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Ron Wayne opted out too soon – $95 billion

Along with Steve Jobs and Steve Wozniak, Ron Wayne was one of the founding fathers of Apple. He joined the company oversee mechanical engineering and documentation and received a 10% stake in return.

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Wayne was concerned about Apple’s debts so sold his 10% stake for 800 million. If he had stayed on and kept his stake it would be worth more than 95 billion, making him one of the richest men in the world.