Journal Entry: Michael Santos-Onassis

Journal Entry

My wife, Carole, and I spend a lot of time driving together, and I often pass the time by listening to audiobooks. Recently, she mentioned needing a break from the “business” books I usually pick. To mix things up, I suggested a biography on Aristotle Onassis. While a successful business leader, he was also known for his vibrant personality, captivating storytelling, and relentless drive. Carole agreed, so I found a biography on his life and downloaded it for our next drive.

Why I Chose to Read the Book

I always appreciate opportunities to learn from people who were great innovators. While listening to another biography, the author referenced Aristotle Onassis, the Greek shipping magnate. His name came up alongside other titans of business who rose from humble beginnings. That mention sparked my curiosity. Since I enjoy reading about self-made business leaders, I searched for a biography on Onassis. I found Onassis by Frank Brady and downloaded the audio version so I could listen while continuing with my daily work and exercise.

I chose this book because I wanted to learn how Onassis built an empire from nothing. I’ve always believed that adversity doesn’t have to define a person—it can shape resilience. Onassis was an immigrant, an outsider in many ways, and yet he maneuvered his way into elite circles of influence and wealth. That kind of transformation aligned closely with the values I teach—using strategy, grit, and vision to overcome the odds.

What I Learned from Reading the Book

From Onassis, I learned that Aristotle Onassis was far more than just a shipping magnate—he was a master of image, negotiation, and timing. Some key takeaways include:

  • Start with What You Have: Onassis began his business journey selling tobacco in Argentina. He leveraged relationships, listened carefully, and made calculated risks to expand into shipping.
  • Think Globally: He didn’t confine his thinking to Greece or Argentina. Onassis mastered international markets. He forged relationships with governments, banks, and powerful figures worldwide—often thinking steps ahead of competitors. He also learned how to speak the local language.

  • Play the Long Game: Onassis bought aging ships when others thought they were worthless, fixed them, and made huge profits during global shipping shortages. He understood cycles and positioned himself accordingly.
  • Use Influence Strategically: He wasn’t just rich—he was also connected. Marrying Jacqueline Kennedy and courting global leaders like Winston Churchill showed how he used personal branding and proximity to power as a business asset.
  • Resilience and Rebound: Despite scandals, personal losses, and massive financial risks, Onassis always found a way to bounce back. He made bold plays when others were too afraid to act.

How This Book Will Contribute to My Pursuit of Excellence and Success

The life and mindset of Aristotle Onassis align with my core belief that anyone—regardless of background—can rise if they adopt the right strategy, build relationships, and stay committed to progress.

From Onassis, I learned lessons I can apply in my own work building the Prison Professors platform and nonprofit:

  • Leverage every opportunity: Just as Onassis found value in what others overlooked, I find value in overlooked populations—like people in prison. By investing in them, we create second chances and unlock potential.
  • Use relationships with intention: Onassis didn’t shy away from building high-level connections. Similarly, I seek out partnerships with business leaders, institutions, and media to advance the mission of justice reform and reentry preparation.
  • Tell a compelling story: Onassis understood that perception matters. I’ve learned to share my journey publicly—books, videos, speaking engagements—not to boast, but to prove that transformation is possible and credible.
  • Adapt constantly: Onassis thrived by reading global trends. I aim to do the same with shifts in technology (like AI and blockchain), justice reform, and education so that I can better serve my audience.

This biography reminded me that success requires a person to be resourceful, strategic, and resilient. Onassis made many controversial decisions, but his drive to rise taught me that no goal is too big if we remain intentional with our time, relationships, and execution.

Self-Directed Question:

  • What strengths or hidden assets do you currently have that others may overlook—and how can you use them to create opportunities for success, no matter your circumstances?