Comment by dang
FWIW, I've spent time at YC open-source events where later-stage founders advise earlier-stage ones, and this isn't the kind of advice they give. In fact they would describe that as a terrible strategy and tell startups to avoid it.
If I were to give an example of actual advice I've heard, using the terms of your comment, it might be: keep the nerds happy with free open-source software that actually works, then charge money for things that companies (especially enterprise companies) actually prefer to pay for.
The "paid hosted offering" pattern is the most common of these, since nerds might want to run their own instances but many IT departments do not.