Truth Social reaches a tricky milestone. Will Donald Trump cash out his stake?

Trump Media's future is becoming even more uncertain.

The parent company of Truth Social, the social media company majority-owned by former president Donald Trump, is turning a complicated corner on Thursday. A lockup on insider sales is due to expire—meaning that Trump could start cashing in his 57% stake, which is currently valued at about $2 billion.

Shares in Trump Media fell more than 4% on Thursday morning, at one point hitting an all-time low of $14.77. The share price is down nearly 80% since Trump Media went public in March. (The stock trades under the ticker DJT, for "Donald J. Trump.")

Trump said last week that he has "absolutely no intention of selling" his stake in Truth Social. Some investors take him at his word, at least for the time being, since such a sale would likely further depress the price of Trump Media's shares.

"The stock price of Truth Social is like his crowd size," said professional investor Matthew Tuttle, in a reference to Trump's ongoing fixation with the attendance at his rallies and other campaign events.

"He's not going to want to see the stock price go down. And if he sells, it is going to do down," says Tuttle, who runs the investment firm Tuttle Capital Management, and who used to trade the Trump Media stock personally.

But now that the lockup is expiring, Trump is free to eventually change his mind and cash in some of his stock.

Trump Media did not respond to a request for comment from NPR.

Truth Social's future is also tied to the election

Trump Media is a quintessential meme stock, bought and sold more for what it stands for than for any underlying business performance.

The company reported a loss of more than $16 million in its most recent quarterly earnings, and there are