The online payments company PayPal created a network of wealthy entrepreneurs who would come to exert significant influence over 21st-century politics, technology, and venture capital -- including [[Peter Thiel]], [[Elon Musk]], [[David Sacks]], [[Keith Rabois]], Reid Hoffman, and many others who have shaped both Silicon Valley and the American political landscape. - December 1998 -- The company is originally founded as Confinity, a handheld device security software vendor - 1999 -- Confinity pivots to develop a digital wallet service - March 2000 -- Confinity merges with [[Elon Musk]]'s X.com financial services company - October 2000 -- Musk decides to scrap non-PayPal parts of the business, and is replaced by Thiel as CEO of X.com - 2002 -- Meg Whitman, then eBay's CEO, moves to acquire [[PayPal]] for $1.5 billion ## The Founding Years (1998-2002) **December 1998** — Confinity is founded by Max Levchin, [[Peter Thiel]], and Luke Nosek as a handheld device security software vendor, initially focused on encryption software for Palm Pilots.[](https://quartr.com/insights/company-research/the-paypal-story-online-payment-pioneers)​ **1999** — Confinity pivots to develop a digital wallet service, launching the PayPal product in late 1999. The service enables users to transfer money electronically between devices and via email addresses.[](https://en.wikipedia.org/wiki/Confinity)​ **March 2000** — Confinity merges with [[Elon Musk]]'s X.com online banking company in a 50-50 deal. The combined entity is initially called X.com, with Bill Harris remaining as CEO and Musk as Chairman.[](https://timelines.issarice.com/wiki/Timeline_of_PayPal)​ **April 2000** — Bill Harris is ousted as CEO. Musk takes over as CEO while Thiel becomes Chairman.[](https://timelines.issarice.com/wiki/Timeline_of_PayPal)​ **September 2000** — While Musk is on his honeymoon in Australia, a coup organized by Max Levchin, Peter Thiel, Reid Hoffman, and [[David Sacks]] results in Musk's removal as CEO. Peter Thiel returns as CEO. The primary disputes centered on branding (Musk wanted to keep the X.com name while others favored PayPal) and technical disagreements about fraud prevention.[](https://www.foxbusiness.com/markets/elon-musk-dethroned-peter-thiel-coup-led-paypal-mafia)​ **2001** — The company is officially rebranded as PayPal, abandoning the X.com name.[](https://quartr.com/insights/company-research/the-paypal-story-online-payment-pioneers)​ **February 15, 2002** — PayPal goes public on Nasdaq with an IPO price of $13 per share, raising $70.2 million. The stock surges 55% on its first day of trading to close at $20.09, making it the first internet company to go public in almost a year.[](https://www.wired.com/2002/02/paypal-ipo-omen-or-anomaly/)​ **July 8, 2002** — eBay under then-CEO Meg Whitman announces it will acquire PayPal for $1.5 billion in a stock-for-stock transaction. The deal values PayPal at 0.39 eBay shares per PayPal share.[](https://www.sec.gov/Archives/edgar/data/1103415/000091205702037693/a2090698zex-99_1.htm)​ **October 3, 2002** — The eBay acquisition of PayPal closes, with approximately 65% of PayPal stockholders approving the deal. Peter Thiel resigns as CEO, and Matt Bannick of eBay assumes his responsibilities. Within four years, all but 12 of the first 50 PayPal employees leave the company, but they remain connected as social and business acquaintances.[](https://en.wikipedia.org/wiki/PayPal_Mafia)​ ## The Post-PayPal Empire Building (2002-2010) **May 2002** — Elon Musk founds SpaceX (Space Exploration Technologies Corporation) on March 14, 2002, investing $100 million from his PayPal proceeds. The company's goal is to reduce space transportation costs and enable Mars colonization.