Rob started from an idea he had already formed for what became Drip's first version, and vetted it with about a dozen people before building. Months later, after shipping, he grew unsure those same people still wanted what he had built, so he sent a large email survey to re-confirm demand.

“I had an original idea and I vetted it with, you know, a dozen people”

Early testers came from manual, one-by-one onboarding off Rob's own audience/email list. He gave people open-ended free trials, sometimes six weeks long, until they had clear evidence Drip was making or saving them money.

“I was giving people as long as they needed to feel confident that Drip was basically making them money”

For an early trial user, once real financial results showed up during the free trial (roughly $400-500 in attributable conversions within about three and a half weeks), Rob emailed to ask directly whether they felt it was worth paying for, and they said yes.

“So I emailed them and said do you feel like this is worth it? And they said yeah.”