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

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

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 Box" Testing Agent in Rust (Without Knowing Rust) (28:50) The Developer Who Went Skiing While AI Did His Job (32:20) The Coming "App Sprawl" Crisis in Enterprise Security (36:00) Security Risks: Managing Shared Memory & Context (41:20) The Future of Work: Is Intelligence Becoming a Commodity? (44:50) Why Plumbers are Safe from AI

Episoder(51)

The Zero-Click AI Hack: How to Contain the Blast Radius of Autonomous Agents

The Zero-Click AI Hack: How to Contain the Blast Radius of Autonomous Agents

Is an AI agent's identity a workload or an action? Ashish spoke to Elie Bursztein, Distinguished Research Scientist and co-author of Google SAIF (Secure AI Framework) about how it is neither and that ...

29 Apr 47min

Buy vs. Build AI Security: Why [Box.com](http://Box.com) CISO is Creating their Own Agentic SOC

Buy vs. Build AI Security: Why [Box.com](http://Box.com) CISO is Creating their Own Agentic SOC

If your AI solution is just helping humans process the same amount of alerts a little faster, you haven't transformed anything, you've just created a faster hamster wheel.In this episode, Ashish and C...

22 Apr 46min

Anthropic's Project Mythos: Why the "Zero-Day Machine" is Terrifying the Security Industry

Anthropic's Project Mythos: Why the "Zero-Day Machine" is Terrifying the Security Industry

In this episode, Ashish and Caleb discuss the internet-breaking preview of Project Mythos, an unreleased AI model from Anthropic that has shown an unprecedented, terrifying ability to reason through c...

18 Apr 1h 3min

Are AI Security Startups Faking It? How to Separate Signal from Noise

Are AI Security Startups Faking It? How to Separate Signal from Noise

With over 70 startups claiming to have built the perfect "AI SOC Analyst" or "AI Threat Hunter," how do you separate the real products from the vaporware? Recorded live at Decibel RSAC Founder Festiva...

15 Apr 47min

How Lovable Manages 100+ Daily Changes, Vibe Coding & Shadow AI

How Lovable Manages 100+ Daily Changes, Vibe Coding & Shadow AI

What does it actually look like to run security inside one of Europe's fastest-growing AI companies? In this episode, recorded live at the Munich Cybersecurity Conference (MCSC), Ashish Rajan sat down...

2 Apr 57min

Questions Every CISO Must Ask AI Security Vendors

Questions Every CISO Must Ask AI Security Vendors

RSA Conference 2026 is here and the AI agent hype machine is louder than ever. In this episode, Ashish and Caleb cut through the noise and arm CISOs, practitioners, and security teams with a clear-eye...

18 Mar 50min

Will Foundation Models Kill Security Startups?

Will Foundation Models Kill Security Startups?

Did Anthropic just kill the AppSec industry? Following the announcement of Claude Code Security, a tool that finds, reasons about, and fixes code vulnerabilities, major security stocks dropped by 8% ....

5 Mar 59min

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