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
I sleep with a blankie | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 56:17
Paul sits down with lawyer turned comedian Liz Glazer to discuss how a successful lawyer and law professor can find happiness by saying goodbye to a tenured career by pursuing a life in the arts.Follow Reasonably Happy h…
Start Thinking Rich | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 57:25
Join us for an insightful conversation with Adrian Brambila and Brad Klontz, authors of "Start Thinking Rich," as we dive deep into the mindset strategies that lead to success. Discover how your background, no matter the…
Claiming Confidence | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 54:06
We are joined by Lydia Fenet, the founder and CEO of the Lydia Fenet Agency, a boutique agency representing best in class charity auctioneers. Lydia is a best selling author and ground breaking art auctioneer who sits wi…
What Cocaine Taught Me | Reasonably Happy with Paul Ollinger [not-audio_url] [/not-audio_url]

Duration: 53:33
We are joined by New York Times best selling author and former Wall Street wild man Turney Duff to discuss Hookers, Blow, Million-dollar bonuses on Wall Street and the journey through recovery and what lies the other sid…
The People Who Never Quit with Henry Oliver [not-audio_url] [/not-audio_url]

Duration: 57:40
What did Ray Kroc, Maya Angelou, Margaret Thatcher, and Malcolm X all have in common? (Don’t worry - this isn’t a dirty joke!) They were all opsimaths, i.e. a person who blooms late in life. In his new book SECOND ACT: W…
A Poet’s Life (with In-Q) [not-audio_url] [/not-audio_url]

Duration: 50:06
Nobody gets into poetry for fame and fortune. And yet, there might be a tiny bit of each happening for In-Q, my guest this week who is a renowned poet and spoken word artist. When he started freestyling (aka, “rapping" f…
“Second Class” Americans with Batya Ungar-Sargon [not-audio_url] [/not-audio_url]

Duration: 41:30
The spirit of the working class is crushed. So argues Batya Ungar-Sargon in her new book 'Second Class: How the Elites Betrayed America's Working Men and Women’. Batya says that working men and women in the United States…
Why the News is Bad with Angus Hervey [not-audio_url] [/not-audio_url]

Duration: 39:00
**Hi friends - this is Paul writing to confess to an error in my introduction in this week's episode. The name of Angus Hervey's podcast is "Hope Is a Verb," not—as I called it—"Hope is NOT a Verb," which is kind of the…
Fighting for the Family Business with Stephanie Stuckey [not-audio_url] [/not-audio_url]

Duration: 48:11
Stephanie Stuckey used her life’s savings to buy the company that is her family’s legacy. At it’s height in the1960’s and 70’s, there were hundreds of Stuckey’s stores selling gas, pecan candy, cold drinks, and quick mea…
Persevering Through Grief with Nicole Avant [not-audio_url] [/not-audio_url]

Duration: 55:42
Nicole Avant is the former U.S. Ambassador to the Bahamas and author of a new memoir, 'Think You’ll Be Happy: Moving through Grief with Grit, Grace, and Gratitude’ which tells the story of her extraordinary family and he…