Elder Exploitation
Easy Prey
Aging parents often rely on the people closest to them for help, but what happens when that help becomes a way to take control? For Charles Wallace, the warning signs started small. His mother’s fridge was suddenly overfilled. A caregiver refused to provide receipts. Spending patterns began to shift in ways that did not make sense. At the time, each concern could be explained away. Looking back, they were part of something much larger. Charles spent 15 years in banking and finance, and after his mother’s death, he used that experience to reconstruct more than 3,000 transactions. What he...
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Art Heists
Easy Prey
The world of art theft looks glamorous in the movies, but the reality is far more complicated. From multi-million dollar forgery schemes to undercover FBI operations recovering stolen national treasures, art crime is a global industry hiding in plain sight. This conversation digs into how these crimes actually play out and why the people who pull them off often end up stuck with the very pieces they thought would make them rich. My guest today is Robert Wittman, a former FBI special agent and the founder of the FBI’s Art Crime Team. Over a 20-year career, he worked undercover in more...
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The Power of Prediction
Easy Prey
We make predictions all the time including about the weather, about traffic, about what someone is going to say next. It feels natural, even rational. But when algorithms start making predictions about us, whether we'll repay a loan, reoffend after prison, or respond to a medical treatment, something fundamental shifts. The forecast stops being a guess and starts becoming a verdict. My guest today is Carissa Veliz, a philosopher and associate professor at the University of Oxford, where she also researches at the Oxford Internet Institute. Her work focuses on the ethics of technology, privacy,...
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Privacy vs Reality
Easy Prey
Online security advice often sounds simple until you actually try to follow it. Between password managers, privacy settings, and data brokers, protecting yourself can start to feel like a full-time job. That gap between what sounds easy and what’s actually realistic is where a lot of people get stuck. My guest today is Yael Grauer, a freelance investigative technology reporter who covers privacy, security, digital freedom, hacking, and mass surveillance. She also works as a program manager of cybersecurity research at Consumer Reports, where she manages Security Planner, a free resource that...
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Wired to Trust
Easy Prey
It’s easy to think scams only work when someone misses something obvious. In reality, most of them don’t look obvious at the start. They show up as normal situations with just enough friction to notice, but not enough to stop. That small gap is where people tend to move forward instead of stepping back. My guest today is Tali Sharot, a cognitive neuroscientist who studies how we form beliefs and make decisions. She’s known for her research on the neural basis of human optimism, and her work has been published in leading journals. In her books, The Optimism Bias and The Science of...
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Intimate Partner Fraud
Easy Prey
Most scams leave a digital trail. A fake email, a spoofed number, a fraudulent website. You can trace them, report them, sometimes even reverse them. But what happens when the scam has no digital trail at all, because it isn't happening on a screen? What happens when the con is standing right in front of you, making you laugh, meeting your friends, and planning a future with you? My guest today is Tracy Hall. She's an author, keynote speaker, and senior marketing executive with over 25 years at some of the world's most recognizable tech companies including eBay, Virgin, GoDaddy, and...
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Identity without Passwords
Easy Prey
Every day, employees at hotels, restaurants, and resorts across the country are doing exactly what they were hired to do: being warm, responsive, and eager to help. It's what makes hospitality work. It's also what makes hospitality one of the most targeted industries in cybersecurity. When your entire workforce is trained to say yes, teaching them to be suspicious is an uphill battle. The smarter solution might be to take the target off their backs entirely. Jasson Casey is the co-founder and CEO of Beyond Identity, a company built around one idea: making identity-based attacks impossible....
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When Cybercrime Gets Personal
Easy Prey
Most security breaches don't begin with sophisticated code or elaborate technical exploits. They begin with a phone call, a convincing email, or someone at a help desk who just wanted to be helpful. The human layer is often the weakest link, and the criminals who understand that are the ones causing the most damage. My guest today is May Chen-Contino. She's the CEO of Unit 221B, a threat disruption company that delivers actionable intelligence to enterprises, law enforcement, and government agencies. Her background spans cybersecurity, fintech, and SaaS leadership at companies like PayPal and...
