Kendall Cherry, ghostwriter for multi-million dollar startups, shares transformative insights on overcoming the fear of selling through authentic storytelling, addressing the guilt that keeps many entrepreneurs from effectively marketing their services.
At the heart of our conversation is a truth many of us feel but rarely say: selling your services often brings guilt. Kendall calls out the “starving artist narrative” that convinces creatives they shouldn’t make money doing what they love. But selling isn’t selfish—it’s a service. And when you lead with your story, your values, and a clear vision for your clients, marketing becomes not just easier, but joyful.
Selling Strategies Rooted in Story
Kendall introduces practical, story-driven techniques to help reframe how we think about sales. She suggests taking “sales field trips”—watching how businesses naturally weave selling into their everyday customer experience. It’s a reminder that good selling isn’t pushy; it’s intentional and supportive.
She also shares powerful language shifts, like speaking directly to your audience using “you” instead of distancing phrases like “we.” This simple tweak helps potential clients feel seen and spoken to, building trust from the first sentence.
One of Kendall’s signature strategies is “future casting”: using storytelling to help clients envision what their life or business could look like after working with you. Instead of listing features or deliverables, paint a picture of transformation. That’s what people really want to buy.
Building a Sales Ecosystem that Feels Natural
If constant discovery calls aren’t your thing, Kendall has good news. She explains how to build a content ecosystem that does the heavy lifting for you—educating, qualifying, and nurturing leads without always needing to be “on.”
She also breaks down how to collect “walking testimonials”—natural client feedback and language that can be repurposed into high-converting content. By listening to what your clients are already saying, you gain a goldmine of messaging insights.
And for anyone worried about keeping up with content? Kendall shares how to strategically repurpose what’s already working so you’re not reinventing the wheel every week.
Whether you’re just starting out or scaling a service-based business, this episode is a must-listen if you want to sell with confidence, connect with your audience, and ditch the guilt for good.
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Connect with Kendall through her newsletter at wallflowerfridays.com or explore her LinkedIn content for practical examples of authentic selling through storytelling.