Peter Thiel, the billionaire co-founder of PayPal and Palantir, is once again making headlines, this time for shedding a significant stake in the fintech firm Wise, just as his past investment decisions come under renewed scrutiny. Thiel, who was the first outside investor in Facebook back in 2004, had purchased a 10% stake in the then-fledgling social network for just $500,000.
However, according to a recent report by Fortune, Thiel sold nearly 20 million Facebook shares shortly after the company’s 2012 IPO, when the price hovered around $20 per share. That decision, though planned as part of a 10b5-1 trading strategy to avoid insider trading concerns, cost him dearly in retrospect. Today, those shares would be worth over 37 times their original price, meaning Thiel may have missed out on more than $1 billion in potential gains.
While the move aligned with Thiel’s methodical investment exit strategy, it has reignited debate over whether even seasoned tech investors can predict the true long-term trajectory of platforms that transform global markets.
Valar Ventures Divests $70M in Wise Shares Amid Market Repositioning
In a more recent development, Thiel-backed Valar Ventures has sold £50 million (roughly $70 million) worth of shares in Wise Plc, the London-based fintech company formerly known as TransferWise. The block sale was conducted through an overnight book-build, as reported by Bloomberg, and involved around 4.8 million Class A shares priced at £10.30 each.
Valar Ventures had led Wise’s $6 million Series A round back in 2013, making the firm one of its early supporters. Wise went public in 2021 and has since become one of the UK’s most prominent fintech players. But rising regulatory scrutiny, slowing revenue growth, and increased competition from digital banking and blockchain platforms have put downward pressure on Wise’s valuation.
Peter Thiel firm appears to be adjusting its investment focus accordingly. Analysts believe the stake sale marks a strategic shift away from maturing fintech firms toward more disruptive, high-growth sectors such as crypto, Artificial Intelligence, and Web3 technologies.
A Pattern of Contrarian Timing and Capital Reallocation
These two major moves, exiting early from Facebook and offloading a sizable position in Wise, underscore a defining trait of Thiel’s investment philosophy: exit early, reinvest aggressively, and focus on the next big disruption. While critics argue that Thiel left billions on the table with Facebook, supporters say his disciplined capital reallocation has allowed him to identify and back the future winners of the tech world.
Founders Fund, another Peter Thiel-backed entity, has recently doubled down on cryptocurrency infrastructure and blockchain-based ventures, including Polymarket and Layer1. His moves reflect a forward-looking posture, even if they sometimes come at the cost of near-term upside.
Thiel’s recent actions signal a larger narrative unfolding in the tech investment world: a transition from traditional fintech toward decentralized finance and next-gen platforms. As macroeconomic conditions shift and sector valuations tighten, Thiel is once again placing his bets, only this time, on the digital frontiers of tomorrow.
Sources:
https://www.ft.com/content/8c903f2e-42a6-496b-b098-ca733f340ffc
