73 episodes

Join Phillip Wylie Show host Phillip Wylie as he and his guests discuss the intriguing and ever-expanding field of cybersecurity, including topics from the offensive security side to the defensive and response sides of cybersecurity. Frequent offensive security topics include pentesting, red teaming, ethical hacking, security research, and bug bounties. Guests share their origin stories, tips, and career advice. Phillip and his guests discuss content creation and personal branding in this podcast. If you enjoyed Phillip's previous podcast, The Hacker Factory, you will love this!

Phillip Wylie Show Phillip Wylie

    • Technology
    • 5.0 • 12 Ratings

Join Phillip Wylie Show host Phillip Wylie as he and his guests discuss the intriguing and ever-expanding field of cybersecurity, including topics from the offensive security side to the defensive and response sides of cybersecurity. Frequent offensive security topics include pentesting, red teaming, ethical hacking, security research, and bug bounties. Guests share their origin stories, tips, and career advice. Phillip and his guests discuss content creation and personal branding in this podcast. If you enjoyed Phillip's previous podcast, The Hacker Factory, you will love this!

    Cathy Ullman: The Power of Active Defense

    Cathy Ullman: The Power of Active Defense

    About the Guest:

    Cathy Ullman, known in the cybersecurity community as Investigator Chick, boasts an impressive 24-year tenure at the University of Buffalo where her expertise spans across digital forensics and incident response. She has not only made a mark with her significant work in tech support but also holds a leadership position in organizing significant conference events such as summer camp. A celebrated author, Ullman recently published a thought-provoking book that delves into the intersection of offensive and defensive cybersecurity strategies.

    Episode Summary:

    In this episode of the Phillip Wylie show, listeners are treated to an intimate conversation with cybersecurity expert Cathy Ullman. The talk traverses Ullman's storied path which veers from a unique childhood surrounded by pioneering computing to her two-decade-plus stint in university cyber security. Along the way, Ullman offers a peek into the heart of her recent book, which urges a mindset shift in cybersecurity defense by taking cues from offensive tactics.

    Ullman reflects on her early days in tech support, leading to her current specialization in digital forensics and incident response at the University of Buffalo. She discusses the value and rigorous nature of certifications such as the IAsis and the doors they've opened within her field. The conversation turns to Ullman's enlightening journey into the offensive side of cybersecurity, captured in her new book "The Active Defender." Ullman makes a compelling case for why understanding offensive strategies can fortify defense mechanisms within the cybersecurity realm.

    Key Takeaways:

    Cathy Ullman's Emergence: From a childhood surrounded by computing, Cathy's journey is emblematic of the organic evolution into the cybersecurity niche.

    Higher Education in Cybersecurity: Ullman underscores the benefits and stability offered by her long-standing role at the University of Buffalo and the profound learning and growth it has facilitated.

    Digital Forensics Certification: Cathy shares insights into the invaluable expertise and depth gained from the digital forensics and incident response training with IAsis.

    Cybersecurity Community Engagement: The significance of attending and participating in events like B sides for professional development and networking is emphasized.

    Understanding Offensive Security: Ullman explores the perspective that comprehending offensive techniques enhances defensive strategies, a central theme in her latest book.

    Notable Quotes:

    "And I took SANS classes on forensics before I had the IACIS background, and it did not go well."

    "Understanding how offensive security folks think, because if you understand what they do and how they think, then you can be better as a defender in terms of your own defenses."

    "I've been there 24 years, and I've had the opportunity to kind of grow into different spaces within that without having to jump ship."

    "It was a matrix moment, you know, the blue pill, red pill thing, where I suddenly realized, hey, there's this whole other world that I was missing out on."

    "Everybody wants to share all the cool things with you. The excitement is palpable when you go to these conferences."


    Cathys Twitter: @investigatorchic

    Cathy's LinkedIn: https://www.linkedin.com/in/catherine-ullman-26a9406/

    Cathy's book: The Active Defender: Immersion in the Offensive Security Mindset https://www.wiley.com/en-us/The+Active+Defender%3A+Immersion+in+the+Offensive+Security+Mindset-p-9781119895213

    • 33 min
    Andy Liverman Anderson: Scaling Cybersecurity Functions with AI

    Andy Liverman Anderson: Scaling Cybersecurity Functions with AI

    About the Guest:

    Andy Liverman Anderson is a seasoned professional with a diverse background spanning real estate, Wall Street, and cybersecurity. With nearly a decade dedicated to the field of cybersecurity, Andy brings a wealth of experience and knowledge to the industry. As a history major, he leverages his unique perspective to analyze the intricacies of cybersecurity's geopolitical landscape. Notably, Andy has been pivotal in the development of moving target defense strategies and has pioneered the use of machine learning to estimate cyber risk in the insurance domain. Currently, he serves as a VP of Sales at Uno AI, a company at the forefront of incorporating AI into cybersecurity efforts.

