Elon Musk's X.com and Peter Thiel and Max Levchin's Confinity (product PayPal) competed for the same group of transfer users from 1999 to 2000, with both sides burning cash continuously. Musk's initial merger proposal was deemed too low by the other side, and after negotiations broke down, both parties merged in March 2000 with nearly equal equity, continuing to use the name X.com, with Musk as CEO.

Post-merger conflicts centered on branding and direction. Musk wanted to turn the company into an internet bank and downplay the PayPal name, but internal focus groups showed users distrusted X.com and preferred PayPal; he still pushed for the name change. There were also disputes over the technology stack between Unix and Microsoft routes. In September 2000, Musk and his wife Justine combined their postponed honeymoon with a fundraising trip to Australia. While he was away, Levchin, Thiel, Reid Hoffman, David Sacks, and others collectively resigned to pressure the board to replace Musk, with Thiel taking over, and the company was subsequently renamed PayPal.

Musk retained his position as the largest individual shareholder. In 2002, eBay acquired PayPal for about $1.5 billion in stock, and Musk cashed out approximately $176 million to $250 million (various biographies and disclosures differ), with about $100 million going into SpaceX. In 2008, after a series of rocket failures and running out of personal funds, former PayPal colleague Luke Nosek pushed for their Founders Fund to step in, announcing a $20 million equity investment in SpaceX in August, with Nosek joining the board. This was SpaceX's first institutional funding, coming right after the third launch failure.

Musk was initially extremely angry about the coup but later told a biographer that life is too short to hold grudges and believed that if he hadn't been ousted, he might still be stuck in the payments company. Thiel's side wrote the 2008 check as both a bet on technology and a way to mend old grievances. Since then, the two have maintained contact, with Founders Fund continuing to increase its stake over the next decade, and by the time SpaceX was preparing for an IPO, the fund's holdings were reported to be worth billions. Musk never gave up on the letter X, and over twenty years later, he reattached it to the acquired social product.

In market mechanics, in 1999 both sides were buying the same group of online payment users, selling a burn rate that could not sustain both. In 2000, the board was buying a marketable payment product, selling Musk's full banking vision. In 2008, venture capital was buying cheap launch options, selling the political cost of mending relations with the former CEO. The beneficiaries were initially the surviving PayPal shareholders, followed by the fund that left $20 million in the rocket company; the pressured party was the ousted CEO himself—he used retained equity to turn a coup into fuel for the next company.

Supplement: Before the merger, the two had also shared a ride in Musk's car to discuss a "shotgun marriage," during which they nearly had an accident. PayPal later helped spawn a number of companies, including LinkedIn, early backbone of YouTube, Yelp, etc.; this personnel network is longer than any board vote.

Source: Public information