[](https://www.perplexity.ai/page/spacex-s-founding-story-fhrxmPscS1iSq6Zqd6y2Kg)​ **May 2003** — Peter Thiel incorporates [Palantir Technologies](https://doctorparadox.net/what-is-palantir/), a [[big data]] analysis company focused on counterterrorism and intelligence work. The company is initially funded by Thiel and receives $2 million from In-Q-Tel, the CIA's investment arm. Co-founders include Alex Karp, [Joe Lonsdale](https://doctorparadox.net/people-data/who-is-joe-lonsdale/), Stephen Cohen, and Nathan Gettings.[](https://en.wikipedia.org/wiki/Palantir_Technologies)​ **May 5, 2003** — Reid Hoffman officially launches LinkedIn, the professional networking platform he co-founded with Allen Blue, Konstantin Guericke, Eric Ly, and Jean-Luc Vaillant. The company started in Hoffman's living room in 2002 and had 4,500 members by the end of its first month.[](https://press.linkedin.com/content/dam/press/images/news-releases/acquisition/linkedin-fact-sheet.pdf)​ **July 2004** — Jeremy Stoppelman and Russel Simmons co-found Yelp with $1 million in seed funding from Max Levchin at MRL Ventures. The company initially launches as an email-based referral network before pivoting to user-generated reviews.[](https://siebelschool.illinois.edu/about/awards/alumni-awards/alumni-awards-past-recipients/russ-simmons)​ **2005** — Peter Thiel, Ken Howery, and Luke Nosek found Founders Fund, raising their first $50 million from individual entrepreneurs and angel investors. The firm adopts a "founder-centric" philosophy and goes on to make early investments in SpaceX, [Facebook](https://doctorparadox.net/category/technology/facebook/), and other transformative companies.[](https://www.chaincatcher.com/en/article/2192085)​ **February 14, 2005** — YouTube is founded by former PayPal employees Chad Hurley, Steve Chen, and Jawed Karim. Karim uploads the first video, "Me at the zoo," on April 23, 2005. The platform was initially conceived as a video dating site before pivoting to general video sharing.[](https://surgegraph.io/business/who-owns-youtube-company)​ **2006** — Sean Parker joins Founders Fund as a partner.[](https://en.wikipedia.org/wiki/Founders_Fund)​ **October 9, 2006** — Google acquires YouTube for $1.65 billion in stock, providing the young company with resources to handle copyright challenges and scale its infrastructure.[](https://www.fastcompany.com/91408036/youtube-google-acquisition-2006-steve-chen-eric-schmidt-ate-tv-oral-history)​ **2007** — Fortune magazine publishes its iconic "PayPal Mafia" article featuring a photo of 13 former PayPal employees dressed in gangster attire, formally coining the term that would define this influential group.[](https://observer.com/2025/10/paypal-cofounders-today/)​ **2007** — [[David Sacks]] founds Geni.com, a family genealogy and social networking site.[](https://thenextweb.com/news/family-oriented-social-network-raises-25-million-and-buys-its-main-rival-geni)​ **2008** — David Sacks founds Yammer, an enterprise social networking service modeled after [[Twitter]] for businesses.[](https://techcrunch.com/2012/06/25/its-official-microsoft-confirms-it-has-acquired-yammer-for-1-2-billion-in-cash/)​ ## Expanding Influence and Political Engagement (2010-2020) **2011** — LinkedIn goes public on the New York Stock Exchange, with Reid Hoffman's stake valued at an estimated $2.34 billion.[](https://www.frederick.ai/blog/reid-hoffman-linkedin)​ **June 2012** — [[Microsoft]] acquires Yammer for $1.2 billion in cash. David Sacks remains as CEO, with Yammer operating as part of Microsoft's Office Division.[](https://techcrunch.com/2012/09/12/david-sacks-on-selling-yammer-we-never-really-shopped-the-company/)​ **November 2012** — MyHeritage acquires Geni.com in an eight-figure deal combining cash and equity. David Sacks joins MyHeritage's board of directors.