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.
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August 18, 2026Episode 3241 min
From English Teacher to OSINT Investigator: Lindsey Yagi-Hatake on Breaking Into Cybersecurity
In under a year, Lindsey Yagi-Hatake went from teaching English in a public school classroom to working as a professional OSINT investigator. Her path into cybersecurity did not start with a certification or a computer science degree. It started with survival. Lindsey spent six years as a public school English teacher and holds a master's degree in education administration along with certifications in teaching English as a second language, where she specialized in helping immigrant students adjust to life in a new country. That background in language, culture, and patient instruction shapes how she approaches her work today as an OSINT investigator and privacy manager at Decisive Resources, where she works alongside Mishaal Khan. In this episode, Lindsey shares the full story of how she broke into the field. After becoming a survivor of domestic violence in 2024, she found herself being digitally stalked and geolocated, and when the systems meant to protect her fell short, she taught herself open source intelligence to document what was happening. She talks about the gatekeeping she ran into early on, the moment she spent her last $500 on a DEF CON badge, and how the community at Noob Village and mentors like Mishaal Khan and Chadd Watson changed everything. She also shares hard-won advice for anyone trying to break in today. This is a conversation about grit, community, digital safety advocacy, and what it really takes to get into cybersecurity in today's job market. ========================= Connect with Lindsey Yagi-Hatake: LinkedIn: https://www.linkedin.com/in/lindseyhatake/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie
August 11, 2026Episode 3123 min
AI, Automation, and the Future of Penetration Testing with Herman Zubenko
How is AI changing penetration testing, bug bounty hunting, and offensive security? In this episode of The Phillip Wylie Show, Phillip sits down with Herman Zubenko to explore how artificial intelligence and automation are transforming the way security professionals discover and validate vulnerabilities. Herman shares his unconventional journey from quality assurance and software development into cybersecurity, including how having one of his own accounts compromised led him to investigate the incident with AI and eventually begin using AI for bug bounty research. Phillip and Herman discuss AI-assisted penetration testing, continuous security testing, open and local models, the importance of keeping humans in the loop, and why AI is more likely to enhance penetration testers than replace them. They also discuss how aspiring cybersecurity professionals can use AI to accelerate their learning while still developing the technical fundamentals needed to understand how systems, applications, and vulnerabilities actually work. ========================= Connect with Herman Zubenko: LinkedIn: https://www.linkedin.com/in/herman-zubenko/ Syntetisk Tech Limited website: https://syntetisk.tech/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with @Suzulabs https://suzulabs.com https://x.com/suzulabs https://www.linkedin.com/company/suzu-labs/
August 4, 2026Episode 3027 min
From First-Generation Graduate to DEF CON Speaker: Moo's Cybersecurity Journey
In this episode of The Phillip Wylie Show, Phillip welcomes cybersecurity community member Moo for an inspiring conversation about breaking into cybersecurity, building a career through persistence, and giving back to others along the way. Moo shares his unconventional hacker origin story, from being inspired by *The Matrix* and DEF CON videos as a teenager to eventually speaking at DEF CON and earning his first National Cyber League challenge coin. Along the way, he discusses the value of internships, apprenticeships, mentorship, and exploring different areas of cybersecurity before settling on a career path. Phillip and Moo also discuss the importance of community, continuous learning, and why cybersecurity conferences like DEF CON can be life-changing for newcomers. Whether you're a student, career changer, or experienced security professional, this episode offers practical advice and plenty of encouragement for anyone looking to grow in cybersecurity. ========================= Connect with Moo: LinkedIn: https://www.linkedin.com/in/munirmuhammad/ ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with @SuzuLabs https://suzulabs.com https://x.com/suzulabs https://www.linkedin.com/company/suzu-labs/ ========================= Podcast Music by Syntax976 ========================= LinkedIn: https://www.linkedin.com/in/brandon-prince-27a0ab51/ X: https://x.com/syntax976
July 28, 2026Episode 2927 min
Casey Smith (SubTee): Living Off the Land, Deception Technology, and the Evolution of Offensive Security
In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher, educator, and entrepreneur Casey Smith (SubTee) to discuss his journey into cybersecurity, the evolution of offensive tradecraft, and why deception technology is becoming one of the most effective defensive strategies in today's threat landscape. Casey shares how he transitioned from systems administration into security through application testing and enterprise security projects before becoming widely recognized for his pioneering research into Living Off the Land Binaries (LOLBins). The conversation also explores how Windows security has evolved over the years, the impact of application whitelisting, and why modern defenders should be thinking differently about detection. The discussion wraps up with Casey's latest venture, where he is helping organizations leverage deception technologies while mentoring the next generation of cybersecurity professionals. ========================= Connect with Casey Smith: X: https://x.com/_subTee GitHub: https://github.com/AlloySecureGroup ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with @SuzuLabs https://suzulabs.com https://x.com/suzulabs https://www.linkedin.com/company/suzu-labs/ ========================= Podcast Music by Syntax976 ========================= LinkedIn: https://www.linkedin.com/in/brandon-prince-27a0ab51/ X: https://x.com/syntax976
July 22, 2026Episode 2827 min
The Future of Detection Engineering with Alex Hurtado
