Phillip Wylie Show | Cybersecurity & Pentesting Podcast

In this episode of The Phillip Wylie Show, Phillip sits down with Marie Hamilton to explore her unconventional and inspiring path into cybersecurity. From early curiosity about computers and creative problem-solving as a teenager to serving in the military, navigating career pivots, and ultimately launching her own cybersecurity and investigations business, Marie shares a candid look at her journey. They discuss the realities of breaking into cybersecurity, the value of community and networking, lessons learned from entrepreneurship, and how emerging technologies like AI are shaping the future of the field. Marie also dives into her current work in digital forensics, OSINT, and cyber law, offering valuable insights for anyone looking to enter or grow in the industry. ========================= Connect with Marie Hamilton: LinkedIn: https://www.linkedin.com/in/wcymar2/ Opis website: https://www.opis-cybersecurity.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

How do you go from professional wrestling and powerlifting to a career in cybersecurity and penetration testing? In this special solo episode of The Phillip Wylie Show, Phillip Wylie shares his personal hacker origin story and the unconventional path that led him from wrestling matches and construction jobs to becoming a penetration tester, security evangelist, author, and podcast host. If you're trying to break into cybersecurity, transition from IT, or wondering if it's too late to start, this episode shows that there is no single path into security. Phillip discusses how curiosity, persistence, mentorship, public speaking, and content creation helped shape his career and how you can apply these same principles to your own journey.========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of The Phillip Wylie Show, host Phillip Wylie sits down with offensive security professional Jamy Casteel to discuss his journey from small-town IT technician to penetration tester and red teamer. Jamy shares how an early exposure to social engineering and physical pentesting sparked his interest in security and shaped his career path. The conversation explores the differences between pentesting and red teaming, the value of consulting experience, and why understanding business risk is just as important as technical skill. Jamy also shares his thoughts on certifications versus real-world experience, the emerging role of AI in security testing, and why cybersecurity professionals should develop interests outside of technology to maintain balance and mental clarity. This episode offers practical advice for aspiring cybersecurity professionals along with insights into how offensive security continues to evolve. ========================= Connect with Jamy Casteel: LinkedIn: https://www.linkedin.com/in/jamy-casteel ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of the Phillip Wylie Show, host Phillip Wylie sits down with cybersecurity professional Travis Stein to discuss practical strategies for breaking into cybersecurity, building technical skills, and advancing from IT into security roles. Travis shares his journey from help desk roles into cybersecurity engineering and offers actionable advice for aspiring professionals looking to stand out in a competitive field. The conversation highlights the importance of hands-on experience, networking, home labs, certifications, and building a personal portfolio to demonstrate real-world skills. Travis also discusses how soft skills like communication and presentations can accelerate career growth and open new opportunities. ========================= Connect with Travis Stein: LinkedIn: https://www.linkedin.com/in/twstein86/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode, Phillip Wylie sits down with Dr. Gregory Carpenter to explore his journey from early childhood curiosity to a distinguished career in cybersecurity, military operations, and advanced threat modeling. Greg shares how his early interest in security evolved from physical lockpicking and unconventional problem solving into work involving digital security, NSA operations, and space-related missions. The conversation dives into what effective threat modeling really looks like and why too many security assessments fail to account for real-world conditions. Greg explains the importance of looking beyond traditional network boundaries to include physical access, RF exposure, social engineering, environmental conditions, and human behavior. He also discusses the limits of narrowly scoped pen tests and why deeper, more realistic engagement is critical for understanding how attackers actually operate. Phillip and Greg also examine the growing role of AI and automation in offensive security. Greg shares his perspective on how AI can improve security assessments, where automation adds value, and why creativity and adaptability still matter just as much as tools. They also cover dynamic defenses, deception, critical infrastructure risk, and how organizations can use intelligence sources such as MITRE, DOD, FBI, and DHS to strengthen their defensive strategies. ========================= Connect with Gregory Carpenter: LinkedIn: https://www.linkedin.com/in/gcarpenter-cso-kbi/ Gregory's book: https://www.amazon.com/Reverse-Deception-Organized-Counter-Exploitation-McGraw-Hill/dp/B00E6T3VRA/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of the Phillip