“Based on Ben Settle’s tweets, which American president (NOT Donald Trump) does he sound like?”
So Stefania asked Grok.
To which, hallucinated quote about Halloween pulled from its own platform aside (guess I’ll have to give so-called AI another two years…), it answered with a surprisingly valuable email copywriting/marketing lesson.
(Grok’s wall-of-text answer edited for easier reading)
…Ben Settle is a direct-response copywriter and marketer known for his provocative, no-nonsense, and often polarizing email marketing advice.
His X posts tend to reflect this persona: blunt, opinionated, and unapologetic, with a mix of humor, self-promotion, and disdain for conventional thinking.
He often critiques modern culture, political correctness, and business norms, while emphasizing personal responsibility and contrarianism.
His style is informal yet commanding, and he’s not afraid to ruffle feathers to make a point.
Looking at American presidents (excluding Trump), one who stands out for a similar rhetorical flair is Andrew Jackson, the 7th president (1829–1837).
Jackson was a populist figure, known for his fiery, direct communication and disdain for elites.
He didn’t have social media, but his public speeches and writings—like his veto messages or his farewell address—were bold, confrontational, and aimed at connecting with the “common man” while attacking entrenched power structures (e.g., the Bank of the United States).
Jackson’s tone was often unpolished, aggressive, and polarizing, much like Settle’s tweets.
He positioned himself as an outsider, a trait Settle embraces by rejecting mainstream marketing dogma.
For example, Jackson’s 1832 Bank Veto Message called out “artificial distinctions” and “exclusive privileges” in a way that feels akin to Settle’s rants against “woke” culture or corporate fluff.
Both share a knack for plain-spoken, divisive rhetoric that rallies supporters and infuriates detractors. Jackson’s era lacked X’s brevity, but his style translates to short, punchy statements—like Settle’s tweet on March 25, 2025:
“Most people’s advice is just their insecurities wearing a cheap Halloween mask of wisdom.”
It’s folksy yet biting, a Jackson-esque vibe.
Other presidents, like Teddy Roosevelt, might come to mind for their boldness, but Roosevelt’s style was more polished and moralistic, less raw than Settle’s. Lincoln was too measured and philosophical, FDR too diplomatic in public. Nixon had paranoia but lacked the swagger. Settle’s unfiltered edge aligns most with Jackson’s frontier-spirit bravado.
So, based on [Ben Settle’s] tweets, he sounds most like Andrew Jackson.
I never wrote that Halloween line, just typical AI hallucinating.
Amusing how Grok can’t even accurately pull quotes from its own platform.
But as for the rest, l will take that as compliment.
Andrew Jackson has long been my #1 favorite President, for a whole host of reasons.
And there are many copywriting lessons embedded in this email, nestled between the lines for those with ears to taste and eyes to smell. The best lessons about nearly anything are very often taught that way.
Including stuff I write in the paid Email Players newsletter.
More about that here:
Ben Settle
