Architecture Weekly Turns 5: Lessons from Building a Tech Newsletter
Published on 29.12.2025
Architecture Weekly is 5 Years Old
TLDR: Oskar Dudycz celebrates five years of Architecture Weekly, a newsletter that evolved from a personal GitHub repository of curated links into a paid Substack with monthly webinars. The journey reveals hard truths about newsletter economics and the challenges of sustaining quality content creation.
Summary:
Architecture Weekly began as most useful tools do—solving its creator's own problem. Dudycz, self-described as someone who perpetually crashes Firefox with hundreds of open tabs, needed a way to organize his reading. The solution was elegantly simple: a public GitHub repository with Markdown files containing curated links organized by topic. That repository still exists at github.com/oskardudycz/ArchitectureWeekly, serving as a historical artifact of a newsletter's DNA.
The transition from personal knowledge management to public newsletter followed a predictable pattern. Friends found the links useful. Friends of friends wanted access. Eventually, the demand for "a proper newsletter" overcame Dudycz's reluctance, and he moved to Substack specifically to avoid building his own blogging engine—a pragmatic choice that reveals architectural wisdom about focusing on core value rather than infrastructure.
The experiment with paid content is where the narrative becomes instructive for anyone considering content creation. Dudycz launched monthly webinars with guests, built a Discord community, achieved Substack Bestseller status, and still concluded that the economics don't work. Twenty-eight webinars representing roughly 50 hours of free content now sits publicly available. The implicit lesson is stark: even successful newsletters may not justify their time investment when measured purely in financial terms.
What's particularly honest about this reflection is the acknowledgment that curation isn't easy. The perfectionist burden of ensuring every recommended article "triggers the movement of brain cells" creates unsustainable pressure over time. For architects and team leads considering similar endeavors, this is a crucial consideration—the gap between occasional content creation and sustained weekly publication is substantial.
The future direction hints at a rebrand toward event-driven.news, aligning more closely with Dudycz's consulting work and OSS projects like Emmett. This pivot illustrates a sensible architectural decision: aligning content creation with primary business activities rather than treating it as a separate revenue stream.
Key takeaways:
- Personal knowledge management tools can evolve into valuable community resources
- Newsletter economics rarely justify the time investment even for "successful" creators
- Curation quality requires significant ongoing effort that compounds over time
- Aligning content with core business activities is more sustainable than treating it as a separate product