Technical Debt & ArchitectureAugust 31, 20263 min read
The 5 Architecture Red Flags That Kill a Deal in Diligence
Architecture rarely kills a deal on elegance. It kills it on five specific patterns that a buyer can price within days.
Read analysisInsights
Analysis from inside live diligence engagements.
Short, specific notes on what actually moves price in software transactions, written by the practitioners doing the work.
Process & Organizational ReadinessAugust 24, 20263 min read
10 Things to Fix 6 Months Before You List Your Company
A six-month runway is enough to change how a buyer prices your engineering organization. Here is where that time is best spent.
Read analysisSecurity & IP PostureAugust 17, 20263 min read
What a Buyer's Security Review Actually Looks For
Security diligence is less about your control framework and more about whether your practices match what you claim in the data room.
Read analysisDeal Mechanics & Buyer EducationAugust 10, 20263 min read
What Happens in a 10-Day Technical Due Diligence Sprint
A day-by-day view of how a compressed technical diligence engagement is actually run, and what each phase is designed to produce.
Read analysisExit Readiness & ValuationAugust 3, 20263 min read
How Technical Debt Discounts Your Multiple
Technical debt does not reduce revenue. It reduces the confidence a buyer has in the revenue continuing at the same cost.
Read analysisTechnical Debt & ArchitectureJuly 27, 20263 min read
Monolith vs. Microservices: What Buyers Actually Care About
The architectural style is close to irrelevant in diligence. What matters is whether the boundaries match how the team works.
Read analysisProcess & Organizational ReadinessJuly 20, 20263 min read
The Metrics an Acquirer Will Ask For (That You Probably Don't Track)
Engineering metrics that never mattered to running the business become evidence the moment a buyer starts modelling risk.
Read analysisSecurity & IP PostureJuly 13, 20263 min read
Open Source License Landmines That Surface in Diligence
License exposure is the fastest finding to surface and among the slowest to remediate. Triage order decides whether it becomes a deal issue.
Read analysisDeal Mechanics & Buyer EducationJuly 6, 20263 min read
A Search Fund Buyer's Guide to Technical Risk
Searchers acquire businesses they will personally operate. That changes which technical risks matter and which are noise.
Read analysisExit Readiness & ValuationJune 29, 20263 min read
The Exit Readiness Audit: A Founder's Pre-Sale Checklist
A structured self-assessment covering the technical evidence a buyer will request, and what a credible answer looks like for each item.
Read analysisCase Studies & War StoriesJune 22, 20263 min read
The Deal That Almost Died Over a Single Database Migration
An incomplete migration left two sources of truth in production. The finding was small, the implication was not.
Read analysisTechnical Debt & ArchitectureJune 15, 20263 min read
How to Read a Codebase Like an Acquirer Does
Acquirers do not read code for quality. They read it for concentration, coupling, and the cost of the next change.
Read analysisProcess & Organizational ReadinessJune 8, 20263 min read
Founder-Dependency: The #1 Reason Deals Get Repriced
When the founder is still the architecture, the buyer is not acquiring a system. They are acquiring an employment risk.
Read analysisSecurity & IP PostureJune 1, 20263 min read
Who Actually Owns Your Code? IP Assignment Gaps to Fix Now
IP assignment gaps are quiet until a buyer's counsel finds them, at which point they become a condition of closing.
Read analysisDeal Mechanics & Buyer EducationMay 25, 20263 min read
Technical DD vs. Financial DD: Why You Need Both
Financial diligence tells you what the business earned. Technical diligence tells you what it will cost to keep earning it.
Read analysisTechnical Debt & ArchitectureMay 18, 20263 min read
The Hidden Cost of "Works Fine" Legacy Systems
A stable legacy system is an asset right up until the moment somebody needs to change it. Buyers price the change, not the stability.
Read analysisProcess & Organizational ReadinessMay 11, 20263 min read
What Happens When Your Best Engineer Is a Flight Risk During Diligence
Diligence is when key-person risk becomes visible to everyone at once, including the key person.
