Paid, every time. John says "a big lesson we Learned is that you should do paid pilots." Their free pilots felt like validation but weren't — customers "did not really care, they were just either being nice or just thought it was like a cool tool they could try out."
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The founders explain why free pilots misled them. They ran free pilots thinking it would tell them whether the customer truly wanted the product, but free interest is cheap — people will take a free tool out of politeness or curiosity. The signal they actually needed was money: "if you are [solving a real pain point], they will be willing to throw any amount of money at you for it, even if it doesn't work." That insight directly shaped how they ran the first real deal, where the customer paid and signed a contract before the product was even close to finished.