I Gave My AI Agent $1,000 - Whats the worst that could happen?

Milo started its life in 2021 as a simple chatbot that allowed me to access my Obsidian Notebook via the Telegram Messaging Platform. At the time it was simple and worked well, but over the past several years, Milo has evolved to the point where it not only superseded Obsidian but has essentially become its own standalone agentic operating system. I built a powerful automation framework into Milo and an extension system to allow me to extend the functionality of Milo. So I decided to do the sane thing - create a stock market trading system powered by Milo and give it $1,000 of my own cash; what's the worst that could happen?