Billionaire Biographies

Episode 90 - Elizabeth Holmes: The Blood Unicorn of Silicon Valley

Elizabeth Holmes was hailed as the "next Steve Jobs," a visionary who promised to revolutionize healthcare with a device that could run hundreds of medical tests on a single drop of blood. This episode tells the story of Theranos, the company she founded, and the massive, multi-billion-dollar fraud she perpetrated. We trace her journey as a Stanford dropout who, with her distinctive black turtleneck and deep voice, captivated investors, board members, and the media.
We expose the shocking truth that lay behind the hype: the technology never worked. We take you inside the company's culture of secrecy, fear, and intimidation, which silenced employees who tried to speak out about the fraud. We follow the courageous reporting of Wall Street Journal journalist John Carreyrou, whose investigation finally exposed the lie, revealing that Theranos was secretly running its tests on commercially available machines from its competitors. The story is a stunning account of deception on a grand scale.
The downfall of Elizabeth Holmes and Theranos is one of the most dramatic stories of corporate fraud in American history. It is a powerful lesson in the dangers of Silicon Valley's "fake it till you make it" culture. Her story reveals how a compelling vision, in the absence of a real product, can become a dangerous and destructive lie.

Episode 91 - Travis Kalanick and the Toxic Culture of Uber

Uber was one of the fastest-growing and most disruptive startups in history, a company that waged war on the taxi industry and changed how we move through cities. This episode tells the story of its co-founder and former CEO, the brilliant but deeply controversial Travis Kalanick. We explore the aggressive, "win-at-all-costs" mentality that he instilled in the company, a philosophy that prioritized growth above all else, including, at times, the law.
We delve into the series of scandals that defined Kalanick's tenure and exposed the company's toxic "bro culture." These included allegations of rampant sexual harassment, the use of a secret software tool called "Greyball" to deceive law enforcement, and a confrontational corporate style that alienated regulators, drivers, and the public. The crisis reached a boiling point after a former engineer, Susan Fowler, published a blog post detailing the company's dysfunctional and misogynistic environment, sparking an internal investigation and a shareholder revolt.
The story culminates in Travis Kalanick's dramatic ouster from the company he had built into a global powerhouse. His saga is a defining case study of the modern tech world, asking a critical question: can a company succeed at the highest level without a moral compass? Kalanick built an empire, but the culture he created ultimately became its greatest liability.

Episode 92 - Martin Shkreli: The Pharma Bro We Loved to Hate

In 2015, a smirking hedge fund manager named Martin Shkreli became the most hated man in America. This episode tells the story of the infamous "Pharma Bro," who sparked a national outrage when his company acquired the rights to a life-saving drug, Daraprim, and immediately raised its price by over 5,000%, from $13.50 to $750 a pill. We explore the unapologetic greed and the troll-like public persona that Shkreli adopted in the face of widespread condemnation.
We analyze the business model of a man who saw life-saving medicine not as a public good, but as an undervalued asset whose price could be ruthlessly maximized for profit. But the story takes a turn when we reveal that it wasn't his price-gouging that brought him down. We follow the separate federal investigation into securities fraud from his previous hedge funds, a case that ultimately led to his conviction and imprisonment. Throughout it all, he used social media and live streaming to taunt his critics and cultivate a bizarre following.
Martin Shkreli’s story is a grotesque caricature of capitalism at its worst. He is a symbol of a system where immense profits can be made from the suffering of others. His case forced a national conversation about drug pricing and the ethics of the pharmaceutical industry itself.

Episode 93 - The Arms Dealers: Adnan Khashoggi and Viktor Bout

While some billionaires build empires, others profit from their destruction. This episode enters the shadowy world of international arms dealing, focusing on two of its most notorious figures: Adnan Khashoggi and Viktor Bout. We first profile Khashoggi, the lavish Saudi arms dealer of the 1970s and 80s who brokered massive weapons deals between the United States and the Saudi monarchy, living a life of unimaginable opulence and becoming a central figure in the Iran-Contra affair.
We then descend into the post-Cold War chaos to tell the story of Viktor Bout, the Russian ex-military officer known as the "Merchant of Death." We reveal how Bout used a fleet of aging Soviet cargo planes to transport weapons to war zones across Africa, Asia, and South America, fueling brutal civil wars and arming some of the world's most violent regimes and terrorist groups. His story culminates in a dramatic DEA sting operation in Thailand that led to his capture and eventual imprisonment in the United States.
These are the merchants of death, the men who turned conflict into a multi-billion-dollar business. Their stories expose the dark, unregulated underbelly of global politics, a world where fortunes are made by fueling humanity's most violent impulses. They are the ultimate profiteers of war.

Episode 94 - The Casino Kings: Sheldon Adelson and Steve Wynn

The casino industry creates billionaires who wield a unique and potent form of political power. This episode focuses on the two titans who transformed Las Vegas and Macau and used their fortunes to become kingmakers in American politics: Sheldon Adelson and Steve Wynn. We explore how Adelson, the founder of Las Vegas Sands, revolutionized the industry with his focus on conventions and his massive expansion into Asia, becoming one of the largest donors to the Republican party, single-handedly financing political campaigns with his immense wealth.
We then turn to Steve Wynn, the visionary who created the modern Las Vegas mega-resort with properties like The Mirage and the Bellagio. He was seen as the elegant, artistic face of the industry until a devastating 2018 report detailed a decades-long pattern of sexual misconduct and abuse against his female employees. The scandal exposed a dark side to the glamour of his empire and led to his complete downfall and resignation from the company that bore his name.
The stories of Adelson and Wynn reveal the immense power that flows from the casino floor into the halls of government. They show how fortunes built on gambling can be used to shape public policy and how the industry's glittering facade can hide a much darker reality. They were the kings of a world of high stakes and deep secrets.

