Written by: David, Shen Chao TechFlow
'What important truth do very few people agree with you on?' (What important truth do very few people agree with you on?)
This is Peter Thiel's favorite question to ask in interviews, and it's the opening line of his bestseller (Zero to One).
If you ask him this question, the answer might be:
In 2003, when everyone was focused on social networking, he chose to do data analysis for the CIA;
In 2014, when Bitcoin dropped to $400, he bought $20 million worth;
In 2022, when everyone was shouting 'Bitcoin will hit $100,000', he cleared all his holdings.
Today, 57-year-old Peter Thiel has a fortune of $26.6 billion.
The company he founded, Palantir, has a market value of $400 billion; he has made $2.5 billion in profit from cryptocurrency investments, and behind the recently popular coin stocks BMNR and the publicly listed crypto exchange Bullish, there are his investments;
And the J.D. Vance he nurtured has become the Vice President of the United States.
But in the broader view of Silicon Valley, he remains an outlier:
A billionaire openly supporting Trump, a tech entrepreneur serving intelligence agencies, an investor who sells when everyone else buys.
This is a story about how contrarian thinking creates wealth and how patience transforms into power.
The PayPal palace coup
In December 1998, 31-year-old Peter Thiel and 23-year-old Max Levchin founded Confinity in Palo Alto. Almost simultaneously, Elon Musk founded X.com.
The two companies were engaged in a cash-burning battle, both aiming to become the dominant force in internet payments. Three months later, the two companies merged to form PayPal, with Musk as CEO.
But the honeymoon period lasted only six months. In September 2000, while Musk was on vacation in Australia, the company's board voted to remove Musk from the CEO position, with Thiel taking over.
The surface reason for the removal was technical differences; Musk wanted to migrate the system from Unix to Windows. But the deeper reason was the fundamental disagreement between the two on the company's direction: Musk wanted to build a comprehensive financial services platform, while Thiel only wanted to focus on payments.
This is one of the most famous palace coups in Silicon Valley history, and Thiel's handling of this coup was quite exquisite. He chose to launch the attack while Musk was absent, having previously rallied support from PayPal's then-technical lead Max Levchin, packaging the power struggle as a technical reason.
After the change of helm, PayPal focused on its payment business, quickly achieving profitability, and was sold to eBay for $1.5 billion in 2002.
As the largest individual shareholder, Thiel cashed out $55 million from this. This money became his first pot of gold in the investment world.
Former colleagues before investment
More than twenty years later, when people discuss the power structure of Silicon Valley, they cannot avoid one fact: many of the most influential people once worked in the same office of the same company.
And the owner of that office is Peter Thiel.
After eBay's acquisition was completed in October 2002, holding $55 million from cashing out of PayPal, Thiel founded the investment fund Founders Fund.
His first batch of investment targets were almost all former colleagues from PayPal, a group later referred to as the 'PayPal mafia':
When Reid Hoffman just founded LinkedIn, Thiel was the first outside investor, putting in $500,000; when Chad Hurley and Steve Chen were tinkering with the video site YouTube, Thiel participated in the early financing; when Jeremy Stoppelman wanted to create the local review site Yelp, Thiel provided the first seed funding...
The most interesting aspect is his relationship with Musk. After the 'coup' in 2000, the two seemingly went their separate ways.
But in 2008, when SpaceX was on the brink of bankruptcy and its fourth launch failure could mean the end of the company, Founders Fund led a $20 million investment. This money allowed SpaceX to survive until NASA's contract.
The businesses of former colleagues also brought great success to Founders Fund. YouTube was acquired by Google for $1.65 billion, LinkedIn reached a peak market value of over $26 billion, and SpaceX is now valued at over $200 billion.
But what Thiel really cares about seems not to be money; the 'PayPal mafia' gradually controlled half of Silicon Valley.
Reid Hoffman became Silicon Valley's 'super connector,' with almost every entrepreneur needing to find connections through him; David Sacks transitioned from entrepreneur to podcast host, and his All-In podcast influences the entire tech circle's public opinion, while he himself is the 'crypto czar' of the White House. Musk goes without saying; from Tesla to SpaceX to X, he has almost defined the technological ambitions of this era.
Even more amazing is that this network has a loyalty that transcends business.
In 2016, when Thiel was isolated by all of Silicon Valley for supporting Trump, members of the PayPal mafia remained silent. They may not agree with his choice, but no one kicked him while he was down.
