Peter Thiel cofounded the company that would become Paypal — called Confinity — in 1999 alongside Max Levchin and Luke Nosek. Confinity was launched as a developer of security software for hand-held devices like the PalmPilot, but it later pivoted toward digital money transfers. 

Thiel served as CEO of PayPal until October 2002, when eBay acquired the company for $1.5 billion. Thiel's 3.7% stake was worth a $55 million, according to SEC filings.

Thiel, now a billionaire with a net worth of $15.9 billion, according to Bloomberg, cofounded the big data analysis firm Palantir in 2003. He was the first major outside investor in Facebook and contributed early funding to Yelp and LinkedIn, along with a number of other ventures launched by his PayPal peers. Thiel's also a partner of Founders Fund, a venture capital fund based in San Francisco.

Thiel has also drawn criticism in recent years for his support of President Donald Trump and for secretly funding Hulk Hogan's lawsuit against Gawker Media, which resulted in the company shutting down Gawker and selling the company's assets.

After facilitating talks between Trump and now Sen. JD Vance, Thiel gave a record-breaking $15 million to Vance's campaign, the largest donation ever given to a single senate candidate. 

Thiel later told The Atlantic he was taking a break from politics. Business Insider later reported that he served as an FBI informant.

While his and Trump's relationship has reportedly soured, Trump's recent announcement of Vance as his vice president pick has put Thiel back to playing kingmaker.

Max Levchin is sometimes called the "consigliere" of the PayPal Mafia — in "The Godfather," a consigliere is an advisor to the boss.

Levchin made significant contributions to PayPal's anti-fraud efforts. Together with PayPal technical architect David Gausebeck, he helped create the Gausebeck-Levchin test, an early version of a CAPTCHA for commercial applications.

After PayPal was bought by eBay, Levchin founded a media-sharing service called Slide that was later bought by Google. He was also an early investor in Yelp — at one point he was the company's largest shareholder — and he served as chairman of Yelp from its founding in 2004 until July 2015.

He founded fintech company Affirm, which allows consumers to finance online purchases at the point of sale and pay for them over time. Affirm went public in 2021, raising $1.2 billion in its IPO. Levchin is also the chairman of Glow, a fertility-tracking app that helps users improve their odds of conceiving.

After eBay bought PayPal, Howery stayed on as eBay's director of corporate development until 2003. After PayPal's acquisition, he served as cofounder and partner of Founders Fund alongside Peter Thiel.

He was appointed by former President Trump in January 2019 and confirmed in September of that year. He also donated $1 million earlier this year to America PAC, a pro-Trump super PAC created by fellow PayPal mafia member Elon Musk.

Howery is active in several nonprofits and serves as a founding advisor to Kiva, an organization that facilitates loans to low-income entrepreneurs. Kiva was founded in part by Premal Shah, PayPal's former product manager.

Howery is reportedly still good friends with Elon Musk. 

In 1999, Elon Musk founded a payments company called X.com, which merged with Thiel's Confinity in 2000. He briefly served as CEO of PayPal before he was ousted by the board in September 2000 and replaced with Thiel. But as the company's largest shareholder, he still walked away from the PayPal sale to eBay with a cool $165 million.

Perhaps the best-known of all the members of the PayPal mafia now, Musk's estimated net worth is $362 billion.

Since his PayPal days, Musk has moved on to oversee companies like Tesla, SpaceX, the Boring Company, and Neuralink. He also bought Twitter and renamed it X, after buying back the X.com domain name from PayPal. 

Musk, who has been a vocal supporter of Trump's 2024 presidential campaign and donated more than $200 million to Republican election efforts, will also co-lead the newly created Department of Government Efficiency alongside former Republican presidential candidate Vivek Ramaswamy, Trump announced after winning the election.

Nosek was also reportedly the person who clued in Peter Thiel to cryogenic preservation, which Thiel has since invested in heavily.

In 2005, Nosek joined Thiel and Howery as a partner at Founders Fund. In 2017, Nosek left Founders Fund to launch investment firm Gigafund, which helped raise money for SpaceX.

Nosek was also the first institutional investor in SpaceX and is a board member. He also joined the board of ResearchGate, a platform where scientists and researchers can ask questions, follow topics, and review one another's papers.

Botha went to school to be an actuary. He said he never planned to get into tech, but when he saw the opportunity in Silicon Valley, his intuition told him it was where he needed to be.

He started as PayPal's director of corporate development, went on to become vice-president of finance, and later served as CFO.

Botha is now considered one of the top tech investors in the world.

Sequoia Capital has funded tech giants like Apple, Google, YouTube, and Instagram. 

