At just 34, Jeff Bezos made it to the Forbes billionaire list by making a bold move most rising Wall Street stars wouldn’t dare to take. In 1994, Bezos, a Princeton-trained computer scientist and D.E. Shaw vice president, discovered a report stating that “Web usage was growing at 2,300 percent per year.” It was a figure unlike anything he had ever seen. Seizing the opportunity, Bezos left his high-paying job in New York and drove to Seattle. With $10,000 of his own money and $84,000 in interest-free loans, he founded Amazon.com from a rented garage.

That decision has since paid off exponentially. Bezos’ willingness to take the leap helped him become the world’s wealthiest person from 2017 to 2021, according to Forbes, before Elon Musk took the title. Today, Bloomberg’s Billionaire Index values his net worth at $232 billion, placing him second globally. Bezos often describes his decision as a “regret-minimization framework”—the idea that failing would hurt less than never trying. Three decades later, Amazon is worth over $2.2 trillion, and Bezos has become one of the richest entrepreneurs in history—all because he chose to walk away from the safety of a stable career and take a chance. By July 16, 1995, just two months after its launch, Amazon was already raking in $20,000 a week in orders. The company went public on May 15, 1997, at $18 per share, and a year later, Bezos’ wealth soared to $1.6 billion, landing him on Forbes’ rich list.

What is ‘Regret-Minimization’ Strategy?

The “Regret-Minimization” strategy is a decision-making approach Jeff Bezos credits with shaping his career, especially the choice to leave his secure job and start Amazon. Bezos has previously said that the concept is straightforward: when facing a big decision, you ask yourself, “Which choice will I regret less in the future?” Bezos used this mindset when considering whether to leave his stable Wall Street career to take the risk of building a new business. Instead of focusing on the fear of failure or the risks involved, he focused on the potential regret he might feel later in life if he didn’t pursue the opportunity. The strategy is all about making decisions that reduce the likelihood of looking back with regret, particularly when the future is uncertain. Meanwhile, the Amazon founder and his fiancée Lauren Sanchez are set to tie the knot on an island in Venice. Their much-anticipated wedding is expected to be the event of the summer in Italy, taking place between June 24 and June 26.

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