In this episode of LATE BLOOMERS, Rich and Rox dive into the biggest flops, failures, and f*ck-ups of their lives — the ones that embarrassed them, humbled them, shaped them, and ultimately set them on the path they’re on today.

Rich talks about giving up a near-pro golf trajectory at 15, two divorces by 32, and the gambling addiction that wiped out everything he had — and the gratitude and perspective that came on the other side of it. Rox shares the pain of taking down her first single after it “flopped,” the unopened post, the money chaos, and the shame stories she carried for years before learning to ask for help.

Together they explore how these moments cracked them open, forced accountability, and led to therapy, sobriety, self-awareness, and the life they’re living now.

It’s honest, hilarious, and painfully relatable — a reminder that everyone’s got failures, but it’s what you do with them that turns your life around.