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”

Every dollar you save is a gift to your future self. But what if that person feels like a stranger?
UCLA professor Hal Hershfield studies why that happens, and what it means for the money decisions we make now. Author of Your Future Self: How to Make Tomorrow Better Today, he talks with Chris Hill about:
- His first job picking corn for $5.25 an hour, and the calluses he carried into winter
- The spreadsheet he and his wife used to split expenses when they first moved in together
- A question he asks himself before making a big purchase
- When it makes sense to spend money today instead of saving it for tomorrow

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Opening clip – “Succession”

Cassie Holmes has spent her career studying how we spend our time and why it may matter more to our happiness than money. But her own relationship with money started with an argument she overheard as a kid.
Cassie is a professor at UCLA's Anderson School of Management and the author of the bestselling book Happier Hour: How to Beat Distraction, Expand Your Time, and Focus on What Matters Most. She talks with Chris Hill about how that early unease shaped her approach to work, spending, and time, as well as:
- A summer job that taught her something her Ivy League education hadn't
- Why her business school colleagues rolled their eyes at studying happiness (and what changed their minds)
- The one thing she spends money on that lines up perfectly with her research
- Her biggest money regret, and why it isn't something she bought
Every Money Unplugged interview is on our YouTube channel, PLUS animated clips of favorite moments from the show!

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Opening clip – “Jim Gaffigan: Comedy Monster”

Worth roughly $200 trillion, the bond market is bigger than the stock market, and even bigger than the entire banking system. Despite that, most investors barely think about it. Robin Wigglesworth, global finance correspondent and editor of FT Alphaville at the Financial Times, explains why it's the most important financial market of them all.
He talks with Chris Hill about:
- How a car wash taught him to read the fine print
- The market jitters in April 2025 that changed President Trump's mind
- A generational stock investment he almost made as a student
- Career advice you won't believe until you learn it the hard way
Check out Robin’s new book, A Fabulous Debt: The Epic Story of How Bonds Built the Modern World.

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Opening clip – “Heist”

Ian Cassel invests where almost no one else will: companies too small and too illiquid for Wall Street to touch. The founder of MicroCapClub sits down with Chris Hill to share what that world actually looks like from the inside, and why he believes it offers individual investors an edge, as well as:
- The fake identity he invented at 20 to talk his way into a one-on-one meeting with a public company CEO
- What he looks for beyond the financial statements when he meets with a company’s management
- A purchase he made in the depths of the 2009 crash that he still thinks about
- His dad's simple rule about charitable giving that took him a decade to understand
Check out Ian’s new book Stock Picker: How to develop the mindset, temperament, and strategy to outperform Wall Street.

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Opening clip – “Glengarry Glen Ross”

Scott Phillips is the Chief Investment Officer of Motley Fool Australia, host of the podcast Motley Fool Money, and author of the new book The One-Page Investing Plan.
He talks with Chris Hill about how his childhood money habits were shaped by his dad's labeled tobacco tins, and a financial decision in his 20s that still stings, as well as:
- The pay cut he took to become a professional investor
- A decision he and his wife made to prioritize financial peace of mind over maximizing their wealth
- Why the fear of a market crash doesn't get easier with experience
- How the movie Wall Street still holds up after nearly 40 years

Want to invest like the pros? Try TIKR for free at tikr.com/unplugged.

Opening clip – “Wall Street”