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I hate asking for money.
In the past, I would have never done it. That's changed. I now see that to be able to pay writers to work on the articles I want to read, I need to invest in the site. That takes effort, and one person can't do it alone.
I am very transparent about where money goes. I pay approximately $50 a month in hosting fees on Squarespace, Revue, and Gmail. The goal is to help the site pay—and pay writers for the work they do— for itself as it grows. Every dollar helps!