Newsletter Archive

DeveloPassion's Newsletter #212 - Obsidian Starter Kit v4 Is Live

Four weeks of intense shipping; OSK v4 went live on May 15th as a fully AI-native release. Eight new AI agents, a complete tutorial library, the Book Exporter plugin, five articles published, a new YouTube video on AI context management, the Obsidian Community site launch, sales records,…

Sebastien Dubois

18 May 2026 — 12 min read

Edition 212 of my newsletter, discussing Knowledge Work, AI, Knowledge Management, Zen Productivity, Personal Organization, and more!

Hello everyone! I'm Sébastien Dubois, your host. You're receiving this email because you signed up for DeveloPassion's Newsletter, or bought one of my products. Thank you for being here with me ✨

If you enjoy this, please forward it to your friends ❤️. If this email was forwarded to you, then don't forget to subscribe and become a supporter

Welcome

Welcome to all the new readers ❤️

The past four weeks have been quite intense shipping window I've had in years. The headline: Obsidian Starter Kit v4 went live on May 15th; an AI-native release that redefines what you can do with an Obsidian vault. But it's far from the only thing I shipped. New articles, new videos, a brand new Obsidian plugin (Book Exporter), new AI Agents, and more! I've also updated many of my plugins recently, adding features and fixing bugs.

On the personal side, things are going well. I'm still running consistently (ran my first 13KM Urban Challenge on Sunday with my son; mostly fun, except for the 300-meter stretch through an open sewer 🤢). My recovery from the implant surgery in late April went smoothly, and I'm back to gym workouts.

Life is good, I'm having fun, enjoying time with family. Also, the wedding planning is going smoothly. Stress is rising though as we're approaching the magic day! ;-)

I'm also glad to have resumed playing Arkham Horror LCG (my favorite board game)

On the reading side: I finished J'ai encore menti ! (book) by Gilles Legardinier (fun read, French), The Lost Years (book) by Mary Higgins Clark and I'm still working through The Feynman Lectures on Physics (book) during commutes (among other books!). The combination of audio book + voice notes + AI for first-principles questions is wildly effective...

Alright, let's gooooo 🚀

Highlights

🚀 Obsidian Starter Kit v4 is LIVE — the AI-native release shipped on May 15th
🤖 8 new AI agents (Sports Coach, Health Coach, Business Manager, Wiki review panels, and more)
📚 Complete tutorial library for OSK; from Dot capture to full agent authoring
🔌 New plugin: Book Exporter — turn vault notes into EPUB/PDF via Pandoc
📝 Multiple articles published: OSK v4 launch, Heavy AI Agents anti-pattern, AI Privacy guide, Book Exporter announcement, Claude Code on GitHub Copilot, ...
🎬 New YouTube video: Levels of AI Context Management (7 levels, from zero context to advanced architectures)
🌐 Obsidian Community site launched — all my plugins are listed there with safety scorecards
🔒 Obsidian Sync passed Cure53 and Trail of Bits security audits
💰 Two new sales records (~€4K monthly, new Gumroad record)

Before You Go Any Further

I want to reach more people. Got 20 seconds? Share the link with one friend/colleague who would benefit from joining us. And don't forget to also mention the Knowii Community ❤️

And if you bought some of my products or courses? Please leave a rating/review. It really helps ❤️

The Lab 🧪

🚀 Obsidian Starter Kit v4 Is Live; The AI-Native Release

After months of work, OSK v4 shipped on May 15th. This is a BIG release. It completely changes the way you can use and leverage Obsidian.

For years, OSK has been "a super well-organized vault with templates and plugins." v4 is something different. It's a vault designed to collaborate with AI, while keeping you in full control of your thinking. The line between "you" and "your AI assistant" gets sharper, not blurrier. The vault enforces the boundary so you don't have to think about it.

What's actually in it:

An AI Assistant System with eight new specialized agents (Sports Coach, Health Coach, Business Manager, Wiki review panels, and more) using a lean agents + deep skills architecture; not heavy specialists
A clear Foundation document (AI Augmentation Philosophy) that captures the why: augment thinking, don't replace it
The new OSK Plugin with built-in CLI (osk-cli), validation, note type registry, and configuration UI
A complete tutorial library covering every workflow: capturing dots, building your voice profile, running weekly/monthly/quarterly reviews, tracking health, working with Bases, creating your own agent, authoring your own skill, and more
New plugins: Life Tracker for health visualization, the Readwise MCP Server, reMarkable notebook sync, qmd for semantic search, the CLI REST MCP for safe vault exposure to external agents, and more!
And a ton more!

If you're an existing OSK user, you should upgrade. If you're new to OSK, this is the best version yet to start with.

I also wrote a launch article with all the new features:

💬 Early Reactions to v4

A few words from the community since launch:

"Your migration guide is phenomenal." ; Chris Flanagan

"Awesome 🎉 Very happy about these news. Will definitely have a look and possibly start migrating over the weekend." ; Sofia Alfredsson

If you're trying v4, I'd love to hear what's clicking (and what isn't). Reply to this email or post in Knowii Community.

