Diligence for lower middle market transactions

Buyers and sellers ask the same questions from opposite sides of the table. The evidence is identical. Only the interpretation inverts.

Most of what determines whether a transaction succeeds is knowable before it closes. Very little of it appears in the financial statements.

A buyer needs to know whether the earnings survive the debt. An owner needs to know what a buyer will find, while there is still time to change it. These are the same investigation conducted in opposite directions, and both are chronically underserved below the threshold where private equity brings its own diligence teams.

Two directions

Buying. Assessment of a target under LOI or in screening — revenue defensibility, verification of the capabilities being represented, transfer and continuity risk, and what the first twelve months actually cost. Scoped to complete inside an exclusivity period.

Selling. Assessment of a business three to ten years from exit — what a buyer will find, what it will cost in price or in terms, and which of it can be fixed while there is time. Findings are a discount list when a buyer produces them and a work plan when you produce them first.

Method

Four independent sources: documents, structured interviews, direct observation of the systems in use, and external measurement that requires no cooperation from anyone.

Collected separately, they rarely agree in full. The disagreements are where the findings are — a capability confirmed in conversation but absent from the contracts and invisible from outside is not a missing feature. It is a revenue projection resting on something that does not exist.

The method is published in full. Diligence that cannot explain itself is not diligence.

Scope

Engagements run from a two-day external read requiring no seller cooperation, to a full assessment scoped against an exclusivity window. Businesses between roughly $500,000 and $10 million in enterprise value, concentrated in service, trades, and field operations.

This is not a financial quality of earnings review. Earnings verification, add-back substantiation, and working capital analysis are performed by a CPA, and where that work is needed and not underway, an introduction is available.

Who

John Wallace. Twenty years in enterprise infrastructure and engineering leadership, including a cloud engineering organization of twenty-four at a national healthcare payer, and senior technology leadership in mortgage and financial services. Currently a fractional CIO to companies in regulated industries.

I am also an active buyer, running my own search for a lower middle market service business. These instruments exist because I built them for my own diligence first.