Hey Skippy! | Episode 60
This episode takes a break from the usual AI security news roundup for a show-and-tell discussion centered on "Skippy," an AI-powered personal assistant built to automate cybersecurity workflows. The conversation covers how the project evolved from an OpenClaw experiment into a system that tracks AI and cybersecurity news, generates daily intelligence briefs, documents its own code, recommends training updates, assists with content creation, and performs automated vulnerability research. The hosts also discuss practical AI workflows, prompt engineering, model selection, and lessons learned from integrating LLMs into day-to-day security operations.
Key Concepts and Topics
* The origin and evolution of the "Skippy" AI assistant
* Building an AI agent with OpenClaw and Telegram
* Automating AI and cybersecurity news aggregation
* Daily intelligence briefs and trend analysis
* Self-documenting AI-assisted software development
* Personalizing AI behavior with custom instructions
* AI-assisted content creation and documentation
* Identifying training and course update opportunities
* Automated vulnerability research against open-source projects
* Comparing open and commercial LLMs for security workflows
Click here to watch this episode on YouTube.
Brought to you by:
Key Concepts and Topics
* The origin and evolution of the "Skippy" AI assistant
* Building an AI agent with OpenClaw and Telegram
* Automating AI and cybersecurity news aggregation
* Daily intelligence briefs and trend analysis
* Self-documenting AI-assisted software development
* Personalizing AI behavior with custom instructions
* AI-assisted content creation and documentation
* Identifying training and course update opportunities
* Automated vulnerability research against open-source projects
* Comparing open and commercial LLMs for security workflows
- (00:00) - Intro - Show and Tell
- (00:55) - Introducing My Bot Skippy!
- (03:56) - Why the name Skippy?
- (06:55) - The Skippy Dashboard
- (09:00) - Questions about Skippy?
- (09:57) - Other Features, customization and automation
- (16:28) - AI creates more work for you to do
- (20:33) - What can we do next?
Click here to watch this episode on YouTube.
Brought to you by:
Black Hills Information Security
☯️ Introducing BHIS Fusion Penetration Testing
https://www.blackhillsinfosec.com/fusion-penetration-testing/
Antisyphon Training
Active Countermeasures
Wild West Hackin Fest
Creators and Guests
Host
Brian Fehrman
Brian Fehrman is a long-time BHIS Security Researcher and Consultant with extensive academic credentials and industry certifications who specializes in AI, hardware hacking, and red teaming, and outside of work is an avid Brazilian Jiu-Jitsu practitioner, big-game hunter, and home-improvement enthusiast.
Host
Bronwen Aker
Bronwen Aker is a BHIS Technical Editor who joined full-time in 2022 after years of contract work, bringing decades of web development and technical training experience to her roles in editing pentest reports, enhancing QA/QC processes, and improving public websites, and who enjoys sci-fi/fantasy, Animal Crossing, and dogs outside of work.
Host
Derek Banks
Derek is a BHIS Security Consultant, Penetration Tester, and Red Teamer with advanced degrees, industry certifications, and broad experience across forensics, incident response, monitoring, and offensive security, who enjoys learning from colleagues, helping clients improve their security, and spending his free time with family, fitness, and playing bass guitar.