paypal mafia

The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley

by Jimmy Soni  · 22 Feb 2022  · 505pp  · 161,581 words

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

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lengthy profile in the New York Times. But a 2007 Fortune magazine spread turned the group’s linkages into legend. The piece’s headline—the “PayPal Mafia”—stuck. The photos accompanying the article famously depicted Thiel, Levchin, and eleven other PayPal alums in mafioso regalia. Inspired by The Godfather films, the photo

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PayPal people are the cool kids, they couldn’t have been more opposite that.” Hoffman preferred the term “PayPal Network.” “By grouping it as the PayPal Mafia, a lot of people assume that it’s a whole bunch of people who think about the world in the same way,” he told the

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Amy Rowe Klement, among others—who worked in executive positions and played vital roles in the company’s growth and success. The iconography of the PayPal Mafia photo turned into a false idol—and a worrying one. As carefully documented in Emily Chang’s book Brotopia and elsewhere, Silicon Valley has long

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had troubles with ensuring that women are treated equitably in hiring, fundraising, promotion, boardroom representation, and in the recognition of their achievements. The PayPal Mafia photo and mythology exacerbated this problem, and it gave photographic evidence of the “boys’ club” critique. For some PayPal alumni, the photo served as an

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… so I can maximize my own leverage. Have any tips?” Epilogue In the process of completing this book, I set digital alerts for the phrase “PayPal Mafia.” Like the people who lived the story, I arrived at a complicated relationship with the phrase itself. On one hand, it was a media-friendly

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this or that modern Tweet or recent utterance—I did want to track the influence of the alumni group as a group. Unsurprisingly, the moniker “PayPal Mafia” was popular among the technology set. In the aftermath of an IPO or significant company acquisition, Twitter and other forums would light up with mentions

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; in Canada, the alumni of Workbrain were similarly spotlighted. In Africa, the cofounders of Kenya’s Kopo Kopo spoke explicitly about wanting to build the “PayPal Mafia of East Africa.” In India, there was talk of how the success of e-commerce giant Flipkart had given rise to “the Flipkart Mafia.” Some

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talent nourish an ecosystem? Dozens of these examples came my way through alerts and through friends, but I found the most interesting application of the “PayPal Mafia” in a world far removed from technology entrepreneurship. I hesitated to even share the story here, but it deserves to be documented, if only for

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wall of his cell in the maximum-security Patuxent Institution hung a clipped-out photo—from the November 2007 issue of Fortune magazine featuring the “PayPal Mafia.” * * * Chris’s and Stephen’s interest in the story went well beyond the cover photo. Inside their Maryland prison, the two became amateur experts on

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ventures. The networks Stephen and Chris had been exposed to dealt in laundered money, drugs, and violence and went by a different name: gangs. “The PayPal mafia was the positive example of a gang,” Stephen said. “A lot of the guys in prison link up together for the wrong reasons. They don

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story spilled out of their cell. In their course for new inmates, Chris and Stephen titled their first lesson “What You Can Learn from the PayPal Mafia.” They photocopied their article collection and distributed it, with the mafia photo as the cover sheet. “It’s a really dark photo, and I used

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said, “but I wanted them to photocopy a photocopy so that the original didn’t get ruined!” They would share how the members of the PayPal Mafia started at the bottom. About how many of them were immigrants. About how the founders were young—untried, unsure, and in some cases, unsuccessful. “We

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PayPal’s final day as an independent company, its executives donned inflated sumo suits and wrestled in an oversized ring. Courtesy of Russel Simmons The “PayPal Mafia” moniker was created in earnest in 2007, when several of its alumni were featured in a photo on the cover of Fortune magazine. The photo

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her talking”: Author interview with Huey Lin, August 16, 2021. “like veterans”: David Gelles, “The PayPal Mafia’s Golden Touch,” New York Times, April 1, 2015, https://www.nytimes.com/2015/04/02/business/dealbook/the-paypal-mafias-golden-touch.html. “It was crazy exciting”: Author interview with Amy Rowe Klement, October 1, 2021

