On a busy day, Jack Dorsey has about 360 minutes to himself.
That's just six hours to unwind or -- you know, sleep -- before the next day starts. Then, once again, he ping-pongs between the neighboring offices of Twitter, the social network he co-founded nine years ago, and Square, his mobile payments startup. He is the chief executive of both companies, having stepped into the role at Twitter in October.
Running two companies is hard. Running two publicly traded companies is harder, especially when investors clamor over underperforming stock. Running two unprofitable, publicly traded companies at critical turning points in their strategies is probably the hardest.
If his dual tenures prove successful, he may earn a place in a small group of celebrity chief executives able to run two companies at once. Steve Jobs did it during his years as the boss of Pixar and Apple. Elon Musk is doing it at his electric carmaker Tesla Motors and SpaceX, his private rocket company.
Jobs could barely handle the stress. The jury's still out on Musk. And based on how little time Dorsey gets to rest, it's unclear how this will pan out for him.
A report published Monday in The Wall Street Journal gave a glimpse into how the 39-year-old Dorsey pulls it off:
Mr. Dorsey is disciplined about his schedule and habits. For example, current and former Twitter employees say he is known to abruptly get up at the designated end time of a meeting, simply saying, “I’ve got to go.”
He typically starts his days with coffee at Blue Bottle, located between the two headquarters. According to Twitter and Square, on Monday morning, Mr. Dorsey arrives at Twitter for five-hour meetings with his eight senior executives and Mr. Kordestani to review the business operations and projects. At 1:30 p.m., he rushes over to Square to repeat the same exercise. Mr. Dorsey tells executives to put their phones and laptops away—he has no office or desk at either company.
Neither Twitter nor Square immediately responded to requests for comment.
Dorsey's biggest threat when working 18-hour days may be sleep deprivation. A person his age should get between 7 and 9 hours, according to the National Sleep Foundation. Even if he slept the full six hours he has to himself, he'd still be an hour under the minimum amount of recommended rest.
Sleep deprivation slows down your decision-making process, per a study released in May by Washington State University. Lack of sleep also causes memory loss and can make your angry and unable to regulate your emotions. All that makes steering two companies through choppy water a lot more challenging.
Dorsey seems to be pulling it off, for now. He has yet to choose a deputy at either company, but he seems to be delegating to the execs who report directly to him and checks in frequently, according to WSJ.
"To make something like this work, you have to have a world-class team around you," Sydney Finkelstein, management professor at Dartmouth College’s Tuck Center for Leadership, told The Huffington Post in October. "Effective leaders delegate. In this case, you probably have to delegate more than normal. … You have to be able to process in your brain two different worlds."
Dorsey has long prioritized personal wellness. He may not have as much time for his long, relaxing walks along the coastline. But he is known to meditate and run, which help focus the mind. “When he comes into the room you get this sense of comfort that you’re with a very grounded person,” Twitter Chairman Omid Kordestani, Dorsey's boss, told WSJ.
Dorsey isn't the first to attempt such a schedule. To run both Tesla and SpaceX, Elon Musk works up to 100 hours per week and wishes he could forego food for productivity. At a conference in October, Musk said he wouldn't recommend running two companies because "it really decreases your freedom a lot.”
But Dorsey may be more consciously emulating the late Steve Jobs. His career, in many ways, mirrors Jobs' path. They were both booted from the companies they founded, then returned as chief executives. Now, like Jobs, Dorsey works 90 hours per week, meditates to get through it and even adopts eccentric styles that aesthetically set him apart from other chief executives.
If the comparison to Jobs holds true, though, it's worth noting the toll it took on the tech titan.
Mashable's Seth Fiegerman notes that in a passage from Walter Isaacson's 2011 biography of the Apple co-founder, Jobs recalled the years spent running two firms as "the worst time in my life."
I had a young family. I had Pixar. I would go to work at 7 a.m. and I'd get back at 9 at night, and the kids would be in bed. And I couldn't speak. I literally couldn't, I was so exhausted. I couldn't speak to [his wife] Laurene. All I could do was watch a half hour of TV and vegetate. It got close to killing me. I was driving up to Pixar and down to Apple in a black Porsche convertible, and I started to get kidney stones. I would rush to the hospital and the hospital would give me a shot of Demerol in the butt and eventually I would pass it.
"One to two percent of the population can survive on four hours of sleep a night," Dr. Tara Swart, a neuroscientist, told CNN. "But 7-8 hours is optimal for most of us."
Hopefully, once Dorsey names a No. 2 at each company, he can find some more time to rest.