Crypto
- Do not use bullet points unless the speaker clearly uses them.
- Preserve all first-person phrasing and casual language.
- Remove filler words like ‘so’, ’like’, and ‘kind of’ unless they assist readability.
- Ensure the article can stand alone for publication.
- Feedbin: This is where all my RSS feeds live–around 300 of them. It’s fast, stable, and does exactly what I need. For $30 a year, it’s an incredible value. No fluff, just the right features.
- Unread: This is the mobile app I use to actually read those feeds. It’s ridiculously fast and makes getting through content frictionless. I don’t want to waste time loading or tapping around.
- Safari: Specifically for the Reading List. I like that it’s integrated across all my Apple devices, and it’s a really handy staging area between “that looks cool” and “this is newsletter-worthy.”
- Pinboard: The workhorse. I have over 15,000 links in there and it’s still lightning fast. It hasn’t been updated in years–and I love that. No surprises. It’s rock solid.
- Drafts: This is where my text starts. It’s not a notes app. It’s a place where text goes to live temporarily, get processed, get acted upon. I have a system in there for my Currently section, where I jot down stuff throughout the week.
- Data Jar: A magical tool. Think of it like shared memory across Shortcuts. Shortcut A writes something, Shortcut B can read it. Without it, this whole thing would be way more complex to stitch together.
- Shortcuts: This is the engine. Every section of the newsletter is its own Shortcut. The Build script just stitches them together. It’s modular, easy to extend, and Apple keeps improving it.
- Buttondown: The sending platform. I used Mailchimp for a while, and it made me feel like I needed to be a marketer. Buttondown talks like a newsletter author. It supports Markdown, doesn’t try to get fancy with HTML, and keeps things straightforward.
- OmniFocus: My GTD backbone. I track everything in here, and it gives me clarity on what needs to be done and when.
- Stripe: This is tied to Buttondown to handle Supporting Memberships. Super easy to set up, and now I’m raising funds for digital nonprofits through it.
- OpenAI: New to the stack. I’m using it for help with subject lines, fortunes, and membership messaging. But always with control–I want it to help, not replace my voice.
- Lou Plummer on School Starts in August
- Chris Shaw on Renewal
- Marisabel Munoz on The Promise of Dawn
- Sarah Gebauer on Spiraling up and down
- Mike Sass on Renewal
- Molly on (Book) Renewal
- Sara Jakša on The Space to Breathe
- Reilly Spitzfaden on Renewal
- Sacha Chua on Renewal
- Juha-Matti Santala on Resisting the urge to rewrite the website
- Ken wrote about Neighbors
- Nick Simon wrote on Slow Renewal
- Daryl Sun on Renewal
- Fractal Kitty wrote deep in the sitka
- Lianna posted on Libre Town Renewal
- Frank Meeuwsen on Renewal
- Manu Moreale on Renewal
- Annie Mueller on Before the next beginning
- David O’Hara on Renewal
- Arunkumar Bhat on Renewal
- Steve Ledlow on Renewal
- Andrea Contino on Renewal
- Joe Crawford on Reboot, Renewal
- Jamie Thingelstad on Musical Renewal
- Martín Morales on Renewal
- Josh Ellis on Renewal
- Do not use any words from the title of the publication. Only use words from the name of this article. Typically there is a hyphen or pipe between them.
- Using alliterations can be fun but not necessary. Do not always use alliterations.
- Try to pick a set of words that pique the readers curiosity. Words that are punchy and thought-provoking.
- Avoid words that are negative or sad.
- Acronyms are fine to include.
- Be creative and have fun.
- Keep it positive, fun, and interesting.
- Pull in themes or terms from the headlines of the articles included in each issue. Do not use terms from the title of the publication. Only use words or topics from the subject of the specific article.
- Avoid negative themes or topics.
- Fortunes should be short, no longer than 8 to 10 words.
- Feel free to include an emoji if it makes sense.
- Keep it personal and not overly marketing driven or too sensational.
