Who is Kyle Wool, who helped the Trump family earn 500 million dollars?

Original authors: Annie Massa, Zachary R Mider, Bloomberg
Translated by: Luffy, Foresight News

 

One of the latest tenants in New York's Trump Tower is a startup investment bank called Dominari Holdings Inc. Located two floors below the Trump Organization headquarters, Dominari President Kyle Wool considers this “proximity” a point of pride.

For years, Wool has worked to maintain relationships with the Trump family. Since last year’s election, he has gradually become a financial advisor to the president’s two sons and several Trump Organization executives, jointly facilitating a series of high-profit deals.

Dominari’s offices are on the 22nd and 23rd floors, a glamorous space that once housed the Tommy Hilfiger family office. On an afternoon in July, a TV at the entrance was tuned to Fox Business Channel, and a shelf nearby displayed transparent trophies commemorating successful fundraising cases for corporate clients. Most of these clients are not household names—Dominari specializes in financing micro-cap companies. These companies are publicly listed but have small market capitalizations and highly volatile stock prices, with fluctuations driven more by market hype than earnings expectations. This also explains why Wool’s collaboration with the Trump family has been so “fruitful.”

The Trump Name: A Hype Engine for Micro-Caps

The Trump name happens to provide the kind of buzz that stock promoters crave most. Take, for example, Unusual Machines Inc., a loss-making drone company in Orlando. Three weeks after the 2024 election, news broke that Donald Trump Jr. would serve as a paid advisor and investor for the company—a deal brokered by Wool. Securities filings show the company’s stock price more than doubled in three days, netting the president’s eldest son a paper gain of $4.4 million.

Since then, similar collaborations have emerged: tying Trump family members to previously obscure stocks, then leveraging the ensuing publicity to drive up share prices.

When Trump’s sons became advisors, Unusual Machines and Dominari Holdings stock prices soared

One such collaboration involved Dominari itself. In February, the company announced that Donald Trump Jr. and Eric Trump would serve as advisors and investors, holding more shares than any other outside investor. The announcement did not mention their father, President Trump, only stating that the two would provide consulting in artificial intelligence and data centers—even though neither has obvious experience in these fields. Nevertheless, Dominari’s stock price surged, bringing millions in wealth to Wool and the Trump brothers.

As of October 9, the Trump brothers’ holdings in Dominari were worth over $17 million; Eric’s stake in a bitcoin mining company established with Dominari was worth nearly $500 million—even by Trump family standards, an enormous windfall.

A Trump Organization spokesperson did not respond to requests to interview Eric and Donald Jr. In February, after the Trump brothers were appointed as Dominari advisors, Wool said in an interview that they were excellent businessmen, but declined to comment for this article. After receiving a summary of the Bloomberg Businessweek report, Dominari said it “contains inaccurate statements and misinterpretations,” but did not specify the issues or arrange executive interviews. The White House also did not respond to requests for comment.

Eric and Donald Jr. outside the Nasdaq in New York in August

Dominari’s business model is a new variant of the Trump family’s tradition of “monetizing fame.” The Trump Organization’s real estate business has long since shifted from building projects to selling the rights to use the Trump brand; their collaborations with Wool and micro-cap stocks, as well as recent ventures into cryptocurrency, are all ways of trading reputation for wealth.

“A typical feature of micro-cap companies is that they are always striving to attract attention,” said Stephen Kann, author of *Microcap Magic: Why the Biggest Returns Are in Stocks You’ve Never Heard Of* and a banker who worked at Dominari for several months last year. “Being associated with the Trump family is like putting a spotlight on them.”

For other presidential families, involvement in the micro-cap sector might be seen as a reputational risk, as these companies have a long record of “losing money for investors.” As Warren Buffett once said, if American capitalism is a cathedral with a casino attached, then micro-caps are like roulette and slot machines.

About half of Dominari’s IPO projects are small companies headquartered in mainland China or Hong Kong, a sector notorious for wild price swings and fraud. This ecosystem is fueled by a steady stream of small investors: they flock to the micro-cap casino, hoping for quick profits. Now, thanks to Wool, America’s first family has joined their ranks.

Such collaborations also carry potential conflicts of interest. During Trump’s first term, public concerns about conflicts focused mainly on the family’s real estate projects, where lobbyists and foreign officials could indirectly enrich the president by hosting events or booking rooms at Trump hotels.

In this term, the Trump family’s business interests are even broader, spanning media, mobile phones, cryptocurrency, and more. Eric and Donald Jr. insist they are private businessmen, but their father’s policies as president could, to some extent, affect the companies they work with. Dominari has become a channel for the family to access these new opportunities, greatly increasing the likelihood that official decisions could boost Trump family wealth.

