What’s it like to launch a financial career at the worst possible moment?
Douglas Boneparth, CFP and president of Bone Fide Wealth, moved to New York City in 2008 as Bear Stearns collapsed and the Great Financial Crisis began. But his money story started much earlier — in a household where personal finance was never taboo. He talks with Chris Hill about:
- Early lessons in entrepreneurship
- The challenge of leaving a family firm to build his own path
- Managing student debt and New York City rent
- An investing lesson he wishes he had learned earlier
Opening clip – “Succession”

Check out Money Together, the best-selling book Douglas wrote with his wife Heather.

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Tim Hanson didn’t set out to become a capital allocator.

Today he’s the President and CIO at Permanent Equity, helping steward long-term investments in private companies built to last. But his path to investing included playwriting, early stock picks, and lessons about money that started in childhood. Chris Hill talks with Tim about what separates investing from allocating capital — and why the distinction matters, as well as:
- The first stock Tim ever bought (and what he learned from it)
- How Permanent Equity thinks about holding businesses for decades
- Raising kids who understand ownership
- A surprising purchase that says more about capital discipline than you’d think
Opening clip – “Glengarry Glen Ross”

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Personal finance isn’t just math—it’s memory, emotion, and lived experience.

Chris Hill talks with MarketWatch columnist Beth Pinsker about why money decisions feel so hard, especially during life’s biggest transitions. Drawing from her work as a journalist and financial planner, Beth breaks down caregiving, taxes, and end-of-life planning in ways that actually make sense.
They discuss:
- How childhood money experiences shape adult behavior
- What financial planners can—and can’t—help with during crises
- Why “bad choices” are sometimes the only choices
- What she learned about profit, inventory, and responsibility while illegally selling soft drinks on the beaches of Atlantic City

Opening clip – “The Princess Bride”

Beth’s new book, My Mother’s Money: A Guide to Financial Caregiving, can be found at BethPinsker.com.

What’s the last thing you splurged on?
Got a purchase you regret and still think about?
Share your story at info@moneyunpluggedpod.com