Security Bros

The numbers don't lie: attackers can operationalize a zero-day exploit in 12 seconds. The average enterprise took 12 weeks to patch Log4Shell. That gap is the whole problem — and it's getting worse.

Rocky sits down with Nicolas Popp, a 30-year cybersecurity veteran who built WebObjects at Apple, launched MFA-as-a-service at VeriSign, and now backs the next generation of security companies at Crosspoint Capital. Nico has seen every major wave in this industry. His read on where we are right now: the asymmetry between AI-powered attackers and human-speed defenders has crossed a line that can't be uncrossed.

In this episode, they get into the mechanics of what an agentic SOC actually looks like — not the marketing version, the operational one. What does it mean to train AI on 10 years of SOC history? How do you govern agents that are making decisions at machine speed? What happens when your load balancer has a zero-day and there's no patch? And how should MSSPs rethink their entire service model before agents eat them alive?

This one gets into the weeds in the best way. If you're building, managing, or investing in security operations, this conversation is required listening.

Chapters:

62% of cloud security incidents come from vulnerabilities your team already knew about. The problem isn't visibility. It's remediation. AI is changing that -- fast.

This week, Rocky and John sit down with Snir Ben Shimol, CEO of Zest Security, to break down why cloud vulnerability remediation is still one of the biggest unsolved problems in security and how autonomous AI agents are finally making it solvable. We cover the 30-to-90-day remediation window, why only 1-2% of vulnerabilities are actually exploitable in your environment, and how Zest's platform shrinks a backlog of 100,000 vulnerabilities by 70% in the first week -- without a single human in the loop.

If you're running a CSPM, drowning in vulnerability backlogs, or wondering what practical AI in security actually looks like (not just marketing slides), this episode is for you.

Links and Resources

A lawyer submitted six court cases to a federal judge in New York.

ChatGPT wrote every single one of them. None of them existed.

When opposing counsel said they couldn't find the cases, the lawyer went back to ChatGPT to verify whether the cases were real. ChatGPT said yes. Absolutely. You can find them on Westlaw and LexisNexis.

He submitted them anyway — under oath.

That's hallucination. That's number nine on the OWASP Top 10 for LLM Applications. And it cost him $5,000, a formal apology to every federal judge whose name appeared in the fake rulings, and probably a lot more in embarrassment.

This week on Security Bros, Rocky and John Giglio go deep on the OWASP Top 10 for LLM Applications — the 2025 edition, built by 600+ researchers across 18 countries. If you're building with AI, deploying AI, or just using it every day at work, this list is the closest thing the security world has to a peer-reviewed warning label.

They break down all 10 vulnerabilities in plain English, connect each one to real stories, and don't sugarcoat any of it:

• A world-famous white hat hacker who jailbreaks ChatGPT to write his own attack tools
• Samsung engineers who handed proprietary source code to ChatGPT — and how long it took after the ban was lifted for it to happen again (spoiler: 20 days, three incidents)
• Air Canada's chatbot that gave a grieving customer wrong information about bereavement fares — and the company's legal defense that the chatbot was "a separate legal entity"
• How DeepSeek may have reverse-engineered Claude's reasoning by querying it at scale — and what Anthropic is doing about it
• The invisible text on a webpage that hijacks your AI agent without you ever knowing

The lesson running through all of it: your security policy will never beat convenience without technical controls. You have to make the secure path the easy path.

Subscribe so you don't miss the follow-up deep dives on Claude Cowork security, AI-ready DLP, and the excessive agency problem that's about to blow up as agentic AI goes mainstream.

Resources mentioned:

• OWASP Top 10 for LLM Applications: https://owasp.org/www-project-top-10-for-large-language-model-applications/
• Previous episode: OWASP Top 10 for Web Applications

  https://youtu.be/oCuYgphY6iY

00:00 The Lawyer Who Asked AI If AI Was Lying to Him

00:33 Meet the Security Bros + What We're Covering Today

01:41 What Is OWASP? (600 Researchers, 18 Countries, One List)

04:38 #1 Prompt Injection — The Attack That's Everywhere Right Now

07:28 #2 Sensitive Information Disclosure — You Think It's Private. It's Not.

