The Pressures of Privilege

Privilege is supposed to set you free. So why doesn't it? The Pressures of Privilege goes inside the worlds of wealth, status, achievement, and family legacy—with inheritors, founders, advisors, doctors,...more

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Latest Episodes

Ep20 Dr. Paul Hokemeyer - Why Your Therapist Might Be Too Intimidated to Actually Help You (And What That's Costing You)

January 12, 2026

Ep20 Dr. Paul Hokemeyer - Why Your Therapist Might Be Too Intimidated to Actually Help You (And What That's Costing You)

What happens when the very wealth that's supposed to solve all your problems... becomes the reason you can't get the help you desperately need?...

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00:59:11

Ep19 Dorie Clark - From Journalism Deadlines to Life's Long Game

December 24, 2025

Ep19 Dorie Clark - From Journalism Deadlines to Life's Long Game

How do you build something meaningful when every cell in your body is screaming for instant results? Diana sits down with her longtime friend,...

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00:50:18

Ep #18 - Be like water | Grigorios Zamparas

November 28, 2025

Ep #18 - Be like water | Grigorios Zamparas

My piano teacher Grigorios joins me to talk about what happens when you stop forcing things and start flowing instead. We go back to...

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00:48:44

Ep #17 - Losing control and finding beauty | Rossella Vasta

November 16, 2025

Ep #17 - Losing control and finding beauty | Rossella Vasta

In this conversation, Rossella Vasta shares her profound journey as an artist and educator, reflecting on her experiences with paralysis, the healing power of...

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01:03:37

Ep #16 - The 4 forces that control every family  | John Messervey

October 31, 2025

Ep #16 - The 4 forces that control every family | John Messervey

In this conversation, John Messervey and Diana Oehrli explore the complexities of family dynamics, wealth distribution, and the impact of modern technology on relationships....

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00:57:17

Blogcast: He built an empire. We voted to end it.

October 13, 2025

Blogcast: He built an empire. We voted to end it.

My great-great-grandfather, Frederick H. Prince, built a fortune on stockyards, railroads, and meatpacking. By the early 1900s, he controlled hundreds of miles of rail...

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00:04:53

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