    Episode Summary:

    This episode of The Phillip Wylie Show delves into the rapidly evolving landscape of cybersecurity, focusing on the integration of automation and AI technologies. Host Phillip Wylie is joined by Andy Liverman Anderson from Uno AI to explore the ways these advancements are transforming the industry. Fascinated by the seismic shift caused by AI tools like Chat GPT, they discuss the implications for cybersecurity professionals, who like superheroes, each have their own origin story.

    The conversation begins by highlighting the role of automation in cybersecurity, referencing Jeff Foley's mass reconnaissance script, and moves on to unpack Andy's journey from real estate and Wall Street into the complex world of cybersecurity. The second summary paragraph touches on the significant role AI plays in vulnerability management, acting as a force multiplier for security practitioners, and the potential for Uno AI's copilots to scale and enhance the capabilities of cybersecurity teams. As the episode unfolds, it becomes clear that the integration of AI into cybersecurity is not just a possibility, it's a reality unfolding before us.

    Key Takeaways:

    Automation and AI are revolutionizing cybersecurity, taking over repetitive and tedious tasks to free up professionals for more complex work.

    Andy Liverman Anderson's history in both traditional tech and cybersecurity provides a unique perspective on the use of AI in cybersecurity.

    Cyber insurance and understanding post-attack scenarios are critical components in managing cyber risk effectively.

    Uno AI's cyber AI copilot assists security professionals by streamlining the process of vulnerability management and producing actionable insights.

    As AI democratizes technology, it may lower barriers to entry in cybersecurity and generate better, more creative jobs.

    Notable Quotes:

    "It's the land of broken toys. You get to look at all these different things."

    "Every organization should have cyber insurance. I'm not selling insurance anymore, but I think you're crazy as an organization, even a very small business, it's surprisingly inexpensive."

    "What AI is going to do because the very narrow skills that you had are no longer so scarce."

    "A bot never gets tired, is always happy to answer them, and as long as they're providing accurate answers."

    "When you've seen sort of a democratization of core technologies, that's just the explosive impact it's had across the world."





    • 33 min
    Be Fearless Online: In Browser Malicious File Detection Part 2

    Be Fearless Online: In Browser Malicious File Detection Part 2

    About the Guest:

    Dakshitaa Babu is a Software Engineer at SquareX, where she is engaged in data engineering and analytics.

    She is also the pen behind the engineering blogs written on SquareX's infrastructure and security research. After completing her Bachelor's degree at the National University of Singapore, Dakshitaa joined SquareX, marking her foray into the cybersecurity industry. While new to the field, her enthusiasm for discovering and understanding new concepts has quickly established her as a committed contributor to the evolving sector. Her interests are in Browser Security and consumer education.

    Episode Summary:

    In this captivating episode of The Phillip Wylie Show, cybersecurity enthusiasts witnessed a deep dive into the cutting-edge realm of in-browser malicious file detection with Dakshitaa Babu. Dakshitaa, showcasing her prowess in the industry, illustrates sophisticated features of her company's flagship cybersecurity product designed to enhance online safety.

    Dakshitaa demonstrates the product's ability to detect malicious macros within files, emphasizing the significance of privacy in their detection methods which occur directly within the browser environment. Focusing primarily on Gmail due to its widespread use, she articulates how the product can reveal hidden dangers within office documents and macros. The episode highlights not only the detection of conventional threats but also uncovers tactics like file renaming, VBA purging, and old file format analysis to pinpoint potentially harmful activity.

    The conversation shifts towards the efficiency and privacy advantages of in-browser detection. Dakshitaa explains how this approach offers immediate and private threat recognition compared to traditional methods. She confidently positions her company's product as a vital layer of defense, complementing existing antivirus solutions and empowering users with immediate insights into file safety before downloads occur.

    Key Takeaways:

    In-browser malicious file detection technology offers advanced privacy and fast analysis by scanning files directly within the email client.

    Dakshitaa demoed the tech's proficiency in detecting renamed files, large file components, and outdated file formats—all indicative of potential malware.

    The product integrates seamlessly with Gmail, providing users with immediate warnings and detailed insights into file contents without downloads.

    Unique detection methods allow for identifying suspicious activities such as VBA purging, which can bypass some antivirus solutions.

    The browser extension is free and compatible with all chromium-based browsers, encouraging user adoption for an added layer of cybersecurity.

