Deep Dive: Ivan Milev of Codeboarding - Coding Agents Have a Black Box Problem

Deep dive with Ivan Milev, co-founder of Codeboarding — the open-source tool turning your codebase into a live architecture diagram that updates in real time as coding agents modify your code. Coding agents have a black box problem. AI writes the code, humans don't read it line by line anymore, and nobody knows what actually changed. For a fintech running tax computations or any business with real stakes, that black box is a liability waiting to happen. Ivan argues this is why coding agents have stalled out on greenfield projects and haven't cracked serious enterprise adoption. Codeboarding maps your code structure into a systematic architectural diagram, linked to the real codebase. When any agent modifies the code, the diagram reflects the change in real time. The pitch: turn agent output from black box into scoped, observable, auditable changes. Ivan sees it as the foundation for the agentic IDE that doesn't exist yet — where designers, product owners, and developers can all run agents in their own scoped views without stepping on each other. Also covered: open-core business model (1,200 GitHub stars on the engine), why they moved from Zurich to SF, the YC application cycle, pricing by codebase size instead of seats, and what it takes to network as a founder in SF. Codeboarding is hiring a design partner. Ivan is in SF pitching and plans to run a hackathon this month. — Agentic Stories is the weekday briefing on the AI agent economy — governance, security, and deployment. Deep Dives drop on off-days with founders building in the space. New episodes Monday, Wednesday, Friday. agenticstories.ai