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of Yammer,” SFGATE, February 22, 2012, https://www.sfgate.com/business/meettheboss/article/Meet-the-Boss-David-Sacks-CEO-of-Yammer-3347271.php. “PayPal Mafia”: Jeff O’Brien, “The PayPal Mafia,” Fortune, November 13, 2007. “The ‘mafia’ [label] just kind”: Author interview with Kim-Elisha Proctor, May 15, 2021. “Almost everybody here feels”: Author

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background at both the employee’s and author’s discretion. “PayPal Diaspora”: Author interview with SB Master, October 31, 2018. (One year prior to the “PayPal Mafia” headline in Fortune, writer Rachel Rosmarin used the term “PayPal Diaspora” in a piece for Forbes on July 12, 2006, titled “The PayPal Exodus.”) “It

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Tim Wenzel, December 4, 2020. “Immigrating is”: Author interview with David Sacks, November 28, 2018. “The very best”: Max Levchin commentary at panel discussion, Startup2Startup: PayPal Mafia 2.0 (Part 1), accessed October 14, 2021, https://www.youtube.com/watch?v=1WPud4dmdG4. “Were you an intellectual rock star”: Author interview with Tim

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Fintech ‘Mafia’: Meet the Employees-Turned-Founders,” Sifted, accessed July 25, 2021, https://sifted.eu/articles/digital-bank-mafia/. in Canada: Murad Hemmedi, “Canada’s PayPal Mafia: The Surprising Afterlife of Workbrain, the 2000s-Era Startup That Inspired Some of Canada’s Most Promising Tech Companies,” The Logic, December 30, 2020, https

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://thelogic.co/news/the-big-read/canadas-paypal-mafia-the-surprising-afterlife-of-workbrain-the-2000s-era-startup-that-inspired-some-of-canadas-most-promising-tech-companies/. In Africa: Eric M. K. Osiakwan, “The

The Contrarian: Peter Thiel and Silicon Valley's Pursuit of Power

by Max Chafkin  · 14 Sep 2021  · 524pp  · 130,909 words

impressive as this entrepreneurial resume might be, Thiel has been even more influential as an investor and backroom deal maker. He leads the so-called PayPal Mafia, an informal network of interlocking financial and personal relationships that dates back to the late 1990s. This group includes Elon Musk, plus the founders of

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at the company’s driverless car division distributed stickers that proudly proclaimed, “Safety Third.” This was all, in a way, an extension of PayPal. “The PayPal Mafia philosophy became the founding principle for an entire generation of tech companies,” said McNamee. * * * — even so, in late 2000, Thiel wasn’t thinking about moving

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in the book “Peter sounds like Mel Gibson in Braveheart and my role is somewhere between negligible and a bad seed.” When Fortune gathered the PayPal Mafia for a Godfather-themed photo shoot—with Thiel styled to resemble Marlon Brando’s Don Corleone—Musk skipped the shoot, citing a prior commitment. “Peter

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San Francisco Peninsula that ultimately led to personal computers, websites, cryptocurrencies, smart watches, and really all of twenty-first-century capitalism. Fairchild employees, a PayPal Mafia before the PayPal Mafia, fanned out across the Valley, starting many of the most important tech companies and venture capital firms. In the popular imagination—colored by the

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-four teenagers and their parents to San Francisco. They were there to present ideas, listen to talks, mingle with fifty or so members of the PayPal Mafia, and compete with one another to be one of what would be twenty-four final winners. They’d been selected from a pool of about

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an unlikely sort of leader, but he’d been creating these networks based on loyalty for decades. Before the Thiel Fellowship there had been the PayPal Mafia, and before that there was the tiny crew of angry young college men he’d gathered at the Stanford Review. But now Thiel was working

