Every M&A practitioner has a deal that still makes them wince. This episode collects the ones that never make it into a case study.

Kison pulled real stories from corporate development leaders, bankers, attorneys, and advisors, names removed, about the deals that died at the finish line, fell apart after close, or came back from the brink. A spouse's background check two weeks from signing. A buyer's plane crash nine months into a process. A CFO who had been quietly draining company funds for years and fled the country before the ink dried.

Some of these deals closed anyway and became the best outcomes of the storytellers' careers. Others walked away from life-changing paydays over disagreements that, in hindsight, should have been let go. The throughline: a surprise late in a process costs more than the same surprise caught early, and the deals that survive are usually the ones where someone caught the problem before the wire went out.

What You'll Learn

Run background checks on day one, not day seven. A spouse's background check two weeks from close killed a deal already through diligence. Building it into the NDA stage surfaces the problem months earlier.
Put IP and royalty terms in the LOI, not just the term sheet. A divestiture nearly broke down near signing because retained-IP rights were never spelled out early, and the late surprise cost more trust than money.
Treat a founder family on the cap table as its own risk factor. Co-founder splits, sibling ownership disputes, and misaligned family incentives have killed deals that looked clean on paper.
Don't let a one-to-two point retrade blow up months of work. One PE fund lost a near-certain win by reopening valuation a week before signing. The sellers walked, and the asset went on to outperform under a different buyer.
Verify the forecast you're buying is the real one. A team that skipped verifying a target's internal numbers found out the hard way, the morning after wiring the money.
Build bankruptcy-specific terms into every auction timeline. A court-supervised sale can still be gazumped by a new bidder until the judge formally enters the sale order.
Expect culture, not price, to be the real deal killer. Several of the costliest blowups here had nothing to do with valuation and everything to do with who stays, who leaves, and how integration actually gets run.

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