FEATURED EPISODE

He’s going to prison in just days… Illegal bookmaker, jiu-jitsu dad, and unapologetic high-rolling gambler, Matt Bowyer pulls back the curtain on million-dollar Mondays, counting cards, and the FBI raid that upended his life. He talks losses, trolls, restitution, and why he’s turning chaos into purpose with his new book Recalibrate, a documentary, and motivational speaking. All while preparing for his prison sentence and focusing on family, mindset, and a legal comeback.

Designer, musician, and community-radio music director, Jeff Holmes, joins the show to talk creative process, analog style, travel, and the surprising ways ideas find you. We also dig into vinyl reissues, theme-music-making, and why he built a life that leaves space to think.

A five-year van trip turned global creative lens: Oakley’s Jes Stockhausen shares how nomadic filmmaking, a Patagonian rescue dog, and a passion for the circular economy shaped his work… from surf helmets to an Oakley visor headed to the moon.

Oakley’s VP of Soul & Creative Brian Takumi joins Shady Characters to trace 28 years shaping the brand—from BMX roots to the iconic Square O, from wild Foothill Ranch culture to leading creative in a 200k-person matrix. He unpacks storytelling, “physics elevated to an art form,” and why AI is a tool—not the soul—of design.

Filmmaker Chris Stacey joins Shady Characters to share his journey from music videos and viral hits like Teach Me How to Duffy to feature films including The Blind. From selling his guitar to pay rent to seeing his work on thousands of theater screens, Chris talks legacy, creativity, and why saying “yes” shaped his career.

Megz and Katie, the duo behind Intertwined Inc., share their journey from startup to a leading hospitality company. Known for projects like RAD Camp, they highlight their commitment to people with special needs while intertwining inclusivity for women in their business, blending humor, heart, and community impact in their work.

James and Marie Kelly share their journey from a nomadic childhood and lifelong love of dance to forming Bootleggers, a music and line dance group. From opening for Clint Black to supporting veterans, they’ve built careers rooted in passion, family, and giving back.

Tim DeBrincat and Evan Burgher of Thatch Creative join Tom Dioro to share their evolution from a small production shop to a full-service agency. They discuss storytelling, the creation of Shady Characters, and how family life inspires their creativity while keeping a personal touch in their work.