Kevin Rogers on Closing CopyChief, Ending a 25-Year Marriage, and Starting Over at 55

18 Feb 2026 · 54 min
54:03

In this Sacred Business Stories Substack Live interview, host Phil Powis and co‑host Carolina sit down with Kevin Rogers, the founder of CopyChief, to trace his unconventional career path, the rise and fall of his community‑focused copywriting business, and his current personal and professional transition. Kevin recounts starting as a stand‑up comedian, moving into direct‑response copywriting, and launching CopyChief in 2014 as a curated community for freelance copywriters. Over eleven years the community grew to host live events that attracted 150‑300 attendees from around the world, fostering a culture Kevin likens to raising a child. He describes how burnout, the increasing mechanisation of copywriting by AI, and a feeling that the business had become a machine led him to cease new client work and eventually close CopyChief in December. Simultaneously, Kevin underwent a profound personal mid‑life “middle passage,” ending a 25‑year marriage and confronting questions of identity, which he frames as moving from a first adulthood to a second adulthood. He reflects on the tension between visionary‑integrator models (EOS) and his own need to stay creatively involved, acknowledging that scaling a business often conflicts with his creative DNA. Looking forward, Kevin is launching a Substack‑based podcast, “Paid to Create,” interviewing creators across industries, and commits to a disciplined publishing schedule before his 56th birthday. Throughout the conversation he shares practical advice on pausing, confronting burnout, writing down what brings joy, and using accountability partners to overcome fear. The dialogue emphasizes authenticity, the importance of aligning business with personal truth, and the ongoing process of reinventing oneself.

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