Business building versus monetization
We shouldn't talk about monetizing open source projects. We should talk about building sustainable, financially successful businesses with open source projects at their core.
It's a subtle, but important, difference.
If we say 'monetize open source,' it implies:
The open source project came first (not always the case!), and that the business is secondary to the project.
That everything is downstream from the project. In reality, you should have an interplay between company, product and project, not OSS ruling all.
That you see your community as a tree to shake dollars from. You're not doing that, right? Instead, think about how the commercial product can deliver value above and beyond the open source project, and who would be willing to pay for that value. The target market for your commercial offering is very often not the same as the target market for the OSS, and even if there is perfect overlap the individual OSS users are usually not economic buyers.
When you frame the challenge as building a business around an open source project rather than monetizing open source, you put the business part front-and-center — which is the mindset you should have if you're building a business. You also become more attuned to the complex relationships you are managing — it’s not just a question of how to monetize a project, but rather how to give away some value (in your project) and capture some value (in your commercial offering).