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Phillip Wylie Show: Daily Summaries Delivered
by Phillip Wylie
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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- 4 days ago27 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/_subTeeGitHub: https://github.com/AlloySecureGroup========================= 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
- 1 weeks ago27 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
- 2 weeks ago30 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_phillipwylieBlack 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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie========================= Sponsored by Suzu Labs=========================All the ways to connect with @Suzulabshttps://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/
- 3 weeks ago32 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-redsecRed Stack: https://github.com/BaddKharma/redStack========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie
- Jul 2, 202644 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/jasonfaulheferX - https://x.com/jasonfaulhefer========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: 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 researchersCatching up with friends and colleagues across the security community- Meeting new people who are passionate about cybersecurity- Seeing the latest innovations from vendors and startupsIf 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_phillipwylieThanks to @BlackHat for inviting me to attend this year's event and sponsoring my pass.I hope to see you there!
- Jun 23, 202658 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
- Jun 17, 202630 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/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie
- Jun 9, 202623 min
From Mischief to Mastery: Christian Gonzalez's Cybersecurity Journey
In this episode of The Phillip Wylie Show, Phillip sits down with longtime friend, former student, and offensive security professional Christian Gonzalez. Christian shares his journey from curious teenager and network engineer to penetration tester, mobile application security specialist, and AI security researcher. The conversation explores career growth, certifications, AI security, and how aspiring pentesters can stay relevant in an increasingly competitive cybersecurity landscape.========================= Connect with Christian Gonzalez:LinkedIn: https://www.linkedin.com/in/christian-g-672104160/Educational AI Pentesting Lab: https://www.aipwn.me/========================= Connect with your host, Phillip Wylie: LinkedIn: https://linkedin.com/in/phillipwylieX: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie
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About Phillip Wylie Show
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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