Diary Of A SysAdmin
Conversations with IT Pros to learn about their tech journeys and who they are beyond the keyboard.
From Help Desk to IT Leadership: Andrew Johnson's Journey
Andrew Johnson shares his journey in the IT field, starting from his early days in education to his current role in systems management. He emphasizes the importance of community, continuous learning, and the evolution of technology, particularly in relation to AI and automation. Andrew also discusses his experiences with user groups and conferences, and offers advice for aspiring IT professionals.
Chapters
00:00 Introduction to Andrew Johnson's Journey
05:44 Career Development in IT and Education
11:54 The Importance of Community and Resources
17:54 Engagement in Online Learning and User Groups
23:45 Public Speaking and Sharing Knowledge
29:22 The...
From Paramedic to Redmond, Sean Bulger’s tech journey (Replay)
In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous learning in the tech industry. Sean also offers insights into the evolving nature of endpoint management and the impact of AI on the workforce, encouraging listeners to embrace curiosity and personal development.
Chapters
00:00 Introduction and Conference Reflections
01:08 Consulting Insights and IT Career...
Code, Cloud & Confidence with Hailey Phillips (Replay)
In this episode, Hailey Phillips shares her journey from an HR internship to becoming a prominent figure in the IT industry. She discusses her passion for technology, the importance of automation and cloud computing, and the role of soft skills in tech. Hailey also reflects on her experiences in the gaming industry, her travels to Japan, and the significance of continuous learning and personal development. She emphasizes the need for aspiring IT professionals to embrace tools like PowerShell and the value of therapy in enhancing communication skills.
Chapters
00:00 Introduction to Hailey Phillips and Her Journey
03:14...
Bryan Dam – Onesies, Sysadmin Life & Sneakernet Solutions (Replay)
In this conversation, Bryan discusses his early experiences in IT management, particularly focusing on the unconventional methods he employed, such as the 'sneaker net' approach, to manage devices and install software. He reflects on the challenges and best practices he learned along the way.
Chapters
00:00 Introduction and Background
03:47 Career Transition from Software Engineering to System Administration
06:28 Early Experiences in System Administration
09:38 Learning and Adapting in a Small Organization
12:45 Challenges and Innovations in Endpoint Management
15:41 Scaling Up: Transition to a Larger Organization
18:54 Implementing Configuration Manager
21:46 Community Engagement and Learning
23:33...
Matt Zaske’s Mustache Origin + Task Sequences in 2025 (Replay)
Matt Zaske, a seasoned sysadmin in higher ed, dives into device management, Windows 11 migration, and how his theater background shapes his IT communication. He shares his path into tech speaking, explores home automation, and showcases his passion for 3D printing and custom conference collectibles. We also learn the fun origin story of his iconic mustache and his Sunday taco salad tradition—all highlighting his creativity and community spirit.
Chapters
00:00 Introduction to Matt Zaske
03:02 The Role of a SysAdmin in Higher Education
06:01 Device Management and Task Sequences
09:11 Wipe and Reload Process Explained
11:47 Windows 10 to...
Helpdesk Scars & PowerShell Wins with Andrew Taylor
Andrew Taylor shares his journey from studying business to becoming a seasoned IT professional with over 20 years of experience. He discusses his early days in help desk support, his transition to end user computing, and the challenges he faced in various IT roles, including managing multiple tenants in the MSP world. Andrew emphasizes the importance of community networking, learning through experience, and the critical role of PowerShell in modern IT management. He also reflects on his experiences writing the Intune Cookbook, freelancing, and the future of technology, including AI and cloud computing.
00:00 From Business to IT: Andrew's...
Writing, Teaching, and Defending: Ru Campbell’s IT Adventures
Ru Campbell shares his journey from starting in IT in 2012 to becoming a Microsoft 365 consultant and security expert. He discusses the importance of help desk experience, betting on oneself in career progression, and the transition to specializing in Microsoft Defender. Ru emphasizes the value of understanding security practices, the challenges of writing a technical book, and the benefits of networking and community engagement. He also touches on future technology trends, particularly AI, and offers advice for the next generation of IT professionals while sharing insights into his personal life and hobbies.
Chapters
00:00 The Beard and Its...