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Stopping Phone Scams
Easy Prey
Phone scams get dismissed as background noise or just annoying interruptions and unknown numbers with robotic voices we learn to ignore. But behind that noise is an industry built on psychology, automation, and staggering profitability. My guest today is Alex Quilici. He’s an engineer, entrepreneur, and the CEO of YouMail, a company focused on protecting consumers and businesses from unwanted and fraudulent calls. Alex has spent years analyzing how robocalls and scam campaigns are designed, how they evolve, and why they continue to work despite better technology and increased awareness. What...
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Stolen Identity - Stolen Peace
Easy Prey
Identity theft gets talked about a lot, but usually in the abstract: freeze your credit, watch your statements, don't click suspicious links. What doesn't get talked about nearly enough is what it actually feels like when someone isn't just using your card number, but is actively living as you. My guest today is Brooklyn Lyons. She's 25, recently married, and by her own admission, had no particular expertise in fraud or cybersecurity before October of 2024. That changed when her car window was smashed in a parking lot, and her work bag, laptop, wallet, driver's license, and everything...
info_outlineA 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. Zachary shares the inside story of a LockBit ransomware attack that unfolded while his team was still building foundational security controls, forcing real-time decisions about recovery, disclosure, negotiations, and whether paying a ransom was even an option.
We talk about the shame that keeps many cyber incidents hidden, the emotional weight leaders carry during these moments, and the practical realities that don’t show up in tabletop exercises from buying bitcoin to restoring systems when password managers are encrypted. It’s an honest, grounded discussion about resilience, preparedness, and why sharing these stories openly may be one of the most important defenses organizations have.
Show Notes:
- [04:05] Zachary Lewis explains why the absence of an immediate ransom note delayed suspicion of an attack.
- [06:00] The first technical indicators suggest something more serious is unfolding.
- [07:45] Discovering encrypted hypervisors and realizing recovery won’t be straightforward.
- [09:30] Zachary outlines when data exfiltration became a real concern.
- [11:05] Receiving the LockBit ransomware note confirms the organization has been compromised.
- [12:55] The 4:30 a.m. phone call pushes leadership into full crisis mode.
- [14:40] Zachary reflects on managing fear, responsibility, and decision fatigue mid-incident.
- [16:20] Executive expectations collide with technical realities during the breach.
- [18:05] Why “doing most things right” still doesn’t guarantee protection.
- [19:55] Cyber insurance begins shaping early response decisions.
- [21:35] Bringing in incident response teams and legal counsel under tight timelines.
- [23:20] Zachary describes working with the FBI and understanding jurisdictional limits.
- [25:10] What law enforcement can and cannot realistically provide during ransomware events.
- [26:50] Opening communication channels with the threat actors.
- [28:35] The psychological pressure behind ransomware negotiations.
- [30:10] Attacker-imposed timelines force rapid, high-stakes decisions.
- [31:55] Zachary walks through the practical challenges of acquiring cryptocurrency.
- [33:40] Why encrypted password managers created unexpected recovery barriers.
- [35:15] Determining which systems could be restored first—and which could not.
- [37:00] Lessons learned about backup integrity and offline recovery.
- [38:45] The importance of clear internal communication during uncertainty.
- [40:25] Balancing transparency with legal and reputational concerns.
- [42:10] How staff reactions differed from executive responses.
- [43:55] Zachary discusses the stigma that keeps many ransomware incidents quiet.
- [45:40] Why sharing breach stories can strengthen collective defenses.
- [47:20] MFA gaps and configuration issues exposed by the attack.
- [49:05] Why tabletop exercises fall short of real-world incidents.
- [50:50] Long-term security changes made after recovery.
- [52:30] Zachary offers advice for CISOs facing their first major incident.
- [54:10] What preparedness really means beyond compliance checklists.
- [56:00] Why resilience and recovery deserve equal priority.
- [58:30] Final reflections on leadership, accountability, and learning in public.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.