    Notable Quotes:

    "We are going deeper than what surface level checks do in Gmail, for instance." -Dakshitaa Babu

    "We have no idea why you're still using it in 2024." -Dakshitaa Babu

    "We are trying to create a product that has never been there before that is truly important for every user." -Dakshitaa Babu

    "We can't always take our own sweet time to scan through every single file thoroughly before letting the user use it." -Dakshitaa Babu

    "We want to make sure that before you give the file a chance to even penetrate to your local device or to your network… we want to be there first and give you a first line of defense." -Dakshitaa Babu


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    • 34 min
    Michael Jenks: Lessons from a Former DoD Professional

    Michael Jenks: Lessons from a Former DoD Professional

    About the Guest:

    Michael Jenks, commonly referred to as "Jenks," is an esteemed figure with an extensive background in the Department of Defense (DoD). With a penchant for cybersecurity and a wealth of experience in cyber warfare, Jenks offers a valuable skill set that has been honed in high-stakes environments where precision and accuracy are paramount. Having started his journey in computer science, he quickly developed a fascination with digital code and its impact. Transitioning from dial-up ISPs to L-3 Communications, where he gained clearance for classified work, Jenks eventually founded his own defense contracting company specializing in offensive and defensive cyber operations.

    Episode Summary:

    In this riveting episode of the Phillip Wylie Show, host Phillip examines the intersection of cybersecurity and defense backgrounds through his conversation with Michael Jenks from Interpris. The dynamic dialogue delves into how professionals from critical sectors, such as the Department of Defense, bring innovative solutions and meaningful perspectives to the cybersecurity industry.

    Jenks shares his 'origin story,' which follows a trajectory starting from gaming and IRC administration, leading to a computer science degree and an impressive tenure at various defense-related roles. His story highlights a critical insight: that the best cybersecurity defenses are often forged in the crucible of real-world operations where the cost of failure is immense.

    Central to the conversation, Jenks unravels the methodology behind Interpris—a platform designed to contextualize and elevate existing cybersecurity tools through continuous threat exposure management. Leveraging a thorough understanding of threat profiles, Interpris aims to help organizations prioritize potential risks based on industry, operations, and data sensitivity. The platform's philosophy is clear—fortify defenses by optimizing tools that organizations already possess, using informed strategies and continuous monitoring to proactively counter advanced cyber threats.

    Key Takeaways:

    Cyber professionals with DoD experience bring invaluable expertise to cybersecurity solutions.

    Interpris focuses on improving an organization's security posture by providing context and strengthening existing tools.

    Assume breach approach and implementing best practices are essential for a robust security posture.

    Insider threats are as significant as external threat actors, making holistic security measures necessary.

    The emergence of AI in both offensive and defensive cybersecurity tools is rapidly changing the landscape.

    Notable Quotes:

    "I mean, man, if you have it, background, a clearance, man, there are just a ton of jobs." -Michael Jenks

    "From just the digital realm. Gamer growing up. Cut my teeth on hacking back in the day." -Michael Jenks

    "You already have enough tools, right. It's really just that optimized configuration, that prioritization, that customization." -Michael Jenks

    "It's my job to defend this environment. I have no idea where we're protected, where we're not." -Michael Jenks

    "What we're doing is weaving together all of these products, from EDR, from network sensing, to firewall, to your ESM." Michael Jenks






    • 42 min
    Be Fearless Online: In Browser Malicious File Detection Part 1

    Be Fearless Online: In Browser Malicious File Detection Part 1

    About the Guest:

    Jeswin Mathai is the Chief Architect at SquareX. He leads the team responsible for designing and implementing the Infrastructure. Prior to joining SquareX, He was working as the chief architect at INE. He has published his work at DEFCON China, RootCon, Blackhat Arsenal, and Demo Labs (DEFCON). He has also been a co-trainer in-classroom training conducted at Black Hat Asia, HITB, RootCon, and OWASP NZ Day. He has a Bachelor's degree from IIIT Bhubaneswar. He was the team lead at InfoSec Society IIIT Bhubaneswar in association with CDAC and ISEA, which performed security auditing of government portals and conducted awareness workshops for government institutions. His area of interest includes Cloud Security, Container Security, and Web Application Security.

    Episode Summary:

    In this riveting episode of the "Philip Wylie Show," listeners are invited to explore the intricate world of cybersecurity with Jeswin Mathai, who returns to discuss the innovative features of Squarex. Designed to bolster online safety, Squarex addresses the challenges individuals face with malicious files, particularly through email and other online communication platforms.

    Jeswin demonstrates Squarex's ground-breaking in-browser malicious file detection capability against the backdrop of increasing macro-based cyber threats. These threats often exploit macros within documents to compromise systems, a technique that has persisted in popularity among cybercriminals. Jeswin also touches upon the limitations of traditional antivirus solutions and email client security in detecting such risks.

