Masters in Business
Masters in Business

At The Money: Our Complicated Relationship With Cash

In this episode, Dr. Daniel Crosby sits down with Barry Ritholtz to discuss how to improve our relationship with money and earning, investing and spending our cash. Crosby is Chief Behavioral Officer at Orion Advisor Solutions, where he helps financial advisors apply behavioral science in their prac

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Episode Summary

Executive Summary: The episode argues that true wealth is broader than money: it includes relationships, meaning, engagement, growth, and time. Behavioral biases like ego, emotion, attention, and conservatism distort financial decisions. Money can increase happiness when spent on meaningful experiences or services, but lasting well-being depends on purpose, delayed gratification, and a financial plan rooted in personal values rather than imitation.

Main Topics: Redefining true wealth (Priority: 5/5): Dr. Daniel Crosby frames wealth as more than net worth, emphasizing positive experiences, engagement, relationships, meaning, and personal growth as the real markers of a life well-lived. Behavioral biases in money decisions (Priority: 5/5): The discussion identifies four meta-biases—ego, emotion, attention, and conservatism—that commonly lead people astray in financial planning and investing. When money does and doesn’t buy happiness (Priority: 4/5): The conversation distinguishes between momentary happiness and life satisfaction, arguing that money can improve well-being when used to remove disliked tasks or fund meaningful experiences. Delayed gratification versus instant reward (Priority: 5/5): Crosby explains that long-term success in life and finance often comes from resisting immediate gratification and maintaining a compelling vision of the future. The psychology of spending in retirement (Priority: 4/5): He notes that shifting from saver/investor identity to spender/donor is psychologically difficult because many people fear seeing their wealth decline after decades of accumulation. Financial planning grounded in values (Priority: 5/5): A good financial plan should start with a deep understanding of what clients actually value, since people often imitate others rather than articulating their own goals.

Key Arguments: True wealth is not a number; it includes relationships, meaning, engagement, positive experiences, and advancement. The most predictive element of true wealth is relationships, not financial accumulation. Four common meta-biases distort money decisions: overconfidence, emotional thinking, media-driven attention errors, and risk-averse conservatism. Money boosts happiness differently depending on measurement: momentary happiness plateaus faster than life satisfaction. Spending on disliked chores or meaningful experiences can materially improve quality of life. Delayed gratification is a major predictor of success across life domains, while impulsivity drives many failures. As people age, they often become better at self-control and interpersonal behavior, though decline can occur later in life. The hardest financial transition is moving from saving to spending/donating in retirement because many people are emotionally attached to their account balance. Purpose is the key force that can overcome fear of spending and make wealth useful for family, philanthropy, or shared experiences. Effective financial planning requires going beyond shallow questions and imitation-based goals to uncover a client’s real values and vision for a good life.

Data Points: Psychological biases impacting money: 200+ - Crosby notes there are well over 200 psychological biases affecting financial behavior. Core elements of a life well-lived: 5 - He cites positive experiences, engagement, relationships, meaning, and advancement from positive psychology. Wealth and life satisfaction threshold: Up to about $500,000/year - He says self-appraisal of life quality tends to rise with wealth up to roughly this level. Research sample on money disagreements: 400+ couples - Crosby interviewed couples to identify common sources of disagreement about money.

Pivotal Quotes: "What it isn't is just a number." — Dr. Daniel Crosby: Defines true wealth by rejecting a purely financial definition. "The number one source of disagreement was whether money is better used to enjoy today or to secure tomorrow." — Dr. Daniel Crosby: Summarizes a major conflict in couples’ financial behavior. "You have to have a yes burning inside of you that's bigger than the no." — Dr. Daniel Crosby: Explains how purpose can overcome fear of spending and support long-term financial choices.

Implications: Listeners should think about money as a tool for meaning, relationships, and future purpose—not just accumulation. Advisors and families may need deeper value-based conversations to build plans people will actually follow.

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About Masters in Business

Barry Ritholtz speaks with the people that shape markets, investing and business.

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