Simply Offensive - Archive

Nicolas Chaillan on AI Replacing Jobs, National Security, and Staying Relevant in the AI EraEpisode SummaryIn this episode of Simply Offensive, host Phillip Wylie sits down with entrepreneur and former U.S. Air Force and Space Force Chief Software Officer Nicolas Chaillan. Nicolas shares his journey from coding at age seven to founding multiple companies, working in government leadership, and building AI-driven businesses.The conversation explores the rapid evolution of AI, the reality of job displacement, how AI agents are already replacing entire teams, and what skills professionals need to remain relevant. Nicolas

In this episode of Simply Offensive, host Phillip Wylie sits down with Denis Calderone, Co-Founder and Principal at Suzu Labs, to discuss his journey from early curiosity about how technology works to building a long career in cybersecurity consulting and penetration testing.Denis shares stories from the early days of security when breaches often went unnoticed, how compliance shaped the industry, and how today’s AI-driven development is creating both opportunity and risk. The conversation explores the evolution of pentesting, the importance of community in hiring, the growing role of AI in offensive

In this episode of Simply Offensive, host Phillip Wylie sits down with cybersecurity leader Christopher Marks to discuss his journey from networking into security leadership, the importance of offensive security knowledge for defenders, and how AI is changing security operations.Christopher shares how community involvement, mentorship, and hands-on offensive security training helped shape his career and leadership philosophy. The conversation explores why security teams benefit from understanding attacker techniques and how organizations can improve resilience through purple team exercises and realistic simulations.Connect with Christopher Marks:LinkedIn: https://www.linkedin.com/in/christopher-m-7357441b/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube:

In this episode, Phillip Wylie interviews cybersecurity expert Josh Mason about his journey from military service to cybersecurity, his book on communicating security to business leaders, and his initiatives like Noob Village to support newcomers at conferences like DEF CON.Connect with Josh Mason:LinkedIn: https://www.linkedin.com/in/joshuacmason/Noob Community Website: https://www.noobvillage.org/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/Chapters00:00 Introduction to Cybersecurity Journeys02:57 Transitioning from Military to Cybersecurity04:56 Communicating Cybersecurity in Business08:18 Inspiration Behind the Book12:06 Creating a New Village for Newbies14:55 Building the Newbs Community at

In this episode of Simply Offensive, Phillip Wylie interviews Dan DeCloss, founder of PlexTrack, discussing the evolution of cybersecurity, the importance of report writing in pen testing, and the impact of AI on the industry. Dan shares his unique origin story, insights on the challenges of report writing, and how PlexTrack aims to streamline the process. The conversation also explores the future of AI in cybersecurity and its implications for the job market.Connect with Dan DeCloss:LinkedIn: https://www.linkedin.com/in/ddecloss/PlexTrac Website: https://plextrac.com=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways

In this episode, Phillip Wylie and Jacob Krell discuss the integration of AI in Capture The Flag (CTF) competitions and its implications for cybersecurity. Jacob shares his experiences with AI in penetration testing, highlighting how it enhances efficiency and changes the competitive landscape. They explore the future of certifications, the importance of human skills, and the ethical considerations surrounding AI in cybersecurity.Connect with Jacob:⁠https://www.linkedin.com/in/jacob-krell/⁠⁠https://x.com/hackerfren⁠=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/

In this episode, Darius Houle joins the conversation to explore the real-world limitations of AI in problem-solving and why context matters more than most people realize. The discussion covers how AI systems struggle with nuanced tasks, why developers must understand the boundaries of these tools, and how clearer prompts can dramatically improve outcomes.Darius shares insights from his experience in application security, tool building, and community leadership. The conversation also highlights the growing role of AI in cybersecurity testing and the responsibility developers have when integrating AI into their workflows.========================= Connect with

In this episode, Phillip Wylie interviews Matt Brown, a hardware hacker and content creator, discussing his journey in technology, the fundamentals of hardware hacking, and the importance of affordable training. They explore the impact of content creation on career opportunities, the significance of community and conferences in the field, and provide advice for aspiring content creators. Matt shares insights on his recent milestone of reaching 200,000 subscribers on YouTube and emphasizes the value of sharing knowledge and learning in the hardware hacking space.========================= Connect with Matt BrownYouTube Channel: https://www.youtube.com/@mattbrwnLinkedIn: https://www.linkedin.com/in/mattbrwn/Website: https://brownfinesecurity.com/Training:

In this episode of Simply Offensive, Phillip Wylie interviews Dahvid Schloss, a cybersecurity expert and the emulated mob boss of emulated criminals. They discuss Dahvid's background in the military and cybersecurity, the differences between red teaming and pen testing, the importance of red teaming in understanding real risks, and the role of purple teaming in improving security practices. They also delve into the significance of tooling in adversarial emulation, the planning involved in red team operations, and the impact of AI on red teaming. The conversation concludes with Dahvid sharing insights

