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The Long Hold
The archive

Every letter

One real situation, one framework, and the moves you can make on Monday. Every Thursday since 2026.

2026

October 8, 2026

Adjusted EBITDA is a negotiating position, not a number

Somewhere underneath it is the figure that actually services the debt and funds the distributions. Here is how to find it.

The Buyer's View · 4 min
October 1, 2026

The First Hundred Days: a field guide to the handover nobody prepares you for

Five phases, one hundred days, and the questions that matter in each. The free guide for anyone taking a company on, or handing one over.

Key-Person Risk · 9 min
September 24, 2026

Leverage rarely kills a company on its own. Covenants and timing do.

How to read a credit agreement the way an operator has to, rather than the way a spreadsheet does.

The Buyer's View · 4 min
September 17, 2026

Year one runs on goodwill. Year two is when you find out what you bought.

The first year has momentum and the benefit of the doubt. Neither renews automatically.

Everything Runs Through You · 4 min
September 10, 2026

The company you inherit is a set of agreements nobody wrote down

The org chart tells you who's accountable. The decision map tells you what breaks when they leave.

Key-Person Risk · 5 min
September 3, 2026

The belief that built your company can quietly start running it

How to tell the difference between holding a conviction and being held by one.

Everything Runs Through You · 2 min
August 27, 2026

The primary job of a CEO is judgment, exercised repeatedly

Judgment requires space. Space requires doing less.

Everything Runs Through You · 2 min
August 22, 2026

There's a third option.

For founders compounding a business on their own terms. No raise, no exit.

Welcome · 2 min

One letter every Thursday. Free.

For founders building the quiet way: private, profitable, permanent. One real situation, one framework, and the moves you can make on Monday.

Free. One letter every Thursday. About ten minutes.