A sale is just the first step. The true measure of product-market fit is high retention, specifically when the product becomes so integrated into a customer's workflow that the idea of canceling their subscription would be bizarre and disruptive. Founders should be designing for this "weird to cancel" status.

When a buyer insists on a "termination for convenience" clause, explain that it nullifies the "length of commitment" lever. This effectively changes a multi-year agreement into a month-to-month one, which logically carries a much higher price (e.g., a 30-35% increase). This frames the clause not as a legal term, but a commercial one with a clear cost.

When a customer cancels, don't just offer a discount. Create a capture system that presents tailored solutions based on their stated reason—offer a plan downgrade for cost issues, a 15-minute setup call for confusion, or a feature workaround if something is missing. This preserves value while solving the root problem.

Unlike transactional purchases requiring a proactive decision to buy, subscription models thrive on consumer inertia. Customers must take active, often difficult, steps to cancel, making it easier to simply continue paying. This capitalizes on a psychological flaw, creating exceptionally sticky revenue streams.

To increase retention, offer subscribers a permanent, high-value upgrade (e.g., 'free bacon for life') that they lose forever if they cancel their service. This leverages loss aversion, making the cost of churning much higher than the monthly fee.

A significant one-time startup fee increases a customer's initial investment and creates a psychological barrier to leaving. This counterintuitive strategy can drastically reduce churn and increase lifetime value, as customers feel they have more to lose by canceling.

Education provides one-time value, so it shouldn't be a recurring charge. Customers churn once they've learned the skill. Instead, sell education as a high-ticket, one-time product and offer community or ongoing services as a separate, lower-priced subscription. This aligns billing with value delivery.

Many subscription companies employ a "penetration strategy," pricing below cost to attract a large user base. Once loyalty is established, they leverage their pricing power to increase profits, shifting focus from pure growth to appeasing shareholders who now demand profitability.

Don't just sell a product; become an indispensable part of your customer's workflow. By offering integrated products and services, you create a value ecosystem that locks out competitors and makes leaving an impractical and undesirable option.