Elder Exploitation
Easy Prey
Aging parents often rely on the people closest to them for help, but what happens when that help becomes a way to take control? For Charles Wallace, the warning signs started small. His mother’s fridge was suddenly overfilled. A caregiver refused to provide receipts. Spending patterns began to shift in ways that did not make sense. At the time, each concern could be explained away. Looking back, they were part of something much larger. Charles spent 15 years in banking and finance, and after his mother’s death, he used that experience to reconstruct more than 3,000 transactions. What he...
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Art Heists
Easy Prey
The world of art theft looks glamorous in the movies, but the reality is far more complicated. From multi-million dollar forgery schemes to undercover FBI operations recovering stolen national treasures, art crime is a global industry hiding in plain sight. This conversation digs into how these crimes actually play out and why the people who pull them off often end up stuck with the very pieces they thought would make them rich. My guest today is Robert Wittman, a former FBI special agent and the founder of the FBI’s Art Crime Team. Over a 20-year career, he worked undercover in more...
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The Power of Prediction
Easy Prey
We make predictions all the time including about the weather, about traffic, about what someone is going to say next. It feels natural, even rational. But when algorithms start making predictions about us, whether we'll repay a loan, reoffend after prison, or respond to a medical treatment, something fundamental shifts. The forecast stops being a guess and starts becoming a verdict. My guest today is Carissa Veliz, a philosopher and associate professor at the University of Oxford, where she also researches at the Oxford Internet Institute. Her work focuses on the ethics of technology, privacy,...
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Privacy vs Reality
Easy Prey
Online security advice often sounds simple until you actually try to follow it. Between password managers, privacy settings, and data brokers, protecting yourself can start to feel like a full-time job. That gap between what sounds easy and what’s actually realistic is where a lot of people get stuck. My guest today is Yael Grauer, a freelance investigative technology reporter who covers privacy, security, digital freedom, hacking, and mass surveillance. She also works as a program manager of cybersecurity research at Consumer Reports, where she manages Security Planner, a free resource that...
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Wired to Trust
Easy Prey
It’s easy to think scams only work when someone misses something obvious. In reality, most of them don’t look obvious at the start. They show up as normal situations with just enough friction to notice, but not enough to stop. That small gap is where people tend to move forward instead of stepping back. My guest today is Tali Sharot, a cognitive neuroscientist who studies how we form beliefs and make decisions. She’s known for her research on the neural basis of human optimism, and her work has been published in leading journals. In her books, The Optimism Bias and The Science of...
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Intimate Partner Fraud
Easy Prey
Most scams leave a digital trail. A fake email, a spoofed number, a fraudulent website. You can trace them, report them, sometimes even reverse them. But what happens when the scam has no digital trail at all, because it isn't happening on a screen? What happens when the con is standing right in front of you, making you laugh, meeting your friends, and planning a future with you? My guest today is Tracy Hall. She's an author, keynote speaker, and senior marketing executive with over 25 years at some of the world's most recognizable tech companies including eBay, Virgin, GoDaddy, and...
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Identity without Passwords
Easy Prey
Every day, employees at hotels, restaurants, and resorts across the country are doing exactly what they were hired to do: being warm, responsive, and eager to help. It's what makes hospitality work. It's also what makes hospitality one of the most targeted industries in cybersecurity. When your entire workforce is trained to say yes, teaching them to be suspicious is an uphill battle. The smarter solution might be to take the target off their backs entirely. Jasson Casey is the co-founder and CEO of Beyond Identity, a company built around one idea: making identity-based attacks impossible....
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When Cybercrime Gets Personal
Easy Prey
Most security breaches don't begin with sophisticated code or elaborate technical exploits. They begin with a phone call, a convincing email, or someone at a help desk who just wanted to be helpful. The human layer is often the weakest link, and the criminals who understand that are the ones causing the most damage. My guest today is May Chen-Contino. She's the CEO of Unit 221B, a threat disruption company that delivers actionable intelligence to enterprises, law enforcement, and government agencies. Her background spans cybersecurity, fintech, and SaaS leadership at companies like PayPal and...
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Stopping Phone Scams
Easy Prey
Phone scams get dismissed as background noise or just annoying interruptions and unknown numbers with robotic voices we learn to ignore. But behind that noise is an industry built on psychology, automation, and staggering profitability. My guest today is Alex Quilici. He’s an engineer, entrepreneur, and the CEO of YouMail, a company focused on protecting consumers and businesses from unwanted and fraudulent calls. Alex has spent years analyzing how robocalls and scam campaigns are designed, how they evolve, and why they continue to work despite better technology and increased awareness. What...
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Stolen Identity - Stolen Peace
Easy Prey
Identity theft gets talked about a lot, but usually in the abstract: freeze your credit, watch your statements, don't click suspicious links. What doesn't get talked about nearly enough is what it actually feels like when someone isn't just using your card number, but is actively living as you. My guest today is Brooklyn Lyons. She's 25, recently married, and by her own admission, had no particular expertise in fraud or cybersecurity before October of 2024. That changed when her car window was smashed in a parking lot, and her work bag, laptop, wallet, driver's license, and everything...
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.