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The Long Hold

Private.Profitable.Permanent.

A letter for founders who raise once (or never), build companies that pay for themselves, and plan to keep what they built. Every Thursday.

Free. One letter every Thursday. About ten minutes.

Start here →

One real situation, taken apart.
One framework you can reuse.
The moves you can make on Monday.
The four pillars

Every month, four letters

One from each pillar. Together they cover how the company is funded, how it pays, how it lasts, and how it is run.

Private

Fund and own your company on your terms. Raise once, or never.

Profitable

Make the business pay, and keep paying.

Permanent

Make it last: moats, people, succession — and what makes stepping away from a business succeed or fail.

The Quiet Way

Use AI to do more with what you already own.

Playbooks

The frameworks, ready to use

All playbooks →
Permanent

The Three Questions

Thirty minutes with every person, asking the same three questions, to surface what's load-bearing.

From the letter: The First Hundred Days →
How to run it
  1. What should I be careful not to change?
  2. What is broken that everyone already knows about?
  3. If you had my job, what would you do first?
Private

The Covenant Check

The buyer's view

Find the date your debt is really tested, and how much room you have on it.

From the letter: Leverage rarely kills a company on its own. Covenants and timing do. →
Profitable

Owner Earnings, Bottom Up

The buyer's view

Build the cash figure that actually services debt and funds distributions, instead of arguing about adjusted EBITDA.

From the letter: Adjusted EBITDA is a negotiating position, not a number →

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.