Email-Newsletter Start-ups and The Future of Media


    “The internet broke a lot of things that were working,” Best says in a phone call. “Craigslist broke Classifieds, which killed newspapers. Facebook and Google have taken over internet advertising. There’s a descent into madness a little bit, where the incentive structure of ad-supported social media creates a lot of bad outcomes. It’s broken on a personal level, for consumers of media.”

    With newsletters, he argues, writers are directly supported by the people who want to read them.“You’re not giving someone your cultural output for free.”

    “Direct subscriptions are a better business model for culture,” according to the Substack about page. Best says more than 50,000 people are paying to read at least one newsletter on Substack, and about 20 percent of publishers charge something for what they write (the platform’s minimum is $5 a month). Once a publisher has built up a following, he says, and flips the switch from free to paid, there’s a roughly 10 percent conversion rate.

    All of that is great, and it’s nice to feel that we are moving away from a mode of thinking in which people who put out creative work on the internet should mostly do so without getting paid. It’s also, not really, the whole story. Arguably, it’s another example of money and prestige coming for an internet-age creative format that was better when it was a hush-hush community activity—non-remunerative, anti-discovery algorithm, full of in-speak, artistically strange (see: podcasts, blogs, fanfiction, memes). And ambivalent, like women online have to be.

    On Substack’s website, a history of the email newsletter runs through the stories of seven men—including the famous conservative political columnist Andrew Sullivan, the business analyst Ben Thompson, the gaming critic Jim Sterling, and the podcast industry commentator Nick Quah—as well as one woman, Jessica Lessin, who founded the subscription-based tech publication The Information in 2013.

    It’s fairly similar, actually, to a recent New York Times trend piece by tech reporter Mike Isaac (“The New Social Network That Isn’t New At All”), which features quotes from several men whose newsletters Isaac subscribes to, all of which involve a subscriber fee. (Isaac, for his part, has a free newsletter on Substack called “brain dump,” which is a weekly collection of what he calls “garbage” that falls out of his head.)

    On Twitter, readers were quick to point out how strange it was not to interview a single woman for a story about newsletters, a form that was championed and, arguably, perfected by women years ago. Isaac apologized quickly for the mistake, but it’s easy to see why he made it.

    “[Newsletters have] been a thing,” Ann Friedman, who has written a weekly newsletter since 2013, has 40,000 subscribers, and is widely recognized as one of the leaders of the first newsletter boom, which happened mostly among women and on TinyLetter, which had no monetization mechanism. “The reason you have a tech reporter at The New York Times saying it’s a thing now is because people with money, most of them male, are newly interested in the medium writ large. Men with money are betting on people wanting to continue to consume this medium.”





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