Diary Of A SysAdmin
Conversations with IT Pros to learn about their tech journeys and who they are beyond the keyboard.
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...