Most deals in the $1M–$50M range don’t fall apart because of one major issue.
They fall apart because of timing, structure, and alignment.
In my experience, there are three common pressure points:
1. Financing Uncertainty Shows Up Late
Deals look solid—until underwriting starts asking harder questions.
At that point:
- timelines stretch
- terms shift
- or the deal needs to be re-traded
The earlier financing is taken seriously, the smoother everything else becomes.
2. Key Terms Aren’t Fully Worked Through in the LOI
The LOI gets signed quickly (which is often the goal).
But if it doesn’t anticipate:
- working capital structure
- indemnification approach
- seller involvement post-close
…those issues don’t go away—they just show up later, with more friction.
3. Third Parties Get Engaged Too Late
Landlords, lenders, key customers—these can all slow a deal down.
The deals that move cleanly usually have:
- early communication
- realistic expectations
- and coordination across all parties
Where Legal Actually Adds Value
In this deal size range, legal isn’t just about documenting the transaction.
It’s about:
- identifying issues early
- keeping momentum
- and helping parties stay aligned when things get tight
If you’re navigating a deal in this range, you can learn more about how I approach M&A transactions here.