08:29 #3 Supply Chain Risk — What's Really Inside That Open Source Model?

10:27 #4 Data & Model Poisoning — The Sleeper Agent Attack

13:31 #5 Output Handling — Nobody Reviews AI Code. Nobody.

14:05 #6 Excessive Agency — When Your AI Has Too Much Power

18:12 #7 System Prompt Leakage — Stop Putting Secrets in the Instructions

20:37 #8 Vector & Embedding Weaknesses — How RAG Gets Poisoned

23:30 #9 Hallucination — AI Makes Things Up. Confidently.

25:58 #10 Unbounded Consumption — How DeepSeek May Have Stolen Claude's Brain

29:59 Real Story: Samsung's 3 Data Leaks in 20 Days

36:03 Real Story: Air Canada's "Separate Legal Entity" Defense

40:30 Real Story: The $5K Fine & Apology Letters to Federal Judges

45:09 Key Takeaways — Make the Secure Path the Easy Path

In this conversation, John and Rocky Giglio discuss the recent updates to the OWASP Top 10 list for 2025, exploring the implications of these changes for application security. They delve into the data behind the rankings, the influence of community feedback, and the importance of secure design practices. The discussion highlights the ongoing challenges in cybersecurity, particularly around misconfiguration and identity management, and emphasizes the need for a holistic approach to security that integrates both software and infrastructure considerations.

Chapters

00:00 Introduction and Technical Challenges

02:00 Exploring OWASP Top 10 Updates

07:01 Understanding OWASP and Its Data Sources

14:02 Community Influence on OWASP Rankings

17:07 Movement in OWASP Top 10: Insights and Implications

20:30 The Challenge of Keeping Up with Technology

21:37 The State of Vulnerability Management

22:44 Cloud Native vs. Traditional Organizations

24:11 Understanding the OWASP Top 10

26:14 Trends in Identification and Authentication

27:12 The Importance of Security Logging and Monitoring

28:55 Balancing Application and Infrastructure Security

30:19 The Role of Secure Design in Security

32:02 The Future of Security Practices

34:38 Understanding Weaknesses vs. Vulnerabilities

36:58 The Importance of Cloud Security Practices

39:45 Shifting Left in Security Practices

41:46 The Need for Continuous Assessment

In this episode of Security Bros, hosts Rocky and John Giglio delve into the complexities of identity management in the cybersecurity landscape, particularly in the cloud era. They discuss the challenges of identity sprawl, the importance of managing permissions, and the balance between security and business needs. The conversation emphasizes the necessity of building relationships across departments to effectively manage identity and security practices.

Chapters

00:00 Introduction to Cybersecurity and Identity Management

01:28 Challenges of Identity Management in the Cloud Era

06:13 The Importance of Permissions and Access Control

11:15 Balancing Security and Business Needs

19:01 Building Relationships for Effective Security Management

In this episode the Security Brothers, Rocky and John Giglio delve into the complexities of patch management and vulnerability management in the tech industry. They discuss the ongoing challenges faced by security practitioners, the implications of recent incidents like the CrowdStrike outage, and the evolving role of AI in enhancing security measures. The conversation emphasizes the need for comprehensive testing, strategic planning, and prioritization in managing vulnerabilities, while also exploring the importance of adapting to new technologies and methodologies in cybersecurity.

Takeaways

Handling old tech and patch management is a significant issue.
Vulnerability management is overwhelming but necessary.
Prioritization is key in dealing with numerous vulnerabilities.
Automated systems can help reduce the burden of patch management.
Testing is crucial before rolling out updates.
AI can assist in writing tests and improving deployment processes.
A comprehensive security strategy includes monitoring and logging.
Continuous learning from incidents is essential for improvement.
Collaboration with business leaders is vital for effective security management.
The landscape of vulnerabilities is constantly evolving, requiring adaptive strategies.

