Libsyn Directory

Technology, Trust & Time

Release Date: 10/01/2025

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...

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...

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...

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,...

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,...

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...

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...

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...

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...

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...

More Episodes

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 United States. Beyond her nonprofit work, Esther has been an active angel investor in healthcare, open government, digital technology, biotechnology, and even outer space. She’s currently focusing on health and technology startups, especially the ones that actually care about human connection instead of just making everything faster and more efficient.

When we chatted, Esther made this really compelling point about AI. She thinks we're asking the wrong question when we debate whether artificial intelligence is good or bad. What really matters, she argues, is how we choose to interact with it. We dove into some tough ethical questions about how quickly we're adopting these technologies, this concept she calls "information diabetes," and why being upfront about who's funding what and why is absolutely crucial if we want to trust anything anymore.

Show Notes:

[01:44] Esther describes her career path from journalism to independent investing and healthcare projects.
[02:52] She explains why Wellville had a set end date and connects it to her upcoming book on time and mortality.
[04:08] Esther gives her perspective on AI, tracing its evolution from expert systems to neural networks and LLMs.
[06:17] She stresses the importance of asking who benefits from AI and being aware of hidden motives.
[12:44] The conversation turns to ethical challenges, biased research, and the idea of “information diabetes.”
[15:37] Esther reflects on how wealth and influence can make it difficult to get honest feedback.
[18:09] She warns that AI speeds everything up, making it easier to do both good and harm.
[20:14] Discussion shifts to the value of work, relationships, and finding meaning beyond efficiency.
[25:45] Esther emphasizes negotiation, balance, and how ads and AI should benefit everyone involved.
[27:28] She highlights areas where AI could be most beneficial, such as healthcare, education, and reducing paperwork.
[29:26] Esther argues that AI companies using public data should help fund essential workers and services.
[31:08] She voices skepticism of universal basic income and stresses the need for human support and connection.
[34:55] Esther says AI is far from sentience and accountability lies with the humans controlling it.
[36:46] She explains why AI wouldn’t want to kill humans but might rely on them for energy and resources.
[37:33] The discussion turns to addiction, instant gratification, and the importance of valuing time wisely.
[41:02] Esther compares GDP to body weight and calls for looking deeper at its components and meaning.
[42:19] She explains why she values learning from failures as much as from successful investments.
[43:18] Esther closes with advice: ask good questions, stay curious, and never underestimate the power of a smile.

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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