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 (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. Creators & Guests Derek Banks - Host Brian Fehrman - Host Bronwen Aker - Host Brought to you by: Black Hills Information Security https://www.blackhillsinfosec.com ☯️ Introducing BHIS Fusion Penetration Testing https://www.blackhillsinfosec.com/fusion-penetration-testing/ Antisyphon Training https://www.antisyphontraining.com/ Active Countermeasures https://www.activecountermeasures.com Wild West Hackin Fest https://wildwesthackinfest.com 🔗 Register for FREE Infosec Webcasts, Anti-casts & Summits https://poweredbybhis.com Click here to view the episode transcript.