Christopher Sofer is the co-founder and CEO of Letterhead, a platform that offers business tools for newsletters. He’s also a newsletter industry veteran. Sopher launched his first newsletter, The New Tropic, in Miami in 2014, aiming to help members of his community understand their city more deeply. Over the next six years, that newsletter grew into a network of local newsletters now spanning cities like Miami, Seattle, Portland, and Pittsburgh called Whereby Us. In total, Whereby Us earns $1.5 million in revenue annually.
Here, Sopher shares his strategies for growing a local newsletter, developing authentic communities, and working with advertisers. His answers have been lightly edited and condensed.
Why did you start with a local newsletter?
We identified a need around community for locals. We would meet all these people in Miami, this growing place with a lot of people moving there, a lot of natives returning back to Miami, and people who grew up there and spent their whole lives there. It was this moment when all of this stuff was happening in the city, and there was all of this growth. It felt really cool and exciting to be in Miami, and it still does.
But we would meet all these locals who were like, ‘I don't feel like I'm plugged into what's going on. I'm excited to be here, but I don't really understand what's happening.’ Or, ‘I'm barraged by information, but I don't feel informed.’
We recognized there was this sense of community and belonging that people were really craving. Traditional local news, like from the newspaper, is not designed to do that.
So we saw an opportunity to make a contribution. Our initial business plan was not just a newsletter. We were going to do events. We were going to open a bar. We were going to do all these other kinds of things. As we went, we did some more research and we peeled back some of those elements. We decided this would be a newsletter first, and we could build a community around it.
The reason we picked email was we spent a bunch of time doing research, digging in with people about their day. We learned where they were consuming information. When people roll out of bed in the morning, they check their email. They read their email when they’re on their way to work, they read their email when they get to the office, and when they’re wrapping up for the day, it’s the last thing they check.
How can creating a newsletter improve someone’s sense of, ‘I read everything yet I know nothing?’
It's a great question, because obviously if one of your insights is that people are overwhelmed with content, deciding to add more can be an odd choice.
But email is really useful for that for a couple of reasons. One reason is that it's so choice oriented. It's very respectful of choice if you do it the right way. (Obviously there's a ton of spam email that is not respectful of you as a recipient) but I think newsletters as a product are pretty good about this. You choose to subscribe. Lots of tools require double opt in. It sits there in your inbox. A lot of people filter it or send it to a different folder, and you can open it when you want to, you can finish reading if you want to. And if you want to, you can block the images if you don't want images or ads to appear. You can control so much about the experience. When it's done well, email can be a really high prized piece of information.
Something else we do is respect our readers' time. We want to keep it really short, right? There's always going to be motivation to make your product way too long. Keep it short and simple. Don’t make it too heavy with text, or too difficult to navigate.
Last, how do you make sure there is enough variety in what you're highlighting and the way you're approaching it—like little bits of treasure that people can find along the way—that it is a unique experience every time? I think that's a really crucial part of it. If you're just sending, ‘Hey, here's the top 10 articles today,’ that's sort of lazy email strategy. Sometimes that's what you want to do, but if you're trying to really build a community, I think you have to be a bit smarter than that.
And when you put in that effort to make each day’s product unique, that's reflected back in the engagement you get.
Whereby Us is ad supported. Does creating a strategy for ad sales ever conflict with delighting readers?
If you are in a place where you have to choose which of those things comes first, the business isn't set up correctly. If it feels like there is a choice between what is in the interest of advertisers and what is in the interest of readers—that those things are at some level mutually exclusive or opposite, that they’re pulling in different directions—that's a signal you haven't lined up one or both sides of that equation.
Here's how I think about it. If you're building a community of really tightly engaged, niche, high-value readers, and your advertisers are trying to sell basic consumer goods, like paper towels, it's never going to work, right?
Paper towels are a super low cost item. Advertisers like Proctor & Gamble, or any other big brand, are aiming for lowest dollar reach. They’re asking, ‘How can I reach the broadest audience possible?' Because everybody buys paper towels, right? It's a completely different mentality than what I, as a publisher of a small niche audience with good engagement numbers, am looking for. There's a fundamental mismatch there. Maybe I can still get them to buy the ad, maybe I can get that initial sponsorship contract, but they’re going to push for growth. They'll want to know: ‘How can we get more subscribers? How can we get more clicks?’ And that may not be what’s best for your audience.
So if I have a really high engagement, niche audience, I’m looking for sponsors who are aligned around these questions: “Who are the people who are subscribed? What matters to them? Is your newsletter a brand that they trust?”
It’s really hard to get right, and something we see a lot of folks wrestling with. At Letterhead, we're having a lot of fun right now helping other publishers think through those things and kind of figure out their strategy. Ad sales is a thoroughly unsexy thing, and most content creators don't get in the business because they want to sell ads, even though it's a really valuable part of the business. Now, that’s part of where we're trying to make a contribution to the space.
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