Dorsey has been as much a beneficiary as anyone. His stake in Square has jumped by $668 million this month, and his Twitter shares have appreciated by $65 million.
As May comes to an end, Square is worth $23.6 billion, not far behind Twitter’s $26 billion stock market value. After years of skepticism, Wall Street has apparently come around to the idea of the 41-year-old Dorsey running two publicly traded companies at the same time.
When Dorsey returned to Twitter from Dick Costolo in 2015, it was supposed to be temporary. At the time, Dorsey had his hands full with Square, which was preparing for its stock market debut.
Twitter’s board couldn’t agree on anyone else, so Dorsey was given the full-time gig at Twitter just a month before Square’s IPO. Analysts were relieved to see the process come to an end, but had plenty of concerns.
“As a product guy, Dorsey is a good fit, although we thought an outsider was the best option,” wrote Evan Wilson of Pacific Crest Securities. Analysts at JMP Securities wrote that, “While it remains to be seen how well new CEO Dorsey can manage both Twitter and Square, we believe he will be most focused on Twitter’s product and making it easy to use.”
Investors who stuck with Dorsey have made a bunch of money, particularly in the past year. Twitter shares have climbed 88 percent over the last 12 months, outperforming all of the most valuable tech companies. Over that same stretch, Square is up 154 percent.