Psychologist Daniel Crosby, Chief Behavioral Officer at Orion and host of the podcast Standard Deviations, calls sports betting “financial crack” and explains why confusing it with investing can be so costly.
But sports betting is just one part of a conversation that starts in Huntsville, Alabama, where his dad got a job as a stockbroker the day he was born. He talks with Chris Hill about:
- What a neighbor told him to do on Black Monday, when he was 7 years old
- Why a school form made him ask his parents, “Are we poor?”
- The therapy client who became the tipping point in his decision to leave clinical psychology
- How a house that doubled in value became “the dumbest thing” he’s ever done

THE BEHAVIORAL INVESTOR

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Opening clip – “Billions”

Everyone wants to know if AI is a bubble. Barry Ritholtz, chairman and CIO of Ritholtz Wealth Management, host of Bloomberg’s Masters in Business, and author of How Not to Invest, has a pointed answer. He also explains why investors should focus on “the Magnificent 493” instead of the Magnificent Seven.
But AI is just the start of a wide-ranging conversation about how a kid who grew up broke on Long Island built a career on understanding why smart people make bad money decisions. He talks with Chris Hill about:
- Why a 6th-grade class trip his family couldn’t afford still shapes the way he shops
- How his mother’s real estate career helped him see the 2008 financial crisis coming
- Why he didn’t start his Wall Street career until his mid-30s
- The startup pitch he called “the dumbest idea” he’d ever heard (and what it cost him)

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Opening clip – “Moneyball”

The fastest path to wealth isn’t cutting back. It’s learning to earn more money. “You can only cut to zero, but you can earn infinitely,” says Travis Chappell, host of the popular daily podcast Travis Makes Money.
At an early age he began preparing for a life in ministry before building a career in sales and entrepreneurship. He talks with Chris Hill about:
- Selling homemade rubber bugs to classmates as a kid—and charging extra for upgrades
- Knocking on doors for a solar company in college, and realizing he didn’t want to stop
- Why keeping your lifestyle in check is harder than earning more money
- The big purchase that gave him no buyer’s remorse (and how much he spent on Pokémon cards)

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Opening clip – “Margin Call”