Red Flags in an M&A Offer You Should Never Ignore

By M&A Advisory
28 Aug 2025

Not all offers are created equal.

๐‘จ ๐’‰๐’Š๐’ˆ๐’‰ ๐’๐’–๐’Ž๐’ƒ๐’†๐’“ ๐’๐’ ๐’‘๐’‚๐’‘๐’†๐’“ ๐’…๐’๐’†๐’”๐’’๐’• ๐’‚๐’๐’˜๐’‚๐’š๐’” ๐’Ž๐’†๐’‚๐’ ๐’Š๐’•’๐’” ๐’•๐’‰๐’† ๐’“๐’Š๐’ˆ๐’‰๐’• ๐’…๐’†๐’‚๐’ ๐’๐’“ ๐’‚ ๐’”๐’‚๐’‡๐’† ๐’๐’๐’†.

Here are 7 M&A offer red flags we see far too often in the Marcomms and Martech world ๐Ÿ‘‡

1๏ธโƒฃ ๐ƒ๐ž๐Ÿ๐ž๐ซ๐ซ๐ž๐ ๐‚๐จ๐ง๐ฌ๐ข๐๐ž๐ซ๐š๐ญ๐ข๐จ๐ง ๐ฐ๐ข๐ญ๐ก ๐๐จ ๐‚๐ฅ๐š๐ซ๐ข๐ญ๐ฒ
If considerable value is tied to future “earn-outs” or milestones with no transparency, proceed cautiously.

2๏ธโƒฃ ๐„๐ฑ๐œ๐ž๐ฌ๐ฌ๐ข๐ฏ๐ž ๐ƒ๐ฎ๐ž ๐ƒ๐ข๐ฅ๐ข๐ ๐ž๐ง๐œ๐ž ๐‘๐ž๐ช๐ฎ๐ž๐ฌ๐ญ๐ฌ ๐๐จ๐ฌ๐ญ-๐Ž๐Ÿ๐Ÿ๐ž๐ซ
If due diligence starts after heads of terms but suddenly expands into a fishing expedition, they may be stalling or not serious.
 
3๏ธโƒฃ “๐•๐š๐ฅ๐ฎ๐š๐ญ๐ข๐จ๐ง” ๐“๐ก๐š๐ญ ๐ˆ๐ ๐ง๐จ๐ซ๐ž๐ฌ ๐‚๐จ๐ฆ๐ฆ๐ž๐ซ๐œ๐ข๐š๐ฅ ๐‘๐ž๐š๐ฅ๐ข๐ญ๐ฒ
Beware inflated offers built on unrealistic multiples of unrepeatable EBITDA or “potential.”
๐‘บ๐’†๐’๐’”๐’Š๐’ƒ๐’๐’† ๐’ƒ๐’–๐’š๐’†๐’“๐’” ๐’—๐’‚๐’๐’–๐’† ๐’”๐’–๐’”๐’•๐’‚๐’Š๐’๐’‚๐’ƒ๐’Š๐’๐’Š๐’•๐’š, ๐’๐’๐’• ๐’‹๐’–๐’”๐’• ๐’”๐’„๐’‚๐’๐’†.
 
4๏ธโƒฃ ๐๐จ ๐‚๐จ๐ฆ๐ฆ๐ข๐ญ๐ฆ๐ž๐ง๐ญ ๐ญ๐จ ๐˜๐จ๐ฎ๐ซ ๐“๐ž๐š๐ฆ ๐จ๐ซ ๐‚๐ฎ๐ฅ๐ญ๐ฎ๐ซ๐ž
Expect turbulence post-deal if there’s zero mention of staff, values, or culture in the buyer’s vision.
๐‘ท๐’†๐’๐’‘๐’๐’† ๐’‚๐’“๐’† ๐’š๐’๐’–๐’“ ๐’‚๐’ˆ๐’†๐’๐’„๐’š. ๐‘ฉ๐’–๐’š๐’†๐’“๐’” ๐’”๐’‰๐’๐’–๐’๐’… ๐’Œ๐’๐’๐’˜ ๐’•๐’‰๐’‚๐’•.

5๏ธโƒฃ ๐”๐ง๐ฎ๐ฌ๐ฎ๐š๐ฅ ๐ƒ๐ž๐š๐ฅ ๐’๐ญ๐ซ๐ฎ๐œ๐ญ๐ฎ๐ซ๐ž๐ฌ ๐จ๐ซ “๐‚๐ซ๐ž๐š๐ญ๐ข๐ฏ๐ž” ๐„๐š๐ซ๐ง-๐Ž๐ฎ๐ญ๐ฌ
 Overcomplicated structures often hide risks or mask gaps in funding.
 ๐‘บ๐’Š๐’Ž๐’‘๐’๐’Š๐’„๐’Š๐’•๐’š ๐’‘๐’“๐’๐’•๐’†๐’„๐’•๐’” ๐’—๐’‚๐’๐’–๐’†. ๐‘ช๐’๐’Ž๐’‘๐’๐’†๐’™๐’Š๐’•๐’š ๐’๐’‡๐’•๐’†๐’ ๐’†๐’“๐’๐’…๐’†๐’” ๐’Š๐’•.
 
6๏ธโƒฃ ๐๐ซ๐ž๐ฌ๐ฌ๐ฎ๐ซ๐ž ๐ญ๐จ ๐’๐ข๐ ๐ง ๐๐ฎ๐ข๐œ๐ค๐ฅ๐ฒ
Artificial urgency is a red flag, especially if combined with vague terms.
 
7๏ธโƒฃ ๐“๐ก๐ž๐ฒ ๐“๐š๐ฅ๐ค. ๐๐ฎ๐ญ ๐ƒ๐จ๐ง’๐ญ ๐‹๐ข๐ฌ๐ญ๐ž๐ง
If the buyer talks at you, not with you, they likely haven’t grasped your true value.
๐‘จ ๐’ˆ๐’“๐’†๐’‚๐’• ๐’…๐’†๐’‚๐’ ๐’”๐’•๐’‚๐’“๐’•๐’” ๐’˜๐’Š๐’•๐’‰ ๐’‚ ๐’ˆ๐’“๐’†๐’‚๐’• ๐’…๐’Š๐’‚๐’๐’๐’ˆ๐’–๐’†. 

๐Ÿ’ฌ ๐“๐ก๐ข๐ง๐ค๐ข๐ง๐  ๐š๐›๐จ๐ฎ๐ญ ๐š ๐ฌ๐š๐ฅ๐ž? ๐†๐จ๐ญ ๐š๐ง ๐จ๐Ÿ๐Ÿ๐ž๐ซ ๐จ๐ง ๐ญ๐ก๐ž ๐ญ๐š๐›๐ฅ๐ž?
 Before you say yes, let’s pressure-test it.
 We’ve seen every structure, every buyer, every trick in the book.

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