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shape in 2010, when he began taking an interest in New Zealand’s tiny and relatively obscure tech scene. That year, the don of the PayPal Mafia made a $3 million investment in a little-known Wellington-based maker of accounting software. A friendly journalist for Business Insider showed up to explain

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industry it funded—was changing, in a way that threatened Thiel. He’d built his wealth to a great extent by cultivating a network—the PayPal Mafia—and using his rhetorical talents and contrarian instincts to further his influence, which earned him access to the most promising startups. But thanks to social

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Anslow, who’d once idolized Thiel, had dreamed of receiving an investment term sheet from Thiel. Now he flipped. Anslow proposed a sort of anti-PayPal Mafia, urging fellow startup-minded futurists to refuse to accept any capital from Thiel’s firms as part of a #NeverThiel movement. “My dream is to

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raised millions more to help Biden and the Democrats. Thiel and Hoffman may have their disagreements, but they remain close. The relationships forged by the PayPal Mafia will continue to pay off for years, if not decades. * * * — back in 2005, when Thiel was still trying on a new identity as a master

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an awareness of his own far-reaching influence. Thiel has surrounded himself with supporters and admirers who have protected him and enriched him. They—the PayPal Mafia, the Thielverse, and Silicon Valley itself, in all its hypocrisy and greed, and, yes, in its brilliance too—are part of his legacy. And yet

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with Reid Hoffman dates to their sophomore year at Stanford. Hoffman served as PayPal’s executive vice president and became a key player in the PayPal Mafia. Thiel saw potential in law school classmate Alex Karp, a left-wing bohemian who briefly pursued an academic career in Germany. When Karp returned to

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action committee of, 83–84 porn and, 81, 82, 86 World Domination Index of, 59–61, 76 X’s merger with, 65–67, 70–73 PayPal Mafia, xiii, xvi, 77, 121, 143, 161, 172, 211, 333, 335 PayPal Wars, The (Jackson), 96, 121 Pearson, Todd, 53, 60, 81, 83–84 Pell, Barney

Brotopia: Breaking Up the Boys' Club of Silicon Valley

by Emily Chang  · 6 Feb 2018  · 334pp  · 104,382 words

Copyright Dedication INTRODUCTION NOT JUST A PRETTY FACE: TECH’S ORIGINAL SIN CHAPTER 1 FROM NERD TO BRO: HOW TECH BYPASSED WOMEN CHAPTER 2 THE PAYPAL MAFIA AND THE MYTH OF THE MERITOCRACY CHAPTER 3 GOOGLE: WHEN GOOD INTENTIONS AREN’T ENOUGH CHAPTER 4 THE TIPPING POINT: WOMEN ENGINEERS SPEAK OUT CHAPTER

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instead of this alternate universe, we have seen the rise of the nerd-bro dream and the codification of an ultimate boys’ club. 2 THE PAYPAL MAFIA AND THE MYTH OF THE MERITOCRACY THE LAST TIME I interviewed Peter Thiel, we were onstage at the LendIt Conference in the spring of 2016

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interest in women’s status really matters, because Thiel isn’t just influential. He is the undisputed don of a group widely known as the PayPal Mafia, a cadre of men who constitute one of the many reasons Silicon Valley became so dominated by white men of a certain age and educational

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Thiel’s group at Stanford are worth reexamining because the ideas they formed in the 1990s inform the worldview they hold today. And given the PayPal Mafia’s outsized influence in Silicon Valley, this group of men’s worldview has affected our culture and changed a lot of lives. In the early

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with no technical background was the unlikely co-founder of what would become a billion-dollar start-up. And the group that would become the PayPal Mafia began to form. Sacks became PayPal’s COO in 1999. In early 2000, PayPal (then called Confinity) merged with a competing payments company called X

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job [at PayPal] without a connection to the company . . . We were very network-driven in hiring. And they were weird networks.” The members of the PayPal Mafia explicitly believed, and some still do, that hiring an ideologically diverse group of people early would slow the company down, when all they wanted to

