Take the writer Helena Fitzgerald’s newsletter “Griefbacon” (formerly on TinyLetter, now on Substack). This June, she wrote an installment about a concert I’d also been at, for a popular indie dad-rock band that she loves, and that I love, too. She mocked them a little, saying things like, “Their whole onstage persona is that of a man eternally one drink away from starting every sentence with my wife.” And that the lead singer seems “caught up in his sexuality like a sea lion tangled in a microphone cord.”

This is not an essay you can imagine being received the same way on a mainstream music blog, especially one read by men who worship indie rockers, or people who don’t already know Fitzgerald’s style. And as she goes on, she pulls out the personal part, which is that these weird and funny bits of psychoanalysis of strange older men is part of her own sexual history with “dads” and people who radiate, as she calls it, “big divorce energy.”

She’s kidding, but it’s serious; the arguments are playful, and then they’re meticulous; it’s a several-thousand-word piece of cultural criticism, but it’s also just an email. The ambivalence of the format is what makes it special, and the privacy is what makes that possible.

“It’s actually documented and verified if you go back to the earliest things being written about TinyLetter, [that] it was mostly women writing them or creating them,” Shane said. “But I think it’s just convenient to ignore it and act like this is something that a few enterprising men and Silicon Valley guys realized, cut out this period where women were popularizing it and using it in very particular ways, and be like, Oh yeah, look at this thing we found.”

But intimacy and weirdness and specificity don’t tend to be compatible with making money, at least not at Silicon Valley scale. Double Bounce, the weird internet-inspired TinyLetter spin-off developed by my friend Claire’s brother, allowed writers to charge subscription fees but kept the same underground feel. There was no discovery section; you could only subscribe to new newsletters if someone sent you the URL directly. (“You get people who come in and have 12 people sign up and the 12 people never unsubscribe and they read every single thing … We all don’t need to be internet megastars, in fact I think we’d all be better if we weren’t all trying to be internet megastars,” Alex Carusillo said shortly after he launched the site.) Writers could also charge whatever fees they wanted, and most chose fairly low ones.

The platform was out of business within a year, and Substack, started by acquaintances of Alex Carusillo, arrived shortly after.

The BuzzFeed News journalist Anne Helen Petersen writes another of the more popular newsletters on Substack, and calls herself an early convert. “TinyLetter is a piece of shit and you can quote me on that. [Mailchimp has] consciously decided they’re going to let it die on the vine,” she speculates. (Contacted for this story, a Mailchimp spokesperson said, “There are no immediate plans to sunset TinyLetter, but Mailchimp plans to integrate it into the main Mailchimp platform in the future.”)