Tell us a bit about yourself and your background.
My name is Jamie Thingelstad, and I'm a technologist, leader, and builder who has been creating on the web for nearly as long as it has existed. Professionally, I serve as the Chief Technology Officer at SPS Commerce. I've been leading technology teams for almost three decades, building companies, platforms, and products. I've always been drawn to building things.
Writing on the web has been part of that building since I started my blog over 20 years ago. My blog has evolved over multiple platforms but has always been aligned with what we now call IndieWeb principles. I currently use micro.blog for that. When writing online, I believe that if it is not your domain, it's not your words. I advocate for online privacy and want to keep algorithms out of what I read. I long ago abandoned social media, which I see as the antithesis of these principles. Newsletters are a way around that.
I live in Minneapolis with my family and our dog. We also do fun local projects like our Candle Fundraiser and the 612 POAP Challenge. I generally like to play with tech and explore topics. Having a career in technology means continuously learning, and writing my newsletter, the Weekly Thing, is a way I share that process.
I was once told the Weekly Thing is like having a direct feed into what I find interesting — and that is pretty accurate.
What do you write about in your newsletter?
I think the Weekly Thing is somewhat unique amongst newsletters. It isn't about a specific topic; instead, it's about sharing my learning journey. Topics evolve over time. It is a blend, containing curated links and commentary alongside my blog posts and a photograph from the week, and more.
I've been publishing the Weekly Thing for eight years and have over 330 issues. There are recurring themes: privacy, productivity, leadership, artificial intelligence, and more. I've asked readers what 1-word captures how they think of the Weekly Thing:
Informed, Smarter, Worthwhile, Positive, Insightful, Curious
I was once told the Weekly Thing is like having a direct feed into what I find interesting — and that is pretty accurate.
The Weekly Thing also completely ignores a lot of what "growth hackers" might say you should do in your newsletter. It is long, has a lot of depth, and I don't intercept any of the links that people click on. If Google feels that it shouldn't land in your Inbox, that is on them, not for me to change how I express myself.
Where did you first learn of Buttondown, and what made you decide to give it a try?
The Weekly Thing originally started on the ill-fated TinyLetter service. It was a good place for me to get started, straightforward, but ultimately too simple. You could not even schedule a newsletter on TinyLetter! MailChimp had acquired TinyLetter, and I knew it had tons of powerful features, so I decided to switch to it. I could schedule emails, but along with the power came so much complexity. I had to deal with an incredible mess of HTML to create "campaigns", not newsletters. After using MailChimp for a while, I just got tired of using a marketing platform for a newsletter. It was the wrong solution.
I decided to look around and wanted something that aligned with IndieWeb principles, offered a much simpler authoring environment, had an API that allowed me to automate tasks, and had robust newsletter-focused capabilities. The fact that Buttondown allowed me to author entirely in Markdown was a massive win over the HTML I had previously been navigating.
I started publishing with Buttondown in Jan 2020. For over 5 years, Buttondown has been the platform for the Weekly Thing. I'm now hosting three additional newsletters on Buttondown, too!
Buttondown fits with my values: open, simple, private, built to stay. It allows me to express myself and create an online community.
What are some ways Buttondown has helped you run your email?
Let me touch on the biggest ones…
- Markdown support is a big deal for me. I author the Weekly Thing by creating dozens of "blocks" of Markdown. Then an automated process assembles those blocks into each issue. Being able to author everything in Markdown and then easily pull it all together is enormous and keeps things easy for me.
- The Buttondown API is critical as it allows me to automate moving my draft newsletter into Buttondown and getting all the metadata set exactly right. I use the API to add metadata for subscribers. I share an annual POAP token with my readers, and to do so, I need to load a unique claim URL into each subscriber's metadata, which I can easily do via the API.
- I recently launched my Supporting Membership program using the paid subscription feature of Buttondown to raise money to support digital non-profits each year. This year, we are raising money for the Electronic Frontier Foundation, and Buttondown's features make that work. Using the combined APIs of Buttondown and Stripe has allowed me to automate much of this, along with AI.
In addition to those, I've done some fun experimentation with surveys, using them more as a way to engage with readers and create content together.
Oh, and it was cool that Buttondown congratulated me when I got to 1,000 subscribers.
Anything else you'd like to add?
I've been writing online for decades, and the Weekly Thing is now one of the main ways that I share what I'm learning about and exploring. Buttondown fits with my values: open, simple, private, built to stay. It allows me to express myself and create an online community. I want to see more IndieWeb-friendly publishing platforms as they proliferate.
If you want to read more, check out How to Newsletter: Lessons from 300 Issues of the Weekly Thing.