Grab a glass and hunker down, Episode 41 is a disaster-filled ride through flooding basements, flaming UPS units, rogue trees, and one very immersive surround sound moment gone hilariously wrong. In this episode, the guys crack open bottles of homemade peach rum, Japanese whisky, and Southern Comfort while reflecting on personal and professional disasters, and the lessons learned from them.

From tabletop exercises that don't go as planned to the bitter reality of "risk transference" in cloud services, this episode is all about preparation, perspective, and learning the hard way. Plus: truffle-fueled commentary, lost cell phones, and why sometimes it’s just better to let someone else do the job.

This week the crew gets personal with a new segment, “What’s in Your Drawers?”, where each host digs into their mysterious tech junk drawers to unearth everything from microSD adapters to forgotten iPhones. Alongside the laughs, the team dives deep into the ongoing saga of corporate email: the phishing, the overload, the AI marketing creep, and why email just won’t die.

Is email still essential, or is it a relic in need of retirement? Could zero trust, internal-only inboxes, or even fax-to-shredder workflows be the future? Spoiler: no one likes read receipts, and everyone loves dunking on email.

Pull up a barstool and pour a glass, this episode dives deep into impostor syndrome, burnout, and the drive to stay sharp in cybersecurity and tech. Jason, Ben, Jonathan, and Tony swap stories over Claremont Steep, Jameson Triple Triple, and trusty Buffalo Trace as they explore the highs and lows of learning, staying motivated, and navigating the ever-changing infosec landscape. From early bourbon missteps to burnout waves and the power of good teams, this one blends introspection, nerdy joy, and a dash of sarcasm. Bonus: Monkey Island life lessons and a few light jabs at accountants.

In this episode of Security with Spirits, Jason, Ben, Jonathan, and Tony welcome their first guest, Andre, a cybersecurity veteran with a story that starts on a Commodore 64. Over drinks like Papa’s Pillar rum, Jameson Orange, and hot toddies, the group dives into discussions about privacy, cybersecurity ethics, and the blurred lines between white hats, black hats, and gray areas. They explore the "Dexter-style hacker," social engineering, and share practical tips for improving personal privacy and security—all with a side of laughs and spirited banter.

Join us for Security with Spirits, the podcast where cybersecurity meets cocktails and camaraderie! Hosted by Jason, Ben, Jonathan, and Tony, each episode blends cybersecurity insights, workplace culture commentary, and plenty of laughs over a drink. Tonight, we explore how repressive corporate culture can turn employees into "cyber sociopaths" and discuss why fostering creativity and authenticity in the workplace is key to securing your organization's digital frontlines. Whether you're into margaritas, Irish coffee, or Kalúa-infused hot chocolate, pull up a stool and enjoy the conversation. Cheers!

In this episode of Security with Spirits, Jason, Ben, Jonathan, and Tony gather to discuss a common cybersecurity pain point: how the infosec team often becomes the "unofficial help desk" for other IT departments. With humor, insightful analogies, and plenty of drinks, the crew dives into the reasons behind this phenomenon, including trust, broad knowledge bases, and the evolving role of security teams. They also explore strategies to set boundaries, improve collaboration, and avoid burnout. As always, the discussion is paired with great drinks from Buffalo Trace bourbon to hot tea (yes, really). Cheers!

In this episode, the team dives into one of IT’s most common (and frustrating) phenomena: the blame game. From network woes to firewall fiascos, Jason, Ben, Jonathan, and Tony swap stories about ticket-passing, stalling tactics, and dealing with vendors who are quick to point fingers. With drinks in hand, they share pet peeves, laugh over relatable support desk moments, and even confess their own tactics for buying a little extra time. If you’ve ever been stuck in the crossfire of IT troubleshooting, this episode is a must-listen!

Join the Security with Spirits crew as they take a break from firewalls and phishing attacks to share their favorite ways to unwind. Jason, Ben, Jonathan, and Tony talk bourbon, Florida water scares, and the unexpected stress relief found in gaming, dog walks, and disc golf. Listen in for their hilarious misadventures in 3D printing, including “listening” for lost glow-in-the-dark golf balls and fighting off rogue filament messes. It’s a laid-back episode all about hobbies that take them off the grid—at least for a little while. Pour a glass, kick back, and enjoy the ride.

Join Jason, Tony, Ben, and Jon as they toast to a new year of cybersecurity goals and gear up for what’s ahead in 2024. From securing home networks and using hidden email addresses to avoid spam, to the latest deepfake scams and predictions of AI-driven cyber threats, the team covers it all. With a mix of humor and insight, they explore personal resolutions, the realities of AI in security, and what the future may hold for phishing, cryptocurrency regulations, and more. Kick off the year with practical tips and a lighthearted look at the evolving cybersecurity landscape.

In this lively episode of Oak Barrel Security, the team sips on drinks ranging from Crown Apple to Hard Mountain Dew while diving into the latest breaches and blue team basics. They discuss high-profile cyber incidents, including Toyota's refusal to pay ransom and the 23andMe data breach, touching on the implications of leaked personal information and the need for fundamental cybersecurity practices. Plus, they share their top holiday wish list items for security enthusiasts—from lockpick sets to recommended reads like The Blue Team Handbook and How They Tell Me the World Ends. This episode blends serious insights with a dash of humor and the occasional tangent, making it a must-listen for anyone in the cybersecurity space.