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ticket to unprecedented opportunities and automatic success. Every one of them became very rich. Not one of them was a woman. A photograph of the PayPal Mafia on the cover of Fortune magazine in 2007 pictures the men posing as gamblers with cigars, drinks, and a deck of cards. “It just makes

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successful women at PayPal.” While they might not have been founders, these women, she says, were written out of history. Did the mythical status the PayPal Mafia acquired perpetuate the idea that successful start-ups were founded by groups of male friends? Was PayPal somehow responsible for this notion that women couldn

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’t or just didn’t found companies? “They absolutely created a template because having watched what the PayPal Mafia did and how incredibly successful they were. . . . Why wouldn’t you imitate them?” Roger McNamee, co-founder of the tech private equity firms Silver Lake

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meritocracy is laughable.” THE PAYPAL OCTOPUS The ultimate reach of the men in that Fortune cover photo is astonishing. After the sale to eBay, the PayPal Mafia unfurled like an octopus and deployed its tentacles all over Silicon Valley. Members were forever bonded by what they’d shared. As Thiel told me

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Zenefits was slashed amid the cheating scandal, it still reached $2 billion. (Sacks has since left Zenefits.) And this is just a partial list. The PayPal Mafia became so dominant that in 2017 Adam Pisoni—an entrepreneur who never worked at PayPal but was recruited by Sacks to be his Yammer co

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the major contributors to the lack of diversity” in Silicon Valley. “I am a product of the ‘PayPal Mafia dynasty,’” Pisoni wrote in a Medium post. “I co-founded Yammer with one of the original PayPal mafia members. Yammer had an easier time raising capital because of our PayPal connection.” Yammer, like PayPal, had

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of his Yammer connection, thus perpetuating the dominance of a selection of white men. Or as Roger McNamee sums it up, “Show me something the PayPal Mafia is not involved in.” Reid Hoffman also acknowledges how much he benefited simply by knowing Thiel. “Because Peter and I were classmates, that ended up

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problem. “I think it’s gotten worse, where people are hiring from their networks and their friends,” she says. “The money flows easily around [the PayPal Mafia] and hiring flows easily around that group, but I think that’s how labor markets work. The elite are connected with the elite . . . It’s

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benefit of hindsight, Affirm is very different,” he says. Thiel has made no such mea culpas. Indeed, in Zero to One, he embraces the term “PayPal Mafia,” a moniker that is deeply fraught with connotations of misogyny, male dominance, and the brutal exclusion of anyone outside the group. Zero to One has

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would-be entrepreneurs, all hoping to create their own billionaire mafia. A CRITIQUE OF MERITOCRACY Believing that they hired on merit from the start, the PayPal Mafia has evangelized that Silicon Valley epitomizes meritocracy. “If meritocracy exists anywhere on earth, it is in Silicon Valley,” David Sacks told the New York Times

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Sacks, who once wrote that if they hadn’t closed that round when they did, the company “would have died.” But the men of the PayPal Mafia succeeded often, with many other subsequent companies. Doesn’t that suggest that they earned it through merit? The concept of meritocracy dates back to the

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’s true skill and ability to do the job, that would be great for all workers, men and women. But the reality is, as the PayPal Mafia exemplifies, Silicon Valley is not a meritocracy. More fundamentally, meritocracy is impossible to achieve, because, as Young says, a meritocracy is always based on an

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greatest tech entrepreneurs: they were “all nerd” with big visions, yet their interest in hiring women, explicitly, set them apart from the tech bros and PayPal Mafia. Whether Google would have achieved the same level of success without hiring these key early women is impossible to know. But what is clear is

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isn’t beating you because they are working more hours than you, it’s because they are working smarter.” Not surprisingly, he encountered resistance. The PayPal Mafia member and venture capitalist Keith Rabois tersely tweeted in response, “Totally false.” Then elaborated in his next tweet: “Read a bio of Elon. Or about

