A little bit of background: back in 1999, I was working for a large financial services company (you've heard of them). One of the biggest topics on everyone's minds was how to crack the online market. Every major bank was devoting serious money and resources to the question.
This was also going on in the startup world. Two of the leading companies in this space were Confinity and X.com, which would merge about a year later into the company known as PayPal.
You often hear about Elon Musk being the co-founder of PayPal, but that somewhat misrepresents what actually happened. These were two different companies with very different approaches and proposed products, and they brought very different things to the table. Confinity was focused on the area of payments and had already launched the PayPal product and had identified eBay as being the most important early market. Elon Musk's X.com was a more general, less well-thought-out idea for an all-services bank, something that would not be practical online for years.
X.com had more money and resources, particularly teams of engineers, and was technically the acquirer rather than the acquiree, while the primary product and basic approach that made the combined company viable enough to sell to eBay came from Confinity.
For an example of the quality of ideas that Musk brought to the table, here's an anecdote from Peter Thiel:
I was thinking of doing a book on PayPal … and [the chapter on Elon Musk] was going to be titled, “The man who knew nothing about risk.” … We had decided to give a credit card to anybody who wanted them. You got up to $10,000 credit limit. Elon had told the woman who was rolling the service out that he wanted 1 million people to be using the new credit card by the end of the year. Fortunately, it was about two levels down from the front page, and so not that many people were able to discover this. Some people did. They wrote us back and said, “You know this is fantastic! I haven’t had credit in years. I can’t believe you’re offering me credit. I haven’t even had a checking account in 10 years!” … We ended up with something like a 50% charge back rate—the worst subprime companies are like 4%-6%. And then, happily, we sort of rolled that product back very quickly.
The 2018 Quartz article I pulled this quote from goes to embarrassing lengths to depict Musk as a bold visionary rather than someone who is really bad at business (the earlier Quartz article it links to is even worse), but these are not isolated cases. If you follow the man closely, you will find countless examples of Musk failing to grasp basic and sometimes self-evident concepts about the bond market, manufacturing, manned spaceflight, you name it, all delivered with an air of self-confidence that can only be called delusional.
After PayPal, Musk's business career has consisted of running a moderately profitable niche car company and having founded or acquired a string of companies that either lost money or were only occasionally profitable. His unprecedented fortune in no way reflects the money his companies have made. Instead, it is the product of his ability to convince people to give him money, be they investors, stockholders, or taxpayers.
It is a disconnect that sets Musk apart from the robber barons of the Gilded Age and every other multibillionaire (in 2026 dollars) I can think of before the year 2000.
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