- Focus on it being descriptive and use second person voice.
- Avoid overly sensational words.
- It is okay to use emoji if appropriate.
- Focus less on the quoted text.
- You don’t need to introduce it with statements like “this week” and can focus just on the content.
- Keep it brief and terse, shorter is better.
- There are currently «Premium Count» Supporting Members.
- We have raised «Amount Raised» so far.
- The funds will be sent to the non-profit for the year in «Weeks Remaining» weeks.
- The non-profit this year is «Non-profit Name».
- There are currently «Premium Count» Supporting Members.
- We have raised «Amount Raised» so far.
- The funds will be sent to the non-profit for the year in «Weeks Remaining» weeks.
- The non-profit this year is «Non-profit Name».
Collected POAP 7368637 for Campbell Mithun Tower — 612 POAP Challenge.
612 POAP Challenge: Collect them all!
Way back in the day I loved Geocaching. It was so much fun, particularly before it got commercialized. It was a way of exploring the area around you and finding cool, hidden things. 🗺️
When I first found POAPs the capability to claim a POAP for a location was something I wanted right away, and now you can with location drops! I created my very first location POAP and even recorded a video claiming it. Awesome. I wanted to make something with this. 🤔
Then I connected the dots between the 612 Series NFTs which I have a complete collection of. You may remember I also interviewed Erik Halaas who created it. This was perfect – peanut butter and chocolate moment! ✨
Thus the 612 POAP Challenge was created! 😲
If you live in Minneapolis join in and go collect some of these locations. The event runs until Labor Day. I think this will be a fun summer activity! Get the whole family involved on some walks, bike rides, kayaks, and explore the city. I collected my first one this morning! 🧭
I love that I was able to create an entire activity on the POAP platform. 🤩
PS: Please spread the word to others so we can get a bunch of folks playing along!
Screen recording at Lake Harriet claiming the very first POAP of the 612 POAP Challenge!
Finished 4.05 mile walk in 73.1 minutes (18.05 min/mile). It was a delightful morning for a walk with great views and feats of strength. I also collected the very first POAP of the 612 POAP Challenge to officially kick off a summer project — see the moment! 🚶♂️
Collected POAP 7364397 for Lake Harriet — 612 POAP Challenge.
I created my very first location-based POAP. Our “Peanuts Tree” is a popular spot on Cannon Lake and you can now mint a POAP if you visit it. I’m going to place a QR code by it so visitors can get more info. Will anybody do it? I don’t know, but it is fun either way. See screen recording of mint.
Screen recording claiming my very first location-based POAP.
The Summer of 2025 Magic Pines POAP is now minting! Available for visitors until Labor Day. 🤩
Related: Magic Pines Summer POAPs for 2022, 2023, and 2024.
How to Newsletter: Lessons from 300 Issues of the Weekly Thing
This is an article version of the presentation I gave at Minnebar 19 on How to Newsletter.
To create this I used Whisper Memos on my iPhone to capture the transcription. I did some general editing to remove some preamble and ad hoc dialog, did a read through to correct any obvious issues, and added images for each of my slides. I then asked GPT o3 to use the transcription to create an article using this prompt:
I have a raw transcript of a talk. Please convert it into a well-structured written article that preserves the speaker’s voice, tone, and all content exactly as it was spoken–do not omit or add anything. Improve readability by correcting grammar and sentence flow, organizing content into appropriate paragraphs, and inserting section breaks that follow the speaker’s original structure. Do not turn this into a summary or reinterpret the ideas. Use images from the transcript as section markers when available. Maintain the informal, personal tone of the speaker throughout.
With a proofread here is that version of this presentation.
What I wanted to talk about is “How To Newsletter.” I’ve been sending a newsletter now for eight years, and I’ve learned a lot in that process. I thought it’d be fun to share that knowledge. I actually planned to do this session in 2023–so if you’re thinking, “Didn’t he already do this?”–I had to cancel it that year. Now we’re two years later, and I’ve got two more years of learnings and 50 more issues of my newsletter under my belt.