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say you have an obligation to do that; not only is it legal, but you should have to.” Which brings me to a point the PayPal Mafia member Keith Rabois raised early in this book: he told me that it’s important to hire people who agree with your “first principles”—for

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Today, March 28, 2017, https://www.usatoday.com/story/tech/talkingtech/2017/03/28/tech-skills-gap-huge-graduates-survey-says/99587888. CHAPTER 2: THE PAYPAL MAFIA AND THE MYTH OF THE MERITOCRACY “a lucid and profound articulation”: Derek Thompson, “Peter Thiel’s Zero to One Might Be the Best Business Book

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are working more hours than you. It’s because they are working smarter,” Twitter post, May 29, 2017, https://twitter.com/blakeir/status/869275129712443393. The PayPal Mafia member: Keith Rabois (@rabois), “Totally false,” Twitter post, May 29, 2017, https://twitter.com/rabois/status/869292464120541184. “Read a bio of Elon”: Rabois, “Read a

Zero to One: Notes on Startups, or How to Build the Future

by Peter Thiel and Blake Masters  · 15 Sep 2014  · 185pp  · 43,609 words

is just what that looks like on the inside. BEYOND PROFESSIONALISM The first team that I built has become known in Silicon Valley as the “PayPal Mafia” because so many of my former colleagues have gone on to help each other start and invest in successful tech companies. We sold PayPal to

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had to be talented, but even more than that they had to be excited about working specifically with us. That was the start of the PayPal Mafia. RECRUITING CONSPIRATORS Recruiting is a core competency for any company. It should never be outsourced. You need people who are not just skilled on paper

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.2, 10.3, 10.4, 11.1, 11.2, 12.1, 12.2, 14.1 founders of, 14.1 future cash flows of investors in “PayPal Mafia” PCs Pearce, Dave penicillin perfect competition, 3.1, 3.2 equilibrium of Perkins, Tom perk war Perot, Ross, 2.1, 12.1, 12.2 pessimism

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finance. He has provided early funding for LinkedIn, Yelp, and dozens of successful technology startups, many run by former colleagues who have been dubbed the “PayPal Mafia.” He is a partner at Founders Fund, a Silicon Valley venture capital firm that has funded companies like SpaceX and Airbnb. He started the Thiel

Gilded Rage: Elon Musk and the Radicalization of Silicon Valley

by Jacob Silverman  · 9 Oct 2025  · 312pp  · 103,645 words

supporters and they had the cash to match. It seemed that Ramaswamy, then in his late thirties, was being drafted into Thiel’s so-called PayPal Mafia network, the influential group of mostly right-wing political donors and investors that sprang out of the payments startup PayPal. In Ramaswamy, the ruling cadre

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mansions around the country, including one on San Francisco’s Billionaires’ Row. Sacks was a core member of what’s frequently referred to as the PayPal Mafia—the web of influential PayPal alumni that included Sacks, Thiel, Elon Musk, Keith Rabois, Ken Howery, and a handful of others, most of them conservative

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-wing ideology was a constant, finding expression in conference keynotes, startup investments, and political fundraising. “It’s important to say that the genesis of the PayPal mafia is a political network, not a business network: It’s the Stanford Review,” journalist Max Chafkin told the Los Angeles Times’ Sam Dean. “This political

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. The country’s center of tech entrepreneurialism, however steeped in cultural liberalism, produced a thriving capitalist industry that made Sacks and the rest of the PayPal Mafia fabulously rich. But somewhere along the way, Sacks became repulsed by what he saw in San Francisco. An occasional financial supporter of Democratic politicians, he

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Hillbilly Elegy author. Both the donation and the endorsement were reportedly brokered by Thiel. On September 15, Sacks co-hosted a Republican fundraiser with fellow PayPal Mafia member Keith Rabois. Guests included serving Republican senators Rick Scott, Marco Rubio, and Chuck Grassley, and Republican candidates Masters, Vance, and Mehmet Oz. There were

