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 Jacob Feldman. Jacob has been working in sports journalism for over a decade and is currently a business reporter at Sportico. In 2014, he and ESPN writer Don Van Natta Jr. launched The Sunday Long Read, a newsletter that curates the web’s best stories every week. For each issue, the two co-founders narrow down a list from dozens of nominees and write short blurbs about why each piece stood out.

The Sunday Long Read is monetized through a mixture of sponsorships and paid memberships. “We’ve been thrilled to add more than 30,000 readers and writers to our community over the years,” Jacob told me. “We’re proud of an open rate currently north of 50% and excited to say we generate more than 15,000 clicks on fantastic pieces of storytelling each week.” He and Don now collaborate with more than 100 outside contributors who help in the production of the newsletter and accompanying podcast.

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

Mailchimp / WordPress / Memberful

This trio of platforms, while not the newest or most exciting, have proven to provide the best foundation for our business. Mailchimp continues to offer the most complete newsletter design and editing functionality (even if the platform isn’t optimized for our editorial model). WordPress is, well, WordPress. And Memberful has made it extraordinarily easy to launch a membership line of revenue, with support response times that continuously amaze me. I’d be lying if I didn’t say I’m often exploring potential replacements for each of these services, but they have all proved irreplaceable for years now. You could add Google’s suite of apps to this list too—an embarrassing amount of The SLR’s knowledge and workflows live there in one form or another. 

OK, now the fun stuff…


I manage email in Superhuman after years as a Spark evangelist. It’s fast and has good search, easy-to-build email response templates, and a quick way to snooze emails or create follow-up reminders. It helps that I’m on their education pricing plan, which I recommend checking out in case you might be eligible!


Before my words go anywhere, they go in Tot, a super simple Mac menu bar app (with an iOS companion) that offers seven little sticky note-like pages to drop text into. It’s basically always open as I plan my day, take meeting notes, brainstorm ideas, and so on, before moving that information into longer-term storage.


My clipboard manager of choice was, I think, the first thing I downloaded when I set up my newest computer. I can’t imagine living without it. Search is great for finding that nugget I copied days ago, and I can save certain clipboard items in handy tabs (like The SLR’s brand colors’ hex codes) for super-fast access. Being able to quickly copy multiple things and then paste each in the right place feels like a superpower. 


An improvement on macOS’ Spotlight feature, Raycast helps me resize my windows, quickly access notes or contact info, or run simple math equations. But what really makes it powerful are the extensions, which I use weekly to create Bitly links, encode URLs, and so on.


As The Sunday Long Read transitioned from a fun little newsletter into a full-scale business, I was pretty lost when it came to financial tracking, planning, and so on. A bunch of tools now help us manage those aspects of the enterprise, but Wave is my easiest recommendation to entrepreneurs or small teams in need of simple accounting tools. Honestly, it probably has a lot more functionality than we’re currently leveraging. 

Want to be featured in a creator spotlight like this one?

Each interview is heavily featured in front of my 14,573 newsletter subscribers, and I share it out to my 70,472 social media subscribers.. Go here to contact me and tell me a little more about your business. 


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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