From Packaging Apps to Podcasting with Rory Monaghan
Rory Monaghan shares his extensive journey in the IT field, starting from his early days in application packaging to his current role in end user computing. He discusses the evolution of application virtualization, particularly App-V, and its impact on organizations. Rory emphasizes the importance of community through user groups and the value of podcasting as a medium for sharing knowledge. He also addresses the challenges in cybersecurity and the changing landscape of IT content creation, offering advice for future IT professionals to focus on AI, security, and employee experience.
Chapters
00:00 Rory Monaghan's Journey in IT
06:11...
Building Better Reporting with Garth Jones
Garth Jones shares his extensive journey in the IT field, starting from his early days running a BBS to becoming a pivotal figure in endpoint management with SMS. He discusses the evolution of IT roles, the importance of proactive management, and the challenges he faced while building Enhansoft. Garth also reflects on his experiences with blogging, writing books, and presenting at conferences, emphasizing the value of networking and community in the IT industry. He concludes with insightful advice for the next generation of IT professionals, encouraging continuous learning and passion for the field.
Chapters
00:00 Introduction to...
Networking, Fundamentals, and the Future of IT with Mattias Melkersen
In this conversation, Mattias Melkersen shares his journey from dropping out of school to becoming a successful IT consultant. He discusses the importance of mentorship, continuous learning, and the impact of AI on IT management. Mattias emphasizes the need for networking and community building in the IT field, as well as the significance of understanding the fundamentals of technology. He also reflects on balancing work and personal life, and shares insights for the next generation of IT professionals.
00:00 From High School to IT: A Unique Journey
05:51 Building a Career in IT Consulting
12:00 The Growth of...
Pedaling Through IT Careers with Paul Winstanley
In this conversation, Paul Winstanley shares his journey in the IT industry, starting from his early days in retail IT support to specializing in endpoint management and becoming a community leader through blogging and speaking engagements. He discusses the importance of mentorship, the evolution of his career into consulting, and the impact of AI on the future of IT jobs. Paul also reflects on his personal interests, including cycling, and offers valuable advice for the next generation of IT professionals.
00:00 The Journey Begins: Early IT Career
09:36 Mentorship and Learning in IT
14:20 Transitioning to Enterprise IT...
From Dismantling a PC at 14 to Co-Founding a Tech Company with Jose Schenardie
In this conversation, Jose Schenardie shares his journey from starting his IT career in Brazil to becoming a co-founder of a cybersecurity company in Australia. He discusses the importance of niche conferences like MMS, the evolution of endpoint management with Intune and SCCM, and the role of AI in shaping the future of IT. Jose emphasizes the value of community engagement, the challenges of starting a business, and offers advice for new IT professionals.
00:00 Introduction to Jose Schenardie
03:05 The Value of Conferences
05:47 Early Career and IT Journey
11:38 Transition to Endpoint Management
17:27 The Evolution...
Cloud Skills, Content Creation & Cardio – Andy Jones IT Journey
In this conversation, Andy Jones shares his extensive journey in the IT field, starting from his early days in web development to his current role focusing on cloud technologies and Intune. He discusses the importance of continuous learning, mentorship, and the evolution of technology, particularly AI and its implications for IT professionals. Andy also reflects on his experiences with YouTube content creation and offers valuable advice for aspiring IT professionals, emphasizing the need for balance between work and personal life.
00:00 Introduction to Andy Jones and His Journey
04:59 Career Evolution and Learning Journey
09:26 The Impact of...
Helpdesk to Consulting with Chris Cavazos on Shaping Tech Careers
In this conversation, Chris Cavazos shares his journey in the IT field, starting from his early experiences in the 90s to his current role as a principal consultant. He discusses the importance of mentorship, the transition from in-house IT to consulting, and the impact of Azure Virtual Desktop during the pandemic. Chris also touches on his personal interests, including his love for Star Wars and football, and offers advice for aspiring IT professionals. The conversation concludes with thoughts on the future of AI in the industry and Chris's favorite sports teams.
00:00 Introduction to Chris Cavazos
04:15 Early...
From Construction Sites to Configuration Profiles with Jóhannes Geir Kristjánsson
Johannes Geir Kristiansson shares his unique journey from a construction background to a successful career in IT, particularly in endpoint management and Intune. He discusses the challenges and rewards of transitioning from a hands-on trade to a more abstract field, emphasizing the importance of community and knowledge sharing. Johannes also reflects on the future of IT, including the impact of AI and the shift towards passwordless solutions, while offering valuable career advice for those entering the tech industry.
