For WeWork’s CEO, Fridays are for sneakers. Sometimes.
At Business Insider’s The Long Play event on Thursday, John Santora told Deputy News Chief Cadie Thompson that he rebuilt WeWork in part by establishing a sense of trust and decorum among employees.
In pursuit of that goal, Santora instituted a dress code for employees, but also gave them one day a week to work from home.
“I didn’t have the ability to go watch my son play a 3 o’clock baseball game,” Santora said, adding, “We have to give our employees that flexibility to do all that.”
Santora, formerly the chief operating officer at Cushman & Wakefield, a real estate firm, became WeWork’s CEO in 2024 as the once-buzzy office startup emerged from a disastrous Chapter 11 bankruptcy filing.
Santora had a short time to decide whether to join the faltering company, he recalled. And it wasn’t exactly an easy choice.
“I was kind of at that point of, ‘Should I retire?'” he said. “My daughter Nancy said, ‘Dad, you know we love you, but when you have too much time on your hands, you’re a pain in the ass.'”
Since those deeply red days in 2019 when WeWork’s valuation plummeted from $47 billion to roughly $8 billion before it was bailed out, the company has stabilized. It posted eight quarters of EBITDA profitability and expects a fourth straight quarter of cash-flow profitability.
In 2025, it reported about $2.3 billion in revenue.
Though it hasn’t hit the valuation it once had, the fact that the company could be revived at all is remarkable. WeWork, founded in 2010, rents out office space, spruces it up, and parcels it out to freelancers, startups, and other businesses.
Its first CEO and founder, Adam Neumann, made bold pronouncements that WeWork would “change the world” and “elevate the world’s consciousness” by renting out office space to startups.
But after a bungled IPO, it became clear to the new stakeholders that a different type of leader was sorely needed.
As it turned out, Santora was that leader.
Having worked for 47 years at Cushman & Wakefield, Santora had the real estate experience that Neumann lacked, albeit without the magnetism of a Silicon Valley whiz kid.
“From a leadership standpoint, I’m a very structured, disciplined person,” he said. “I’m a suit and tie, buttoned-up real estate person.”
Santora recalled an early trip to one of the offices, where he discovered employees wearing jeans, pajamas, slippers, and shorts.
“I grabbed my head of HR,” he said. “See that? I don’t want to see it anymore.”
Santora, who at one point described himself as an “old chubby guy from Staten Island,” didn’t just force employees to wear sports coats to important meetings. In his words, there was some “give and take.”
“I don’t look at what time they leave, what time they come in,” he said of his employees. “As long as they’re getting their work done and they’re keeping their clients happy.”
And Santora allows himself one exception to his suit-and-tie persona.
“Fridays, I’ll actually sometimes wear sneakers, depending on what my schedule is,” he said.
