Zach Both was living in Boston and working as an art director for a 3D printing start-up when the road beckoned. He felt restless behind a desk. He had wanted to be a filmmaker since age 9. He knew he needed to take a creative risk. Then he watched a video of Alex Honnold, the free-solo rock climber, who lives in a customized van and travels from mountain to mountain.

Mr. Both, 23, decided to embark on what he called “a cool creative roadshow”: traveling the country and collaborating with local artists on short films. In late 2014, he paid $3,900 for a white 2003 Chevrolet Express van with 200,000 miles. With a Dwell-inspired sense of design and help from his father, he made it a rad home on wheels.