Detection engineering doesn't always get the attention it deserves, but it's one of the most important parts of a mature security program. In this episode of The Phillip Wylie Show, Phillip Wylie is joined by detection engineer and content creator Alex Hurtado to discuss why this growing specialty is becoming essential for modern security teams. Alex shares how she went from monitoring enterprise networks early in her career to helping organizations improve their detection capabilities, tune SIEM platforms, and build stronger security operations. She also explains what detection engineering actually involves, why it's much more than writing detection rules, and how AI is changing the way defenders work. Phillip and Alex also discuss the importance of collaboration between offensive and defensive security teams, why custom detections outperform out-of-the-box rules, and how sharing knowledge through content creation benefits both individuals and the cybersecurity community. Whether you're interested in blue team operations, offensive security, or simply exploring different cybersecurity career paths, this episode offers practical advice and a behind-the-scenes look at one of the industry's fastest-growing roles. ========================= Connect with Alex Hurtado:LinkedIn: https://www.linkedin.com/in/hurtadoalexandra/YouTube: https://www.youtube.com/@DetectionDispatch_AlexsVersion========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with @suzulabs https://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/ ========================= Podcast Music by Syntax976 ========================= LinkedIn: https://www.linkedin.com/in/brandon-prince-27a0ab51/ X: https://x.com/syntax976
July 15, 2026Episode 2730 min
From Curiosity to Zero Days: Milton Valencia (wetw0rk) on Exploit Development, Research, and Giving Back
In this episode of The Phillip Wylie Show, Phillip Wylie sits down with offensive security researcher Milton Valencia, better known in the cybersecurity community as wetw0rk. Known for his exploit development research, educational content, and commitment to mentoring others, Milton shares the remarkable journey that took him from a curious student fascinated by hacking to discovering zero-day vulnerabilities and working on elite offensive security teams. Milton discusses overcoming adversity, breaking into the industry without a traditional path, earning certifications like the OSCP, finding his first security roles, and ultimately building a career centered around vulnerability research and exploit development. Along the way, he emphasizes the importance of curiosity, persistence, and helping others succeed. The conversation also explores the future of offensive security, the growing role of AI in reverse engineering, why exploit development remains a valuable specialty, and how aspiring researchers can get started today. If you enjoyed this episode, check out Milton on Season 3 Episode 19 of Simply Offensive @Suzulabs. ========================= Planning to attend Black Hat USA 2026? Use my code PHILLIPWYLIE to receive $200 off a Briefings Pass or $100 off a Business Pass. Register here: https://blackhat.com/us-26/registration.html?_mc=sm_social_phillipwylie Black Hat invited me to attend this year's event and sponsored my conference pass. ========================= Connect with Milton Valencia: LinkedIn: https://www.linkedin.com/in/milton-wetw0rk/ Blog: https://wetw0rk.github.io/ YouTube: https://www.youtube.com/@wetw0rk7 ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= Sponsored by Suzu Labs ========================= All the ways to connect with @Suzulabs https://suzulabs.com https://x.com/suzulabs https://www.linkedin.com/company/suzu-labs/
July 7, 2026Episode 2632 min
From BBS to Mastering Red Team Operations with Mike Ortiz
Mike Ortiz joins Phillip Wylie to discuss his journey from the early BBS and IRC days to the U.S. Marine Corps, global defense contracting, and ultimately becoming a red team operator specializing in adversary emulation and red team engineering. Along the way, Mike shares how his background in networking and enterprise infrastructure helped shape his approach to offensive security and why understanding both attack and defense is critical for today's cybersecurity professionals. The conversation explores the differences between penetration testing and red teaming, why "assume breach" exercises provide greater value for mature organizations, and how modern threat actors operate with patience, stealth, and persistence. Mike also explains how cloud automation has transformed red team infrastructure and introduces Red Stack, his open-source project that simplifies deploying professional red team environments for training and research. ========================= Connect with Mike Ortiz: LinkedIn - https://www.linkedin.com/in/mike-ortiz-redsec Red Stack: https://github.com/BaddKharma/redStack ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie
July 2, 2026Episode 2544 min
From Phone Phreaking to Cloud Security: Jason Faulhefer's Cyber Journey
In this episode, Jason Faulhefer shares his hacker origin story, discusses his innovative threat intelligence platform Threat Spire, and explores the evolution of cybersecurity from early phone hacking to modern cloud and OT security. ========================= Connect with Jason Faulhefer: LinkedIn - https://linkedin.com/in/jasonfaulhefer X - https://x.com/jasonfaulhefer ========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylie X: https://x.com/PhillipWylie Instagram: https://www.instagram.com/phillipwylie ========================= I'm excited to share that I'll be attending Black Hat USA 2026 this August in Las Vegas. Every year, Black Hat brings together some of the best security researchers, practitioners, vendors, and industry leaders. It's one of my favorite events because there's always something new to learn, whether it's cutting-edge research, emerging attack techniques, AI security, offensive security, or conversations with people pushing our industry forward. I'm looking forward to: - Attending Briefings and learning from leading researchers Catching up with friends and colleagues across the security community - Meeting new people who are passionate about cybersecurity - Seeing the latest innovations from vendors and startups If you've been considering attending, now is a great time. Use my code PHILLIPWYLIE to receive $200 Off a Briefings Pass or $100 Off a Business Pass. Register here: https://blackhat.com/us-26/registration.html?_mc=sm_social_phillipwylie Thanks to @BlackHat for inviting me to attend this year's event and sponsoring my pass. I hope to see you there!
