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Duncan Davidson

@duncan.dev

Software developer and engineering leader. Ex-[Shopify, Microsoft for Startups, Wunderlist, JavaSoft,...]

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Latest posts by Duncan Davidson @duncan.dev

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19.10.2025 17:11 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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RubyGems repository transitions to the Ruby organization After a tumultuous month, the RubyGems repository transitions to the Ruby organization. This probably should have happened a long time ago, but at least it’s happened now.

Full post of my thoughts and permalink: duncan.dev/link/rubygem...

19.10.2025 17:09 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

What a mess. I personally believe that everyone was acting with the best of intent from their point of view under a lot of pressure. I can’t help but think how much better this would have gone if everyone had sat down first over a meal and a beverage to talk through how to accomplish this.

19.10.2025 17:09 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Finally, last month Ruby Central took some much needed steps to consolidate control and accountability over the RubyGems GitHub repositories. It was the right general thing to do but the execution of it was… not the greatest. Blame flew hard and fast.

19.10.2025 17:09 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

That didn’t help as much as it should have and things have been in an uncomfortable state since then. During my entire tenure at Shopify, I worked closely with the Ruby and Rails teams there and we were incredibly concerned about the security of the Ruby ecosystem software supply chain

19.10.2025 17:09 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

A bit of history:

For a while after its creation, RubyGems was loosely supported by the community. Then, Rails-hosting provider Engine Yard stepped in and provided support until 2015 or so. Then, AndrΓ© Arko and several others formed Ruby Together to serve as a vehicle for sponsorship of the work.

19.10.2025 17:09 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
The Transition of RubyGems Repository Ownership

I’m really happy to see the RubyGems repository transferred to the Ruby organization. This is probably 20 years overdue. www.ruby-lang.org/en/news/2025...

19.10.2025 17:09 πŸ‘ 2 πŸ” 0 πŸ’¬ 1 πŸ“Œ 1

I’m really happy that Ruby core is stepping in for the repos/governance. Gems is core to Ruby now, and has been for a long time. It should be there, imo.

18.10.2025 17:41 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

I’ve been staying out of it but I know that there are layers and layers, probably most of which aren’t visible and therefore making what we see in the surface seem really weird.

18.10.2025 17:36 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
Why do LLMs freak out over the seahorse emoji? Investigating the seahorse emoji doom loop using logitlens.

It’s a fascinating example of how LLMs generate what *ought* to exist rather than what *does* exist. Pattern matching, not truth retrieval.

Theia Vogel has a great deep-dive on why this happens: vgel.me/posts/seahor...

06.10.2025 09:43 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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There is no seahorse emoji. But GPT-5, Claude, and most other LLMs are absolutely convinced there isβ€”and will confidently try to give you one if you ask.

06.10.2025 09:43 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

I like the slight change in attitude that Sonnet 4.5 has. When it was reviewing my latest link blog post and adding in the confidence it had in its answers (in my preference prompt), it replied: β€œConfidence level: Pretty high - I write and edit regularly, though of course taste varies.” 🀣

01.10.2025 13:57 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Good timing for sure!

01.10.2025 13:56 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Really cool to see that @flox.dev keeps expanding where Nix and reproducible environments can go.

10.09.2025 17:51 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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I really like how Reeder renders the `external_url` property in JSON feed and finally got off my butt and implemented a JSON feed for my site. Yay for the open web!

08.09.2025 18:36 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

KPop Demon Hunters is on heavy rotation in the house these days, which means those damn catchy tunes are ear-wormed into my brain. Solution: Headphones and a thorough metal cleanse followed up by some good beats. Today’s treatment is the new Linkin Park followed up by some Chemical Brothers.

01.09.2025 11:05 πŸ‘ 2 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Halcyon on and on… so good

19.08.2025 10:45 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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Reminder: the β€˜Rona is still out there even in the summertime on the beach where I’ve been. This time pretty mild so far, thankfully.

19.08.2025 09:31 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Well… you know.

19.08.2025 09:29 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

I’m a fan of Satya and hold Microsoft stock.But I’m not a fan of this zero-sum approach to the near future. I may be naΓ―ve. But I still believe there’s a positive-sum version of AI disruptionβ€”one that values people and builds new leverage for teams, not just balance sheets.

27.07.2025 14:59 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

That inversion? It’s the shift from human-driven productivity to AI-driven margins. It’s a vision where profitability can growβ€”without so many of those messy human costs.

27.07.2025 14:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Satya’s memo is polished and clear. It lays out Microsoft’s pivot toward an AI-first future and positions layoffs as an inevitable consequence of reinvention at scale. β€œFor years, the sector has been generous to its employees… AI, however, inverts that relationship.” says Om.

27.07.2025 14:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

Microsoft lays off ~15,000 people in a year where it reports record profits. Satya Nadella sends a memo framing the pain as necessary and leadership as embracing it early. Om Malik took a closer look: om.co/2025…

27.07.2025 14:59 πŸ‘ 1 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0

One door closes and the next opens. God speed my friend.

13.07.2025 09:28 πŸ‘ 3 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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A free agent again, for now After over 4 years at Shopify, I’m a free agent again. The AI revolution feels like 1997’s web all over again. It’s time to step back and reflect on what I’ve learned and what’s next.

Almost four and a half years ago in early 2021, I went to work at Shopify. It was one of the best jobs I’ve had. But every tour of duty comes to a close. I’m going to take a few months this summer to really reflect on what I want to take forward with me. duncan.dev/post/free-ag...

16.06.2025 15:22 πŸ‘ 9 πŸ” 1 πŸ’¬ 1 πŸ“Œ 0

Neither do a lot of people. 🀷🏼

14.06.2025 15:59 πŸ‘ 0 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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AI thinks fast, so think slow It’s useful to treat LLM outputs as System 1 thinking (fast, reflexive, pattern-matching) while you provide System 2 oversight (deliberate, logical). This framework helps maintain thoughtful human jud...

I've found that leaning into Daniel Kahneman’s "Thinking fast and slow" has really improved the way I work with LLMs. It’s all about the mindset you arrive with.
duncan.dev/post/ai-thin...

14.06.2025 15:03 πŸ‘ 3 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0
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The art of saying no Claude can create 50 API designs in minutes. ChatGPT can write endless variations. The new superpower isn’t generating work β€” it’s knowing what to reject. Curation is becoming the primary creative act...

Claude can create 50 API designs in minutes. ChatGPT can write endless variations. The new superpower isn’t generating work β€” it’s knowing what to reject.

duncan.dev/post/art-of-...

13.06.2025 04:47 πŸ‘ 18 πŸ” 3 πŸ’¬ 1 πŸ“Œ 0

I picked up a new MacBook Pro on recent travels and the model I wanted at the Apple Store had a nano-texture screen. And oh boy, yah. Me like. It’s gooooood.

11.06.2025 13:59 πŸ‘ 6 πŸ” 0 πŸ’¬ 0 πŸ“Œ 1

Especially when enhanced by jet lag.

26.05.2025 23:50 πŸ‘ 3 πŸ” 0 πŸ’¬ 1 πŸ“Œ 0