Botha as served on the board at more than a dozen companies, including Square, EventBrite, Weebly, Tumblr, Instagram, YouTube, as well as 23andMe, which he resigned alongside the rest of the board in September over CEO Anne Wojcicki's proposal to take the company private.

LinkedIn cofounder Reid Hoffman served on the board of directors when PayPal was founded.

He eventually joined the company full-time as PayPal's COO. In a New York Times interview, Peter Thiel referred to Hoffman as PayPal's "firefighter in chief," noting that there were many fires that needed putting out in the company's early days.

When PayPal was acquired by eBay, Hoffman was the company's executive vice president.

Hoffman was an early investor in Facebook, Flickr, Care.com, and many more. In 2017 he joined the board of Microsoft.

Hoffman has coauthored several books on startups and professional development. He hosts the "Masters of Scale" podcast, on which he interviews founders about how they launched and scaled their companies, and is a partner at VC firm Greylock Partners. He was an early investor in OpenAI and used to serve on its board, and cofounded Inflection AI.

Hoffman has also recently criticized business leaders, including his fellow PayPal mafia members, for supporting Trump.

Like Hoffman, Sacks also served as COO at PayPal. Previously a management consultant for McKinsey & Company, David Sacks joined PayPal in 1999.

After PayPal was bought by eBay, Sacks produced and financed the box office hit "Thank You For Smoking," which would go on to be nominated for two Golden Globes. In 2006 he founded Geni.com, an online tool for building family trees.

In 2016, Sacks was briefly interim CEO at Zenefits, an HR software firm that was plagued by scandal, including allowing unlicensed brokers to sell insurance to its customers. In 2017, Sacks cofounded the early-stage investment firm Craft Ventures. 

Sacks is a serial entrepreneur and investor, with angel investments in Airbnb, Postmates, Slack, and many more. 

He's also a member of Elon Musk's inner circle and, like the Tesla CEO, is an avid Trump supporter, hosting a fundraiser for the president-elect at his home. Sacks reportedly urged Trump personally to choose Vance as his running mate, whom he was introduced to by fellow Paypal mafia member Thiel.

Trump said in December that he is appointing Sacks as his White House AI and crypto czar.

Karim and Chen were engineers, while Hurley was a web designer.

In 2005, the trio launched the video-sharing platform YouTube. Karim uploaded the platform's very first video, "Me at the zoo," an 18-second clip of Karim in front of the San Diego Zoo's elephant exhibit. It's been viewed over 292 million times.

Karim launched venture fund YVentures in 2008, through which he invested in Palantir, Reddit, Eventbrite, and Airbnb.

Hurley stepped down as CEO of YouTube in 2010. Since then, he's backed education startup Uptime and invested in several sports teams.

Chen invested in actor Joseph Gordon-Levitt's musical collaboration platform HitRecord, which in February secured $6.4 million in Series A funding.

McCormack joined PayPal in 2001, working as an assistant to Peter Thiel as the company prepared for its IPO.

In 2003, McCormack started a restaurant group in San Francisco. In 2008, he joined Thiel Capital and worked there for 5 years.

McCormack partnered up with Thiel again in 2010 to found Valar Ventures, a venture capital fund.

Valar Ventures has invested in technology startups well beyond Silicon Valley, including some in Europe and Canada. In August, Crunchbase reported the firm had closed on a $150 million funding round for a new venture capital fund, Valar Fund V.

McCormack continues to serve as a managing partner of the firm.

Entrepreneur Keith Rabois served as PayPal's executive vice president from 2000 to 2002.

He would go on to join his PayPal colleague Reid Hoffman at LinkedIn as its vice president for business and corporate development from 2005 to 2007. He was an early investor in startups like Square, where he spent two-and-a-half years as COO. 

Rabois is the CEO of OpenStore and has served on the board of directors for Yelp, Xoom, and Reddit.

He was a general partner at Founder's Fund, where he cofounded OpenStore, before returning to Khosla Ventures in early 2024.

Simmons was an engineer and Stoppelman was the vice president of technology after joining PayPal from X.com.

In 2004, the pair came up with the idea for a platform where users could leave recommendations about businesses in their area. They pitched the idea to Levchin, who provided an early investment of $1 million, and Yelp was born.

Simmons served as CTO at Yelp from 2004 until he left the role in 2010. Stoppelman is still CEO of Yelp, and has publicly spoken out in support of political issues like women's reproductive rights.

After leaving PayPal, Selby partnered with Thiel to start Clarium Capital Management.

Selby later helped manage Thiel Capital, the Thiel's family office, and started his own venture capital fund, AZ-VC, where he serves as managing partner. He still serves as managing director at Thiel Capital.