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super PAC that would also be supported by Palantir co-founder Joe Lonsdale, Mark Zuckerberg castoffs Tyler and Cameron Winklevoss, and several members of the PayPal Mafia.14 Donning their “Dark MAGA” hats, the tech authoritarians were all in, and they were bringing their money with them. Two days later, sporting a

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Musk fixed that issue by doubling X’s character limit.) The éminence grise of the powerful network of investors and executives known informally as the PayPal Mafia, many of whom supported Donald Trump, Thiel spoke of politics—and death, for that matter—as something that could be “escaped,” leading to a utopian

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million worth of X through his nonprofit foundation. There were some notable names missing. Peter Thiel, Keith Rabois, and other pro-Trump members of the PayPal Mafia didn’t chip in, nor did Thiel’s Founders Fund—although, typical of the industry’s circular networks of cash and influence, Founders Fund was

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of here Page, Larry here Palantir here, here, here, here, here, here, here, here Palihapitiya, Chamath here, here, here, here, here PayPal here, here, here PayPal Mafia here, here, here, here Pelosi, Paul here Pence, Mike here, here Pennsylvania, and the 2024 election here Perez, Edward here Perkins, Tom here Peskin, Aaron

Elon Musk

by Walter Isaacson  · 11 Sep 2023  · 562pp  · 201,502 words

sharpness, which people just don’t expect from him, because they mistake him for a bullshitter or goofball.” 13 The Coup PayPal, September 2000 The PayPal mafia Luke Nosek, Ken Howery, David Sacks, Peter Thiel, Keith Rope, Reid Hoffman, Max Levchin, Roelof Botha; Max Levchin Michael Moritz Street fight By late summer

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earlier. Musk had taken his ouster with unusual calm, and he stayed friendly with the coup leaders, including Peter Thiel and Max Levchin. The old PayPal mafia, as they called themselves, were a tight-knit crowd. They helped finance their former colleague David Sacks—the friend who took notes for Antonio Gracias

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danger comes when artificial intelligence is decoupled from human will.” So Musk began hosting a series of dinner discussions that included members of his old PayPal mafia, including Thiel and Hoffman, on ways to counter Google and promote AI safety. He even reached out to President Obama, who agreed to a one

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, Max EM’s reconciliation with, 87, 183–84 on EM’s sense of mission, 94 Nosek and, 423 PayPal coup and, 82, 83, 86, 87 “PayPal mafia” and, 183 PayPal merger and, 76, 77, 78, 79, 81 PayPal recoding effort and, 79–80 Licklider, J. C. R., 399 LiDAR, 246, 406 Life

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, David, 523 EM’s management of Twitter and, 530–31, 576 EM’s reconciliation with, 87, 183 Gracias and, 157 PayPal coup and, 82, 83 “PayPal mafia” and, 183 politics and, 423–24, 529, 566 Starlink for Ukraine and, 433 Twitter acquisition and, 511 Sailor Moon, 415 Salzman, Alan, 138, 191–92

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reconciliation with, 87, 183–84 Founders Fund and, 183–84, 240 libertarianism and, 423 OpenAI and, 242 PayPal coup and, 82, 83–84, 85, 86 “PayPal mafia” and, 183 PayPal merger and, 76, 77, 78, 79 Trump and, 261 Thompson, Chris, 149, 150, 151, 185 three musketeers (Twitter). See Musk, Andrew; Musk

The Unwinding: An Inner History of the New America

by George Packer  · 4 Mar 2014  · 559pp  · 169,094 words

for $1.5 billion. Thiel quit the same day, walking away with $55 million on his $240,000 investment. What came to be called the PayPal mafia went on to found a lot of successful companies: YouTube, LinkedIn, Tesla Motors, SpaceX, Yelp, Yammer, Slide … Thiel moved out of his one-bedroom apartment