SummaryIn this episode of Simply Offensive, Phillip Wylie interviews Mike Bell, CEO of Suzu Labs, discussing the intersection of cybersecurity and AI. They explore the OWASP Top 10 vulnerabilities, focusing on prompt injection attacks and their implications. Mike demonstrates real-world attack scenarios, emphasizing the importance of input sanitization and risk mitigation in AI systems. The conversation concludes with resources for learning AI security and best practices for pen testing.TakeawaysAccurate asset inventory is crucial for security.AI and cybersecurity are converging fields.Prompt injection can manipulate AI responses.Indirect prompt injection is a hidden threat.Training

In this episode of Simply Offensive, Phillip Wylie sits down with Len Noe (HaCkEr_213) — the world’s first recognized augmented ethical hacker. From microchip implants and implantable terabyte drives to a past life in outlaw motorcycle clubs, Len’s story sits at the collision point of human and machine identity.Connect with Len:https://www.linkedin.com/in/len-noe/https://i-am-machine.com/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie interviews Shubham Khichi, an offensive security professional and founder of CyberAGI. We explore Shubham's journey in cybersecurity, the challenges faced by security engineers, and the innovative solutions offered by CyberAGI.We also discuss the role of AI in penetration testing, the importance of human involvement in automation, and how professionals can future-proof their careers in an evolving landscape.Shubham shares the need for trust in technology and the value of making cybersecurity tools accessible and effective for engineers.Connect with Shubham:https://www.linkedin.com/in/shubhamkhichi=========================Connect with your host, Phillip Wylie:LinkedIn:

In this episode of Simply Offensive, Phillip Wylie interviews Daniel Lowrie, who shares his extensive background in IT and cybersecurity, particularly in penetration testing and education.Daniel discusses his journey from IT to teaching, effective learning strategies for aspiring pen testers, the importance of hands-on experience, and engaging teaching techniques.He emphasizes the need for personal branding in cybersecurity and offers advice for those starting their careers in this field. Tune in now to learn more!Connect with Daniel:https://www.linkedin.com/in/daniellowriehttps://www.youtube.com/@daniellowriehttps://academy.simplycyber.io/l/pdp/the-complete-pentest-course-pt0-003=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with

In this episode of Simply Offensive, Phillip Wylie interviews Mike Holcomb, an expert in Operational Technology (OT) and Industrial Control Systems (ICS) cybersecurity.Mike discusses the importance of OT security, the types of attacks that have targeted critical infrastructure, and the evolving landscape of cybersecurity threats. He shares insights on the significance of safety in OT environments, the challenges of pentesting in these settings, and the tools and techniques used for effective security assessments.We also touch on the role of AI in enhancing OT security and the resources available for those looking

In this episode of Simply Offensive, Phillip Wylie interviews Danny Jenkins, CEO and founder of ThreatLocker.Danny shares his unique journey from corporate IT to ethical hacking, discussing his innovative approach to penetration testing and cybersecurity. He emphasizes the importance of understanding technology and security configurations, the role of living off the land binaries in modern attacks, and how ThreatLocker implements a zero trust model to enhance security.This episode also covers community engagement through events and the significance of hands-on learning in cybersecurity. Join us to learn more!Connect with Danny Jenkins on

In this episode of Simply Offensive, Phillip Wylie is joined by Greg Hatcher and John Stigerwalt from White Knight Labs.They discuss their backgrounds in cybersecurity, the importance of advanced penetration testing, and the unique offerings of their training courses. The conversation covers various aspects of cybersecurity, including ransomware simulations, compliance, physical pen testing, and how to become an advanced pen tester.Greg and John share insights into their methodologies and the gaps they see in current security practices, emphasizing the need for companies to adopt more robust security measures.Connect with Greg and

In this episode of Simply Offensive, Phillip Wylie is joined by Jacob Krell, a cybersecurity professional with a wealth of certifications and experience. Jacob shares his journey into the world of hacking, the importance of personal branding, and how to avoid burnout while pursuing certifications.He discusses the significance of CVEs, the role of platforms like Hack The Box in skill development, and the integration of AI in cybersecurity. Jacob emphasizes the need for discipline and continuous learning in achieving success in the field.Connect with Jacob:https://www.linkedin.com/in/jacob-krell/https://x.com/hackerfren=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube:

