It's easier to sell X to someone who routinely buys X than someone who has never bought X, which is why most successful conversations about OSS financial stability will be about packaging it for corporate consumption as something they already spend billions of dollars on.
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I wrote a bit about this here: https://www.ericholscher.com/blog/2016/aug/31/funding-oss-marketing-money/#traditional-funding-sources … -- it's what caused Read the Docs to choose to do advertising (ethically) as our funding source. Billions of dollars are already spent there, as you said.
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maybe larger oss projects could sell support and trainings
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