The Start-Up of You: Adapt to the Future, Invest in Yourself, and Transform Your Career

by Reid Hoffman and Ben Casnocha  · 14 Feb 2012  · 176pp  · 55,819 words

informal collaboration. Yet these connections have spawned some of the most successful projects in Silicon Valley. As a result, the group got the name “the PayPal mafia.” What is it about this network that makes it such a uniquely rich source of opportunities? First, each individual is high-quality. This is fundamental

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from Socialnet, a former college classmate, and a former colleague from Fujitsu to cofound the company with me. Peter Thiel and Keith Rabois from the PayPal mafia and a few others invested in the business. A former colleague from PayPal even provided LinkedIn’s first office space. An appropriate founding for a

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business with the tagline RELATIONSHIPS MATTER. To recap some of the qualities of the PayPal mafia: high-quality people, a common bond, an ethos of sharing and cooperation, concentrated in a region and industry. These make it rich in opportunity flow

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your while. Finally, the only thing better than joining groups is starting your own. Start your own mafia—your own group, meetup, or association with PayPal mafia characteristics. Once a year I co-organize something I call the Weekend to Be Named Later, a Franklin-inspired gathering of ambitious friends, to brainstorm

Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future

by Ashlee Vance  · 18 May 2015  · 370pp  · 129,096 words

DEDICATION For Mum and Dad. Thanks for Everything. CONTENTS DEDICATION 1 ELON’S WORLD 2 AFRICA 3 CANADA 4 ELON’S FIRST START-UP 5 PAYPAL MAFIA BOSS 6 MICE IN SPACE PHOTOGRAPHIC INSERT 7 ALL ELECTRIC 8 PAIN, SUFFERING, AND SURVIVAL 9 LIFTOFF 10 THE REVENGE OF THE ELECTRIC CAR 11

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was concerned, they were all wrong, and he set out to prove his point with what would end up being even more dramatic results. 5 PAYPAL MAFIA BOSS THE SALE OF ZIP2 INFUSED ELON MUSK WITH A NEW BRAND OF CONFIDENCE. Much like the video-game characters he adored, Musk had leveled

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terrorists and of software used by the world’s largest banks to combat crime. This collection of super-bright employees has become known as the PayPal Mafia—more or less the current ruling class of Silicon Valley—and Musk is its most famous and successful member. Hindsight also continues to favor Musk

Zucked: Waking Up to the Facebook Catastrophe

by Roger McNamee  · 1 Jan 2019  · 382pp  · 105,819 words

PayPal proved to have much greater impact. Peter Thiel, Elon Musk, Reid Hoffman, Max Levchin, Jeremy Stoppleman, and their colleagues were collectively known as the PayPal Mafia, and their impact transformed Silicon Valley. Not only did they launch Tesla, Space-X, LinkedIn, and Yelp, they provided early funding to Facebook and many

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other successful players. More important than the money, though, were the vision, value system, and connections of the PayPal Mafia, which came to dominate the social media generation. Validation by the PayPal Mafia was decisive for many startups during the early days of social media. Their management techniques enabled startups to grow at

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rates never before experienced in Silicon Valley. The value system of the PayPal Mafia helped their investments create massive wealth, but may have contributed to the blindness of internet platforms to harms that resulted from their success. In short

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, we can trace both the good and the bad of social media to the influence of the PayPal Mafia. * * * — THANKS TO LUCKY TIMING, Facebook benefitted not only from lower barriers for startups and changes in philosophy and economics but also from a new social

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, 161, 187–89, 191, 192, 242 Pariser, Eli, 66–67, 109 Parkland school shooting, 174 passwords and log-ins, 249–50, 271 PayPal, 48, 249 PayPal Mafia, 48 Parker, Sean, 38, 54, 55, 64, 147–49 Pearlman, Bret, 14 Pelosi, Nancy, 167, 227 personalization, 105 persuasive techniques, 17, 83–84, 96–99