Read analysisDeal Mechanics & Buyer EducationMay 4, 20263 min read
How Technical Findings Actually Move Purchase Price
Findings do not move price directly. They move the buyer's model, and the model moves the price.
Read analysisExit Readiness & ValuationApril 27, 20263 min read
Should You Fix It or Disclose It? A Framework for Pre-Sale Tech Issues
Not every known issue should be fixed before a sale. Some should be scoped, priced, and disclosed deliberately.
Read analysisTechnical Debt & ArchitectureApril 20, 20263 min read
Why Buyers Discount Companies Running on Old Language Versions
An unsupported runtime is not a style objection. It is a hiring constraint, a security exposure, and a scheduled cost.
Read analysisProcess & Organizational ReadinessApril 13, 20263 min read
Documentation Debt: The Silent Deal Killer
Missing documentation is rarely the finding itself. It is the reason every other finding takes three times as long to resolve.
Read analysisSecurity & IP PostureApril 6, 20263 min read
SOC 2 Isn't Enough: What Technical Buyers Check Beyond Compliance
A clean report proves a control framework existed during an observation window. Buyers test whether the practice held afterwards.
Read analysisDeal Mechanics & Buyer EducationMarch 30, 20263 min read
The Diligence Timeline: A Week-by-Week Breakdown
Where technical diligence sits inside the wider transaction schedule, and which decisions depend on it.
Read analysisExit Readiness & ValuationMarch 23, 20263 min read
What a Clean Codebase Is Actually Worth at Exit
Clean code does not add a premium by itself. It removes the deductions and shortens the process, which is where the value shows up.
Read analysisTechnical Debt & ArchitectureMarch 16, 20263 min read
Cloud Cost Sprawl: A Diligence Red Flag Disguised as Growth
Infrastructure spend that grows in line with revenue tells a buyer the unit economics do not improve with scale.
Read analysisProcess & Organizational ReadinessMarch 9, 20263 min read
Why "It's All in My Head" Is a Valuation Problem
Institutional knowledge that lives in one person is an asset that does not transfer with the share certificate.
Read analysisSecurity & IP PostureMarch 2, 20263 min read
The Contractor Problem: IP Risk From Non-Employee Developers
Contractors accelerate delivery and complicate ownership. The complication surfaces years later, in a data room.
Read analysisDeal Mechanics & Buyer EducationFebruary 23, 20263 min read
Red, Yellow, Green: How We Score Technical Risk
A scoring model is only useful if two different reviewers reach the same conclusion from the same evidence.
Read analysisExit Readiness & ValuationFebruary 16, 20263 min read
Timing Your Sale Around Your Tech Stack's Maturity Curve
There is a window between a platform being proven and a platform being dated. Selling inside it is worth real money.
Read analysisCase Studies & War StoriesFebruary 9, 20263 min read
What We Found in 10 Days That Changed the Purchase Price by 15%
Three findings, none individually fatal, that together rewrote the buyer's first-year investment plan.
Read analysisTechnical Debt & ArchitectureFebruary 2, 20263 min read
Single Points of Failure: How Buyers Find Them in 48 Hours
Concentration risk is easy to detect and hard to hide. Two days of the right questions is usually enough.
Read analysisProcess & Organizational ReadinessJanuary 26, 20263 min read
Building an Engineering Org That Survives a Change of Ownership
The structures that make an engineering team resilient are the same ones that make it attractive to an acquirer.
Read analysisSecurity & IP PostureJanuary 19, 20263 min read
Data Privacy Skeletons That Surface in Technical Diligence
Privacy findings rarely come from the policy. They come from the copies of production data nobody remembered making.
Read analysisDeal Mechanics & Buyer EducationJanuary 12, 20263 min read
What Brokers Should Know Before Bringing in a Tech DD Firm
The point of technical diligence in a brokered process is to remove surprises, not to introduce them late.
Read analysisExit Readiness & ValuationJanuary 5, 20263 min read
The ROI of a Pre-Sale Technical Cleanup Sprint
A focused six-week cleanup, chosen correctly, routinely returns more than it costs. Chosen badly, it returns nothing.
