Though he recently told me that he thinks all OSS should bootstrap and never take investment, which doesn't exactly align with top COSS co spreadsheet he also maintains.
Steph and I have been breaking things down from our chat, and basically came to the same conclusion, though often favoring closed source where one might GPL/NonC license that crust around the core. Also that outside investment is to add fuel to an existing fire, COSS or fully private makes less difference than showing you've built something people want.
Do you have any new videos or podcasts? Always love to hear your thoughts, you put things very succinctly!