Hello TechExams

I am a long time lurker, first time poster. I am an Active Duty Air Force member who works in the communications field. I'm a Server Admin/Desktop Support troop (temporary augmentee for a shortage of Client Systems guys). I've spoke to my brother about working in the field of IT, he is highly interested, but he is unsure of where or how to start. I figure I would ask you guys what your experience was landing your first job and how you got it. I've explored the forms and used my share of the search button, however I figured I would start a new thread because I feel like a lot of people come on here anyways looking for advice on how to get their first position, so maybe this can help more people than just my brother.
What I'm asking is,
1. What was the title of your first position?
2. What education (College, Certs, Apprenticeships, technical training, bootcamps etc.) did you aquire?
3. What experience (Customer service, Fixing family computers, etc.) did you have? Doesn't have to be formal experience.
4. And finally, was this a "I knew a guy", position?
I look forward to hearing answers, I follow a lot of posts on here and feel like this community is an excellent wealth of knowledge and experience.