Deeply Driven

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

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/45R6rxCBig Shots Interviews with Issy SharpHow 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 MentionedEstée Lauder: Divine Purpose of BeautyE18 Harry Snyder: In-N-Out and the Power of “Keep It Real Simple”#16 How Jim Casey Turned Service Into UPS's SuperpowerSam 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 NewsletterWelcome! Deeply Driven WebsiteDeeply Driven XDeeply Driven (@DeeplyDrivenOne) / X Substackhttps://larryslearning.substack.com/ Thanks for listening friends!

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

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 DreamSam Walton: Simple Ideas & Deep Business Impacts#16 How Jim Casey Turned Service Into UPS's SuperpowerE18 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 NewsletterWelcome! Deeply Driven WebsiteDeeply Driven XDeeply Driven (@DeeplyDrivenOne) / X Substackhttps://larryslearning.substack.com/ Thanks for listening friends!

#23 Michael A. Singer: Saying Yes to Life & Watching Everything Change

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!

#22 Leonard Lauder: How Small Details Craft Business

Leonard Lauder grew up in a kitchen that smelled like face cream. His mother Estée cooked cosmetics on the stove while he watched. Women would ring the doorbell, get facials in the bedroom, and leave with glowing skin and a few jars in their purse. 80 years later, Leonard sits down to write his memoirs. Where does he start? That kitchen.This episode tells the story of how Leonard took his mother's small business and turned it into a global beauty empire. The book is called The Company I Keep - My Life in Beauty, and it reads like a playbook.Leonard learned business by osmosis. At six years old, he could tell which outfits suited which women. At ten, he sold military patches to classmates and put every dollar in the bank. At thirteen, he worked in the family factory after school, typing invoices for twenty-five cents an hour. He wasn't just "a" billing clerk - he was "the" billing clerk.One scene stands out. Leonard sits at a dinner table with his parents, their accountant, and their lawyer. His parents announce they want to go wholesale. The experts beg them to stop. "You'll lose everything!" But Estée and Joe push forward anyway. Their response stuck with Leonard for life: "Good accountants and lawyers make good accountants and lawyers. But we make the business decisions."The episode traces Leonard's path from that kitchen to Wharton, then to the Navy, where he learned he wasn't the smartest guy in the room. He finished 12th out of 24 in officer training. That humbled him. He made a vow: hire people smarter than yourself. The head of sales should sell better than you. The copywriter should write better copy. Never feel threatened by talent. Celebrate it.After the Navy, Leonard went skiing in Vermont. Blue sky, fresh snow. He made a choice on that slope. Estée Lauder would be his life's work. His goal? Make it the General Motors of beauty - multiple brands, multiple products, global reach.He did just that. When ad firms turned them away for not having enough money, Estée bet everything on free samples. Not tiny packets - full-size products that lasted 60 days. Women lined up down the block. When Leonard saw he'd oversold his college film club (1,500 members, 800 seats), he started a second club to compete with his first. No one knew he ran both. That lesson became Clinique - a brand built to compete against Estée Lauder itself.Leonard watched everything. He visited stores on his honeymoon. He planned family trips around counter visits. He saw a woman in China unbutton her dull coat to reveal bright red silk underneath. Hidden beauty. That's how he knew to expand into China.The episode also covers his concept of lateral creativity - taking ideas from anywhere and using them in business. An architect told him about planting young trees to replace old ones when they die. Leonard thought: we need young brands to understudy our flagship. That insight led to buying MAC and Bobbi Brown and developing an acquisition playbook.By the end of his run, Estée Lauder had 25 brands in 150 countries. But when asked what he's most proud of, Leonard doesn't talk about products or sales. He talks about mentoring people.This book belongs on the shelf next to Sam Walton and Trader Joe. It's a masterclass hidden inside a memoir.Deeply Driven Books (Amazon Affiliate) - 100% of commissions will be donated to help support Children’s Literacy!https://amzn.to/45R6rxCPast EpisodesEstée Lauder: Divine Purpose of Beauty#16 How Jim Casey Turned Service Into UPS's Superpower#3 Becoming Trader Joe | Business Masterclass from a LegendSam Walton: Simple Ideas & Deep Business Impacts 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!

E21: Arthur Guinness: Small Steps, Steady Craft, Still Here

What I learned about Arthur Guinness from Arthur’s Round is that the “legend” wasn’t built in one bold leap. It was built the way real lives are built: in small steps, taken day after day, until the steps start to stack.Arthur didn’t come from nowhere. Before he ever brewed a barrel in his own name, he was standing on family ground that had been laid for generations. You can trace real, recorded brewing know-how back through the line — all the way to William Read’s 1690 license — and you get the sense that those earlier men would’ve been damn proud. Not because the story is neat, but because it’s earned: each generation edging forward, learning, saving, and getting closer to the trade.One of the biggest quiet forces in the story is Arthur’s father, Richard. Richard becomes a strong reader and writes with a clean, careful hand, and in that world, that skill is a key. It opens doors that stay shut to men who can’t read a sign, keep accounts, or put their name on paper. Richard’s work with Dr. Price becomes a turning point, too. You can feel the family air start to shift: steadier work, more trust, more pull — the kind of change that doesn’t show up in one moment, but you can hear it in the way the story moves.And then there’s Arthur’s environment — the part you can almost smell. Arthur is born into a working malthouse. Grain, heat, yeast in the air. The daily rhythm of real work. You can picture how that sinks into a child without anyone “teaching a lesson.” More is caught than taught. The place does its work on him, hour by hour, year by year, until craft starts to feel normal — and sloppiness starts to feel wrong.When Arthur finally steps out on his own, you see how much patience it takes just to get in the game. Starting a brewery isn’t a weekend dream — it takes cash, tools, space, and nerve. The figures in the records make it plain: to get started in the mid-1750s, you’re looking at roughly £400 in capital. That’s not spare change. That’s a family backing a young man’s shot — and it’s also Arthur pushing upstream, betting on himself.The early years are not a victory lap. Even after years in business, he’s not sitting at the top of Dublin’s brewing world. Out of about forty brewers, he’s closer to the middle. The tax rolls show the gap between the biggest players and the grinders — the top paying around £4,000 a year, Arthur closer to £1,500. But here’s what matters: he keeps the brew steady. Same beer, again and again. That sameness — invisible but essential — is what builds trust. And trust is what brings repeat orders.By the time Arthur makes his long, famous lease and keeps building, you can feel the “long run” begin. This is a story about craft, grit, and the slow compounding of small choices — family ties, steady work, a true product, and the stubborn will to keep going. More than 250 years later, it’s still here: a name that holds, a pint you can lift, and proof that small steps can outlast a lifetime. 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!