From dying and coming back to life at 12,000ft up in the mountains, to being stranded in 115º deserts, falling down frozen waterfalls in canyons, being sensory-deprived in caves, or stepping into the lives and homes of colorful characters scattered across the globe, "I wonder where this road goes..." is more often than not, the prompt that begins most of Kyle's stories and [mis]adventures.

Kyle, and his faithful-but-fiercely-independent Border Terrier, Bean, have been on the road full time as #vanlife nomads for the past 3 years. As a self-ascribed Fear Slayer, Kyle's definition for ultimate personal success, is that as he's looking back on his life, just before drawing his last breath, FEAR did not prevent living life, in even the subtlest way. 

This unfolding journey has Kyle scratching at deep questions of what it means to be human, what it means to be alive, and how to remove the barriers that hold us back from living our greatest lives.

Always armed with a camera, pen, and unquenchable curiosity, Kyle lives to explore, create, and connect. 

But really... he's just trying to be as huggable as Bean.

Follow their ongoing adventure on Instagram at @KyleKesterson or send an email to get in touch.


Growing up, Kyle and his family hit the lowest of lows moving in and out of homeless shelters and standing in line at food and clothing banks. It led to frequently moving, attending 14 different schools, becoming one of the worst kids in the school district and finally dropping out after being told by teachers that he'll "most likely end up flipping burgers, in jail, or dead."

Discovering art and creative expression saved his life and put him on a path towards carving his own path and ultimately creating positive impact around him.

Most of Kyle's work is focused around youth, poverty, creativity, community, inspiration, and entrepreneurship. He is the Founder and Chief Freak of Freak'n Genius, is a 2x TechStars alum, Startup Weekend Global Facilitator, and was the Co-Founder and Chief Creative Officer of Haiku Deck. 

Kyle has spoken at TEDxSeattle, Ignite, Steve Jobs legacy conference - DENT the Future, Spark Bootcamp, and Consero's Startup Acceleration Forum. He coaches and mentors youth and early stage founders through Startup NEXT, TechStars, Startup Weekend, StudentRND, Girls Who Code, and YouthCare.

He expresses himself creatively as an artist, illustrator, designer, animator, toy developer and photographer. Kyle is also the Vice Curator of the World Economic Forum's Global Shaper initiative in Seattle, and member of the Young Entrepreneur Council, Young Entrepreneur Social, and Sandbox HQ - all global communities of 'Young Change-Makers'.

Bentley Bean is Kyle's best friend and side kick. He's an 8 1/2 year Border Terrier, is trained as a US Service Animal, and really who is responsible for running the show.


Have ideas, thoughts, crits, or questions? Drop Kyle a line!

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