In service of writers

Every few months, I get to spend some time in New York, and I use it to meet with as many writers as I can. I cajole them over beers to start a substack. I ask them over lunch how I can make their lives better. Sometimes, I just want to hang out with them because I like their work. 

I’ve just finished one such 27-hour visit, and as ever it was a fever of meetings, meals, and booze. I’ve come away energized, as I always do, but this time it felt a little heavier than usual. I’m not exactly sure why. Perhaps it’s my stage of life, or that there are some things going on at work that have been weighing on me, or maybe it was the contents of the conversations. But I find this work so meaningful. Professionally, at least, there is nothing more important to me than to feel I am helping writers. 

In Bryant Park, a writer who has been on Substack since the earliest days confessed that he is struggling. He has a day job that is bringing stresses, a young child with a challenging health situation, and some problems with his substack that he just hasn’t been able to solve. He was at his wit’s end. He might shut his publication down. Could we help? Is there anything we can do to make his life simpler, to help him breathe again? We went for a walk. He clasped both hands on my shoulders and looked me in the eye. “I’m sorry man, I keep bringing you all my problems.” I took him to the office and introduced him to a team member who recently joined to help writers navigate tricky tech issues.  

At dinner in Soho, seated with a colleague and four writers around a round table in a noisy Italian restaurant, a writer unloaded a litany of complaints stemming from her recent frustrations with Substack. We didn’t respond well enough after a big problem that was partially our fault. We had given other writers a lot of support but not her. We were messing things up by prioritizing followers over subscribers. There are competitors now that are almost as good as Substack and don’t charge 10% of subscription revenue, she said. They’re getting more and more tempting. She expected more from us. I tried to hold my agitation in. For years, I have seen the positive impact Substack has had on this writer’s life, and we have always tried to give her first-class treatment. I’m not sure my attempts at suppression succeeded. I told her that if she’s unhappy with Substack, she can move to a different platform. We designed Substack so that you own and control your mailing list, content, and even payments relationships—and you can leave and take them with you at any time. We have set everything up so that we can win only if writers win. We didn’t start the company in 2017 because we were greedy capitalists. Writers weren’t exactly the most lucrative customer base at that time. We did it because we wanted to help writers and give them more power. Things don’t always go well. We’re a startup trying to bring a new system into the world at the same time as trying to make a good company at the same time as trying to balance the interests of thousands of publishers who have different needs and opinions and joys and criticisms. If she feels that we have let her down, then we have. We will try to make it right. At the end of the night, we hugged and she said: “Sorry for roasting you in front of everyone.”

Over matcha and coffee at 8.30am at an Irving Farm in NoMad, a writer who has built huge followings on social media told me that he supported Substack’s hands off approach to content moderation. He had been suspended and demonetized by Facebook multiple times for referencing his political opponents’ posts so he could criticize them. The bans always came at the hands of an AI that flagged content based on key words or specific language, regardless of context. It would sometimes take weeks to get a human’s attention to have the ban reversed. In the meantime, he’d lose the ability to reach his audience and make money. He was grateful that he doesn’t have to worry about that at Substack, not only because we don’t do heavy-handed moderation, but also because he gets paid directly by his subscribers, all of whom are on a mailing list that he controls. “I haven’t heard anyone talk about the content moderation issue from that angle,” he said. He wants to keep growing on Substack and asked for advice. I said he should look at Notes as an opportunity. It’s still in its early days, but Notes is already directly driving revenue growth for writers—in some cases, a note has driven thousands of dollars in paid subscriptions. 

Ninety minutes later in our office, over a wide table in a conference room, I talked to a rising star whose newsletter has become a cult favorite in New York. “I’m thinking of ways to expand to other platforms,” she said. “I see writers who have built big audiences on social media and then brought them to Substack and they have all these other revenue streams.” Most of her growth has come directly from the Substack network, so she’s interested to see how she can move outwards. Should she bring on contributors? Should she start a podcast? When should she try get some press coverage? I said she could consider doing more free posts—and make them her best work—as a way to find new readers and convince existing readers to become paid subscribers. A strong free post by a writer of her calibre and reach can drive tens of thousands of dollars of subscriptions. That has always been one of my favorite things about Substack: a writer can get a huge pay rise by publishing a great story. 

I went for a walk around Koreatown with a colleague who recently joined to help make our writer events awesome. So much stuff coming up. We’ll be hosting a night of readings led by a young essayist in some ornate church, and, because of some scheduling snafu the church had agreed to let us serve food and drinks in the sanctuary. There’ll be an intimate salon in an apartment in New York’s famed Dakota apartment building, where John Lennon was shot. We’d just decided to do a small event around live hate reads. A popular Substack writer will host a live game show based on pop culture trivia in a theater. 

Over lunch in a too-fancy restaurant that had trees growing inside it, I tried to convince a couple of writers, who had found refuge and security and ultimately better pay in Substack after losing their digital media jobs, that they should bring their large, ad-supported podcast into Substack so that it can sit alongside their other work and they can have a direct relationship with those listeners. “We quite like the idea of having a different type of revenue stream as a hedge, just in case,” one of them said. Understandable, I said, but I reckoned that the subscription revenue they would ultimately generate from bringing those listeners into their Substack community would quickly surpass their share of the ad dollars that they get from their podcast network. They’ve got so much growth ahead. I offered to hook them up with an agency that could help with them production and maybe even sell host-read ads for them. 

I enjoyed the crispy skinned salmon.

I’m on a train now, heading back to Washington DC, where my wife and I have brought our kids for spring break. I am tired. I am satisfied. This work is sometimes taxing on the heart, but it is good for the soul. I can’t wait to get back to New York.