Startup Sales — 5 Common Sales Mistakes by Founders
August 12, 2025
Founders are responsible for the first sales a startup will make. For many founders, this is one of their very first experiences of sales and mistakes are often made.
Today we’re talking about starting to charge your customers money.
1. A common pitfall for most founders is undercharging over fear of rejection. Trust me, you’re going to get plenty of noes anyway, so it’s best not to price as a budget service.
2. Don’t worry about setting too high a price. The “wince” test solves your problem. Where if a customer balks at your price, you simply negotiate down. It works surprisingly well.
3. I recommend segmenting your first customers into 5 groups. For enterprise tools, a group might be just 1 customer. For consumer apps, it might be 100 customers. Let the first customer group use the product for free, we just want feedback. For Group 2, set a nominal fee, say $1, to test the purchasing process. Then for the remaining groups, 3 through 5, escalate the price significantly each time and use the wince test when a customer pushes back.
Best of luck out there.
