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I work at a similar company (less than 10 employees, no deadlines, (almost) no meetings), but unlike Gumroad we actually have health insurance, 401K with matching, donation matching, etc. So it is possible to to have "freedom" without laying everyone off and removing all benefits. You can read more about it here: https://simpixelated.com/two-year-work-retrospective

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Are all of your employees there for true flexibility (ie spending more time on their own project than work?)

I don't think so. Everyone seems to put in a solid day working. No one is counting the hours, but we seem to be productive enough. Still, I definitely joined the company to get away from working more than 40 hours per week and feeling stressed all the time.

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