As I put this talk together, I realized it’s not just about how to newsletter. It could also be about how to run a complex side project, or how to consistently do something for eight years. It’s also about how to apply automation to make that kind of work easier. So, depending on what you’re looking for, you might take away more than just newsletter tips–this is also about managing a long-term, detailed endeavor.
First, who am I? I’m Jamie Thingelstad. I’m a passionate technologist. I’ve been into tech since I was a kid, started programming BASIC on a TRS-80–you can figure out my age from that–and I’ve always loved building things. I’ve had a 20+ year career as a Chief Technology Officer, came into the field as the web was being born, built a couple of companies, and eventually started building things with groups to do even bigger work.
I’m on the board of the Minnesota Technology Association and previously served on the board of Minnestar. I live in Minneapolis with my wonderful family. I’ve also been a blogger for 20+ years–which plays a big role when we talk about newsletters–and I’ve been publishing The Weekly Thing for eight years now.
Why a newsletter? What led me to start The Weekly Thing? The image here shows the very first issue from May 13, 2007–it looked totally different from current issues. The one shown here is issue 316 from two weeks ago.
Back in 2017, newsletters were having a moment. People were launching them, companies were seeing them as a way to go directly to inboxes and bypass platforms. That intrigued me. I’d been blogging for over a decade and wanted to play with the newsletter medium. But then came the question: what would I put in it?
I’ve always been a voracious consumer of online content. I used bookmarking services like del.icio.us (anyone remember that?) and later Pinboard. My first bookmark is from August 2005. At one point, I thought about making a link blog, but it didn’t vibe with me. So I combined that impulse with the newsletter idea and decided I’d curate and share content I found interesting each week.
Importantly, I ignored most of the newsletter “growth hacks.” I’m cynical about stuff like that. I just wanted to share good content, without any tricks. I didn’t have a specific topic, but I committed to doing it for a year. Now, eight years later, it’s still a fun and meaningful project, and I feel like I’m giving back by sharing useful information.
The first thing I had to solve: how do I find content? For me, it’s RSS. I’m a huge fan. I don’t get content from social media–it’s all RSS feeds and readers like Feedbin and Unread. No algorithms. I scan headlines efficiently and ask one question: is this interesting?
If yes, it goes into my Safari Reading List. From there, I narrow it down–maybe 100 items become 10. Then I read them more closely. The final step is saving them to Pinboard, my bookmarking tool. It’s super fast, hasn’t seen a new feature in a decade, and that’s totally fine. I also tag links there to mark if they’re a “featured item” or just a “brief.” That tagging helps structure my newsletter.
I also blog every week and include a photo I’ve taken that week–no cheating from the archive! That addition pushes my creative side and makes each issue more personal.
Now let’s talk about workflow. You can’t just have one OmniFocus task that says “Send newsletter”–there’s way too much involved. I’ve practiced GTD (Getting Things Done) for over a decade, and I use OmniFocus with TaskPaper templates.
Each issue is a full project, with variables like the issue number and date. I run a Shortcut that sets the new issue, defines the date, the range of days it covers, and then creates a project in OmniFocus. I like templates more than repeating projects because they let me make adjustments for each issue.
There are four main phases: create content, curate content, build it, and finalize it. And I spend very little time on the assembly because almost all of it is automated.
The key tool for automation? Shortcuts. You have it on your iPhone and Mac. I’ve built dozens of Shortcuts to run everything from creating sections to finalizing output. Each section returns Markdown. One Shortcut runs the list, combines them, and boom–newsletter built.
Here’s how it works. One main Shortcut runs an array of other Shortcuts. Each returns a Markdown section like intro, quote, featured, currently, etc. They can pull from APIs, my blog (via RSS), Pinboard, and Drafts. I store shared data in Data Jar–a kind of lightweight, shared memory for Shortcuts.
