Exploring Information Security - Exploring Information Security

In this episode of Exploring Information Security, Tim chats with Chris Traynor of Black Hills Information Security (BHIS) and Ridgeback InfoSec. Chris is a seasoned penetration tester and educator who’s been developing hands-on training that’s grounded in real-world experience. He shares the origins of his “Offensive Tooling” classes, what makes a great pentest report, and how he balances teaching with travel, work, and family life.

Chris breaks down the tooling that matters, how he approaches infrastructure setup for operators, and why he emphasizes actionable reporting. He also talks about the importance of open-source tooling, customizing workflows, and automating the tedious parts of testing. Whether you're just getting into offensive security or are a veteran red teamer, this episode offers insights and practical takeaways.

• The importance of hands-on offensive tooling training

• How to write reports that are actually useful to dev and ops teams

• Why pentesters need infrastructure knowledge

• Open-source tools, custom scripts, and automation

• The challenges and wins of presenting at BSides and beyond

• Avoiding burnout while building community and sharing knowledge

Social

• Twitter

• LinkedIn

Upcoming Events

• March 28 security live on https://www.twitch.tv/womaninredpresents

• KernelCon April 1-2 teaching my Offensive Tooling for Operators 2-day class

• The Illustrated Pentester - Short Stories of Security Vol. 4 April 10

 - Past ones...

•    The Illustrated Pentester - Short Stories of Security

  • The Illustrated Pentester - Short Stories of Security Vol. 2

  • The Illustrated Pentester - Short Stories of Security Vol. 3

•  BSidesHBG April 25

•  BSidesKC April 26

•  Possibly BSides Flood City (May 8) and BSides Ft Wayne (June 7) too

ETHOS LABS Website

Connect with Tim Folwer on Linkedin

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In this episode of Exploring Information Security, host Tim De Block sits down with James Gillkey to discuss hands-on hacking training at ShowMeCon. James is revamping a long-standing pentesting training course to bring modern techniques, updated tools, and a focus on efficiency to security professionals. He shares insights into building effective training labs, leveraging Python virtual environments, and incorporating real-world offensive security methodologies into a structured learning experience.

• The evolution of hands-on hacking training and its history

• Setting up virtualized pentesting environments with Python and GitHub tools

• Common mistakes in pentesting and how to avoid them

• The balance between red team engagements and SOC awareness

• The importance of password cracking, enumeration, and network recon

• How cloud security assessments differ from traditional network pentesting

• The role of AI in pentesting and whether it’s a useful tool or a shortcut

• ShowMeCon’s Fallout-themed hacking lab and what to expect in the training

• Hands-on experience is crucial. The best way to learn pentesting is by doing it.

• Virtualized environments simplify tool management and prevent conflicts.

• AI is an emerging tool in pentesting, but it doesn’t replace fundamental knowledge.

• Cloud security requires a different mindset due to its unique challenges and toolsets.

• Communication with SOC teams is essential to avoid unnecessary panic during testing.

• Efficiency matters. The goal of the training is to give students actionable skills they can use immediately.

• James Gillkey on Twitter/X – @RetroCodex

Use the promo code “ExploringSec” to get $50 off your registration

• Learn more about ShowMeCon: showmecon.com

• Register for Training or the Conference: Registration Link

• Event Venue and Room Block Information: Ameristar Casino & Resort

• Connect with the Founder of ShowMeCon Dave Chronister: LinkedIn Profile

• Connect with the Head Organizer for ShowMeCon Brooke Deneen: LinkedIn Profile

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In this episode of Exploring Information Security, host Timothy De Block welcomes Kevin Johnson, founder of Secure Ideas, to discuss web application penetration testing, API security, and hands-on security training. Kevin shares insights on why pentesters need to understand business risk, how API security is often misunderstood, and what participants can expect from his Breaking Bad Code workshop at ShowMeCon. He also reflects on the state of security talks at conferences, the importance of interactive learning, and Secure Ideas’ 15-year journey in the industry.

