How a colorful investor profited from a crypto giant’s dealmaking

Tether runs the cryptocurrency known as tether, which now has more than $115 billion worth of tokens in circulation. Thanks to higher interest rates, Tether is raking in roughly $4 billion a year from the Treasurys that back its cryptocurrency.

The company has enlisted tech investor and entrepreneur Christian Angermayer to help invest its windfall. The colorful financier has also sought riches in unconventional investments including psychedelics, dinosaur fossils and an Olympics alternative where athletes are encouraged to use performance-enhancing drugs.

So far, Angermayer has helped Tether invest roughly $1.5 billion into two companies where he already holds stakes. He also earned commissions on some of the transactions. The companies they invested in have frequently lost money.

Within the past year, Tether took majority stakes in Northern Data, a money-losing German data center operator that aspires to be an AI company, and Blackrock Neurotech, a struggling Utah-based brain implant company in competition with Elon Musk’s Neuralink.

Tether didn’t provide responses to questions. A Northern Data spokesman said the company’s revenue growth demonstrates the success of its strategic investments in AI.

Tether isn’t the first crypto company to spend big on deals. At its peak, crypto brokerage FTX splashed $1 billion on a bitcoin miner on the Kazakh Steppe and $500 million in AI-firm Anthropic.

Angermayer’s family office, Malta-based Apeiron Investment Group, has a business line making introductions between investors and companies. In some deals, Apeiron introduced cash-rich buyers to pricey investments that ultimately performed poorly.

In 2017, Angermayer’s family office helped Chinese conglomerate HNA Group become the largest shareholder in struggling German lender Deutsche Bank.

Shares in the bank slid further after the deal. HNA sold amid a cash crunch a few years later and hedges limited its losses. HNA, loaded with debt and under scrutiny by the Chinese government, eventually filed for bankruptcy.

Angermayer then started working with SoftBank Group, the Japanese conglomerate which had raised by far the world’s biggest venture capital fund. He introduced the company to Wirecard, a German payments processor that was at the time fending off accusations of accounting fraud.

SoftBank helped stabilize Wirecard via a $1 billion convertible bond. Both SoftBank and Wirecard paid Angermayer’s family office a multimillion–dollar fee for the introduction.

Months after getting the cash from SoftBank, Wirecard signed a long-term partnership with cybersecurity company Cyan AG, which was 27% owned by Angermayer and a business partner. That business partner had also served as HNA’s representative on Deutsche Bank’s board. Angermayer made introductions between executives at Cyan and Wirecard.

A year after the SoftBank deal, Wirecard collapsed in an accounting scandal. SoftBank had sold off the bond to investors who were largely wiped out.

A person familiar with the transactions said Apeiron was paid the market rate for the introductions and played no role in negotiating, analyzing or structuring the deals themselves. Angermayer also facilitated several other deals that were less controversial, the person said.

Of late, Angermayer and Apeiron have focused on what he calls the “Next Human Agenda," building a portfolio in fashionable sectors like cryptocurrency, longevity and psychedelic pharmaceuticals. He co-founded, with backing from tech investor Peter Thiel, the Enhanced Games, so called for the tournament’s embrace of performance-enhancing drugs, as an alternative to the traditional Olympics.

Angermayer often wears loud shirts bedecked with mushroom motifs. His forearm has a tattoo of the chemical symbol for psilocybin. He has hosted extravagant birthday parties at a 17th-century Austrian palace and at a Bahamian crypto conference. On Instagram, Angermayer shows off his collections of fossilized dinosaur bones and ancient sculptures focused on items inspired by psychedelic use.

The personal and professional at times intertwine. In 2022, Apeiron pitched investors on a new fund to be named “Apeiron Jurassic Fund One" that aimed to raise $30 million to invest in dinosaur fossils. Draft promotional materials said the fund would utilize “a unique global network of bounty hunters" and start with Angermayer’s collection of fossils including a juvenile tyrannosaurus rex and a diplodocus. The fund was ultimately abandoned.

Among Angermayer’s other investments was a significant stake in Northern Data, a German-listed bitcoin miner that has recently pivoted toward AI cloud hosting. Angermayer got part of that stake via Northern Data’s acquisition of two cryptocurrency mining companies in which Angermayer or his firms owned stakes. One was co-founded by a former employee of his family office.

Angermayer then began raising funds for Northern Data, and charging fees for the service.

