Inside Modern Fraud
Easy Prey
Fraud doesn’t always announce itself with obvious warning signs. Quite often, it shows up wrapped inside something that feels routine — a purchase you’ve made before, a link that looks legitimate, a message that arrives at just the wrong moment. Nothing feels suspicious, so your guard stays down. By the time questions start forming, the transaction is already done. My guest today is Iremar Brayner. He’s spent more than 15 years working in fraud prevention and risk management across payments, retail, ride-hailing, fintech, and digital marketplaces. In his role at G2A, he leads fraud...
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Money Laundering
Easy Prey
Organized crime is often imagined as something violent, chaotic, and obvious. But today, it looks far more polished than that. It operates like a multinational business, spread across borders, built on trust networks, specialization, and efficiency rather than brute force. This episode looks at how modern scams, fraud, and money laundering actually work and why they’re so hard to spot before serious damage is done. My guest is Geoff White, an investigative journalist who has spent decades covering organized crime, cybercrime, and financial fraud. His reporting has appeared on BBC News, Sky...
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Critical Infrastructure Risks
Easy Prey
Most cybersecurity conversations focus on stolen data, breached accounts, and attacks that live entirely on screens. This episode looks at a far more consequential threat: what happens when cyberattacks target the physical systems that keep society running. Power, water, transportation, and manufacturing. When those systems fail, the consequences aren’t just digital. They’re immediate, visible, and sometimes dangerous. My guest is Lesley Carhart, Technical Director of Incident Response at Dragos, a cybersecurity firm focused exclusively on protecting critical infrastructure. Lesley...
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Familial Identity Theft
Easy Prey
Identity theft is usually framed as an external threat. Hackers, data breaches, anonymous criminals operating somewhere far away. This episode looks at a much harder reality to face: identity theft that happens inside families, often quietly, over many years, and without immediate detection. The damage isn’t just financial. It reshapes trust, relationships, and a person’s sense of stability long before anyone realizes what’s happening. My guest is Axton Betz-Hamilton, an associate professor of financial counseling and planning whose research focuses on familial and child identity theft....
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Exploiting Trust (Part 2)
Easy Prey
Security failures rarely come from cutting-edge attacks or sophisticated tools. They happen in ordinary moments when someone holds a door, follows an instruction without questioning it, or finds a workaround that makes their day easier. Those small, human decisions are often the real entry points, and they tend to compound over time. This episode picks up the second half of our conversation on exploiting trust with FC Barker, a veteran ethical hacker and physical security expert known for legally breaking into banks, government buildings, and high-security facilities around the world. With...
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Exploiting Trust (Part 1)
Easy Prey
Most security failures don’t start with a dramatic breach or a mysterious hacker sitting in a dark room. They usually start quietly. Someone assumes a system is locked down. Someone trusts that a door shouldn’t open, or that a machine “just works,” or that no one would ever think to look there. Over time, those small assumptions stack up, and that’s where things tend to go wrong. Today’s guest is FC Barker, a renowned ethical hacker, social engineer, and global keynote speaker with more than three decades of experience legally breaking into organizations to expose their blind...
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Surviving a Ransomware Attack
Easy Prey
A ransomware attack doesn’t always announce itself with flashing warnings and locked screens. Sometimes it starts with a quiet system outage, a few unavailable servers, and a sinking realization days later that the threat actors were already inside. This conversation pulls back the curtain on what really happens when an organization believes it’s dealing with routine failures only to discover it’s facing a full-scale cyber extortion event. My guest today is Zachary Lewis, CIO and CISO for a Midwest university, a 40 Under 40 Business Leader, and a former Nonprofit CISO of the Year....
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Why You Fall For Scams
Easy Prey
Why do smart, capable people fall for scams even when the warning signs seem obvious in hindsight? In this episode, Dan Ariely joins us to examine how intuition often leads us in the wrong direction, especially under stress, uncertainty, or emotional pressure. A renowned behavioral economist, longtime professor of psychology and behavioral economics at Duke University, and bestselling author of Predictably Irrational, The Upside of Irrationality, Misbehaving, and Misbelief, Dan has spent decades studying why rational people consistently make choices that don’t serve them. We talk about...
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Mobile Device Threats
Easy Prey
In a world where we’re told to carry our entire lives in our pockets, we’ve reached a strange tipping point where the very devices meant to connect us have become windows into our private lives for those who wish us harm. It’s no longer a matter of looking for the "shady" corners of the internet; today, the threats come from nation-state actors, advanced AI, and even the people we think we’re hiring. We are living in an era where the most sophisticated hackers aren't just trying to break into your phone, they’re trying to move into your business by pretending to be your best...
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Past, Present, and Future of AI agents
Easy Prey
The intersection of AI and cybersecurity is changing faster than anyone expected, and that pace is creating both incredible innovation and brand-new risks we’re only beginning to understand. From deepfake ads that fool even seasoned security professionals to autonomous agents capable of acting on our behalf, the threat landscape looks very different than it did even a year ago. To explore what this evolution means for everyday people and for enterprises trying to keep up, I’m joined by Chris Kirschke, Field CISO at Tuskira and a security leader with more than two decades of experience...
info_outlineAI has brought incredible new capabilities into everyday technology, but it’s also creating security challenges that most people haven’t fully wrapped their heads around yet. As these systems become more capable and more deeply connected to the tools and data we rely on, the risks become harder to predict and much more complicated to manage.
My guest today is Rich Smith, who leads offensive research at MindGard and has spent more than twenty years working on the front lines of cybersecurity. Rich has held leadership roles at organizations like Crash Override, Gemini, Duo Security, Cisco, and Etsy, and he’s spent most of his career trying to understand how real attackers think and where systems break under pressure.
We talk about how AI is changing the way attacks happen, why the old methods of testing security don’t translate well anymore, and what happens when models behave in ways no one expected. Rich also explains why psychology now plays a surprising role in hacking AI systems, where companies are accidentally creating new openings for exploitation, and what everyday users should keep in mind when trusting AI with personal information. It’s a fascinating look behind the curtain at what’s really going on in AI security right now.
Show Notes:
- [01:00] Rich describes getting into hacking as a kid and bypassing his brother’s disk password.
- [03:38] He talks about discovering Linux and teaching himself through early online systems.
- [05:07] Rich explains how offensive security became his career and passion.
- [08:00] Discussion of curiosity, challenge, and the appeal of breaking systems others built.
- [09:45] Rich shares surprising real-world vulnerabilities found in large organizations.
- [11:20] Story about discovering a major security flaw in a banking platform.
- [12:50] Example of a bot attack against an online game that used his own open-source tool.
- [16:26] Common security gaps caused by debugging code and staging environments.
- [17:43] Rich explains how AI has fundamentally changed offensive cybersecurity.
- [19:30] Why binary vulnerability testing no longer applies to generative AI.
- [21:00] The role of statistics and repeated prompts in evaluating AI risk and failure.
- [23:45] Base64 encoding used to bypass filters and trick models.
- [27:07] Differentiating between model safety and full system security.
- [30:41] Risks created when AI models are connected to external tools and infrastructure.
- [32:55] The difficulty of securing Python execution environments used by AI systems.
- [35:56] How social engineering and psychology are becoming new attack surfaces.
- [38:00] Building psychological profiles of models to manipulate behavior.
- [42:14] Ethical considerations and moral questions around AI exploitation.
- [44:05] Rich discusses consumer fears and hype around AI’s future.
- [45:54] Advice on privacy and cautious adoption of emerging technology.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.