#14: Ronald Wayne Sold His Apple Stake for $800
Ronald Wayne joined Steve Jobs and Steve Wozniak as Apple’s third co-founder in 1976, receiving a 10% stake. Twelve days later, worried about personal financial liability if the fledgling company accumulated debts, he sold his interest back for $800 and later accepted an additional payment. Had that stake somehow remained untouched through decades of dilution and corporate changes, its theoretical value would be staggering. Calling it a “business loss” is hindsight-heavy, but few $800 decisions have generated more painful calculators.

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