Chapters
00:00 From Construction to IT: A Unique Journey
16:49 Transitioning from Configuration Manager to Intune
24:18 Building Community...
How Dustin Gullett Went from Mowing Lawns to Microsoft MVP
Dustin Gullit shares his journey from mowing lawns for a school district to becoming an IT consultant with a wealth of experience in military network security, healthcare IT, and MDM solutions. He discusses the evolution of Intune, the impact of AI on technology and daily life, and his passion for photography and blogging. Dustin emphasizes the importance of sharing knowledge and the potential of AI in shaping the future of technology, all while balancing family life and personal interests.
00:00 Dustin's Journey Begins
02:49 Military Experience and IT Growth
05:25 Transitioning to the Healthcare Sector
08:28 Exploring MDM...
How Nearly Becoming a Doctor Led to a Career in Cyber Security with Spencer Alessi
Spencer Alessi shares his journey from almost becoming a doctor to pivoting to IT, emphasizing the importance of help desk experience, mentorship, and continuous learning. He discusses his passion for systems administration, the significance of disaster recovery testing, and his transition into security. Spencer also reflects on his experiences in podcasting and content creation, offering valuable insights for new IT professionals.
Chapters
00:00 From Medicine to IT: A Career Shift
05:39 Mentorship in IT: The Path to SysAdmin
10:55 The Importance of a Testing Lab
16:22 Accidental Entry into Security
22:11 The Art of ARP Spoofing
28:12...
Naming OUs and Racing Bikes: The Balanced Life of Michael Escamilla
Michael Escamilla shares his journey in the IT field, discussing his experiences at conferences, his involvement with OSD Cloud, and the importance of community engagement. He reflects on his career path, the challenges faced in IT, and the significance of automation. Michael emphasizes the need for continuous learning and offers advice for aspiring IT professionals, while also sharing personal interests and memorable experiences in the industry.
00:00 Introduction and Networking at MMS
02:46 Speaking Experience and Session Content
05:41 Involvement with OSD Cloud
08:46 Career Beginnings and Early IT Experience
11:48 Transitioning to New Roles and Responsibilities<...
Imposter Syndrome, Authorship, and Entrepreneurship with David Brook
David Brook shares his journey in the IT field, discussing his early experiences, the importance of apprenticeships, and the challenges of starting his own business. He emphasizes the value of community, public speaking, and the need for continuous learning in the fast-paced world of technology. David also opens up about his struggles with imposter syndrome and the importance of sharing knowledge to help others in the industry.
00:00 Introduction and Late Night Work Habits
02:41 David's Journey into IT
05:48 The Apprenticeship Experience
08:41 Becoming an Author
11:23 Writing for the Audience
13:15 Imposter Syndrome and Community Engagement<...
From Paramedic to Redmond, Sean Bulger’s tech journey
In this conversation, Sean Bulger shares his journey through the IT landscape, discussing his experiences as a consultant, the importance of a growth mindset, and the value of mentorship. He reflects on his diverse career path, that included jobs as a plumber and paramedic, and emphasizes the significance of community engagement and continuous learning in the tech industry. Sean also offers insights into the evolving nature of endpoint management and the impact of AI on the workforce, encouraging listeners to embrace curiosity and personal development.
Chapters
00:00 Introduction and Conference Reflections
01:08 Consulting Insights and IT Career...
Steve Weiner’s Unexpected Tech Journey: Music, Youtube, and Modern Management
In this engaging conversation, Steve Weiner, co-founder of Get Rubix, shares his unique journey from a music career to the tech industry, detailing his experiences at Apple and as a tech consultant. He discusses the evolution of his YouTube channel, the impact of pandemic on IT practices, and the importance of community engagement through open-source solutions. Steve emphasizes the need for passion in one's work, the significance of people skills in the tech field, and offers valuable advice for the next generation of IT professionals. He also shares his thoughts on the future of AI in IT and the...
Code, Cloud & Confidence with Hailey Phillips
In this episode, Hailey Phillips shares her journey from an HR internship to becoming a prominent figure in the IT industry. She discusses her passion for technology, the importance of automation and cloud computing, and the role of soft skills in tech. Hailey also reflects on her experiences in the gaming industry, her travels to Japan, and the significance of continuous learning and personal development. She emphasizes the need for aspiring IT professionals to embrace tools like PowerShell and the value of therapy in enhancing communication skills.
Chapters
00:00 Introduction to Hailey Phillips and Her Journey
03:14...