• Web Application Security Challenges – Why automated tools alone aren’t enough, and how attackers think differently.

• API Security & Misconceptions – How APIs change attack surfaces and why developers often overlook key security flaws.

• Breaking Bad Code Training at ShowMeCon – What attendees will learn and why hands-on hacking beats passive lectures.

• Security Talks vs. Vendor Pitches – The problem with sales-driven conference talks and why real education matters.

• The Evolution of Secure Ideas – Celebrating 15 years in business, plus challenge coins and community growth.

• Fun Side Tangents – Muppets, hacking culture, and why Wacka Hack is the talk you don’t want to miss at ShowMeCon.

• Effective pentesting goes beyond tools—it’s about understanding the purpose and risk of an application.

• API security isn’t a separate discipline—it requires a shift in attacker mindset.

• Hands-on training is the best way to learn—expect to actively hack at the Breaking Bad Code workshop.

• Security conference talks should educate, not sell—vendor-heavy presentations fail to engage the audience.

• ShowMeCon is an invaluable event for anyone interested in offensive security and application security.

• Kevin Johnson – Founder & CEO of Secure Ideas, security consultant, trainer, and conference speaker.

• Follow Kevin on Twitter: @SecureIdeas

• Secure Ideas: secureideas.com

• Samurai WTF – Web Testing Framework: samuraiwtf.org

• Penetration Testing Execution Standard (PTES): pentest-standard.org

Use the promo code “ExploringSec” to get $50 off your registration

• Learn more about ShowMeCon: showmecon.com

• Register for Training or the Conference: Registration Link

• Event Venue and Room Block Information: Ameristar Casino & Resort

• Connect with the Founder of ShowMeCon Dave Chronister: LinkedIn Profile

• Connect with the Head Organizer for ShowMeCon Brooke Deneen: LinkedIn Profile

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Use the promo code “ExploringSec” to get $50 off your registration

In this episode of Exploring Information Security, host Timothy De Block welcomes Amanda Berlin, CEO of Mental Health Hackers & Senior Product Manager at Blumira, to discuss her experiences in security product development, incident detection, and the challenges of balancing security with usability. They explore the limitations of pentest reports, the practicality of security automation, and the psychology behind effective security awareness training. Amanda also shares insights on how small businesses can implement security without breaking the bank and what to expect from ShowMeCon.

• Amanda’s Keynote at ShowMeCon – How she ended up speaking and why Dave’s method of picking speakers is unconventional.

• Security Automation vs. Usability – Why some industries can implement auto-lockouts, while others (like hospitals) cannot.

• The Problem with Pentest Reports – Why they often contain unrealistic security expectations that don’t translate to real-world environments.

• Getting Buy-In for Security Solutions – How to understand what organizations actually need instead of pushing the latest security trend.

• The Role of Nudge Theory in Awareness Training – Why small, repeated reinforcements can be more effective than long training videos.

• Security for Small Businesses – Strategies for implementing security on a limited budget and making defenses practical.

• Side Tangents & Fun Conversations – Crossword puzzles, Wordle streaks, and the absurdity of marketing budgets in cybersecurity.

• Security needs to be tailored to the environment—automation can improve security, but in some cases, it can create more risks.

• Pentest reports often miss the mark by listing detected issues without considering operational feasibility.

• Security awareness is most effective when it’s continuous and engaging, rather than a one-time annual training.

• Listening to users is critical—security teams must balance technical controls with usability needs.

• ShowMeCon continues to be a top-tier conference for hands-on security learning and industry networking.