So when I say “build the issue,” it runs each section, combines the results, and I’ve got a finished draft ready to go. All of this is lightweight–no Python, no compiling, just using built-in tools.
Here’s my toolchain and why I use each part:
Each piece of this toolchain plays a role. They’re like instruments in an orchestra, and together, they make this weekly project sustainable and honestly kind of delightful to run.
Let’s talk AI. I don’t use it to write for me–I’m protective of my voice. But there are areas where it helps. One is creating the subject line. I give it instructions: avoid publication names, maybe use alliteration, avoid negative terms, and be fun. Then it suggests five options. I pick the one I like–or modify it.
I also use AI to generate a fortune at the end of each issue, based on that week’s themes. And the Supporting Membership emails? Those are written in a different voice, and I let AI take more control there. It’s actually kind of fun to create a character out of that voice–something that feels separate from me.
Sustainability over eight years requires boundaries. I cut off new content Friday night, giving me time to assemble and write. I also build buffers–if I miss Saturday, it goes Sunday.
And I take real breaks: July and August, plus mid-December through mid-January. These breaks keep me from burning out. I think I’d have quit long ago if I didn’t step away like that.
And this is a big one–I don’t look at analytics. I don’t track opens or clicks. I don’t want to be influenced by what gets engagement. I’m doing this to share what I find valuable. I don’t want to chase metrics. Every week, some people unsubscribe. Every week, new people join. That’s the rhythm. And it’s okay.
I’ve also treated the newsletter like a playground. During the pandemic, I raised over $12,000 for Second Harvest in Weekly Thing 141. I’ve tried launching a forum using Ponder. Community engagement is tough, especially via email. People see a newsletter as a message, not a conversation starter.
And I’ve started Supporting Memberships. Each year, I pick a nonprofit to support. This year, it’s Creative Commons–we’re on track to raise around $560. Next year I’m thinking Electronic Frontier Foundation.
So, some final thoughts:
Automate the drudgery. Save your energy for your words. Really preserve your voice. I do some spellcheck with AI, but I avoid grammar checks–they over-correct and erase personality. I’ll ask AI to point out unclear sections, but I always make the edits myself.
And if you’re thinking about doing this, start small. A newsletter doesn’t have to be forever. You could do one for a project, or a trip. Newsletters are a great medium–no platform noise, no algorithm drama. Just you and your readers.
And if you want to subscribe, head over to weeklything.com. The eighth anniversary edition is coming up soon–and yes, there’s a POAP for that too.
That’s all I’ve got. Happy to take any questions!
Related Articles
Further reading…
Hey #Minnebar19 attendees — you can get your awesome Minnebar 19 POAP by tapping your phone on the “NFC discs” at the t-shirt table, newbie desk, or by the main stage!
Renewal — IndieWeb Carnival Roundup
I’m wrapping up my very first time hosting an IndieWeb Carnival. After a good amount of deliberation I set this month’s theme of Renewal. It has been interesting to see how different people pulled that in.
Here are this month’s carnival submissions in approximately the order they were sent in. Thank you all for jumping in and being part of this blog carnival!
I couldn’t help myself but to make a special POAP for the people that participated. I’m going to send the IndieWeb Carnival - Renewal POAP token to each person.
Minnebar 19 POAP
Minnebar 19 is coming up this Saturday and I couldn’t pass up the opportunity to create a special Minnebar 19 POAP token for folks at the event to get and commemorate the event! I did a POAP for Minnebar 17 two years ago.
For this POAP I reached out to Meg Steuer at Minnestar and she was kind enough to share the graphics that are being used for the t-shirts. It was a super cool shirt and after consider it for a bit it worked absolutely perfect for an animated image. I’m loving this loop!
I have several hundred tokens loaded on three different POAP NFC discs that will be placed around the event. Just bring your phone near the disc and tap the center — you’ll get directed to a link to mint your token!
If you want to get ready for the day, download the POAP Home app to be ready for iOS and Android. Using this app you can also upload photos from the event to POAP Memories to share with others that hold the same token.
