Deeply Driven: Business History Insights from Entrepreneurs

In a world where most CEOs wore suits and spoke in corporate jargon, Herb Kelleher showed up in a t-shirt, laughed loudly, and built one of the most successful airlines in history by doing everything the “experts” said was crazy.

This episode explores the remarkable story of Herb Kelleher, the legendary co-founder and longtime CEO of Southwest Airlines, and how his unconventional leadership reshaped the airline industry—and American business itself.

When Kelleher and his small team set out to launch Southwest in the early 1970s, they didn’t have the money, planes, or political backing...

In the world of business history, few stories shine as brightly - or as humbly - as that of Sam Walton, the small-town merchant who changed how America shops. From a single five-and-dime store in rural Arkansas, Walton built one of the largest companies in history, not through flash or fortune, but through ideas that were both simple and deep.

This episode of Deeply Driven explores the life and lessons of the man behind Walmart, his journey from hardship to abundance, and the timeless rules he left behind for every entrepreneur who dreams of building something that...

In the world of business history, few figures stand as tall as Sol Price, the pioneering entrepreneur whose quiet but revolutionary ideas reshaped the way millions of people shop. If you’ve ever walked the aisles of Costco, Sam’s Club, or Price Club, you’ve experienced his legacy firsthand. Yet despite building the foundation for an entire retail model, Price often avoided the spotlight. His story, found in the biography Sol Price: Retail Revolutionary and Social Innovator, is less about fame and more about principles, discipline, and an unshakable belief that business should serve both customers and employees.

B...

This is the story of Kent Taylor and his Texas Roadhouse Dream, as we dive in and explore entrepreneurial lessons that will fuel our growth. Kent's journey shows how “crazy” ideas can build billion-dollar companies when fueled by grit and heart. Born in 1955, Taylor wasn’t the most gifted athlete or student, but he quickly learned that outworking others was his secret weapon. As a teenager, he logged over 1,500 miles one summer to improve as a runner, teaching himself to push through pain and reshape his destiny. That relentless drive carried into his career, where rejection became a steppingstone, after...

In this episode, we step into the world of Fred Rogers, the gentle force behind Mister Rogers’ Neighborhood. Known to generations of children as simply Mr. Rogers, his influence reached far beyond television screens. What made him remarkable wasn’t wealth, scale, or corporate success, but his deeply driven purpose: to nurture kindness, honesty, and emotional wellbeing in every child he encountered.

Fred’s story begins in Latrobe, Pennsylvania, where he grew up in privilege but also isolation. Teased as “Fat Freddy,” he often retreated to his attic, creating puppet shows for himself and pouring his feelings into the p...

In this episode we dive into the extraordinary life of Sam Zemurray, the "Banana Man," as chronicled in Rich Cohen's The Fish That Ate the Whale. From arriving penniless in America at age 14 to orchestrating a coup in Honduras and taking over United Fruit, the world's largest banana empire. Zemurray's story is a masterclass in grit, innovation, and knowing your business "from A to Z." We explore how he turned discarded "ripes" into a fortune, outmaneuvered giants like United Fruit, and staged one of history's boldest corporate takeovers. Packed with lessons on risk-taking, hands-on leadership, and ethical gray zones...

In this episode we focus on Walter Isaacson's gripping biography, Elon Musk, a 600+ page exploration of the visionary entrepreneur's life and relentless drive. Drawing from Musk's childhood in South Africa to his groundbreaking ventures, the episode highlights key lessons on innovation, leadership, and resilience that any business owner can apply.

Early Life and Formative Influences

Born in 1971 in Pretoria, South Africa, Musk endured a tough upbringing marked by bullying at school and emotional abuse from his father, Errol. These experiences forged his "emotional shutoff valve," turning him into a bold risk-taker who thrives on chaos...

In this episode, we dive deep into the raw, high-stakes early years of SpaceX—a story of vision, grit, and a team willing to bet everything on an almost impossible dream. Drawn from Eric Berger’s Liftoff and enriched with reflections on leadership, hiring, and risk-taking, we relive the rollercoaster journey that took Elon Musk from an idea on the Long Island Expressway to the first privately developed rocket reaching orbit.

