The Weekly Vibe - Jan 2, 2026 - From COBOL punch cards โ IIS + SQL Server โ Vibe Coding (and why Skills are the โdotfile protocolโ)
Just had a great conversation that covered the entire arc of software development โ from legacy systems to modern AI-assisted shipping. Brad walked through how he shipped his first live web app running on Windows Server / IIS with a Microsoft SQL Server backend โ largely guided by AI prompts, with real-world corrections applied using deep Windows experience. We then zoomed out into why vibe coding feels like a full-circle moment: after years in executive and business roles, AI agents make it possible to return to building without being blocked by todayโs frameworks. What we covered - Shipping a live IIS + SQL Server app with AI-assisted deployment - Career arc: COBOL, punch cards, IBM System/360 โ modern web apps - Why shipping something live (even basic) matters - Working through Corbin Brownโs Thumbio course - Using vibe coding to rapidly recreate complex apps Token limits & tooling reality We talked candidly about token limits and how heavy builders hit them fast. Several strategies came up: - OpenRouter for buying credits and routing across models - Using different models for different tasks (Gemini for frontend, Claude for coding) - Why open-source IDE agents move faster than locked tools Skills, MCP, and the future of agent workflows A big chunk of the conversation focused on Skills and why they matter. - Skills load metadata first, full instructions only when triggered - This enables progressive disclosure and smaller context windows - Skills act like a standardized โdotfile protocolโ for AI tools - MCP handles tools; Skills handle instructions Product ideas sparked - Browser plugins that allow AI-driven changes within constraints (e.g. bulk calendar color rules) - Proposal & marketing document tools where users say: โMove the logo, add padding, center itโ โ no massive UI needed - Using Skills as customizable, client-specific branding & layout engines A powerful habit: prompts as source code One standout practice: - changes.md โ what the AI changed in each session - prompts.md โ every prompt used to get there