Sometimes, I read things by CEOs about how a company works on the inside and I wonder if it really looks like that, or if it is a view from the top that doesn't reflect what it's really like.
This article, with its discussions of the upsides and downsides, is accurate to my experience and my understanding of other people's experiences. For many people, Gumroad wouldn't be a great place to work, but for those of us who want to work like this, it is exactly what we need. Very glad to be working at Gumroad and working in the ways the article describes.
Edit: Following up with a few FAQs from posts in the thread:
* Health Insurance: I'm personally lucky enough to still be covered on my dad's health insurance until I turn 26, thanks to the ACA, though for supplementary (vision, dental) I make more than enough to afford proper health insurance on the open market. Everyone at Gumroad is paid very well and should be able to afford the same.
* Regarding overtime, benefits, etc: we make very competitive rates as contractors. I sincerely appreciate your concern, though.
* On the shift from full-time employees to contractors, the company declined and was rebuilt over a period of five years. I'm a relatively recent addition, so I only know Gumroad as it is now, I cannot comment on how it was. All I can say is that it's not like Sahil went out and fired everyone and then the next day it was a bunch of contractors.