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In early September, former Theranos CEO Elizabeth Holmes requested a new trial, arguing that a key prosecution witness had expressed regret about his role in her criminal conviction.

It’s worth revisiting why she’s facing jail time for her actions while other founders who obliterate billions of dollars simply walk away from their failed companies. Many reemerge seemingly unscathed, like a phoenix from the ashes, and raise millions more for their next big ideas.

The key difference: Not crossing the fine line between optimism about the future, which all tech founders must have, and fraud, which can land a founder behind bars.

To be clear, Holmes is not alone in her plight, she’s just the most recent, high-profile poster child of a founder who crossed the line. And there are many examples of founders who have tiptoed right up to, if not over, the threshold — and gotten away with it.


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