This newspaper veteran launched his own Chicago-focused newsletter, and it’s thriving

Simon Owens
Oct 29 · 8 min read

Charlie Meyerson had the kind of background that was perfect for launching a Chicago-focused newsletter. While majoring in journalism at the University of Illinois, he worked at the student radio station, and his first job out of college was at a station in the Chicago suburbs. In 1998, he made the leap to the Chicago Tribune, and he ran the email newsletter program there for a decade.

It was about eight years later that he launched Chicago Public Square, a daily newsletter that now counts thousands of subscribers. It’s formatted as a simple news digest, something that can be scanned quickly before a reader goes about their day. It’s won local awards and managed to convert 15% of its free subscribers into paying members.

I interviewed Charlie about his process for compiling the newsletter, how he attracted his initial subscribers, and what lessons other potential local news entrepreneurs can learn from his success.

What years did you run the newsletters at Chicago Tribune?

1998–2009.

So you were on the editorial newsletter scene extremely early. How powerful were newsletters in terms of driving traffic and attention to the Chicago Tribune’s journalism?

Very little on the internet was “powerful” in those early days — I remember that a senior newspaper (print) editor told a senior web editor: “My reporters will never write anything for your website.”

But by the time I left, Daywatch — the Trib’s signature email newsletter — was reaching 60,000 readers a day, and those readers provided daily intelligence on what stories were resonating with the company’s most engaged readers. It also provided early and influential insight on what made for compelling, effective headlines — a subject on which I became an internal authority.

I should also mention that that reader feedback helped make Daywatch the most engaging editorial email company wide. At a time when the Chicago Tribune was co-owned with papers including The Los Angeles Times, Newsday, and the Baltimore Sun, Daywatch led all in engagement, with an average of 60 clicks per 100 readers.

Tell me about how you started to think about launching your own Chicago-focused newsletter.

In early 2017, I’d stepped back from my day-to-day role at Rivet (where I was and remain VP/editorial and development) and had some time on my hands. Donald Trump’s ascendance made clear journalism faced a challenge unlike any since the days of Watergate — an era that cemented my passion for journalism.

I wanted to play my part, and friends made clear they were desperate for help sorting through all that was happening. One — a young mother I’d known since her high school days — wrote this: “Every time I looked at Facebook or Twitter today, terrible things were happening in our government. Is there any news source that is keeping track of things that are happening day by day? Just in a bullet-point form? I feel like these days might go like this and I don’t want to miss actual happenings.”

And I thought: “Huh. I know how to do that. And, over the last couple of decades, what advice have I given journalists who have a passion to communicate and time on their hands? Duh: ‘Start a blog and send it out by email.’” So I did.

You decided to keep the newsletter relatively short with very quick summaries. Why did you decide to go that route versus longer articles and summaries?

1. That’s the best format for serving busy readers like those who helped inspire this project. Give them just enough information to know what’s happening while creating just enough of a “curiosity gap” to encourage them to read more.

2. Links provide tremendous editorial insight that so many wordier services leave on the table. Newsletters that provide long, linkless passages miss out on cues that indicate which words, phrases, and subjects the audience finds most intriguing — intel that helps make future editions even more engaging.

How did you find an audience early on? Where did you find your initial subscribers?

Initial subscribers came from my large pool of friends and connections on Facebook, Twitter, and LinkedIn. I’ve been promiscuous on social media over the years — careful always to connect with real people, of course, but always happy to link with anyone with a real connection to my profession, my town, my family, and my personal passions. This is why I’ve given my journalism students over the years an extra point on their final grade for every 20 authentic humans they gain as Twitter followers over a semester. That audience is real capital they can carry from job to job, project to project.

But other surges in subscriptions came from mentions and appearances on the radio. And in local media, notably Chicago media critic Robert Feder’s blog.

Walk me through your daily process for researching and writing each day’s newsletter.