Apeiron also billed Northern Data for introductions to investors. Charges included sponsoring and promoting the company at a Bahamas crypto conference bash that featured a shirtless performance by former One Direction star Liam Payne and purchasing tables at Elton John’s Oscar watch party. A person familiar with the transaction said Apeiron resold its tables to Northern Data at cost.

According to Northern Data’s financial statements, the company spent €840,000—equivalent to about $940,000—on Apeiron’s fundraising efforts in 2022.

Northern Data reported €420 million in losses from the acquisition of the two cryptocurrency-mining companies, according to financial disclosures. That, combined with broader declines in crypto assets in 2022, left Northern Data in a precarious financial position in early 2023, according to current and former employees.

A company spokesman said Northern Data has always operated successfully and that its audited financials show the company is currently well capitalized.

Angermayer found another deep-pocketed investor to step in: Tether

Tether first invested in Northern Data in the spring of 2023, paying €32.3 million for a stake in the company. Tether wanted to keep its involvement secret, according to people familiar with the transaction. Angermayer got a payment worth 5% of the deal’s value, the first payment he got for introducing the two companies.

Months later, Tether bought another €48 million of Northern Data shares. Again, Northern Data didn’t publicly identify Tether as its investor. A spokesman for Northern Data said both companies met their disclosure requirements around the transactions.

Angermayer received another 5% fee for the transaction. He was paid a total of €4 million for the two deals, according to invoices for the fees reviewed by the Journal.

With its early stake established, Tether began publicly helping Northern Data’s pivot to AI. Tether started an Irish company called DaMoon and lent it €400 million to buy advanced Nvidia H100 processors.

Northern Data then took over DaMoon. In return, Tether received newly issued Northern Data shares. Tether’s chief executive officer, Paolo Ardoino, described the investment in Northern Data in a podcast as “a perfect fit." He praised the company’s management, structure and teams.

Tether followed that by giving Northern Data a €575 million line of credit, which has been drawn down entirely. The deals left Tether the majority shareholder of the company. Last month, Northern Data said it would raise another €214 million—€110 million from Tether—to buy more processors.

A spokesman for Northern Data declined to answer whether Angermayer or Apeiron were paid fees tied to the later transactions. He said any fees paid by the company have been disclosed as required by legal and accounting standards.

Tether, which is based in the British Virgin Islands, has been wildly successful. Investors like it because its cryptocurrency is stable—it is always supposed to be worth $1. It is highly liquid, making it ideal for business transactions.

Tether has also proven useful for drug smugglers, terrorist groups and countries under sanctions, according to government indictments. Regulators have stepped up scrutiny and some banks have refused to do business with the company, government and bank officials have said.

Tether has said that it works with global law enforcement and has built and maintains world-class compliance programs to guard against money laundering, terrorism financing, sanctions busting and other risks.

Angermayer had another investment for Tether. He was co-chair of the board and the largest shareholder of Blackrock Neurotech, a manufacturer of brain-computer interfaces, small electronics implanted in paralyzed people’s brains to help them operate technology. The Salt Lake City-based company has been developing technologies since 2008.

Apeiron had led a $10 million investment round for Blackrock Neurotech in 2021. With Angermayer atop the board, former employees said, the company pushed toward going public, hoping to capitalize on the interest in the sector brought on by Musk’s Neuralink and the fervor of small investors.

But the business faltered. Former employees said Blackrock Neurotech expanded rapidly after the investment, more than doubling its head count and developing new business lines. That was followed by a series of layoffs in 2022 and 2023.

Last summer, Angermayer and Apeiron led a $37 million fundraising round. The company burned through more cash and had further layoffs, former employees said.

Blackrock Neurotech didn’t respond to requests for comment.

In April of this year, Tether swooped in and bought a majority stake in the company for $200 million, valuing Blackrock Neurotech at $350 million. The crypto company said it was branching out from merely providing a digital dollar alternative to now “empowering humans throughout the future inevitable evolution" with brain implants.

Northern Data, whose shares trade in Germany, is considering listing in the U.S. Some bankers pitching the deal to Northern Data have said it could be worth $20 billion in a few years, according to a slide deck reviewed by the Journal. The company declined to comment on a possible U.S. listing.

Eliot Brown contributed to this article.

Write to Ben Foldy at ben.foldy@wsj.com and Caitlin Ostroff at caitlin.ostroff@wsj.com