Chapters

00:00 Introduction to Security Challenges
02:49 The Importance of Patch Management
06:03 Navigating Vulnerabilities in Modern Tech
08:53 Lessons from the CrowdStrike Incident
11:45 Testing and Deployment Strategies
14:49 The Role of AI in Security Management
17:43 Building a Comprehensive Security Strategy
20:53 Final Thoughts and Future Directions

In this episode the brothers discuss the alarming tactics used by North Korea in cyber infiltration, particularly through fake job interviews and identity fraud. They emphasize the critical need for robust identity verification processes to combat these threats. The discussion also highlights the growing concern of insider threats within organizations and the necessity of implementing layered security strategies to protect sensitive data. The episode concludes with a reminder of the importance of mastering basic security practices to effectively mitigate risks.

Takeaways

• North Korea is using fake identities to infiltrate companies. The money collected is used for developing nuclear weapons.
• Identity verification is crucial in hiring processes.
• Insider threats are often overlooked in security measures.
• Ransomware attacks can be a consequence of data theft.
• Layered security is essential; no single solution suffices.
• Understanding user behavior is key to detecting anomalies.
• Regular assessments of security strategies are necessary.
• Basic security practices are often neglected.
• Investing in security must be balanced with operational needs.

Chapters

00:00 Introduction to Cybersecurity Challenges

02:41 North Korea's Infiltration Tactics

05:22 Identity Verification and Its Importance

08:31 Understanding Insider Threats

11:35 Ransomware and Data Protection

14:14 The Need for Multi-layered Security

17:00 Final Thoughts

John and Rocky Giglio kick of the Security Bros podcast with a special guest, Justin O'Connor founder of Onward Platforms.

Want to see it live with your own eyes? Jump into the webinar Dec 19th, 12pm EST: https://bit.ly/sb-infracode

Subscribe to catch every episode and stay up-to-date with security trends and the latest security tech.

Summary

In this inaugural episode of the Security Bros podcast, hosts Rocky and John Giglio welcome Justin O'Connor, an industry leader in cloud and AI, to discuss the current state of cloud security, the challenges posed by misconfiguration, and the impact of AI on coding practices. Justin introduces Infracodebase, a tool designed to enhance security in infrastructure as code, and demonstrates its features by building a secure API management landing zone. The conversation highlights the importance of integrating security from the outset and the need for organizations to adapt to the evolving landscape of cloud technology.

Takeaways

• Cloud adoption is primarily hybrid or multi-cloud.
• 85-90% of organizations report an increase in cloud security incidents.
• Misconfiguration is a leading cause of cloud security failures.
• AI can generate code quickly, but often lacks context.
• Security posture varies significantly between startups and enterprises.
• InfraCodebase helps enforce security standards across teams.
• The tool allows for easy integration with existing security tools.
• Automated security checks can improve compliance and reduce risks.
• Creating a secure infrastructure requires ongoing monitoring and adjustments.
• The future of cloud engineering lies in simplifying infrastructure management.

Sound bites

"AI slop is a real problem."

"This is the future of cloud engineering."

"We need to layer in security from day zero."

Chapters

00:00 Introduction to Security Bros Podcast

02:42 Current State of Cloud Security

04:39 The Impact of AI on Security

07:43 Understanding Security Posture

09:32 Infracodebase Product Overview

12:33 Creating Secure API Management

17:21 Governance and Control in Security

19:13 Terraform Configuration and Security Best Practices

24:19 Understanding Infrastructure Architecture and Security Checks

28:48 MCP Server Integration and Security Considerations

34:33 The Future of Cloud Engineering and Security

37:55 Enterprise Scale Infrastructure as Code

Check out Infracodebase at https://bit.ly/4iZM2LH

This is not sponsored, we just like Justin and his team.