When John Santora became CEO of WeWork, the company was emerging from bankruptcy, saddled with one of the most notorious failures in business history. The longtime commercial real estate player is leading the company's next act: proving that flexible work can be a disciplined, profitable business.
As part of Business Insider's The Long Play, Santora shared what it takes to turn a damaged company into one built to last and offered insight into a real estate market being reshaped by how we work now.
He also talked about how AI is affecting real estate with Cadie Thompson, Business Insider's deputy news chief and executive editor.
BI's big event in NYC, which I had the honor of hosting, featured leaders from across the business spectrum. From AI infrastructure and healthcare to video games and publishing, we had it all covered.
You'd think such a wide-ranging group would be facing very different challenges. And on a granular level, they are. Carolyn Tisch Blodgett's daily efforts to gain support for Gotham FC are very different from John Santora's day-to-day work turning around WeWork.
But one big takeaway I had from the day — and something I heard repeatedly from people I spoke with at the event — is that the big-picture challenges are the same. And hearing how top leaders are navigating them was incredibly helpful.
Maybe that's growing your business in the face of some political surprises (Nubank cofounder Cristina Junqueira). Maybe it's pivoting a company to lean into the AI era (CEO of Allbirds-turned-Smartbird Nadia Carlsten). Or maybe it's just about taking the right steps to stay healthy in your daily life (Take-Two Interactive CEO and chairman Strauss Zelnick).
After all, we're all thinking about the long play.
The room was full of schmoozing and musing. Our reporter Henry Chandonnet networked with founders fine-tuning pitches, contemplating the future of work, and sharing laughs from their seats at The Long Play. From the hot takes to the aha moments and surprisingly (in Henry's words!) good food, see what it was like in the room.
From history-making supermodel to leading a brand empire. Ashley Graham's career spans from being the first-ever plus-size model on the cover of Sports Illustrated to building a business portfolio. She shared why raising money for her alcohol brand was "very, very hard and humbling." You can watch her discuss vision boarding and how rejection has made her better in business with BI's Leena Rao.
The guy behind one of gaming's most anticipated releases has some health advice. Strauss Zelnick leads the company behind Grand Theft Auto, but he keeps some simple, healthy habits. He shared the eight he lives by and why peptides aren't one of them. And much like his health regimen, Zelnick prefers a clear-cut management style, prioritizing direct CEO access and avoiding "toxic" discretionary pay programs.
Entrepreneurship comes with risk and uncertainty. As one founder put it, "You have to be insane."
Two successful founders share the mindsets that helped them push through when failure felt possible.
They explain how anyone can develop the resilience and confidence to take entrepreneurial risks.
A traditional job typically comes with a regular paycheck and benefits — a measure of stability and predictability.
Entrepreneurship offers neither. It comes with risk and uncertainty. There is potential for a big payoff, but no guarantees.
Popsmith CEO Tal Moore put it bluntly: "You have to be insane to be an entrepreneur," he told Business Insider. "Because there's so much risk. There's so much turbulence."
"I ended up selling $600,000 worth of my personal stock to keep us afloat," Moore said.
It was stressful, of course, but Moore felt he had to find a way through — not only because he had invested heavily in Popsmith, but because friends and family had, too.
"They bet on me. They bet on my brand," he said. "If you lose your own money, that's one thing. But there was just no f---ing way that I was going to lose my friends' and family's money."
Kyle Ray had a different source of motivation. In high school, one of his teachers told him he'd end up working at McDonald's.
Rather than feeling discouraged, Ray used the comment as fuel.
Ray said he had doubts "all the time" that the business would work, but wanting to disprove that teacher meant adopting a failure-is-not-an-option mindset.
"I'm going to make this work," he decided. "I'm just going to figure it out."
Throwing "Hail Marys"
When Moore and his business partner had just two weeks of cash runway left, saving the business meant getting attention and moving product without spending much money.
"At this point, I had to throw some Hail Marys," Moore said.
His first idea, which he called "harebrained," was to send poppers directly to the CEOs of Williams-Sonoma and Crate & Barrel. He'd designed the product with those retailers in mind, but couldn't get their attention.
"I know my popper will sell on their shelves," he thought. "I just have to get it in their hands."
Tal Moore is the cofounder of Popsmith.
Jason LeCras for BI
Moore bought the most upscale, high-quality paper he could find at Kinko's, handwrote notes to both CEOs, and "blind-shipped" poppers to them. Within two months, buying teams from both companies had reached out, he said.