June 23, 2026Episode 2458 min
Ridge Security in the Real World: An Offensive Security Practitioner's Perspective
## How AI-Powered Penetration Testing Is Transforming Security Validation with Andy Simpson**Sponsored by Ridge Security**In this sponsored episode of The Phillip Wylie Show, Phillip Wylie welcomes Andy Simpson, founder of Cipher Security, for an in-depth discussion about the future of penetration testing, continuous security validation, API security, and the growing role of AI in offensive security.What makes this conversation unique is that Andy is not a Ridge Security employee. As a cybersecurity consultant and penetration testing practitioner, he evaluated multiple automated security testing platforms before selecting Ridge Security to help scale and enhance his team's testing capabilities.Drawing on decades of experience in IT, infrastructure, executive leadership, and offensive security, Andy shares his journey from working at IBM to building a successful offensive security consultancy serving organizations throughout Australia and New Zealand.The conversation explores the challenges facing modern security teams, including expanding attack surfaces, API security risks, infostealer-driven attacks, limited security resources, and the need to continuously validate security controls. Andy also demonstrates how automation and AI-driven testing are changing the way organizations identify and validate risk.## Topics Covered* Andy Simpson's cybersecurity origin story* From IBM engineer to offensive security consultant* The evolution of penetration testing* Common shortcomings in traditional API assessments* Continuous Threat Exposure Management (CTEM)* Vulnerability validation versus vulnerability identification* Automated penetration testing at scale* Attack surface management## Key Takeaways* Annual penetration testing is often insufficient for today's threat landscape.* Organizations need continuous validation of their attack surface and security controls.* API security remains one of the most overlooked areas of cybersecurity.* Security teams must focus on validating risk rather than simply identifying vulnerabilities.* Automation helps security teams scale without sacrificing visibility.* Generative AI is enabling deeper testing of business logic and application workflows.* Human expertise remains critical, but AI-powered testing is becoming an important force multiplier.* Attackers are increasingly leveraging stolen credentials and authenticated access paths, making continuous testing more important than ever.Connect with Andy Simpson:Andy's LinkedIn: https://www.linkedin.com/in/andy-simpson-nz/Cipher Security website: https://ciphersecurity.co.nz/## Episode SponsorThis episode is sponsored by Ridge Security.Connect with Ridge Security:Ridge Security website: https://ridgesecurity.aiGet a free RidgeBot Demo: https://ridgesecurity.ai/demo-request/ Ridge Security LinkedIn: https://www.linkedin.com/company/ridge-security/posts/?feedView=allRidge Security provides automated penetration testing and security validation solutions that help organizations continuously identify, validate, and prioritize security risks across networks, web applications, APIs, and cloud environments. During this episode, Andy shares his firsthand experience using Ridge Security's platform as part of his offensive security practice. ## Connect with Andy SimpsonConnect with Andy on LinkedIn to learn more about offensive security, API testing, threat exposure management, and the future of AI-powered security testing.## Listen, Subscribe, and ShareEnjoyed the episode? Subscribe to The Phillip Wylie Show, leave a review, and share this episode with your network to help others learn about the future of penetration testing and security validation.#ThePhillipWylieShow #Cybersecurity #PenTesting #OffensiveSecurity #APISecurity #AI #ArtificialIntelligence #CTEM #ThreatExposureManagement #RidgeSecurity #SecurityTesting #EthicalHacking #CyberDefense #InfoSec #CyberRisk
June 17, 2026Episode 2330 min
From Hacker to Medical Device Pentester: Sean Satterlee on Securing Life-Critical Technology
What happens when hacking moves beyond computers and into devices that can keep people alive? In this episode of The Phillip Wylie Show, Phillip Wylie welcomes Sean Satterlee to discuss the rapidly growing field of medical device security. Sean explains how security researchers evaluate connected healthcare technology, the skills needed to transition into hardware hacking, and why traditional pentesting knowledge is still incredibly valuable in the world of embedded systems. From Wireshark and wireless protocols to JTAG, UART, and hardware analysis, this conversation provides a practical roadmap for cybersecurity professionals interested in expanding their offensive security skillset. ========================= Connect with Sean Satterlee: LinkedIn: https://www.linkedin.com/in/seansatterlee/ ========================= 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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