Starting in 2013, Selby began anonymously leaving tips for unsuspecting waitstaff, ranging into the thousands, and signing them "Tips for Jesus." His identity was confirmed by a New York City bartender who served him prior to receiving a $5,000 tip.

McClure served PayPal's director of marketing as for four years beginning in 2001.

According to McClure's LinkedIn, he began a program called the PayPal Developer Network, which consisted of about 300,000 developers that were using PayPal. 

He had a brief stint at Founders Fund before launching 500 Startups, an early stage venture fund. McClure stayed at 500 Startups until June 2017, when he was accused of "inappropriate behavior with women" in a New York Times report and stepped down from his role at the firm, writing an apology post titled "I'm a creep. I'm sorry."

He's since become an investor and owner in a professional sports league for ultimate frisbee and cofounded Practical Venture Capital, according to his LinkedIn.

• Yishan Wong was an engineering manager who later served as CEO of Reddit from 2011 to 2014. He then founded the reforestation company Terraformation in 2020, where he now serves as CEO.
• Jason Portnoy worked in finance at PayPal, and went on to work at Clarium Capital and Palantir. He's now a partner at VC firm Oakhouse Partners. 
• Premal Shah was a product manager at PayPal beginning in 2000, then went on to work at technology nonprofit Kiva. He's now president at financial-services startup Branch. 
• David Gausebeck was a technical architect at PayPal. Now, he serves as chief scientist at 3D modeling company Matterport. He cofounded 3D modeling company Matterport, where he now serves as chief scientist.
• Joe Lonsdale started his career as a finance intern at PayPal before moving into venture capital — he's worked at VC firms Clarium Capital, Formation 8, and 8VC. Lonsdale also cofounded Palantir, and has reportedly contributed to a Trump PAC.
• Eric Jackson was director of marketing at PayPal and went on to write a book about the company called "The PayPal Wars." He's currently the CEO of CapLinked. 

Thiel played a critical role in orchestrating Vance's rise to the top of Republican politics. The two first met in 2011, when Vance attended a talk Thiel gave at Yale Law School. In a magazine article written nearly a decade later, Vance called Thiel "a good friend" and said his speech was "the most significant moment of my time at Yale Law School."

After graduating from Yale, Vance became a principal at Thiel's VC firm, Mithril Capital. Their mentor-mentee relationship only grew stronger, with Thiel eventually investing heavily in Vance's own venture fund, Narya Capital, and writing a blurb for "Hillbilly Elegy." When Vance decided to pursue politics, Thiel remained by his side, pouring at least $15 million into his 2022 Senate campaign, according to OpenSecrets.

In 2021, Thiel introduced Trump and Vance at Mar-a-Lago, and remained invested in their relationship through the 2024 election. With repeated calls to President-Elect Donald Trump and persistent lobbying, Thiel played an important role in getting Vance on the ticket.

Musk and Thiel merged their online banking companies in 2000, forming PayPal. Their relationship soured, though, when Thiel ousted Musk as CEO and eventually took over the role. Come 2008, relations had evidently thawed enough for Thiel to make a $20 million investment in SpaceX, one of Musk's companies. The investment was crucial to helping SpaceX recover from a failed rocket launch that same year.

After Trump won the 2024 election, Thiel credited Musk for making other Silicon Valley leaders feel comfortable supporting the president-elect. Musk is one of Trump's top advisors and soon-to-be co-head of the Department of Government Efficiency.

In 2016, Thiel donated more than $1 million to Trump's presidential campaign. He had a prime-time speaking slot at the Republican National Convention and served as a go-between with Silicon Valley. Thiel said he was disappointed by Trump's first term and didn't donate in 2020 or 2024. Still, he predicted that Trump would win this year.

With Vance anointed as MAGA heir apparent, Thiel and Trump have a chance to rekindle their ties.

Mark Zuckerberg may not be a politician, but his influence in Washington runs deep. Between Facebook's role in free speech culture wars, the Federal Trade Commission's ongoing antitrust case against Meta, and Zuckerberg's rocky relationship with Trump, the tech leader is entrenched in the political conversation.

Thiel has a stake in Zuckerberg's involvement. He counts the Facebook founder among his mentees and was the site's first outside investor. Thiel sat on the board of Facebook and wielded great influence as its longest-serving member, but sparred with some of the company's more liberal employees, per the Washington Post. He ended up stepping down in 2022.

In 2019, Thiel, Zuckerberg, and Trump all had dinner at the White House, illustrating the strengthening ties between the tech world and Washington.

Sam Altman, billionaire co-founder of OpenAI, the company behind ChatGPT, is another one of Thiel's mentees. Thiel offered advice and support throughout Altman's early career, eventually becoming an early investor in OpenAI.

