Security with Spirits

Oak Barrel Security
  • 5.0 (3)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

Oak Barrel Security is a partnership of cybersecurity professionals dedicated to training future security leaders while promoting security practices in everyday life for everyone.

  1. 08/28/2025

    Black Hat, DEFCON & “Windows Hell No”

    Pull up a glass and settle in; the crew is back from Vegas with stories you will not want to miss. In this episode of Security with Spirits, Jason shares his adventures at Black Hat and DEFCON, from walking 13 miles a day in the desert heat to discovering hacker villages on everything from aviation to lockpicking. We dive into the infamous Windows Hell No exploit, live phishing calls from the DEFCON stage, and why trust in AI is becoming the newest attack vector. Along the way, we swap drinks, from Bushmills and Monkey Shoulder to premixed Transfusions and even A&W Ice Cream Sundae soda, while debating vendor shenanigans, AI hype, and what it means to raise kids who understand security before they learn it the hard way. Whether you have been to the cons or just dream of making the trip, this one is packed with laughs, lessons, and a reminder that the only thing hotter than Vegas asphalt is the current state of cybersecurity.

    38 min

  2. 05/15/2025

    Redundancy Is a Journey, Not a Destination

    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.

    26 min

  3. 05/01/2025

    We Solved Email, You’re Welcome

    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.

    18 min

  4. 04/17/2025

    Triple Distilled, Triple Casked, and Triple Tired

    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.

    24 min

  5. 02/13/2025

    Hacking Ethics: From Strip Poker to Mr. Robot

    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.

    55 min

  6. 01/30/2025

    Corporate Culture and Cyber Sociopaths

    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!

    23 min

  7. 01/16/2025

    Unofficial IT Help Desk?

    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!

    31 min

  8. 01/02/2025

    The Blame Game: Passing the Buck in IT Support

    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!

    22 min
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Ratings & Reviews

5
out of 5
3 Ratings

About

Oak Barrel Security is a partnership of cybersecurity professionals dedicated to training future security leaders while promoting security practices in everyday life for everyone.

Information

  • Creator
    Oak Barrel Security
  • Years Active
    2022 - 2025
  • Episodes
    43
  • Rating
    Explicit
  • Copyright
    © Oak Barrel Security
  • Show Website
    Security with Spirits