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...
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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...
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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...
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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,...
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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...
info_outlineCybercriminals are accelerating their attacks in ways that weren’t possible a few years ago. Artificial intelligence is giving them the ability to spin up phishing campaigns, voice clones, and deepfakes in minutes instead of days. As a result, the gap between what’s genuine and what’s fake is closing fast, making it harder for both individuals and organizations to defend themselves.
I’m thrilled to welcome Brett Winterford, Vice President of Okta Threat Intelligence. Brett has had a front row seat to these changes. His team analyzes identity-based attacks and delivers insights to help organizations adapt their defenses. Brett previously served as Okta’s Regional CISO for Asia-Pacific and Japan and started his career as a journalist covering information security before moving into leadership roles in banking, government, and technology.
In this episode, Brett explains how AI is reshaping the speed and scale of cybercrime, why trusted platforms like email, SMS, and collaboration tools are being targeted, and what practical steps can reduce risk. He highlights the growing importance of phishing-resistant authentication methods like passkeys, the need for clearer communication between service providers and users, and the role of collaboration across industries and law enforcement in pushing back against attackers.
Show Notes:
- [00:00] Brett Winterford introduces himself as Vice President of Okta Threat Intelligence and explains how identity-based threats are monitored.
- [02:00] He shares his career path from cybersecurity journalist to CISO roles and now to leading threat intelligence.
- [05:48] Brett compares phishing campaigns of a decade ago with today’s AI-driven ability to launch attacks in minutes.
- [08:00] He notes how reconnaissance and lure creation have become easier with artificial intelligence.
- [10:40] Brett describes the shift from banking malware to generic infostealers that sell stolen credentials.
- [12:30] He explains how cryptocurrency changed the targeting of attacks by offering higher payouts.
- [14:21] We learn about the Poison Seed campaign that used compromised bulk email accounts to spread phishing.
- [15:26] Brett highlights the rise of SMS and other trusted communication channels as phishing delivery methods.
- [16:04] He explains how attackers exploit platforms like Microsoft Teams and Slack to bypass traditional defenses.
- [18:30] Brett details a Slack-based campaign where attackers impersonated a CEO and smuggled phishing links.
- [22:41] He warns that generative AI has erased many of the old “red flags” that once signaled a scam.
- [23:01] Brett advises consumers to focus on top-level domains, official apps, and intent of requests to detect phishing.
- [26:06] He stresses why organizations should adopt passkeys, even though adoption can be challenging.
- [27:22] Brett points out that passkeys offer faster, more secure logins compared to traditional passwords.
- [28:31] He explains how attackers increasingly rely on SMS, WhatsApp, and social platforms instead of email.
- [31:00] Brett discusses voice cloning scams targeting both individuals and corporate staff.
- [32:30] He warns about deepfake video being used in fraud schemes, including North Korean IT worker scams.
- [34:59] Brett explains why traditional media-specific red flags are less useful and critical thinking is essential.
- [37:15] He emphasizes the need for service providers to create trusted communication channels for verification.
- [39:29] Brett talks about the difficulty of convincing users to reset credentials during real incidents.
- [41:00] He reflects on how attackers adapt quickly and why organizations must raise the cost of attacks.
- [44:18] Brett highlights the importance of cross-industry collaboration with groups like Interpol and Europol.
- [45:24] He directs listeners to Okta’s newsroom for resources on threat intelligence and recent campaigns.
- [47:00] Brett advises consumers to experiment with passkeys and use official apps to reduce risk.
- [48:00] He closes by stressing the importance of having a trusted, in-app channel for security communications.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.