# Chenmark Weekly Thoughts

Weekly essays from a holding company's founders.

A weekly essay series running since September 2014 from the Portland, Maine holdco's founders: short, candid pieces on buying and operating small businesses, written a year before they bought their first company and continuously through building a multi-company group.

- Category: Newsletters
- Pricing model: Free
- Where it fits: Learn & Choose Your Path, Operate & Grow the Business
- Website: https://chenmark.com/weekly-thoughts/

## At a Glance

Subscribe and read backward: the archive is the closest thing to a longitudinal diary of the small-business holding path.

## What It Costs

Free; subscribe on the site, full archive open.

## Best For

A weekly dose of what the holdco path actually feels like, from people a decade in, without a course or community attached

## Pros and Cons

- Pro: A decade-plus archive that documents the journey in real time rather than in retrospect
- Pro: Candid about the gap between holdco spreadsheet math and the daily reality of small operations
- Pro: Zero monetization pressure on the reader: no product, no cohort, no gate
- Con: Essays, not instruction; you will not find a how-to sequence here
- Con: Seasonal-business (their portfolio) specifics color some operational takes
- Con: Publishing cadence and depth vary week to week, as a real operator's writing does

## What Searchers Say

A quiet staple of SMB reading lists; the archive's Required Reading and small-business-resources pages are themselves cited as curation. Referenced regularly when the holdco conversation turns from theory to practice.

## Sources

- https://chenmark.com/weekly-thoughts/
- https://chenmark.com/weekly-thoughts/thoughts-on-weekly-thoughts/

Also on this site: https://searchspheresource.com/resources/category/newsletter.md
Source: https://searchspheresource.com/resources/chenmark-weekly-thoughts
Last checked: 2026-07-12

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