Founders often feel guilty about raising prices. Reframe this: sustainable profit margins are what allow your business to survive and continue serving customers. Without profitability, the business fails and everyone loses. It's a matter of ensuring longevity, not greed.

Customers don't care about your P&L or that a competitor is a "side hustle." To justify a higher price, you must clearly communicate tangible benefits like better organization, time savings, or superior staff, which directly improve their experience.

Innovate by adding unique, low-cost features with high perceived value. For a sports league, this could be live commentary by volunteers or custom trading cards, creating a premium experience that justifies a higher price.

A low price can signal a low-quality or immature product, repelling enterprise or mid-market customers. Raising prices can make your product appear more robust and suitable for their needs, thus increasing demand from a more desirable—and previously inaccessible—market segment.

Don't let your personal perception of what's 'expensive' limit your earning potential. Set your price high based on the value you provide. It is easy to lower a price that gets no buyers, but impossible to know if you could have charged more if you start too low. Never say no for the customer.

The naive view is that lower prices are always better for customers. However, higher prices generate higher margins, which can be reinvested into R&D. This allows the vendor to improve the product much faster, ultimately delivering more value and making the customer better off than with a cheaper, stagnant product.

A very high sales close rate (80% or more) is a clear indicator that your product or service is significantly underpriced. Instead of celebrating the rate, view it as a signal to raise prices by 3-4x to maximize revenue, even if the close rate drops.

Pricing is your most powerful lever. For a typical service business with a 10% net margin, a simple 10% price increase goes directly to the bottom line, effectively doubling the company's total profit without any additional operational cost or effort.

When negotiating a price increase, if the customer accepts immediately without pushback, it’s a strong signal you've significantly underpriced your product. Buildots' founder prepared for a negotiation over a 4x price increase, but the client agreed instantly, revealing the product's true value.