Launched free because I wanted users before revenue. The logic felt solid: get people using it, prove the value, then figure out monetization. Classic founder reasoning that sounds smart until you live with the consequences.
Free users behave differently than paying ones. They're less engaged, less forgiving, and paradoxically more demanding because they feel no obligation to be patient. They also give terrible product feedback because their relationship with the product is casual. They'll tell you they love a feature they've used once and ignore something they'd rely on daily if they were invested enough to actually learn it.
When I eventually introduced pricing after five months, I lost about 80% of the user base overnight. The people who stayed were the ones who would have paid from day one. All that time optimizing for free user behavior, building features they requested, prioritizing what kept them engaged, most of it was wasted because the paying customers had different needs and different usage patterns entirely.
What charging from day one gives you is signal clarity. If someone pays you money, even a small amount, their behavior tells you something meaningful about your market. If they don't pay, you've learned something equally valuable. Free users give you vanity metrics and false confidence. Paying users give you a business.