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 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 49-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,” he said. “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,” he continued. “The joy of appreciating what we have and making those hard choices is really foundation.”

Part of 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 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  3,302 people are now billionaires—and the number of people to join that list keeps growing at a record pace as experts predict AI could fuel 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 President Donald Trump’s inauguration, dripping in diamonds and designer gear. Most recently, Jeff Bezos’ 2025 $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,” he continued. “That would be great if I didn’t have to ask VCs. But you know what that is? That’s accountability.”

A version of this story originally published on Fortune.com on  August 15, 2025.

Read more about wealth from Fortune’s Orianna Rosa Royle:

• Ultrawealthy are looking to leave the U.K. thanks to tax hikes—but the CEO of $1 billion tax platform says it’s their ‘social responsibility’ to stay
• Like Bill Gates, this billionaire is cutting his kids inheritance to 8 figures because he’d rather give more to philanthropy than his great-grandkids
• Ikea’s billionaire founder was so frugal that he bought clothes from flea markets and took free salt and pepper from restaurants
• Billionaire says he can tell if you’ll stay stuck in the middle class forever with a simple marshmallow test—but even your car can give it away