Power Couple: Debbi “Mrs.” Fields and Wade Shealy

Power Couple: Debbi “Mrs.” Fields and Wade Shealy

Author: Paul Ollinger April 24, 2024 Duration: 55:22
Debbi Fields founded Mrs. Fields cookies brand when she was in her early 20s and built the company into a well-known global brand. Wade Shealy got his start selling Bibles door-to-door then went on to develop and sell > $3 billion in resort real estate over the next few decades, including Hampton Island, GA whose residents include Ben Affleck / Jennifer Lopez and Robert / Lydia Monday. He is now CEO of Third Home, a vacation home sharing platform that empowers its members to see the world. In this week’s epiosde, these two wildly accomplished humans share lessons about entrepreneurship, friendship, and raising stable kids in an atmosphere of affluence. Debbi tells the story of how she went from Oakland A’s ball girl to cookie kingpin and her commitment to quality over cost control. She also tells us how she kept a positive attitude when circumstances compelled her to give up control of the company. Wade emphasizes the importance of motivation, positive attitude, and controlling one's thoughts in achieving success. Both discuss their commitment to friendship. Learn more about ThirdHome here.


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About Crazy Money: Unlike traditional personal finance shows, Crazy Money is not about how to make a million bucks, how to beat the stock market, or how to save money by switching credit cards. It is about deciding what role we want money to play in our lives and how we can use it to be our best selves. Topics covered include: philosophy, happiness, contentment, meaning, dreams, purpose, success, society, mental health, Buddhism, Stoicism, the hedonic treadmill, morality, business, work, careers, authors, books, consumerism, values, capitalism, economics, investing, saving, spending, personal finance, charity, philanthropy, altruism, affluence, wealth management, culture, society, status, ambition, accomplishment, perfectionism. Today’s episode covers: entrepreneurship, customer experience, real estate, motivation, positive attitude, friendships, family, friendship. Please stop reading and have a great day. Paul loves you.

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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

Reasonably Happy with Paul Ollinger
Podcast Episodes
Stoic Street Smarts w/ Ed Latimore [not-audio_url] [/not-audio_url]

Duration: 1:08:48
Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a professional boxer and earn a degree in Physics. I spoke to Ed…
Soul on Fire w/ John O’Leary (Encore episode) [not-audio_url] [/not-audio_url]

Duration: 52:07
John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played with fire and got burned. Like really, really burned, over 10…
Why You Will Never Feel Rich w/ Daniel Crosby [not-audio_url] [/not-audio_url]

Duration: 56:27
Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and Meaning. We cover the fun, non-obvious asp…
Why Two Parents Are Better Than One w/ Melissa Kearney (Encore) [not-audio_url] [/not-audio_url]

Duration: 40:55
Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically controversial fact that children raised in two-parent homes…
Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark [not-audio_url] [/not-audio_url]

Duration: 41:15
If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most u…
Laughing at Death w/ John Kenney [not-audio_url] [/not-audio_url]

Duration: 53:15
What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In this episode, I (i.e., me–Paul–the host) sit down with John K…
Rise of Populism w/ Brad Todd [not-audio_url] [/not-audio_url]

Duration: 48:56
Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in American politics. From growing up in East Tennessee to advising s…
From Prison to Oprah [not-audio_url] [/not-audio_url]

Duration: 56:52
What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New York Times bestselling author? In this unforgettable episode,…
Vote for Jesus! w/ Jonathan Rauch [not-audio_url] [/not-audio_url]

Duration: 45:20
What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan Rauch returns to the podcast to talk about his new book 'Cross-P…
Tribalism is Dumb (w/Andrew Heaton) [not-audio_url] [/not-audio_url]

Duration: 1:06:10
Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism comes from, how it is tearing us apart, and how we might fix…