Then came Oprah.
Moore had no idea how to get on Oprah's annual "Favorite Things" list — "it's just like a total black box," he said — until he spotted an opening on LinkedIn. A junior editor at Oprah Daily had posted about popcorn, so Moore sent her a cold message. She replied, requested a popper, and eventually helped get the product in front of Oprah.
An Oprah Daily editor told Moore that the team considers about 15,000 products each year before Oprah makes her final selections. In 2024, Popsmith made the cut.
After the list was announced, the company sold out of every popper within weeks. Popsmith went on to sell out three more times over the next five months.
As an entrepreneur, "there's a pressure and a will to win," Moore said. "There's an endless drive that just never goes away. I wake up hungry, and I will not stop."
Developing the entrepreneur mindset
Like Moore, Ray has a refusal-to-quit mentality. He views entrepreneurship as a highway without an off-ramp — no Plan B waiting at the next exit.
"If there is no exit, then there's just one path," he said. "And you just have to get through it."
That doesn't mean every business will succeed. In fact, many won't. But Ray believes entrepreneurs need to be willing to take risks, potentially look foolish, fail, and move on to the next idea if necessary.
Often, he said, fear of failure — and other people's judgment — is the real obstacle.
At the core of his mindset is a willingness to care less about both.
Kyle Ray is the founder of Geek Window Cleaning.
Courtesy of Kyle Ray
"If Geek fails now, I'm going to look stupid, but it's like, 'Okay, cool. What's next?' Like, I don't care," he said. "And the earlier you can develop that carelessness — the 'I don't care if I look stupid' or 'I can fall flat on my face. I am still going to go for it' — I think if you get to that point, anybody can go out and be an entrepreneur."
That mindset can be learned, he said. Like any other skill, from swinging a tennis racket to ballroom dancing, it takes time, consistent work, and patience. Ray recommends three steps:
1. Start with books. They're cheap — or free at the library. Ray's top picks include "Inner Excellence" and "Can't Hurt Me." Moore prefers biographies of entrepreneurs and business leaders, from Warren Buffett and Richard Branson to John D. Rockefeller.
2. Find someone who is already doing what you want to do at a high level. Then ask questions, Ray said: "What are you doing that I'm not? What am I doing that's preventing me from breaking through?"
3. Join a mastermind or hire a coach. Ray has multiple.
"When there's something I don't know, or I need to learn, I start to look for coaches," he said. "It's like a wormhole, right? If you can find somebody that knows something about where you want to be, they can help you collapse time and just jump forward to that spot."
Taylor Kelly started Eventful ATL as a side hustle and turned it into a full-time small business after being laid off from his corporate job.
SHLK Family Production
Taylor Kelly started running candle-making workshops in 2023 to get out of the house and meet people.
He turned his side hustle into a full-time small business after he was laid off from his corporate job.
His company offers classes like flower arranging, pasta making, and tea tasting and blending.
This as-told-to essay is based on a conversation with Taylor Kelly, the 34-year-old founder of Eventful ATL, who lives in Atlanta. The following has been edited for length and clarity.
If you'd asked me in the beginning if my side hustle of candle-making classes would become a business a year later, I would've had no clue.
It went from $2,000 in revenue in 2023, when it was an evening and weekend side gig, to $16,000 in 2024, when I created a legal business entity: Eventful ATL.
Then, in 2025, I was laid off from my corporate job.
It gave me more flexibility to really dive in, and we ended the year a little under $75,000 in revenue. I pushed into 2026 with a stable small business, and we're on track to end 2026 with around $100,000 in revenue.
We currently offer over 12 class topics, including candle making, flower arranging, pasta making, tea tasting and blending, charcuterie making, wine tasting, and cocktail making. We also recently added pottery-making and seasonal classes like wreath-making and gift-wrapping.
Eventful ATL hosts classes such as pasta making.
Antonio Riles
Sometimes I wonder, how the heck did I end up here?
I started hosting candle-making workshops after moving to Atlanta
I lived in New York for several years and worked for Ritani, a New York-based jewelry company, in a few different marketing roles from 2019 to 2025. I took two years off from Ritani between 2020 and 2022 to do a full-time MBA program at the University of Miami, and I rejoined the company in May 2022.
My side gig began in the winter of 2023. I'd moved to Atlanta, and in order to get out of the house and meet people, I started hosting candle-making workshops on evenings and weekends. Candle making had been my hobby during COVID and grad school.
