Simply Secured

This week we chat with Bill Boston, also known as 'The Real Bilbo,' to explore his extensive journey from IT support roles to becoming a cybersecurity professional.

With over 20 years in support and a strong background in healthcare and consulting, Bill shares unique insights into overcoming mental health challenges, the importance of being fair, friendly, and firm, and how his military experience shaped his career. He also delves into the roles of generative AI in personal and professional settings and offers valuable advice for veterans transitioning into cybersecurity roles.

Tune in for an engaging conversation packed with real stories, career tips, and wisdom from the trenches of cybersecurity.

Connect with The Reel Bilbo!
- LinkedIn: https://www.linkedin.com/in/bill-boston-3860b856/
- YouTube: https://www.youtube.com/@TheReelBillbo
- Discord: @TheReelBilbo

Chapters:
00:00 Introduction to the Podcast and Bill Boston aka The Reel Bilbo
02:23 Bill Boston's Journey into Cybersecurity
06:08 Military Experience and Transition to IT
09:55 Advice for Veterans Entering Cybersecurity
11:59 Utilizing AI in Personal and Professional Life
16:02 Empowering IT Professionals in Cybersecurity
18:56 Creating and Sharing Knowledge through Videos
23:20 Types of Leaders and Early Career Challenges
25:54 The Three F's of Leadership
26:59 The Importance of Kindness in Leadership
27:20 Trekking as a Means of Recharging
31:48 Backpacking Logistics and Comparisons to Cybersecurity
34:40 Rapid Fire Questions
43:32 Final Thoughts and Farewell

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
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Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

This week we have a captivating conversation with Christine Smoley, as she shares her journey from an academic background in phenomenology to a successful career in cybersecurity.

Key topics include networking at DEFCON, the importance of language acquisition and mental models, challenges of building security teams in startups, and her unique international experiences in Russia.

This episode offers valuable insights into the complexities of transitioning into cybersecurity and the importance of continual learning.

Connect with Christine on LinkedIn:
LinkedIn - https://www.linkedin.com/in/christine-smoley-92697358

Chapters:
00:00 Introduction to Simply Secured Podcast
00:43 Meet Christine Smoley
01:09 Defcon Poker and EFF Fundraising
02:05 Christine's Cybersecurity Journey
03:29 From Academia to Cybersecurity
04:52 Skills and Knowledge Transfer
10:51 Challenges in Skill Acquisition
14:41 Building Security in Startups
18:12 Evaluating Vendors and Third-Party Risks
23:25 Cultural Perspectives on Cybersecurity
27:24 Rapid Fire Questions
34:43 Final Thoughts and Farewell

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

This week we chat with Brent Buch, also known as Code Brew, to explore his fascinating transition from working in the food and beverage industry to becoming a junior database administrator and aspiring cybersecurity professional.

Brent discusses the challenges he faced breaking into the cybersecurity field, the value of transferable skills from bartending, and the importance of maintaining a work-life balance. He also shares insights on certification, industry resources, and tips for managing burnout. Tune in to hear his compelling journey and advice for anyone looking to make a similar career leap.

Chapters:
00:00 Discovering Cybersecurity: A YouTube Inspiration
00:48 Introduction to Simply Secured Podcast
01:30 Meet Brent Booth: From Bartender to Cybersecurity Professional
03:17 Brent's Journey into Cybersecurity
05:20 Challenges and Skills in Cybersecurity
12:15 Balancing Work and Family Life
21:43 Rapid Fire Questions and Fun Facts
27:50 Conclusion and Final Thoughts

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

In this episode of Simply Secured, host James Mcquiggan engages in an insightful and entertaining conversation with Dan “The Haircut Fish” Rearden. Dan shares his unconventional journey from various odd jobs and college culinary arts to becoming a SOC analyst.

Dan talks about his love for technology, self-guided learning through TryHackMe, and transitioning from IT help desk roles to cybersecurity. Known for his popular cybersecurity memes, Dan elaborates on the importance of humor in the community and how he uses it to connect and educate others. He also discusses his involvement in Capture the Flags (CTFs), current projects, the value of self-made tools in Python, and his future aspirations in detection engineering.

Episode Links:
- LinkedIn: https://www.linkedin.com/in/danrearden/
- YouTube: https://www.youtube.com/@danrearden384
- Discord: HaircutFish
- GitHub: https://github.com/haircutfish

Resources Mentioned in Interview:
- Security+ - https://www.comptia.org/en-us/certifications/security
- ISC2 CC - https://www.isc2.org/certifications/cc
- Detection Engineering - https://www.detectionengineering.net

Chapters:
00:00 Introduction and Early Career
00:42 Welcome to Simply Secured Podcast
01:15 Meet Dan 'Haircut Fish' Rearden
04:03 Dan's Journey into Cybersecurity
07:58 Daily Life of a SOC Analyst
10:35 Business Email Compromise Insights
16:10 Python Projects and Scripting Skills
22:29 Overcoming Roadblocks in Cybersecurity
23:01 The Origin of Cybersecurity Memes
23:55 Creative Process Behind Memes
26:55 Impact of Memes in the Cyber Community
31:31 Capture the Flag (CTF) Strategies
34:16 Certifications and Learning Paths
36:15 Rapid Fire Questions
43:23 Final Thoughts and Farewell

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

On this week’s episode we chat with Tyson Benson and explore his diverse career as a senior product cybersecurity analyst for ZFI.

