What do donkeys, dragons and Hawaii have in common? They all play a role in Elon Musk buying Twitter.

A new biography on Musk by Walter Isaacson sheds light on the billionaire’s state of mind during the bizarre lead-up to his bid for Twitter. The social media site wasn’t a natural fit for Musk’s portfolio of companies developing electric vehicle and space exploration technologies, but it harkened back to Musk’s longtime vision of building a social platform with payments incorporated. On a psychological level, it fulfilled his constant need to reach the next level in life, Isaacson wrote. 

In early 2022, things were going “surprisingly well for Musk,” according to Isaacson: The previous year made Tesla a trillion-dollar company and Musk had an extra $10 billion on hand from recent stock sales. Calm is unnerving for Musk, Isaacson wrote, noting that the billionaire would try to “manufacture a drama” at such moments. This time, using his extra cash, Musk began purchasing shares of Twitter, the social platform where he had posted 19,000 times over a decade. 

According to the book, after some of Twitter’s board members urged Musk to become more involved in the company, he secretly met with then-CEO Parag Agrawal at an Airbnb farmhouse surrounded by tractors and donkeys. Agrawal was nice—and that was a problem, according to Musk’s belief that managers should not be liked. “What Twitter needs is a fire-breathing dragon, and Parag is not that,” Musk said.

By then, Musk owned 9.2% of Twitter’s stock, worth $2.9 billion, and Agrawal invited him to join the board of directors. The billionaire had become increasingly concerned with the state of free speech in America, blaming what he called the “woke mind virus,” and he had ideas about a subscription system that would verify Twitter users. 

But existing board members wouldn’t take action on Musk’s ideas, and none of them even used the platform, according to Isaacson. It became clear to Musk that a board seat wouldn’t be enough. 

“I began to believe that Twitter was heading off a cliff and that I couldn’t save it by just being a board member,” Musk told the author. “So I thought, maybe I should just buy it, take it private, and fix it.” 

After stewing over the company’s problems from Ellison’s Hawaii estate—and posting criticisms of Twitter on Twitter—he made the decision to purchase the company, according to Isaacson. In texts with Agrawal and then-chairman Bret Taylor, he said “drastic action [was] needed,” and shared his plan. 

“It is better, in my opinion, to take Twitter private, restructure and return to the public markets once that is done,” he told Taylor. On April 13, he submitted the offer and tweeted the news after playing video game Elden Ring until 5:30 AM the next day. 

The series of events feels more like an episode of Succession than a business negotiation, but that’s not unusual for the richest man in the world. Musk largely runs his businesses as a series of risky bets, including staking Tesla profits on fully autonomous driving technology and launching a spacecraft for SpaceX that he knew would explode in the sky. After bidding for Twitter, he repeatedly changed his mind on the plan, according to Isaacson, trying to renegotiate a lower price and ultimately calling off the deal, which Taylor forced through after a court battle. 

It remains to be seen if the risks Musk took for X will pay off, as they have with his other companies, but the backstory behind the purchase helps explain his decisions over the last year. 

Since October 2022, when Musk became “Chief Twit,” the company has lost an estimated 90% of its value, Fortune reported. That has largely stemmed from an exodus of advertising dollars, resulting from advertisers’ caution around the new owner, a targeted boycott, and broader market conditions. His time at the helm of the company has been categorized by a series of playful, though strategically questionable, moves. Musk temporarily replaced the Twitter logo with the Dogecoin dog, brought beds into headquarters and set up a poop emoji auto-reply to emails from journalists. He renamed the company to X, wiping away some of Twitter’s brand value, and on a more serious note, brought in a seasoned advertising executive to serve as the company’s CEO. 

It’s possible Musk’s seemingly hurried decision to purchase the company means he was in over his head, at least at the start. But nearly one year into his reign, it’s difficult to attribute his unorthodox business choices to a lack of preparation. And it’s far from smooth sailing here on out. Looking to the future, Musk said he plans to sue the Anti-Defamation League over allegedly “trying to kill” X by accusing the platform and him of antisemitism. In the face of criticism and new competitors, Musk and CEO Linda Yaccarino must combat naysayers, woo more users, and guide the company to profitability. 

It will take five years to turn the company around, Musk predicted to Isaacson. One down. Four to go.