In 2014, Coinbase was still a young company, barely two years old, trying to establish itself as a platform where people could buy and sell Bitcoin. Like many early-stage start-ups, it needed outside funding to expand. Instead of turning only to traditional venture capital, it accepted money from a controversial figure: financier Jeffrey Epstein.

That December, Fred Ehrsam, one of Coinbase’s co-founders, wrote to colleagues that it might be worthwhile to meet Epstein if the opportunity arose. At the time, Epstein was preparing to invest $3 million in the company. Although he had already pleaded guilty in 2008 to charges involving solicitation of a minor, Coinbase proceeded with the deal.

As Coinbase grew into one of the world’s largest cryptocurrency exchanges, Epstein’s stake appreciated significantly. Newly released Justice Department records suggest that his investment eventually generated multimillion-dollar returns before his arrest in 2019 on federal sex-trafficking charges.

The documents also shed light on how deeply connected Epstein was within Silicon Valley. Despite increasing public awareness of his crimes, he continued to cultivate relationships with venture capitalists, tech founders, and public relations professionals who helped him gain access to high-profile investment opportunities.

Among those he interacted with was billionaire investor Peter Thiel, who reportedly discussed potential investments in Palantir, a data analytics company he co-founded. Epstein also invested in Jawbone, a popular wearable technology start-up at the time, and was introduced to opportunities related to SpaceX through financial intermediaries. In addition, he worked with a Russian-born public relations specialist who arranged meetings with entrepreneurs and journalists.

Epstein had longstanding ties to prominent figures in the tech world, including Bill Gates, Sergey Brin, Reid Hoffman, and Peter Thiel. Some of them later distanced themselves from him after his crimes came to light. The latest trove of documents offers a clearer picture of how he rebuilt his wealth after his 2008 conviction, ultimately controlling assets valued at more than $600 million before his 2019 arrest.

His connection to Coinbase came through Brock Pierce, a cryptocurrency entrepreneur with a controversial background. Pierce kept Epstein informed about the company’s progress through updates often signed by Ehrsam or Coinbase CEO Brian Armstrong. In 2018, a firm associated with Pierce attempted to purchase half of Epstein’s Coinbase holdings for $15 million, though it remains unclear whether Epstein ever sold the remainder.

Coinbase declined to comment on the matter, and Ehrsam did not respond to requests for clarification.

Epstein’s involvement in technology dated back to the dot-com era, long before his criminal activities became public. He frequently attended tech conferences and elite gatherings such as Edge Foundation dinners, where influential thinkers and entrepreneurs mingled.

Investor Jason Calacanis maintained contact with Epstein even after his conviction. Emails later revealed that Calacanis helped connect him with two Bitcoin developers in 2011. After the documents were released, Calacanis said publicly that he barely knew Epstein personally but that Epstein seemed to appear everywhere in tech circles, likely because Calacanis was an active angel investor.

Hosain Rahman, co-founder of Jawbone, first encountered Epstein at a TED conference. In 2012, adviser Ian Osborne reintroduced the two and encouraged Epstein to invest in Jawbone. During the filming of Woody Allen’s movie “Blue Jasmine” in San Francisco, Epstein even invited Rahman to visit the set and showed him a pair of advanced smart glasses.

Rahman later emailed Epstein saying he had big ideas he wanted to discuss. That same year, he visited Epstein’s expansive Zorro Ranch in New Mexico.

Epstein invested $5 million in Jawbone in 2012 and expanded his stake to $11.25 million by 2017. However, Jawbone ultimately failed and liquidated in 2017. Epstein responded aggressively, threatening legal action against Rahman and reportedly hiring a private investigator to look into his background. To ease tensions, Rahman later offered Epstein a senior advisory role in a new venture called Jawbone Health.

Rahman later expressed regret about taking Epstein’s money, saying the company wished it had never accepted his investment. Osborne declined to comment.

Through Osborne, Epstein also explored potential investments in cybersecurity firms and Palantir. By 2014, he was actively seeking advice from Peter Thiel, even asking whether he should invest $100 million in Spotify at a $5 billion valuation. Thiel advised him to wait and expressed more optimism about Palantir.

Palantir later stated that it had no record of Epstein ever being an investor or shareholder. Spotify said it never offered him a direct investment opportunity. Thiel’s office did not respond to media inquiries.

Epstein did invest $40 million in Valar Ventures, a firm linked to Thiel, through two separate transactions. Those holdings, now controlled by his estate, were valued at approximately $170 million last year. Valar said it hoped any future proceeds could be used to support victims of Epstein’s crimes.

Epstein also leveraged his relationship with Deutsche Bank, which became his client in 2013. The bank later paid a substantial fine for its role in facilitating his financial activities. Through a Deutsche Bank contact, Epstein’s adviser Paul Barrett was introduced to Vy Capital, an Emirati venture firm that offered exposure to SpaceX shares.

In 2017, Barrett met with Vy Capital regarding a vehicle that held access to $50 million in SpaceX stock at a time when the company was valued at $22 billion. Epstein had previously visited SpaceX in 2013 at Elon Musk’s invitation and reportedly toured the headquarters. Whether he ever invested directly remains unclear.

Vy Capital later said it only had a brief introductory call with Barrett arranged by Deutsche Bank and never conducted business with Epstein. The firm described his behavior as reprehensible. Deutsche Bank and Barrett declined to comment.

In 2017, Epstein connected with Masha Drokova, now known as Masha Bucher, a public relations professional who later founded Day One Ventures. She arranged meetings between Epstein and reporters from major publications and introduced him to several entrepreneurs, including longevity advocate Bryan Johnson. Johnson later said he found Epstein deeply disturbing after a single video call.

Epstein also maintained ties with smaller tech figures, including Bitcoin developer Jeremy Rubin and cybersecurity entrepreneur Vincenzo Iozzo. In 2018, he attempted to create a new investment vehicle called Deploy Capital for Rubin, planning to seed it with $5 million.

Rubin expressed concerns that start-up founders might be reluctant to accept funding from a convicted sex offender. He suggested keeping Epstein’s name out of the fund and simply saying the capital came from an unnamed source. Epstein agreed in principle but still wanted to meet the founders of Rubin’s first potential investment, a cryptocurrency firm called Layer1.

When Layer1’s founders demanded to know who was behind the money, Epstein suggested that Peter Thiel could vouch for him. Layer1 later confirmed it never accepted funding from Epstein or Deploy Capital.

Despite the controversy, Rubin later told Epstein that the founders were willing to speak with Thiel, marking another instance of how Epstein sought legitimacy through his powerful connections in the tech world.