From Homeless to CEO, Is It All a Con?

By Kyle Kesterson, CEO of Freak'n Genius

I could begin by promoting myself and boasting a list of personal and professional accomplishments made, especially over the last few years as an entrepreneur, but would risk having you click away before getting to the end... because we both know that you've heard it all before.

Instead, I would like to confess that I may be a fraud. You see, I'm not supposed to be here... or so I was made to believe while growing up.

Starting from the ground floor

I was born into an environment that crushed and suffocated almost everything in it. So, when I was a child, my family risked everything to move from "the worst place to live in the United States" to start a new life in Seattle.

My parents each worked 2-3 jobs just to keep the family alive, and living paycheck to paycheck took its toll on our family cohesion. Their jobs were still not enough and we soon found ourselves homeless. For many months we lived in various homeless shelters until we were finally accepted into a transitional housing program. Our basic needs were met through the use of food and clothing banks. Nothing like a stale sugar cookie and a god-knows-what-stained stuffed rabbit to get your spirits up!

A repeat failure

School was stifling, and I was well aware that I was different from the other kids in Redmond, home to Microsoft. I lived at the Y.W.C.A., wore tattered clothes that were too large for me, and used food stamps for school lunches. They lived in large houses, wore logo-emblazoned clothes, and had pagers. It was during the 4th grade that my class participation dwindled. My defiance of authority began to grow and I began to be labeled as an outcast. I was also severely bullied. Ever have a cafeteria trash can dumped all over you because your dangerous prank led to evacuating the whole wing of a building? Not pretty.

During the course of my life I have attended 14 different schools, and I've either failed or dropped out of most. When dropping out of high school with close to the lowest G.P.A. possible, and one of the largest disciplinary files in the district, teachers and peers told me, "Kyle, by the time you're 20 you will either be dead, in jail, or flipping burgers."

It seemed I was diminished by everyone in my life. They all gave up on me and let me disappear. That is, except for my parents, and a Microsoft Software Engineer named Jason who introduced me to technology. They kept reassuring me that I was meant for much greater things, and if I was willing to work hard and go through what it took to succeed, I could accomplish anything and I deserved everything the world had to offer.

At the time, their encouragement wasn't enough and I spiralled deep into depression and isolation.

Freedom in expression

It was only art in which I felt warmth... it seemed to catch all my suffering. Artist Alex Pardee spoke to me. His work was dark, but I felt it... and I needed to feel something to make me still feel human. I must have copied almost every sketch and painting that Alex had created. He became my mentor, and he didn't even know it.

I clawed my way out of my emotional pit by teaching myself how to draw, paint, craft, and build. I started to feel empowered to make a difference, first in myself, then my environment... followed by the people in that environment. I became so hungry to be a part of something that mattered.

As my appetite for creating impact grew, I became aware of opportunities around me. Instead of letting them slip by like I had done so many times in my past, I started to ask questions and explore the possibilities.

Validation inspires

It was then that I was welcomed into a vibrant, online, creative collective called TheRoot42. It is a digital environment that encourages growth, collaboration, and community. Over a decade together now, we have invisible tattoos and secret handshakes...

Their support and feedback provided me enough confidence to submit my portfolio to
Cornish College of the Arts... and I was accepted! The selection committee was enthusiastic and gave me a substantial scholarship. I was doing flips inside, never before had I been so validated!

At Cornish, I soon found myself to be an outcast among outcasts. Many of my "free-thinking" peers came from wealthy families and had chosen Design because it was trendy... and it seemed they had little to no conviction in their work. I was there because I had to create, and I was working full time as a janitor to support myself. Janitor life is a whole other juicy blog post...

Getting into a plastic rocket

Leaving college early, I began working as many creative jobs simultaneously as I could. However it was when I caught the eye of the Creative Director at Funko, who believed in my creativity and went out of his way to bring me on as a Toy Developer, that I dropped everything to pursue it. Working with the world's largest licenses on virtually every cartoon character I could think of and more, to create toys, electronics, and packaging, as well as being mentored by two of the most prolific artists I had ever encountered.

And yet, I still couldn't fit in.

I attempted to make Funko a part of my identity, and brought it with me into the world in every way I could think of. However, not only was my enthusiasm not being nurtured by the company, it created friction. I realized that the environment and culture did not lend itself for growth, at least my kind. The toys lost their magic, and just became insignificant plastic. It started to show in my work, and I would even occasionally fall asleep at my desk. I knew I wanted to quit, but before I could, I was fired for not "kicking ass".

It was demoralizing, but on the drive home I felt an incredible weight lifting, and I remember thinking "this is either going to be the worst thing, or the best thing that has ever happened to me."

Blast off

The same afternoon that this new freedom was thrust upon me, I got a call from one of my best friends. He was adamant I should check out an event called Startup Weekend.

My parents always told me I would create my place in the world. They assured me I would fit somewhere. Startup Weekend was this place. Outcasts, weirdos, and extremely talented people came together to kick ass. No one wanted to me to "fit in". In fact people were excited about how weird I was. For the first time in my life I was confronted with a truly, unabashedly blank canvas. A place to create and wonderful people to create with.

Over the last three years, I have put the metaphorical brush to this canvas. I have surrounded myself in a community of people who believe in me, and was given the opportunity to take two startups through TechStars, which gave me direct access to dozens of entrepreneurs, investors, and media. Life changing mentors like Andy Sack (TechStars/Founders Co-Op), Greg Gottesman (Madrona Venture Group), Marc Nager (Startup Weekend), and so many more have provided countless hours of feedback and guidance on building products, hiring and forming teams, conflict/resolution, fundraising, negotiations, and other valuable life lessons.

The people in this ecosystem care deeply about each other, the world we live in, and the world we work to create. I believe we can change the world and these people don't think I am crazy or delusional. Well, they may think I'm crazy, but not because of my belief and ambitions.

Hearing the character-building stories of CEOs like T.A. McCann, (Gist), Ben Huh (Cheezburger Network), Dan Shapiro (SparkBuy), Rand Fishkin (SEO Moz), Keith Smith (Big Door) and so many other great leaders, makes me optimistic that my formative years of sailing rough seas, will serve as an advantage with leading my team through the wild adventures yet to come.

Destination: Cloud 9

There isn't a day that passes where I'm not moved by the appreciation I have for who I'm working with, what we're working on, and the environment we get to work in. Despite facing the issues and hurdles that every startup is met with, we have become a highly functional and effective band of misfits that is fueled to succeed in building this business, by creativity, collaboration, making something that matters, and having a hell of a lot of fun in the process.

It's the momentum built from this team, my family, and the startup community that hushes the whispering voices telling me, "you are just the homeless, high school dropout, janitor kid that was supposed to end up dead, in jail, or flipping burgers."

Kyle Kesterson is a serial entrepreneur and most recently co-founded
Their current product is YAKiT, a mobile app that makes you the funniest person you know.
You can follow him on Twitter @kylekesterson, or Freak'n Genius on Facebook.