Adidas and Puma aren’t just competitors; they’re the result of one of the most intense sibling rivalries in business history.

Join us in this episode to learn more

In this special end-of-year episode, we take a step back to reflect on the journey so far: the ideas that challenged us, the entrepreneurs across eras who inspired us, the debates that sharpened our thinking, and the listeners who showed up week after week to engage with the questions that matter.

We also share an update on Alika, the startup we’ve been building alongside the podcast. Check it out here

In this episode of Entrepreneur Head to Head, we put two entrepreneurs from radically different eras face to face: Madam C.J. Walker, America’s first self-made female millionaire, and MrBeast, the modern king of the attention economy.

We break down how Walker built a beauty empire from necessity in early 20th century America overcoming segregation, lack of capital, and systemic barriers while MrBeast engineered virality in the digital age, turning attention into one of the largest independent media businesses in the world.

What if the most honest source of truth… wasn’t the news but the market?

In this episode of Entrepreneur Head to Head, we break down the rise of Shayne Coplan, the founder behind Polymarket the platform where people don’t just argue about the future… they put money on it.

We explore:

• How Polymarket turned prediction into a product

• Why financial incentives beat opinions when it comes to truth

• The philosophy behind markets as information engines

• The legal battles, risks, and controversies around “betting on reality”

• What Coplan’s story teaches about building in chaos and thinking against the system

This isn’t just a startup story it’s about power, probability, and a future where markets may matter more than media.

If you’ve ever wondered whether the crowd is smarter than the experts this episode has your answer.

In this special episode of Entrepreneur Head to Head, we step away from our usual matchups to reflect on a defining moment in business history Warren Buffett’s final letter to Berkshire Hathaway shareholders and his decision to step down as CEO.

Tune in as we celebrate The Oracle of Omaha and explore the content of his final shareholder letter and what his exit means for the future of Berkshire and the world of business.

In this heartfelt finale, we reflect on what we’ve learned, the conversations that surprised us, and the growth that came with every episode. It’s a moment to appreciate how far we’ve come, and to say thank you before we dive into what’s next.

Because gratitude isn’t just good energy — it’s the real currency of any great journey

In this explosive episode of Entrepreneur Head-to-Head, we pit two of the most mysterious empire builders in history against each other — Pablo Escobar, the Cartel King who ruled with cash and fear, versus Satoshi Nakamoto, the Crypto Ghost who redefined money without ever showing his face.

We dive deep into their rise, their methods, and their legacies — one built an empire of smuggling routes and loyalty, the other an invisible economy of code and decentralization. Then we flip the script: what if Escobar had Bitcoin, and what if Satoshi had to survive the chaos of 1980s Colombia?

Raw ambition meets pure innovation in a debate that blurs the line between outlaw and visionary.

What happens when a queen of the Nile meets the queen of daytime TV?
In this episode of Entrepreneur Head-to-Head, we pit ancient Egypt’s master strategist Cleopatra against modern media mogul Oprah Winfrey. We explore how Oprah’s brand-building genius, media empire instincts, and philanthropic drive might have reshaped the ancient world—and how Cleopatra’s political power plays compare to Oprah’s global influence.
Tune in for an era-swapping debate on leadership, wealth creation, and the timeless DNA of an entrepreneur.

Step into the ultimate clash of creative geniuses as we pit Renaissance polymath Leonardo da Vinci against modern tech icon Steve Jobs. In this episode, we explore how each reshaped their worlds through relentless innovation—Leonardo with his groundbreaking inventions and art, Jobs with his revolutionary products and design philosophy.

🚗✨📦 What happens when the king of assembly lines faces off against the master of online primes? In this episode, we pit Henry Ford against Jeff Bezos in a head-to-head battle of entrepreneurial greatness.

We explore:

• How each built empires that reshaped everyday life

• The brilliance (and controversies) behind their ventures

• The obstacles they overcame in their rise to dominance

• And the big question: if their eras were reversed, could they still thrive?