My take, after spending years in the prep-school-to-Ivy pipeline: it's not a lack of education, it's a signaling mechanic.

For most of us, grammar is a proxy for competence. We proofread because a mistake could cost us a grade, client, or a job. But the ultra-rich are basically operating post-economically. They aren’t trying to advance; they started rich and they’ll end rich, so they have absolutely no one to impress (and certainly not you).

When you grow up in an environment where friction is historically outsourced—where papers are bought, tutors do the heavy lifting, or SATs are taken by proxies—you never really get held to the same operational standards. You just learn to slop it across the finish line because the consequences for failure are zero.

So who are they trying to impress with their grammar? Nobody. It actually becomes a display of asymmetric leverage. Taking the time to craft a perfect, well-punctuated email screams, "I spent my valuable time optimizing this for you." A typo-ridden, lowercase, one-sentence reply sends the exact opposite message. It establishes a power dynamic where their two seconds of raw attention is the most valuable commodity in the exchange. Following spelling conventions is just middle-class anxiety; sloppiness is the flex. All conventions are for the plebs anyway.

Plus, low-fidelity communication gives them incredible optionality. A garbled, ambiguous text provides perpetual wiggle room. They weren't late or wrong, it was just a typo. It allows them to remain completely non-committal—just another way to maintain high status while shedding any actual accountability.