The vision of a leader drinking cocktails on a tropical island resurfaced after Musk became Twitter's biggest shareholder in the spring of 2022. In text messages to his friend, the podcaster and angel investor Jason Calacanis, Musk said Twitter's newly appointed CEO Parag Agrawal was on a 10-day vacation in Hawaii. At the time, Musk had been toying with the idea of joining Twitter's board of directors, but was growing increasingly frustrated with Agrawal. He doubted the two could work together.