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Deeply Driven

Deeply Driven

By: Deeply Driven Podcast | Insights into Business History and Entrepreneurship
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 Welcome to Deeply Driven, a podcast exploring business history and the journeys of entrepreneurs. We exist to share success stories and lessons from the world of business.2025 Deeply Driven Podcast Economics Leadership Management Management & Leadership World
Episodes
  • #25 Isadore Sharp: The Work You Don’t See That Built Four Seasons

    #25 Isadore Sharp: The Work You Don’t See That Built Four Seasons
    Feb 7 2026

    This is the story of, Issy Sharp a quiet builder from Toronto who helped reshape the meaning of service, leadership, and workplace culture across the world.

    In this episode of Deeply Driven, we step inside the rise of Four Seasons and the steady, values-driven leadership of founder Isadore Sharp. What began as one small hotel in 1961 would grow into one of the most respected luxury brands in the world — and one of the longest-running companies ever named to Fortune’s list of the Best Places to Work, appearing every year from 1998 through 2020.

    Issy believed something simple but powerful. If you take care of your people, they will take care of your guests. And if you take care of your guests, the business will take care of itself.

    That sounds easy. It is not.

    Four Seasons built its name on trust, kindness, pride in craft, and steady day-by-day work. No shortcuts. No loud promises. Just clear values lived out through thousands of small acts — the way a guest is greeted, the way a team member is trained, the way leaders listen when problems show up.

    In this episode, we walk through how Issy shaped a culture that held strong through recessions, industry shifts, and rapid global growth. We also explore how Four Seasons earned one of the longest streaks ever on Fortune’s Best Companies to Work For list — proof that strong culture compounds over time.

    But this story is bigger than hotels.

    It is about the long game of leadership. It is about building teams that believe in the mission. It is about learning that service is not a slogan. It is a daily choice.

    If you lead a team, run a business, or dream of building something that lasts, this episode will speak to you. Four Seasons shows that true luxury is not marble floors or gold trim. True luxury is how people feel when they walk through your doors.

    This is the story of a founder who believed that the invisible parts of a company — trust, care, and purpose — often become the strongest parts of all.

    Deeply Driven Books (Amazon Affiliate) - 100% of commissions will be donated to help support Children’s Literacy!

    https://amzn.to/45R6rxC

    Big Shots Interviews with Issy Sharp
    How Issy Sharp Built The Four Seasons and Transformed The Hospitality Industry Forever (Part 1)
    An Unfiltered Conversation With The Founder of The Four Seasons: Issy Sharp (Part 2)

    Past Episodes Mentioned

    Estée Lauder: Divine Purpose of Beauty

    E18 Harry Snyder: In-N-Out and the Power of “Keep It Real Simple”

    #16 How Jim Casey Turned Service Into UPS's Superpower

    Sam Walton: Simple Ideas & Deep Business Impacts

    #10 Fred Rogers: Deep Business Lessons for Entrepreneurs

    If you enjoyed this episode, please leave us a review. It would greatly help the show and we thank you in advance for all your tremendous support.

    Deeply Driven Newsletter

    Welcome!

    Deeply Driven Website

    Deeply Driven

    X

    Deeply Driven (@DeeplyDrivenOne) / X

    Substack

    https://larryslearning.substack.com/

    Thanks for listening friends!
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    50 mins
  • #24 Jim Casey: Heart of Service Fuels Business Growth (UPS Founder)

    #24 Jim Casey: Heart of Service Fuels Business Growth (UPS Founder)
    Jan 30 2026

    Jim Casey built one of the largest companies in the world by holding onto a belief so simple it’s easy to overlook: service has no magic shortcuts.

    In this episode, we look at Jim Casey, the quiet, founder of United Parcel Service, and the lifelong philosophy that guided him from the streets of Seattle to the helm of a global enterprise. Casey started working as a messenger boy at a young age, driven less by ambition than by responsibility. From the very beginning, he learned something that never left him—anyone can move a package, but not everyone can be trusted to serve.

    Casey understood early that service isn’t glamorous. It’s repetitive. It’s costly. It requires discipline, honesty, and patience—especially on bad days. While competitors chased speed, scale, or clever tactics, Casey obsessed over something quieter: keeping promises, controlling costs, and empowering people to do their work well. He believed that real service compounds slowly, and that trying to rush it usually breaks the very thing you’re trying to build.

    Throughout his life, Casey repeated the same message to managers and employees alike. Service comes first. Not when it’s easy. Not when it’s profitable. But especially when it’s hard. He warned against shortcuts, tricks, and quick wins, insisting that the long road—done right—was actually the fastest way forward. In his view, putting reward ahead of service was like putting the trailer before the tractor. It might move for a moment, but it won’t get you where you want to go.

