Security Chipmunks

Edna
  • 5.0 (2)
  • TECHNOLOGY
  • UPDATED BIWEEKLY

Welcome to Security Chipmunks where we talk about the development of cybersecurity skills. To stay up to date in today's world you need to be resilient, that’s why as Advanced Persistent Chipmunks we keep chipping away at it.

  1. DEC 12

    How John Hammond Turns Community, Curiosity, And Consistency Into Cyber Mastery

    Send us a text The most reliable way to learn cybersecurity is to touch the tools, break things safely, and build them back with intent. That’s the heartbeat of our conversation with John Hammond, where we unpack how hands-on labs, community feedback, and a healthy mindset can speed up your growth and make it last. We start with the spirit of DEF CON: presenters acting like instructors, guiding real exercises where attendees build muscle memory instead of passive notes. John explains how that approach inspired Just Hacking Training—an accessible, collaborative platform with expert-led curriculum, live ranges, quizzes, and walkthroughs you can actually use on the job. We talk about why practical, application-first learning is the quickest path for newcomers who don’t have enterprise tools at home and need portfolio-ready proof of skill. From there, we explore the tension between chasing headlines and building evergreen skills. John’s framework is simple: anchor your time in fundamentals that compound—networking, scripting, Linux, detection engineering, exploit analysis—and use the latest vulnerabilities as sparks for practice. You’ll avoid the burnout of the news cycle while keeping your curiosity alive. We dive into “learning in public” as a force multiplier: sharing notes, repos, and writeups creates a feedback loop, accelerates improvement, and leaves visible evidence of progress for hiring managers and mentors. Imposter syndrome and overwhelm come for everyone. John offers grounded ways to cope: compare yourself only to yesterday’s you, turn doubt into small daily reps, and step off the treadmill when you need recovery. Pair that with community—Discords, conferences, local meetups—and you’ll find both accountability and energy. For anyone starting today, the blueprint is clear: keep it fun, share your work, and show up where people learn together. If this resonates, follow John on YouTube, LinkedIn, and X, and explore Just Hacking Training for name-your-price labs and courses. Enjoy the episode, then subscribe, leave a review, and tell a friend who’s trying to break into cybersecurity—what’s the one skill you’re doubling down on next? Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    23 min

  2. OCT 3

    From Sysadmin to Ethical Hacker: Phillip Wylie shares Skills, Labs, and Real-World Strategies

    Send us a text Want a real-world map into penetration testing instead of a maze of hot takes? We sit down with Philip Wiley—offensive security veteran, teacher, and author of The Pentester Blueprint—to unpack practical paths that work today. Philip traces his journey from sysadmin to consultant and shows how prior roles become leverage in security: command line fluency, networking instincts, audit rigor, and the ability to translate technical findings into business impact. If you’ve wondered whether you “must” start in IT, you’ll hear why transferable skills matter more than a single prescribed path. We dig into how learning has shifted. Five years ago, home labs were the default; now, cloud-based platforms like Hack The Box, TryHackMe, and Antisyphon accelerate skill-building without the drag of fragile setups. Philip breaks down which certifications best reflect hands-on ability—think PNPT, TCM’s junior pen tester, and OSCP—and how to structure your study with focused reps, thorough enumeration, and disciplined reporting. Expect honest advice about fundamentals over shortcuts, the value of repetition, and why a good methodology beats a bag of tricks. Mentorship and community run through everything here. Philip shares what successful learners actually do, how encouraging guidance can flip hesitation into action, and why showing up at B-Sides, OWASP, and local hacker associations opens doors you didn’t know existed. We also talk personal branding—publishing talks, write-ups, and even books—to make your progress visible and credible to hiring managers. You’ll leave with a weekly cadence you can start immediately: deliberate labs, concise notes, a study group, and one community touchpoint that compounds into opportunities. If this conversation helps you chart your next step into offensive security, follow the show, share it with a friend who’s studying, and leave a review so more learners can find it. Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    24 min