🧠 Don't Keep AI Out of Your Vault

I keep stumbling on the advice "don't let AI touch your knowledge base". The fear is real (AI slop, AI replacing thinking, lock-in), but the conclusion is the wrong fix for the right problem. AI doesn't belong outside your vault; it belongs INSIDE, doing the plumbing while YOU stay in charge of the thinking.

In this piece, I lay out the mindset shift, why a rich vault makes AI dramatically more useful, and how OSK v4 (specifically LLM Wikis) bakes provenance, confidence, and a graduation path into the structure so AI-generated content can live alongside your permanent notes without polluting them.

🧠 Heavy AI Agents Are an Anti-Pattern

Halfway through the OSK v4 work, I hit a wall: my agent roster had grown too big, too specialized, and too cumbersome to maintain. Every new task seemed to demand a new dedicated agent. The cognitive load (for me!) was getting out of hand. So I stopped, rethought the architecture, and wrote it up.

I approached things differently: fewer agents with a much deeper skill library. Lean coordinators (agents) compose AI skills on demand. One agent doesn't need to know how to do everything; it needs to know how to find the right AI skills and orchestrate those.

🔒 Where Your AI Prompts Really Go; A Practical Guide to AI Privacy

A question from a Knowii Community member pushed me to do some research about AI Privacy.

If you give AI tools your most personal thoughts, you should know what actually happens to that data. And it's almost always more complicated than the marketing copy suggests.

I spent a couple of hours mapping the privacy landscape across all the major AI providers (OpenAI, Anthropic, Google, xAI, Mistral, Cohere, Perplexity, Cursor, Ollama, OpenRouter, Hugging Face, the dedicated inference providers, European providers, and the GPU clouds). The result is a practical guide for anyone making AI tooling decisions; especially if you're a creator, knowledge worker, or solopreneur.

It covers:

Data training practices per provider
Privacy tiers explained (consumer vs API vs enterprise vs self-hosted)
A clear evaluation framework for picking a provider
Provider categories with concrete examples
A summary table of who trains on what

🔌 A New Obsidian Plugin: Book Exporter

Book Exporter takes a manifest note (a single markdown file that lists which notes to include, in what order, with what metadata) and produces a proper EPUB and/or PDF via Pandoc. Use it to ship your book, your course manual, your wiki dump, or whatever long-form content lives in your vault.

🛠️ Run Claude Code on Your GitHub Copilot Subscription

Quick tactical one for the developers reading this: if you have a GitHub Copilot subscription, you can route Claude Code through it via a local LiteLLM proxy. No additional Anthropic API key needed.

I experimented with this at work, and while there are limitations, it's still good to know it's possible to do!

🎬 New YouTube Video; Levels of AI Context Management

One of the things I keep coming back to with creators and knowledge workers: how you feed context to AI is the single biggest determinant of output quality. So I broke it down into seven levels, from "no context, just a prompt" to "fully architected context with identity, voice profile, business context, project context, and session context."

📰 Cool Finds

A short list of things I found interesting these past weeks.

