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RailsConf 2019 - The Unreasonable Struggle of Commercializing Open Source by Justin Collins

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With at least $55 billion in open source-related acquisitions in 2018, you might think we finally figured out how to fund and monetize open source software. Unfortunately, we have only reached an awkward stage of growing pains! With conflicting goals, people are struggling to turn their OSS work into revenue while not losing the powerful open source effects which made the software successful in the first place.

From the perspective of someone who has gone through the pain of commercializing open source, let’s take a deeper look at the unexpected challenges and potential solutions.

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In the presentation titled "The Unreasonable Struggle of Commercializing Open Source," Justin Collins discusses the complexities and challenges of transitioning open source software (OSS) to a commercial product. He begins by reflecting on his own experience founding and developing Brakeman, a static analysis security tool for Ruby on Rails, which he open-sourced during his internship at AT&T Interactive. Collins shares insights on the awkward dynamics between maintaining the original open-source project and offering a paid version, especially regarding naming conventions that can lead to confusion among users.

**Key points discussed throughout the video include:**

- **Naming Challenges**: Collins experienced difficulties in creating distinct names for the open-source and commercial products, leading to brand confusion.
- **Competing with Free Versions**: He emphasizes the challenge of persuading users to pay for a Pro version of a tool that is available for free; users see less value when they are satisfied with the existing OSS version.
- **Initial Pricing Mistakes**: His team initially mispriced the product and had to adjust their pricing model significantly to attract paying users. Collins explains that pricing must reflect the market demand and customer willingness to pay.
- **Community Marketing Concerns**: Collins discusses his discomfort in promoting the commercial product to the open-source community, which resulted in a decline in engagement over time.
- **Managing Open Source and Proprietary Development**: He reflects on the complexities of maintaining both free and paid versions, including what features to allocate to each.
- **Moral and Legal Concerns**: There are ethical considerations regarding the ownership of code contributed by others and the implications of GPL dependencies in commercial projects.

Collins concludes with broader observations about the sustainability and future direction of open source, referencing ongoing debates about licensing and the economic landscape surrounding it. He invites the audience to consider the evolving story of OSS and how it continues to contribute to and shape modern software development in light of these commercial pressures.

Taking away from the talk, Collins emphasizes the need for thoughtful strategies when commercializing OSS, balancing community expectations with business realities, and addressing the challenges posed by open-source licensing changes as companies navigate these waters.

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