Read analysisTechnical Debt & ArchitectureDecember 29, 20253 min read
What "Scalable" Actually Means to a Technical Due Diligence Team
Scalability in diligence is a cost question with a specific denominator, not an engineering adjective.
Read analysisProcess & Organizational ReadinessDecember 22, 20253 min read
The Bus Factor: How Many People Can Your Company Lose and Survive?
A single number, honestly calculated, that tells a buyer more about operational risk than most of the data room.
Read analysisSecurity & IP PostureDecember 15, 20253 min read
How a Single Unpatched CVE Can Delay a Closing
One critical vulnerability in a customer-facing path can pull a closing timetable apart, regardless of exploitability.
Read analysisDeal Mechanics & Buyer EducationDecember 8, 20253 min read
Reps and Warranties: Where Technical Risk Hides in the Purchase Agreement
Technical findings do not stay in the report. They are translated into representations the seller stands behind personally.
Read analysisExit Readiness & ValuationDecember 1, 20253 min read
How Recurring Revenue Quality Ties Back to Technical Architecture
Revenue durability and architectural choices are more closely connected than either the financial or the technical workstream usually admits.
Read analysisTechnical Debt & ArchitectureNovember 24, 20253 min read
The Database Decisions That Come Back to Haunt an Exit
Data model choices made in the first year are the hardest thing to change in the tenth, and buyers know it.
Read analysisProcess & Organizational ReadinessNovember 17, 20253 min read
Runbooks, Onboarding Docs, and Other Diligence Table Stakes
A short list of artefacts that every buyer requests and most sellers assemble in a panic during week one.
Read analysisSecurity & IP PostureNovember 10, 20253 min read
Access Control Chaos: What Buyers Find in Your Admin Panels
Internal tools are built for trusted colleagues and rarely revisited. Diligence looks at them anyway.
Read analysisDeal Mechanics & Buyer EducationNovember 3, 20253 min read
Post-Close Technical Integration: What to Plan Before You Sign
Integration cost is real, predictable, and almost always absent from the model until the week after closing.
Read analysisExit Readiness & ValuationOctober 27, 20253 min read
Preparing for Diligence While Still Running the Business
The preparation that damages a company is the preparation that stops it growing. Sequencing prevents that.
Read analysisTechnical Debt & ArchitectureOctober 20, 20253 min read
Vendor Lock-In: Quantifying the Risk Before a Buyer Does
Every dependency is lock-in of some degree. The question a buyer asks is what it would cost and how long it would take to leave.
Read analysisProcess & Organizational ReadinessOctober 13, 20253 min read
How to Prep Your Engineering Team for a Diligence Interview
Diligence interviews are not exams. They are consistency checks, and over-coaching is the fastest way to fail one.
Read analysisDeal Mechanics & Buyer EducationOctober 6, 20253 min read
Escrow and Indemnification: How Technical Findings Change Deal Terms
Findings that do not move the headline price often move the structure instead, and structure is where sellers lose money quietly.
Read analysisCase Studies & War StoriesSeptember 29, 20253 min read
The Micro-Cap Acquisition Where Undocumented Code Was the Whole Risk
A small, profitable, boring business where the only material finding was that nobody could explain how it worked.
Read analysisCase Studies & War StoriesSeptember 22, 20253 min read
Anatomy of a Clean Diligence: What Good Actually Looks Like
Clean diligence is not the absence of findings. It is a seller who already knew every finding and could price each one.
Read analysisExit Readiness & ValuationSeptember 15, 20253 min read
Why Buyers Chip Price in Week Three
Most valuation erosion in software deals does not start with the numbers. It starts with an unanswered technical question that hardens into a discount.
Read analysisSecurity & IP PostureSeptember 8, 20253 min read
Scoping Open-Source License Risk Inside a Ten-Day Window
License exposure is the fastest finding to surface and the slowest to remediate. Here is how we triage it under deal pressure.
Read analysisProcess & Organizational ReadinessSeptember 1, 20253 min read
Key-Person Dependency Is a Valuation Input, Not a Culture Note
When one engineer is the only path to production, the buyer is not acquiring a system. They are acquiring an employment risk.
Read analysis