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Are there any other (prominent) companies that have an employment model like Gumroad's?
There are cooperatives (coops), were workers are also owners. But there you are not working for several companies building equity on all. But most US I knew of are no longer active. Only https://www.gcoop.coop/ in Argentina.

Oh, and found this articles: http://www.vintagedigital.net/content/setting-software-co-op and https://www.scribd.com/document/26587085/Tech-Coop-How-To

And also the Hacking Business Model proposed by Monty from MySQL fame was similar to the coop model: https://www.forbes.com/sites/reuvencohen/2012/07/25/the-hack...

(OP) I've actually been trying to figure this out myself and haven't found one yet. Started this Ask HN (https://news.ycombinator.com/item?id=33978686) to try to find out.

My prediction is that we will start to see more over the coming years though. Whether that means finding creative ways to share equity/upside, or using more contractors and part-time folks.

For US contractors, I wonder if the pay is sufficient to cover health insurance (which I'm guessing the contractor has to arrange for themselves). Are there flexible contractor groups (that aren't agencies) that are able to negotiate for lower insurance prices?