• Brian O’Kelley banked less than $100 million after selling his $1.6 billion startup AppNexus to AT&T—and gave the rest to charity. The Gen X CEO says billionaires with yachts and multiple mansions are “obnoxious,” and that keeping a cap on his wealth keeps him grounded, accountable, and connected to reality. “I don’t get why you need $200 billion, $500 billion, or even $1 billion,” O’Kelley exclusively tells Fortune. 

What would you do if you became an overnight multimillionaire? That’s exactly what happened to Brian O’Kelley in 2018, when he sold his ad-tech company, AppNexus, to AT&T for $1.6 billion.

But instead of buying a yacht or a fleet of sports cars, O’Kelley sat down with his wife for what he calls a “really interesting conversation” about how much was enough—and everything else went to causes they care about. 

“I don’t believe in billionaires. I think it’s just ridiculous,” the serial entrepreneur exclusively told Fortune, adding that he kept less than $100 million from his 10% stake in the startup after it was acquired.

“We just figured out a number that we thought was enough money—to be able to buy a house and things like that—and then we doubled it, and we gave the rest away.”

The 48-year-old is now building his third startup, a supply-chain emissions data company called Scope3. Still, he claims you’ll never catch him joining the billionaires club. “I will never be that wealthy. Even if Scope3 is immensely successful, we will give that money away.” 

Why the self-made millionaire refuses to cross the billion-dollar line

For O’Kelley, the decision to cap his wealth isn’t just about generosity. “We never wanted to have so much money we didn’t have to make choices. It’s meant that we can’t be completely ridiculous about our life,” the Gen X CEO said. “We have an amazing life, we can do almost everything we want. But we can’t quite do anything we want—we have to talk about our budget like anybody else does.”

“I don’t get why you need $200 billion, $500 billion, or even $1 billion. The joy of appreciating what we have and making those hard choices is really foundation.”

Part of Brian O’Kelley’s philosophy comes down to not wanting his kids to become spoiled. “I feel terrible because they get to fly business,” he says, adding that at 6-foot-5, he does it for the comfort, but is uneasy about his children becoming accustomed to a life of luxury.

“I’ve flown all around the world in coach so many times, this is me spoiling myself, but I don’t want to spoil my kids,” O’Kelley adds. “And a lot of this comes back to me thinking about how life looks from their eyes. I want them to have a bit of that struggle that I had.” 

He says amassing billions—and flaunting it—only keeps leaders further removed from reality.

Billionaires with helicopters, superyachts and islands to their name are ‘obnoxious’

A record-breaking 3,028 people are now billionaires. Together, they hold more wealth than every country in the world except the U.S. and China—and the number of people to join that list keeps growing at a record pace as experts predict AI could welcome in an era of trillionaires. 

And they’re no longer being “stealth” about their wealth. At the start of the year, tech titans and CEOs (with a combined wealth of over $1 trillion) gathered for Donald Trump’s inauguration, dripping in diamonds and designer gear. Most recently, Jeff Bezos’ $46 million wedding to Lauren Sanchez in Venice was a lavish display of excess, complete with private jets, super yachts, and an estimated 745 carats’ worth of jewellery.

“I wish more folks would ask the question of, why do I want the lifestyle that Jeff Bezos has?” O’Kelley says. “You can’t have a yacht and a helicopter and an island, and a big building with your name on it and all these things, because then you’re just sort of obnoxious. No human can actually truly appreciate that.” 

O’Kelley’s says billionaires represent “such an incredibly ludicrous waste of money in a world where there’s so many people who don’t have that,” but he says actually being one is also “othering”—separating you from the limits and consequences that define normal life.

“There’s something about keeping connected to normalcy that is really, really important,” the entrepreneur explains. “I don’t want a yacht and I don’t ever want to be able to be without consequences. I think that’s the biggest risk, is, how can we be accountable when we have so much money we can buy anything?”

