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In this initial episode of Rabbithole of our new show Rabbithole, Dave Nadig explores the psychology of money and investing with Barry Ritholtz, author of "How Not to Invest."

Their conversation challenges conventional financial wisdom and reveals insights about what money is, and how we use and invest it.

Key topics include:

Why money is a tool for freedom and agency, not a store of value or end goal

How childhood experiences shape our lifelong money behaviors and attitudes

Why market crashes affect us differently at various life stages

The dangers of algorithmic social media and information overload for investors

Why avoiding mistakes is more important than chasing extraordinary returns

Rethinking Bitcoin and other investments through better framing

The wisdom of humility in financial decision-making

Barry shares candid personal stories and draws on decades of experience as a trader, strategist, and wealth manager to identify the ideas, numbers, and behaviors that typically destroy wealth.