Red Flags
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In DD, ‘red flags’ can be visible, but are often rationalised away.
Why are early warning signs often reframed as ‘integration issues’ or ‘execution risk’? Are there any ‘red flags’ that should be automatic deal‑breakers?I think it’s pretty natural—once people are already interested or invested, they tend to downplay problems and convince themselves things can be fixed. Calling something “execution risk” sounds less scary than admitting it Infinite Craft might be a real deal-breaker. But honestly, things like lack of honesty, shady behavior, or big value mismatches are hard to fix and usually only get worse, so those should probably be taken seriously from the start.
Mainly because of bias and deal pressure. Once a deal has momentum, teams tend to reframe risks as “fixable” to keep it moving, especially if they believe they’ll have control post-acquisition.
There’s also a tendency to underestimate how structural some issues are—what looks like an execution problem can actually be embedded in the business model.
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