    Key Takeaways:

    Squarex's new feature conducts an in-browser analysis of files to promptly detect malicious content, enhancing email client security.

    Traditional antivirus programs and email clients often fail to adequately detect or block macros, a common vector for cyber attacks.

    Attackers can exploit file type mismatches and employ social engineering tactics to deliver malicious payloads through seemingly benign document files.

    Jeswin unveils techniques such as "VBA Stomping" and "VBA Purging" that attackers use to bypass antivirus detection.

    Squarex offers solutions to safely convert potential macro-threats into clean or PDF versions within the browser, providing a privacy-centric approach to cybersecurity.

    Notable Quotes:

    "Anytime you receive a malicious attachment…we are going to do in-browser file analysis." - Jeswin Mathai

    "It's kind of interesting because, like going through the OSCP course, one of the payloads they were mentioning during that time, this was back 2012, 2013, was using macros in the payloads." - Phillip Wylie

    "Gmail, when it comes to webmail client, has the most amount of market share…72% is just Gmail." - Jeswin Mathai

    "So the way mail clients work is, let's say here, we'll consider the example of Gmail…" - Jeswin Mathai

    "The sad part about COVID was a lot of things happened that we are not aware of because the sad event of COVID, the deaths…a lot of other attention or other issues were not given that much amount of attention and they never came to the light of the public." - Jeswin Mathai


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    • 51 min
    Chris Glanden, Kevin Pentecost, & Jason Popillion: Welcome to The Circus

    Chris Glanden, Kevin Pentecost, & Jason Popillion: Welcome to The Circus

    About the Guests:

    Kevin Pentecost and Jason Papillon are the dynamic duo behind the engaging podcast Cyber Distortion. They share a strong history of creating content that delves deep into the cybersecurity world, aiming to educate and inform a wide audience about offensive and defensive strategies within the industry. Kevin brings in his expertise in graphic design, while Jason focuses on the content structure and delivery, making them a well-rounded team.

    Chris Glanden is the voice behind the Barcode podcast and the newly introduced webcast, Risk Radar. With previous experience in film, Chris steers his podcast to explore the impacts of AI on cybersecurity, aligning with his efforts to create a documentary on the weaponization of AI systems. He recently made strides into entrepreneurship with his company, Barcode Security.

    In this episode of the Phillip Wylie Show, we're treated to a rare gathering of cybersecurity enthusiasts who have built a reputation for their captivating content creation. This episode stands out as the first to feature multiple guests, offering a unique blend of perspectives on professional hacking, content creation, and AI's role in cybersecurity.

    Episode Summary:

    The episode kicks off with a recount of the Lone Star Cyber Circus—a collaboration event that brought together local talent from Dallas and introduced thought-provoking discussions on the ever-evolving Dallas hacker scene and AI's intersection with cybersecurity. The conversation pivots to the art and influence of content creation, as the guests delineate pathways for individuals to kickstart or amplify their cybersecurity careers through effective branding and exposure.

    As the dialogue unfolds, it touches upon the individual journeys and collaborative ventures of the guests. Kevin and Jason of Cyber Distortion detail their foray into podcasting, aiming to disseminate cybersecurity knowledge at scale. Chris shares his foray into documentary filmmaking, aiming to shed light on the dark potential of AI if left unchecked. Together, their experiences coalesce into a shared vision that culminates in the announcement of the Cyber Circus Network (CCN)—a unifying initiative set to propel the cybersecurity conversation into new heights.

    Key Takeaways:

    The synergistic collaboration of Kevin and Jason provides insights into the world of cybersecurity through their high-production podcast, Cyber Distortion.
    Chris Glanden's Barcode podcast and his upcoming documentary on AI highlight the industry's pertinent issues and emerging threats.
    Content creation in cybersecurity is an avenue ripe for exploration, presenting opportunities for education, networking, and career growth.
    The newly formed Cyber Circus Network signals a collective move toward amplifying cybersecurity awareness and fostering community engagement through various events and content mediums.
    The upcoming episodes and events under CCN are gearing up to provide value-driven, diverse content for the cybersecurity community.

    Notable Quotes:

    "We want to surround ourselves with as many people as possible that can add value to the area that we're working in." — Jason Papillon

    "I always have fun meeting with you guys and talking shop." — Jason Popillion
    "I'm excited about what we all do individually as well, and how that adds value." — Jason Papillon
    "I think our values align as well. At the end of the day, we all want to help each other." — Chris Glanden


    Kevin Pentecost & Jason Popillion: Cyber Distortion Podcast


    Chris Glanden: Barcode Podcast


    • 1 hr 1 min

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