In search of his next work challenge and life adventure, Kyle Kesterson has decided that there really should be no distinction between those two things.
So when the former Seattle startup veteran and serial entrepreneur started to wrap his head around what he wanted to do next, he didn’t just update his LinkedIn, or ping friends via email with a copy of his resume. He built a website called Get Your Own Kyle, and invited people to tell him where he should go, what he should do and why he should do it.
He even mentioned Amazon’s search for a second headquarters as a bit of inspiration for the tactic.
Kesterson, 33, left Seattle in the summer of 2014 to move his animation startup Freak’n Genius (later Campfire) to Las Vegas after getting funding from VegasTechFund, and to join a community there that was working on revitalizing downtown Las Vegas.
Kesterson said that just a couple weeks after getting to Vegas, a reorganization “implosion” at the Downtown Project made it an awkward time to be coming aboard. So he decided to go on a little road trip with his dog, Bean.
“I really started to get into a rhythm of working behind a laptop on the road,” Kesterson said during a phone interview with GeekWire. “I had a lease on this house in Vegas, so I’d come back to the house every three or four months and change out my gear as the season was changing and then I’d head back out on the road. The road trip turned into about two years.”
Every time Kesterson returned to the house, he was hit with a nagging question: Why do I own all this stuff?
He started digging into the bigger question of where the need comes from to accumulate. And while circling that rabbit hole, he asked himself yet another question: What do I define as success?
“It seems like an obvious question, but it really felt like one I had never put in front of me in this way,” Kesterson said. “It started to make me realize that all of these definitions swirled around collectively from my parents, through my peers, throughout culture, and it never really was clear for me. I started seeing this idea of success as a box on top of a mountaintop somewhere labeled ‘success,’ and if I work hard enough I’ll achieve it someday.”
Kesterson sought to determine — through a process he calls looking backwards — when in his life he has felt the most alive, excited, fulfilled, creative and connected.
“Reliving those memories I unearthed a number of themes and those themes had nothing to do with stuff or status or class, so I reordered my life to achieve the little principles — and the van became the vehicle to it.”
Kesterson did about 90,000 miles around North America, stretching from a quadrant that had Banff, Alberta, and Whistler, B.C., at the top and Baja, Mexico, and Austin, Texas, at the bottom.
During that time he took on a couple interesting clients, including the digital entertainment company JibJab. He knew co-founder and CEO Greg Spiridellis, who told Kesterson he didn’t have anything specific idea for him in mind, but invited him to come in and create an idea and a team and build a product.
They ended up creating animated talking emojis built seamlessly within messaging. Kesterson called the product “hilarious, very effective, and first of its kind.” But he said they couldn’t get it approved by Apple for broader App Store distribution, and nine months later Apple launched talking emojis in their OS update.
Kesterson was also invited by Winnebago, the makers of recreational vehicles, to be the creative voice behind a new product aimed at an entirely new demographic in which the company wanted to basically take RV’ing off road. (You can see him in the promotional video below).
If you’re familiar with the popular social media movement around #VanLife — minimalism, less is more, and how access to nature unlocks a sense of identity — picture Kesterson’s storytelling and photographic work being put to use. Winnebago sought to channel that, and basically gave Kesterson the keys to building “a whole arsenal of content.”
“They didn’t even see what we put together until launch day,” Kesterson said. “It was ballsy, but we were living it, breathing it and we built a team and we built the story, we built the execution, we launched the thing and it was very loud. They went from, ‘Can we sell 300 of these vehicles in a year?’ to ‘Oh, crap, it’s been three weeks and we’re sold out.'”
Kesterson called himself “a glorified car salesman” at the end of the day, but he found comfort in his appreciation for where people would be getting with the vehicle that he was creating a story around.
The sense of adventure and the success that was born out of his initial travels fueled further travel for Kesterson. His Instagram feed is a chronicle of beautiful people and places. And along the way he has chucked the popular notion of “work/life balance” and gravitated toward what he calls “work/life mesh.”
“Work/Life balance means work and life sit diametrically opposed on opposite ends of a balancing scale,” Kesterson wrote on an Instagram photo showing him sitting with his dog in the mountains of Colorado. “If I can do one thing long enough or well enough, I can have these other moments for life. Mesh is having found work that requires me to live life, and by living life, I’m feeding myself. I don’t know how long I can keep it up, but it’s the success I’m striving for.”
Kesterson credits his past work at Startup Week and TechStars and Giant Thinkwell (which became Haiku Deck) with creating an atmosphere in which people came looking for him when they had a specific project that they thought he’d be great for. So this time around, Kesterson created the new website to let people know that there is space and opportunity, and he’s ready to see what the world can bring in.
The site says he’s looking for a place, anywhere in the world, to call home base for the next three to 36 months or so. He wants to experience community, because in traveling he’s come to have a greater understanding of the fine line between alone and lonely. He’s looking for a project that taps into his expertise in storytelling and building and launching products. And he’s in search of a location that stirs his creative energy.
“I put that together while I was just in Ecuador the other day,” Kesterson said of the site, and a recent three-week trip. “I put it out there and already have 13 opportunities that scatter the globe. So now it’s sifting through and seeing where it takes me.”
Those who click on a link which asks “Where should I move?” are greeted with a form that says, “Thank you for exploring this weird experiment and helping design the next chapter of my life!” Kesterson then asks a bunch of questions, including some looking for details about the location — Describe what makes it so amazing — and others seeking details on the project — What’s the vision? Why does it matter?
Locations of offers he has received so far include Canada, Colorado, San Francisco, New York City, Scotland, Dubai and other Middle East cities, Netherlands, London, France, a series of sea ports, a nomadic caravan, and the option to work remotely.
Projects range from revolutionizing the media industry, providing affordable healthcare to everyone on earth, creating a network of micro-climate and logging tools, women’s periods (menstruation), rethinking education, humanity-driven innovation, blockchain education, new media storytelling for kids and more.
One intriguing offer came in from a woman whose father was a “real life Indiana Jones,” according to Kesterson, and she’s looking for someone to help her with a multi-million-dollar project in which she’s creating an interactive art piece and awareness campaign to help protect ancient caves in Ecuador and the Galapagos Islands.
The path Kesterson has taken and the process that he’s attracted to now appear to make it unlikely that a giant tech company — even one in Seattle where he spent so many years — could end up being an attractive option.
“I think ‘what is tech trying to serve?’ is my number one question,” he said. “If there’s one thing that I have lost all of the luster for is that tech for tech’s sake is sexy. It’s not. I think the culture of startup has become unhealthy. Having stepped away from it, I just see it more clearly.
“I just really want to work backwards from, ‘Why does this need to exist? How is this making an individual life better? How is this making a community better? How is this cleaning up the planet?’ Stuff that I think is significant and relevant more than ever.”
Kesterson also has an opinion about Instagram, the social media app on which he’s attracted more than 11,000 followers with his 2,300 posts. Add him to the list of those annoyed by the Facebook-owned platform’s changes to its algorithm. Like many, he’s been looking at Vero.
“You know you’re doing something wrong when everybody you talk to cannot wait for the next thing to replace you,” he said of Instagram. “That is not sustainable.”
Kesterson leaves Tuesday for a trip that will take him to Italy, Spain, Portugal, France and Israel. He has no plan for that trip in regard to where he’s staying. He said he’ll figure it out when he gets there.
As for his greater life plan, he said he’s prepared for anything there, too. He hopes to be on solid footing by June or July.
“Life is gonna happen down any path that I choose,” Kesterson said. “I’m gonna learn things, I’m gonna succeed, I’m gonna fail. There truly is no right or wrong answer.”
