Hacking AI
Easy Prey
AI 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,...
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The Ransomware War
Easy Prey
Ransomware isn’t a lone hacker in a hoodie. It’s an entire criminal industry complete with developers, brokers, and money launderers working together like a dark tech startup. And while these groups constantly evolve, so do the tools and partnerships aimed at stopping them before they strike. My guest today is Cynthia Kaiser, former Deputy Assistant Director of the FBI’s Cyber Division and now the Head of the Ransomware Research Center at Halcyon. After two decades investigating global cyber threats and briefing top government leaders, she’s now focused on prevention and building...
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Opportunistic Crimes
Easy Prey
Criminals are always adapting. Whether it’s copper wiring stripped from job sites or porch pirates grabbing deliveries in broad daylight, they keep finding new ways to take what isn’t theirs. But maybe prevention isn’t about harsher punishment or more cameras. Maybe it’s about smarter design and understanding what drives people to steal in the first place. My guest today is Dr. Ben Stickle, a professor of criminal justice at Middle Tennessee State University and one of the country’s top researchers on property crime. Before entering academia, he worked in law enforcement, which gives...
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Post Scam Guidebook
Easy Prey
Fraud usually gets talked about in numbers like how much money was stolen, how many people were affected, how many cases got filed. But behind every one of those numbers is a person who’s been blindsided, manipulated, or left trying to rebuild trust in others and in themselves. This episode shifts the focus back to those human stories and the fight to protect them. My guest, Freddie Massimi, has spent more than a decade helping scam victims find both financial and emotional recovery, bringing empathy and understanding to a field that too often feels cold and procedural. As a certified...
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Can You Trust Anything Online
Easy Prey
You think you’d never fall for a scam until you meet someone like Kitboga. He’s a software engineer who’s turned his curiosity about online fraud into a full-time mission to outsmart scammers and protect the people they target. His YouTube channel, The Kitboga Show, has millions of followers and nearly a billion views, thanks to his mix of humor, empathy, and clever ways of exposing how scams really work. In our conversation, Kit opens up about how this all started, what it’s really like to spend hours pretending to be a scam victim, and how organized crime has turned fraud into a...
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Real Time Fraud Detection
Easy Prey
Everywhere you turn, someone’s trying to fake something like an image, a voice, or even an entire identity. With AI tools now in almost anyone’s hands, it takes minutes, not days, to create a convincing fake. That’s changed the game for both sides. The fraudsters have new weapons, and the rest of us are scrambling to keep up. The real question now isn’t just how to stop scams, but how to know who or what to trust online. My guest today, Bala Kumar, spends his days on the front lines of that battle. He’s the Chief Product and Technology Officer at Jumio, a company working to make...
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Child Predator Tactics
Easy Prey
Kids spend more time online than ever, and for the most part it feels normal. They’re gaming, watching videos, and chatting with friends. But hidden in those same spaces are adults who know how to pose as kids, build trust, and push conversations into dangerous territory. Parents might think it couldn’t happen to their child, yet detectives see how quickly an “innocent” interaction can turn into grooming or extortion. That’s the world Detective Seth Cockerham works in every day. He’s been in law enforcement in Texas for close to a decade, and the last few years have been dedicated...
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Identity Trafficking
Easy Prey
Some people are willing to hand over their identities for cash, while organized fraudsters are lining up to buy them. What used to be a matter of stolen credit cards has turned into a global marketplace where personal details fuel large-scale fraud. Now with AI, automation, and deepfakes making impersonation easier than ever, it’s becoming much more difficult to protect identities. To understand how we got here and what can be done, I spoke with Ofer Friedman, Chief Business Development Officer at AU10TIX. Ofer has spent more than 15 years in the identity verification and compliance...
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Technology, Trust & Time
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Technology is moving faster than our ability to process its impact, forcing us to question trust, motivation, and the value of our time. Few people have had a closer view of those shifts than Esther Dyson. With a background in economics from Harvard, Esther built a career as a journalist, author, commentator, investor, and philanthropist, with a unique ability to spot patterns across industries and challenge assumptions before they become mainstream. She is the executive founder of Wellville, a ten-year nonprofit project dedicated to improving equitable well-being in communities across the...
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The Global Scam Battle
Easy Prey
Cybercrime continues to evolve in sophistication and scale, with attackers running their operations much like businesses. From ransomware gangs with customer support desks to AI-generated phishing campaigns that erase traditional red flags, scams are becoming harder to detect and stop. In this episode, David Bittner, host of the CyberWire Daily Podcast, shares his perspective on the changing landscape of fraud and cyberattacks. Drawing on his background in media, theater, and podcasting, as well as years of reporting on security issues, he explains how both criminals and defenders are using...
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.