By 2024, when Thiel urged J.D. Vance to run for office, David Sacks not only donated but also publicly endorsed him on a podcast.
Every investment Peter Thiel makes adds a node to his power network, and each successful exit strengthens that network.
Betting on Facebook, selling out at IPO
In the summer of 2004, 20-year-old Harvard dropout Zuckerberg also sought out Thiel.
At that time, Facebook's user base had just surpassed 1 million. The social network space was already crowded, with Friendster having 7 million users and MySpace having 5 million users.
Mainstream investors in Silicon Valley were not optimistic about Facebook, but Thiel asked Zuckerberg a question:
'What is the difference between Facebook and MySpace?'
'On Facebook, you have to use your real name,' Zuckerberg replied.
It is this seemingly simple difference that led Thiel to make a judgment. He later wrote in his (Zero to One): True identity means trust, trust means real social relationships, not virtual follower counts.
In September 2004, Thiel personally invested $500,000 in Facebook, acquiring a 10.2% stake. The terms of this investment were shockingly simple, with no requirement for a board seat, no liquidation preference, and not even anti-dilution clauses.
The subsequent story proved his judgment. In 2005, when Accel Partners invested at a $127 million valuation, other VCs only realized what they had missed later. By 2007, Microsoft invested at a $15 billion valuation, and Facebook had already become a phenomenon.
In May 2012, Facebook went public at an opening price of $38. Most early investors chose to hold, but Thiel sold 16.8 million shares on the IPO day, cashing out approximately $640 million. In the following months, he continued to reduce his holdings, ultimately turning an initial $500,000 investment in Facebook into over $1 billion in profit, achieving a return of over 2000 times.
Facebook's stock price indeed later rose to over $300, which seems like Thiel did not maximize the returns on this investment. But just two years after Thiel cashed out, in 2014, Bitcoin's price dropped to $400.
On one side are the star stocks that everyone is chasing; on the other are the emerging markets that everyone is panicking about. Thiel once again chose the latter.
Bottom-fishing and peak escaping, building a crypto empire
In 2014, Bitcoin was priced at $400, having just crawled out from the ruins of Mt. Gox.
The entire crypto market had a total market value of less than $5 billion. At that time, Peter Thiel's Founders Fund quietly bought $15-20 million worth of Bitcoin, at an average price of less than $500. This investment was so small that it didn't even appear in the fund's quarterly report.
From 2014 to 2022, Founders Fund did not sell a single Bitcoin, and even increased holdings twice in 2017 and 2020.
In March 2022, when Bitcoin was still at a high of $42,000, Founders Fund suddenly cleared all its holdings.
According to later reports from the Financial Times, this cash-out yielded $1.8 billion. Two months later, the Terra/Luna collapse triggered the worst bear market in crypto history. By the end of the year, Bitcoin had dropped to $15,500.
Interestingly, just four months after accurately cashing out at the peak, Thiel also gave a passionate speech at the Miami Bitcoin conference, calling Bitcoin 'the future of financial freedom.' He even created an 'enemies list' and referred to Buffett as 'the Socratic grandpa from Omaha' because he did not support Bitcoin.
The followers in the audience applauded wildly, but no one knew that this 'preacher' had just completed the largest-scale cash-out of crypto assets in history.
But Peter Thiel is not just a savvy cryptocurrency trader. While buying and selling Bitcoin, he is systematically investing in the entire crypto ecosystem:
-Trading infrastructure: In 2018, Founders Fund led an investment in Tagomi Systems, a company providing cryptocurrency trading services to institutional investors. Tagomi solved trading slippage issues by aggregating liquidity from multiple exchanges. In 2020, Coinbase acquired Tagomi for $150 million.
In 2021, Thiel personally invested in Bullish, an institutional-grade crypto exchange operated by Block.one. Bullish's uniqueness lies in its compliance efforts from the start, having obtained licenses from multiple jurisdictions. In July 2025, Bullish officially submitted its IPO application, with a valuation exceeding $9 billion.
-Lending and DeFi: Valar Ventures (Thiel's other fund) invested in BlockFi in 2019, which was once one of the largest crypto lending platforms; however, BlockFi ultimately went bankrupt in 2022.
In 2023, during the market's lowest ebb, Founders Fund invested in Ondo Finance, a previously neglected RWA track, which by 2025 had become the hottest direction in the crypto field.
