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.

In recurring business relationships, winning every last penny is a short-sighted victory. Intentionally allowing the other party to feel they received good value builds goodwill and a positive reputation, leading to better and more frequent opportunities in the future. It inoculates you against being price-gouged upfront.

Price objections don't stem from the buyer's ignorance, but from the seller's failure to establish clear economic value. Before revealing the cost, you must build a business case. If the prospect balks at the price, the fault lies with your value proposition, not their budget.

Discussing pricing early doesn't mean you're in the proposal stage. True proposal and negotiation begins only after you have secured explicit agreement on the problem, the solution, and from the key decision-maker. At this point, the deal would close if it were free; price is the only remaining variable.

Selling a small, cheap "land" deal to an enterprise customer is dangerous. When you try to expand, they will question the 10x price jump, making it nearly indefensible. Start with a price ($75k-$150k) that reflects enterprise value to avoid being trapped by a low initial anchor.

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.

To minimize risk, the founder initially ordered small quantities of custom packaging, resulting in a high cost of $6.31 per box. In hindsight, she advises founders to "bet on themselves" by ordering larger quantities to significantly lower cost of goods, even if it ties up capital longer.

Instead of hiding price until the end of the sales cycle, be transparent from the start. Acknowledge if your solution is at the high end of the market and provide a realistic price range based on their environment. This allows you to quickly qualify out buyers with misaligned budgets, saving your most valuable asset: time.