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
On The Move [not-audio_url] [/not-audio_url]

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Who killed Rudolf Diesel? (with Doug Brunt) [not-audio_url] [/not-audio_url]

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Yes, there was actually a guy named Rudolf Diesel who actually invented the diesel engine, which was incredibly revolutionary for its time. It earned Diesel a massive fortune and had huge implications for how war—especia…
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Duration: 1:01:33
Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no nudity in either), and The Centrist Manifesto, all of which…
Mike Posner on Life Beyond Fame and Fortune [not-audio_url] [/not-audio_url]

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Mike Posner is a Grammy-nominated rapper, singer, songwriter, and music producer from Detroit. His Spotify channel has generated over 3 billion plays and his song 'I Took a Pill in Ibiza' reached the top five on the Bill…
Andrew Yang on Our Broken Political System (Encore) [not-audio_url] [/not-audio_url]

Duration: 50:56
Andrew Yang is a former Presidential and NYC mayoral candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for structural reform to safeguard our democracy. He la…
The Third Path with Jordan Harbinger [not-audio_url] [/not-audio_url]

Duration: 1:03:32
Jordan Harbinger is one of the most popular podcasters in North America, but it all started by accident. As a young University of Michigan grad, Jordan decided to go to law school because it was something to do after col…
Living The Constitution with AJ Jacobs [not-audio_url] [/not-audio_url]

Duration: 50:32
Good morrow, chum! My guest this week is A.J. Jacobs, author of the new / amazing book 'The Year of Living Constitutionally: One Man’s Humble Quest to Follow the Constitution’s Original Meaning’, in which A.J. chronicles…
Being Human at Work with Kim Scott, author of 'Radical Candor’ [not-audio_url] [/not-audio_url]

Duration: 1:00:48
‘Radical Candor’ author Kim Scott once had to inform a colleague that they smelled bad….like, really bad. She was able to do so becuase she had created on her team a culture or radical candor. No, this doesn’t mean you c…
Death, Dying, and Israel with Rabbi Steve Leder [not-audio_url] [/not-audio_url]

Duration: 1:09:16
Rabbi Steve Leder is the Senior Rabbi at Wilshire Boulevard Temple, a very large and influential congregation in Los Angeles. He is a New York Times best-selling author of several books, including 'For You When I Am Gone…
The Wealth Money Can’t Buy with Robin Sharma [not-audio_url] [/not-audio_url]

Duration: 40:48
Robin Sharma is a leadership expert, coach and author whose books have sold tens of millions of copies around the world. The author of The 5AM Club, The Monk Who Sold His Ferrari, The Everyday Hero Manifesto, and Who Wil…