Possibly the worst or most unfortunate money decision ever.
Apple's third co-founder Ronald Wayne, sold his 10% stake for $800 in 1976. (The stake is currently valued at $270 billion).
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In the early 1990s, Wayne sold the original Apple partnership contract paper, signed in 1976 by Jobs, Wozniak, and himself, for US$500. In 2011, the contract was sold at auction for $1.6 million.[17] Wayne has stated that he regrets that sale.
And if things could not get worse...
Circa 2004, aged 70, Wayne claimed he was robbed of his life savings, which he kept in a strongbox in his home. Amongst the assets he held was 145 ounces of gold (~$247,000 as of November 2022[19]) and $3,000 worth of silver coins; the precious metals were never recovered.