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
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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...
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Child Predator Tactics
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Kids spend more time online than ever, and for the most part it feels normal. They’re gaming, watching videos, and chatting with friends. But hidden in those same spaces are adults who know how to pose as kids, build trust, and push conversations into dangerous territory. Parents might think it couldn’t happen to their child, yet detectives see how quickly an “innocent” interaction can turn into grooming or extortion. That’s the world Detective Seth Cockerham works in every day. He’s been in law enforcement in Texas for close to a decade, and the last few years have been dedicated...
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Identity Trafficking
Easy Prey
Some people are willing to hand over their identities for cash, while organized fraudsters are lining up to buy them. What used to be a matter of stolen credit cards has turned into a global marketplace where personal details fuel large-scale fraud. Now with AI, automation, and deepfakes making impersonation easier than ever, it’s becoming much more difficult to protect identities. To understand how we got here and what can be done, I spoke with Ofer Friedman, Chief Business Development Officer at AU10TIX. Ofer has spent more than 15 years in the identity verification and compliance...
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Technology, Trust & Time
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Technology is moving faster than our ability to process its impact, forcing us to question trust, motivation, and the value of our time. Few people have had a closer view of those shifts than Esther Dyson. With a background in economics from Harvard, Esther built a career as a journalist, author, commentator, investor, and philanthropist, with a unique ability to spot patterns across industries and challenge assumptions before they become mainstream. She is the executive founder of Wellville, a ten-year nonprofit project dedicated to improving equitable well-being in communities across the...
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The Global Scam Battle
Easy Prey
Cybercrime continues to evolve in sophistication and scale, with attackers running their operations much like businesses. From ransomware gangs with customer support desks to AI-generated phishing campaigns that erase traditional red flags, scams are becoming harder to detect and stop. In this episode, David Bittner, host of the CyberWire Daily Podcast, shares his perspective on the changing landscape of fraud and cyberattacks. Drawing on his background in media, theater, and podcasting, as well as years of reporting on security issues, he explains how both criminals and defenders are using...
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AI Supercharges Scams
Easy Prey
Cybercriminals 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...
info_outlineCyberattacks aren’t just about hackers in hoodies anymore. Today, we’re up against professionalized, well-funded organizations that run like businesses. They use AI to crack defenses, run labs that simulate the tools we rely on, and rake in trillions while defenders struggle to keep pace. The scary part? Even the strongest companies and governments can fall behind when the threat landscape moves this fast.
My guest, Evan Powell, has spent nearly 30 years in the cybersecurity world. He’s the founder and CEO of Deep Tempo, and a serial entrepreneur who’s helped industries from cloud data to resilience engineering make big transitions. Evan knows what it looks like when attackers have the upper hand, and he’s seen firsthand how enterprises try to shift the balance.
In this conversation, Evan explains why compliance checkboxes aren’t enough, why raising the cost of an attack is often more realistic than stopping one outright, and how AI is reshaping both sides of the fight. He also shares the creative ways defenders are adapting, from honeypots to sock puppets, and the simple steps every one of us can take to make life harder for attackers.
Show Notes:
- [00:57] Evan Powell introduces himself as founder and CEO of Deep Tempo, with nearly 30 years in cybersecurity and tech innovation.
- [02:39] He recalls a high-profile spearphishing case where the CIA director’s AOL email and home router were compromised.
- [03:51] Attackers are professionalizing, running AI-powered labs, and making trillions while defenders spend billions and still fall behind.
- [07:06] Evan contrasts compliance-driven “checkbox security” with threat-informed defense that anticipates attacker behavior.
- [09:40] Enterprises deploy creative tactics like honeypots and sock puppet employees to study attackers in action.
- [12:22] Raising the cost of attack through stronger habits, better routers, and multi-factor authentication can make attacks less profitable.
- [15:01] Attackers are using AI to morph and simulate defenses, while defenders experiment with anomaly detection and adaptive models.
- [20:56] Evan explains why security vendors themselves can become attack vectors and why data should sometimes stay inside customer environments.
- [24:50] He draws parallels between fraud rings and cybercrime, where different groups handle exploits, ransomware, and money laundering.
- [26:29] The debate over “hacking back” raises legal and policy questions about whether enterprises should strike attackers directly.
- [30:18] Network providers struggle with whether they should act as firewalls to protect compromised consumer devices.
- [34:59] Data silos across 50+ vendors per enterprise create “Franken-stacks,” slowing real-time defense and collaboration.
- [37:28] AI agents may help unify security systems by querying across silos and tightening the OODA loop for faster response.
- [39:10] MITRE’s ATT&CK framework and open-source collaboration are pushing the industry toward more shared knowledge.
- [41:05] Evan acknowledges burnout in cybersecurity roles but sees automation and better tools improving day-to-day work.
- [42:59] Final advice: corporations should rethink from first principles with data-centric solutions, and consumers must build protective habits like MFA and secret family phrases.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.