Ryan Singer
@rjs
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Fractional CPO. Author of Shape Up. Former Head of Strategy at 37signals. [email protected]
Global
Joined November 2007
"How does it break?" — This is the #1 question I'm constantly asking an SME/customer/user. In the framing stage ... when someone says the existing functionality isn't good enough. How does it break? When specifically was it not good enough and how did you know? What did you do
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Where are the fat marker sketches? Earlier upstream. When we're getting serious about building, I switch to breadboards for more concreteness. The rough mocks and breadboards will be side-by-side at kickoff.
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How to lose $50M in under an hour. This is one of the largest on-chain scam losses we’ve seen recently. A single victim lost $50M in $USDT to an address poisoning scam. The funds had arrived less than 1h earlier. The user first sent a small test tx to the correct address. Mins
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A key moment when shaping. See the red flags? That means we got down to enough detail to spot problems. These are the holes. Never trust "yes this all looks good" at a whiteboard until you've gotten past this moment. At a fuzzy, higher level — the first rough sketches —
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The core unit of experience design is the MOMENT. Every step of that meeting/setting expectations loop is a moment. We think of UX as 2D layouts. But the reason they are structured the way they are is because of how they are perceived through time as moments. Eg. what you need
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The core loop of interaction design is meeting and setting expectations. Someone hits your app. Do they recognize anything? (Meeting expectations). What happens if they click here? (Setting expectations). Did what happened match? (Meeting expectations). Now what can do they do
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New case study, end-to-end, showing a project done Shape Up style in a real-world team. Timestamps: 00:00 - Framing/Shaping terminology and assumptions 02:47 - What is Shape Up 03:38 - Basecamp vs. more typical real-world teams Case study: 04:49 - A simple kanban for
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Fantastic distinction. Specifiable vs. verifiable.
Sharing an interesting recent conversation on AI's impact on the economy. AI has been compared to various historical precedents: electricity, industrial revolution, etc., I think the strongest analogy is that of AI as a new computing paradigm (Software 2.0) because both are
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New Claude Code trick: After finding some code and making a change, ask: "What do you call that thing we just changed?" It'll just make up a reasonable name! > What do you call that thing that you just changed? ⦁ That's the slice header - It's the top section of [...] > Is that
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Good analogy.
I was able to do probably three years of API refinement for Remix 3 in three months I was writing markdown and prompting implementations into existence and then playing around with them Now as I work on a stable release, LLMs simply color in the shapes I'm drawing by hand
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When you hit an unknown, that's the moment to dig in. Don't note it for later. Don't make a task and add it to the pile. If it's a material unknown that poses a risk to the project, answer it now. I see this at the whiteboard sometimes. A dev says "I'm not sure, I'd have to look
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Love it when a hard-earned abstraction gracefully handles an unexpected use case just thrown at it.
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In-Depth: IRS Guidance for Recipients of QUALIFIED TIPS or OVERTIME PAY in 2025 (sample letters included)
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The concepts of ‘token’ and ‘embedding’ map very well to Langacker’s definition of a linguistic symbol as a phonological pole and a semantic pole. (In Cognitive Grammar)
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AI transcripts tell you more about how the human works than how the agent works.
I've shared the full transcript of every agentic coding session from implementing the unobtrusive Ghostty updates and provided commentary alongside about my thinking and process. Total cost: $15.98 over 16 sessions. "Vibing a Non-Trivial Ghostty Feature"
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Hi everyone, I work in high-end hospitality planning bespoke trips in Asia. I usually do this for VIP clients, but I've been lurking here and see a lot of first-timers stressing out about logistics. To keep my skills sharp (and verify a new workflow I'm testing), I have some
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