It started to grow beyond candle making, into other types of classes. I teamed up with a venue partner who has a wonderful event space and added flower-arranging and caviar-tasting workshops.
A caviar-tasting workshop.
SHLK Family Production
Initially, I asked people whom I knew had specific hobbies, passions, or experience if they'd offer a class in it. Soon, I started getting emails and calls from small business owners and creatives who really wanted to teach but didn't want to deal with the logistics of coordinating classes or experiences.
It wasn't hard to balance it with my full-time job because I was working remotely and wasn't doing anything else after work hours. I'd spend my nights and weekends working on Eventful and focused on SEO for organic growth.
As the months went by, it became clear that there was an opportunity to keep growing Eventful, and I thought about the possibility of making it my full-time job. However, I liked having a stable paycheck.
I was laid off from my full-time job in May 2025
It wasn't a big surprise that it happened. I remember being stressed, like, Oh, crap, I don't have any income now. If I hadn't had this little business on the side, I would've spiraled. I'm so grateful that I had my side hustle to fall back on.
I started my job search in June while still working my side gig, but I wasn't getting much traction with interviews. I sent out hundreds of applications and got only a handful of interviews. I'd be so annoyed about spending a whole day applying when I could've spent that energy diving into my business.
There were so many jobs listed, and a recruiter would say, "We'd love to chat," and then the role would vanish. That was disheartening, and it made more sense to pursue something that I had going myself.
I also wasn't finding roles that were exciting to me, the way I had years ago when I lived in New York. Part of that was because I was so excited about working on my business. I knew there was potential; it wasn't huge at the time, but I knew we could continue to grow.
A couple of months later, I made the decision to pursue my business full-time
I'm not sure I would've pursued growing the company full-time anytime soon if it weren't for being laid off.
Now, we host 15 to 20 events a month. We have at least two public classes each week, and we're adding more throughout the holiday season, as well as multiple private group experiences throughout the week.
We have a lot of brands that leverage us to provide team-building experiences for clients and employees, including companies like Google, Salesforce, Chick-fil-A, and Home Depot.
We work with about eight to 10 contractors and instructors who teach classes. I like working on a team — I don't like sitting here alone. I've also started teaching a lot of our pasta-making and flower-arranging classes.
Kelly works with around eight to 10 contractors and instructors.
SHLK Family Production
When I'm not instructing, I like being present at as many classes as possible to facilitate setup and breakdown. However, there've been many times when our team has handled classes without me present, and the goal is to ensure we're creating the right systems to make that the standard, in order to eventually scale and grow into new markets like Miami and New York.
Sometimes I'm the marketing person, and sometimes I'm the instructor for the day. Every day is a new day, and I wake up to an email of something cool that I didn't expect coming across my desk.
I'm excited for us to continue to grow
It took until September of this year, when my brain was like, This is it. This business is really bringing in money, and if I'm being lazy or not doing as much as I can, it impacts my life. I have a dog who's very expensive. I either make money and pay the bills right now, or it doesn't happen.
It's not just about the money, though. I also get to speak with so many passionate people every day. My business has been able to film on a Bravo show and has been featured in local news. We signed a lease for our first permanent space in downtown Atlanta early this year, in preparation for the World Cup this past summer.
Eventful ATL has been featured on local news and Bravo.
Courtesy of Taylor Kelly/Eventful ATL
Now that I've fully committed and we have people who are really invested in what we're doing — the business owners who love teaching and sharing these opportunities — I always think about scalability.
There are a lot of different moving parts right now. I'd really love to focus on brand partnerships and do a big partnership push in 2027.
That being said, who knows what I'd do if another opportunity came up? I don't have to always be there personally with my business.
We have a lot of events happening at the end of 2026, which is giving me anxiety — but I asked for it. It's either that, or we don't grow.
I spent my Thursday at The Long Play, where attendees made new connections and debated the future of work.
Henry Chandonnet/Business Insider
I schmoozed with CEOs, founders, and investors at Business Insider's The Long Play in New York.
Attendees heard from speakers ranging from Barry Diller to Ashley Graham — and spent a whole lot of time networking.
Some attendees tried pitching deals. Others debated the future of work.
The New York venue was bustling with executives, some of whom governed companies with thousands of employees.
I met my first one within seconds of walking in.
On Thursday, I attended Business Insider's The Long Play event at Perelman Performing Arts Center. (Full disclosure: Business Insider is my employer, and you're probably reading this on its website.) I entered the event with a mission: to chat, network, and maybe learn a thing or two about my own career.
