Facing a $2 billion decision, Trump says he will keep his Truth Social shares

After waiting six months -- and losing $4 billion on paper -- former President Donald Trump faces a potential windfall from his social media company.

Half a year after the public company behind Trump's Truth Social platform went public, the "lockup" agreement that prevented Trump from selling any of his 115 million shares expired on Thursday afternoon.

Beginning to sell his shares could allow Trump to profit handsomely from his stake in the company -- which is currently valued at approximately $1.7 billion -- but it could crater the stock for the company's diehard supporters, many of whom invested their money in the company as a sign of their support for the former president.

At the same time, holding onto the investment would be a financial leap of faith for Trump, whose shares comprise a large percentage of his net worth but have lost billions of dollars in value over the last six months.

Asked about the choice last week, Trump vowed not to sell.

"They're worth billions of dollars, but I don't want to sell my shares," Trump said. "I'm not going to sell my shares. I don't need money."

Trump's choice comes amid new financial pressures and a significant reshuffling of his financial portfolio.

While Trump's net worth has grown to $4.3 billion according to the most recent Forbes estimate, the former president owes over $560 million in civil judgments, which he is actively appealing. The majority of his personal wealth -- once built on the namesake properties that shot him to fame -- now stems from his shares in his social media company, Trump Media & Technology Group, which have fallen more than 70% since the company went public.

Analysts, meanwhile, have expressed concern about a further decline if Trump loses the November election.

Shares in Trump Media closed at a new low of $14.70 Thursday ahead of the lockup provision expiring, though the company enjoyed a 25% surge last week after Trump announced his plan to hold his shares.

"When he's promised to do something, he's kept his word," said Jerry Dean McLain, a shareholder who purchased a hundred additional shares after Trump's pledge. "He's loyal to his followers -- to his people -- so I don't have any reason not to believe him."

'Nothing like this'

Trump turned to the idea of creating his own social media company in the months following his ban from Twitter and other social media companies after the Jan. 6 attack on the Capitol. Truth Social launched in 2022, billing itself as a beacon for free speech on the internet with larger plans to expand into streaming.

"All of a sudden, I went from being No. 1 to having no voice," Trump said about the benefit of Truth Social. "I'm not going to let that happen again."

Despite multiple roadblocks -- including a dispute with the company's cofounders, and its special purpose acquisition company paying a fine to settle fraud charges with the Securities and Exchange commission without admitting wrongdoing -- the social media company went public in March.

Shares in the public company peaked at $66 in April, with analysts comparing the company to so-called "meme stocks" like AMC and GameStop, whose share prices surged based on investor enthusiasm rather than financial metrics.

By the summer, Trump Media's stock price lingered around $30 before slumping to the teens in September, which some experts still believe is overvaluing the company, which only brought in $836,000 in revenue last quarter -- a 30% decline from a year earlier. Based on the company's cash per share, the stock is overvalued by 1,000%, according to University of Florida finance professor Jay Ritter.

With the company losing millions of dollars, reporting limited revenue, and offering an unproven business model, the stock's performance has frequently tracked with Trump's personal wins and losses. When Trump was convicted on 34 counts of falsifying business records in New York, the stock declined 14% in after-hours trading following the verdict. Shares then surged as much as 30% early trading on the Monday after Trump survived an assassination attempt in Butler, Pennsylvania.

"It's much more of a speculative half-proxy for the former president's reelection prospects and half kind of a long shot early-stage opportunity to get in on a potential new tech company and social media platform," said Tyler Richey, an analyst at Sevens Report Research.

While it's not unusual for a company's stock price to fluctuate based on its corporate leadership, Trump's relationship to the value of his company stands alone, according to Mike Stegemoller, a finance professor at Baylor University. Trump is the platform's most notable user, he attracts new members to the platform, and he is the company's largest shareholder.

"Publicly traded corporations ... are somewhat dependent on personalities, but nothing like this," said Stegemoller. "You're getting this asset that generates cash flows, and you're coupling that with a personality that's pulling revenue to that asset."

In regulatory filings, the company has acknowledged the risk of being tied to the former president. If Trump were to sell his shares or begin using another social media platform, the company's stock value could suffer.

Trump, for his part, has vowed to continue posting on Truth Social.

"I love it. I use it as a method of getting out my word," Trump said last week regarding the platform.

'A much more profitable deal'

The lockup agreement that's kept Trump from selling off his shares in the first six months is an arrangement that's often used by public companies to prevent company leadership from taking actions that could affect the stock price, according to Ritter.

Trump's 115 million shares means he owns more than half of the company, so selling those shares -- which Trump would have to disclose within two days in a public filing -- could trigger a massive selloff and tank the company's stock price.

"As soon as folks know he's getting out in any large amount, I would imagine shares would fall," said Stegemoller.

According to Stegemoller, Trump's announcement last week that he would not sell his shares is reasonable -- not only because Trump likely wants the company to succeed, but also because selling his shares too rapidly could cost him money. Because he holds so many shares, Trump would be unlikely to fully offload them all before the stock price plummeted, forcing him to sell his remaining shares at a lower price.

Alternatively, Trump could slowly sell some of his shares, arrange a deal with a buyer, or use the shares as collateral for loans. Selling some of his shares would allow Trump to still own a controlling interest in the company while diversifying his portfolio, according to Stegemoller.

"Selling slowly over time in order to pull money out of his investment is a much more reasonable deal for him, and a much more profitable deal for him, too," Stegemoller said.

Although Trump has publicly declared that he plans to hold his shares, executives in the company could consider selling their holdings, which could also impact the stock price.

"They might want to get out as quickly as possible, and rather than sell their shares gradually, it might be a rush for the exit," said Ritter.

'I'm not leaving'

Trump has suggested that the company's sluggish stock performance is partially due to speculation about him stepping away from the company -- a notion he tried to dispel last week.

"People think that I'm leaving. That's why they're down," Trump said regarding shares in the company. "It's different if I leave, but I'm not leaving. I love it."

And some analysts believe the expiration of the lockup provision could prove to be a turning point for the company.

According to Richey, a recent spike in trading volume and other metrics suggest that the stock price might be reaching a bottom, while Trump's decision to hold his shares could reassure investors.

Speculation about Trump's chances of winning in the November election could also help the stock price.

"There's still money in the markets supporting a Donald Trump win if you're using the stock price as a proxy for the election outcome," Richey said.