Like other prominent tech companies, OpenAI is under federal scrutiny. The Securities and Exchange Commission is investigating if the company's investors were misguided after board members suddenly ousted Altman as CEO in 2023, the Journal reported.

Beyond the investigation, Altman is becoming more involved in Washington. In the summer of 2023, he began a lobbying campaign in Congress about the future of AI regulation. OpenAI has spent money trying to sway Washington and hired staff with political know-how, per CNBC. As AI policy is poised to become an even bigger political question, Altman's influence — and Thiel's, by proxy — may continue to grow.

Biotech billionaire and former GOP presidential candidate Vivek Ramaswamy is set to co-lead DOGE.

Like Vance, Ramaswamy first met Thiel as a student at Yale Law School — he told PBS that it may have been at the very same speech that so impacted the vice president-elect. At the time, Ramaswamy attended an "intimate lunch seminar" Thiel hosted for a small group of students, per the New Yorker.

Eventually, Thiel threw his wealth behind Ramaswamy. In early 2022, Ramaswamy co-founded Strive Asset Management, an "anti-woke" investment fund, and Thiel was an early investor.

David Sacks, a former PayPal executive and prominent venture capitalist, will serve as the White House's AI and crypto czar during Trump's second term. Thiel and Sacks met at Stanford, where they co-wrote the controversial book, "The Diversity Myth." Both men have apologized for some of the book's content, which downplayed date rape. Sacks also served as editor-in-chief for the Stanford Review, a libertarian newspaper Thiel founded.

In 1999, Sacks joined Thiel's company Confinity, which later became PayPal. He eventually served as PayPal's chief operating officer and continued working closely with Thiel.

As the AI and crypto czar, Sacks will create the country's legal framework for crypto and head a presidential council of advisors on science and technology. The council will, according to the White House's website, be comprised of industry actors, academics, and people from non-profit organizations. Through Sacks, cryptocurrency supporters will likely have a direct line to Trump, Bloomberg reported.

Trump has nominated Jim O'Neill, former CEO of the Thiel Foundation, as the deputy secretary of the Department of Health and Human Services.

A Silicon Valley investor, O'Neill worked at HHS under former President George W. Bush before moving to Thiel's network. During his time as the acting CEO of the Thiel Foundation, O'Neill co-founded the Thiel Fellowship, which gives a $10,000 grant to young people who skip out on or pause college to tackle big projects. In 2012, O'Neill worked with Thiel to launch Mithril Capital Management, the same VC fund where Vance worked. He served as the fund's managing director but left in 2019 — he sued Mithril later that year over claims of unfair business practices and a contract breach.

During Trump's first term, Thiel pushed to have O'Neill fill a prominent health role, per the Post. If confirmed this time around, O'Neill will work closely with Robert F. Kennedy Jr., whom Trump tapped to lead HHS. O'Neill, who has criticized the FDA in the past, would play a big role in HHS' daily operations and policy decisions.

Thiel's Washington connections extend to his businesses, especially the data mining company Palantir that he co-founded in 2003. Palantir makes software to manage, analyze, and secure data, and its biggest client is the US federal government.

Federal government contracts helped build Palantir, which started out by partnering with defense and intelligence agencies. The company focuses on counterterrorism efforts and immigration enforcement. Some investors anticipate defense and immigration enforcement will see increased spending under a second Trump administration, meaning Palantir may get a boost.

An ideological ally of Thiel and Vance, Blake Masters lost his bid for a Senate seat in Arizona to Sen. Mark Kelly, but nonetheless benefited from Thiel's money and support. A decade before running for the Senate in 2022, Masters took Thiel's lecture when he was a student at Stanford Law School. Enthralled by Thiel and the course, Masters posted his notes from the influential class on a website.

The two co-authored a book, and Masters served as chief investment officer at Thiel's investment firm and president of the Thiel Foundation. When Masters pivoted to politics, Thiel donated $13.5 million to Masters' 2022 campaign.

Though Thiel's most notable political contributions have gone to Vance, Masters, and Trump, he's donated to an array of other politicians and Republican causes. Among his beneficiaries are Sen. Josh Hawley of Missouri and Sen. Ted Cruz of Texas, according to OpenSecrets. He's also given to the Republican National Committee and other GOP-aligned groups.

Thiel isn't entirely partisan with his contributions, though. In 2014 and 2015, he gave at least $70,000 to Gavin Newsom, the Democratic governor of California. Between 2011 and 2016, he also donated at least $7,800 to Rep. Ro Khanna, a Democrat who represents parts of Silicon Valley, per OpenSecrets.