Technical & Strategic Diligence
Diligence from someone who also writes the cheque.
Product, architecture, AI, vendor, technical-debt, business-model, and execution-risk analysis for founders, boards, and investors. The same work I run on my own portfolio — applied to yours.
What it covers
Six surfaces, one assessment.
A diligence engagement is scoped to the decision in front of you. These are the surfaces I look at.
Product & architecture
What gets built, what it depends on, and what it costs to change.
AI & agent systems
Where models and agents do real work — and where they do not.
Technical debt
What is inherited, what is accruing, and what blocks the next stage.
Vendor & build-buy
Build, buy, or rent — and what each path locks in.
Business model
Revenue architecture, pricing logic, and unit economics.
Execution risk
Who owns the outcome, what cadence it runs on, and where it breaks.
Who commissions it
Three audiences, one standard.
The analysis is the same. The question it answers is different.
Investors
Pre-close diligence on product, technology, and AI claims — from someone who runs the same analysis on their own portfolio.
Boards
Independent assessment of technical risk, architecture decisions, and whether the team can execute the plan.
Founders
Pre-fundraise readiness: what an investor's diligence will find, fixed before it finds it.
Technical & Strategic Diligence