Kyle Wool: The Networker from Rural New York

Wool grew up in Candor, a rural town in upstate New York with a population of about 5,000. After college, he entered the brokerage industry, quickly managing assets for the wealthy at firms like Oppenheimer and Morgan Stanley. His clients included Korean professional golfers, a timeshare tycoon (whose 90,000-square-foot mansion appeared in the 2012 film *Queen of Versailles*), and even a company co-owned by Hunter Biden, son of then-Vice President Joe Biden.

The job itself was unremarkable, but Wool stood out in other ways. He once appeared in a fashion magazine with friends, showing off a $165,000 watch; he also cultivated close ties with the Serbian royal family, participating together in humanitarian charity work in that country.

In October 2018, Wool attended the annual charity luncheon of the Liedkranz Foundation with Crown Prince Alexander of Serbia

In 2022, Wool became president of New York-based boutique brokerage Revere Securities, which specializes in financing micro-cap stocks (typically companies with market caps below $250 million; regulators often warn investors that such stocks are riskier and prone to fraud). His clients included Anthony Hayes, a lawyer friend who had also appeared with him in a fashion magazine.

At the time, Hayes was CEO of a Nasdaq-listed company that had repeatedly shifted its business—from food sweeteners and pesticides to patent litigation and cancer drugs—accumulating tens of millions in losses along the way. On Wool’s advice, the company pivoted again to become an investment bank and was renamed Dominari—Latin for “to control.” According to a former colleague, Wool loved the word: “He’d say over and over, ‘I control, I control, I control.’” Soon after, Wool was named president of Dominari and head of its securities division.

Meanwhile, according to two people who worked with Wool, he began focusing on building relationships with the Trump family. He moved the company’s headquarters to Trump Tower and invested time and money in Trump properties—he is a member of the “Trump Club” in Jupiter, Florida (current membership fee: $500,000), and has organized events at another Trump golf course. Before long, he was holding private fundraising events with Trump’s sons and other Trump Organization executives.

“Dominari has brought us a lot of opportunities, and many have been incredibly successful,” Eric said in an interview with crypto media outlet Fintech.TV in April. “Every time I see them, I get really excited.”

The Trump Brothers: From Avoiding Conflicts to Unrestrained Activity

As executive vice president of the Trump Organization, Eric oversees the family’s daily business operations; Donald Jr. holds the same title but is more active in “MAGA (Make America Great Again)” media activities. Both have complained that during their father’s first term, they tried to avoid conflicts of interest by forgoing new overseas real estate projects, yet were still criticized. “In 2016, I tried to do everything right and got almost no recognition,” Eric told the Wall Street Journal last year. In this term, their restrictions have been greatly reduced.

Like the Trump brothers, Wool frequently shuttles between New York and Florida’s MAGA enclaves, as evidenced by his often sun-tanned complexion on Fox Business Channel. His slicked-back hair evokes the image of 1980s Wall Street power brokers. On air, he always delivers mainstream investment talking points (AI stocks are hot, the market will rise) and heaps praise on President Trump.

Kann, the micro-cap expert who worked at Dominari, described Wool as “very sociable,” happy to drink and joke, but hardworking and fully committed to the company’s growth. Unusual Machines CEO Allan Evans said, “He’s the typical New York banker who will do whatever it takes to get the job done—Saturday, Sunday, even at 2 a.m., if there’s work to do, he’ll do it.”

Over the years, Wool has received five customer complaints with the Financial Industry Regulatory Authority, alleging “unsuitable investments,” “unauthorized trading,” and more. Two complaints were withdrawn, two settled, and one is still pending. Wool denies any wrongdoing and, in a February interview, called such complaints industry norms: “After so many years in this business, it’s inevitable.”

Evans at the Unusual Machines store in Orlando

The Trump Effect at Unusual Machines

Unusual Machines’ office is in Suite J of a warehouse in Orlando’s industrial district. When reporters visited in late June, the company was hiring aggressively, with new desks and workstations crowding the office and boxes of equipment stacked nearby. The company had fewer than 20 employees, most in retail, selling mainly Chinese-made drone parts to hobbyists. But CEO Evans planned to more than double the staff, open a factory to make parts in-house, and pursue new industrial and government contracts.

Near the loading area, an employee demonstrated the company’s smallest product—a buzzing, white, square drone, only slightly larger than a loaf of bread, flipping nimbly in the air. Earlier this year, at Mar-a-Lago, Donald Trump Jr. had flown a similar drone in the banquet hall to showcase its performance. “He flew pretty well,” Evans said.

Without Donald Jr., the company’s prospects might have been much dimmer. Unusual Machines started as an orphaned business: last year, its former owner decided to focus on military sales and spun off the consumer business, with Wool helping it list at $4 per share. But after listing, investors were lukewarm, the stock fell below $2, and the company’s cash dwindled.

