Crazy Money with Paul Ollinger

About Crazy Money with Paul Ollinger

Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward. words.paulollinger.com (https://words.paulollinger.com?utm_medium=podcast)

Publisher

Paul Ollinger

Category

business · society & culture

Language

en

Explicit

No

First episode

30 Jan 2019

Latest episode

7 May 2026

Latest episodes

86 of 320 episodes have a transcript.

1. 

   7 May 2026TRANSCRIPT

   How to Get Rich in America

   ✍️ Follow Paul Ollinger on Substack by clicking here (https://words.paulollinger.com/) ✍️ “Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But my guest today calls this hogwash, baloney, and complete malarkey. Joseph Moore is a historian, entrepreneur, investor, and the author of a new book called How to Get Rich In American History: 300 Years of Financial Advice that Worked (And didn’t) in which he explores how ambition, risk, and reinvention have shaped America from the very beginning. He also reveals the money myths, sacred cows, side hustles, and NAYsayers that have always been a part of our society. What if so-called timeless beliefs about money like “invest for the long run,” “compound interest builds wealth,” and “real estate always goes up” weren’t always true…and play out less often than you think they do. Joseph’s book is part history, part playbook, and part reality check. He brings lessons to life with rigor that is deeper than an oil well and a wit that is dryer than the Texas plains. And in so doing he demystifies the past in order to clarify the present for anyone thinking about money, success, and what it really means to “make it” in America. 📕 Follow Joseph here (https://substack.com/@josephmoorebooks). 📗 To hear more, visit words.paulollinger.com (https://words.paulollinger.com?utm_medium=podcast&utm_campaign=show-notes-spotify-open-access)

2. 

   19 Mar 2026TRANSCRIPT

   Money, Fame, and Misery: Meet the Beatles

   Paul Ollinger interviews rock music writer Peter Doggett about The Beatles' struggles with fame, money, and misery, revealing how success doesn't guarantee happiness.

3. 

   12 Mar 2026TRANSCRIPT

   Believe and You Will See! (w/ Nir Eyal )

   Host Paul Ollinger interviews author Nir Eyal about how beliefs shape our potential and drive extraordinary results, even when not factually true.

Inside a recent episode

How to Get Rich in America

Published 7 May 2026 · Transcript excerpt

[…] All right, here's an unpopular opinion. It is the single most important financial decision of your entire life period. And it not only was it, it still is. If you go back to all of your American history, marriage advice was the number one piece of financial advice you would get for men and for women. […]

Who has been a guest on Crazy Money with Paul Ollinger

Names identified in recent episode analyses. Showing up to five guests.

• Peter Doggett
• Nir Eyal
• Matt Kaplan
• Ben Markovits
• Laura Delano

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

268,123

Score snapshot 15 Sept 2025

Apple Podcasts (US)

4.9 / 5

440 ratings

Spotify

4.9 / 5

49 ratings

Podcast Authority Score: 81 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

90

Social presence

0

YouTube

86

Engagement

93

Contact Crazy Money with Paul Ollinger

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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