[](https://techcrunch.com/2012/11/28/all-in-the-family-myheritage-buys-former-yammer-stablemate-geni-com-raises-25m/)​ **2016** — Peter Thiel becomes one of Donald Trump's most prominent [Silicon Valley](https://doctorparadox.net/tag/silicon-valley/) supporters, speaking at the [[Republican National Committee (RNC)]]'s annual event and donating $1.25 million to Trump's campaign through super PAC contributions and direct donations. This marks Thiel as the sole notable tech sector advocate for Trump's candidacy.[](https://www.nytimes.com/2016/10/16/technology/peter-thiel-donald-j-trump.html)​ **June 2016** — Microsoft acquires LinkedIn for $26.2 billion, one of the largest acquisitions in the tech industry.[](https://www.frederick.ai/blog/reid-hoffman-linkedin)​ **2016** — Dave McClure, founder of 500 Startups, launches "Nerdz 4 Hillary" to rally Silicon Valley support for Hillary Clinton, positioning himself in opposition to Trump-supporting PayPal Mafia members like Peter Thiel.[](https://fortune.com/2016/09/28/clinton-silicon-valley-fundraising/)​ ## The Trump Era and Political Ascendancy (2017-2025) **2017** — Peter Thiel joins Trump's transition team as a member of the executive committee in November 2016, raising ethical concerns about potential conflicts of interest between Silicon Valley and government regulation.[](https://therevolvingdoorproject.org/billionaires-and-the-trump-admin-peter-thiel/)​ **2017** — Ken Howery serves as U.S. Ambassador to Sweden during Trump's first term, defending Trump's unconventional NATO approach.[](https://www.arctictoday.com/trumps-ambassador-tasked-with-getting-greenland-confirmed/)​ **2017** — JD Vance joins Peter Thiel's venture capital firm Mearl Investment Partners. Thiel hires Vance after he had worked at a law firm following the success of his book "Hillbilly Elegy."[](https://www.politico.com/news/2022/05/03/jd-vance-win-ohio-primary-00029881)​ **2019** — JD Vance returns to Ohio and starts his own venture capital firm, heavily backed by Peter Thiel and other elite tech investors.[](https://www.cbsnews.com/news/jd-vance-trump-vp-peter-thiel-billionaire/)​ **2020** — Palantir goes public through a direct listing. Peter Thiel distances himself from Trump and does not donate to his re-election campaign, reportedly believing the campaign was doomed due to COVID-19's economic impact.[](https://www.motherjones.com/politics/2025/07/peter-thiel-republican-donations-palantir-federal-contracts-house-control-trump/)​ **2021** — Peter Thiel brings JD Vance to his first meeting with Trump at Mar-a-Lago in February.[](https://www.cbsnews.com/news/jd-vance-trump-vp-peter-thiel-billionaire/)​ **May 3, 2022** — JD Vance wins the Ohio Republican Senate primary with crucial support from Peter Thiel, who donated a record-breaking $15 million to the pro-Vance super PAC "Protect Ohio Values". This represents the largest amount ever given to boost a single Senate candidate at that time.[](https://www.usatoday.com/story/news/politics/elections/2024/07/17/peter-thiel-boosted-jd-vance-career/74397520007/)​ **August 2, 2022** — Blake Masters wins the Arizona Republican Senate primary, backed by $15 million from Peter Thiel to the "Saving Arizona" super PAC. Masters, a former COO of Thiel Capital and co-author of "Zero to One" with Thiel, secured Trump's endorsement.[](https://www.npr.org/sections/2022-live-primary-election-race-results/2022/08/03/1115185686/blake-masters-trump-pick-funded-by-billionaire-thiel-wins-arizona-senate-primary)​ **November 2022** — Blake Masters loses the general election to incumbent Democrat [Mark Kelly](https://www.kelly.senate.gov/), receiving the fewest votes among all statewide Republican candidates in Arizona. JD Vance wins his Ohio Senate race and enters the U.S. Senate.