Will Day, Contemporary Boulder-based Artist

In this episode of The Bear Roars, Dan sits down with Boulder artist Will Day, whose unlikely path from architecture to painting began in the middle of the 2008 financial collapse.

Will talks about losing his job, moving his family to Boulder, and slowly building an art practice from a basement with no roadmap and no guarantee it would work. He shares the early challenges—financial strain, uncertainty at home, and the pressure of trying to build a creative career while raising two young kids.

Dan and Will discuss how Boulder shaped his development as an artist, why Black Lab Studios became the right environment for his work, and what it means to create during times of disruption. Will breaks down his process of painting on raw canvas, working across multiple pieces at once, and allowing intuition rather than rigid planning to guide each piece.

The conversation also touches on Boulder’s evolving arts scene, the impact of events like the Sundance Film Festival and Boulder Roots Music Fest, and the role of community in helping local artists gain visibility.

Learn more about Will’s work: https://www.willdayart.com

Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book

Listen to Dan's Song Stretch: https://distrokid.com/hyperfollow/dancaruso/stretch

Check out music by Jason Mendelson (Jace Allen): https://www.youtube.com/@jaceallen

To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com