An employee assembles drone parts at Unusual Machines

As Wool scrambled to raise more funds, he recommended the stock to Donald Jr. Evans said the president’s son was intrigued—Donald Jr. has a pilot’s license and experience using drones for deep-sea fishing. A securities filing shows he paid $100,000 for shares and warrants, and eventually agreed to sign on as an advisor.

After the announcement of Donald Jr.’s involvement last November, the company’s stock soared above $20, with his investment multiplying 30-fold. Since Donald Jr. is not an executive or director at Unusual Machines, he is not required to disclose the timing or amount of his trades. But Evans said Donald Jr. continued to invest in subsequent funding rounds.

In the micro-cap world, it’s not uncommon for “attention-grabbing announcements to drive up stock prices, followed by insiders dumping shares and causing a crash.” But Evans said they didn’t do that: “If we were ‘pump and dump,’ we would have raised money or I would have sold shares when the stock hit $20. In fact, I bought in every round and never sold. Our team believes in the company’s future.”

Unusual Machines’ foray into domestic manufacturing makes it one of dozens of American startups betting on government and commercial demand, as buyers grow wary of China, the world’s leading drone maker. Some rivals have deep-pocketed backers or valuable patents, but Unusual Machines’ edge is Donald Trump Jr. Evans said he hasn’t lobbied the White House or tried to curry favor with the Pentagon: “Donald Jr. has a better sense of macro trends than I do. When you’re having lunch on a private jet with Elon Musk, you have a clearer view of where automation is headed.” (Evans made this comment just days before Musk’s public spat with the White House.)

Evans believes Donald Jr.’s biggest contribution is his public support for the company. He said it’s now easier to meet potential business partners, and the company has raised over $80 million from investors this year. “Just this association gives us more credibility and helps us stand out. It’s like Oprah joining the WeightWatchers board—does Oprah need to do anything? Almost nothing.”

American Bitcoin’s $500 Million Fortune

Wool also helped the Trump family score a huge windfall in the crypto sector—American Bitcoin. During Trump’s second term, his two sons have been involved in multiple crypto projects: traveling the world to attend industry conferences and promoting their father’s crypto-friendly stance.

Earlier this year, the Trump brothers, together with Wool, Dominari, and others, acquired a 20% stake in a mature bitcoin mining company with mines in Texas, New York, and Alberta, Canada. The company then went public via a merger with a micro-cap, rebranding as American Bitcoin.

In May, the Trump brothers appeared at the largest bitcoin industry conference in Las Vegas to promote the company’s prospects and emphasize its alignment with their father’s pro-crypto vision. On stage, Eric said: “We have a president who loves this industry and supports it 100%. I can tell you, our family is incredibly excited about this company and its future.”

The deal brought Wool a huge payday. As of October 9, Dominari’s stake was worth over $150 million; Eric’s was worth nearly $450 million.

“I am incredibly proud of American Bitcoin,” Eric said in a text message. “It’s been an amazing success.” He did not respond to other questions about his relationship with Dominari, and American Bitcoin did not respond to separate requests for comment.

The Trump brothers’ holdings in Dominari-related deals

Conflicts of Interest Everywhere

As in the drone sector, conflicts of interest in crypto are also obvious. While there is no evidence that the Trump brothers’ investments have influenced policy decisions, the value of these companies could rise or fall based on government actions. In July, the White House recommended that the IRS consider revising long-standing tax guidelines for crypto mining—a move the industry has lobbied for, which would benefit companies like American Bitcoin.

Meanwhile, the company’s mining computers are made by a manufacturer based in China. Recently, a Republican lawmaker asked the U.S. Treasury to review such imports for national security reasons—a decision that rests with the Trump administration.

In the drone sector, the Trump administration is also pushing for domestic production, continuing a bipartisan initiative started under the Biden administration. In June, Trump signed an executive order to accelerate the rollout of long-sought flight rules; in July, the Pentagon issued guidance to speed up U.S. military drone procurement. Both moves boosted U.S. drone stocks this year.

Conflicts of interest have not deterred Wool and the Trump brothers from collaborating. In August, they launched their latest project: a blank-check company called New America Acquisition I Corp. (a special purpose acquisition company, or SPAC). The company will raise funds in the stock market, then acquire a domestic manufacturer in line with “Trump’s Made in America vision.”

As part-time advisors, the Trump brothers will receive shares potentially worth up to $50 million after the company goes public. In a securities filing, New America Acquisition said it would seek acquisition targets that could benefit from federal or state incentives such as subsidies, tax credits, government contracts, or preferential procurement programs. But after the Associated Press inquired about this, the company deleted the statement, with its lawyer blaming a “filing error.” New America Acquisition did not respond to requests for comment.

