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The Ben Thompson + Bill Simmons Baby

The Story

A pivotal moment in the origin of Not Boring came when Packy McCormick signed up for David Perell’s Write of Passage course. The key concept he learned was nailing the “monopoly of you”: bringing together a few things that make you unique and writing at the center of those things (Source 1).

Packy wanted to write about business strategy. The problem was Ben Thompson’s Stratechery was already one of the best newsletters on the internet. But Packy saw an opening: write about tech and business strategy in a fun, less serious way. He drew inspiration from being a fan of Bill Simmons, who mixed sports journalism with pop culture references in a novel way (Source 1).

“If Ben Thompson and Bill Simmons had a baby, it would look like Not Boring” (Source 1).

One close friend described Packy’s particular quality as “voice-market fit”: he launched during the pandemic into difficult times with infectious optimism, “the likes of which many of us left behind in the 2010s.” The type of optimism that would tell you that the pandemic might have been “the greatest catalyst for progress and creativity in human history” (Source 2).

None of this was manufactured. As Packy said: “It’s really hard to do this every single week if you’re not being yourself” (Source 1). He noted that it would be exhausting to fake it because he’s always online, writing, tweeting, and talking to founders. The optimism and enthusiasm are who he is.

Lesson for Creators

Finding your positioning doesn’t mean inventing a persona. It means identifying the intersection of what already makes you different. Packy didn’t try to beat Ben Thompson at his own game. He didn’t try to become Bill Simmons. He found the overlap between his genuine interests (business strategy), his personality (optimism, humor, pop culture), and an underserved need (making tech strategy fun to read). “Voice-market fit” is just as important as product-market fit.

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