How WhereByUs scaled its local newsletters to multiple cities

Christopher Sopher explains how his team developed a set of publishing tools and processes that can be launched in any city.

Every morning, tens of thousands of people who live in cities like Miami, Portland, and Pittsburgh receive a conversational email that updates them on the latest news within their city. These newsletters don’t often contain any original reporting, but they’ve been embraced by their local communities because they’re so effective at distilling dozens of newspaper articles, social media posts, and government announcements into an easy-to-read digest.

These newsletters are owned and operated by a company WhereBy.US. Launched in 2014, the company built out a scalable model that includes newsletters, self-service ads, and paid memberships. I recently interviewed its founder Christopher Sopher about how he built the company, its role within local journalism, and why he decided to spin off a SaaS publishing product that he sells to other media entrepreneurs.

To listen to the interview, subscribe to The Business of Content on your favorite podcast player. If you scroll down you’ll also find some transcribed highlights from the interview.

iTunesStitcher/  OvercastSpotifyGoogleYouTubeAudible

This transcript has been edited for clarity.

The founding of WhereByUs

Prior to launching WhereByUs, Christopher worked at the Knight Foundation, and his job involved visiting various cities to promote what’s called the Knight News Challenge. “The challenge would have a theme, and we would give out about $5 million each time to different projects. Some of them were tech. Some of them were startups that we would invest in. Some of them were nonprofits.” 

In 2013, the theme was open government, and while Christopher was visiting Miami he helped host an event with 400 people. “The topic was how we could make Miami a better place to live in through open government, which is perhaps the least sexy topic you could imagine for getting people to come and spend part of a Saturday, but the turnout was insane. We had these little group-facilitated sessions where people would get together and talk about ideas and brainstorm together. It's like a fun, collaborative session.”

The event opened Christopher’s eyes to the level of engagement that’s possible in a tight-knit, local community. “The initial idea that I came up with was to actually start a civic incubator, but it became clear pretty quickly that there was this opportunity around news and information, because every single month we would do this event and people would always pitch ideas that were about news and information and learning what was going on in the community and creating calendars and newsletters and websites.” 

Christopher  was working with two co-founders, Rebekah Monson and Bruce Pinchbeck, and the three eventually concluded that they could fill in a gap that local newspapers, TV channels, and radio stations had left open. “We launched a newsletter on January 5th, 2015, and we wrote it every day. A lot of days we’d fall asleep at the computer while trying to get the newsletter done at a reasonable hour.” 

Establishing a scalable format and business model

In the early days, the WhereByUs team simply cobbled together already existing products for producing and sending the newsletter, but they eventually started building out proprietary tech for distribution and self-service ad selling. “About 40 to 45% of our revenue comes from newsletter advertising that is either sold directly through self-service or at least facilitated by our software. We like to say that buying an ad on our newsletter is easier than buying a Facebook or Google ad.” The platform allows a potential advertiser to choose between CPM or flat pricing. “We're working on some new stuff around booking ads that allows you to also pay per conversion or pay per click, but our goal was to start with something simple that lets you put an ad in the newsletter on a particular date or series of dates, which makes it really easy for a lot of smaller and medium-sized advertisers to plan around because that's how they think about their budget.”

WhereByUs also launched a membership program for its newsletters. “We do a freemium model. We have the daily newsletter that is free for everybody, and then if you become a member, we do a special content section in each newsletter that's just for members. And then we do different kinds of virtual events and giveaways and programming for members. There was, frankly, a lot more happening around the membership program before COVID, and we're excited to get back to that. But we used to do a lot of events, a lot of meetup tours. A lot of it was about helping the local community explore the city. We had to move a lot of that virtual, but we actually saw our membership more than triple in 2020, because we went out to the community and said, ‘Hey, this membership program is really important right now, given COVID and the state of the advertising market.’ We saw a ton of growth and support from our readers through that membership program.” 

Expanding to other cities

WhereByUs launched its Miami newsletter in 2015 and then began replicating its model in other cities a year later. “We launched our second city, Seattle, in August of 2016. And then in 2018 we launched in Portland and Orlando, sort of expanding out geographically from those two coasts. And then in 2019 we bought Pittsburgh’s The Incline from Spirited Media and brought them into the fold.” 

By that point, WhereByUs had built out proprietary technology and a strong business model for delivering local news, and its founders began to think of ways they could make it available to outside organizations. So they developed a SaaS product called Letterhead. “We started working on Letterhead right after COVID hit, which is somewhat unintentional. Since the later part of 2019, we had a lot of conversations with people who were building newsletters, who would reach out to us and be like, ‘Hey, I like your newsletter. How do you do it? What tools do you use?’” At first, the WhereByUs team simply informed people that the technology was proprietary and not available to the public. “Eventually, we began to wonder, ‘is there a business here?’ And so we went and did some research and tried to learn what the space looked like.”

Even though there were plenty of email marketing tools on the market, there weren’t any built to solve the problems faced by local news publishers. “If you're a publisher, if you're trying to build a community around email, it's actually really hard to do that with a marketing tool. It's not built for it. So that was where the genesis of Letterhead came from. We spent basically the second half of 2020 building out the software, testing it with some early partners who were willing to come on and mess with it, and then in late December, we launched it publicly and have been onboarding folks since then.”

Do you like this newsletter?

Then you should subscribe here:

Simon Owens is a tech and media journalist living in Washington, DC. Follow him on TwitterFacebook, or LinkedIn. Email him at For a full bio, go here.