John Santora doesn’t really change.
He’s been a Staten Islander for close to 70 years, married for 46, had the same home for 37. His mustache, before a pandemic shaving mishap, was in its third decade. (It’s since regrown.) He worked for the same firm for nearly half a century, starting as a buildings engineer and ending up an executive many times over.
But last summer, Santora did change — big time.
The company man of a bygone era left a 47-year career at Cushman & Wakefield to become CEO at WeWork, which had just gone through a transformation of its own.
The infamous coworking firm exited bankruptcy a year ago after a no-holds-barred restructuring: dozens of leases axed, a couple hundred tweaked and $4 billion in debt wiped clean.
Yet years after founder Adam Neumann was ousted, the erratic founder’s loss-making leadership still colored public perception. Neumann’s Hail Mary play to buy the company out of bankruptcy last year didn’t help.
But Santora, Neumann’s foil, could. Father to two, grandfather to three, Santora has a paternal authority and an aura of stability. He’s known industry-wide for his relationships.
Santora got the job after he called up WeWork’s new majority owner Anant Yardi, whom he’s known for 30 years, and asked how he could help.
Establishing WeWork 2.0 is about cost-conscious growth and partnerships — both in Santora’s wheelhouse. But it’s also about nailing the comeback tour. Santora, who “knows everyone in the industry,” according to his head of real estate Peter Greenspan, has the cred to do that.
And there’s a conceptual tie, too. He and WeWork — they’re not so different.
As the coworking firm enters its second act, Santora has just entered his third. The move has fostered a vigor that most 68 year olds would kill for, and the executive’s wisdom may be just what WeWork needs to grow up.
This interview has been condensed from two conversations and edited for clarity.
Born: March 15, 1957
Hometown: New Brighton, Staten Island
Lives: Tottenville, Staten Island
Family: Married to wife Debra for 46 years; Two children: John and Nancy; Three grandchildren
Yesterday was Easter. Did you celebrate?
Easter is a family day, so my son always does it. We had the grandchildren all together. They all had their little baskets running around.
You seem like a family guy, and also someone for whom community is really important. You grew up on Staten Island in the ’60s and early ’70s. Was that just how it was?
Yeah, it was very community oriented. Back in those days you left home in the morning to go play ball and you were out all day long and you’d come back home at 6 o’clock for dinner. You went to school and you played sports.
So you’re a sports fan.
I am absolutely a sports fan. A Yankee-Giant fan, as well as a golf fan — I do play golf now and go skate a little bit. Our touch tackle team was in the Staten Island Hall of Fame.
Say that again?
Yeah, I played touch tackle until I was about 35. Then I kind of had trouble getting out of bed in the morning. Laughs.
“When there’s uncertainty, it’s not good for anyone. But yes, there is this little upside where people begin to realize that you need that flexibility.”
Tell me about your family. I know they are heavily involved in the FDNY.
The fire department has always been close to my heart. I’m on the FDNY Foundation board, executive committee. My dad was a battalion chief, my brother was a captain, and that’s where I thought I was going.
But you went into real estate.
When I came out of school, New York City was on the verge of bankruptcy. They were not hiring cops or firemen. So I ended up taking a summer job at Cushman & Wakefield and just never left.
You married your wife, Debra, a little after you started at Cushman & Wakefield. How did you meet?
We met the only time in my life I ever went to a dance. We were 16 years old, and I went to a dance at her high school.
Newly married with a new job — Was that a period of your life where you felt: “I’m where I’m supposed to be”?
It evolved. For the first four years, I was in an engine room. That was kind of that union job, and then I was asked to step up into the main office and move into management. That’s where my career ultimately took off.
So you literally worked your way up from the ground floor.
Yeah, absolutely.
You have some distance from your career at Cushman now. Tell me some of the highlights.
Being part of the team that sold the World Trade Center. And then a low being six or seven weeks later and watching it come down. Being at the table the couple of times the company was sold in my career. Having had the opportunity to be the chief operating officer under a couple different CEOs.
Were any of those pinch-me moments?
Oh yeah. I remember being in Moscow after we acquired our alliance partner there and just kind of looking out over Red Square and saying, “What is this kid from Staten Island doing here?”
You were at retirement age, and you did the exact opposite of retire. Was moving to WeWork an existential decision?
It was an opportunity to do something different, yet still grounded in where I came from: take this company coming out of bankruptcy and lead it to profitability and long-term stability.
When WeWork had to cut all of those leases, the conversations with landlords were tough. Is there an aspect of your job that is re-establishing WeWork’s reputation?
A big part of what’s happened over the last 10 months is we’ve changed the narrative to what we are today — stable, disciplined, no debt, controlling expenses. Those are all important things for members, potential members and for the landlords, for the spaces we occupy.
Are the conversations difficult?
If the first time I’m meeting the person across the table is in a crisis, I’m already in a loss position. You have to have built trust and relationships to really get through it. Most times, if you’re walking in having known the person, you can figure out a solution. Sometimes they’re really tough, but landlords end up in the same position at times, right? How many landlords have sat across from lenders over the years and had those same challenges?
