Technical Due Diligence

Architecture and code. Is the system built to survive the growth in the plan? Where is the technical debt, is it deliberate, and what does servicing it cost per year?

Team and key-person risk. Who actually holds the knowledge? What happens if the two people who understand the billing system leave three months after completion? This is consistently the finding that most changes a deal, and consistently the one least well covered.

Delivery. Can they ship? Track record against plan, release cadence, and how they behave when something breaks at two in the morning.

Security, compliance, and licensing. The obligations that arrive with the asset, including the open-source terms nobody has read since 2019.

Cost. What the platform actually costs to run, and how that scales with the revenue in the model — the two often disagree.

Before an investment or acquisition, obviously. But also in situations that are not transactions at all: a board that wants an independent read before committing to a rewrite, or a management team inheriting a platform they did not build and need to understand before they are held responsible for it.

Vendor assessment is a related case. If you are about to make a long-term bet on a supplier's platform, the same questions apply, and the answers are harder to get once the contract is signed.

Two to four weeks, structured, with no surprises at the end. Documentation and codebase review, interviews with the engineering team and with the people who depend on them, and a look at the operational reality — incidents, monitoring, what the on-call rota looks like at three in the morning.

Interviews matter more than the code. Code tells you what was built; people tell you why, what they would do differently, and what they are worried about. A defensive engineering team is itself a finding.

I report findings graded by materiality, separating what would stop a deal from what is simply a cost of ownership, with an estimate attached. Where I am uncertain I say so and explain what would resolve it, rather than hedging everything into uselessness.

A written report your investment committee can read, with an executive summary that states a view rather than surveying options. Findings graded by materiality with cost estimates. A view on key-person risk and what retention would need to look like. And a debrief conversation, which is usually where the most useful part happens.