Welcome back to the Off the Wire Podcast! In this episode, we dive deep into the world of cybersecurity from an offensive standpoint. We sit down with Slade, the President of Contextual Security Solutions, to uncover what truly works in defending against real attack methods. Slade shares captivating stories and practical insights on penetration testing tools, the effectiveness of current security solutions, and the importance of visibility in cybersecurity. We discuss everything from the impact of technical configuration and tuning to the challenges of ransomware as a service. Learn how to communicate effectively with senior leadership, understand the significance of a dedicated cybersecurity budget, and get advice on the traits to look for when building a cybersecurity team. Real-world examples and fascinating anecdotes make this episode a must-watch for anyone interested in enhancing their cybersecurity posture. Don't miss out on Slade's valuable knowledge and entertaining demonstrations that aim to increase awareness and security mindfulness. Get ready to take notes and share this insightful discussion with your peers! 00:00 Introduction to Cybersecurity Podcast 00:23 Meet Slade: The Cybersecurity Expert 00:48 Slade's Attention-Grabbing Demos 05:30 Memorable Pen Testing Stories 08:51 Challenges in Cybersecurity 11:49 Small IT Departments and Security 16:12 Effective Security Measures 24:41 Business and Technical Perspectives 29:41 The Importance of Measurement and Incentives 31:05 Emerging Technologies and AI Challenges 33:24 Cybersecurity Threats and Preparedness 43:56 Soft Skills and Career Advice 46:55 Technical Skills and Budgeting in Cybersecurity 49:05 Reflections and Personal Growth 53:59 Future Topics and Final Thoughts