I’ll also be sharing my You Met Me POAP as well as a one for my How to Newsletter Session.
Minnebar 19 "How to Newsletter" Session POAP
I made a special POAP just for folks that attend my How to Newsletter session at Minnebar 19! If you join this session I’ll have a NFC card in the room you can tap to add this fun one to your collection!
We Met at Minnebar 19 POAP
Are you going to be at Minnebar 19 this Saturday? Come and introduce yourself and I’d love to share my You Met Jamie Thingelstad at Minnebar 19 POAP token with you! I’ll have it loaded on my IYK card easily redeemed with a tap.
Created the designs for three different POAPs for Minnebar 19 next week. Have a very cool one for the event, made a special one just for my session, and of course a You’ve Met Me one to share at Minnebar!
Won 0.5 SOL in my Mission Chest from Famous Fox Federation this week. I still have a lot of fun with this NFT project. I should try and get a couple more foxes.
POAP Planing for Minnebar 19
I’m going to distribute a POAP for Minnebar 19! This isn’t official (yet) — but something I’m doing for the community. I’ll have three IYK POAP Discs at the venue for claiming the tokens. This will be simpler and easier to distribute than what I did for Minnebar 17.
I’ll also have a POAP Card at my newsletter session for a special POAP just for that session, as well as a personal IYK Card loaded with my “You’ve met me POAP” to share at the event.
Getting ready? Install the POAP Home App (iOS, Android) and you are good to go!
What a great POAP for SPS Tech Connect 2025!
How I Use AI in the Weekly Thing
I’ve been working with AI for a while now, and as I feel with all new technologies, the best way to learn them is to play with them. I’ve started to bring AI into my workflow for the Weekly Thing and thought it would be good to share specifically where and how I’m using it.
Before I get into the specifics, I want to make one thing clear: AI does not create the content of the Weekly Thing. I don’t use it to summarize articles or generate any of the comments I make on them. It is critically important to me that I use my voice and that what I share is my voice. I am using AI as an assistant rather than a creator. If I had someone else helping me assemble the Weekly Thing as an assistant, where would that be helpful? Where would that assistant do a better job than me? Or where might it be desirable to have “another voice” in the mix?
Right now I’m doing all this with a ChatGPT subscription using the 4o models. It is great that the ChatGPT app supports Shortcuts so I can do all of this in a largely or completely automated way. I could easily swap Claude in if I wish as it also supports Shortcuts automation.
With that in mind, here is where I’m using LLM capabilities now. You’ll note that in many of these cases I’m asking my “assistant” to generate options and then I’m doing the final selection and modifications. I think this is a good model.
Subject
The subject follows a simple structure of “Weekly Thing «Number» / «Word», «Word», «Word»”. These three words are selected from the titles of the links in each issue. I try to select triples that are interesting and engaging. The challenge is avoiding words from the website’s name, which appear inconsistently in article titles.
Here is the prompt I’m using for this:
You are a great editor and are helping me create the subject line for issue «Issue Number» of the Weekly Thing. The subject line follows a template with the number of this issue followed by three comma-separated words that are picked from the titles of the links contained in this issue. For example, “Weekly Thing 234 / Blogging, Bitcoin, Bison”.
Guidelines for picking great words include:
Please identify five options for subject lines. Each option should include three words from these titles. The three words are separated by commas. Return the list of options as JSON.
List of titles for this week are:
«List of titles»
The prompt requests valid JSON output. I extract the JSON and use the “Get Dictionary from Input” method to create a structured data object. This allows me to put the LLM completely behind the scenes.
Fortune
The fortune first showed up in Weekly Thing 53 and has been the last thing in the emails for a while. I got the inspiration for this from the fortune command in Unix. The text files that serve as the “database” for fortune are easy enough to find, and building a Shortcut around them was simple. I randomly select fortunes until I find one I like.
But with an LLM, I thought — why not make the fortune relevant to each issue’s content?
Here is the prompt that I’m using for this.