Bitcoin Billionaires: A True Story of Genius, Betrayal, and Redemption

by Ben Mezrich  · 20 May 2019  · 304pp  · 91,566 words

Palo Alto: A History of California, Capitalism, and the World

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The Power Law: Venture Capital and the Making of the New Future

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Insane Mode: How Elon Musk's Tesla Sparked an Electric Revolution to End the Age of Oil

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The Industries of the Future

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The Optimist: Sam Altman, OpenAI, and the Race to Invent the Future

by Keach Hagey  · 19 May 2025  · 439pp  · 125,379 words

Decoding the World: A Roadmap for the Questioner

by Po Bronson  · 14 Jul 2020  · 320pp  · 95,629 words

We Are the Nerds: The Birth and Tumultuous Life of Reddit, the Internet's Culture Laboratory

by Christine Lagorio-Chafkin  · 1 Oct 2018

Exponential Organizations: Why New Organizations Are Ten Times Better, Faster, and Cheaper Than Yours (And What to Do About It)

by Salim Ismail and Yuri van Geest  · 17 Oct 2014  · 292pp  · 85,151 words

Don't Be Evil: How Big Tech Betrayed Its Founding Principles--And All of US

by Rana Foroohar  · 5 Nov 2019  · 380pp  · 109,724 words

Traffic: Genius, Rivalry, and Delusion in the Billion-Dollar Race to Go Viral

by Ben Smith  · 2 May 2023

Valley of Genius: The Uncensored History of Silicon Valley (As Told by the Hackers, Founders, and Freaks Who Made It Boom)

by Adam Fisher  · 9 Jul 2018  · 611pp  · 188,732 words

Genius Makers: The Mavericks Who Brought A. I. To Google, Facebook, and the World

by Cade Metz  · 15 Mar 2021  · 414pp  · 109,622 words

Pattern Breakers: Why Some Start-Ups Change the Future

by Mike Maples and Peter Ziebelman  · 8 Jul 2024  · 207pp  · 65,156 words

Unit X: How the Pentagon and Silicon Valley Are Transforming the Future of War

by Raj M. Shah and Christopher Kirchhoff  · 8 Jul 2024  · 272pp  · 103,638 words

Billionaire, Nerd, Savior, King: Bill Gates and His Quest to Shape Our World

by Anupreeta Das  · 12 Aug 2024  · 315pp  · 115,894 words

Big Data: A Revolution That Will Transform How We Live, Work, and Think

by Viktor Mayer-Schonberger and Kenneth Cukier  · 5 Mar 2013  · 304pp  · 82,395 words

Artificial Unintelligence: How Computers Misunderstand the World

by Meredith Broussard  · 19 Apr 2018  · 245pp  · 83,272 words

Capitalism Without Capital: The Rise of the Intangible Economy

by Jonathan Haskel and Stian Westlake  · 7 Nov 2017  · 346pp  · 89,180 words

Moral Ambition: Stop Wasting Your Talent and Start Making a Difference

by Bregman, Rutger  · 9 Mar 2025  · 181pp  · 72,663 words

Startup Communities: Building an Entrepreneurial Ecosystem in Your City

by Brad Feld  · 8 Oct 2012  · 169pp  · 56,250 words

Reentry: SpaceX, Elon Musk, and the Reusable Rockets That Launched a Second Space Age

by Eric Berger  · 23 Sep 2024  · 375pp  · 113,230 words

Breaking Twitter: Elon Musk and the Most Controversial Corporate Takeover in History

by Ben Mezrich  · 6 Nov 2023  · 279pp  · 85,453 words

The New Map: Energy, Climate, and the Clash of Nations

by Daniel Yergin  · 14 Sep 2020

Attention Factory: The Story of TikTok and China's ByteDance

by Matthew Brennan  · 9 Oct 2020  · 282pp  · 63,385 words

Whole Earth: The Many Lives of Stewart Brand

by John Markoff  · 22 Mar 2022  · 573pp  · 142,376 words