Phillip Wylie Show

Phillip Wylie
  • 4.9 (18)
  • TECHNOLOGY
  • UPDATED WEEKLY

The Phillip Wylie Show is a premier cybersecurity podcast and media source for offensive security professionals. Hosted by Phillip Wylie, globally recognized ethical hacking expert, keynote speaker, and co-author of The Pentester Blueprint, the show features elite red team operators, penetration testers, and security leaders sharing real-world tradecraft, advanced tactics, career strategy, and insights on AI-driven cyber threats.

  1. Jamy Casteel: From Small Town IT to Offensive Security

    2D AGO

    Jamy Casteel: From Small Town IT to Offensive Security

    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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    32 min
  2. Travis Stein: Mastering Cybersecurity: Hands-On Skills and Networking Strategies

    MAR 24

    Travis Stein: Mastering Cybersecurity: Hands-On Skills and Networking Strategies

    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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    48 min
  3. Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing

    MAR 17

    Gregory Carpenter: Beyond the Network | Threat Modeling, AI, and Real-World Pen Testing

    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

    40 min
  4. Allie Mellen: Code War

    MAR 10

    Allie Mellen: Code War

    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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    29 min
  5. Eve Maler: The Evolution of Identity Security

    MAR 3

    Eve Maler: The Evolution of Identity Security

    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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    32 min
  6. Sudhanshu Chauhan: Navigating the New Landscape of Cyber Threats

    FEB 24

    Sudhanshu Chauhan: Navigating the New Landscape of Cyber Threats

    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

    34 min
  7. Dorota Kozlowska: Empowering Women in Cybersecurity

    FEB 17

    Dorota Kozlowska: Empowering Women in Cybersecurity

    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 Kozlowskahttps://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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    44 min
  8. Keelan Knox: Breaking Things to Building Defenses

    FEB 10

    Keelan Knox: Breaking Things to Building Defenses

    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 Knoxhttps://www.linkedin.com/in/mrkknox/========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie

    28 min
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Ratings & Reviews

4.9
out of 5
18 Ratings

About

The Phillip Wylie Show is a premier cybersecurity podcast and media source for offensive security professionals. Hosted by Phillip Wylie, globally recognized ethical hacking expert, keynote speaker, and co-author of The Pentester Blueprint, the show features elite red team operators, penetration testers, and security leaders sharing real-world tradecraft, advanced tactics, career strategy, and insights on AI-driven cyber threats.

Information

  • Creator
    Phillip Wylie
  • Years Active
    2023 - 2026
  • Episodes
    192
  • Rating
    Clean
  • Copyright
    © Phillip Wylie
  • Show Website
    Phillip Wylie Show

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