Workplace debates and startup chatter filled the air at Business Insider's The Long Play.
Carl Timpone/BFA
Mingling among the crowd, I chatted with the founders of AI startups and communications chiefs. They debated remote work, asked about management styles, and discussed working together. "I've got to work on my elevator pitch," one CEO told me.
I sat down for lunch with some attendees to discuss a question: Is workplace loyalty dead? Most said no, or that it was more complicated. One brave soul, the content creator Colin Rocker, said yes.
"I still think it's dead," he told me after the lunch chat. "But, I will say, I got more context that it's not necessarily working across the org chart."
He added: "That hurts managers, too."
Fancy napkins!
Carl Timpone/BFA
Others at our table traded mentorship techniques and thoughts on leading an office. Nitzan Shapira said that, while working at Intel and Cisco, meetings were crucial. He has more flexibility while leading his AI startup, Harmony. "I'm kind of allergic to meetings," he said.
Munching on my plate of salmon, salad, and a caprese sandwich, I continued to chat with the crowd. Then came the dimming of the lights and the voice on the loudspeaker. The interviews were about to begin.
A who's who of the audience
Ashley Graham at Business Insider's The Long Play.
Carl Timpone/BFA
You can tell a lot about the crowd from when people raise their hand — and when they don't.
I learned, for example, that much of the crowd had played "Grand Theft Auto." What better way to blow off some steam after a career-building conference than with some virtual vice? The attendees didn't consider themselves avid gamers, though; only a few hands shot up when Take-Two CEO Strauss Zelnick asked.
There were also a handful of investors in the crowd. Supermodel Ashley Graham asked for a show of hands, and I spotted three. During one of the breaks between talks, I talked shop with yet another venture capitalist.
As for GLP-1s, the crowd was less eager. Senior correspondent Melia Robinson asked while interviewing Ro CEO Zach Reitano, and she got only a few raised hands. (I bet, if we swapped the public hand-raising for a blind survey, that number would go up.)
The crowd at Business Insider's The Long Play.
Carl Timpone/BFA
The attendees around me were rapt. My seatmate, who worked for an AI startup, took notes with pen and paper. I saw some others jotting down learnings in the Notes app on their phones.
WeWork CEO John Santora described upping the once-freewheeling company's dress code. When he got there, Santora spotted pajamas and shorts; he now spots some salespeople in sport coats.
It prompted me to look around and check out what the audience was wearing. There were lots of blazers, button-ups, and slacks. A handful went more casual with their denim jackets and colorful blouses.
Take-Two Interactive CEO and chairman Strauss Zelnick and Business Insider senior correspondent Sarah E. Needleman at The Long Play.
Carl Timpone/BFA
There were belly laughs, like when my talented colleague Sarah Needleman flubbed "how do you define success" with "how do you define sex" while interviewing Zelnick. He chuckled; the crowd joined in, and it bonded the audience.
And there were sobering moments, like when Noa Argamani described her drive to fund Israeli startups after spending 246 days in Hamas captivity.
The list goes on: There were chats with media mogul Barry Diller, banking entrepreneur Cristina Junqueira, and Nadia Carlsten, the CEO of the sneaker-company-turned-AI-infrastructure-provider Smartbird.
The bar at The Long Play.
Carl Timpone/BFA
The event was really about meeting other people, though, and being inspired. I endlessly looped around the room, talking to C-suiters at startups and public relations agents. You could always hear the hum of new connections coming from the back of the room.
It ended with glasses of wine and hors d'oeuvres. After biting into a surprisingly delicious slider — Graham talked about pairing her wine with Korean barbecue and lasagna, and it made me hungry! — I had officially reached my schmoozing limit.
Drinks are served!
Carl Timpone/BFA
I ended the day with a full heart and a handful of new phone numbers. If you gave me yours, expect a text soon with plans to get coffee.
Talent and senior leaders surveyed think linear career paths will become less common.
jean-marc payet/Getty Images
A Korn Ferry report said "workers will zigzag more than they climb" the career ladder next year.
This fluid career lattice has its positives, such as skill expansion.
However, there are also benefits to the traditional linear path, such as raises and a clear goal.
Instead of going straight from junior to senior to manager to executive, you might find yourself bouncing between managerial gigs for different departments or taking a step back to focus on individual contributor work.
Organizational consulting firm Korn Ferry finds, based on a global survey of over 1,300 talent and senior leaders, that while traditional linear career ladders of moving up into higher-paying and more prestigious job titles within a particular specialized profession still exist, fluid career paths that end up looking like a lattice are becoming more important.