-Project incubator: In October 2023, Founders Fund also invested in Alliance DAO, acquiring a minority stake and providing support for companies invested in by Alliance DAO. The latter is currently one of the largest incubators in the crypto industry, as well as an early supporter of star projects like Pump.fun.
-European layout: Through connections in Germany, Thiel invested in Bitpanda, Austria's largest cryptocurrency exchange. By 2021, it was valued at $4.1 billion, becoming Europe's most valuable crypto unicorn.
In the summer of 2023, Bitcoin hovered below $30,000 for several months. The bankruptcy trial of FTX was still ongoing, the SEC's crackdown on the crypto industry had intensified, and mainstream media was filled with rhetoric declaring 'crypto is dead.'
At the moment when everyone is fleeing, Founders Fund is back.
According to a Reuters report in February 2024, the fund gradually bought $200 million worth of Bitcoin and Ethereum in the late summer to early fall of 2023, each taking half.
Time has once again proven Thiel's judgment.
In January 2024, the SEC approved a Bitcoin spot ETF. Within months, over $50 billion in institutional funds flooded in. By August 2025, Bitcoin surpassed $117,000, and Ethereum exceeded $4,000. Founders Fund's $200 million investment had more than 100% paper profit.
And on July 16 of this year, Bitmine announced that Peter Thiel's Founders Fund had purchased a 9.1% stake.
Looking back at every node in Peter Thiel's entry into crypto, from peak escape to equity stakes and track layout, most of them hit the right rhythm. In public, he is a preacher for Bitcoin; in practice, he is an executor of contrarian thinking.
As of August 2025, according to various estimates, Thiel has made over $2.5 billion in profit from cryptocurrencies: $1.8 billion from the peak escape in 2022, $500 million from exits of early-stage investments, and $200 million from bottom-fishing in 2023.
This does not include his holdings in Bullish, Bitpanda equity, and the latest investment in BMNR.
Binding the fate of the United States
In addition to investing in the PayPal mafia, Thiel actually founded his own company—Palantir, a company serving the government and military, developing intelligence systems for them, after leaving PayPal in 2003.
What was the mainstream in Silicon Valley at that time? Social networks, e-commerce, search engines. Thiel chose to do data analysis for the CIA.
Palantir's first seed funding of $2 million came from the CIA's venture capital arm In-Q-Tel, while Thiel himself invested $30 million. The company is named after the 'Seeing Stone' from The Lord of the Rings, a magical stone that can perceive all information.
The next seven years saw almost no public reporting. It wasn't until the Afghanistan War in 2010 and the killing of Osama bin Laden in 2011 that the media learned that Palantir's intelligence analysis system played a key role in both.
The company Thiel created has a client list resembling a spy thriller cast: CIA, FBI, NSA, the Pentagon; but in Silicon Valley, which advocates freedom, this has made Palantir a target. Protesters demonstrated outside its office, calling it an 'evil company.' Recruitment became difficult, and commercialization repeatedly hit walls.
When it went public in 2020, Wall Street was not convinced. Years of no profits and over-reliance on government contracts led the stock price to drop from $10 to as low as $5.92.
In 2023, after the explosion of ChatGPT, Palantir launched the AIP platform, combining 20 years of intelligence analysis capabilities with popular large language models to serve more internal process management for enterprises. When Google withdrew from the Pentagon's AI project due to employee protests, Palantir stepped in.
Subsequently, military orders began to surge: In 2024, the U.S. Army signed a 10-year $10 billion contract with it; in April 2025, NATO officially procured the Maven Smart System it developed.
Meanwhile, the company's stock price skyrocketed from $6 at the beginning of 2023 to $187 by August 2025, bringing its total market value to $440 billion, surpassing the combined market value of the three major traditional defense contractors in the U.S.
(Reference: Five years, twenty times, the birth of America's most expensive national luck stock)
Palantir's true value is not in its stock price. The company's systems connect every node of power in the United States: the Department of Homeland Security uses it to track immigrants, the SEC uses it to investigate insider trading, and the IRS uses it to audit taxes.
When J.D. Vance, pushed by Thiel, became vice president, Palantir's government contracts significantly increased. Thiel influences policy-making through Vance, participates in power operations through Palantir, and controls Silicon Valley through the PayPal mafia. The synergistic effect of this power network is just beginning to manifest.
From a $30 million initial investment in 2003 to a current market value of $440 billion, for Thiel, Palantir brings not just wealth but also a passport to the core of Washington's power.
