Jeff Bezos reflects on 'hardest' meetings of his life when he was building Amazon, reveals first question every investor asked him

Amazon, one of the major e-commerce platforms, has a valuation of around $2.38 trillion and its founder, Jeff Bezos is one of the richest men, whose net worth is nearly $300 billion. But thirty years ago, things were not the same and the future of the company hinged on what Jeff Bezos calls the "hardest meetings" of his life, according to a report in Fortune. The tech billionaire revealed that he went through 60 grueling sessions with skeptical angel investors, many of whom initially doubted his idea of selling books online.

Speaking at the New York DealBook Summit, Jeff Bezos said, "I had to take 60 meetings. It was the hardest thing I’ve ever done, basically." He was making these remarks in reference to the entrepreneurial effort required to convince angel investors to invest tens of thousands of dollars into his company.

Revealing that the most difficult challenge for him was to raise Amazon's first million dollars in seed capital in 1995, Jeff Bezos said he offered 20% of Amazon for a $5 million valuation. He eventually secured about 20 investors, each contributing roughly $50,000. However, out of the 60 meetings he held, 40 investors said no.


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What was the first question the investor asked Bezos?

Amazon founder Jeff Bezos recalled that the most common question the investors asked was 'What is the internet?'. Jeff Bezos said he had a tough time convincing investors selling books over the internet was a good idea. “The first question was, "What’s the internet? Everybody wanted to know what the internet was,” Bezos recalled. Few investors had heard of the World Wide Web, let alone grasped its commercial potential.

Bezos admitted his candor may have cost him support, “I would always tell people I thought there was a 70% chance they would lose their investment.” He now reflects that the odds were probably worse, but insists honesty was essential. He also stressed on the fact that those early investors were very important for Amazon. “The whole enterprise could have been extinguished then.” Without their backing, Amazon might never have survived its infancy.

Bezos said getting those investors on board in the mid-90s was absolutely critical. “The whole enterprise could have been extinguished then,” he said. After a successful career on Wall Street, Jeff Bezos' fascination with the internet's potential drove him to create Amazon in 1994. Working out of his garage with a handful of employees, Bezos began developing the software for the site, which he called Amazon.com.

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What is Jeff Bezos' dream job?

Amazon founder Jeff Bezos once shared his unique dream job. In a 2017 conversation, Bezos’ brother Mark Bezos asked him what he would love to do if money weren’t a factor. The Amazon founder replied that his dream job is crafting slow, high-end cocktails behind a bar.

“I pride myself on my craft cocktails. I do have this fantasy that I want to be a bartender,” he said. Bezos further explained that he has “glamorized the job” in his mind, enjoys talking to people, and loves perfecting the art of making a drink.

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During the chat, Bezos admitted he is far from bartender material. He told Mark that he takes a long time to make cocktails and could not keep up with the fast pace of a real bar. “I’m super slow,” he joked, adding that any bar he ran would have to charge higher prices because each drink would take so long to prepare.

He also said he would need to put up a sign for customers that reads: “You can have it good or you can have it fast.”