“My money philosophy is that money is a tool to drive your fulfillment, and that’s it,” Perkins said in a recent interview with the Wall Street Journal. “And if you don’t have these big, expensive dreams, you don’t necessarily need that much money.”

Perkins knows the value of enjoying the spoils of his success while he’s alive; the financier and poker player self-identifies as a “risk taker,” and admits his wealth is always in flux. He started his career on the trading floor of the New York Mercantile Exchange, later working as a trader and risk manager at several large energy firms, playing a significant trading role at hedge fund Centaurus Energy. Perkins then went on to found several companies of his own, including Skylar Capital, a fund to trade U.S. gas futures, options, and swaps; private equity and VC firm Small Ventures USA; and SkyFi, a provider of Earth observation data. 

The 57-year-old’s rise in wealth was anything but meteoric. But the ups and downs of his net worth—estimated to be upwards of $100 million, with some sources citing $500 million—don’t faze him. The “Die with Zero” author is keen to spend and pass down all his money before the end of his life so he can experience its impact in real time. 

“I use an example of Chuck E. Cheese tokens: spend all your Chuck E. Cheese tokens while in Chuck E Cheese, they don’t translate well into the world,” Perkins explained. “It makes sense for you [to] use all your resources to drive your fulfillment while you’re alive.”

For the “Cowboy of Wall Street,” that means anything from amassing a $22.5 million art collection to spending more than $250,000 annually on longevity treatments like body diagnostics. And he’s spreading the wealth, too; Perkins said that one year he gifted $16,000 tax-free to 30 to 40 people in his life. Plus, his daughters will get a piece of the pie—and sooner, rather than later.

“Whatever money you decide to give to your kids, you should probably give the money to them where it has a maximum impact in their life,” Perkins said. “Not when you’re 60, when you die.”

The CEOs determined to shed their fortunes

Perkins’ money philosophy stands out in a sea of wealthy entrepreneurs accruing wealth that could sustain generations. But he joins a growing movement of the ultra-rich promising to offload their fortunes during their lifetimes. 

Some have already lived up to their vow. Chuck Feeney, the late cofounder of Duty Free Shoppers Group, gave away almost his entire $9 billion fortune before his passing in 2023. The entrepreneur distributed his money among charities, universities, and foundations, living out his later years in a two-bedroom apartment with his wife. And steel tycoon Andrew Carnegie was very nearly successful in his mission to give away his entire fortune, distributing $350 million at the end of his life, with $30 million left over. 

Others are chipping away at their fortunes over time—and super philanthropist MacKenzie Scott is ramping up her efforts to redistribute her wealth. The early Amazon employee and ex-wife of Jeff Bezos donated a whopping $7.2 billion in 2025 alone to colleges, climate nonprofits, and community support groups. Scott, worth $43.8 billion, was named the third most generous philanthropist in the world, having given away 46% of her net worth, according to an analysis from Forbes earlier this year. And she says she has no plans to slow down until her accounts run dry.

“We each come by the gifts we have to offer by an infinite series of influences and lucky breaks we can never fully understand,” Scott wrote in her 2019 letter joining philanthropic initiative The Giving Pledge. “I have a disproportionate amount of money to share. My approach to philanthropy will continue to be thoughtful. It will take time and effort and care. But I won’t wait. And I will keep at it until the safe is empty.”

And just like Perkins, billionaire businessman Mike Bloomberg believes it’s best to exhaust his fortune while he’s alive to see it in action. The prolific philanthropist worth $109.4 billion has donated more than $21 billion to efforts ranging from education to the climate; Bloomberg was even named the largest donor of 2024 for his $3.7 billion in giving, according to the Chronicle of Philanthropy. He was also the biggest giver of 2023; the 84-year-old has promised to leave his company to Bloomberg Philanthropies “when he dies, if not sooner.”

“I’ve never understood people who wait until they die to give away their wealth. Why deny yourself the satisfaction?” Bloomberg wrote in an email to the Chronicle. “I’ve been very lucky, and I’m determined to do what I can to open doors for others and to leave a better world for my children and grandchildren.”