[presspot]

Really? I'm not so sure.

For example, an open source "community edition" could be treated as a freemium product and an OSS marketing could adapt a PLG playbook to help identify and nurture those who are good candidates for the "enterprise edition". Also, you have a community. They're in Slack or Discord, making pull requests, filing Github issues. You should be able to adapt the CLG playbook to help identify and nurture future customers from within the community.

[smoldesu]

In practice, I have never once seen this work. Arguably Canonical and Red Hat are the two best examples of CLG/OSS business models, and both of them have uneasy relationships with the greater Open Source community. Canonical is seen and treated as the Microsoft of the Linux world; their promises aren't worth the bits they're delivered on, and they'll sacrifice anything for money. Red Hat is cautiously embraced by the community despite being much more benevolent, usually because their aligned interests don't always consider power users or extensible architecture. They move fast, break things, and forgot to ask your opinion.

Neither Canonical or Red Hat are particularly well-loved by the greater Linux community, for wildly different reasons. At the core of their failure is the illusion of a successful Open Core business (or "freemium" as you put it). The delusional business obsession over ruining the free version of software is exactly why Open Source is so successful where businesses fail. You should research why Linux and BSD won over the alternatives from AT&T and IBM; they didn't have a premium or pro version, they were the pro version. The creation story of GPL, Free Software and Linux as a whole is a warning about how business models collapse when they molest functionality for money.

[presspot]

I see your point, but I have to believe there is a commercial path that can be mindfully pursued. You can build hosted tools, or add commercial value with an "app" model where there is a clear division between the platform, which is free, and the apps, which can be paid or not.