Alongside a two-lane road in Mountainside, New Jersey (population 7,020), is a small blue and white sign reading “YA,” which might be interpreted as an upbeat, blurted affirmative or as shorthand for a category of teen fiction, but is actually the logo of Yorkville Advisors. The firm’s office, a humble one-story building, is at the bottom of a small hill and hidden by hedges. Inside, billions of dollars in deals are engineered, including some for a very prominent client, a business associated with the president of the United States.
Donald Trump and his family’s efforts to cash in on his return to the White House are broad and audacious, from Trump’s millions of dollars in World Liberty crypto to the Trump Organization’s licensing of the Trump name for a mobile-phone service costing $47.75 a month: Call 888-TRUMP45 now to sign up! The multifaceted drive has also been wildly lucrative. Forbes, in March, estimated that in the past year Trump’s net worth has more than doubled, to more than $5 billion. The New Yorker, in August, calculated that Trump and his family had profited approximately $3.4 billion off of Trump’s two presidencies.
Some of the leaders of Trump’s new financial empire are familiar, such as sons Don Jr. and Eric, who are officially in charge of the Trump Organization, and Devin Nunes, the former California Republican congressman, who is now the CEO of the Trump Media & Technology Group, which operates Truth Social, the X alternative that is Trump Media’s highest-profile property. And some of the company’s institutional investors are financial industry heavyweights, including the Jane Street Group, the Vanguard Group, and Cantor Fitzgerald, the firm formerly run by Howard Lutnick, who is now Trump’s commerce secretary.
But Yorkville is largely unknown beyond financial circles. How did the previously inconspicuous firm become an integral part of Trump’s financial orbit? Yorkville and its founder, Mark Angelo, aren’t saying, and neither is Trump Media; both companies did not return requests for comment. Angelo does not appear to have donated to any of Trump’s presidential campaigns, though he contributed $1,000 to Hillary Clinton’s 2008 bid. Yet a July 2024 press release announced that Trump Media and Yorkville had struck a standby equity purchase agreement—similar to a line of credit, in which Yorkville agreed to buy a set amount of Trump Media’s shares at Trump Media’s discretion.
Last year Trump Media put the deal into effect, selling about 20 million shares at a discount to Yorkville and generating nearly $450 million in cash. In January came the announcement that an affiliate of Yorkville would serve as the registered investment adviser for Trump Media’s new financial services arm, Truth.Fi, which plans to offer exchange traded funds and other products that will invest in the “patriot economy.” In August, Yorkville Acquisition, a SPAC that’s affiliated with Yorkville Advisors and of which Angelo is the chairman, and Crypto.com teamed up with Trump Media to launch Trump Media Group CRO Strategy, a firm that said it was expecting to acquire $6.4 billion to buy CRO crypto tokens. A Yorkville affiliate would provide the new company with a $5 billion equity line of credit. Last week the Cayman Islands–incorporated Yorkville Acquisition announced that it would be renamed to Trump Media Group CRO Strategy.
On the surface the pairing seems unlikely: One of the world’s most famous, most powerful men is relying on an inconspicuous suburban financial firm. But in some respects Trump and Yorkville appear to be a natural alliance. “[Trump Media] is a risky, controversial, early-stage company without a lot of revenue, without a lot of operating history, and in need of cash. And that’s just the kind of company that Yorkville gets involved with,” says Justin Hibbard, a CPA and former examiner for FINRA who has written about Yorkville on his Substack, “Shortfinder.” “They do a lot of business with biotech companies, life science companies that are at a very early stage of development. They seem to pretty consistently liquidate their positions at prices that are favorable for Yorkville. They’re good at what they do.”
In April, Yorkville made a standby equity purchase agreement with Newsmax. The Fox News alternative can raise up to $1.2 billion in cash by selling shares to Yorkville, an arrangement that Hibbard has highlighted as risky because it could dilute the value of Newsmax stocks on the market. Chris Ruddy, the Newsmax CEO, declined to comment.
The overlap between Trump and Yorkville seems mostly motivated by dollars and cents, with an overlay of anti-woke culture war marketing. The two principals may also share a sense of grievance about government regulators. Trump is continuing to fight a fraud conviction in New York, claiming that the case against him is a partisan political vehicle for Democratic state attorney general Letitia James. Angelo, the founder of Yorkville Advisors, has said he spent more than nine years tangling with the SEC, which claimed that the firm had overvalued assets to hide losses from investors. A federal judge ultimately tossed out most of the civil fraud charges, and Yorkville and the SEC agreed to dismiss the case.
Angelo felt vindicated. “We were losing money, were forced to lay off important members of our team and were dealing with the coercive pressure of an SEC lawsuit—those were pretty dark days,” he told a website called Thrive Global in 2019, after the case was dismissed. “The allegations never should have been brought and we were victims of circumstance.” Angelo told “IA Watch,” an investment firm newsletter, that “the entire system is stacked against you…. It is designed to make you settle.” Those are perspectives his most famous client can certainly appreciate.
During Trump’s first term, his Washington hotel drew a lot of attention, but it lost money during that time, according to the House Oversight Committee in 2021. (At the time, the Trump Organization disputed the assessment, calling it “intentionally misleading, irresponsible and unequivocally false.”) This time around, Trump’s business pursuits, if highly dubious ethically, are much more efficient financially. Crypto, unlike a hotel, doesn’t need to pay a mortgage. “I don’t think you should have to become poor while you are president,” says Jeff Hauser, executive director of the Revolving Door Project. “But I do think you shouldn’t be spending your time thinking about how to become rich.”
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