  3. SEP 16

    Small Businesses Are Prime Targets, But There Are Ways to Fight Back

    Send us a text "We're too small to be hacked" might be the most dangerous myth in small business cybersecurity today. As James Baierle, founder of SecurePoint Solutions, asks with a touch of irony – how exactly do you let the bad guys know to leave you alone? The hard truth is you can't, and that's why specialized security services for small businesses are more critical than ever. The cybersecurity landscape presents unique challenges for the 13 million American businesses with fewer than 10 employees. These organizations – from your favorite coffee shop to your child's daycare center – face the same sophisticated threats targeting Fortune 500 companies but lack the resources for enterprise-level protection. SecurePoint Solutions was born specifically to bridge this gap, providing scaled security solutions that make protection accessible to businesses of all sizes. For aspiring cybersecurity professionals, Baierle offers refreshingly practical career advice gained from his journey from Navy operations to founding his own security company. "Writing is what gets us paid," he emphasizes, noting that technical skills alone won't advance your career if you can't effectively communicate findings and impacts to non-technical stakeholders. He recommends starting a blog to showcase communication abilities and advises newcomers to manage expectations – you probably won't start as an elite penetration tester, but numerous opportunities exist in areas like Security Operations Centers where demand for talent is high. Beyond cybersecurity, Baierle shares his passionate advocacy for foster care, having adopted three siblings after years of fostering children. With approximately 200,000 foster beds needed nationwide, he suggests respite care as an accessible entry point for those interested in helping but uncertain about full-time commitment. This personal mission reflects the protective instinct that drives many security professionals to make a difference both within and beyond their technical expertise. Whether you're a small business owner concerned about cybersecurity, an aspiring professional looking to break into the field, or someone interested in making a broader social impact, this conversation offers valuable insights into protecting what matters most. Ready to chip away at building better security for your business or career? This episode is your starting point. Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    27 min

  4. AUG 26

    Standing Out in the Security Crowd: Jerry Bell's Path to Success

    Send us a text What does it take to build an online community of 50,000 cybersecurity professionals? Jerry Bell, founder of InfoSec Exchange and former CISO for IBM Cloud, reveals the journey behind creating one of the most influential Mastodon servers in the security world. When Twitter underwent significant changes in 2022, Bell's Fediverse server, which he'd quietly maintained since 2017, suddenly became the landing spot for thousands of security professionals seeking a new digital home. The explosive growth from around 100 users to 50,000 within a month created both technical and human challenges. "The technical aspects, while challenging, don't hold a candle to the complexities of moderating a community that large," Bell explains, detailing the balancing act between enabling free expression and maintaining community standards. Bell's contributions to the security community extend well beyond Mastodon. As the host of the Defensive Security Podcast since 2011, he pioneered professional-grade security content when most security podcasts were either consumer-focused or entertainment-oriented. This content creation directly contributed to his career advancement, eventually helping him secure the position of CISO for IBM Cloud. For aspiring security professionals, Bell offers three key pieces of advice: prioritize human networking over resume submissions, develop a deep understanding of networking technology regardless of specialization, and find ways to differentiate yourself through content creation or community involvement. Whether discussing persistent cloud security challenges like misconfigured S3 buckets or sharing his journey from factory maintenance worker to security executive, Bell's story demonstrates how creating content and building communities can transform a career path. What digital footprint are you creating that will make hiring managers recognize your name when your resume lands on their desk? Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    25 min

  5. MAY 1

    DEF CON's Noob Village: Creating Space for Cybersecurity Beginners

    Send us a text Ready to break down the intimidating barriers of cybersecurity conferences? Join us for an eye-opening conversation with Josh Mason, a former Air Force pilot and cyber warfare officer who's on a mission to make the industry more accessible to newcomers. Josh shares his personal journey from military service into the cybersecurity field, revealing the challenges he faced along the way and how those experiences inspired him to help others navigate similar paths. As the creator of DEF CON's upcoming Noob Village, he's tackling a problem many have whispered about but few have addressed: the often overwhelming nature of hacking conferences for first-time attendees. The Noob Village concept is refreshingly innovative - creating a dedicated space where beginners can find guidance, connections, and support without judgment. We explore the unique features of this initiative, including a beginner-friendly CTF with a twist: participants earn recognition not just for solving challenges but also for helping others succeed. With talks from industry experts like Jason Haddix and Philip Wiley, plus a "No Stupid Questions" table staffed by friendly volunteers, the village promises to transform how newcomers experience DEF CON. Perhaps most valuable is Josh's insight into effective networking in cybersecurity. Forget strategic business card exchanges - he advocates for simply showing up with a friendly attitude and genuine curiosity. Through his experiences at conferences like Wild West Hacking Fest (which he describes as feeling like "a family reunion I look forward to"), we discover how the most meaningful professional connections often start with casual conversations and shared experiences. Curious about breaking into cybersecurity or making industry events more inclusive? This episode offers practical wisdom, encouragement, and a reminder that behind every intimidating technical challenge is a community of people eager to help you succeed. Connect with the Noob Village Discord community at noobvillage.org/Discord and discover how you can contribute to making cybersecurity more welcoming for everyone. Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    22 min

