But to position “the Basecamp way” as being primarily about positioning yourself for fundraising is a depressing perspective.
Having a discussion about the challenges of bootstrapping is welcome.

This is a fair point. The fundraising frame was used as a reference to the series of posts by Justin in which he’s wrestling with which path to pursue for Transistor. Your added context here really resonates that funding as the goal or bootstrapping as a strategy to attract funding loses the plot. And agree with your conclusion and share your sympathy for those struggling.