In this special edition recorded live at RSA Conference, Joseph Carson is joined by Gerasimos Marketos (gmar), Chief Product Officer at Hack The Box.

They explore how AI is reshaping cybersecurity skills, why traditional education is struggling to keep up, and how hands-on platforms are redefining how defenders and ethical hackers are trained. From real-world fraud detection to AI-powered CTF competitions, this episode dives into the evolving relationship between humans and machines in cybersecurity.

🔑 Key Themes & Topics

• AI vs Humans in cybersecurity competitions
• Why AI is an accelerator, not a replacement
• The evolution from traditional training → hands-on gamified learning
• Closing the cybersecurity skills gap
• Red, Blue, and Purple team upskilling
• AI governance, risk, and agentic threats
• The future of cybersecurity careers and hiring

⏱️ Chapters

• 00:00 – Introduction & RSA Conference insights
• 02:00 – GMar’s journey: Data → Fraud → Cybersecurity
• 06:30 – Who and What is Hack The Box?
• 10:30 – AI vs Humans: CTF research findings
• 13:00 – AI as a productivity multiplier
• 15:30 – Real-world example: AI winning competitions
• 16:00 – RSAC trends: AI everywhere
• 17:00 – AI governance & emerging risks
• 18:00 – AI for security vs security for AI
• 19:00 – Staying relevant in cybersecurity

🚀 Hack The Box Explained

Hack The Box is a cybersecurity upskilling platform offering:

• 🎓 Academy – Structured learning paths
• 🧩 Challenges & Labs – Hands-on environments
• 🏁 CTFs (Capture The Flag) – Competitive exercises
• 🏢 Pro Labs – Enterprise-scale simulations
• 🔎 Talent Search – Connecting skilled professionals with employers

It supports:

• Red Teams (Offense)
• Blue Teams (Defense)
• Purple Teams (Collaboration)

Resources:

https://www.hackthebox.com/

https://www.linkedin.com/in/gmarketos/

https://www.hackthebox.com/ai-augmented-cyber-workforce-report

In this episode, Fernando Montenegro shares his journey into the cybersecurity industry, insights on industry analysis, and the evolving trends shaping cybersecurity today. Discover how analysts bridge the gap between vendors, buyers, investors, and academia, and learn practical tips for engaging effectively with industry experts.

key Takeaways

• Role of industry analysts in cybersecurity
• Emerging trends in cybersecurity including AI and attack surface expansion
• Effective engagement with analysts for decision support
• Strategic cybersecurity budgeting and investment
• Influence of economics and incentives on security decisions

sound bites

"Understanding what's going on in the world"

"Good enough security can be effective"

"Workload AI versus workforce AI"

Chapters

00:00 Introduction to Security by Default Podcast

00:53 Fernando Montenegro's Origin Story

05:16 The Role of an Industry Analyst

08:55 Maximizing Value from Analyst Interactions

13:16 Understanding AI in Conversations

15:44 Choosing the Right Solutions

16:40 Decision-Making in Technology and Business

17:13 Trends in Cybersecurity and AI

18:26 Understanding Workload vs. Workforce AI

19:40 The Evolving Role of Security Professionals

21:43 The Strategic Importance of Cybersecurity

23:58 Incentives and Decision-Making in Security

25:53 The Shift Left Approach in Development

27:16 Budgeting for Cybersecurity Investments

30:47 Navigating Cybersecurity Budgets

32:26 Engaging with Analysts and Staying Informed

34:33 Curating Information in a Data-Driven World

36:55 Balancing Operational and Strategic Insights

37:51 Connecting with Analysts and Final Thoughts

Resources

LinkedIn Profile of Fernando Montenegro - https://www.linkedin.com/in/fsmontenegro/

Futurum Group - https://futurumgroup.com/

Obsidian Knowledge Management System - https://obsidian.md/

Book: Why Most Security Budgets Go to Waste by Ross Young - https://a.co/d/02BZPwdO

Join cybersecurity expert Joseph Carson and guest Gary as they explore innovative ways to make cybersecurity engaging, fun, and accessible. Discover how humor, storytelling, and community involvement can transform the industry and attract new talent.

Chapters

00:00 Welcome to the Cybersecurity Chaos

02:32 From Fear to Fun in Cybersecurity

05:27 The Journey of a Cyber Advocate

08:09 The Importance of Community and Collaboration

10:45 Bringing Laughter Back to Cybersecurity

13:13 Rebranding Cybersecurity for New Talent

16:00 The Power of Words in Cybersecurity

18:43 Innovative Approaches to Cyber Awareness

21:29 Lessons from Kids: Simplifying Cybersecurity

24:39 The Inner Child and Cognitive Dissonance

26:40 Gamification and Learning Innovations

28:19 Storytelling in Cybersecurity

29:15 Cybersecurity Starts at Home

30:36 Community Engagement and Employee Connection

32:14 The Importance of Acknowledgment

34:13 Finding Joy in Everyday Life

35:11 Humor as a Coping Mechanism

40:04 The Power of Positive Thinking

45:02 Mission Accomplished: Fun and Safety

Resources

Cyber Heroes Comics - https://cyberheroescomics.com/

Gary's LinkedIn Profile - https://www.linkedin.com/in/gary-berman/