I should buy a newsletter

alex

May 21, 2024 — 1 min read

Recently, two internet friends from the same group chat bought newsletters at ~basically the same time. (Prequel, about kids + entrepreneurship; and Newsletter Business, whose purpose is in the name. Go subscribe if you vibe with those topics!) When I found out, I responded:

It started as a joke, but now... 🤔 I'm thinkin' buying a cash-positive newsletter or media business could be a pretty decent way to learn about a new industry:

Relatively low startup costs + high reversibility. Media assets tend to be easy to transact.
Buying the asset provides skin in the game. Running an industry newsletter requires higher engagement than just reading one. More hands-on learning.
Cashflow is a good signal for the usefulness of the newsletter's information, at least in a business context.
Best case, it serves as a beachhead for other businesses and products. Worst case, it's a neat investment.

The popular case study these days is FreightWaves + Craig Fuller. Clearly it's worked out for him, cause he is now buying an aviation magazine. Seems like a pretty good playbook? Or maybe I'm just getting too caught up in the latest SMB/HoldCo twitter memes.

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