Today's Reading

It ought to be remembered that there is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new. This coolness arises partly from fear of the opponents, who have the laws on their side, and partly from the incredulity of men, who do not readily believe in new things until they have had a long experience of them.

—Niccolò Machiavelli, The Prince

Those who have learned to walk on the threshold of the unknown worlds, by means of what are commonly termed par excellence the exact sciences, may then, with the fair white wings of imagination, hope to soar further into the unexplored amidst which we live.

—Ada Lovelace


"Fuck, you're making me rummage around the attic," said Elon Musk.

We sat in his living room, but the metaphor still fit. Musk was about to tell me the story of PayPal.

At the moment we met, in January 2019, PayPal—a company he cofounded some two decades earlier—was likely the furthest thing from his mind. The day before, he had announced significant layoffs at Tesla Motors, the electric car company he has led since 2003. And just the week before that, he had cut one-tenth of the workforce at SpaceX, the aerospace manufacturer and transportation firm he started in 2002. With all this present swirl, I didn't know how much Musk would want to delve into the past, and I was ready for him to trot out a few familiar talking points and send me on my way.

But as he spoke about the internet's development and PayPal's origins, the stories spilled out. About his first internship at a Canadian bank. About building his first start-up, then his second. About what it felt like to be overthrown as CEO.

By the end of the afternoon—nearly three hours later—I suggested we pause. We had only scheduled an hour together, and though Musk had been generous with his time, I didn't want to wear out my welcome. But even as he stood to show me out, he launched into another PayPal story. Forty-seven years old, Musk spoke with the enthusiasm of someone older asked to relive his glory days: "I can't believe it's been twenty years!"

* * *

It 'was' hard to believe—not just the years that had passed, but how much PayPal's alumni had accomplished in them. If you have used the internet at all in the last twenty years, you've touched a product, service, or website connected to the creators of PayPal. The founders of several of our era's defining firms—the creators of YouTube, Yelp, Tesla, SpaceX, LinkedIn, and Palantir, among others—were early PayPal employees; others occupy top posts at Google, Facebook, and Silicon Valley's leading venture capital firms.

Both in the foreground and behind the scenes, PayPal's alumni have built, funded, or counseled nearly every Silicon Valley company of consequence for the last two decades. As a group, they constitute one of the most powerful and successful networks ever created—power and influence captured in the controversial phrase the "PayPal Mafia." Several billionaires and many multimillionaires have emerged from PayPal's ranks; the group's combined net worth is higher than the GDP of New Zealand.

But to look only at their wealth and impact on technology is to miss the group's wider imprint: PayPal's alumni have built world-changing micro-lending nonprofits, produced award-winning films, written bestselling books, and advised politicians at every level—from the state house to the White House. And they're far from done: Today, PayPal alumni have taken as a mission everything from cataloging the world's genealogical records to restoring three billion acres of forest ecosystems to "scaling love"—bringing their PayPal experience to bear in each case.

They've also been at the center of the biggest social, cultural, and political controversies of our age, including bitter fights over free speech, financial regulation, privacy in technology, income inequality, the efficacy of cryptocurrency, and discrimination in Silicon Valley. For its admirers, PayPal's founders are a force to be emulated. For its critics, the group represents everything wrong with big tech—putting historically unprecedented power into the hands of a small clutch of techno-utopian libertarians. Indeed, it is hard to find a lukewarm opinion about PayPal's founders—they are either heroes or heathens, depending on who offers the judgment.

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