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Before the Fraud Tsunami Hits with Ritesh Kotak

Easy Prey

Release Date: 08/27/2025

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Fraud doesn’t always announce itself with obvious warning signs. Quite often, it shows up wrapped inside something that feels routine — a purchase you’ve made before, a link that looks legitimate, a message that arrives at just the wrong moment. Nothing feels suspicious, so your guard stays down. By the time questions start forming, the transaction is already done. My guest today is Iremar Brayner. He’s spent more than 15 years working in fraud prevention and risk management across payments, retail, ride-hailing, fintech, and digital marketplaces. In his role at G2A, he leads fraud...

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Most cybersecurity conversations focus on stolen data, breached accounts, and attacks that live entirely on screens. This episode looks at a far more consequential threat: what happens when cyberattacks target the physical systems that keep society running. Power, water, transportation, and manufacturing. When those systems fail, the consequences aren’t just digital. They’re immediate, visible, and sometimes dangerous. My guest is Lesley Carhart, Technical Director of Incident Response at Dragos, a cybersecurity firm focused exclusively on protecting critical infrastructure. Lesley...

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Security failures rarely come from cutting-edge attacks or sophisticated tools. They happen in ordinary moments when someone holds a door, follows an instruction without questioning it, or finds a workaround that makes their day easier. Those small, human decisions are often the real entry points, and they tend to compound over time. This episode picks up the second half of our conversation on exploiting trust with FC Barker, a veteran ethical hacker and physical security expert known for legally breaking into banks, government buildings, and high-security facilities around the world. With...

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Exploiting Trust (Part 1) show art Exploiting Trust (Part 1)

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Most security failures don’t start with a dramatic breach or a mysterious hacker sitting in a dark room. They usually start quietly. Someone assumes a system is locked down. Someone trusts that a door shouldn’t open, or that a machine “just works,” or that no one would ever think to look there. Over time, those small assumptions stack up, and that’s where things tend to go wrong. Today’s guest is FC Barker, a renowned ethical hacker, social engineer, and global keynote speaker with more than three decades of experience legally breaking into organizations to expose their blind...

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A ransomware attack doesn’t always announce itself with flashing warnings and locked screens. Sometimes it starts with a quiet system outage, a few unavailable servers, and a sinking realization days later that the threat actors were already inside. This conversation pulls back the curtain on what really happens when an organization believes it’s dealing with routine failures only to discover it’s facing a full-scale cyber extortion event. My guest today is Zachary Lewis, CIO and CISO for a Midwest university, a 40 Under 40 Business Leader, and a former Nonprofit CISO of the Year....

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Why do smart, capable people fall for scams even when the warning signs seem obvious in hindsight? In this episode, Dan Ariely joins us to examine how intuition often leads us in the wrong direction, especially under stress, uncertainty, or emotional pressure. A renowned behavioral economist, longtime professor of psychology and behavioral economics at Duke University, and bestselling author of Predictably Irrational, The Upside of Irrationality, Misbehaving, and Misbelief, Dan has spent decades studying why rational people consistently make choices that don’t serve them.  We talk about...

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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...

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Scams aren’t what they used to be. These days, AI can write perfect emails, mimic voices, and even fake a video call so well you’d swear you were talking to the real person. The problem is, the timing of a scam can be just right when you’re distracted, busy, or looking for exactly what they’re offering. That’s when even the most careful person can get caught.

My guest, Ritesh Kotak, knows this world inside and out. He’s a cybersecurity analyst, an Ontario lawyer, and a tech innovator who’s worked with Fortune 500 companies and served in policing, where he helped start one of Canada’s first municipal cybercrime units. He’s got a BBA, MBA, and JD, all focused on privacy, cybercrime, and the way emerging tech impacts everyday life.

In our conversation, Ritesh explains how criminals are using AI as a weapon, how it can also be a shield, and why simple, low-tech steps, like having a secret phrase with family or confirming a request through a different channel, are still some of the best defenses. He even shares a close call he had himself, which is a good reminder that nobody’s immune when scams are this convincing.

Show Notes:

  • [00:50] Ritesh shares his background as a lawyer helping clients navigate AI, tech, and cybercrime.
  • [01:18] His fascination with technology began at age three after taking apart his father’s computer.
  • [03:59] In policing, Ritesh saw early signs of cybercrime blending with physical crime.
  • [06:55] He demonstrates cybersecurity risks by live hacking a police chief, leading to the creation of a cybercrime unit.
  • [09:16] A near-miss phishing scam involving discounted amusement park tickets highlights how timing plays a role.
  • [15:14] Spoofed calls and evolving scam tactics make detection harder despite telecom safeguards.
  • [17:09] Ritesh explains AI as both a sword for criminals and a shield for protection.
  • [20:00] Generative AI enables flawless phishing emails, fake websites, and realistic deepfake audio and video.
  • [28:00] Simple defenses like secret phrases and multi-channel verification can stop many scams.
  • [31:45] Reporting scams to police can help investigations and sometimes recover funds.
  • [33:17] Ritesh advocates for centralized fraud response centers to improve victim support.
  • [36:45] Calling a lawyer can help victims navigate legal and civil remedies.
  • [38:05] Final advice: pause, verify, and use low-tech habits to prevent high-tech crime.

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