  6. APR 19

    Mentorship, Connection, and Playing the Long Game

    Send us a text Discover how to navigate the complex landscape of cybersecurity careers with Fletus Poston III, Senior Manager for Security Operations at Crash Plan. Drawing from his diverse background spanning regulated utilities, financial services, and software development since 2007, Fletus shares transformative insights about finding your place in the security ecosystem. The conversation challenges conventional wisdom about breaking into cybersecurity, with Fletus presenting a compelling metaphor: "Security is like a city" with diverse roles from entry-level positions to executive leadership. Rather than fixating solely on offensive security roles, he encourages newcomers to explore various disciplines to find their perfect fit, whether in SOC analysis, governance, or offensive security. What truly sets this episode apart is Fletus's counter-intuitive approach to career advancement. Instead of mass-applying to positions, he advocates for a strategic "long game" - identifying target companies, building relationships with their employees over time, and positioning yourself as a knowledgeable peer rather than just another applicant. This approach leverages the power of internal references, dramatically increasing your chances of success. The discussion delves into the often-overlooked human elements of security, from establishing effective mentorship relationships to implementing practical safeguards against emerging threats like AI voice scams and deepfakes. Fletus shares actionable advice for creating secure password practices and verification techniques that protect against sophisticated social engineering. Whether you're just starting your cybersecurity journey or looking to advance to the next level, this episode delivers practical wisdom from someone who's navigated the field's challenges firsthand. Remember Fletus's parting advice: "You add value to every room that you enter," and approach security problems with perspective and understanding rather than simply saying "no." Socials Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    27 min

  7. APR 2

    From Abacus to Agentic AI: How Technology is Transforming Our Security Landscape with FedX

    Send us a text Ever wonder how cutting-edge AI is transforming cybersecurity from the inside out? Security analyst Federico "FedEx" Castro pulls back the curtain on how innovative professionals are leveraging artificial intelligence to revolutionize threat detection and response. FedEx takes us into the fascinating world of custom GPT agents, showing how he's created specialized tools that instantly process vulnerability information and generate tailored reports for different stakeholders. Far from theoretical discussions, this conversation delivers practical insights about implementing AI within security frameworks while navigating organizational data policies. "AI is a tool," FedEx emphasizes. "If you don't type the right input, you get a bad output." The discussion ventures beyond technology into the human elements of cybersecurity. FedEx candidly shares how his neurodivergent thinking patterns create both unique challenges and remarkable advantages in security work. "It's a struggle, but it's a superpower at the same time," he explains, describing how ADHD traits like hyperfocus and pattern recognition help him excel at threat hunting and anomaly detection. His perspective offers a refreshing reminder that diversity in thinking styles strengthens our collective security posture. With phishing attacks becoming increasingly sophisticated through AI assistance, security professionals must continuously evolve their skills and knowledge. FedEx shares valuable insights from cybersecurity conferences and technical workshops, emphasizing the importance of community connections for staying ahead of emerging threats. Ready to enhance your security toolkit with AI capabilities? Want to better understand how diverse thinking styles contribute to stronger security teams? Listen now for practical guidance from someone who's walking the talk at the intersection of AI and cybersecurity. Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    29 min

  8. MAR 7

    CTF Chronicles: Unpacking Our Wild West Hackin' Fest Experience

    Send us a text Dive into our exhilarating adventure at Wild West Hackin' Fest, where our casual visit transformed into a thrilling Capture the Flag (CTF) competition! Join us as we share our journey from team formation to victory, highlighting the unique dynamics of working as a group in high-pressure scenarios. In this episode, we discuss the preparation that went into strategizing and setting up our technical environments, showcasing the importance of diverse skill sets among team members. Capture the Flag events challenge participants not only to excel in their technical abilities but also to think critically and adapt quickly. Our discussion reveals the real lessons learned from both successes and setbacks, where communication played a critical role in navigating the challenges faced during the competition. You’ll hear stories of camaraderie and shared knowledge as we engaged with our peers and competitors, making connections that extend beyond the event. As cybersecurity continues to challenge professionals in innovative ways, our experiences at the Wild West Hackin' Fest provide valuable insights into the blend of fun, teamwork, and learning that defines CTF competitions. Whether you're a seasoned competitor or just starting in cybersecurity, there’s something to learn from our adventure. Be sure to subscribe and share your thoughts with us! We are joined by our guest today Derek Rook  LinkedIn - https://www.linkedin.com/in/derekrook/  YouTube - https://youtube.com/@derekrook Twitter - https://twitter.com/_r00k_ Socials Join our Chipmunk community Discord server: https://discord.gg/9yfWP6evYQ Follow us on Twitter: https://twitter.com/SecChipmunk You can find us online at: https://securitychipmunks.com

    30 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

Welcome to Security Chipmunks where we talk about the development of cybersecurity skills. To stay up to date in today's world you need to be resilient, that’s why as Advanced Persistent Chipmunks we keep chipping away at it.

Information

  • Creator
    Edna
  • Years Active
    2021 - 2025
  • Episodes
    23
  • Rating
    Clean
  • Copyright
    © 2025 Security Chipmunks
  • Show Website
    Security Chipmunks