Episode 95 - Legacy and Lies: Is Great Wealth Ever Clean?

After ninety-four episodes exploring the lives of billionaires, we pause to ask a fundamental question: is it possible for any great fortune to be truly "clean"? This special thematic episode examines the concept of "primitive accumulation," the idea that behind every massive fortune lies a great crime, a forgotten injustice, or a hidden exploitation. We revisit the stories from our series, connecting the dots between the different eras of wealth creation.
We draw a line from the monopolistic practices of John D. Rockefeller and the violent union-busting of Andrew Carnegie to the crony capitalism of the Russian oligarchs and the exploitative labor conditions at modern retail and tech giants. We explore the hidden costs, externalities, and societal consequences that are rarely accounted for on a billionaire's balance sheet. From the slave labor that built early American fortunes to the environmental damage caused by industrial empires, wealth is rarely created in a vacuum.
This episode is a critical reflection on the very nature of capitalism and the moral compromises that seem inherent in the pursuit of extreme wealth. We challenge the "self-made" myth and ask our listeners to consider the systems, sacrifices, and sins that are baked into the foundations of the world's greatest fortunes. This is the balance sheet they don't want you to see.

Episode 96 - Oprah Winfrey: From Talk Show Host to Media Empress

Oprah Winfrey’s story is one of the most remarkable and inspiring in modern American history. This episode chronicles her journey from a childhood of poverty and trauma to becoming the queen of daytime television and the first Black female billionaire in America. We explore the revolutionary impact of The Oprah Winfrey Show, which transformed the talk show format from a spectacle of conflict into a platform for empathy, self-improvement, and authentic connection.
We then analyze her brilliant transition from a television host into a full-fledged media mogul. We dissect the creation of her empire, which includes her own production company, Harpo Studios, O, The Oprah Magazine, and the Oprah Winfrey Network (OWN). She didn't just build a brand; she built a deep, personal, and trusted relationship with her audience, which she then leveraged into a multi-billion-dollar business. Her recommendation could create a best-selling author overnight, a phenomenon known as the "Oprah Effect."
Oprah's story represents a different model of wealth creation, one built on authenticity and emotional connection rather than ruthless consolidation or financial engineering. She proved that a fortune could be made by empowering an audience, not just by selling to it. She is the undisputed empress of a media kingdom she built in her own image.

Episode 97 - MacKenzie Scott: The Philanthropist Who is Giving It All Away

In 2019, MacKenzie Scott's divorce from Jeff Bezos left her with a fortune of over $35 billion, making her one of the richest women in the world. This episode tells the story of what she did next, embarking on one of the most rapid and revolutionary philanthropic sprees in history. We explore her decision to sign the Giving Pledge and her commitment to give away the majority of her wealth "until the safe is empty."
We analyze her unique and disruptive approach to philanthropy. Instead of creating a large, bureaucratic foundation in her own name, she and her team quietly research and identify non-profits and then give them massive, unrestricted grants with no strings attached. This model shows a deep trust in community-led organizations and stands in stark contrast to the top-down, metric-obsessed approach of many other mega-donors. In just a few years, she has given away billions of dollars, more than most foundations give in a decade.
MacKenzie Scott's story is a direct challenge to the very nature of modern philanthropy. Her actions force a critical conversation about the role of billionaires in society and the responsibilities that come with extreme wealth. She is not just giving away money; she is trying to give away power.

Episode 98 - Sara Blakely and the Rise of Spanx

In the late 1990s, Sara Blakely, a fax machine salesperson, had an idea for a new kind of undergarment but only $5,000 in savings to her name. This episode tells the incredible story of how she turned that idea into Spanx, a billion-dollar global brand, without ever taking a dime of outside investment. We follow her scrappy, relentless journey as she navigated the male-dominated worlds of manufacturing and venture capital, facing constant rejection but refusing to give up on her vision.
We explore her unconventional and brilliant approach to marketing and branding. From using her own friends as models to her big break on The Oprah Winfrey Show, Blakely built her company through authentic storytelling and a deep connection with her customers. Her success made her the youngest self-made female billionaire in the world and a new icon of female entrepreneurship. She proved that a massive company could be built by solving a real-world problem that established players had ignored.
Sara Blakely's story is an inspiring tale of grit, creativity, and perseverance. It represents a new model for building a billion-dollar business, one that prioritizes organic growth and profitability over the venture-backed, "growth-at-all-costs" mindset. She didn't just build a company; she built it on her own terms.

Episode 99 - The Crypto Billionaires: The Boom and Bust of a New Asset Class

The rise of cryptocurrencies created a new, wild-west frontier of wealth, minting a generation of overnight, digital-native billionaires. This episode dives into the volatile world of crypto, focusing on some of its most prominent and controversial figures. We profile Changpeng Zhao ("CZ"), the founder of the world's largest crypto exchange, Binance, who built a massive, unregulated financial empire before facing intense scrutiny and legal trouble from governments around the world.
The centerpiece of our story is the spectacular rise and catastrophic fall of Sam Bankman-Fried (SBF), the wunderkind founder of the exchange FTX. We explore how SBF became the friendly, public face of the crypto industry, attracting billions in investment and celebrity endorsements, all while secretly funneling customer funds to his own private hedge fund. We then chronicle the stunning collapse of his empire in a matter of days, exposing one of the largest financial frauds in recent history and wiping out billions of dollars in wealth.
The story of the crypto billionaires is a cautionary tale of hype, greed, and the dangers of an unregulated market. It captures the dizzying boom and the devastating bust of a new technological gold rush. Their fortunes were built on a new kind of asset, but their downfall was a classic story of old-fashioned fraud.