Last month, Donald J. Trump’s fledgling social media company announced that it had lined up $1 billion from 36 investors.
The size of the deal, the former president said in the announcement, signaled that his start-up’s plan to end the “tyranny” of Big Tech had significant support.
Getting there was no slam dunk.
Beginning in the fall, bankers for the company, Trump Media & Technology Group, approached dozens of investors pitching the $1 billion deal, which offered them lucrative financial terms. By then, the start-up — intended partly as a conservative alternative to Twitter — had separately raised roughly $300 million through its planned merger with a special purpose acquisition company.
Those willing to put up at least $100 million, Trump Media’s bankers told potential investors, would get a call from Mr. Trump, said five people who were briefed about the pitches but were not authorized to speak publicly. Despite the opportunity to invest in a deal whose terms were structured to make a profit for investors, many of Wall Street’s big names passed.
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