Choosing to work for the CIA twenty years ago seemed like the most incredible choice in Silicon Valley at the time. Looking back today, this may be Thiel's most astute layout.
Silicon Valley builds kings, it's never too late in ten years
By August 2025, sitting in the second highest seat of power in the U.S. is someone who just four years ago was calling Trump 'Hitler.'
J.D. Vance, 39, one of the youngest vice presidents in U.S. history.
From Yale Law School to Silicon Valley, from bestselling author to senator, and then to vice president, Peter Thiel has always been the driving force behind this incredible trajectory.
In 2011, Peter Thiel was invited to speak at Yale Law School, where he stated that elite institutions focus too much on peer competition, and students blindly pursue the climb up the prestige ladder. J.D. Vance, sitting in the audience, was deeply moved and got to know Thiel.
Years later, he wrote that this speech was 'the most important moment at Yale', and it changed Vance's life trajectory.
After graduating from Yale in 2013, he joined the top law firm Sidley Austin as expected. But just two years later, he resigned. The next stop was a biotech startup in Silicon Valley, Circuit Therapeutics, where he served as operations director.
For a lawyer with no tech background, this leap is too big. Circuit's CEO Frederic Moll later admitted to the media that part of the reason for hiring Vance was Peter Thiel's recommendation.
Thiel's venture fund had previously invested in Moll's last company, which is a typical example of Silicon Valley's interpersonal ties. In 2016, Vance's career underwent another turning point. He joined Peter Thiel's venture fund Mithril Capital as a partner.
That same July, his memoir (Hillbilly Elegy) was published and quickly topped the New York Times bestseller list. Suddenly, this previously unknown venture partner became a nationally recognized writer and cultural commentator.
According to reports from The Wall Street Journal in 2024, former colleagues at Mithril recalled that during Vance's year in office, he was rarely seen in the office; he spent most of his time across the country for book signings, speeches, and interviews.
But this seems to be exactly what Thiel wanted, not to nurture an investment manager but to cultivate a public intellectual.
In March 2017, Vance left the Mithril fund, but he did not leave Peter Thiel's orbit. He first joined AOL founder Steve Case's Revolution fund and then established his own fund, Narya Capital, in 2019.
Narya's list of investors says it all: the lead investor is Peter Thiel, with follow-on investors including a16z founder Marc Andreessen and former Google CEO Eric Schmidt.
In 2021, Vance announced his candidacy for Ohio Senator, during which, according to public records from the Federal Election Commission, Thiel donated $15 million to the super PAC Protect Ohio Values supporting Vance. This is the largest single donation to a Senate campaign in history.
Not just Peter Thiel. His friend David Sacks donated $1 million, and other Silicon Valley figures followed suit. Ultimately, donations from the tech sector accounted for most of Vance's campaign funding. An Ohio Senate seat became a target for Silicon Valley capital investments.
From being elected senator in November 2022 to being nominated as a vice-presidential candidate in July 2024, Vance took less than two years. This speed is extremely rare in U.S. political history.
Multiple media reports indicated that during Trump's vice-presidential selection process, the voices from Silicon Valley were unusually consistent. Not just Peter Thiel, but also Elon Musk, David Sacks, and others recommended Vance.
These tech tycoons see not just a vice president, but their spokesperson in Washington.
JD Vance's Silicon Valley network | Source: The Washington Post
Starting from the top left in a clockwise direction: Blake Masters, Joe Lonsdale, Peter Thiel, Jacob Helberg, David Sacks
After Vance took office, policies began to shift.
The federal government has increased its procurement of AI and data analysis tools, and Peter Thiel's Palantir has become a major beneficiary; at the same time, the U.S. government's regulatory attitude towards cryptocurrencies has clearly softened.
These changes may not be directly attributed to Thiel's influence, but the timing is thought-provoking.
Thiel's relationship with Vance perhaps represents a new model of political influence. Unlike traditional lobbying or political donations, it resembles a 'venture capital-style cultivation': early detection of talented individuals, providing funding and resource support, helping them gain power, and then achieving long-term influence through ideological resonance.
39-year-old Vance may have decades of political career ahead of him. This means Thiel's influence extends far beyond ordinary election cycles.
'What important truth do very few people agree with you on?'
Perhaps for Peter Thiel, the answer has always been simple: Power never belongs to those in the spotlight.