[](https://en.wikipedia.org/wiki/Blake_Masters)​ **February 2023** — Peter Thiel makes his first publicly disclosed political contribution in two and a half years, giving $852,200 to House Speaker Mike Johnson's "Grow the Majority" joint fundraising committee. The money is then distributed to the Republican National Committee, House Republicans' campaign arm, over a dozen state parties, and nearly 30 GOP House members.[](https://www.businessinsider.com/peter-thiel-spending-money-politics-again-house-republicans-2025-7)​ **2024** — The PayPal Mafia emerges as a dominant force in the 2024 presidential election. Elon Musk donates approximately $288-290 million to support Trump and Republican candidates, making him the largest political donor of the 2024 cycle. Peter Thiel, while not directly donating to Trump's 2024 campaign, supports congressional Republicans and backs JD Vance's selection as Trump's running mate.[](https://www.nbcnews.com/politics/2026-election/elon-musk-gives-millions-republican-super-pacs-ahead-midterms-rcna222114)​ **July 2024** — Trump selects JD Vance as his vice presidential running mate, cementing the PayPal Mafia's influence in the Republican Party. Vance, often described as Peter Thiel's protégé, had benefited from $15 million in Thiel support during his 2022 Senate campaign.[](https://en.wikipedia.org/wiki/PayPal_Mafia)​ **November 2024** — Trump wins the presidential election with significant support from the PayPal Mafia. Reid Hoffman, representing the Democratic faction of the group, had spent over $9 million supporting Democrats in Wisconsin alone since 2020 and donated $2 million to [Biden](https://doctorparadox.net/biden-tech-industrial-complex/)'s New Hampshire write-in campaign.[](https://www.forbes.com/sites/saradorn/2024/01/31/billionaire-reid-hoffman-spent-2-million-on-bidens-new-hampshire-write-in-campaign-fec-records-show/)​ **December 5, 2024** — Trump names David Sacks as White House [[artificial intelligence (AI)]] and Crypto Czar, a newly created position. Sacks, who hosted a major Trump fundraiser and spoke at the Republican National Convention, is tasked with creating a legal framework for the cryptocurrency industry and leading the President's Council of Advisors on Science and Technology.[](https://en.wikipedia.org/wiki/David_O._Sacks)​ **December 21, 2024** — Trump announces Ken Howery as his nominee for U.S. Ambassador to the Kingdom of Denmark, explicitly linking the appointment to his desire for "ownership and control of Greenland". Trump states this is an "absolute necessity" for national security.[](https://www.presidency.ucsb.edu/documents/statement-president-elect-donald-j-trump-announcing-the-nomination-ken-howery-ambassador)​ ## The Second Trump Administration (2025) **January 2025** — [Elon Musk is appointed to lead the Department of Government Efficiency (DOGE)](https://doctorparadox.net/why-are-people-protesting-elon-musk-doge/), a new advisory body tasked with cutting $500 billion from the U.S. federal budget. Musk dominates early Cabinet meetings and is referred to by critics as a "de facto, unelected co-president".[](https://techpolicy.press/tracking-elon-musks-political-activities)​ **February 2025** — Peter Thiel and Palantir begin collaborating with Elon Musk's Department of Government Efficiency for the second Trump administration.[](https://en.wikipedia.org/wiki/PayPal_Mafia)​ **March 2025** — Trump signs an executive order calling for federal data sharing across agencies, [positioning Palantir as the primary software provider for government data integration](https://doctorparadox.net/why-are-people-protesting-elon-musk-doge/). Palantir receives more than $113 million in federal government spending in the first months of the Trump administration.[](https://www.wired.com/story/palantir-government-contracting-push/)​ **May 2025** — Elon Musk resigns from his formal advisory role amid a harsh public fight with Trump over [the budget bill](https://doctorparadox.net/gop-budget-bill-debt-for-no-good-reason/), though he continues political involvement. Later that month, Musk announces he plans to scale back political spending, stating "I think I've done enough".