Dominari’s IPO Controversy: Success and Disaster

Dominari executives are pleased with the company’s fast-paced dealmaking. In a June letter to shareholders, CEO Hayes declared he was “very proud of the company’s achievements”: revenue growth, rising stock prices, and he credited the advisory board—then made up entirely of Trump Organization executives, including Donald Jr., Eric, and lesser-known company veterans Lawrence Glick, Alan Garten, and Ronald Lieberman.

Hayes also boasted of 12 recent IPOs completed by Dominari, including companies operating two golf courses in Florida and building roads in Hong Kong. He wrote: “Some media have unfairly described some of our recent IPOs, implying poor client quality. We strongly disagree.”

To be sure, some investments have brought significant returns for investors (such as Unusual Machines), but of the 12 deals Hayes cited, five were disasters, with share prices nearly halved after listing. While “the Trump family is not involved with most companies Dominari helps list,” under Wool’s leadership, these IPOs have become a key part of the business.

Among the 12 IPOs Hayes touted was Everbright Digital Holding Ltd.—a Hong Kong marketing company with just seven employees, claiming deep involvement in the metaverse. Dominari helped it list on Nasdaq in April at $4 per share, but investors were initially indifferent; then in June, trading volume suddenly surged and the stock price soared above $6.

This rally was driven by online stock-picking clubs. Such clubs are increasingly popular, with so-called “experts” often posing as U.S. fund managers on social media, encouraging American investors to buy stocks for quick profits. Artsyom Yefremenka, a 31-year-old auto mechanic in Fresno, California, said he joined a stock-picking club on the messaging app Viber. The club leader, “Mr. James,” had previously given several profitable stock tips. So when Mr. James urged members to “buy Everbright Digital Holding in a big way,” Yefremenka invested about $20,000—nearly half a year’s salary.

In mid-July, Everbright Digital Holding’s stock crashed, falling below $1. During his lunch break, Yefremenka watched his investment evaporate: “I thought, ‘I can’t be this stupid, to get scammed so badly.’ It was greed that got us all.” Everbright Digital Holding did not respond to inquiries.

Everbright Digital Holding stock price collapse

Micro-cap stocks have always been hotbeds for fraud and manipulation, and the recent trend of hyping them via messaging apps is drawing attention from U.S. regulators and law enforcement. Criminals sometimes “buy up large amounts of a company’s stock, then use stock-picking clubs to sell at high prices.” In July, the FBI said complaints about pump-and-dump scams involving messaging apps had risen 300% from last year, with estimated losses to U.S. investors in the billions of dollars.

Last month, the SEC announced a special task force to investigate “cross-border pump-and-dump scams,” including reviewing underwriters who may help market manipulators access the U.S. listing system. Since Dominari’s founding, 18 of its 38 IPOs have involved small companies based in mainland China or Hong Kong. Some companies’ reasons for listing in the U.S. are unclear: one runs three hot pot restaurants, another is a luxury watch dealer with just seven employees. Several companies saw their stocks soar after being hyped by stock-picking clubs, then crash—such as healthcare company Pheton Holdings Ltd. (which lost over 80% of its value after listing) and Skyline Builders Group Holding Ltd. (which fell over 87% in a single day in July).

There is no evidence that Wool or Dominari are connected to stock-picking clubs or involved in price manipulation. The company’s revenue comes from listing fees, and it usually does not participate in company affairs afterward; there is also no evidence Dominari is under SEC investigation. It is simply one of several investment banks helping speculative Chinese companies list in the U.S.—but this does aid fraudsters.

“These companies keep going public, their stocks soar and then crash,” said Michael Goode, a Michigan micro-cap investor and blogger. “That either means some investment banks are turning a blind eye to this, or these fraudsters are very good at hiding their tracks.”

According to former colleagues, Wool has been telling people for months that “this period has changed his life”—Dominari’s successful partnership with the Trump family has opened more doors for him. In June, Wool helped a toy-making micro-cap pivot to become a “holder of cryptocurrency created by billionaire Justin Sun.” While the deal didn’t directly involve the Trump family, Wool told the Wall Street Journal that Eric Trump had vouched for him to Justin Sun, saying “Wool is a good guy.”

Wool also told the Wall Street Journal that hedge funds and executives are now suddenly reaching out, hoping to do deals: “Now they want to be friends with me? I don’t need that.”

When Wool traveled to South Korea on business this year, he was treated like an unofficial ambassador. He shared his views on the new U.S. administration in a TV interview and met with former Korean lawmaker Yang Ki-dae. On Facebook, Yang called Wool a “potential bridge between Korea and President Trump,” and mentioned that Wool had invited him to “visit Trump Tower next time he’s in the U.S.”