Thanks to his relationships to tech billionaires like Peter Thiel and Elon Musk, Epstein had access to a number of lucrative tech investments. But he walked away from several deals with major startups that could have netted him hundreds of millions, the new cache of DOJ emails show.
In 2010, Jeffrey Epstein received an email from a contact looking for advice on investing in a prominent venture capital firm. He had no in. “Silicon Valley is another world,” he wrote, according to an email published by the Department of Justice. But within a few years, the disgraced financier would be trading emails with some of tech's most powerful figures, from Elon Musk and Sergey Brin to Bill Gates and Reid Hoffman—and boasting in a 2016 email of “lots of friends in Silicon Valley.”
Now, newly released emails from the Department of Justice reveal further details on how Epstein translated an incredible level of access to some of the wealthiest and most powerful tech titans of our time into personal investments, including checks to both venture funds and major startups like Coinbase. But they also highlight how despite his network, he ultimately made surprisingly few deals, and in some cases may have left hundreds of millions of dollars on the table.
“He wasn’t very good at tech investing,” says a source familiar with Epstein’s thinking. Despite his networking with tech CEOs and venture capitalists, “I’m not sure that was his world, and that’s why I don’t think he did very well in it.”
That these tech billionaires appear in the latest dump of documents does not mean they did anything illegal in maintaining contact with Epstein. Many of those named have denied or downplayed ties to Epstein. However, it does raise uncomfortable questions about why so many sought his counsel, funds and advice long after his 2008 sex crime conviction.
Have a tip about Epstein’s (or others’) tech investments? Contact Iain Martin at iain.martin@forbes.com or Phoebe Liu at pliu@forbes.com or phoebe.789 on Signal.
One of Epstein's earliest and most prolific correspondents in tech was PayPal founder and Founders Fund investor Peter Thiel. Epstein swapped scores of emails with the conservative investor dating back to 2014, and the pair appear to have met for meals at least eight times through 2017, according to emails in the DOJ archive. Epstein floated invitations for dinner with academic Noam Chomsky, director Woody Allen and former Norwegian diplomat Terje Rød-Larsen over email, and offered intros to the likes of former Israeli prime minister Ehud Barak and former Russian deputy economy minister Sergey Belyakov, the emails show. On multiple occasions, Epstein invited Thiel to his island. “Im always free to do as i please,” Epstein wrote in 2014. “would you prefer to visit the island or i can meet in ny.” Thiel’s spokesperson Jeremiah Hall said Thiel never traveled to the island and did not comment further on the billionaire venture capitalist’s dealings with Epstein.
The relationship seems to have paid off for Epstein. In 2015 and 2016, he committed to invest $40 million into Valar Ventures, a fund co-founded by Thiel that backs startups outside Silicon Valley like British money transfer platform Wise (TransferWise), French bank Qonto, and New Zealand accounting tool Xero. The investment had ballooned to $170 million as of last year, according to the New York Times, raking in millions for Epstein’s estate if sold.
The king of contrarian investors told him to pass on the streaming service, and also advised against investing in Palantir, the defense-tech firm he co-founded, saying the price was "below market."
Beyond Thiel’s Valar, Epstein’s biggest tech win seems to have been backing Coinbase. He invested $3 million at a $400 million valuation in 2014, according to the DOJ emails. The files also reveal that Epstein sold half of his stake to crypto fund Blockchain Capital in 2018 for $15 million. The crypto exchange went public in 2021 and now has a market cap of $49 billion. It is unknown if Epstein’s estate held the other half of his original stake in Coinbase until its initial public offering; if he did it would have been worth around $30 million at the IPO, two years after he died.
This lucrative deal was brokered by former child actor and crypto investor Brock Pierce, who at the time was working with Blockchain Capital. Epstein met Pierce at a 2011 conference and swapped emails about women, investments and introductions to associates like populist pundit Steve Bannon over the next seven years, according to the files and first reported by crypto news website Protos. In one December 2018 email released in the latest tranche of Epstein files, Pierce invited him to the Caribbean island of Antigua for “a boat…full of amazing Ukraine’s finest.” Pierce didn’t respond to a request for comment.
The files indicate that Epstein also backed Jawbone, the failed fitness tracker and headset company, which went under in 2017. Investment documents released by the DOJ, which call him a “major investor,” indicate he lost his full investment of $10 million. In a tense August 2018 email exchange with cofounder and CEO Hosain Rahman, Epstein demanded a settlement. “It is simple,” he wrote. “The obligation is yours. If you had a current net worth of over 100 million I would without a doubt use my resources to recover the monies that you received from me.”
Rahman replied, “I absolutely acknowledge that I made mistakes while running the last business. I have learned a ton of painful lessons from those mistakes. Those mistakes were never intentional and I don't agree that I misled you about your prior investment.” Rahman didn’t respond to a request for comment.
The disgraced financier’s files also show that he invested in multiple other venture funds. That includes Neoteny, a small venture fund run by a long-time Epstein associate Joi Ito, who led MIT Media Lab until 2019 when the New Yorker revealed Epstein had donated millions of dollars to the Massachusetts research lab. Ito and Neoteny did not respond to emailed requests for comment, but Ito publicly apologized for his connections to Epstein in 2019.
Some in Epstein’s orbit seemed to realize the potential reputational harm of doing business with a convicted sex trafficker of minors. “Some people don't like certain associations, deservedly or not. Is your name good with the CFTC [Commodity Futures Trading Commission],” crypto investor Jeremy Rubin wrote to Epstein in 2016 about an investment in bitcoin options exchange LedgerX.
In July 2018, Rubin and Epstein discussed tactics to get him on a due diligence call for bitcoin miner Layer1 without his identity being revealed. “I'm concerned otherwise potential investments googling your name might get spooked,” Rubin wrote in another email.