[](https://www.politico.com/news/2025/07/31/elon-musk-donations-clf-slf-00487699)​ **May 2025** — The Pentagon awards Palantir a $795 million contract to enhance its Maven Smart System initiative.[](https://www.nytimes.com/2025/05/30/technology/trump-palantir-data-americans.html)​ **June 27, 2025** — Despite his acrimonious White House departure, Elon Musk donates $5 million each to the primary super PACs supporting House and Senate Republicans, making him the largest individual contributor to these organizations in the first half of 2025. Days later, Musk begins publicly contemplating establishing a new political party.[](https://www.nbcnews.com/politics/2026-election/elon-musk-gives-millions-republican-super-pacs-ahead-midterms-rcna222114)​ **July 2025** — Peter Thiel resumes active political giving after sitting out the 2024 cycle, focusing on helping Republicans preserve their House majority. He gives $852,200 to Speaker Mike Johnson's PAC, which distributes funds to competitive House races.[](https://www.businessinsider.com/peter-thiel-spending-money-politics-again-house-republicans-2025-7)​ **August 1, 2025** — Palantir wins a $10 billion U.S. Army software and data contract, consolidating 75 separate contracts into a single enterprise agreement. Palantir has become one of the few major winners in Trump's cost-cutting efforts, with its U.S. government revenue surging by more than $370 million compared to the previous year.[](https://www.cnbc.com/2025/08/01/palantir-lands-10-billion-army-software-and-data-contract.html)​ **October 7, 2025** — The U.S. Senate confirms Ken Howery 51-47 as Ambassador to Denmark, with an explicit mandate to pursue Trump's Greenland acquisition goals. Howery, a co-founder of PayPal and Founders Fund with Peter Thiel, becomes a key diplomatic player in one of Trump's most controversial foreign policy initiatives.[](https://www.financialexpress.com/world-news/ken-howery-from-silicon-valley-investor-to-key-player-in-trumps-greenland-push/3717644/)​ ## Key Political Alignments Within the PayPal Mafia **Conservative/Libertarian/Trump-Aligned Faction:** - **[[Peter Thiel]]** — The "don" of the PayPal Mafia, donated $1.25 million to Trump in 2016, spent $30 million on JD Vance and Blake Masters in 2022, and has resumed political giving in 2025 focused on House Republicans[](https://www.businessinsider.com/paypal-mafia-members-elon-musk-peter-thiel-reid-hoffman-companies)​ - **[[Elon Musk]]** — Donated $277-290 million to Trump and Republicans in 2024, appointed to lead DOGE in 2025[](https://www.tandfonline.com/doi/full/10.1080/17530350.2025.2471602)​ - **[[David Sacks]]** — Trump's AI and Crypto Czar, hosted Trump fundraiser and spoke at Republican National Convention in 2024[](https://www.science.org/content/article/trump-s-pick-ai-czar-signals-support-science-advisory-panel)​ - **Ken Howery** — Co-founder of Founders Fund, served as Ambassador to Sweden in Trump's first term, confirmed as Ambassador to Denmark in 2025 with Greenland mandate[](https://www.everythingstartups.com/vc-funds/founders-fund)​ - **Luke Nosek** — Co-founder of Founders Fund, his wife Nicole Nosek contributed $100,000 to YIMBY causes in San Francisco[](https://theaustinindependent.org/california-transplant-high-tech-billionaires-and-leslie-pools-home-initiative/)​ - **[[Keith Rabois]]** — Has donated hundreds of thousands to House Republicans in recent cycles, including nearly $700,000 to "Protect the House" in 2023. Donated $50,000 to NeverTrump PAC in 2016 but has since aligned with Republican causes[](https://abcnews.go.com/US/nikki-haley-nabs-fundraiser-gop-donor-previously-supported/story?id=104046855)​ - **JD Vance** — Though not an