With a background in patent law, Benson shares his unique insights on the importance of cybersecurity in the automotive industry, particularly as it pertains to software-defined vehicles.

Discover the pivotal moments that led him to this field, the legal and regulatory challenges he faces, and his perspectives on the future of cybersecurity.

Don't miss this insightful conversation that digs deep into the real stories of cybersecurity practitioners making a significant impact.

Chapters:
00:00 Introduction to Cybersecurity Passion
00:42 Podcast Overview and Host Introduction
01:16 Guest Introduction: Tyson Benson
01:55 Tyson's Journey into Cybersecurity
02:13 Patent Law to Product Cybersecurity
04:29 Automotive Cybersecurity Challenges
10:58 Importance of Product Security Incident Response
14:33 Supply Chain Security in Automotive Industry
17:55 Human Risk in Automotive Cybersecurity
20:49 Legal Experience in Cybersecurity
26:14 Skills for Automotive Cybersecurity
29:07 Rapid Fire Questions
36:42 Final Thoughts and Words of Wisdom

Connect with Tyson:
- LinkedIn - https://www.linkedin.com/in/tysonbenson/
- YouTube - https://www.youtube.com/@tysonbenson
- X: https://x.com/tysonbenson
- Discord: **0xTyson**

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

Today we chat with Debon Grady, an IT Security Specialist with the South Carolina Department of Mental Health. Debon shares his unique path from music education major to cybersecurity expert, discussing key moments, valuable skills learned, and the importance of mentorship.

Discover his thoughts on the relationship between red and blue teams, the significance of continuous learning, and his hobbies including video games and latte art. Stay tuned for rapid-fire questions and insights into Devin's approach to career success in cybersecurity.

Episode Links:
- LinkedIn: https://www.linkedin.com/in/ldgv
- YouTube: https://www.youtube.com/@DebonairCyber
- Discord: Debonair Cyber

Chapters:
00:00 Introduction and Background
00:06 Discovering Cybersecurity
00:45 Podcast Introduction
01:23 Devin's Journey into Cybersecurity
04:58 Skills from Music to Cybersecurity
06:48 Mentorship and Career Advice
08:55 Certifications and Job Search
15:23 Red Team vs Blue Team
17:03 Learning New Tools
19:17 Personal Interests and Hobbies
24:34 Rapid Fire Questions
26:58 Final Thoughts and Farewell

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

Today we chat with Cristina Pawlica, a distinguished member of the Simply Cyber community with an extensive background in cybersecurity and military service. Cristina shares her unique journey from serving in the Air Force as a Force Support Officer to pursuing a career in cybersecurity.

She delves into crucial leadership lessons and discusses the significant role of cybersecurity in K-12 education institutions. The conversation touches on her active involvement in the 2010 Foundation, which supports Air Force Academy cadets, and her passion for volunteering and helping build cyber resilience.

This episode concludes with a rapid-fire segment, providing a fun glimpse into Christina's personal preferences and insights on cybersecurity.

Episode Links:
- LinkedIn - https://www.linkedin.com/in/cristina-pawlica
- Foundation 2010 - https://www.2010foundation.org

Resources Mentioned in Interview:

- SimplyCyber Con Presentation - https://www.youtube.com/watch?v=P7ssW-OScdQ
- SimplyCyberCon - https://simplycybercon.org

Chapters:
00:00 Introduction to Elevating Cyber Careers Podcast
00:31 Meet Christina Polla: From Air Force to Cybersecurity
01:35 Christina's Cybersecurity Journey
05:53 Leadership Lessons from the Air Force
09:38 Creating Cybersecurity Content on LinkedIn
14:05 Current State of Cybersecurity in K-12 Schools
23:44 The 2010 Foundation: A Class Initiative
26:17 Introduction to the 2010 Foundation
26:45 Cadet for a Day Program
27:23 Supporting Cadet Parents
27:58 Addressing Hardships at the Academy
29:43 The Importance of Volunteering
31:42 Travel and Cybersecurity
35:09 Rapid Fire Questions
44:22 Conclusion and Final Thoughts

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

Welcome back for Season 2! We kickoff with a graduating senior from Rensselaer Polytechnic University as she transitions from academic research to industry applications in the world of cybersecurity.

In this episode, we sit down with Shoshana Sugerman, to explore her journey from classroom to conference room. We delve into Shoshana's work on Grover's algorithm for quantum-enhanced threat detection and her experiences during a summer internship at Cisco.

Shoshana offers advice for aspiring cybersecurity professionals, emphasizing the importance of networking, asking questions, and embracing failures as learning opportunities.