• Learn more about ShowMeCon: showmecon.com

• Register for Training or the Conference: Registration Link

• Event Venue and Room Block Information: Ameristar Casino & Resort

• Connect with the Founder of ShowMeCon Dave Chronister: LinkedIn Profile

• Connect with the Head Organizer for ShowMeCon Brooke Deneen: LinkedIn Profile

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In this episode of Exploring Information Security, host Timothy De Block sits down with James Pope, Vince Stoffer, and Blake Cahen from Corelight to discuss Capture The Flag (CTF) competitions and how they can be an invaluable learning tool for security professionals. Whether you're new to CTFs or a seasoned competitor, this episode covers everything from getting started to advanced strategies. The conversation dives into network-based CTFs, the skills required, and how Corelight’s own CTF events offer hands-on experience in network forensics.

• What is a CTF? Understanding how security CTF competitions work and what skills they test.

• Getting Started with CTFs: Tips for beginners, from choosing the right event to practicing with the right tools.

• Network Forensics and Security Analysis: How network-based CTFs differ from other styles and what data sources are most valuable.

• Common Pitfalls and Mistakes: Strategies to avoid overthinking problems and making costly errors during competitions.

• AI and the Evolution of CTFs: How AI is impacting CTF challenges and whether it’s changing how competitions are designed.

• James Pope – Director of Technical Marketing & Enablement at Corelight and experienced CTF organizer.

• Vince Stoffer – Field CTO at Corelight, with a background in network security and incident response.

• Blake Cahen – Security expert with experience in offensive cyber operations and threat hunting.

• Learn more about Corelight: Corelight Website

• Learn about Zeek: Zeke Open Source Site

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In this episode of Exploring Information Security, host Timothy De Block sits down with JC, President at Snowfensive, to discuss Windows forensics, incident response, and the upcoming training session at ShowMeCon. JC shares insights on real-world forensic investigations, common challenges organizations face in responding to incidents, and how forensic methodology plays a critical role in cybersecurity operations. This episode is packed with valuable information for security professionals, IT admins, and anyone interested in digital forensics.

• Learn more about ShowMeCon: showmecon.com

• Register for Training or the Conference: Registration Link

• Event Venue and Room Block Information: Ameristar Casino & Resort

• Connect with JC: LinkedIn Profile

• Connect with the Founder of ShowMeCon Dave Chronister: LinkedIn Profile

• Connect with the Head Organizer for ShowMeCon Brooke Deneen: LinkedIn Profile

• ShowMeCon Training Session: What attendees can expect from JC’s Windows forensics course.

• The Reality of Incident Response: The distinction between forensic analysis and incident response and how they complement each other.

• Ransomware Trends: The evolution from encryption-based ransomware to data extortion and the impact on organizations.

• Real-World Forensic Cases: Examples of forensic investigations, including rapid containment strategies and detecting data exfiltration.

• Critical Thinking in Forensics: How forensic methodology is akin to detective work, and why troubleshooting skills are essential.

• Challenges in Reporting: Why documenting forensic findings properly is just as important as the investigation itself.

• Organizations are improving at responding to ransomware but still struggle with preventing data exfiltration.

• Understanding Windows forensic artifacts is crucial for both security teams and IT administrators.

• Effective forensic investigations require both technical expertise and strong reporting practices.

• Training and tabletop exercises are essential for preparing organizations to handle real-world incidents.

• JC is a cybersecurity expert specializing in Windows forensics, incident response, and offensive security services. He is the President of Snowfensive and Co-Founder of the Social Engineering Community.

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In this episode of Exploring Information Security, host Timothy De Block sits down with Dave Chronister and Brooke Deneen to discuss ShowMeCon, the Midwest’s premier security conferences. Dave shares the vision behind ShowMeCon, how it stands apart from other security events, and what attendees can expect from the 2025 edition. Brooke provides insights into the logistics of running the conference and the community-driven experience that makes it special. Whether you're a seasoned security professional or new to the space, this episode highlights why ShowMeCon is a must-attend event.

Use ExploringSec to get $50 off.

• Learn more about ShowMeCon: showmecon.com

• Register for Training or the Conference: Registration Link

• Event Venue and Room Block Information: Ameristar Casino & Resort

• Connect with Dave Chronister: LinkedIn Profile

• Connect with Brooke Deneen: LinkedIn Profile

• The Origin of ShowMeCon: How the conference came to be and its unique place in the cybersecurity event landscape.

