Phillip Wylie Show | Cybersecurity & Pentesting Podcast

## 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

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

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/phillipwylie⁠X: https://x.com/PhillipWylieInstagram: https://www.instagram.com/phillipwylie/=========================Chapters00:00 Introduction and Guest Background01:32 Travis Weathers' Hacker Origin Story05:31 Transitioning to Business Ownership09:33 Training and Course Offerings13:01 Advice for Aspiring Pen Testers18:17 Understanding Red Teaming vs. Pen Testing21:50 Career Advancement Strategies24:40 The Role of AI in Cybersecurity27:31 Teleport Ad30:09 Phillip Wylie Show Outro

SummaryIn 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/shubhamkhichi⁠https://www.cyberagi.ai/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Chapters00:00 Introduction and Background01:55 Shubham's Hacker Origin Story04:39 The Importance of Human Element in Cybersecurity07:20 Excalibur: A Human-Centric Security Platform10:02 Building Intuitive Security Tools11:45 The Role of Experience in Cybersecurity Startups14:27 Understanding Red Teaming vs. Pen Testing19:26 Inversion Theory in Threat Modeling24:00 AI and Privacy in Cybersecurity29:17 AI's Role in Augmenting Human Work33:19 Advice for Aspiring Pen Testers34:55 Closing Thoughts and Future Outlook

SummaryIn 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.TakeawaysChris Glanden's journey into cybersecurity began after high school.He transitioned from IT to cybersecurity in 2011.Chris started his podcast during the pandemic in 2020.He has produced two documentaries focusing on cybersecurity themes.The Lone Star Cyber Circus is a community event Chris is passionate about.Public speaking was a challenge for Chris, but he has embraced it.Chris aims to create a conference for content creators in cybersecurity.He encourages aspiring podcasters to start with a clear purpose.Feedback from listeners motivates podcasters to continue their work.Community engagement is vital for personal and professional growth.Connect with Chris:https://www.linkedin.com/in/chrisglanden/https://pr0ph-1t.com/https://www.barcodesecurity.com/