Replace Sales Pitches with the Sideways Sales Letter for Trust and Lasting Results

Barry Friedman’s business was built around live entertainment, relying on show after show to pay his bills. He had performed on major stages, but one accident on a mountain bike made him question the sustainability of trading time for money. Rather than panic, Barry decided to translate his knowledge into a new online offering for fellow performers. Instead of a single hard pitch, he shared a series of three videos with his modest email list. The first connected over the universal fear of being forced to find a 'real job,' the second gave actionable tips on nailing gigs, and the third reviewed reader-submitted websites, providing teachable feedback.

As viewers commented and asked questions, he responded, building rapport in real time. By the time Barry softly mentioned his coaching program, trust had been established. He sold out his program in days—despite having fewer than 1,000 people on his email list and no previous reputation as a business coach.

This Sideways Sales Letter approach replaced the outdated sales monologue with an interactive, value-first conversation. It leverages what psychology calls the 'mere exposure effect'—the more positive encounters people have with your ideas, the likelier they are to trust you and say yes when you finally make your offer. Barry’s business grew on the strength of these repeated, generous, story-driven sequences, not a single pushy message. That’s how real trust, conversion, and customer loyalty are built in noisy, skeptical markets.

When preparing for your next launch or promotion, start by outlining three stories or insights you want to share that address real problems or questions. Deliver these as emails or posts spaced over several days, each ending with a call for comments or reflections. Bring your audience into the process as active participants rather than passive leads. Only once you've shared value and sparked true conversation should you introduce your offer, positioning it as the obvious next step. Give this sequence a try next time—instead of feeling 'salesy,' you might just find your audience eager to buy.