🌐 The Obsidian Community site launched at https://community.obsidian.md — official platform for discovering and evaluating plugins and themes, with automated safety scorecards. I got all my plugins listed there (https://community.obsidian.md/users/dsebastien). The new feedback loop is way better
- My notes about this: 2026-05-13 The Future of Obsidian Plugins
Structuring AI responses as HTML — HTML as another canvas for AI output, alongside markdown; unlocks animation, interactivity, and visual structure
- News article I shared: 2026-05-12 HTML as the New AI Output Format — news note on HTML as a richer way to explore AI-generated ideas
🧠 Karpathy's Software 3.0 framing: classical code (1.0), neural networks (2.0), LLMs as runtime (3.0). The whole 1.0/2.0/3.0 stack is a useful design grammar for the agent-native economy. If you build anything with AI, read his recent talks
🧠 Obsidian Web Clipper — major updates: highlights are now first-class objects, Reader mode persists across link navigation (continuous distraction-free reading), customizable colors/fonts, frictionless copy-to-Markdown; the clipper has quietly become one of the most pleasant ways to read the web, not just save from it
🔒 Obsidian Sync passed Cure53 and Trail of Bits audits: two independent security audits, fully public. End-to-end encryption holds. This is exactly the rigor the PKM space needs
- News article about this: 2026-05-14 Obsidian Sync Passes Cure53 and Trail of Bits Audits
🧠 Tolaria; Luca Rossi's free, open-source desktop app for managing markdown knowledge bases; AGPL, Git-backed, native MCP server for Claude Code, "second brain for the AI era" — a credible AI-native alternative to Obsidian/Logseq
🇨🇳 Kimi K2.6: Moonshot's new open-weight agentic model; 66.7% on Terminal-Bench 2.0, 4,000+ tool calls in 12h sessions, 300-agent swarms. The open-weight frontier keeps catching up
🇨🇳 Qwen3.6-27B: dense, natively multimodal 27B model that beats the 397B-total Qwen3.5 on agentic coding. Q4_K_M is 16.8 GB; runs flagship-quality agentic coding on a single 24 GB consumer GPU. Drop-in for Claude Code
⚡ Gemma 4 gets Multi-Token Prediction Drafters: co-designed small drafters that share the target's KV cache for 3x speedup on inference. Likely to become standard for open-weight releases
🧪 Hermes Agent self-evolution (Nous Research): a DSPy + GEPA optimization companion that reads execution traces, mutates skills/prompts/code, and gates via tests. The production reference for an operationalized agent improvement loop with no GPU training
Mistral Remote Agents — async cloud-based coding agents inside Vibe; powered by Medium 3.5; integrates with GitHub/Linear/Jira/Slack
🎨 Nano Banana Pro (Google DeepMind) + ChatGPT Images 2.0 (OpenAI): two very different frontier image models; multi-language text rendering, world-knowledge infographics, identity continuity across multi-character scenes
🎨 DESIGN.md Specification — Google Labs' Apache-2.0 spec pairing YAML design tokens with markdown design rationale, so coding agents apply visual identity correctly instead of falling back to generic UI
Trellis 2 — Microsoft's 3D generative AI framework for creating high-quality 3D models from text and images
- News article I published: 2026-05-12 Trellis 2 - Fast 3D Model Generation Now Easy to Import — news on how Trellis 2 models integrate seamlessly with Blender
Vercel DeepSec — open-source agent-powered vulnerability scanner from Vercel Labs using Claude Opus 4.7
Windows Sandbox — disposable Hyper-V-isolated Windows desktop built into Pro/Enterprise/Education; container-VM hybrid via Dynamic Base Image, configurable via .wsb files, scriptable via the new wsb CLI in 24H2

💡 Business Updates

A few things on the DeveloPassion side:

Two sales records broken: April hit €4K (a recurring monthly record), then April-end set a new Gumroad single-month record. Cumulative paid customer count keeps climbing
Knowii Community pricing updated: no more monthly billing. Three tiers, all quarterly minimum: Explorer (€14.99/quarter), Knowledge Builder (€59.99/quarter), Knowledge Master (€119.99/quarter). The 3-month minimum is intentional; it filters for committed members who will participate and apply
OSK price update planned: I'm raising the OSK price very soon now that v4 is live. Existing customers get the v4 upgrade for free. If you've been on the fence, now's the time

🧠 Tip of the Week

A quote I extracted from Andrej Karpathy this month that I keep coming back to:

You can outsource your thinking, but you can't outsource your understanding

This is the distinction for anyone working with AI. Thinking is the act of generating, evaluating, synthesizing. AI can absolutely do a lot of that for you. Understanding is the internal model you carry about why something is true, what's connected to what, and what changes when conditions change. That cannot be outsourced.

The implication for your knowledge system: your permanent notes are where your understanding lives. AI can help you draft, summarize, search, connect. But the moment a thought becomes "yours," you have to write it. In your words. With your structure. With your skin in the game.

This is exactly why OSK v4 cares about the line between AI output and your own notes (where your own understanding lives). The vault is a thinking instrument, not a dumb content factory.

Until Next Time

This was a heavy four weeks. The next four weeks will be lighter on shipping and heavier on consolidation: more video content, more tutorials, more onboarding flows for OSK v4, and (finally) more focused work on The Context Layer book.

If you're using OSK v4 already; thank you. If you're upgrading from v3; the migration guide is in the kit, and the Knowii Community Knowledge Builder tier gets you direct support.

That's it for today! ✨

Ready to dive in?

🚀 Get OSK v4 (Essentials €129.99, Premium €198.99): https://www.store.dsebastien.net/product/obsidian-starter-kit/
🧠 Join Knowii (Builder tier €59.99/quarter): https://www.store.dsebastien.net/product/knowii-community/
📰 More content at https://dsebastien.net

Talk to you again soon ❤️

— Sébastien

About Sébastien

I'm Sébastien Dubois, and I'm on a mission to help knowledge workers escape information overload. After 20+ years in IT and seeing too many brilliant minds drowning in digital chaos, I've decided to help people build systems that actually work. Through the Knowii Community, my courses, products & services and my Website/Newsletter, I share practical and battle-tested systems.

I write about Knowledge Work, Personal Knowledge Management, Note-taking, Lifelong Learning, Personal Organization, Productivity, and more. I also craft lovely digital products and tools.

If you want to follow my work, then become a member and join our community.

Ready to get to the next level?

Since you're interested in Obsidian:

🚀 Obsidian Starter Kit — Skip weeks of setup with 40+ templates
🎬 Obsidian Starter Course — Master Obsidian in 2+ hours
📚 KM for Beginners — 10+ hours of structured video lessons
🎯 Join Knowii — Community + ALL courses & tools