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 Jared Newman. Jared is a longtime tech journalist who’s written for Fast Company, PCWorld, and TechHive, the latter for which he’s written a weekly column about cord cutting since 2014. In 2016, he launched Cord Cutter Weekly, a weekly newsletter that helps people learn how to ditch cable TV and maximize their savings on streaming services. It now has more than 30,000 free subscribers, with weekly open rates above 50%. In 2018, he launched Advisorator, a newsletter that offers the kind of tech advice you’d hope to get from a geeky friend. Each newsletter has an in-depth advice column, some quick news hits, new apps to try, and deals. It now has over 1,000 paying subscribers.
Jared walked us through the products that are absolutely essential to his business:
This self-hosted newsletter software lets you send lots of emails for cheap using Amazon SES. I send about 140,000 emails per month and my bill from Amazon is about $15, several orders of magnitude lower than what Mailchimp or other email marketing services would charge.
I started using Sendy back before Substack was a thing, and before my newsletter had any kind of business model. While setting it up is more of a hassle than big newsletter platforms, I appreciate that it’s allowed me to stay independent without a lot of overhead. As a bonus, it offers an “anonymous tracking” feature that lets you view aggregate open and click rates without knowing what each individual user is up to.
Newsletter Glue turns WordPress posts into properly-formatted newsletters, which it then delivers via your email service provider of choice. In my case, it plugs into Sendy so I can post to my WordPress site and automatically send out the newsletter at the same time. It even has the ability to show content only inside the newsletter, or only on the website, which is helpful for things like embedded sign-up forms.
I should note that Newsletter Glue recently pivoted to focus more on newsrooms than individual creators (as reflected in its $1,440 annual price for new customers), but it’s a testament to the developers and their excellent support staff that they continue to help out small-timers like me.
In Advisorator’s early years, I had an extremely rickety sign-up page that plugged into Stripe via hand-coded PHP, and I had to manually process cancellations myself. Once I launched my WordPress site and needed to set up paywalls, Memberful was a natural fit. The “Pro” tier’s 5% cut and $25 monthly fee seems like a lot—though still less than Substack after a point—but not when you consider how well everything just works. The support team is also super responsive, and I appreciate being able to customize things like my “trial’s ending soon” email and “how’s everything going” messages.
A big part of my process involves collecting links to important stories, new apps, or other things I might want to write about in each newsletter. Raindrop has been my go-to bookmarking tool for years because it works on practically any device and makes it easy to sort links into “Collections.” I have collections for each newsletter, and the links become a kind of weekly to-do list.
Notion is where I stash all of my long-term story ideas and newsletter plans. What distinguishes it from most other note-taking apps is its ability to create and link to pages within pages. That means I can have a list of story ideas for Advisorator, and each individual idea can link to its own page with relevant links or thoughts, kind of like the structure of a website.
I’m the weird nerd who prefers working in Windows, and Beeftext is the best free text expander app I’ve used. It lets you type in short keywords to insert much longer words or phrases, effectively automating a lot of tedious typing.
This comes up in newsletter creation a lot. For instance, I have a shortcut that spits out my entire newsletter template in Markdown, another for the follow-up email I personally send to new paid subscribers, and shortcuts for each of my newsletters’ hex code color schemes.
All reader mail flows back to my regular Gmail inbox, where I inevitably spend a lot of time answering people’s questions. Simplify Gmail makes Gmail’s desktop site less of an eyesore, with extra whitespace and a nicer compose window. It also hides Google’s inbox ads and blocks read receipts. I’m stingy to a fault about software subscriptions, but this one (which costs $24 per year) I happily pay for.
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