Harry Dubke
Harry Dubke is a repeat founder and applied AI engineer. He currently serves as the CTO for Cortado AI, which he co-founded in 2024.
At Cortado, Harry builds AI agents that automate guest communications for short-term rental operators. Prior to Cortado, he scaled his own rental company to $500K ARR in fewer than 12 months and worked on multi-million dollar government grants promoting democracy in Latin America.
He is self-taught in software engineering and holds a BA from Hamilton College, where he double-majored in World Politics and Hispanic Studies, with additional study at the London School of Economics and Universidad de Buenos Aires in Argentina.
Companies
- Cortado AI: Fully autonomous guest messaging system for short-term rental operators.
- LiveCortado: My first startup, a mid-term rental company that grossed more than half a million dollars in its first 12 months of operation.
Portfolio
- Suede AI (ongoing): AI narrative monitoring for public policy organizations.
- Buy it in ChatGPT Rental App: An early MCP server + ChatGPT app that allowed users to book our clients' rentals without leaving chat.
- Terminal RPG with Claude: A text-based RPG game built with Claude's API. Showcases applied AI programming skills, including agent tooling, prompt engineering, and relational database management.