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...
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Child Predator Tactics
Easy Prey
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
Easy Prey
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_outlineWhat happens when the drive to succeed masks deep emotional wounds and addiction? In this episode, Jonathan Schwartz shares a powerful and painfully honest account of how his life unraveled.
Once one of Hollywood’s most trusted financial advisors, Jonathan worked with icons like Beyoncé, Mariah Carey, and Gwyneth Paltrow. On the surface, he had it all. But underneath the success was a secret struggle with gambling and drug addiction that led him to steal millions from the very clients who trusted him most.
His fall from grace was dramatic and public, ending in a prison sentence and the loss of everything he had built. But that wasn’t the end of his story. Today, Jonathan is sober and rebuilding his life with purpose. As Program Director at Altus Rehab, he now helps others find their own way out of addiction and shame. His story is raw, real, and full of hard-earned wisdom for anyone who has ever felt like they couldn’t ask for help.
Show Notes:
- [01:30] Jonathan is a different person from who he was. He grew up in Upstate New York and his father left when he was four. His mom had a lot of stress and took it out on him which created childhood trauma.
- [03:34] Accounting was the subject that he was good at.
- [05:02] Eventually, his cousin gave him a job working in Los Angeles for celebrities.
- [06:33] In 2004, he became a partner in GSO business management. He got a break when Linkin Park was looking for someone in business management. Their success opened up the floodgates.
- [08:37] He began getting more and more A-list clients.
- [09:04] In 2010, he became addicted to gambling.
- [10:01] This eventually led to embezzlement from his celebrity clients. He placed the bet with this bookie everyday for 6 years.
- [13:48] He ended up embezzling about 7 million dollars.
- [14:12] When he stopped gambling he had suicidal ideation.
- [17:05] He always intended to pay the money back.
- [19:37] Jonathan shares a time when the bank wanted to call Alanis.
- [21:03] There was a point when his partners started to notice something wasn't right.
- [22:04] In 2015 he was fired by Alanis, but he continued to give his attention to his A-list clients.
- [24:42] He didn't want to expose anyone to the fact that he was committing crime. He never told a soul.
- [25:07] The dark secret was eating him inside, and he also had to deal with his unresolved trauma.
- [27:12] How Jonathan had to come clean with his wife, because he was scheduled for a lie detector test.
- [28:48] After failing the test, he was facing 23 years in prison. He negotiated a four to six year plea agreement.
- [31:14] He ended up being released early because of COVID.
- [32:11] He struggled to get a job and ended up going back to school, and now he's a marriage and family therapist with an emphasis on addiction and trauma.
- [34:00] In prison he had the opportunity to reflect on his bad decisions and read a lot of books.
- [36:33] He's proud to be sober and a nerd. His trauma is resolved, and he gets to help people in treatment not make the same mistakes that he made.
- [41:34] Celebrities today need to understand not to trust their business manager so quickly and to make sure that they're proactive in their financial affairs and that they're asking for source documents.
- [42:11] Audit your business manager with some level of frequency.
- [48:43] Don't go out and spend all your money. Treat your first dollars as your last dollars.
- [50:56] Jonathan has a book coming out in about 12 months.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.