When to Raise Your Prices - EP 435

When to Raise Your Prices - EP 435

June 1, 2026 · 36 min · Episode 435

About this episode

Tony Whatley discusses the importance of raising prices confidently and the psychological barriers entrepreneurs face in doing so.

What if the biggest thing holding your business back isn't your competition — but your fear of charging what you're truly worth? In this powerful solo episode of the 365 Driven podcast, host Tony Whatley tackles one of the most uncomfortable yet critical topics for entrepreneurs: raising your prices with confidence. Tony breaks down the psychology behind why so many business owners undercharge, delay price increases, and attract difficult customers by trying to compete at the bottom of the market. From money mindset limitations to fear of customer reactions, he explains how entrepreneurs unknowingly sabotage their own growth by pricing based on personal comfort rather than the actual value they create. Throughout the episode, Tony shares real-world examples from his own entrepreneurial journey and client success stories — including attorneys, laboratory owners, and service providers who dramatically increased profits simply by repositioning their value and raising their rates strategically. He also reveals why cheap customers often demand the most, while premium clients respect expertise, efficiency, and quality. You'll learn: How to know when it's time to raise your prices Why…

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