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October 14, 2025Why Technical Due Diligence Makes or Breaks Tech Acquisitions
Picture this: You’re about to acquire a promising tech company. The financials look solid, the team seems great – but what about the code? As someone who’s reviewed hundreds of tech acquisitions, I can tell you this: the state of a company’s codebase predicts its future better than any spreadsheet. Nearly 3 out of 4 tech acquisitions underperform, and more often than not, poor technical due diligence is to blame.
The $50M Mistake Hidden in Legacy Code
Early in my career, I watched a dream deal crumble over something most people would overlook. A hot startup with a $350M price tag? Their financials sparkled. But when we peeked under the hood, we found 14 different ways they handled dates across their system. That single discovery renegotiated the deal – and eventually killed it. It taught me that how a company organizes its code speaks volumes about how it runs its business.
What Really Matters in Tech Due Diligence
1. Code Quality Audit: Seeing Beyond the Surface
Forget basic code style checks. When I assess a company, I’m looking for three critical things:
- Does the architecture make sense? (Are components properly separated?)
- Do patterns stay consistent? (One auth system beats three half-baked ones)
- What’s the real cost of technical debt? (That quick fix from 2018 might cost millions to undo)
// A real example from last month’s audit:
app/
├── v1/ (Original API)
├── v2/ (Newer version)
└── v3/ (Abandoned experiment still in production!)
2. Scalability: Can It Actually Handle Growth?
Too many startups build for today, not tomorrow. Last year, we tested a “cloud-native” platform that crumbled at just 50 users. Our tests revealed:
- Database connections leaking like a sieve
- Server sizes set in stone (in 2023!)
- Critical services that couldn’t scale automatically
The result? A 30% price cut to cover $2M in needed upgrades.
3. The Hidden Risks in Open Source
Dependencies can be landmines. We automatically scan for:
- Problematic licenses (AGPL in proprietary code? Run.)
- Abandoned projects (No updates in 2+ years?)
- Hidden vulnerabilities (Remember Log4j?)
One client nearly bought a company where over half their Docker images had critical security holes. Deal delayed.
4. Knowledge: Who Really Keeps the Lights On?
The most overlooked risk? What walks out the door when key people leave. We measure:
- Are runbooks complete or wishful thinking?
- How long does it take new engineers to fix issues?
- Are important decisions documented or just in Slack history?
One buyer dodged disaster when we found 40% of critical knowledge lived in two engineers’ heads.
The SCALE Framework: A Practical Approach
After evaluating over 100 companies, here’s what we actually check:
- Stack Analysis: What’s core vs. experimental?
- CI/CD Health: How often do deployments fail?
- Architecture: Do service boundaries make sense?
- Licenses: Any legal timebombs?
- Extensibility: Can we actually build on this?
Deal-Breakers We Watch For
These always trigger tough conversations:
- Microservices that depend on each other in circles
- Passwords committed to Git (Yes, it still happens)
- Critical code with no tests
- Enough logging systems to confuse an army
Real Deal: How Due Diligence Saved $120M
When a Fortune 500 wanted to buy a DevOps startup, we found:
- Surprise Oracle database dependencies
- Engineers sharing root AWS accounts (yikes)
- License violations in their core product
We structured the deal so 20% ($24M!) depended on:
- Fixing the database mess
- Implementing proper access controls
- Cleaning up the licensing issues
The Bottom Line: Good Code Means Good Business
Technical due diligence isn’t about nitpicking – it’s about understanding real value. Companies with clean code, solid architecture, and good practices consistently outperform others post-acquisition. In fact, our data shows well-prepared tech companies deliver returns 3x faster than messy ones.
Remember:
- Automated tools help, but human expertise catches what they miss
- Documentation quality predicts integration headaches
- Price the deal based on real tech debt, not hopes and dreams
- Use what you learn to plan post-merger integration
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