It started with a simple goal: let programming students use AI assistance grounded in their textbook. What began as a basic code editor with a chat panel evolved over 15 months into StudySite.ai—a comprehensive platform with AI tutoring, learning artifacts, and virtual classroom management. This TAI Talk shares the organic journey of building with AI-assisted development, using multiple LLM vendors to grow features iteratively. Learn what worked and failed in the Spring 2025 pilot across three programming courses, and practical lessons for educators considering their own AI-powered solutions. Honest insights from someone still building and learning.