Embracing coworkers’ quirks can be a challenge for some. Client Engineer II Jack McGrath, however, loves bearing witness to unbridled self-expression, whether it be rollerblading through office halls or building a “nerd cave” in a spare conference room. When coworkers get weird, Jack feels at home. Is this because Jack grew up in an unstructured environment? Yes and no. Did Jack grow up in a restrictive classic upbringing? Yes and no.
If it’s not clear already, Jack grew up in two worlds: one with complete freedom to be curious about the world and another where that freedom was restricted. The struggle between Jack’s autonomy and his constraints means that today Jack values and looks up to people who are unapologetically themselves in any context.
“If I can achieve some portion of that competence, while also expressing myself however I like, I feel like that’s a great place to be in life. I appreciate that kind of unbounded expression in others.”
Growing up, Jack describes his upbringing as being a traditional one. Jack’s education (at least for his elementary school years) was not traditional by any measure, though. This difference between his home-life and school environment meant that young Jack often had a hybridized sense of life’s possibilities.
When we ask what Jack wanted to be as a kid, he produces the immediate yet completely unique answer, “I wanted to be a missionary to Mars. I was convinced that there were aliens on Mars and I wanted to convert them. Also, a Lego designer. So, pretty standard.”
[IMG: Young Jack.]
Jack becomes wistful when he recalls his early school days. He paints a picture of an elementary school where kids were allowed to largely direct their own learning experience, which helped him grasp interests he may not have otherwise encountered at home. From creative subjects like woodworking and painting to rugby and paintball, young Jack was free to pick up any interest or book that struck his fancy. It was here that Jack first picked up Douglas Adams’ book The Hitchhiker’s Guide to the Galaxy, a book he hid under his mattress while at home.
“I gained the ability to decide what I want to do and to pursue interests, whether they conform to convention or not. There was very little control, a lot of chaos, but everyone had a good time.”
But this free-play fantasy education couldn’t last forever. When Jack’s mother realized that his school considered donut eating contests an “extreme sport” Jack’s parents reconsidered their decision to give their children a free-form education. After “the donut incident” Jack and his brother were enrolled in a stricter school that enforced classical religious education. A move Jack characterizes as a bit of an overcorrection, even if he understands their reasoning.
Jack’s new school was about as different from his old school as you can get. “It was very ‘by the books’. Everything you could imagine about a southern Christian private school, it was.” Even though his new school placed restrictions on Jack that felt uncomfortable given his previous freedom, there was still some value in the added structure. “It reinforced good things as well. It taught me how to write really well. They really emphasized good prose and all the things that make people decent writers.”
For Jack, exploring literature and writing was a productive use of the structured environment that he was now experiencing at school. He didn’t agree with everything that was being taught, but Jack wasn’t about to stage a protest about it. Instead, Jack quietly spent his time delving the internet for like-minded friends who he could collaborate with. “It really got me online. Basically I was spending much of my time on the internet from the age of thirteen through the rest of my high school years.”
[IMG: Jack @ Telluride camp.]
Discovering online friendships from across the world inspired Jack to seek out a Telluride Association summer program for high school students, a program that brings together students from all over the world. Even though Jack doesn’t characterize himself as the best student all-around, he pulled together all his resources to attend the summer-camp.
“It was a real pinprick to that bubble I was in, in the southern US. I was living with thirty-two teenagers from the summer who were from all over the world. That, I think, was a bigger turning point than anything else.”
After this experience, Jack was inspired to go to college, a move he didn’t consider as seriously before. After getting into the University of North Carolina against the odds, Jack went into exploration mode. Jack wanted to interact with intelligent, creative people who grew up with a different life experience than his own. Again, Jack felt himself surrounded by the types of people he sought and he took full advantage of the experience.
At school Jack joined multiple groups, including (briefly) an anarchist group, a computer science club and multiple internships beginning in his Freshman year. For Jack, his exploration of college was more about the people and experiences than anything else. Jack soaked up different ideologies, groups and opportunities including a chance to intern at AirBnB, where he was charmed by the tech environment and culture.
“It was awesome to be in San Francisco at that age and see all the different ways of living there.”
As Jack continued to immerse himself in new environments, however, he was noticing that he wasn’t feeling too great. His lack of energy throughout college ended up being an illness that forced him out of college temporarily. While Jack continued internships for a time, eventually he had to pause all work in order to get a liver transplant. After finishing up his degree in 2019, though, Jack knew exactly what kind of environment he wanted to work in.
Since his early internships at AirBnB, Jack observed growth and how it affects companies. It was there that Jack realized this, he wanted to work at a small start up. After taking his time to look for opportunities that suited his needs, Jack was approached by a Telluride Association connection about joining a small startup called Posh Technologies. Right away Jack felt like Posh was the right fit, not only because the ideas behind it were solid, but also because the Telluride connection convinced Jack that the culture at Posh would deliver. “Posh was everything I was looking for since hearing that I should be at a small company back in 2014.”
[IMG: Jack recent.]
Jack, of course, wanted to be around lots of people who were unique, talented and friendly, but he also appreciated a smaller atmosphere where collaboration was encouraged. After signing on, Jack felt welcomed by his colleagues. “I’ve never been made to feel like I’ve asked a dumb question, or never been made to feel like I was imposing on someone by asking to collaborate. It’s a very collaborative environment.”
And finally, perhaps most importantly, Jack finds himself in an environment where he doesn’t have to be all too serious. Jack could reasonably create a presentation about his lifelong love for Garfield (and consequent hatred of Mondays), for example, and not be judged a bit by colleagues who have their own interests and obsessions to share. “Interacting with the people here at Posh, nothing feels like drudgery. We’re all working on this really, really cool project together.”