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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 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:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 investigators, analysts, and practitioners from all experience levels.
Cynthia shares how she started her career as a librarian who loved solving information puzzles and eventually became one of the earliest people applying internet research to real investigative work. She talks about the first wave of cybercrime in the 1990s, how she supported law enforcement before the web was even mainstream, and why publicly accessible data today is more powerful and more revealing than ever. We get into how OSINT actually works in practice, from identifying a location based on a sweatshirt logo to examining background objects in video calls. She also explains why the U.S. has fewer privacy protections than many assume, and how property records, social media posts, and online datasets combine to expose surprising amounts of personal information.
We also explore the growing role of AI in intelligence work. Cynthia breaks down how tools like ChatGPT can accelerate analysis but also produce hallucinations that investigators must rigorously verify, especially when the stakes are legal or security-related. She walks through common vulnerabilities people overlook, the low-hanging fruit you can remove online, and why your online exposure often comes from the people living in your home. Cynthia closes by offering practical advice to protect your digital footprint and resources for anyone curious about learning OSINT themselves. This is a fascinating look at how much of your life is already visible, and what you can do to safeguard the parts you'd rather keep private.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 career, and why understanding human behavior matters just as much as understanding locks or alarms. Listening to him describe these situations, where he's walking through offices, popping doors, or blending in with repair crews, makes you realize how blind we can be to our own surroundings.
We also get into the practical side of things: the mistakes companies make, the small fixes that go a long way, and why teaching employees to slow down and ask a few extra questions can make all the difference. It's an eye-opening conversation, especially if you've ever assumed your workplace is more secure than it really is.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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, a nonprofit bringing banks and industry leaders together to protect vulnerable people from scams, human trafficking, and exploitation. Ian has seen the evolution of fraud firsthand, from the old-school days of stolen cards to the organized global crime networks using technology, AI, and human manipulation to scale at a pace we've never experienced before.
What stood out to me is Ian's belief that the strongest defense doesn't start with fancy tools or tighter security. It starts at home. Real conversations with our kids about safety online. Checking in on aging parents. Talking openly with people we trust so scammers can't isolate us and break us down. It's serious work, but Ian is hopeful. He believes there are far more good people than bad, and when we look out for each other, we're a lot harder to exploit.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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, 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:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 collaborations across government and industry to disrupt ransomware actors at their source.
We talk about how ransomware groups operate, why paying a ransom rarely solves the problem, and what layered defense really means for organizations and individuals. Cynthia also shares how AI is reshaping both sides of the cyber arms race and why she believes hope, not fear, is the most powerful tool for defenders.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 him a rare mix of real-world perspective and research-based insight. His work on metal theft, catalytic converter crime, and package theft sheds light on who's actually committing these offenses, what motivates them, and which prevention methods truly work.
We discuss how fluctuating metal prices influence theft rates, why cameras often fail to stop certain crimes, and how a few simple design changes to your home can make a real difference. Dr. Stickle also shares unexpected examples of modern theft, from stolen pets to disappearing beehives, and explains how communities can act early before small trends turn into national headlines.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 financial crimes investigator and program manager at The Knoble, Freddie has made it his mission to bridge the gap between institutions and individuals. He shares the heartbreaking and hopeful moments that define his work including one phone call that saved a life. Along with how that experience changed the way he thinks about what true fraud prevention really means.
Freddie also opens up about The Knoble's Post-Scam Victimization Guide, a collaborative, trauma-informed resource designed to help victims regain control of their lives and prevent re-victimization. From crypto scams to romance cons, he explains how these schemes keep evolving, why empathy is still one of the best tools we have, and how every fraud fighter can make a difference simply by listening and responding with humanity.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 massive global business. He shares what's changed over the years and why those old "red flags" don't always work anymore and how new tools like deepfakes and AI have made deception harder to spot than ever.
Kit also talks about his newest project, Serif Secure, a free tool he created to help people clean and protect their computers after a scam attempt. He's honest, thoughtful, and a little funny even when the subject is dark. By the end, you'll see just how much one person can do to fight back.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
Links and Resources: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 digital identity verification faster, smarter, and safer. Bala has more than twenty years in the industry, including leadership roles at TransUnion, and he's seen firsthand how the race between innovation and exploitation never really ends. It just keeps speeding up.
In our conversation, Bala shares how generative AI has supercharged the fraud world, what makes identity such a fragile link in digital trust, and why biometrics may finally offer a way forward. We also dig into the psychology behind online risk, how convenience often wins over caution, and what small habits can help people protect themselves in an age where deception looks more real than ever.
Show Notes:Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.
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