If things had gone differently, two of the most polarizing men of 2023 might have partnered up two decades ago.
According to a new book by Walter Isaacson, Elon Musk traveled to New York in around 2000 to meet with Rudy Giuliani—then the city’s mayor—hoping to secure him as a “political fixer” for Musk’s online payments business, PayPal.
The meeting didn’t go well. “It was like walking into a mob scene,” Michael Moritz, a key PayPal investor who tagged along for the trip, is quoted as saying in Elon Musk. Giuliani “was surrounded by goonish confidantes. He didn’t have any idea whatsoever about Silicon Valley, but he and his henchmen were eager to line their pockets.”
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Moritz claimed that Giuliani, who was wrapping up his mayoral term, demanded a 10 percent stake in the business—which ultimately sold to eBay in 2002 for $1.5 billion.
Musk dismissed Giuliani as a loon, telling Moritz, “This guy occupies a different planet.”
A representative for Giuliani did not immediately respond to a request for comment.
Around the same time, PayPal was suffering from internal tumult. Musk had become the company’s CEO after his startup, X.com, merged with a rival called Confinity, the founders of which included Peter Thiel and Max Levchin.
Some members of the team wanted to focus on doing business with eBay, while others, like Musk, wanted to offer payment services to multiple industries. He pushed to rename the business X.com and wanted the PayPal platform to be refashioned as X-PayPal.
The problem: That sounded more like a porn site than a reputable financial services operator. “If you want to just be a niche payment system, PayPal is better…But if you want to take over the world’s financial system, then X is the better name,” Musk argued, undeterred.
Musk lost the battle, and he was eventually kicked out as chief executive, with Thiel taking over. When PayPal was acquired, Musk funneled his earnings into a rocket company, SpaceX, now worth roughly $150 billion.
And he later found a way to settle the old score. This summer, Musk rebranded Twitter—which he acquired for $44 billion last year—as X.com.
