Elliot Strong: Improving peoples’ lives through technology

Our interview with Elliot Strong, Director of IT at Teespring.

What do you ACTUALLY do?

Think of ways to improve peoples’ lives through technology.

What types of devices do you support?

We are a mixed shop, sometimes feels like two different companies. One part is business operations which includes every department you might find at a tech company. That half is 95% MacOS products. The other half is a giant well-oiled production and fulfillment machine. That half is 90% Windows. With a good chunk of iOS devices for fulfillment.

What's your favorite piece of tech?

My Nintendo Switch. I call it a digital revolution that can only play games. The switch is single handily going to save mobile gaming. It makes travel so much less painful. I could go on for hours on the switches social impact, but I think the best example is I once drove 100 miles into the Mojave desert to meet an old friend halfway, just to play super smash brothers in the trunk of my car all afternoon. Gaming isn’t the focal point of my life anymore, but the switch is not allowing it to be removed.

What tools or apps are most important to your job?

My MacBook Pro…. My nickname in high school was “Windows”. I was so anti-apple it’s cringeworthy. When I convinced the CEO and HR to let me move from customer service to start the IT department, I bought a MacMini and thought “If I’m gonna support a company at the time that was 99% Apple, I should probably learn how to use them”

Do you prefer hands-on, or troubleshooting from afar?

I am 100% remote, so I really don’t have a choice. I do miss getting my hand dirty, but I’m really happy with what I do. We have a lot of small satellite offices that can’t justify a full-time IT staff since I already traveled regularly to a bunch of different offices I “convinced” my boss at the time to let me try working remote. It comes with its own downsides, but I wouldn’t trade it for the world. I’ve become pretty good at troubleshooting things from afar.

Favorite thing about your IT environment?

That it’s mine. In its entirety. We had one office, I was hire number 80, and our growth was already skyrocketing. All the IT processes, training, were designed by me from the ground up. I never graduated from college, but they couldn’t accurately teach what it would be like to run an IT department today. I started night classes in college while in high school, and almost got a degree but life happens. What did my semester on Windows Vista get me?

Thing you'd most like to change about it?

More control over SaaS environment, and less tools. Still a little too much overlap of tools that do similar things. IE: Office/GSuite, Dropbox/Drive, Jira/Pivitol, etc.

What's on your desk?

Work set up on the left, personal on the right. Car Keys/Flash Drive, Macbook, laptop cooler, Trackball, 32” UltraWide, Netgear ProSwitch, 27” 4k, Coffee Mug, Little Bose Speaker. Pretty sure I was repairing a media server when this picture was taken, which is why there is a tower on top of a tower off to the side.

How did you start your career in IT?

When I was seven years old, my father gave me a box of floppy disks and said if you format these I’ll give you 5$. I really do think that was a defining moment. Like most kids in our field, I would try to monetize my ability with side hustles in my teenage years. A big chunk of my education would unironically come from school. I had a job for three-years starting when I was 16 supporting our pretty large school district. I actually wanted to study psychology in college but IT was the lazy way out since I was pretty proficient already. Didn’t have to try as hard.

What are the biggest misconceptions of your role, internally or externally?

Externally: That I’m a programmer — Internally: That I’m a programmer

What was your proudest professional moment?

Getting my IT role at Teespring. I was working in customer service/account management. The internet was awful. When I started it was three daisy-chained ASUS home routers. I’m the new kid at the company, I’m not going to come in and start changing things but I had a theory it was MAYBE multiple different DHCP servers and the routers not configured in bridge/ap mode. When I offered to help I was told no, they hired a “wireless guy”. He installed a Motorola system with an AP controller you needed a serial cable to configure, configured nothing on it and left. I didn’t even have a cable to log in to the thing. He even added a SonicWall AND still left one of the Asus Routers. Surprise the internet was still trash.

People complained I offered to take a look and was told no again. This time they hired a team of LVC’s who came in and ran ethernet and a few switches everywhere. “WiFi is too congested the expert told the VP and he needed people on Ethernet” well now I’m not against ethernet everywhere but we already had drops to every desk, but it was for a phone system from Cox that had to be separate. I can’t imagine what they wasted on this project. Surprise Internet and WiFi was still trash.

I offered a third time, thinking I might get fired for being annoying but they finally had enough and said give it a go if you can fix the internet you can start the IT department. I ordered a free trial setup of a complete Meraki solution. All the drops were already in place, so came in over a weekend and set everything up. Granted I’ve only taken a few networking courses, and never built an enterprise network before. I didn’t have proper tools, I would just walk around with my laptop watch what AP I was connected to, look for packet loss, roam, etc. Everything seemed perfect I was so proud. Until Monday when everyone came in…

Packet loss again. Except with newly increased visibility, it seemed isolated to one AP. I had just moved across the country with nothing but a suitcase for this job, I didn’t even have a cable tester but Meraki switches do. The AP that served the most clients, in the center of the office had a bad cable. LVC came and put new ends on. I renamed the network so in everyone’s mind it was a brand new network (placebo effect)….

I was the king of the office for a while. Everyone was so happy with the results, and soon thereafter I would start my journey to Director of IT.

TL;DR – Network at Teespring was trash, wouldn’t let new kid/customer service agent look at it. After multiple failed vendors they eventually do, and I save the day securing my position and the start of the IT department.

What are the biggest challenges in your work?

Perception. ShadowIT definitely has had an impact on how IT is perceived. We try to own as much as we can, but then we are seen as blockers. If someone asks for access to something i’ve never even heard of we seem useless. Expected to be experts of tools we’ve just learned about five minutes ago. We do a really good job of looking like we know everything, but a lot of times we’re just running through a flowchart in our head trying to figure out how to help before having to step away and google something quick.

Most cringeworthy request?

I couldn’t share the most cringe-worthy stuff. I think it would be a breach of the trust that is placed on you when it comes to being ‘IT’. Something I did that was cringe-worthy. I was working a small repair shop chain in Arizona, after moving out of Wisconsin. An elderly lady called and asked me to fix her email over the phone. I kept insisting that it could be anything and she would need to bring it in, she wasn’t happy with that and demanded a solution over the phone. I said it could be anything and on my list of things was her internet connection, which she insisted worked, the example I gave was it could be anything a squirrel could have chewed your internet line even. If she brought it in, we could look at it for her. Apparently, she called her internet provider and claimed the tech told her a squirrel chewed her internet line and to send someone to fix it. My nickname from then on was Squirrel boy. ..I don’t think Phoenix even has squirrels.

Do you stay hydrated at work?

Cup of black coffee in the morning. Water the rest of the day.


Everything is GUI nowadays. College showed me how to use a serial cable to connect to a cisco router and configure it, but I just go to the Meraki website and do everything I need from there. Unless I’m doing some bulk repetitive tasks its almost all GUI.

DIY or turnkey?

Turnkey. IT feels a lot of pressure to not be seen as a cost center, which can sometimes have you being scrappy on labor. If I can save a ton of time and have a complete product delivered I’m going to go that route.

Where can people follow you online?

@fugetaboutit22 – Instagram

Are you an existing atSpoke user?