Gumroad's journey has been interesting:
https://sahillavingia.com/reflecting -> Billion dollar journey with VC backing to Kleiner selling back their stake to Gumroad for $1, which enabled Sahil to steer the company in a different direction.
Can't help but notice he's basically knowingly "donating" the code to multi-billion corporations to train their LLMs on (while in general those same corporations source their training data in ethically questionable ways), while mere mortal human individuals and small businesses are bound by a non-free license. An interesting decision to say the least.
Sahil anticipates AI will significantly commoditize software. Especially following DeepSeek's impact. He has promoted Devin via twitter and likely aims to position Gumroad as the leading creator-focused alternative to traditional Open Source e-commerce platforms.
Perhaps the shift to making the source available has more to do with work culture: https://sahillavingia.com/work