“Look, there’s days where I am like, ‘man, I wish I had some money,’ because my company could use an infusion of cash. That would be great if I didn’t have to ask VCs. But you know what that is? That’s accountability.”

This story was originally featured on Fortune.com

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Research confirmed what many workers had already suspected: Return-to-office mandates were often a thinly veiled headcount reduction. 

But while forcing workers to choose whether they love remote working more than being employed, a survey shows bosses aren’t following their own mandates. 

In fact, 93% of CEOs say they don’t go into the office full-time and have instead adopted flexible working patterns.

International Workplace Group’s survey of more than 500 U.K. chief executives reveals bosses are notably absent from the workplace. Meanwhile, more than half of Fortune 100 desk workers have workplaces with fully in-office policies, according to new data from real estate company Jones Lang LaSalle Inc.

Although working from home makes employment more feasible for parents, pet owners, workers with disabilities, and those who can’t afford to live near the office, bosses have been calling staff back to their desks, often in the name of creativity and collaboration. Yet only 7% of CEOs go into the office five days a week, according to IWG.

In comparison, data from the ONS reveals that 64% of those with a salary below £30,000 ($38,000) are expected to be in the workplace full-time.

Perhaps unsurprisingly, workers who have been stung by RTO mandates will likely be left reeling by the double standards of the findings—and CEOs know it. 

The research found two-thirds of respondents know they would lose talented people if they insisted on their employees being present in a central office every day, as nine in 10 work flexibly themselves. 

CEOs who don’t go to the office

Despite being notably absent from the workplace themselves, bosses have spent the best part of three years cracking down on office attendance. 

Last year, Dell gave its workers literal red flags for not swiping their badge enough. Amazon put an end to “coffee badging” by setting a minimum-hour obligation on in-office days.

Other businesses went one step further and explicitly told their workforce to commute into the office or find somewhere else to work. Patagonia gave some 90 staff members just three days to decide whether they would relocate close to the office or quit their jobs. 

Likewise, the gaming giant Roblox warned workers who can’t make it to the company’s physical office that they would have to find another job—as did the bosses at TikTok and Walmart. 

Then there’s Amazon’s CEO Andy Jassy, who warned workers that if they can’t commit to the company’s mandate, then “it’s probably not going to work out for you.”

CEOs want to avoid commuting, but so do employees

Why don’t CEOs want to work more from the office? For the same reason as most: IWG’s research shows they want to avoid a long commute. 

In reality, with inflation high but wages low, so too do unemployed Gen Z grads who are having to turn down job opportunities because they can’t afford the commute.

However, it’s those at the bottom end of the pay scale—who are most impacted by the costs associated with RTO mandates—who are also most likely to be asked to commute to the office, ONS data shows.

While just 20% of businesses’ top-earners earning over £50,000 ($64,000) are expected to be in the office, this jumps to 64% for those with a salary below £30,000 ($38,000).

A version of this story originally published on Fortune.com on July 29, 2024

More on return-to-office:

• Employees are engaging in revenge RTO, but these small acts of defiance are the symptom of a bigger problem
• Forget about RTO—companies are getting distracted with mandates and screwing up these 5 core work practices
• More than 60% of workers have considered changing jobs due to rigid RTO policies and would take a pay cut for better flexible work options

This story was originally featured on Fortune.com

© Luis Alvarez—Getty Images

• Self-made multimillionaire Emma Grede has built billion-dollar brands with the Kardashians (including shapewear and clothing brand company Skims), sits on the board for the Obama Foundation, and has just teamed up with tennis champion Coco Gauff on a mentorship campaign with UPS. But while scaling businesses and mentoring others come naturally to her, Grede admits she needed a mentor moment of her own when it came to artificial intelligence. And that moment came courtesy of fellow Shark Tank investor Mark Cuban, Grede exclusively tells Fortune.