• Balancing Corporate and Hacker Culture: Creating a professional yet welcoming environment that bridges the gap between security research and IT professionals.

• Venue and Experience: Why the Ameristar Casino in St. Louis is an ideal location and what makes the event an immersive experience.

• Speaker and Attendee Engagement: The focus on quality content, hands-on learning, and ensuring speakers are passionate and approachable.

• Expanding to New Cities: Plans to bring the ShowMeCon model to new locations like Nashville and beyond.

• ShowMeCon 2025 Highlights: The return of pre-conference training, CTFs, lockpicking villages, and an exciting Fallout-themed experience.

• Building a Security Community: Encouraging new speakers, creating a welcoming space, and fostering professional development.

• ShowMeCon is designed for practical security education, offering content relevant to both IT and security professionals.

• The conference prides itself on being a well-run, high-quality event where speakers and attendees engage meaningfully.

• Training opportunities and community events, such as CTFs and lockpicking villages, enhance the overall experience.

• ShowMeCon’s future includes expansion to other cities and continued efforts to foster an inclusive and passionate security community.

• Dave Chronister is the founder of ShowMeCon and a cybersecurity professional with over 18 years of experience in the industry.

• Brooke Deneen plays a key role in organizing ShowMeCon and ensuring the event runs smoothly.

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In this episode of Exploring Information Security, host Timothy De Block sits down with Dr. Paul Ashley, privacy expert and leader at Anonyome Labs, to discuss how individuals and organizations can take control of their digital privacy. They explore the growing need for online anonymity, the benefits of using pseudonymous identities, and the challenges posed by modern surveillance and data collection practices. Dr. Ashley provides insights into privacy-enhancing technologies and practical strategies for safeguarding personal information online.

• The Origin of Anonyomy Labs: How a team of enterprise security professionals created solutions to bring corporate-grade privacy to everyday users.

• The Concept of Pseudonymous Identities: How services like MySudo allow users to compartmentalize their digital presence and limit personal data exposure.

• Privacy for Everyday Users vs. High-Risk Individuals: Use cases ranging from avoiding spam to secure communications for journalists and whistleblowers.

• Virtual Credit Cards and Secure Transactions: Reducing financial risk when shopping online and protecting personal banking details.

• Privacy Challenges in Social Media and Online Accounts: How users can limit tracking, reduce unwanted exposure, and navigate social media restrictions.

• Decentralized Identity and the Future of Online Authentication: The emerging shift from centralized logins to self-sovereign identity management.

• Practical Steps to Improve Privacy: Simple actions users can take to start protecting their online presence today.

• Personal privacy requires active management—tools like MySudo help compartmentalize information to reduce exposure.

• Using pseudonyms, temporary email addresses, and virtual credit cards can help protect against identity theft and financial fraud.

• Social media platforms attempt to correlate identities, making it essential to separate accounts and use different networks.

• Enterprises can also benefit from privacy-focused solutions to ensure secure communication and limit data leaks.

• The move toward decentralized identity will reshape online authentication, offering greater control to individuals.

Dr. Paul Ashley is a privacy advocate and security expert at Anonyomy Labs, working to develop privacy-focused technologies that empower individuals and organizations. You can learn more about Anonyomy Labs and their privacy solutions at Anonyome Labs.

• Learn more about MySudo: mysudo.com

• Connect with Dr. Paul Ashley: LinkedIn Profile

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In this episode of Exploring Information Security, Timothy De Block welcomes Erin Barry, a recruiter with nearly a decade of experience specializing in software development and security roles. Erin shares her insights into the current job market landscape, recruitment trends, and the evolving expectations for candidates in tech and security sectors. Whether you're a job seeker or an employer, this episode is packed with valuable takeaways on hiring practices, remote work dynamics, and the impact of AI on recruitment.

