Balancing Simplicity and Complexity in Newsletter Success

Newsletters are not a new idea. Yet every few years the media business rediscovers them, anyway — either as a way to quickly launch a startup with bigger ambitions, or as a standalone business. Tim Huelskamp took the second route in 2017, when he co-founded 1440 — a newsletter that promises to quickly bring you the most important news of the day. Again — not a new idea. But Huelskamp seems to have figured out how to build something pretty big: He says 1440 has 4 million readers, and is turning a profit on something like $20 million in annual revenue. How’d he do it? What’s he going to do next? And how will he compete with AI companies that can do all of this faster, and cheaper? I’m glad you asked: I’ve got the same questions, so I asked him myself.

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