Wylie Show, Allie Mellen shares her journey from a computer engineering student to a cybersecurity expert and industry analyst. She discusses the importance of hands-on experience in cybersecurity, the evolution of cybersecurity tools, and the significance of a hacker mindset. Allie also emphasizes the need for clear communication in cybersecurity for non-technical audiences and provides advice on selecting cybersecurity products. Additionally, she introduces her new book, 'Code Nations,' which explores the intersection of cybersecurity and geopolitics, highlighting the impact of global events on cyber warfare strategies. ========================= Connect with Allie Mellen: LinkedIn: https://www.linkedin.com/in/hackerxbella/ Allie's book: https://www.amazon.com/dp/1394285574 ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Eve Maler, a prominent figure in identity security. They discuss the importance of community in cybersecurity, Eve's journey into the field, the evolution of identity technologies like SAML and OAuth, advancements in authentication methods, and the impact of AI on identity management. Eve also shares insights from her upcoming book on digital identity, emphasizing the need for a user-centric approach to security. ========================= Connect with Eve Maler: LinkedIn: https://www.linkedin.com/in/evemaler/ Eve's book: https://masteringdigitalidentity.com/ Website: https://www.vennfactory.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode, Sudhanshu Chauhan discusses the transformative impact of AI on the cybersecurity landscape. He explains how AI has introduced new attack vectors and the dual nature of AI in cybersecurity, serving both as a tool for attacks and as a target for attacks. The conversation emphasizes the need for security professionals to adapt to these changes and explore innovative approaches to penetration testing and security measures. ========================= Connect with Sudhanshu Chauhan: LinkedIn: https://www.linkedin.com/in/sudhanshuchauhan Website: https://redhuntlabs.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of the Phillip Wylie Show, Dorota Kozlowska shares her inspiring journey from a hesitant high school student to a successful professional in offensive security and content creation. She discusses her challenges in breaking into the male-dominated field of cybersecurity, her passion for pen testing, and her commitment to empowering other women in tech through her podcast, 'The Woman in Red.' Dorota emphasizes the importance of personal branding, continuous learning, and the courage to pursue one's dreams despite obstacles. ========================= Connect with Dorota Kozlowska https://www.linkedin.com/in/dorota-kozlowska/ https://www.woman-in-red.com/ https://www.youtube.com/@womaninredpresents ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of the Phillip Wylie Show, host Phillip Wylie welcomes cybersecurity expert Keelan Knox, who shares his fascinating hacker origin story. Keelan recounts his early curiosity about technology, which led him to dismantle various devices and eventually discover the world of hacking and cybersecurity. He emphasizes the importance of social engineering in the field and how it became a natural skill for him. The conversation delves into Keelan's educational background, his diverse roles in cybersecurity, and the significance of networking in building a successful career in the industry. As the discussion progresses, Keelan offers valuable advice for aspiring cybersecurity professionals, highlighting the importance of understanding one's interests and strengths. He shares insights on how to effectively communicate technical concepts to non-technical stakeholders, emphasizing that cybersecurity should complement business objectives. The episode wraps up with Keelan discussing his ongoing learning methods, including hands-on practice in home labs and engaging with the cybersecurity community at conferences. This episode is a treasure trove of insights for anyone interested in pursuing a career in cybersecurity or enhancing their skills in the field. ========================= Connect with Keelan Knox https://www.linkedin.com/in/mrkknox/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with Michael Farnum and Sam Van Ryder to discuss the growth of CYBR.SEC.Community, formerly known as HOU.SEC.CON. They share their hacker origin stories and how a grassroots conference evolved into a national, community-driven cybersecurity movement. The conversation covers the expansion of CYBR.SEC.Community to include OT.SEC.CON, EXEC.SEC.CON, YOUTH.SEC.CON, CYBR.HAK.CON, and CYBR.SEC.Media, the community’s media platform focused on education, storytelling, and amplifying voices across the cybersecurity ecosystem. The episode highlights accessibility, youth and veteran involvement, bridging IT and OT security, and why curiosity and real-world experience remain essential to building the future of cybersecurity. ========================= Connect with Michael Farnum and Sam Van Ryder: https://www.linkedin.com/in/mfarnum/ https://www.linkedin.com/in/svanryder/ CYBR.SEC.Community Links: https://www.cybrsec.community/ https://www.cybrseccon.com/ https://www.otseccon.com/ https://www.cybrsec.community/execseccon https://www.cybrhakcon.com/ https://www.cscusergroup.com/ https://www.cybrsecmedia.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie/ =========================