• The Current Job Market: Erin discusses the heightened competition for roles, the evolving expectations from employers, and why remote work is no longer the standard but a perk.

• Recruitment in Tech and Security: Insights into hiring for startups, the rise of AI-focused roles, and how companies are adapting to the rapid evolution of technology.

• AI in Recruitment: Erin and Timothy talk about the misuse of AI in interviews, the challenges of identifying true expertise in AI, and tools being developed to combat deep fakes in recruitment.

• Job Seeker Tips: Erin offers actionable advice for candidates, including the importance of researching companies, maintaining an online presence (e.g., GitHub, blogs), and avoiding AI during interviews.

• Hiring Trends: Erin highlights the demand for roles in product and application security, blockchain, and AI, and shares her observations on the types of candidates employers are seeking in these fields.

• Startups are increasingly adopting hybrid work models with occasional in-person collaboration.

• Companies are becoming pickier in hiring and extending interview processes to ensure the right fit.

• Candidates claiming expertise in AI and blockchain are often scrutinized for authenticity.

• Remote roles are becoming more competitive and limited, with a preference for local or hybrid arrangements.

• Job seekers should invest in building an online portfolio, such as maintaining a GitHub page or personal blog, to stand out.

Erin Barry is a seasoned recruiter at Code Red Partners with extensive experience placing candidates in cutting-edge tech roles. She specializes in the software development lifecycle and security positions, working primarily with startups in San Francisco, Seattle, and beyond. You can follow Erin on LinkedIn for the latest job opportunities and industry insights: Erin Barry's LinkedIn.

• Learn more about Code Red Partners: coderedpartners.com

Leave a comment below or reach out via the contact form on the site, email timothy.deblock[@]exploresec[.]com, or reach out on LinkedIn.

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In this episode of Exploring Information Security, host Timothy De Block sits down with Brian Dye from Corelight to discuss the evolution of cybersecurity, the importance of Network Detection and Response (NDR), and the challenges modern organizations face with securing their networks. Brian shares valuable insights into how Corelight leverages open-source technologies and data to provide advanced threat detection and forensics.

• The Evolution of Corelight
  Brian discusses the history of Corelight, the transition from the open-source project Zeek (formerly Bro) to the Corelight company, and the importance of supporting the open-source community. He also touches on how the company has grown as cybersecurity needs have evolved.

• Network Detection and Response (NDR)
  Corelight's NDR solutions help organizations detect advanced threats that bypass traditional security controls like firewalls and EDR. Brian explains the differences between EDR and NDR, and why both are essential for a comprehensive cybersecurity strategy.

• AI and Machine Learning in Security
  Brian dives into how Corelight has embraced AI and machine learning, particularly with generative AI (GenAI), to improve threat detection and response capabilities. He shares examples of how organizations are using GenAI to automate security workflows and accelerate alert investigations.

• The Changing Threat Landscape
  Brian talks about how attackers are evolving their tactics, moving away from malware-based attacks to techniques like "living off the land" (LoL) to avoid detection. He discusses the importance of understanding these advanced attack methods and how NDR tools help provide the data needed to investigate and respond.

• Real-World Success Stories
  Brian shares examples of how Corelight has helped organizations respond to cyber threats, including a ransomware attack scenario where Corelight's tools provided the necessary data to help the victim organization make informed decisions about whether to pay a ransom.

• The Future of Network Security
  Looking ahead, Brian outlines the future of Corelight and its focus on expanding its data capabilities to enable more advanced detections. He highlights the importance of data as a foundational element for security and how Corelight plans to continue innovating in the NDR space.

Brian Dye is the Chief Product Officer at Corelight, a leading provider of Network Detection and Response (NDR) solutions. With years of experience in cybersecurity, Brian is dedicated to helping organizations defend against advanced threats using open-source tools and innovative technology.

• Corelight Website

• Zeek Project

• Corelight's Open-Source Threat Hunting Guides

• Corelight Blog

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