Caleb Sima
Co-host of AI Security Podcast and former CISO with experience in security product evaluation, AI automation strategy for security teams, and industry predictions.
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Feb 11, 2026 • 47min
How to Build Your Own AI Chief of Staff with Claude Code
Caleb Sima, a venture investor and AI builder who created Pepper, a multi-agent AI chief of staff. He explains building Pepper with Claude Code, how it spins up specialist agents and even builds its own tools. They cover rapid prototyping, auto-generating branding and websites, black-box testing that files GitHub bugs, and security risks from app sprawl and shared memory.
