3 Technical Due Diligence Red Flags Hidden in Your Target’s Codebase (Wisconsin Quarter Case Study)

When Technical Debt Turns Toxic for Business Deals

When tech companies evaluate acquisitions, few things kill deals faster than discovering hidden technical landmines. Let me show you how problematic code patterns – much like those mysterious Wisconsin quarters with extra leaves – can reveal serious risks during M&A due diligence. Through this unusual numismatic case study, you’ll learn to spot warning signs that could make or break your next acquisition.

Coin Mysteries Meet Code Mysteries

Remember those puzzling Wisconsin quarters with unexplained extra leaves? Collectors spent years debating whether these were accidental errors or deliberate modifications. Tech acquirers face similar detective work when they encounter:

• Strange code that nobody can explain
• Features that break under pressure
• Security holes that shouldn’t exist

The Die-Struck Truth

Coin experts settled the quarter debate through physical analysis:

“The sunken deformation under the low leaf shows the mark was made after hubbing”

We apply this same “when and how” logic to suspicious code:

1. Was it part of the original design?
2. Did someone patch it later?

3 Codebase Red Flags That Should Alarm Buyers

1. The Ghosts of Developers Past

Just like the 18-year quarter mystery, we often find code comments that tell troubling stories:

// TEMPORARY FIX - remove before launch
adminOverrideSecurity(USER_PERMISSIONS);

Dated 2012. Still running in production today. Yikes!

2. Following the Digital Paper Trail

Numismatists used microscopes to compare coin details. Our tech audit toolkit includes:

• Commit history timelines
• Code change frequency maps
• Architecture consistency checks

Reality Check: Can Their Systems Actually Scale?

When Estimates Meet Reality

Coin collectors noticed something familiar:

“Mint production estimates rarely match actual counts”

Sound familiar? Many startups overpromise on:

The Million-Dollar Question: Accident or Cover-Up?

Could This Be Intentional?

One collector’s experiment proved revealing:

“Nobody could’ve added those leaves to hardened dies”

Our approach mirrors this forensic thinking when we find:

1. Security gaps that require insider access
2. Code changes made off-hours

Compliance Time Bombs

In our tech investigations, we always check for:

• Unauthorized database access
• Shadow IT systems
• Overprivileged user accounts

Your Technical Due Diligence Checklist

4 Non-Negotiable Audit Steps

Borrowed from numismatic investigation methods:

1. Tool Tracking: Document every deployment tool and script
2. Timeline Mapping: Line up code commits with project reports
3. Access Forensics: Find all admin-level entry points
4. Pattern Spotting: Group similar undocumented features

The Real Value in Unexplained Anomalies

The Wisconsin quarter mystery teaches us that oddities demand three questions: How did this happen? Why wasn’t it fixed? What’s the real impact? For tech acquirers, thorough due diligence means:

• Treating code like archaeological evidence
• Tracking who could access critical systems
• Pressure-testing scalability claims

In both coin collecting and tech acquisitions, the biggest risks – and opportunities – often lurk in the hidden flaws you can’t afford to miss.

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