Billionaires often feel isolated, Mr. Klontz said, and find it difficult to trust people or have authentic relationships that are not about money.

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“Although they know money is not the key to happiness, they can’t stop counting it,” Mr. Klontz said. It’s especially challenging for those who are self-made, as opposed to those who inherit a fortune. For self-made billionaires, he said, “Their entire self-image and all their self-esteem is wrapped up in the pursuit of money.”

Billionaires often feel isolated, Mr. Klontz said, and find it difficult to trust people or have authentic relationships that are not about money. On top of that, they have a hard time finding a sympathetic ear. “There is a sense they can’t really tell anyone what they are dealing with, because no one wants to hear about their struggles,” he said. “As a society, we don’t have the head space to entertain the notion of a billionaire having a bad day.”
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Becoming a counselor for the ultrarich was a long journey for Mr. Klontz, who grew up outside Detroit. His parents divorced when he was 2, and his mother, a part-time kindergarten teacher pregnant with his sister at the time, was granted full custody. Although she remarried a few years later to a high school teacher, their economic situation barely improved. Mr. Klontz said they went from being under “tremendous financial strain” to straddling the lower- to middle-class line during the rest of his childhood.

Despite earning a doctorate in psychology, he remained financially strapped, graduating with $100,000 in accumulated student loan debt and a lot of anxiety about it.

But it was 1999, and many of his friends were making lots of money trading stocks. “I thought: This is what rich people do, so I’ll do this, too,” he said. Mr. Klontz sold his truck for about $7,000, bought a $450 car and threw everything that was left into tech stocks. “In three months the bubble burst and I lost everything I invested.”

Rather than blame the market, Mr. Klontz decided to figure out what had caused his behavior. “I went home and interviewed several of my family members about their relationship with money,” he said. “I found stories that blew my mind. But the one that is most salient, is that my grandfather lost all the family’s money in the Great Depression and after that, never put a dollar in a bank again, not for the rest of his life. He died in his 90s, living in a trailer park.”

Mr. Klontz became interested in learning more about his family’s enormous anxiety around money. His mother, for example, had so much anxiety around it that she put every cent she saved into low-interest-bearing certificates of deposit, rather than the stock market. “I saw these patterns around money in families that I call dysfunctional pendulum swing: You either do exactly what your parents did or the exact opposite,” he said. “And that’s what I did: I did the riskiest thing you could do.”

After his stock market gamble, it took him three years of living extremely close to the bone to pull himself out of debt. The desire to understand the financial beliefs and behaviors of his own, lower-income family led him to dissect the behaviors and beliefs of high-net-worth individuals. And now he works with some of the wealthiest people in the world, many of whom came to him after reading his books or being referred by other clients.

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“They [Billionaire's] often have a distorted feedback loop. People are drawn to them for their status and perceived power, so they tend to be surrounded by people who endorse their worldview and don’t challenge their way of thinking. Very few people are honest with them.”