Joining a millionaire or billionaire family may sound like a dream, but acclaimed author Malcolm Gladwell argues that extreme wealth can deprive children of something vital: the drive to achieve on their own.

"I would rather have a dad who made $100,000 than have a billion," Gladwell said during a 2009 lecture at Microsoft that has recently resurfaced on social media. "I think that having a father with a billion dollars would actually be quite crippling to your motivation, and so that's an advantage that's actually a disadvantage."

Gladwell, 62, has built an estimated $30 million net worth through his career as a journalist, best-selling author, and podcaster. His argument is not that children must grow up in poverty to succeed. Rather, he believes there is an ideal middle ground between financial hardship and extreme abundance—enough resources to provide stability and opportunity, but not so much that a child is shielded from the constraints, disappointments, and effort that forge ambition.

The lecture's renewed circulation comes amid intensifying public debate over the so-called Great Wealth Transfer, in which financial research firms estimate that baby boomers are projected to pass down tens of trillions of dollars to younger generations over the coming decades—raising questions about whether inherited wealth serves as a springboard or a crutch. Some of the world's wealthiest individuals have publicly reached conclusions similar to Gladwell's. Warren Buffett, chairman and CEO of Berkshire Hathaway, has famously said he plans to leave his children enough money so that they could do anything, but not so much that they could do nothing. Through the Giving Pledge, an initiative Buffett launched with Bill and Melinda Gates in 2010, more than 240 of the world's wealthiest individuals and families have committed to giving away the majority of their fortunes to philanthropy.

Gladwell expanded on this idea in his 2013 book, David and Goliath: Underdogs, Misfits, and the Art of Battling Giants. In it, he interviewed one of the "most powerful people in Hollywood," whom he left unnamed, and that executive echoed the same sentiment.

"My own instinct is that it's much harder than anybody believes to bring up kids in a wealthy environment," the executive said. "People are ruined by challenged economic lives. But they're ruined by wealth as well because they lose their ambition and they lose their pride and they lose their sense of self-worth. It's difficult at both ends of the spectrum. There's some place in the middle which probably works best of all."

Elite Education Can Backfire

Education offers another illustration of how a presumed advantage can become a liability. Gladwell has questioned whether elite schools always deliver the educational benefits their price tags imply.

"I would love to know on a systematic analysis of why it is the case that you're better off going to that school than learning how to cope in a far more heterogeneous, rough and tumble public school environment," he said in the 2009 Microsoft lecture.

Beyond cost, Gladwell has long maintained that success is not determined solely by raw ability—relative standing matters, too. Being surrounded exclusively by high-achieving peers can sometimes work against a student. This aligns with a well-documented concept in educational psychology known as the Big Fish Little Pond Effect, which describes how students' academic self-concept is shaped more by their standing within their immediate peer group than by their absolute performance—an idea Gladwell examined at length in David and Goliath.

"If you're interested in succeeding in an educational institution, you never want to be in the bottom half of your class. It's too hard," Gladwell said on the Hasan Minhaj Doesn't Know podcast last year. "So you should go to Harvard if you think you can be in the top quarter of your class at Harvard. That's fine. But don't go there if you're going to be at the bottom of class. Doing STEM? You're just gonna drop out."

Research supports the idea that extreme privilege carries real risks. A 2005 study by Columbia University researchers found that children from upper-class families can show elevated rates of substance use, anxiety, and depression, partly due to excessive pressure to achieve and isolation from parents.

"The American dream spawns widespread beliefs that Ivy League educations and subsequently lucrative careers are critical for children's long-term happiness," the researchers wrote. "In the sometimes single-minded pursuit of these goals, let us not lose sight of the possible costs to mental health and well-being of all concerned."

Humble Beginnings as a Driving Force

Conversely, numerous business leaders have said that growing up with limited means became a source of motivation rather than an obstacle.

Ulta Beauty CEO Kecia Steelman is one example. She previously told Fortune that she grew up "poor, hungry and determined" in rural Iowa. After becoming pregnant as a teenager, she took a job as a floor associate at Target earning $8 an hour and began working her way up the retail ladder. Last year, she was named CEO of Ulta—the country's largest beauty retailer, with approximately 1,500 stores.

"Being really grounded and humble with my beginnings, I wouldn't change that," Steelman said.

Former PepsiCo CEO Indra Nooyi has similarly credited her upbringing and early hardships with shaping her work ethic. She arrived in the United States in the late 1970s to pursue graduate-level management studies at Yale University. To finance her degree, Nooyi worked the midnight-to-5 a.m. shift as a dormitory receptionist before attending classes each morning.

Reflecting on her journey, Nooyi said the U.S. offered something more valuable than an easy path to success: the possibility of forging one.

"I remember back in the old days people would say they thought the streets might be paved with gold," she said. "Maybe they weren't paved with gold, but they were paved with the possibility of ambition."

Nvidia CEO Jensen Huang has likewise argued that learning to endure some struggle—and building the capacity to push through challenges—is part of what separates successful people from the rest.

"Let the suffering come to you a little bit at a time," Huang said last month at Y Combinator's Startup School 2026. "Don't imagine how hard it's going to be and let all of that turn into anxiety and not doing something about it. You want to imagine in your head, 'How hard can it be?'"

This story was originally featured on Fortune.com.