Maybe I can help fill the gaps.

I ran my own computer store with a small IT consultancy attached to it for a few years. Then I chose to pivot and get a "real job". Things change once you're married with a child on the way.

Like many, I started out doing 3 months to perm contract jobs. The first contract was a Linux system administrator at Google in Atlanta automating the huge fleet of servers there. I learned enough shell scripting to be dangerous, but it was mostly racking and stacking servers, and provisioning top of rack switches -- hello minicom.

3 months later I was working in tech support, for more money, at a company called Vocalocity, who was early in the VoIP game. That's where I learned how to PXE boot and flash Cisco IP phones to work with our custom Asterisk based backends. I was there almost a year and then it was time to move on.

This would continue every three months or so. I held jobs at places like Cox Communications working in the NOC during the night shift so I could be home with my daughter. Three to six months later I quit.

I know what you're thinking, this guy jumped around a lot. I had to, money was tight, and it was the fastest way to get a raise, and it also accelerated my learning. Coming from being your own boss it's really hard to get excited about an entry level job and look forward to working your way up the corporate ladder.

My skills really leveled up when I landed a full time job at Peer 1 Web Hosting, where I started in Tech Support working tickets and taking calls helping people with Linux servers, Plesk, and MySQL. It's true, it's always a DNS problem.

Peer 1 is where I really learned how to write code, it started with bash, and eventually Python. I automated the SSL certificate provisioning system, and wrote some scripts that allowed me to close tickets faster than anyone else.

About 6 months later I was promoted to the engineering team and worked on our automated provisioning system for Server Beach, acquired from Rackspace, which was the part of Peer 1 that hosted YouTube before YouTube was bought by Google. Server Beach ran those "Latency Kills" ads to help sale dedicated gaming servers.

That provisioning system was responsible for allowing people to order a server back in the early 2000s from a web form and have it provisioned in less than an hour. We PXE booted servers, configured RAID controllers, and bootstrapped the OS, including Windows, and handed back an IP address and login creds to the larger system.

I was there for over a year before landing a job that would double my salary around 2008, 2009.

I joined the company mentioned in the article, TSYS, where I brought in a lot of automation, thanks Puppet, and learned enough Java to earn the respect of the broader organization and really help transform the place.

I was a Red Hat Certified Engineer (RHCE) from my days at Peer 1 and I leveraged that set of skills to package all the production applications into fat RPMs (Java, JBoss, and all the war files required to make it work) in the same way we use containers today. I also revamped the CI/CD system leveraging Bamboo with tight Jira integration. I also helped the company move on from CVS to SVN. Don't ask.

We had automated deployments and tight integration with our apps over the course of the 3 years I was leading the team. We automated everything from Oracle running on AIX, to provisioning SSH keys and access to production servers based on Jira tickets and Puppet.

On the software development side I learned enough COBOL to port some of our mainframe jobs to Python. I wrote packed-decimal libraries and EBCDIC encoders so we could use Python going forward to process batch jobs. A big deal in the payments industry.

During my time at TSYS I really got exposed to open source and made some major contributions to Puppet and Cobbler -- I added a feature to Cobbler that enabled us to configure servers while leveraging Cobbler metadata and tools like Puppet.

I also started contributing to distutils and pip back in the day. I did some of the work that made pip and virtulenv play nice together. I also started public speaking at local meetup, PyATL, in Atlanta, and found my voice in the Python community.

It's my PuppetConf 2012 talk that landed me a job at Puppet Labs, the rest is history.