I think the big VC raise is often the moment that many companies' relationship with their users goes from friendly to adversarial. I suspect this is because the

I think the big VC raise is often the moment that many companies' relationship with their users goes from friendly to adversarial. I suspect this is because the incentives become misaligned. A bootstrapped company needs to keep its users happy to keep the money coming in for operations and growth. User churn is expensive at this stage. A funded company has other options such as running at a loss to attract new users and outpace any churn in the existing user base.