There Is No Finish Line in Cybersecurity- Ep 546
Help Me With HIPAA
Some things in life have a finish line. Cybersecurity is not one of them. There’s no victory lap, no tape to break, and definitely no moment where you can say, “Cool, we’re done here.” This episode dives into why cybersecurity is a never-ending process, what regulators are really telling organizations through their guidance, and how the most common security failures still come down to the basics—patching, cleaning up old systems, and actually paying attention. If you’ve ever hoped you could “set it and forget it” with security, this conversation explains why that mindset is...
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When AI Stops Being Helpful - Ep 545
Help Me With HIPAA
AI: the gift that keeps on glitching. While most folks are still marveling at how AI can write emails and fold laundry (okay, not quite yet), this episode pulls back the curtain on what happens when artificial intelligence stops being polite and starts getting dangerous. We're talking zombie agents, security holes big enough to drive a HIPAA violation through, and automated tools that might just be a little too eager to help. It's informative, a little terrifying, and more than a few chuckles along the way. More info at
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Even Security Leaders Make Human Mistakes - Ep 544
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You’d think the folks steering the cybersecurity ship would be the last ones to punch holes in the hull—but nope, even the pros trip over their own policies. In this episode, we dive headfirst into a cautionary tale where a CISO (yes, the security guy) admits to becoming the insider threat he warns others about. From skipping his own software vetting procedures to triggering network alarms like it’s the 4th of July, this story is equal parts cringe and crucial. Strap in as we explore how even the most iron-clad experts are still deliciously human. More info at
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But It Was Five Stars on Amazon - Ep 543
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Just because your smart fridge can order milk and your thermostat knows when you're chilly doesn’t mean your home network is safe from cyber shenanigans. In this episode, we’re roasting the myth that five-star Amazon reviews mean airtight security, dragging lazy VPN habits, and exposing how your toddler’s tablet might be the real Trojan horse in your living room. From forgotten firmware to doorbells that moonlight as spies, we’re pulling back the Wi-Fi curtain on all the ways your devices could be betraying you—with or without your permission. More info at
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After the Breach Notice Comes the Lawsuit - Ep 542
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Ever wonder what happens when patient record requests are ignored, invoices go wild, and cybersecurity takes a coffee break? Spoiler: it ends with lawsuits, settlements, and a whole lot of legal back-and-forth. In this episode, we unpack a right of access case that dragged on longer than a season of courtroom drama, and then dive into the spaghetti mess of post-breach chaos - where class action lawsuits spring up like mushrooms and documentation (or lack thereof) can make or break you. If you thought the breach was the worst part… oh honey, it’s just getting started. More info at
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2026 Planning Since Predicting Is Pointless - Ep 541
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Here’s the deal: making predictions about 2026 is about as useful as a chocolate teapot. So instead of peering into a cloudy crystal ball, we’re laying down some solid groundwork for planning ahead. We’re talking AI governance, backup strategies that actually work (yes, tested ones), and why you should absolutely know if your vendor quietly stopped signing BAAs. Buckle up—it’s a 2026 survival guide with fewer guesses and more “you got this.” More info at
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2025 Holiday Blooper Show
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It’s that time of year again where audio perfection goes to die and chaos reigns supreme! In this special episode, we celebrate ten years of podcasting excellence by showcasing the exact opposite: dogs with digestive drama, countdowns that never count down quite right, rogue microphones, clumsy kitchen accidents, and travel mics that seem personally offended by their own existence. Expect Donna’s thumb to take a hit (thanks, chef’s knife), David to escape suspicion of living off the grid, and Bojan to quietly question all his life choices while trying to make this circus...
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Why 95% of AI Dreams End in a Cold Shower - Ep 540
Help Me With HIPAA
You know that warm fuzzy feeling you get thinking AI will solve all your business problems and let you retire early? Yeah, this episode is the cold shower you didn’t know you needed. We’re talking about why most AI projects crash harder than a Segway on launch day, how businesses keep falling into the same traps, and why treating AI like a superpowered intern (instead of your replacement) might be the smarter move. More info at
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Digital Adulting Is Hard - Ep 539
Help Me With HIPAA
Adulting is hard — but digital adulting? That’s a whole new level of chaos. In this episode, we dive headfirst into the “Most Wired” survey like it’s a techie BuzzFeed quiz for healthcare organizations. From cyber headaches and budget excuses to AI hype and “we’ve always done it this way” energy, we unpack the nine domains that determine whether your digital health game is fire… or just floppy disk-level tragic. More info at
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Cloudflare Outage Exposed Stuff We Miss - Ep 538
Help Me With HIPAA
Ever wondered what really keeps the Internet running - and what happens when it all goes sideways? The latest Cloudflare outage served up a reality check, exposing just how much of our digital world hangs together with a mix of duct tape, toothpicks, and a whole lot of hope. In this episode we dive into how this outage sent shockwaves through everything from simple website clicks to healthcare payment systems, and why most folks had no idea Cloudflare was even a linchpin for their daily operations. More info at
info_outlineSome things in life have a finish line. Cybersecurity is not one of them. There’s no victory lap, no tape to break, and definitely no moment where you can say, “Cool, we’re done here.” This episode dives into why cybersecurity is a never-ending process, what regulators are really telling organizations through their guidance, and how the most common security failures still come down to the basics—patching, cleaning up old systems, and actually paying attention. If you’ve ever hoped you could “set it and forget it” with security, this conversation explains why that mindset is exactly what gets people into trouble.
More info at HelpMeWithHIPAA.com/546