As a bit of a rebuttal to my recent post about publishing printed newsletters, Jeff Bezos had something of a similar situation after purchasing the Washington Post:
In addition to wanting the Post to operate within its means, Bezos applied elements of his well-tuned business philosophy to the paper. He preached the wholesale embrace of technology, rapid experimentation, and optimism about the opportunities of the internet instead of despair. “You’ve suffered all the pain of the internet but haven’t yet fully enjoyed its gifts,” Bezos told his new employees. “Distribution is free, and you have a massive audience.”
One slight difference is the Washington Post is the Washington Post and most newsletters for the people I’m talking about are a few hundred to a few thousand people in size on what are often incredibly niche topics.