The British-born entrepreneur Emma Grede, best known as the founding partner of Kim Kardashian’s $4 billion shapewear empire Skims and the CEO of denim brand Good American, has built a reputation on spotting cultural shifts before they hit the mainstream. 

When her and Khloe Kardashian’s Good American denim line dropped, it made $1 million on day one, making it the biggest denim launch in apparel history. Grede has helped redefine inclusion in retail and became the first Black female investor on Shark Tank—all before turning 45.

Now she’s bringing that same playbook to small businesses through a new UPS campaign alongside tennis star Coco Gauff. The initiative sees Grede mentoring creators of emerging female-led brands and offering one-on-one coaching to help them scale. 

But while mentoring others comes naturally to her, Grede admits that when it came to AI, she was the one who needed a pep talk—and fellow Shark Tank star Mark Cuban was the one who gave her the push to come to grips with the new technology.

In an exclusive interview with Fortune, Grede talked about an episode of her hit podcast show Aspire that hadn’t aired yet, where the two sat down and compared their AI usage. 

“I was already kind of getting there, but if I’m really honest, that episode where we really delved into AI gave me a new urgency around how I use AI,” she recalled, adding that Cuban had a staggering 60 AI apps on his phone. “Yeah, he gave me a kick.”

As soon as the recording wrapped up, she said that she started looking into AI courses at the Wharton School and Harvard for this fall. “I need to figure this out, because I’m using AI like a 42-year-old woman,” Grede candidly admitted while laughing.

Grede gave her staff a cash bonus for using AI—long before she realized she was behind

Grede isn’t completely new to AI. In fact, she was ahead of the curve when it came to encouraging AI adoption within her companies.

“About two years ago I put a note out in my office giving a cash bonus to anyone that uses AI in their work,” she explained, adding that the incentive was a big hit—especially with the marketing and finance teams.

“It changed the office. It changed the way people presented their work. It changed the way people did their work.”  

But as her Gen Z and thirtysomething staff embraced experimenting with ChatGPT and other new AI launches at the time, Grede admitted that she perhaps leaned too heavily on them. It meant that until recently, she’s been using AI more as a search engine and leaving her staff to handle the rest.

“I was like, Emma, you need to sort that out.”

It comes as many other CEOs are scrambling to appoint AI leaders, future-proof their business, and brace for change.

Billionaire Microsoft cofounder Bill Gates says AI is moving at a speed that “surprises” even him and that even if workers learn how to use the latest tech tools, they may still find themselves out of a job. Meanwhile, an ex-Google exec says CEOs are currently too busy “celebrating” their efficiency gains to see they’re next on AI’s chopping board.

But she’s not using AI to make her more productive

As one of America’s richest self-made women—with a reported net worth of nearly $400 million and at least four major businesses to her name—Grede is clearly ruthlessly efficient. But in her eyes, AI isn’t about squeezing even more productivity from her day.

“I’m probably the most productive person in the world. I don’t know that I can be that more productive,” she said, noting that her time is mostly spent making high-stakes decisions—not executing tasks. 

“There’s no amount of AI that can help me with that.”

But where it can help, she said, is in making smarter strategic choices and reshaping how she leads. 

“I think it’s a reframing of how we’re going to do things,” Grede added. “So much of my job is about making really big bets and decisions. And so if I can put data in places to optimize that decision making, I think that that’s probably where I’m going to be using it most.

“When you start to think about my role as a merchant and as a planner, it’s really those things that I think are going to fundamentally shift.”

In her podcast episode with Cuban, which has since been released, the television personality and Dallas Mavericks owner had a stark warning for founders who don’t embrace AI: “You’re f–ked…That’s like saying, back in the day, ‘I don’t need to use a PC, I don’t need to use the internet. I don’t need a cell phone.’”

He added, “If you’re an entrepreneur, or want to be an entrepreneur, start playing with it to get a sense for how it works, how to prompt. It becomes like having an entire staff of 1,000 business professors.”

This story was originally featured on Fortune.com

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