In this episode of the Phillip Wylie Show, host Phillip’s guest is Travis Weathers, a seasoned professional in cybersecurity and penetration testing. Travis shares his unique journey from military service to becoming a successful entrepreneur in the cybersecurity field. He discusses the importance of specialized training, the differences between red teaming and traditional pen testing, and offers valuable advice for those looking to advance their careers in cybersecurity. The conversation also touches on the role of AI in the industry and the innovative tools being developed for physical pen testing. This episode is sponsored by Teleport, an identity-first security platform. Learn more: https://fandf.co/4p98SC6 ========================= Connect with Travis Weathers: https://www.linkedin.com/in/trweathers/ https://mwgroup.io/ https://vtemlabs.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: ⁠https://linkedin.com/in/phillipwylie⁠ X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie/ ========================= Chapters 00:00 Introduction and Guest Background 01:32 Travis Weathers' Hacker Origin Story 05:31 Transitioning to Business Ownership 09:33 Training and Course Offerings 13:01 Advice for Aspiring Pen Testers 18:17 Understanding Red Teaming vs. Pen Testing 21:50 Career Advancement Strategies 24:40 The Role of AI in Cybersecurity 27:31 Teleport Ad 30:09 Phillip Wylie Show Outro

Summary In this episode of the Phillip Wylie Show, Phillip welcomes Jason and Kevin from the Cyber Distortion Podcast, diving deep into their hacker origin stories and the evolution of their podcasting journey. Kevin shares his unconventional path from marketing and graphic design to IT, highlighting how a conversation about salaries led him to pursue Microsoft certifications and a long-standing career in technology. Jason recounts his early fascination with technology, from building science projects to coding on his first home computer, illustrating how his inquisitive nature laid the groundwork for his future in cybersecurity. The conversation shifts to their experiences in podcasting, detailing how their shared passion for technology and cybersecurity led them to create the Cyber Distortion Podcast. They discuss the challenges and joys of producing content, including their recent involvement in the IAM Machine documentary, which explores transhumanism and the impact of AI. As they prepare for their upcoming live event in North Texas, they emphasize the importance of community and collaboration in the tech space, inviting listeners to engage with their work and the hacker community. Connect with Kevin & Jason https://twitter.com/DistortionCyber https://www.linkedin.com/in/jason-popillion-cissp-863a464/ https://www.linkedin.com/in/kevin-pentecost-cissp-cism-ceh-cpt-mcse-cca-itil-f-4a61404/ https://www.youtube.com/@TheCyberDistortionPodcast https://cyberdistortionpodcast.com/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie YouTube: https://youtube.com/@PhillipWylie ========================= Chapters 00:00 Welcome and Introduction 01:32 Hacker Origin Stories: Kevin's Journey 03:28 Hacker Origin Stories: Jason's Journey 10:24 The Transition to Podcasting 14:40 Inspiration Behind the Podcast 19:54 Season Five Changes and Innovations 24:20 The Return of Vito 28:54 Building a Virtual Personality 33:03 The Art of Problem Solving 33:28 Creating the IAM Machine Documentary 42:12 Upcoming Events and Community Engagement

Summary In this episode of the Phillip Wylie Show, Phillip Wylie interviews Shubham Khichi, a cybersecurity expert and entrepreneur. They discuss Shubham's journey from a computer science student to the founder of CyberAGI, a company focused on enhancing cybersecurity through AI. The conversation covers the importance of human involvement in cybersecurity, innovative threat modeling techniques, and the role of AI in augmenting the capabilities of security professionals. Shubham emphasizes the need for privacy in AI applications and offers advice for aspiring pen testers, highlighting the significance of self-belief and continuous learning in the rapidly evolving tech landscape. This episode is sponsored by Teleport, an identity-first security platform. Learn more: https://fandf.co/4pVfIwk Connect with Shubham: ⁠ https://www.linkedin.com/in/shubhamkhichi⁠ https://www.cyberagi.ai/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie YouTube: https://youtube.com/@PhillipWylie ========================= Chapters 00:00 Introduction and Background 01:55 Shubham's Hacker Origin Story 04:39 The Importance of Human Element in Cybersecurity 07:20 Excalibur: A Human-Centric Security Platform 10:02 Building Intuitive Security Tools 11:45 The Role of Experience in Cybersecurity Startups 14:27 Understanding Red Teaming vs. Pen Testing 19:26 Inversion Theory in Threat Modeling 24:00 AI and Privacy in Cybersecurity 29:17 AI's Role in Augmenting Human Work 33:19 Advice for Aspiring Pen Testers 34:55 Closing Thoughts and Future Outlook

