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November 29, 2025When Technical Oversights Become Deal-Breakers in M&A
Imagine discovering a $100,000 accounting error days after finalizing an acquisition. That’s how technical debt feels in M&A deals. After 12 years reviewing acquisition targets, I’ve seen how minor-seeming issues in code attribution systems can expose serious risks.
Take our coin grading case study: What looked like one mislabeled coin revealed systemic problems. In tech deals, these “small” errors often hide bigger issues – unreliable code, shaky operations, and cultural blind spots that tank valuations.
The Attribution Failure That Mirrors Technical Debt
A Real-World Wake-Up Call
That frustrating coin mix-up? It’s eerily similar to what I find in acquisition targets:
- Time capsule code: Systems relying on decade-old logic (like those outdated Cherrypicker’s Guides)
- Knowledge gaps: Critical information locked in employees’ heads (sound familiar, @yosclimber?)
- Process black holes: Departments working in silos (hello, unreachable shipping department!)
“Their show expert says yes to it, and when it goes in with a note as to what he said they don’t give it to me” – Swap “expert” for “engineering team” and you’ve got classic post-acquisition finger-pointing
4 Make-or-Break Checks for M&A Technical Due Diligence
1. Code Quality: The Devil’s in the Error Handling
Repeated attribution errors despite clear rules? That screams poor exception management. Here’s what I look for:
// Warning Sign - Silent Failures
function attributeVariety(coin) {
// Still referencing 1985 rules
const varieties = require('./old-guide.js');
return varieties.find(coin) || 'Standard'; // Oops, no error logging
}
// Healthy System - Defensive Coding
import {LatestGuide} from '@verified-rules';
import {auditTrail} from '@monitoring';
export default async function attributeVariety(coin) {
try {
const result = await LatestGuide.identify(coin);
auditTrail.log(coin.id, result); // Automatic paper trail
return result;
} catch (error) {
notifyExperts(coin); // Fail-safe protocol
return 'Needs Review';
}
}Deal killer: Systems that can’t self-correct when things go wrong
2. Scalability: What Breaks Under Pressure?
The grading company’s “fast submission” option that bypassed checks? I see tech equivalents daily:
- Throughput tripping over accuracy (that 9-day processing delay hid errors)
- Human bottlenecks (“Only Susan knows that system” = acquisition risk)
- Infrastructure crumbling under 2x normal load
Always ask: “Show me your performance metrics during last Black Friday-level traffic.”
3. Hidden Costs: When Quick Fixes Backfire
$200 FedEx labels to fix $20 errors? Classic symptom of patchwork systems. Watch for:
| Red Flag | Coin Example | Tech Parallel |
|---|---|---|
| Workarounds | Can’t retrieve shipped items | No rollbacks for bad deployments |
| Knowledge Silos | Printed guides vs digital | Tribal knowledge in Slack channels |
| Version Chaos | Conflicting FS numbers | APIs breaking integrations |
4. Culture: The Silent Deal Killer
Four service calls to fix one coin? That shows deeper issues:
- Teams passing the buck (“Not my department”)
- No automatic escalation paths
- Rewarding speed over accuracy
Pro tip: Ask engineers: “What happens when your monitoring system screams at 3 AM?” Their answer predicts integration headaches.
Your Action Plan for Better Tech Due Diligence
The 5-Point Inspection Checklist
Here’s the exact checklist I use when evaluating targets:
- Follow error paths – do they self-resolve or explode?
- Documentation audit – wikis or word-of-mouth?
- Hotfix deployment times – hours or weeks?
- Rollback capability testing
- API version consistency checks
Valuation Math: Quantifying Technical Debt
Found problems? Adjust offers using this reality check:
Real Value = Asking Price × (1 - [ (Untracked Errors × 0.15) + (Patchwork Fixes × 0.10) + (Knowledge Gaps × 0.20) ])
In our coin case, repeated resubmissions justified 12-18% price reduction. Tech debt deserves similar discounts.
Final Thought: Protect Your Investment
That misattributed coin wasn’t just a grading error – it was a warning. In M&A tech due diligence:
- Messy code = future integration nightmares
- Manual processes = hidden labor costs
- Siloed teams = cultural debt
Do the technical detective work upfront. Because discovering their systems can’t handle basic transactions post-close? That’s infinitely more costly than walking away from a bad deal.
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