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A couple historical lessons learned about using, building on, and contributing to free (open source) software.

• The longer your changes are off the main branch, the harder and more expensive they are going to be to integrate. This is true of a feature branch on your own software project and of "out of tree" changes to a large open-source project like Linux.
• If a major dependency of your business is an open-source software project (e.g. Postgres, Ruby, Linux, etc.), you should probably be employing a contributor who has a strong relationship with that project. E.g. the various companies that have employed Aaron Patterson to work on Ruby.

Regarding the second bullet point, another common pattern now days is for open-source maintainers of important (but much smaller than, say, Linux-size) software projects to crowd-fund their work via GitHub sponsors from companies and individuals.

Shared by Jeremy Schneider on Linkedin.