers, late disclosures, and a finance controller’s resignation revealed just before completion.
- 0:24:35 – Post-acquisition reality check: the direct-to-consumer channel is loss-making while the neglected export dealer business is the only profitable part.
- 0:36:56 – Jeremy and Kevin synthesize the core lessons around diligence discipline, deal parameters, and the importance of being ready to walk away.
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