Some reports say he's been working 15 to 18 hours a day, rotating between each office to keep tabs on the two public companies he helped found.
Although Dorsey says it's manageable, skeptics question the viability of his unorthodox work schedule.
On Wednesday, we'll get a better look at how it's working out as Square reports its first-ever earnings as a public company.
Square's had a rough three-month period since going public in November 2015. Its share price dropped below its $9 IPO price at one point, and although it's recovered to trade at $11.48 as of Tuesday afternoon, that's still lower than the first-day closing price of $13.07 a share.
Analysts expect $343.2 million in revenue on a loss of $0.13 per share for the quarter. In the 3 months ended September 2015, Square reported $332.1 million in revenue, the company revealed in its IPO filing.
Dorsey has said that he's been able to set up a system that allows him to manage both companies well.
"I have set up a structure that is working very well for me, so that I can spend meaningful time at both companies, and I have enough flexibility in the schedule," Dorsey said during Twitter's earnings call last month.
But investors don't seem too happy about it. Twitter shares dropped as much as 13% in after hours, following an earnings report that showed lackluster user growth. Although the stock has somewhat recovered since then, it's still down more than half from its price from a year ago.
The dual-CEOship hasn't caused any major problems that we know of. But as Business Insider's Alexei Oreskovic previously reported, there were some decision delays at Twitter during Square's IPO process, and it exposed some of the high-level disagreements among executives about strategy and direction.
Square reports its earnings after the bell on Wednesday.
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