Simon Willison’s Newsletter: Deep Dives into LLMs and AI Engineering
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TL;DR
If you’re serious about understanding LLMs and AI engineering, Simon Willison’s Newsletter is one of the best resources out there. With over 38,000 subscribers, it provides detailed analysis on AI, LLMs, web engineering, open source, data science, and Python.
Who is Simon Willison?
Simon Willison is a prominent figure in the developer community. He’s the co-creator of Django (yes, the Python web framework) and the creator of Datasette, an open-source tool for exploring and publishing data. He has been deeply involved in the AI/LLM space, building practical tools and sharing his hands-on experiences.
What sets Simon apart is his ability to take complex AI topics and break them down into understandable, actionable insights. He doesn’t just talk about what’s happening in AI—he builds things with it and shares what he learns along the way.
What Makes His Newsletter Valuable
Practical, Hands-on Analysis
Unlike many AI newsletters that just aggregate news, Simon’s writing comes from actual experimentation. He builds tools, tests models, and reports on real-world behavior. When he writes about a new LLM feature or capability, you can trust it’s based on firsthand experience.
Technical Depth Without Being Overwhelming
Simon has a gift for explaining technical concepts clearly. Whether you’re a seasoned developer or someone just getting into AI, his posts meet you where you are. He provides enough context for beginners while still delivering value for experts.
Coverage Areas
According to the newsletter description, it covers:
- AI and LLMs - The core focus, with deep dives into model capabilities, prompting techniques, and practical applications
- Web Engineering - How AI intersects with web development
- Open Source - Updates on open-source AI tools and his own projects
- Data Science - Practical data exploration and analysis
- Datasette and SQLite - His specialty tools for data exploration
- Python - The language that ties much of this together
Independent Voice
Simon writes independently. He’s not promoting a specific product or company. This gives him the freedom to provide honest assessments of different tools, models, and approaches.
Must-Read: 2025 Year in LLMs
One of Simon’s best pieces is his annual review 2025: The year in LLMs. This comprehensive post covers everything that happened in the LLM space throughout 2025, including:
- The year of “reasoning” - How inference-scaling and RLVR became mainstream
- The year of coding agents - Claude Code, Codex CLI, and the rise of autonomous coding
- The year of prompt-driven image editing - GPT-4o image generation and Nano Banana
- The year of vibe coding - Andrej Karpathy’s influential term and what it really means
- The year of Chinese open weight models - DeepSeek, Qwen, Kimi, and more
- The year of $200/month subscriptions - The new pricing tier for power users
- The year of MCP - Model Context Protocol’s explosive growth
This post is a masterclass in synthesizing a year’s worth of AI developments into actionable insights. It’s the kind of analysis that would take weeks to compile on your own.
Why I Recommend It
For anyone working with LLMs or trying to keep up with the rapidly evolving AI landscape, having a trusted source for detailed analysis is invaluable. Simon fills this gap perfectly.
His posts often save me hours of research. When a new model drops or a new technique emerges, I wait to see what Simon has to say about it. His analysis is thorough, practical, and actionable.
Subscribe
You can subscribe to Simon Willison’s Newsletter here:
With over 38,000 subscribers already, you’ll be joining a community of developers and AI practitioners who value thoughtful, in-depth analysis over hype.
If you know of other high-quality AI/LLM resources, feel free to share them with me. Building a good reading list is one of the best investments you can make in this rapidly changing field.