Off the Wire: A Play by Play on Cybersecurity and Technology Issues

Anthony Kent & Tanner Greer

A bi-weekly podcast that helps you curb cybersecurity risk and tackle technology challenges

  1. 12/15/2025

    Top 5 Reasons Why Software Projects Fail and How to Avoid Them

    Top 5 Reasons Why Software Projects Fail and How to Avoid Them | Off the Wire Podcast In this episode of Off the Wire, hosts Tanner and Anthony dive into the top reasons why software projects fail and share practical tips on how to avoid these common pitfalls. They discuss a range of crucial points, including the importance of keeping solutions simple, building strong user rapport, effective communication strategies, comprehensive training, and the value of user input. If you're in the midst of rolling out a new technology project or planning one for the future, this episode is packed with valuable insights to help ensure your project's success. Tune in as they share personal anecdotes, industry best practices, and engage in a thoughtful discussion aimed at improving your project management skills. 00:00 Welcome and Year-End Reflections 00:31 Holiday Chaos and Project Planning 01:20 The Importance of Year-End Reviews 02:10 Discussing Project Failures 02:51 Impact of Failed Projects on Teams 03:29 Balancing Risk and Simplicity in Projects 03:39 Real-Life Example of Project Impact 05:42 Top Five Reasons Projects Fail 06:26 Complicated Solutions and the KISS Method 08:24 Building Rapport and Empathy with Users 10:35 The Final 5%: Completing Projects Fully 13:57 Effective Communication Strategies 17:23 Training and Vendor Reliance 19:27 Quick Response to Issues and Drip Campaigns 21:05 Gathering Feedback and Following Up 21:46 Appreciation and Podcast Growth 23:05 Weak Testing and QA Issues 26:16 Challenges of Rapid Change 29:16 Importance of User Input 32:10 Effective Training Strategies 38:20 Final Thoughts and Community Support

    40 min
  2. 11/03/2025

    If Attackers Built Your Security Plan

    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

    1h 1m
5
out of 5
16 Ratings

About

A bi-weekly podcast that helps you curb cybersecurity risk and tackle technology challenges