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

18 Feb 2026 · 54 min
54:10

In this Substack Live interview, host Phil Powis (joined by co‑host Carolina) talks with Kevin Rogers, the founder of CopyChief, about his unconventional career path, the rise and fall of his community‑based copywriting business, and the personal upheavals that led him to close it. Kevin recounts his early years as a stand‑up comedian, his transition to direct‑response copywriting, and how he built CopyChief into a 11‑year‑old ecosystem of freelancers, live events, and $25 million in contracts. He uses the metaphor of a child to describe the community’s growth and later its loss of personal ownership. The conversation moves into the “middle passage” – a psychological mid‑life crisis described by Dr. James Hollis – which for Kevin manifested as the end of a 25‑year marriage, burnout, and a loss of creative joy. He explains how AI’s rise reduced demand for freelance copywriters, prompting him to stop taking new clients and eventually shut down CopyChief. Kevin shares his current transition: a Substack show (“Man in the Middle”), a new podcast/ newsletter project called “Paid to Create,” and his intention to launch the first episode before his 56th birthday. He discusses fear, the need for pause, practices for staying accountable, and advice for creators feeling stuck. The interview ends with a commitment to check‑in on his progress and a call for listeners to write down what they love about their work and prioritize it.

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