Chicago Public Square: Keeping Chicago informed and winning awards along the way

Jun 9, 2020
Charlie Meyerson

Hi there! Who are you and what's your background?

Thanks for asking! I'm Charlie Meyerson. I majored in journalism at the University of Illinois and spent the first couple of decades of my career in radio news, whose minute-by-minute focus on audience attention made for a good fit when I jumped to news on the internet — at the Chicago Tribune — in 1998. There, I launched and managed the Trib’s email news programs — including its breaking-news alerts — for more than a decade. I wrote each daily email news roundup like a radio newscast. Since leaving Tribune Co., my work has taken me through a string of award-winning digital startups — including Rivet, where I’m (part-time) vice president of editorial and development, and my own personal 2017 startup, Chicago Public Square.

What’s your newsletter about?

I call Square “Chicago’s new front page.” The idea is to deliver essential and compelling information for people who care about Chicago, the region, government and politics, business, technology, the environment, journalism and the media.


When did you get started writing your newsletter? What motivated you to get started?

The idea came to me in January 2017, when I had some time on my hands and the nation faced a significant political transition. One friend, a working mother I’d known since she was in high school, sent me a message on Facebook:

“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 need to stay informed, but I need to work, too. If there is a resource you have found or you are doing one, please let me know.”

Well, I had two thoughts: 1. Hey, I know how to do that. It's a newcast! 2. What have I for years been recommending to job-seekers and others with too much time on their hands? Start a blog and Just Do It. So I just did it, building Square on the free Blogger and MailChimp’s free starter package — until the growing number of subscribers pushed me into MailChimp’s paid service, by which time a few ads were enough to cover expenses.

What does the process of writing your newsletter look like for you?

I get up each morning around 7 and — just like everyone else — grab the phone and check it for email, Facebook and Nuzzel updates overnight. (Nuzzel is my secret weapon.) Then I get the morning papers off the porch, pour some Trix into a cup and head up to my desk to begin writing. I’ve set up MailChimp to scrape automatically at 10 a.m. — because I love the thrill of a deadline and because, without a deadline, this work would never end.

What are some of the difficulties you’ve encountered in running your newsletter?

I wouldn’t call them difficulties, but Job No. 1 has remained from the start: Get more (free) subscribers.

What have you learned through writing your newsletter?

I learned this long before launching Chicago Public Square, but: Readers’ attention is not to be taken for granted. Their priority is fundamentally opposed to publishers’ and broadcasters’ priority: We want them to spend all their time with us, and they want to get on with their lives. In email — as in radio news — every word counts. Keep it short and let your links do the heavy lifting. When you link profusely, you gain insight from your audience on what it finds most interesting.

What do you do outside of writing your newsletter?

My role with Rivet keeps me engaged with the audio news and podcasting field. I look forward to spending more time with my growing family — when the coronavirus menace fades. And I’m lately trying to binge my way through the raft of CBS’ recent Star Trek shows.

What’s your favorite part about writing your newsletter?

I love checking MailChimp metrics to find out which of the many links in each issue my readers found most interesting. That makes me a smarter, more engaging publisher every day. And it’s been a kick to collect a few awards along the way: Honors for Square in the last year include Best Blog and Best Visual Artist for contributor Keith J. Taylor in the Chicago Reader’s Best of Chicago poll, and Best Blog (Independent) in the Chicago Headline Club’s Peter Lisagor Awards for Exemplary Journalism; in 2019, a limited-run daily Square audio news roundup took the Lisagor for Best Radio Newscast, defeating venerable all-news station WBBM.

Do you have a monetization strategy for your newsletter?

Already in place: Memberful has been a great partner since the launch of a Square rewards program in February 2018. More than 14% of my subscribers have (as of June 4) volunteered to pay an average of $6.70 /month just to keep me from quitting. And, as a participant in a joint monthlong campaign with more than three dozen small and independent news organizations under the Chicago Independent Media Alliance banner, Square over the last month helped raise a total of more than $160,000 from more than 1,000 individual donors — including matching funds from foundations — to support and demonstrate the power of local media.

How do you grow your audience?

Step 0, as I call it, is to get a lot of friends — on social media and in real life. They are your core audience, your prime advocates and referrers in the process of building an audience. If you’re lucky enough, as I am, to have a few friends in the media, being interviewed can be a great driver of subscriptions.


Photo credit: Harry Carmichael

What newsletters are you subscribed to?

As many news- and Chicago-centric newsletters as I can find. So all the local news newsletters and many of the mainstream national newsletters, too. But I’m also a fan of Brian Stelter’s Reliable Sources email for CNN. And I’m a late discoverer of an excellent roundup of academic perspective on the news, The Conversation.

What goals do you have for the future?

Get more (free) subscribers.

Where can readers go to learn more about you and your newsletter?

Read it: Subscribe (free):

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