It is unclear from the files if Epstein invested in either Layer1 or LedgerX. LedgerX was acquired by FTX in 2021. Rubin didn’t respond to a request for comment but wrote on X on Monday that he hopes the emails “bring us closer to justice for those harmed and a better understanding of the nature of corruption in our society.” Layer1 said that the company had not taken money from Epstein.
Epstein had relationships with a number of other venture capitalists and tech investors as well, the files reveal, including Russia-born billionaire investor Yuri Milner, former tech exec and Andreessen Horowitz board partner Steven Sinofsky, and Day One Ventures founder Masha Bucher, who regularly introduced him to startup founders. (Bucher did not respond to a previous comment request on her Epstein ties.)
Milner met with Epstein twice, once apparently at Epstein’s New York City apartment and once at his Paris apartment, both in 2011. According to Milner’s representative, the meetings were arranged by Ian Osborne, an investor and consultant who had a close relationship with Epstein, and the billionaire had no further contact with him. “I wholeheartedly regret that I ever met, or had any association whatsoever with, Epstein,” Osborne said. “I never witnessed, nor was aware of, the repellent and illegal behaviour by him.” Sinofsky wrote to Forbes that he is not employed by any venture firm and “work for myself.”
Beyond billionaire investors and founders, the files make clear Epstein also craved access to early-stage startups, college professors and AI researchers. In 2012, he emailed Musk to “remind me of the AI guy in London,” referring to Deepmind cofounder Demis Hassabis. His contacts suggested names of professors to meet, and some of them filed field reports from campuses and conferences, like German AI researcher Joscha Bach. “My personal funds are currently depleted again, could you please help me out again? (Still embarrassed to ask.),” Bach wrote in an email to Epstein in 2015. Epstein covered Bach’s living costs from 2013 to 2019 when he was a researcher in need of funding, according to Bach. “I had strong differences with his value system, and ending this dependence was always a priority,” he wrote to Forbes. “I have never been aware of any crimes of Epstein after his conviction.”
Beyond Coinbase and Valar Ventures, it does not appear Epstein translated his tech connections into other successful investments. Instead, he walked away from multiple deals.
In one 2014 email exchange with Thiel, Epstein asked if he should take a stake in Spotify, then valued at $5 billion. “Im being offered 100 million of spotify at 5 b valuation?” he wrote. “thoughts?” The king of contrarian investors told him to pass on the streaming service, and also advised against investing in Palantir, the defense-tech firm he cofounded, saying the price was “below market.” Remarkably bad advice. Spotify went public at a $27 billion valuation in 2017; Palantir peaked on the Nasdaq at a $494 billion market cap.
By 2017 Epstein seems to have realized his mistake with Spotify, instructing his accountant to invest $1 million in 2017 via a special purpose vehicle from hedge fund and startup Honeycomb, shortly before its 2018 IPO, according to Epstein’s files. According to the latest emails, Epstein had invested at least $70 million with Honeycomb, run by former Point72 investor David Fiszel. Gibson Dunn lawyer Reed Brodsky, who represents Fiszel, says that Honeycomb largely offloaded Epstein’s investment following his 2019 conviction.
Despite Epstein’s connections to tech moguls, he was instead often pitched on buying secondary shares in what are now some of the world’s most valuable companies. He appeared to have ignored some potentially lucrative opportunities, including two chances to invest in SpaceX. In 2017, an associate asked if he was interested in secondary shares in SpaceX when it was worth $22 billion, according to a DOJ-released email. Even though Epstein had known Musk for over a decade, there’s no record in his emails of any direct offers to invest in SpaceX, now valued at $1.25 trillion.
Likewise, he did not appear to act on an opportunity pitched over email by British fixer turned-financier Osborne to invest in German ecommerce giant Zalando in 2011. It listed in 2014 on a $6.8 billion valuation.
The emails also show that Osborne, who at one point visited Epstein’s island, per the emails, courted Epstein’s investment or input into a number of funds. At one point, a proposal was circulated for a $60 million offshore fund run by Osborne and Jacob Burda, a scion of Germany’s billionaire media dynasty, that would invest in social media companies; that never got off the ground. Julia Korn, a spokesperson for Burda, wrote to Forbes that he had never been involved with pitching investments into Hedosophia to Epstein, and that there was no relationship between Epstein and Burda.
Osborne also sent Epstein early pitches for his secretive tech investment fund Hedosophia. “As for the name…It just merges the Greek works for ‘pleasure’ and ‘wisdom,’” said Osborne in a 2012 email to Epstein. “At no point did Epstein make any investment in Hedosophia,” wrote a spokesperson for Osborne. “There was never any financial relationship between Epstein and Mr Osborne.”
Hedosophia would go on to invest in startups like Spotify, SpaceX and Bolt Financial (but also the defunct Jawbone). It became best known for teaming up with Chamath Palihapitiya’s Social Capital to set up special purpose acquisitions companies (SPACs), which they used to take public Richard Branson’s space travel startup Virgin Galactic, real estate tech firm OpenDoor and CloverHealth. These firms are now worth a fraction of their listing prices. Even though Epstein never put his own funds into Hedosophia, he appears to have coached Osborne on the SPAC strategy. “I’m really happy with the model that you revised … the corporate (Spac type) structure is so much better than a fund, and the concept you just drew out on the whiteboard is the perfect iteration of that,” Osborne wrote in a 2012 email to Epstein.
Epstein kept hunting for new technology, even in the months leading up to his arrest in July 2019. That January, he wrote to Thiel, “What are you seeing that's exciting. =AO rejuvenation? plant biology?