How Authentic Stories Turn Trust Into Revenue | Storyselling with Kendall Cherry

In this episode, Michelle Terpstra sits down with storytelling and sales strategist Kendall Cherry for a conversation about content, trust, and conversion. Together, they explore why selling with storytelling consistently outperforms traditional testimonials and case studies and why buyer psychology assures us that no amount of AI-generated copy can replace lived experience. Kendall breaks down how authentic stories build authority, attract aligned buyers, and create sustainable revenue without relying on pressure or hype.

Kendall and Michelle workshop a real-world client scenario to demonstrate how one story can become a powerful sales asset. This episode highlights personal growth, leadership, and revenue strategy in a way that feels grounded and immediately actionable. It’s a reminder that the stories you are most hesitant to share are often the very ones that move you forward.

Chapters
[Start] Why Story Selling Beats Traditional Sales Copy: Michelle and Kendall unpack why stories convert more effectively than other content forms.
15:24 The Two Audiences: Kendall introduces two audience types: the “DIY never-buyer” and the high-value long-term lurker.
22:50 Workshopping a Real Client Case Study: A breakdown of how one operational win can turn into multiple high-impact sales assets.
31:27 Turning Results Into Revenue Content: How to structure case studies that shorten sales cycles and help sell on your behalf.
43:13 Teaching Story Selling at Scale: Kendall shares why she built The Greenhouse and how founders can learn to write high-converting stories themselves.

Links & Resources

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