Before making the move, Bezos imagined himself at 80 and considered what he would regret more: failing at the business or never trying at all. Jeff Bezos was working at a Wall Street hedge fund when he spotted an opportunity to sell books online in the early 1990s. Turning the idea into a business, however, meant leaving behind a lucrative job and taking a risk on the internet.
As reported by Fortune , Bezos believes that experience can improve an entrepreneur’s chances of building a successful company. What might trouble him, however, was never having attempted it. Bezos also acknowledged that leaving his job meant giving up benefits such as his annual bonus. Thinking about his future rather than short-term financial considerations helped him reach a decision. Once he decided to take the plunge, Bezos began working on the idea that would eventually become Amazon. However, he understood that a business plan could not account for every challenge that lay ahead. In the interview, Bezos described the initial stage of building a company as particularly difficult, explaining that the discipline of writing a plan helped entrepreneurs think through the challenges, even if reality eventually demanded changes. Amazon also went through an early name change. Bezos initially registered the business as Cadabra, inspired by the word ‘abracadabra’. He later changed it after realising that the name sounded too similar to ‘cadaver’.
During his drive from New York to Seattle, he drafted an approximately 30-page business plan outlining his vision for an online bookstore.
He said he realised that failing at a new business would not be something he would regret.
Before starting Amazon, Bezos worked at D.E. Shaw, a New York-based hedge fund, where he had built a promising career. In the early 1990s, as internet usage began to grow, he saw an opportunity to sell books online and started thinking about setting up a business of his own. Leaving a well-paying job was not an easy decision. To think it through, Bezos came up with what he called a ‘regret minimisation framework’. Instead of focusing only on what he stood to lose by quitting, he imagined how he might look back on the decision later in life. Bezos has also spoken about the importance of gaining experience before starting a business.
In a 2001 interview with the Academy of Achievement , Bezos explained that he imagined himself at 80, looking back at the important decisions he had made. Speaking at Italian Tech Week in 2025, he suggested that young people should not feel pressured to drop out of college to become entrepreneurs, pointing out that successful college dropouts are exceptions rather than the norm.