This is not the story of a billionaire tinkering with a vanity project. It’s the story of a man who risked half his PayPal fortune, faced...

This episode explores the fascinating, multi-generational story of the Mars family and their journey to building one of the most iconic candy companies in the world. It begins with Frank Mars, who, as a young boy stricken with polio, spent much of his time indoors watching his mother make candies and baked goods. This early exposure ignited his passion for candy making, which would become his life’s work. Despite his love for the craft, Frank’s early business ventures were marked by repeated failures—he endured three bankrupt candy operations, losing everything each time. Yet his perseverance never wavere...

Welcome to this special bonus episode of Deeply Driven, today we profile that of William Murrie, the longtime president of Hershey’s.

Before Hershey’s became a household name and one of America’s most iconic chocolate companies, it needed someone who could turn Milton Hershey’s visionary ideas into reality. That man was William Murrie.

A former telegraph operator, semi-pro baseball player, and traveling candy salesman, Murrie first crossed paths with Milton Hershey in a Lancaster billiards hall. With charm and confidence, he famously boasted he could sell more chocolate than Hershey could manufacture. Hershey...

Discover the remarkable story of Milton Hershey, the man who built America’s chocolate empire. Born in 1857 in rural Pennsylvania, Hershey faced a tough childhood and repeated business failures. At 19, he started his first candy venture, but setbacks, partly due to his father’s impractical schemes, tested his resolve. His perseverance paid off when a banker, impressed by his honesty, supported him in completing a crucial caramel order, laying the foundation for his success.

Hershey’s big breakthrough came with milk chocolate. In 1900, after selling his caramel business for $1 million, he developed a distinctive recipe that won over A...

Jay Gould was one of the most controversial and influential figures of America’s Gilded Age. Often labeled a “robber baron,” Gould built a massive fortune through relentless focus, calculated risk-taking, and often ruthless business tactics. His life represents both the possibilities and perils of unchecked capitalism in a rapidly industrializing America.

Born in 1836 in upstate New York, Gould came from modest means and was largely self-educated. His early ventures included work as a surveyor and mapmaker before entering the tannery business. It was there that his innate financial acumen began to shine. He structured deals creatively, reinve...

In this episode, we dive into the incredible story of Joe Coulombe, the visionary founder of Trader Joe’s—an entrepreneur who built a cult-like brand by doing business his own way. With no retail experience and very little capital, Joe took a chance on a small chain called Pronto Markets and transformed it into something legendary.

Faced with giants like 7-Eleven and shifting market forces, Joe pivoted by building Trader Joe’s on four foundational principles: a reasonable strategy, high employee wages, product discontinuity, and serving the overeducated and underpaid. He believed in paying people well and tr...

In this episode, we dive deep into the remarkable life and mind of Edward O. Thorp, the mathematician, investor, and author behind the classic autobiography A Man for All Markets. Thorp’s story reads like a financial thriller—complete with wearable computers, Las Vegas takedowns, Wall Street innovation, and a lifetime of thinking independently against the grain.

From his earliest memories during the Great Depression, Thorp displayed traits that would shape his career: intellectual curiosity, self-reliance, and an unrelenting drive to test conventional wisdom. As a boy, he taught himself math and science, created at home laboratories, and...

Today I would like to share with you what I learned by reading My Life and Work by Henry Ford. This book is packed full of valuable lessons in business. Documenting Ford’s journey from a young man through the duration of his career.

Henry Ford was a pioneer in the automobile industry! Along the way we see a young man who was deeply driven to teach himself about the gasoline engine and build his first car. We would have early struggles in business, with two failed automobile companies.

One Ford discovers his love of 100% co...

Welcome to Deeply Driven — a biweekly podcast where we explore the lives of purpose-filled entrepreneurs who built lasting value by following their passions. I'm Larry, and each episode is a chance for us to learn from iconic leaders like Henry Ford, Oprah Winfrey, Elon Musk, Steve Jobs, Estee Lauder, Warren Buffett, and more.

I’ve always been drawn to those who discovered their calling and turned it into something extraordinary. Through biographies and autobiographies, we’ll unpack their journeys—how they hired great people, prioritized long-term growth, focused on service, bounced back from setbacks, and never stopped learning...