>one day they started getting hounded by Let's Encrypt multiple times

>trying to get a small company to shell out $50k as a "donation".

>Even more so if, like Let's Encrypt, you are turning up on the doorstep asking for $50k a pop.

Does your friend have anything to corroborate this claim? Perhaps the email with identifying details censored?

I have a received an occasional email mentioning donations. They are extremely infrequent and never ask me for a specific amount. I would be incredibly surprised to see evidence of "hounding" and requests for $50,000.