Welcome to the latest edition of The Entrepreneur’s Tech Stack. I’m your host, Simon Owens. For those who don’t know me, I write a media industry newsletter you should definitely check out.

Today’s featured entrepreneur is Charlie Meyerson. Charlie is a veteran journalist who joined the Chicago Tribune’s internet team in 1998 and went on to run the newspaper’s email newsletter program. In 2017, he launched Chicago Public Square, a daily roundup of news relevant to the Chicago metropolitan area. The newsletter has been repeatedly named Best Blog in the Chicago Reader’s annual Best of Chicago poll. He’s also the cofounder of the Rivet Radio news app.

Charlie walked us through the products that are absolutely essential to his business:


Don’t laugh. Sure, it’s been around forever and, sure, Google gives it almost no love. But it’s free, relatively simple to use and it’s been rock-solid reliable since I began fiddling around with it in September 2005.

For my purposes, I could be writing and composing using any platform capable of generating an RSS feed—WordPress, Medium, Tumblr, whatever. But I’m comfy with Blogger.

Did I mention that it’s free?


I’ve designed a set-it-and-forget-it Chicago Public Square template in Mailchimp. Each day at 10 a.m., Mailchimp checks the ChicagoPublicSquare.com RSS feed. If there’s new content, it pours that content into the template and sends that edition. If nothing new, nothing gets sent. (I love that hard deadline—partly because it keeps me from dithering indefinitely over when and whether to press the “Send” button.)

It can be pricey—especially as circulation grows—but I was an early, free user back in 2013; its customer service is solid; and its click map is best-in-class. As I’ve learned over the years, such reports are an invaluable tool for fine-tuning editorial strategy.

Also, on those rare occasions when something has gone wrong, Mailchimp has on request credited me for a whole month’s service.


Since early 2018, I’ve used Memberful to collect financial support from Square fans—at first, on a monthly or yearly basis; and, since 2020, also via a one-time “tip jar” option that’s proven even more appealing to readers.

Memberful’s customer service is personal, quick and spot-on. It’s worth the monthly fee and the cut I share with it.

At the time I signed on with Memberful, I chose it over Patreon mainly because it didn’t demand the programming of a whole separate website. Patreon’s since bought Memberful but, mercifully, hasn’t compromised Memberful’s tremendously responsive support team.


For decades, this invaluable Mac text editing software has been my go-to for HTML fit-and-finish.

Just before Square’s publication, I use BBedit’s highly flexible find-and-replace powers to ensure, for instance, that bullet points are red and that Blogger’s passion for nonbreaking spaces is under control.

Newslit and TweetShelf

Sure, I monitor Chicago’s mainstream news sources, like the Tribune, the Sun-Times and local news broadcasts; and general news sites, including The Associated Press and the national papers and networks. But Newslit and TweetShelf are the “secret sauce” in Square—they bring that something extra to each edition. They scour the feeds of the more than 4,000 journalists and other reliable sources I follow on Twitter and send me frequent email alerts when a significant number of those sources share news. The result is a newsletter far smarter, more insightful and unpredictable than I could ever assemble on my own. Newslit and TweetShelf have recently been crippled by Twitter’s API fuckery; but Newslit, at least, was on the mend as of this writing.

Grammarly (free)

I can’t wholeheartedly join the fear and loathing of AI technology when Grammarly’s free AI-powered browser plug-in continually saves me from typing forego when I mean forgo.

Microsoft Edge browser

To my surprise—after trying so many others, including Safari, Chrome, Firefox and Opera—Edge works better than the rest, especially with Blogger on a Macintosh.

Specifically, it accommodates the vast library of Chrome extensions that Safari rejects—including Smart Punctuations, which backstops my anal-retentive preference for curly quotation marks. And—unlike Chrome, for instance—it plays nice with Apple’s text substitution preferences, which let me default to a Square-specific bullet-point, like this: ■

Google Domains

It points ChicagoPublicSquare.com to my Blogger blog.

It plays nice with Blogger, and Google makes domain management relatively simple.

$12 a year is a reasonable price—and, heck, I’m not paying anything for Blogger.

Zoom + YouTube

One great thing about an email newsletter is that it’s a platform for publishing anything and everything: Audio, video, photos, whatever. As a radio veteran, I can’t quit podcasting. This has proven a viable combo for producing audio and video interviews through the pandemic and beyond.

My teammates at Rivet and I tried a lot of alternatives—Zencastr, Clubhouse and (groan) Twitter Spaces—before determining that these two work together best to deliver solid audio, with easy editing of multiple channels for each speaker courtesy of Zoom, and video for those into that. (Sample here.)


As Simon’s explained previously in this series: It’s free and extensively customizable audio editing software. It works the same on all platforms, and support—just Google your question—is widely available. (But do yourself a favor and learn how to avoid hamhanded edits.)


Both as someone who finds paywalls counterproductive and also as a compulsive Creative Commons-friendly archivist who wants his work to live forever, I have no reservations about uploading Square audio to a free service whose mission is “to provide universal access to all knowledge.” I embed Archive.org audio on my website, in posts labeled so as to fuel a podcast RSS feed that I’ve aligned with various podcast vendors. (Example here.)

Apple Keynote

I have a template whose default image export dimensions match those of Facebook and LinkedIn, so graphics I create there look pretty when Square gets shared across social media.

It’s free (for Mac users, anyway) and it works well—especially once you get used to its idiosyncratic controls.

Smooze Pro

This Mac app has given new life and functionality to my vintage Kensington Expert Mouse Pro trackball, letting me mount my MacBook Air on a laptop stand and improve my typing posture—at least a bit—as the doc has recommended.

Google Assistant + Google Nest Hub + various music services

This combo lets me “Turn on the desk,” “Set the thermostat” and “Play music by _______”—to make the writing process as Star Treky and pleasant as it can be, given that so much of the news these days is unpleasant.

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Photography by Steve Ewert


Simon edits an industry newsletter that covers everything from the Creator Economy to traditional media. He also hosts The Business of Content, a podcast about how publishers create, distribute, and monetize digital content.

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