What have you learned in two years of newslettering? I love that Feed Me is proudly a business newsletter. Do you have a useful definition of “business”? What do you care about business in particular?
Running Feed Me has turned me into a writer, editor, salesperson, audience manager, product manager, designer, and marketer. And PR person. And founder. I wire the money, I answer the emails, I show up to the events. I like working for myself, but I get lonely. I don’t think newsrooms are supposed to be made up of one person.
The most fun stories I’ve worked on for magazines have been about specific ways people spend money (on members’ clubs, on whole milk, on squeeze bottles of olive oil) and what those say about culture at large. Feed Me is a newsletter about the spirit of enterprise — the personalities, motivations, and businesses that shape the world around us.
You and I do a lot of active listening to our readers. You do it in a more strategic way, to learn things and gather data; I do it in a more chaotic way. (I like hearing people’s funny stories and learning what they love!) What can I learn from you about having relationships with our readers and our subscribers that are cool for them? What are ways to bring more delight to readers that go beyond reading and sending? Harvesting reader questions for interviews is one thing you do, which is brilliant!
I wouldn’t give myself that much credit – I did my fair share of eavesdropping in the lobby at the Marlton (a poor man’s Casa Cipriani) yesterday.
Substack’s chat features need some work, but the comment section is gold. My comment section is paywalled. Everyone spending time there is paying to be there, which reduces the probability of trolls, but there are still creeps in there.
Earlier this year, I started a series called Guest Lecture. I wanted to capture the spirit of that (sometimes unhinged) guest lecturer who would come into your class on a Friday, drop more knowledge than you learned all year, maybe hit on a student, and then leave forever. It’s fun because readers — only the paid ones — get to ask questions to the subjects, like Andreessen Horowitz’s David Ulevitch or How Long Gone’s Chris Black.
You wrote something that was widely read about the recent age of writers, newsletters, sameyness, and monetization. I think it’s aging really well, and it ruffled feelings and thoughts alike when it came out. I’m quoting a bit extensively though people should read it in full: “Substack is making everyone into writers the same way Instagram made everyone into photographers … Creating content with the goal of making money off of it is different than creating content with the goal of getting likes, is different than creating content with the goal of being creative and connecting with other people.” (I should note you’re also very positive about Substack and its role in writing and writerhood.) Have things gone a different way since then? Or have they … calcified in this respect?
I published that essay while I was on a three-week vacation in Greece, and my vacation ended the day I hit “Send.” Substack users were really angry at me — they called me mean, they called me a gatekeeper; even Substack’s employees were talking about me.
But I did something right because it crushed. It is probably the most widespread non-politics story in Substack history. Many of my successful stories are kind of Rorschach tests — people see what they want.
To answer your question, I would publish the same thing today without a word changed, and it would still be true.
Also in that essay, you mention New York. “I remember in my job interview for New York Magazine in 2016, one of the men who interviewed me asked, ‘Do you think Kendall Jenner is really a model?’” Is there a way in which Kendall Jenner is not a model, in all the senses? And was that Carl Swanson?
It was not Carl!!!! Man, I miss that office.
Does the incoming Trump 2.0 era change your plans for work or life in some way?
I’m very curious about young people. A few weeks before the election, I started to make a podcast about American Gen-Z men. Partially because I was really irked by all the conversations about Girlhood at the end of 2023, partially because I kept reading about the spike in suicide and unemployment rates among Gen-Z men in America.
I stayed at the St. Regis in D.C. for a few nights the week before the election. The scene report turned into more of a horror story, so I tabled the newsletter. Maybe I’ll release it later this year. The iced vanilla latte I had at the White House was excellent.
