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Freelance to Founder

Freelance to Founder

Will AI Replace You?

Freelance to Founder · Nov 9, 2026 · 32:26

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Kendall Cherry walked out of a Fortune 100 C-suite ghostwriting job with $10,000 in savings and built a multi-six-figure ghostwriting business from scratch. Now, with AI pumping out more content than ever, she's seeing something most people wouldn't predict: demand for premium, human-written sales copy is climbing. Preston calls an audible on this episode and puts his own question to Kendall: what does AI really mean for the future of writing careers? They dig into "lowest common denominator messaging," why editing an AI draft can take an expert twice as long as writing from scratch, how Kendall tackles the AI question head-on in her sales process, and why people's craving for real, human connection isn't going anywhere.


Support our show sponsors → https://freelancetofounder.com/sponsors


Submit your own question → https://freelancetofounder.com/ask


Kendall Cherry → https://kendallcherry.com


Here to Sell (Kendall's book) → https://www.heretosellbook.com


Kendall Cherry on LinkedIn → https://www.linkedin.com/in/kendall-cherry/
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Episodes: Freelance to Founder

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