original PayPal employee, Vance is Peter Thiel's protégé and Vice President in the second Trump administration[](https://www.politico.com/news/2022/05/03/jd-vance-win-ohio-primary-00029881)​ **Democratic/Progressive Faction:** - **Reid Hoffman** — Major Democratic donor who has made over 800 political contributions, nearly all to Democrats. Pledged to donate $100 million to oppose Trump in 2020. Donated nearly $9 million to Wisconsin Democrats since 2020 and $2 million to Biden's New Hampshire write-in campaign in 2024. Has also funded anti-Trump efforts including supporting Nikki Haley's primary campaign and backing the Lincoln Project[](https://www.influencewatch.org/person/reid-hoffman-2/)​ - **Jeremy Stoppelman** (Yelp CEO) — Donated over $71,000 to Obama's reelection campaign and to Democratic parties. Has given $300,000 to local San Francisco progressive causes[](https://thehill.com/policy/technology/194339-yelp-starts-pac-for-political-donations/)​ - **Max Levchin** — Co-founder of Affirm who has generally avoided public political statements, though he condemned the January 6 Capitol insurrection as a "disgrace" and has been involved with FWD.us, a Silicon Valley lobbying group focused on immigration reform[](https://finance.yahoo.com/news/maga-hat-wearers-use-tech-software-too-morning-brief-123052785.html)​ - **Dave McClure** (500 Startups founder) — Launched "Nerdz 4 Hillary" campaign in 2016 to rally tech support for Clinton, explicitly opposing Trump-supporting figures like Peter Thiel[](https://www.wired.com/story/dave-mcclure-500-startups-the-anti-vc/)​ **Neutral/Low Political Profile:** - **Roelof Botha** (Sequoia Capital) — Has stated Sequoia takes no political position and that he is not registered with either party. However, faced internal controversy in 2025 over a partner's inflammatory political posts[](https://fortune.com/2024/07/16/sequoia-roelof-botha-vc-firm-wont-take-sides-election-unhealthy-partisan-divide-brainstorm-tech/)​ - **Steve Chen, Chad Hurley, Jawed Karim** (YouTube founders) — Have maintained low political profiles with no significant public political involvement documented - **Russel Simmons** (Yelp co-founder) — No significant political activity documented ## The PayPal Mafia's Broader Impact The PayPal Mafia's influence extends far beyond their original company. Members have founded or invested in YouTube, LinkedIn, Yelp, SpaceX, Tesla, Palantir, Facebook, Airbnb, Stripe, Lyft, Square, Reddit, [[OpenAI]], Pinterest, Tumblr, and hundreds of other companies. Their venture capital firm Founders Fund alone manages approximately $12 billion in assets as of 2023.[](https://fleximize.com/paypal-mafia/)​ Their political influence has grown particularly pronounced in the second Trump administration, leading _The Economist_ to write that the PayPal Mafia would "take over America's government" following Trump's 2024 victory. With Elon Musk leading DOGE, JD Vance as Vice President, David Sacks as AI and Crypto Czar, Ken Howery as Ambassador to Denmark, and Palantir securing billions in government contracts, the group that started as online payment entrepreneurs has become one of the most powerful political forces in America.[](https://www.investopedia.com/the-paypal-mafia-8759491)​ The group represents a fundamental shift in American politics, where tech billionaires with libertarian and conservative leanings have moved from the periphery to the center of Republican power. Meanwhile, the Democratic faction of the PayPal Mafia, particularly Reid Hoffman, has emerged as a counterbalance, pouring tens of millions into Democratic campaigns and anti-Trump efforts. This ideological split within the PayPal Mafia reflects broader tensions in Silicon Valley and American politics about the role of technology, regulation, and concentrated wealth in shaping the nation's future.