The alarm goes off at 7:15, but I’m often awake earlier, because my wife’s goes off at 6:30 or so. Like most humans, I grab for my phone, check Facebook, email — I get a zillion email alerts and newsletters — and what I consider the “secret sauce” of Chicago Public Square, my Nuzzel app. Nuzzel combs through the feeds of thousands of people that I follow on Twitter and serves up a list of articles they’ve shared — ranked as I choose. (My default is “shared in the last two hours,” in descending order of the number of friends who have shared it.) Because I follow hundreds and hundreds of journalists, Nuzzel is often my first source for breaking news.

By about 7:45, I’m at my desk — armed with print editions of the Chicago Tribune, the Sun-Times, one cup of milk or orange juice, and one cup of really sweet cereal. (Trix is my favorite. Don’t judge me; it used to be Special K or Cheerios before the pandemic, but hard times have pushed me to the dark side.)

I sift through the email, Nuzzel, and the papers, noting stories worthy of inclusion in the newsletter, jotting down a few words as placeholders in my Blogger template. Once I’ve completed that process, I begin looking for ways to weave them all together — ideally grouping them into a lead item and one or more related sub-items. I think of each cluster as a print page or a subject section: Environment news, Chicago politics, national politics, the pandemic, etc. And, of course, those all overlap and so the hard part is deciding whether, for instance, Trump’s latest lies go with pandemic items, or national politics, or (if he’s talking about Chicago) local politics.

The actual writing and weaving goes on until about 9:30 or 9:45, when I make a last check of email and Nuzzel to see what’s breaking, arrange or re-arrange sections to see if I have them roughly in descending order of importance, engagement or (ideally) both. Then I review the zillions of cartoons the great Keith J. Taylor — whose work with Square in 2019 earned him top spot in the Chicago Reader’s Best of Chicago Poll for Best Visual Artist and made him a co-honoree in Square’s Chicago Headline Club Peter Lisagor Award for Best Independent Blog — sends me every day to see which fit best with what I’ve written. I insert his work, link it back to his Facebook page, and run my text through BBEdit for some typographical niceties (those little red square bullet-points, for instance). I paste it into Blogger and press Publish.

Then MailChimp scrapes the website promptly at 10 a.m. and sends out whatever is there. I love the thrill of a deadline. And I value deadlines because without them, work on the internet would never be done. It’s the biggest difference between analog and digital news. In broadcasting and newspapers, you’re done when the clock strikes 9 or when it’s time for the presses to roll; you can only do what you can do in the time allotted. If I didn’t have a digital deadline, I’d be tweaking and updating forever.

How do you monetize the newsletter?

I’ve been fortunate enough to have a few advertisers — and, frankly, I’d like more. But the ad industry is fat and lazy and has not figured out what to do with small, engaged, and focused audiences like mine. What’s been pleasantly surprising has been readers’ embrace of the “Help keep this coming” model, which I launched about a year after Square’s debut. About 15 percent of my audience is ponying up an average of almost $7/month just to keep me from quitting. I’ve been delighted with the services and support offered by Memberful in setting this up.

How do you find advertisers?

I periodically run promotional ads in Square and make suggestions on social media. Most of the advertisers in Square so far have been themselves devoted readers.

What lessons do you think can be derived from your newsletter that can help fuel a more robust local news ecosystem? Obviously, local news is suffering right now; do you think lean startups like yours could expand to pick up more of the slack left by shrinking newspapers?

Yes, indeed. I launched Chicago Public Square with virtually no out-of-pocket expenses.

I created it not only to scratch my creative itch, but to demonstrate to others how they can bring intelligent coverage to any subject matter, whether it’s a small community, a big city, or a specialized subject matter.

And although I think one of Chicago Public Square’s strengths is its news-source neutrality — I can link to any news org I want, without obligation to favor a “home team” — the model works just as well to promote any organization’s own coverage, as I demonstrated at the Chicago Tribune. (Where I eventually fought for and won the right to link to other news orgs’ sources, although that practice ended after I departed.)

So, yeah, I recommend any person or team looking to launch a news organization for any place or subject begin with an email newsletter, and build out content from there. There’s a reason I call Chicago Public Square “Chicago’s new front page”: It is a front for whatever I choose to put behind it, whether it’s news from other organizations, or work I create on my own, as I’ve done from time to time.

Should resources increase to an appropriate level, there’s no reason we can’t build a larger news organization under (or behind) that front page.

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