Career lattices may mean moving to a different team instead of being promoted, taking on a new role within the company to expand your skills, or moving down the career ladder. There can be all kinds of movements someone can take in the career lattice format.
Sixty-four percent of surveyed leaders said linear career paths will be less common, and 85% said progression will depend on skills and capabilities, rather than tenure or job title. Most said employees will be taking on greater ownership of their career development.
"In 2027, workers will zigzag more than they climb, landing in places no succession plan accounted for," the report said. "It will take a broader range of skills to rise through the ranks, so people will be searching for ways to learn them."
To learn whatever skills they need to before moving up, the report said people might be willing to move to a different team or position so they can develop their skill set. The report noted adaptability is the most sought-after skill among employers. AI fluency could be another attractive skill as the tech becomes more prevalent in the workplace.
A blog post from the workforce solutions provider Careerminds, by career and business coach Cynthia Orduña, listed examples of lateral moves. A sales representative could move to a customer success manager role because "strong relationship-building skills help improve customer retention and account growth." An IT support analyst could become a cybersecurity analyst because they can expand their technical knowledge.
Cathleen Beetel, senior client partnerat Korn Ferry, thinks both employers and employees should embrace lateral transitions because they allow employers to tap into existing talent they have vetted and know works well for their company.
A guide from job-search platform Indeed said career lattices encourage workers to try new opportunities, learn what they're best at, acquire new skills, and understand more about company operations. Indeed said another bonus of career lattices is that it gives workers more control over their careers.
"You have to not see a lateral move or a sideways move as stagnant," Beetel said. "It could potentially be the fastest route forward for an employee because they can gain those skills that are perhaps adjacent to what they have today that actually puts them in a better position for a promotion in the future."
Career ladders have their own benefits, beyond thinking about the likely pay increase that comes with a title bump. Indeed said that having a well-defined ladder can raise employee motivation, encourage deep expertise in a specific area, and be an incentive to work toward a clear goal.
The Careerminds blog post said workers might decline lateral moves if they think it isn't beneficial to them — such as not bringing a raise, concerns about what this means for career progression, and concerns about leaving their well-established team.
So there are trade-offs in employers offering lateral moves over a step up. It's the company's responsibility to communicate why someone is being offered this move and why it could be beneficial.
"Employees are more likely to accept a move when they understand why they were selected, what they'll gain, and how the opportunity supports their long-term career growth," Orduña wrote. "Instead of focusing on the business need alone, communicate the value that the lateral move in career creates for the employee."
Alex Rodriguez says baseball taught him to be resilient.
Todd Owyoung/NBC via Getty Images
Alex Rodriguez says baseball gave him a "Ph.D. in failing."
He says the teams that win aren't always the ones with the biggest or most talented stars.
He now brings that same resilience to running his investment firm.
Alex Rodriguez says baseball taught him the value of failure.
Speaking on Friday's episode of "The Sebastian Maniscalco Show," Rodriguez said his professional baseball career shaped his approach to managing his business, A-Rod Corp.
"I think the greatest thing that I've learned from sports is to develop thick skin, because baseball specifically is a major sport of failure," Rodriguez said.
The former baseball player said he ranks fifth all-time in strikeouts in the history of the game.
"That means only four people in the history of mankind have failed more than me, right?" Rodriguez said. "I often tell my girls I have a Ph.D. in failing, but I also have a master's in getting back up."
He said the key is to keep coming back and trying again. No matter how many missed hits or strikeouts came before, each new at-bat is a fresh chance, he said.
"That's a real gift, and I think that this generation of young kids lacks that a little bit," Rodriguez said.
He also said success requires a strong work ethic, a team with complementary skills, and the ability to work together toward a shared goal.
Rodriguez then referenced a quote that resonated with him. "Great players often don't win championships. The best teams do, even though they may not have the most talent," he said.
"I'm a big believer in that," he added.
Rodriguez is not alone in seeing setbacks as part of the path to success.
"When you lose a deal or you didn't manage to close the deal, then you dive into it — where did it go wrong?" Burkhardt said. "Failure is something you should embrace when you play sports or when you're building a business to get better."
Conan O'Brien has similarly said that his long career has depended on treating setbacks as a way to reset and look ahead.
"It keeps happening over and over and over again, and then it's just learning to roll with it and say, OK, what's my next opportunity? Reset, recommit, and look for the next opportunity," O'Brien said in a March podcast appearance.
Login
