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After his mother's death, Jim McKelvey was haunted by his inaction. This profound regret transformed into a core operating principle: when something needs to be done, he must be the one to do it, rather than assuming someone else will solve the problem.

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The intense, relentless drive seen in many successful entrepreneurs isn't normal ambition. It's often a corrosive fuel derived from significant personal trauma, like family financial ruin. This experience provides a level of motivation that those from more stable backgrounds may lack.

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When deciding whether to leave a stable job to start Amazon, Jeff Bezos asked which choice he would regret more at age 80. People are far more haunted by the opportunities they didn't take than the ones they took that failed. This is a powerful mental model for making bold career leaps.

A Personal Tragedy Forged Square Co-Founder Jim McKelvey's Bias for Action | RiffOn