From Dropout to C-Suite

UPDATED: April 6, 2023
PUBLISHED: October 12, 2014
Kyle Kesterson

Kyle Kesterson has been a driving force behind several technology startups, but in high school his attitude and performance were so poor that a teacher told him by age 20, he’d “either be dead, in jail or flipping burgers,” according to a HuffPost story by Kesterson. During his formative years, he’d been homeless, lived off food stamps, attended 14 schools and was tormented by bullies. He dropped out of school in 10th grade.

That’s hardly the upbringing one expects from someone as enterprising and successful as Kesterson. Prior to his current chief operating officer role at OPTIMAL XR, Kesterson was founder and chief storyteller at Seattle-based tech firm Freak’n Genius (now known as Campfire), which created the popular YAKiT mobile apps that turned everyday photos into hilarious animated videos. Before that, he helped found Giant Thinkwell, another software venture based in the thriving Seattle tech hub. For Kesterson, the road to the promised land may have been paved with potholes, but in many ways those struggles helped him get where he was going.

“I was the poorest kid, not to mention the smallest kid, and soon thereafter, just the worst kid in school, from my attitude to my grades,” Kesterson said of his early life. “There was always a feeling of not being good enough. There was constant self-doubt. But out of that, I learned to live with less, to appreciate the smallest things, to be resourceful, resilient, scrappy. Not having money to throw at problems, it meant having to rely on creativity to find opportunities.”

How Kyle Kesterson discovered a passion for creativity

That creativity turned out to be the key to unlocking his future. He discovered an interest in art (from sketching to sculpting) and design. “I got into it because it made me feel something,” he recalled. “[Before] I was in a dark place; I felt numb and negative. When I tried art, I was like, Wow, this is really cool. Art gave me something clear to put my energy toward.”

Kesterson said his early artistic efforts weren’t very good, but they were incredibly fulfilling. Then people started to respond to his artwork. He said he hadn’t really felt that respect before, and the validation provided the fuel for him to continue learning, at which point Kesterson applied to the Cornish College of the Arts in Seattle.

Before that, he was self-taught and didn’t understand the fundamentals of art. But he clearly showed promise: When his instructors saw his work, they suggested Kesterson skip his first year and move immediately into second-year coursework. He told them no, saying he “wanted to start at the beginning and learn the tools.”

Ultimately he became disenchanted with pursuing art and design as a career. “I was doing the thing I loved and was passionate about, but I learned pretty quickly that even people going to a liberal arts school weren’t there for the same reasons I was. They were excited to get a big paycheck, because design was starting to become very trendy. It wasn’t passion-driven. So socially I didn’t really fit in with most of the people there,” he said.

Entering the startup world

After two years, Kesterson left Cornish and worked whatever creative jobs he could, still searching for that ideal outlet. In one misfire, he was a toy developer at the Funko toy company, where he had a hard time fitting in. When his enthusiasm wavered and he stopped putting in the same amount of effort, he was fired. At that point, a friend encouraged him to attend Startup Weekend, where he rubbed elbows with local entrepreneurs, investors and business leaders.

His foray into startups had begun. Kesterson’s first new enterprise was Giant Thinkwell, co-founded with Kevin Leneway and Adam Tratt. The partnership, however, was fairly short-lived.

“We didn’t know what we were doing,” Kesterson said. “We realized really quickly that we built the wrong thing for the wrong audience at the wrong time. That harsh realization would leave us asking, ‘What next?’ And we’re spending our investors’ money figuring it out. [During Kesterson’s tenure, the company created Mix-N-Match, a ‘celebrity-based’ Facebook game, and FlickMob, a social media site where people would watch and rate YouTube videos; neither is still around.]

“There was just so much pressure amongst these product failures that contention within the team built up, and we didn’t have systems in place to solve our huge communication issues…. We were responding to each other emotionally. It just came down to an implosion within the team, and somebody had to go. And it was me….

“It was terrifying, because that was the first thing I had ever done as a creative person where it really started to gain momentum. That brand was an extension of me. When I left, people were like, ‘That was you.’ I had controlled the tone and the voice, what people experienced. And when I left, it was like, Oh my God, a piece of me just died.

Early experiences’ impact on Kyle Kesterson’s resilience

Kesterson’s fears eased quickly, though: As soon as a blog post went up about his departure from Giant Thinkwell, emails crammed his inbox, and his phone rang steadily. “People reached out. People wanted to work with me. Freak’n Genius was born in that first week of meeting after meeting,” he said.

During Kesterson’s tenure with Freak’n Genius (he left in 2018), the company graduated from the Microsoft Kinect Accelerator in 2012 and participated in the International Consumer Electronics Show in January 2014. When the company’s YAKiT Kids app was released early in 2014, it quickly shot up the ranks to become the No. 1 free kids’ app in the iPhone app store. 

Even in 2014, Kesterson—only about a decade past his homeless days—had no intention of panicking if Freak’n Genius steered off course or sunk altogether. He had experienced rock-bottom. “Sure, if it fails, that’s gonna suck, and we’d have a huge ego bruise. I’ve already embraced fear as a driver. Because no matter what, I’m not going to be sleeping under a bridge. I’ve built a community of people who support me. There’s a net underneath me,” he said.

This article was published in October 2014 and has been updated. Photo courtesy of Kyle Kesterson.