How to Build Your Own AI Chief of Staff with Claude Code

About this episode

Caleb Sima discusses his custom-built AI Chief of Staff, Pepper, and the implications of automating work with AI agents.

What if you could automate your entire work life with a personal AI Chief of Staff? In this episode, Caleb Sima reveals "Pepper," his custom-built AI agent to Ashish that manages emails, schedules meetings, and even hires other AI experts to solve problems for him . Using Claude Code and a "vibe coding" approach, Caleb built a multi-agent system over a single holiday weekend, without writing a single line of Rust code himself . We discuss how he used this same method to build a black-box testing agent that auto-files bugs on GitHub and even designed the branding for his venture fund, White Rabbit . We explore why "intelligence is becoming a commodity," and how you can survive by becoming an architect of AI agents rather than just a worker Questions asked: (00:00) Introduction(03:20) Meet "Pepper": Caleb's AI Chief of Staff (05:40) How Pepper Dynamically Hires "Expert" Agents (07:30) Pepper Builds its Own Tools (MCP Servers) (11:50) Do You Need to Be a Coder to Do This? (12:50) Using "Claude Superpowers" to Orchestrate Agents (16:50) Automating a Venture Fund: Branding White Rabbit with AI (20:50) Building a "Black…

People in this episode

Guest: Caleb Sima

Topics covered

• AI Chief of Staff
• automation
• AI agents
• Claude Code
• enterprise security
• future of work

Keywords

• AI automation
• Pepper
• Claude Code
• AI agents
• enterprise security
• vibe coding
• black-box testing

Mentioned in this episode

Organizations: White Rabbit, GitHub

Products: Pepper, Claude Code

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