Welcome to the Season 2 premiere of Simply Offensive. In this episode of Simply Offensive, Phillip Wylie is joined by Corey LeBleu, a cybersecurity professional with over 20 years of experience in penetration testing.Tune in to learn about Corey's background - and his experience being arrested while on a pentest.Corey has expertise across multiple domains including network pentesting, social engineering, physical security assessments, and web application security. He discovered CVEs for major vendors including Apple and Citrix, and currently runs his own consulting firm, Relix Security.Connect with Corey:https://www.linkedin.com/in/coreylebleu/https://www.relixsecurity.com/=========================Connect with your host,

In this episode of Simply Offensive, Phillip Wylie is joined by Tyler Ramsbey, a penetration tester and content creator.Learn about Tyler's unique journey into cybersecurity, the importance of soft skills, and the value of teaching and content creation.Tyler shares insights on maintaining mental health, balancing family life, and his upcoming venture into entrepreneurship with a focus on quality pen testing services.The conversation emphasizes the significance of personal branding, effective communication, and the need for emotional intelligence in the tech industry.You do not want to miss this Season 1 finale episode!Connect with

In this episode of Simply Offensive, Phillip Wylie is joined by Tim Shipp to discuss various aspects of cybersecurity, including the evolution of the field over the past 25 years, the importance of offensive security, and the challenges faced by both red and blue teams.Tim shares his extensive background in cybersecurity, touching on incident response, the monetization of cyber attacks, and the significance of basic security hygiene. The discussion also emphasizes the need for collaboration between offensive and defensive security practices, as well as offering advice for newcomers to the industry.Tim's

In this episode of Simply Offensive, Phillip Wylie is joined by Cathy Ullman, a principal technology architect in cybersecurity.Join us as we discuss Cathy's journey in the cybersecurity field, the evolution of security tools and threats, the importance of understanding offensive security, and the value of purple teaming.Cathy shares insights on leveraging cyber threat intelligence and the MITRE ATT&CK framework, as well as advice for getting involved in the cybersecurity community.This conversation emphasizes the need for defenders to understand the offensive mindset to enhance their security posture. Tune in to learn

In this episode of Simply Offensive, Phillip Wylie interviews Rob Allen, Chief Product Officer at ThreatLocker. Learn about the importance of proactive security measures, particularly in the context of ransomware prevention.Rob shares his journey to ThreatLocker and the company's unique approach of 'deny by default' in endpoint security. The conversation also touches on the significance of controls validation, the risks associated with low bins, and real-world examples of how these concepts apply in cybersecurity.Gain insights on upcoming events and the value of continuous learning in the field. Rob Allen's LinkedIn: https://www.linkedin.com/in/threatlockerrob30-day

In this powerful and heartfelt episode of Simply Offensive, Phillip Wylie is joined by Joe Brinkley, better known as The Blind Hacker, Founder of the DeadPixelSec community, and a seasoned offensive security professional.Joe shares his journey from sysadmin to red teamer, his philosophy on mentorship, and candid insights on burnout in cybersecurity.Whether you're breaking into the field or leveling up, this episode offers invaluable advice on growth, community, and sustainability.Connect with Joe Brinkley on LinkedIn: https://www.linkedin.com/in/brinkleyjoseph/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with

In this episode of Simply Offensive, host Phillip Wylie welcomes offensive security veteran Ben Thal for a deep dive into the world of red teaming, penetration testing, and breaking into offensive security.With over a decade of experience across red teaming, pen testing, and hardware hacking, Ben brings practical insights for anyone interested in or currently navigating the field.Connect with Ben Thal on LinkedIn:https://www.linkedin.com/in/benjamin-l-thal/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu LabsAll the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/=========================Sponsored by @ThreatLocker Allow what you need, block everything else... Including ransomware. Zero

In this episode of Simply Offensive, Phillip Wylie interviews Amélie Koran, a seasoned expert in offensive security and AI red teaming.They discuss the evolution of red teaming, the challenges and opportunities presented by AI in security, and the importance of human expertise in navigating the complexities of cybersecurity.The conversation also touches on the differences between federal and corporate security practices, the significance of security clearances, and the need for organizations to reevaluate their security tools and practices.Connect with Amélie Koran on LinkedIn:https://www.linkedin.com/in/webjedi=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu

In the inaugural episode of the Simply Offensive podcast, host Phillip Wylie interviews Michael Kim, a cybersecurity professional with a diverse background.Michael shares his journey from music to cybersecurity, emphasizing the importance of networking, certifications, and continuous learning. He discusses the challenges of breaking into pen testing, the interview process, and the significance of coding skills in the field.The conversation highlights the value of experience, both formal and informal, and encourages aspiring pen testers to leverage their training and connections to succeed in the industry.Connect with Michael Kim on LinkedIn: https://www.linkedin.com/in/michael-k-83b0627b/=========================Connect