In the ever-evolving landscape of social media, Donald Trump's latest venture, Trump Media & Technology Group, seems to be facing a new challenge amid the anticipation of the 2024 election. The success of the startup, known for its Truth Social platform, is heavily reliant on the reputation and popularity of Trump himself, according to the company. However, recent polls showing a drop in Trump's popularity after Kamala Harris emerged as the Democratic nominee have caught the attention of both Wall Street and MAGA investors.

The volatility in Trump Media's stock price reflects this uncertainty. After a brief surge following an assassination attempt on Trump's life, shares have plummeted in recent weeks. On Tuesday, the stock closed at its lowest price since its debut in the public market five months ago, despite the general upward trend in the stock market.

The rollercoaster ride for Trump Media has been marked by significant jumps in the stock market, legal battles, and dismal financial results. In the second quarter alone, the company reported a loss of over $16 million. This decline is now posing a threat to one of Trump's major sources of wealth.

Currently, Trump holds a substantial stake of more than 114 million shares in Trump Media, which amounts to approximately $2.5 billion. While he is prohibited from selling his shares due to a lock-up agreement, this restriction is set to end in September. Cashing out would represent a significant opportunity for Trump, allowing him to potentially pay off legal bills or even finance his own campaign leading up to the November elections.

However, the process of selling Trump Media shares won't be simple or immediate. This looming possibility of a substantial sell-off by Trump is causing concern among shareholders who fear a sudden expansion of the company's float, particularly considering Trump's cash needs prior to November.

Despite returning to mainstream social media via X (formerly known as Twitter), Trump seems to be reserving his controversial online activity for Truth Social. With 89.7 million followers on X and 7.6 million on Truth Social, Trump appears to be focused on building out his own platform.

To that end, Trump Media recently introduced in-app streaming on Truth Social, its prized asset. The company stated that it has $344 million in cash and cash equivalents, with zero debt. These efforts aim to strengthen the business, but the ultimate fate of Trump Media hinges on the outcome of the upcoming election.

According to Matthew Tuttle, CEO of Tuttle Capital Management, as long as Trump's popularity continues to suffer in the polls, the company's stock price will not find a solid floor. However, a Trump victory in the 2024 election could potentially turn things around for Trump Media.

The uncertainties surrounding Trump Media's future and its heavy reliance on Trump's reputation and the election outcome highlight the challenges faced by the company. With the lock-up agreement ending in September, the anticipation of whether Trump will sell his shares adds further complexity and speculation to the situation. As the media landscape continues to evolve, Trump Media's journey remains uncertain, awaiting the outcome of the 2024 election.