AI Financial, a publicly traded crypto firm tied to President Donald Trump’s family, has purchased a startup owned by one of the company’s own advisors. According to filings with the Securities and Exchange Commission, the Las Vegas-based company struck a deal last Monday worth up to $43 million to buy the crypto infrastructure business Block Street.
Corporate records show Block Street was only incorporated in Nevada in late October. Matthew Morgan, the advisor to AI Financial, who is also the CEO and biggest shareholder of Block Street, said he founded the company about 16 months ago.
Formerly called Alt5 Sigma, AI Financial rebranded on Wednesday and is a public company whose business has swung between biotech, fintech, and now crypto. In August, the firm struck a deal with World Liberty Financial, a Trump family crypto company, to stockpile $1.5 billion in cryptocurrency on its balance sheet. In return, World Liberty Financial received stock in AI Financial and board seats.
The arrangement coincided with a 2025 fad that saw small publicly traded companies load up with cryptocurrency in order to spur a pop in their share prices.
AI Financial’s decision to acquire Block Street is notable given that the crypto deal in August saw Morgan named as chief investment officer before the appointment fell through amid a reshuffling of the C-suite. He later became an unpaid advisor, he told Fortune in an interview.
Morgan said the acquisition of Block Street isn’t a form of self-dealing. He shopped his business, which isn’t generating revenue, to a number of different public companies in late 2025 and rejected deals that promised potentially more than $100 million in “upside,” he told Fortune.
Since August, when AI Financial first announced its ties with the Trump family’s crypto company, the stock has cratered more than 90% amid the broader downturn in the crypto market. Morgan said AI Financial acquired his company because the public firm wants to do business in two areas in which Block Street has expertise: tokenization, or putting assets like stocks in blockchain wrappers; and initial coin offerings, or launching cryptocurrencies.
‘Cannabis king’
Morgan found his way into the Trump family’s crypto circle through his friendships with serial entrepreneurs Chase Herro and Zak Folkman, who helped create World Liberty Financial, one of the most lucrative ventures in the Trump family’s crypto portfolio. (President Donald Trump, as well as his sons Eric, Donald Jr., and Barron, were once listed as cofounders on the website for the project.)
Morgan met Herro and Folkman when they were young, he said, though at the time, the three pursued separate business interests. Morgan went into legal cannabis and said on a podcast that he built “over $1 billion worth” of marijuana companies. In an earlier episode, the podcast dubbed him the “cannabis king.”
In the mid-2010s, Morgan said he became interested in crypto and stayed in touch with Herro and Folkman. The duo brought Morgan on as an advisor to World Liberty Financial in September 2024 when they launched the project. In a post on X, the Trump family crypto company called Morgan a “leading game developer” on the messaging app Telegram.
Now, the former marijuana mogul has become the “global head of vision” at AI Financial. Morgan, who touted his former business success in an interview, said he’s working with the company’s executives to buoy its beleaguered stock. “I think everyone’s upset,” said Morgan, “and I think everyone wants to figure out a way to rectify the situation.”
But, he believes he can help resuscitate the flagging firm. “We’re going to turn this thing around quickly,” he said. “I’m not worried at all.”
AI Financial’s deal for Block Street is the latest example of a public, crypto-hoarding firm buying up a business connected to insiders. In February, David Bailey, the CEO of a Bitcoin company, agreed to buy his own media and investment firms. And, in March, shareholders of a Bitcoin company run by businessman and finance influencer Anthony Pompliano voted to buy a startup he partially owned.
The apparent self-dealing has led to critiques. In a March letter, the activist investor Gabi Gliksberg urged board members of Pompliano’s public company, ProCap Financial, to reject “a deal in which he [Pompliano] sat on both sides of the table.”
In a statement to Fortune, a spokesperson for ProCap Financial pushed back on the critique: “The ProCap Financial shareholders overwhelmingly voted to approve this merger.”
