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.
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Connect with Jamy Casteel:
LinkedIn: https://www.linkedin.com/in/jamy-casteel
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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.
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Connect with Travis Stein:
LinkedIn: https://www.linkedin.com/in/twstein86/
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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.

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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/

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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.
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Connect with Allie Mellen:
LinkedIn: https://www.linkedin.com/in/hackerxbella/
Allie's book: https://www.amazon.com/dp/1394285574
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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.
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Connect with Eve Maler:
LinkedIn: https://www.linkedin.com/in/evemaler/
Eve's book: https://masteringdigitalidentity.com/
Website: https://www.vennfactory.com/
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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.

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Connect with Sudhanshu Chauhan:

LinkedIn: https://www.linkedin.com/in/sudhanshuchauhan

Website: https://redhuntlabs.com/

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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.
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Connect with Dorota Kozlowska
https://www.linkedin.com/in/dorota-kozlowska/
https://www.woman-in-red.com/
https://www.youtube.com/@womaninredpresents
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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.
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Connect with Keelan Knox
https://www.linkedin.com/in/mrkknox/
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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.

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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/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

X: https://x.com/PhillipWylie

Instagram: https://www.instagram.com/phillipwylie/

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