What was your biggest hesitancy about joining WeWork?
I had to understand — what was I walking into and personally, could I influence it?
So, I like your shirt.
Laughs.
This question goes along with that: I read in Time that one of the things you struggled with when you started here was how you dress. I love that you said that, because it’s so relatable. It’s just like starting at a new school. You want to fit in. Have you changed the way you dress?
I try. But I will tell you that I struggle in the morning. I’ll say: “All right — I’m wearing jeans today, and I’m wearing a sports jacket.” By the time I leave my closet, I’ve got dress pants on and a sports jacket and a collared shirt. It’s what I’m comfortable with.
I’ll note that you are not wearing a tie.
I’m not. But I have my suit jacket. Laughs.
Key strategies for WeWork now seem to be sustainable growth and de-risking. Is that accurate?
Sustainable growth without question, and balancing out the portfolio, balancing out that risk. We’ll continue to take some risk, which is doing leases. We have 120 or so management or revenue-share agreements, which have limited upside and limited downside, right? Most landlords are not going to put you in a position where you’re getting great space in a great building and you’re completely de-risked.
The recent deals with Amazon — are those leases? Revenue shares?
They’re lease agreements, but they are coterminous with our agreement with Amazon.
Is that type of repeat business with a big firm something you’re looking to do on a wider scale?
We are doing it with some others. And yes, we think it’s an important place where we will play in the real estate cycle. Corporate real estate executives are agreeing with us that a piece of their portfolio needs to be flexible.
You’ve said that WeWork will opportunistically expand. What does that mean?
The right building in the right markets we’ll take a new lease. We’re going to be disciplined in our growth, but we’re gonna have to grow.
Are there any markets you like?
The New York market’s solid, right? A little bumpy right now, but it’s solid certainly in the Class-A product. I’m seeing a bounce back in San Francisco without question.The Dallas markets are doing pretty well.
You said something interesting on LinkedIn recently. You said folks were calling you to ask how quickly they could pivot if the macroeconomic winds change, because we’re dealing with such uncertainty. Do you see economic instability as having potential upside for WeWork?
When there’s uncertainty, it’s not good for anyone. But yes, there is this little upside where people begin to realize that you need that flexibility. You get this pause for a year, or however long it’s going to be. But I still need real estate. Do I invest $50 or $100 million in building out this space? Or do I say, “Hold on, I’ll take some space for a short term ’til we ride this out and then decide if there’s an investment.”
Is that what you’re hearing, then? Pause?
Absolutely.
Have you shifted strategy since the tariffs came into play?
We’ve become more focused in talking to our clients about creating that flexibility — the short-term deals we can do for them.
Is WeWork profitable yet?
Last quarter of ’24 was a break-even from an EBITDA perspective and the first quarter of ’25 was positive from an EBITDA perspective. We’re not cash flow positive yet, because we’re continuing to invest in our spaces. This year we’ll invest between $80 and $100 million into our spaces. So our EBITDA has to get high enough to cover those investments to become cash flow positive. But that’s in our sights.
Is this the first time EBITDA has been positive?
It’s the first time in the firm’s history.
You, by your own admittance, don’t change much. How long do you plan on staying with WeWork?
So I joined, and it was kind of an open-ended agreement, and then just recently I signed a three-year agreement.
So fair to say you like it.
I like it.
Have you made any personal changes since you took the new role?
No. Laughs. Well — less time with the family. But we’re working through that.
I imagine that was a conversation with your wife.
I was winding down and working less, and the question was: Are we all in for this game? And, yeah, we’re all in.
What do you two do for fun?
We enjoy the theater. We enjoy each other’s time. We’ll go to dinner a lot. We’ll go with friends but during the week, we’ll catch a dinner or two by ourselves just to catch up. We enjoy our grandchildren, and we like to vacation.
Have you seen any good shows recently?
Last one we went to was “A Wonderful World: The Louis Armstrong Musical.” It was fabulous.
What’s the secret to a long-lasting marriage?
Communication — you got to talk things out. And I think spending time together and having the same goals. Debbie and I always had the same goals: You’re going to have a child, now you want to have a house, schools. And I think participating in a community helps.
I interviewed Larry Silverstein a couple years ago, and I asked him that question, and he said, “She’s always right.”
Ultimately, she is.
Looking back on your career, do you have any regrets?
Boy, would I have liked to have gone for my MBA and done that? Yeah, sure. I have a regret for not finishing that part of my education, but the education I got along the way was probably better anyway.
We’ve toed around this, but I’ll ask it succinctly: What makes a person who doesn’t change change?
It’s maturity and comfort in your zone. I can go do something different, and I know that I’m going to be successful at it.
One more on the question of change: How long have you had your mustache?
I had it from back then in my 20s. I took it off, I think around 30, and my son looked at me and cried because I didn’t look like his father. I grew it back right away. During Covid, I was shaving, and I kind of cut it and I had to take it off until it grew back.
Did you feel naked?
Yes!