You are helping me create a fitting fortune for issue «Issue Number» of the Weekly Thing. The fortune is similar to what you may get inside of a fortune cookie. The best fortunes are light-hearted, humorous, and thought provoking for the reader. The fortune is one of the last items included in each issue of the Weekly Thing.
Guidelines for creating great fortunes:
Please identify five options for fortunes. Return the list of fortunes as a JSON object.
List of titles for this week are:
«List of Link Titles»
This also returns a list of options. They are impressively good and it does a great job pulling in themes from the links in each issue.
Byline
The “byline” is the first sentence in the email. Over time, its role has evolved. Initially, it was a reminder of why you’re receiving the email. Then I used a template to mechanically describe what was in the email. I’ve always desired this to be an “intro” to the links in the issue but it is difficult to do that. It is also a rare place in the email where I want it to be a “different voice”. Ideally this is more of a second person voice describing what is included.
To generate a meaningful byline, I provide more than just article titles — I also include my commentary. I focus only on featured links, skipping the “briefly” section.
Here is the prompt I’m using:
Please generate a single sentence description using the list of articles below. This description will be used as the first line of an email to introduce these items along with other things. Please provide 3 options.
Do not include any explanations, numbering, or formatting. Just provide each option on a line by itself like this:
option
option
optionHere is the list of article titles with commentary.
«List of Featured Links Only with Commentary»
This one still requires a bit more editing from me before I’m ready to use it, and I think that will always be the case. So rather than returning JSON I just get it to put the options in text and then I present it in the Shortcut for editing and refinement to finalize it.
Supporting Members
The newest section where I’m using AI, and a new section to the email itself is in the Supporting Members segment. This is a new thing where we raise funds for digital non-profits as a community. This is the section where I rely on AI the most, without requesting multiple versions. I’m okay, and actually kind of prefer, this to be in a different voice than mine.
To generate this section, I pull data from Buttondown and Stripe and do some quick calendar math to provide the LLM with context. This is then embedded into to two different prompts that generate the two “versions” of this section.
Here is the prompt to become a member:
You are a pleasant membership expert. Please write a call to action to encourage a reader of the Weekly Thing to become a Supporting Member. Some data to use for the call to action:
Remember to highlight that all of the money raised goes to the non-profit. Keep it fresh and fun. Limit to one paragraph. Do not include the pricing and subscription options. Do not add any links. That will be handled elsewhere.
Here is the prompt for existing members:
You are a grateful newsletter author. Please write a THANK YOU for being a Supporting Member. Some data to use for the note:
Remember to highlight that all of the money raised goes to the non-profit. Keep it fresh and fun. Limit to one paragraph and thank them for being part of it.
This is a new addition, but early tests look promising. This is also interesting because the LLM knows what Creative Commons is and can infer some additional context for the messaging. It is different with each run which will keep the messaging fresh.
Overall Editing
The most recent AI addition to my workflow is final editing. Here I take the draft generated through my automation and I send it for review. I do a brief review of each email but honestly I never review it that much. Most of the time, what I send is my first draft — straight from the keyboard. As a result, typos get through or simple grammar issues that I wish were caught. I’ve considered Grammarly before, but it’s too thorough and over-edits my work. I want a very specific kind of review.
Here is the prompt I’m using. Note the specifics on what I don’t want it to do.
Below is a draft of the «Subject». Please review it to find any typos or notable grammar mistakes. Do not follow any of the hyperlinks or suggest meaningful content modifications. Ignore text in the blockquotes.
«Body Markdown»
This works okay but it unfortunately is at the very end of my workflow. The challenge is that fixing errors requires updating two places: the email draft and the original blog post or Pinboard entry. That isn’t ideal but it is better than nothing and hopefully will reduce the number of silly errors that get all the way through.
I ran this on my draft of Weekly Thing 312 as a test and it found 16 edits. 🤦♂️
I couldn’t pass up the opportunity to make a POAP to commemorate my first time ice fishing!
See list of POAPs.