    This episode draws from Casey’s talks, his early experiences, and the culture he instilled at UPS over decades. It’s a reminder that the most enduring businesses aren’t built on hacks or slogans, but on habits—small things done well, day after day, year after year.

    If you’re building a business, leading a team, or simply trying to do meaningful work, Jim Casey’s life offers a timeless lesson: service isn’t magic—but it works. And when you commit to it fully, even the hard way becomes the right way.

    Past Episodes Mentioned

    #1 Henry Ford My Life and Work (What I Learned)

    #9 Sam Zemurray - The Banana Man (What I Learned)

    Kent Taylor and his Texas Roadhouse Dream

    Sam Walton: Simple Ideas & Deep Business Impacts

    #16 How Jim Casey Turned Service Into UPS's Superpower

    E18 Harry Snyder: In-N-Out and the Power of “Keep It Real Simple”

    Deeply Driven Books (Amazon Affiliate) - 100% of commissions will be donated to help support Children’s Literacy!

    https://amzn.to/45R6rxC

    If you enjoyed this episode, please leave us a review. It would greatly help the show and we thank you in advance for all your tremendous support.

    Deeply Driven Newsletter

    Welcome!

    Deeply Driven Website

    Deeply Driven

    X

    Deeply Driven (@DeeplyDrivenOne) / X

    Substack

    https://larryslearning.substack.com/

    Thanks for listening friends!
    Show More Show Less
    39 mins
  • #23 Michael A. Singer: Saying Yes to Life & Watching Everything Change

    #23 Michael A. Singer: Saying Yes to Life & Watching Everything Change
    Jan 22 2026
    There are some books that inform you. And then there are a few that quietly work on you, long after you’ve stopped listening. The Surrender Experiment by Michael A. Singer is one of those books.This episode is a little different from our usual founder story. Yes, there’s business here. Yes, there’s a remarkable company that grows into a hundred-million-dollar enterprise. But at the center of this story is something much more personal—and much more challenging: the idea of surrendering control over your own life.Michael Singer didn’t set out to build a company, a movement, or a legacy. In fact, he didn’t set out to build anything at all. What he did instead was make a radical decision early in his life: he would stop resisting whatever life placed in front of him. Not selectively. Not when it felt comfortable. But fully.That decision becomes the core of what he calls “the surrender experiment.”As you’ll hear in this episode, Singer’s life unfolds in ways that feel almost unbelievable—yet deeply human. From living in solitude and meditating in the woods, to being pulled into unexpected responsibilities, leadership roles, and eventually the world of software, finance, and corporate growth. At every step, his mind protests. It wants to say no. It wants control. It wants safety and predictability.And yet—he keeps letting go.If you’re anything like me, parts of this story may make you uncomfortable. There were moments while listening when I felt my own resistance show up immediately. My mind wanted to argue. To negotiate. To skip ahead. That reaction alone is part of the lesson. Singer isn’t asking us to abandon ambition or stop caring about outcomes. He’s pointing to something much subtler: the internal friction we carry when reality doesn’t match our preferences.What happens, he asks, if instead of fighting life, we work with it?Throughout the episode, we explore not just what happened to Singer, but what was happening inside him. How each unwanted situation became an opportunity to release fear. How discomfort became a teacher rather than a problem to solve. And how surrender, surprisingly, didn’t lead to passivity—but to clarity, effectiveness, and trust.This story also forces an uncomfortable question: how much of our stress comes not from what’s happening, but from our resistance to it?Singer’s journey doesn’t offer a formula to copy. It offers something more honest: an invitation to notice where we’re saying no internally, even as life continues to move forward. Whether you’re building a business, navigating uncertainty, or simply feeling worn down by the need to control outcomes, this episode gives you space to pause and reflect.At its heart, this is a deeply human story about learning to live with less inner conflict—and discovering that when you stop pushing against life, life often meets you with unexpected generosity.If this episode resonates, you’re not alone. That quiet recognition—the sense that someone has put words to something you’ve felt but never named—is exactly what Deeply Driven is about.Deeply Driven Books (Amazon Affiliate) - 100% of commissions will be donated to help support Children’s Literacy!https://amzn.to/45R6rxCMichael Singer Interview with OprahThe Untethered Soul: The Journey Beyond YourselfPast Episodes Mentioned#1 Henry Ford My Life and Work (What I Learned)Kent Taylor and his Texas Roadhouse Dream#16 How Jim Casey Turned Service Into UPS's SuperpowerEstée Lauder: Divine Purpose of Beauty#22 Leonard Lauder: The Power of Small Details If you enjoyed this episode, please leave us a review. It would greatly help the show and we thank you in advance for all your tremendous support. Deeply Driven NewsletterWelcome! Deeply Driven WebsiteDeeply Driven XDeeply Driven (@DeeplyDrivenOne) / X Substackhttps://larryslearning.substack.com/ Thanks for listening friends!
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    1 hr and 14 mins
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