At 14, a garage band from a neighboring high school needed a drummer. Ryan had a basic black TKO kit, a Discman, and a copy of The Verve Pipe's Villains — he taught himself to play by ear. That band went on to do genuinely impressive things over the next five years, with Ryan running the business side and discovering a knack for finding and developing talent.

He became a talent buyer at venues across southern Michigan, booking and promoting national touring acts — Sponge, The Verve Pipe, Seven Mary Three, Days of the New, Finger Eleven, Buckcherry, Chevelle, Crossfade — learning promotion, support-act vetting, and the psychology of a live show from the inside.

When a sound engineer cancelled with an hour's notice, Ryan got behind the board himself and made the show happen — sparking a move into full tip-to-tail event production, for acts that included Aretha Franklin's son and Sting's son's band, Fiction Plane.

As drummer and manager of Darling Down, Ryan secured endorsement deals with PRS Guitars, GHS Strings, and dDrum — plus guest spots from members of Dark New Day, Sevendust, Taproot, and Sponge, and sync placements on MTV, Discovery, NASCAR, and NHL.

When the band ended in 2018, he founded Hudson Entertainment, LLC and, with a former bandmate, launched 1887 Media in 2019 — bringing full production, video, and promotion to artists who need it most.