Summary In this episode of the Phillip Wylie Show, host Phillip Wylie interviews Ron Eddings, a prominent figure in cybersecurity and podcasting. They discuss Ron's journey into cybersecurity, his experiences in podcasting, and the evolution of Hacker Valley Media. The conversation delves into the importance of video and audio quality in content creation, the role of AI in cybersecurity, and the future of jobs in the industry. Ron shares insights on tools for penetration testing and the impact of AI on traditional cybersecurity roles, emphasizing the need for professionals to adapt and future-proof their careers in an AI-driven landscape. Takeaways Connect with Ron: https://www.linkedin.com/in/ronaldeddings/ https://hackervalley.com/ Connect with Phillip: LinkedIn https://www.linkedin.com/in/phillipwylie/ X (formerly Twitter) https://x.com/PhillipWylie Instagram https://www.instagram.com/phillipwylie/ Chapters 00:00 Introduction to Cybersecurity Podcasting 01:43 Ron Eddings' Hacker Origin Story 04:29 The Journey into Podcasting 06:33 Evolution of Hacker Valley Media 08:17 Understanding Video and Audio Quality 10:38 Lighting and Its Importance in Video Production 12:47 Color Grading and Post-Production Techniques 14:24 Marketing and Branding in Cybersecurity 17:00 AI Security Research and Prompt Injection 19:11 Tools for AI Pentesting 22:30 AI in Traditional Pen Testing 24:12 The Future of Cybersecurity with AI 27:09 Job Security in the Age of AI 29:18 The Importance of Education and Experience 32:53 Conclusion and Future Outlook 33:39 Outro

Summary In this episode of the Phillip Wylie Show, Phillip Wylie interviews Chris Glanden, a cybersecurity professional and podcaster. They discuss Chris's journey into cybersecurity, his experiences in podcasting, and his recent ventures into documentary filmmaking. The conversation also touches on public speaking, community engagement through events like the Lone Star Cyber Circus, and advice for aspiring podcasters. Chris shares insights on the importance of storytelling in cybersecurity and the impact of podcasts on listeners' lives. Takeaways Connect with Chris: https://www.linkedin.com/in/chrisglanden/ https://pr0ph-1t.com/ https://www.barcodesecurity.com/

Summary In this conversation, Gideon Rasmussen discusses the importance of understanding one's professional development areas and how to prepare for promotion. He emphasizes the need for individual contributors to demonstrate leadership and deliver solid performance over time to be considered for advancement. Takeaways Connect with Gideon: https://www.linkedin.com/in/gideonrasmussen/ Gideon's book: Program Architecture: Fight the Good Fight (Security, Audit and Leadership Series) https://www.amazon.com/Program-Architecture-Fight-Security-Leadership/dp/1032896000

Summary In this conversation, Christopher Russell emphasizes the importance of being well-rounded in the field of cybersecurity. He discusses the necessity of understanding both offensive and defensive strategies, as well as the need for security professionals to grasp the business aspects of their roles. Russell highlights that a successful CISO must not only be technically proficient but also understand how security tools can support and enhance business operations. Takeaways Connect with Christopher: https://www.linkedin.com/in/christopher-russell-5a9b20a7/

Summary In this episode of the Philip Wylie Show, host Phillip Wylie speaks with Ted Harrington, a fellow podcaster and author, about the hacker mindset and its implications in cybersecurity. They discuss the misconceptions surrounding hackers, the importance of curiosity and creativity, and how the hacker mindset can be applied beyond technology. Ted shares his personal journey into the world of hacking, the motivation behind his new book, and offers insights on building a personal brand in the cybersecurity field. The conversation concludes with a message of optimism regarding the future of cybersecurity and the role of hackers in creating a safer digital world. Takeaways Connect with Ted: https://www.tedharrington.com/ https://www.linkedin.com/in/securityted/ https://www.amazon.com/Inner-Hacker-New-Way-Thinking-ebook/dp/B0FQR1SWWH Chapters 00:00 Introduction to the Hacker Mindset 04:09 Ted Harrington's Hacker Origin Story 11:27 The Inspiration Behind 'Inner Hacker' 16:42 Defining the Hacker Mindset 20:12 Building a Personal Brand in Cybersecurity 26:46 Optimism in the Security Profession

Summary In this episode of the Philip Wylie Show, Bat shares her journey from a childhood fascination with computers to a career in cybersecurity, specifically in threat hunting. Bat discusses her early experiences with hacking, the transition from wanting to be a pen tester to discovering a passion for digital forensics, and the day-to-day responsibilities of a threat hunter. The conversation also touches on the importance of education, certifications, and the evolving role of AI in cybersecurity. Takeaways Connect with Bat: https://x.com/batlogged Chapters 00:00 Introduction to the Guest and Their Background 01:29 Bat's Hacker Origin Story 05:14 Career Path and Transition to Cybersecurity 10:14 Exploring Different Areas in Cybersecurity 12:24 Day-to-Day in Threat Hunting 17:49 Leveraging AI in Threat Hunting 19:28 Training and Experience for Threat Hunting 21:32 The Importance of Building Narratives in Security 24:07 Certifications and Their Value 27:12 The Value of Formal Education vs. Self-Study 29:06 Closing Thoughts on Defensive Security