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_outline
You Are Traceable with OSINT
Easy Prey
Publicly available data can paint a much clearer picture of our lives than most of us realize, and this episode takes a deeper look at how those tiny digital breadcrumbs like photos, records, searches, even the background of a Zoom call can be pieced together to reveal far more than we ever intended. To help break this down, I’m joined by Cynthia Hetherington, Founder and CEO of The Hetherington Group, a longtime leader in open-source intelligence. She also founded Osmosis, the global association and conference for OSINT professionals, and she oversees OSINT Academy, where her team trains...
info_outline
Anyone Could Walk In
Easy Prey
Sometimes we forget how much trust we place in the little things around us like a lock on a door or a badge on someone’s shirt. We see those symbols and assume everything behind them is safe, but it doesn’t always work that way. A person with enough confidence, or the right story, can slip through places we think are locked down tight, and most of us never notice it’s happening. My guest today is Deviant Ollam, and he’s one of the rare people who gets invited to break into buildings on purpose. He talks about how he fell into this unusual line of work, the odd moments that shaped his...
info_outline
The Scam You Never See Coming
Easy Prey
Fraud today doesn’t feel anything like it used to. It’s not just about somebody skimming a credit card at a gas pump or stealing a check out of the mail. It has gotten personal, messy, emotional. Scammers are building relationships, earning trust, and studying the little details of our lives so they can strike when we’re tired, distracted, or dealing with something big. And honestly, most people have no idea how far it’s gone. My guest, Ian Mitchell, has spent more than 25 years fighting fraud around the world and leading teams in the financial sector. He’s the founder of The Knoble,...
info_outline
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,...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outlineThe 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 navigating complex cyber environments.
Chris talks about his unconventional path into the industry, how much harder it is for new professionals to enter cybersecurity today, and the surprising story of how he recently fell for a fake Facebook ad that showcased just how convincing AI-powered scams have become. He breaks down the four major waves of InfoSec from the rise of the web, through mobile and cloud, to the sudden, uncontrollable arrival of generative AI. He then explains why this fourth wave caught companies completely off guard. GenAI wasn’t something organizations adopted thoughtfully; it appeared overnight, with thousands of employees using it long before security teams understood its impact. That forced long-ignored issues like data classification, permissions cleanup, and internal hygiene to the forefront.
We also dive into the world of agentic AI which is AI that doesn’t just analyze but actually acts and the incredible opportunities and dangers that come with it. Chris shares how low-code orchestration, continuous penetration testing, context engineering, and security “mesh” architectures are reshaping modern InfoSec. Chris spends a lot of time talking about the human side of all this and why guardrails matter, how easy it is to over-automate, and the simple truth that AI still struggles with the soft skills security teams rely on every day. He also shares what companies should think about before diving into AI, starting with understanding their data, looping in legal and privacy teams early, and giving themselves room to experiment without turning everything over to an agent on day one.
Show Notes:
- [00:00] Chris Kirschke, Field CISO at Tuskira, is here to explore how AI is reshaping cybersecurity and why modern threats look so different today.
- [03:05] Chris shares his unexpected path from bartending into IT in the late ’90s, reflecting on how difficult it has become for newcomers to enter cybersecurity today.
- [06:18] A convincing Facebook scam slips past his defenses, illustrating how AI-enhanced fraud makes traditional red flags far harder to spot.
- [09:32] GenAI’s sudden arrival in the workplace creates chaos as employees adopt tools faster than security teams can assess risk.
- [12:08] The conversation shifts to AI-driven penetration testing and how continuous, automated testing is replacing traditional annual reports.
- [15:23] Agentic AI enters the picture as Chris explains how low-code orchestration and autonomous agents are transforming security workflows.
- [18:24] He discusses when consumers can safely rely on AI agents and why human-in-the-loop oversight remains essential for anything involving transactions or access.
- [21:48] AI’s dependence on context becomes clear as organizations move toward context lakes to support more intelligent, adaptive security models.
- [25:46] He highlights early experiments where AI agents automatically fix vulnerabilities in code, along with the dangers of developers becoming over-reliant on automation.
- [29:50] AI emerges as a support tool rather than a replacement, with Chris emphasizing that communication, trust, and human judgment remain central to the security profession.
- [33:35] A mock deposition experience reveals how AI might help individuals prepare for high-stress legal or compliance scenarios.
- [37:13] Chris outlines practical guardrails for adopting AI—starting with data understanding, legal partnerships, and clear architectural patterns.
- [40:21] Chatbot failures remind everyone that AI can invent policies or explanations when it lacks guidance, underscoring the need for strong oversight.
- [41:32] Closing thoughts include where to find more of Chris’s work and continue learning about Tuskira’s approach to AI security.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.