It wouldn't be a financial loss but it can hurt your growth. Free users are a huge distraction since what they ask for can be very different from what paying users ask for.
As a bootstrapped startup, your goal is probably to get to ramen-profitability as soon as possible so you can quit your job and focus on it full-time. You're not gonna get there fast enough by making free users happy. Paying users are what move the needle.
That's awesome! There's no one way to do this so if it's working for you, then keep doing what you're doing. Are you running a B2C startup by any chance?