Steve Jesok’s Journey - From Rockstar to IT Rockstar
In this conversation, Steve Jesok shares his journey into the IT field, his involvement with user groups, and the evolution of community engagement in technology. He reflects on his early career, transitioning from a professional musician to an IT professional, and highlights the importance of user groups as resources for learning and networking.
00:00 Introduction to Steve Jesok and tcsmug
03:46 Steve's Journey into IT and User Groups
06:52 The Evolution of User Groups and Community Engagement
09:52 From Musician to IT Professional
12:53 Early Days at IBM and Automation
16:03 Scripting and Systems Management
18:49 Building Agile...
Dean Ellerby on IT, AI, and Launching His YouTube Journey
In this engaging conversation with Dean Ellerby, he shares his journey through the tech industry, starting from his early experiences in a gaming company to becoming a consultant specializing in SCCM and Intune. He discusses the challenges and learning moments throughout his career, including his transition to content creation on YouTube during the pandemic. The conversation also touches on his involvement in organizing tech events and maintaining a work-life balance while managing multiple responsibilities. In this conversation, the speaker shares insights on their journey into public speaking, experiences with Apple management and Intune, and the importance of learning from...
Community, AI, and the Future of IT with Mike Terrill
Fabian and Mike Terrill discuss a variety of topics ranging from the extreme weather in Phoenix to the intricacies of community engagement through user groups like azsmug. They delve into the challenges faced by user groups post-COVID, the evolution of systems management, and the future of device management in the context of AI. Mike shares valuable advice for aspiring IT professionals, emphasizing the importance of continuous learning and networking.
Chapters
00:00 Weather and Location Differences
02:03 Racing Adventures and Experiences
05:56 Community Engagement and User Groups
12:01 The Evolution of User Groups Post-COVID
18:08 Reflections on the...
Episode 4: Mike Terrill
Fabian and Mike Terrill discuss a variety of topics ranging from the extreme weather in Phoenix to the intricacies of community engagement through user groups like azsmug. They delve into the challenges faced by user groups post-COVID, the evolution of systems management, and the future of device management in the context of AI. Mike shares valuable advice for aspiring IT professionals, emphasizing the importance of continuous learning and networking.
Chapters
00:00 Weather and Location Differences
02:03 Racing Adventures and Experiences
05:56 Community Engagement and User Groups
12:01 The Evolution of User Groups Post-COVID
18:08 Reflections on the...
From Portraits to PowerShell: David Segura on Building OSDCloud
In this conversation, David Segura discusses the birth of OSDCloud, highlighting its popularity and the significant impact of automation in IT management. He also touches on future trends in system administration, emphasizing the importance of adapting to new technologies and I learn how down to earth he is!Â
Chapters
00:00 Introduction to David Segura and IT Journey
03:36 Transition from Photography to IT
06:29 Career Development and OSD Expertise
09:40 The Birth of OSD Cloud
12:38 Impact of Community and Conferences
15:35 User Groups and Networking
18:32 Personal Insights and Future Directions
25:05 Exploring the Latest Tech G...
Bryan Dam – Onesies, Sysadmin Life & Sneakernet Solutions
In this conversation, Bryan discusses his early experiences in IT management, particularly focusing on the unconventional methods he employed, such as the 'sneaker net' approach, to manage devices and install software. He reflects on the challenges and best practices he learned along the way.
Chapters
00:00 Introduction and Background
03:47 Career Transition from Software Engineering to System Administration
06:28 Early Experiences in System Administration
09:38 Learning and Adapting in a Small Organization
12:45 Challenges and Innovations in Endpoint Management
15:41 Scaling Up: Transition to a Larger Organization
18:54 Implementing Configuration Manager
21:46 Community Engagement and Learning
23:33...
Matt Zaske’s Mustache Origin + Task Sequences in 2025
Matt Zaske, a seasoned sysadmin in higher ed, dives into device management, Windows 11 migration, and how his theater background shapes his IT communication. He shares his path into tech speaking, explores home automation, and showcases his passion for 3D printing and custom conference collectibles. We also learn the fun origin story of his iconic mustache and his Sunday taco salad tradition—all highlighting his creativity and community spirit.
Chapters
00:00 Introduction to Matt Zaske
03:02 The Role of a SysAdmin in Higher Education
06:01 Device Management and Task Sequences
09:11 Wipe and Reload Process Explained
11:47 Windows 10 to...