Pricing is the single highest-leverage number in your business, and the one founders agonise over most and optimise least. A reliable default: pick a price that scares you slightly, then nudge it higher.
Charge more than feels comfortable
Patrick McKenzie's You Can Probably Stand To Charge More is the essay every bootstrapper should read first. Low prices attract the neediest, most price-sensitive, highest-support customers. Higher prices attract serious users and fund the business that lets you support them properly. Just don't treat "charge more" as a law of physics. As Justin Jackson argues, the right number depends on your market, your stage and who you are selling to.
Price on value, not effort
Don't price from "it only took me a weekend to build." For software the cost of one more sale rounds to zero, so cost-plus pricing just leaves money on the table. Price from what the problem costs the customer instead. If you save a business five hours a month, that is worth hundreds, not the $5 you nervously want to charge.
Practical moves
- Three tiers. A cheap anchor, a "most popular" middle where you actually want people, and a premium tier that makes the middle look reasonable.
- Annual plans. Offering roughly two months free for paying yearly is the common convention. It improves cash flow and retention.
- Talk to customers about price. Ask churned users whether price was really the reason (it usually isn't). Ask happy ones what they expected to pay.
- Raise prices over time. Grandfather existing customers and charge new ones more. Nobody ever regretted a product becoming more profitable.
B2B usually beats B2C
Selling to businesses generally lets you charge far more for the same effort, because the buyer has a budget and an ROI calculation rather than a personal wallet. If you can honestly frame your product as making or saving a company money, prefer it as a bootstrapper.