Episode Links:
- LinkedIn - https://www.linkedin.com/in/shoshanasugerman/

Resources Mentioned in Interview:
- ISC2 Congress Presentation to Brian & Shoshana’s presentation - https://www.isc2.org/Insights/2024/10/ISC2Congress-Generative-AI-for-Cybersecurity-Awareness-Training
- Quantum Paper: https://news.rpi.edu/2025/03/03/rensselaer-cybersecurity-collaboratory-researchers-break-new-ground-quantum-security
- Generative AI Article: https://www.techrepublic.com/article/generative-ai-security-training/
- Computer Coach Generative AI: Cybersecurity Awareness Training: Benefits, Limitations, & Skills for the Workforce: https://www.youtube.com/watch?v=-7WqRrIPcYk

Chapters:
00:00 Introduction to Simply Secured Podcast
00:34 Meet Shoshanna Sugarman
02:46 Shoshanna's Journey into Cybersecurity
05:17 AI and Security Awareness Training
07:32 The Role of Human Oversight in AI
13:27 Generative AI in Education
16:14 Exploring Quantum Computing
21:15 Internship Experience at Cisco
25:32 Advice for Aspiring Cybersecurity Students
29:18 Rapid Fire Questions and Closing Thoughts

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

In this episode we delve into the world of cybersecurity with Fleetus Poston III, a dynamic public speaker, passionate mentor, and cybersecurity evangelist.

Fleetus shares his journey, including his 'aha' moment in cybersecurity, handling imposter syndrome, the significance of a healthy security culture, and the impact of a recent reduction in force on his career.

He also discusses the importance of mentorship, his content creation on LinkedIn and YouTube, and offers invaluable advice for up-and-coming professionals in the field.

Links:
- LinkedIn: https://www.linkedin.com/in/fletusposton
- YouTube: https://www.youtube.com/@fletusposton
- Website: https://www.fletusposton.com/
- Sessionize: https://sessionize.com/fletusposton/

Chapters:
00:00 Introduction to Elevating Cyber Careers Podcast
00:33 Meet the Guest: Fleet Us Poston II
01:57 Fleet Us Poston's Cybersecurity Journey
04:15 The Role of a Cybersecurity Evangelist
06:16 Building a Healthy Security Culture
16:04 Challenges in Cybersecurity Defense
18:25 The Future of AI in Cybersecurity
20:32 Mentorship and Career Advice
23:13 Sharing Wisdom and Staying Engaged
25:19 Content Creation and Micro Learning
26:06 Cybersecurity Awareness and Mentorship
29:31 Impact of Reduction in Force
35:45 Rapid Fire Questions
40:35 Final Thoughts and Advice

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials

This week, we chat with Federico Castro, a cybersecurity professional and member of the ISC2 Central Florida chapter, known by his nickname 'FedEx'.

We discuss FedX’s transition from physical security and construction into cybersecurity, fueled by his diagnosis of ADHD and his pursuit of education. Federico highlights the importance of networking, mentorship, and continuous learning in cybersecurity.

He also shares insights into his passions, family life, and his YouTube channel aimed at helping others break into the field.

Just like prior shows, we conclude with a fun rapid-fire question segment, revealing more about Federico's personality and interests.

 Episode Links:
- LinkedIn: https://www.linkedin.com/in/fedx-castro
- YouTube: https://www.youtube.com/@the-fedx-channel
- Discord Handle: FedX

Resources Mentioned in Interview:
- Central Florida ISC2: https://chapters-centralflorida.org
- Seminole Sate College - https://www.seminolestate.edu
- HackCFL - https://hackcfl.com

Chapters:
00:00 Introduction and Guest Welcome
01:12 Federico's Journey into Cybersecurity
03:08 Advice for Beginners in Cybersecurity
05:31 The Importance of Networking and Mentorship
06:37 Conference Experiences and Insights
15:56 Passion for Technology and Early Influences
20:39 Starting a YouTube Channel and Helping Others
25:36 The Power of Community in Cybersecurity
27:42 Balancing Family and Tech
29:42 Involving the Next Generation
32:38 Finding Balance with Your Partner
33:46 Rapid Fire Questions
42:56 Reflecting on Career and Legacy

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Connect with your host: James R. McQuiggan:
LinkedIn: https://linkedin.com/in/jmcquiggan
YouTube: https://www.youtube.com/@jamesmcquiggancissp
Website: https://jamesmcquiggan.com
TikTok: https://www.tiktok.com/@jamesmcquiggan.cissp
Email: [email protected]
==========================================================
Simply Cyber empowers people who want a rewarding cybersecurity career 💪
==========================================================
Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.com
YouTube Title Graphic: London Company
Video Podcast graphics: Katie McQuiggan (www.katiemcquiggan.com)
Music Provided by: AppleHillStudios at Envato Elements
=========================
Presented by Simply Cyber Media Group
=========================
All the ways to connect with @SimplyCyber
https://SimplyCyber.io/Socials