Goodwill handles over 4.4 billion pounds of donations every year. Most of it gets cleaned, priced, and sold at a retail store. Now, Goodwill is using AI listing tools to sell the best items online before they ever reach the floor. That’s squeezing the flippers who built businesses on those finds.
We got behind-the-scenes access to see how Goodwill sorts and sells millions of items a year, then followed the resellers fighting for what’s left. Some are earning six figures sourcing vintage clothes by the pound. Others have moved to live selling on Whatnot, which recorded $6 billion in sales in 2025, nearly as much as Goodwill itself.
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