Cyber Journeys: Transition, Leadership, and Trekking with Bill "The Reel Bilbo" Boston

21/11/2025 43 min Temporada 2 Episodio 8
Cyber Journeys: Transition, Leadership, and Trekking with Bill "The Reel Bilbo" Boston

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Episode Synopsis


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: @TheReelBilboChapters:00:00 Introduction to the Podcast and Bill Boston aka The Reel Bilbo02:23 Bill Boston's Journey into Cybersecurity06:08 Military Experience and Transition to IT09:55 Advice for Veterans Entering Cybersecurity11:59 Utilizing AI in Personal and Professional Life16:02 Empowering IT Professionals in Cybersecurity18:56 Creating and Sharing Knowledge through Videos23:20 Types of Leaders and Early Career Challenges25:54 The Three F's of Leadership26:59 The Importance of Kindness in Leadership27:20 Trekking as a Means of Recharging31:48 Backpacking Logistics and Comparisons to Cybersecurity34:40 Rapid Fire Questions43:32 Final Thoughts and Farewell==========================================================Connect with your host: James R. McQuiggan:LinkedIn: https://linkedin.com/in/jmcquigganYouTube: https://www.youtube.com/@jamesmcquiggancisspWebsite: https://jamesmcquiggan.comTikTok: https://www.tiktok.com/@jamesmcquiggan.cisspEmail: [email protected]==========================================================Simply Cyber empowers people who want a rewarding cybersecurity career 💪==========================================================Video Editing / Sound Engineering: Matthew Bliss, MB Podcasts - https://www.mbpod.comYouTube Title Graphic: London CompanyVideo 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 @SimplyCyberhttps://SimplyCyber.io/Socials

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