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How to Be a Master of Controlled Chaos
Methods of Prosperity newsletter no. 114: Aristotle Onassis (1906–1975)
Sean Allen Fenn
August 21, 2025
After a certain point money is meaningless. It ceases to be the goal. The game is what counts”
Many “bootstrap” entrepreneurs rely on their own capital. Aristotle Onassis mastered the art of leveraging debt and using extensive financing. He pioneered innovative ship financing methods that revolutionized the maritime industry. Which allowed him to control a fleet valued between $100-200 million. All without having to own the ships outright through traditional means.
The lesson? Use other people’s money (OPM).
Most entrepreneurs focus on operational efficiency. Onassis was a master of controlled chaos. He prioritized gathering exclusive market intelligence and insider knowledge. Which gave him strategic advantages in deals and timing.
Information asymmetry was his competitive advantage.
“The secret of business is to know something that nobody else knows.”
Most entrepreneurs operate within single jurisdictions. Onassis created an intricate network of over 30 corporations across multiple countries. He used flags of convenience (Panama, Honduras, Liberia, Costa Rica).
What is a flag of convenience (FOC)?
It refers to the international shipping practice. This is where ship owners register their vessels in countries other than their own. They take advantage of more favorable regulations, lower costs, or reduced oversight.
Onassis built complex international corporate structure.
Onassis did this to minimize operational costs and regulatory burdens. This practice was unconventional at the time.
Aristotle Onassis, the Greek shipping magnate.
Not everyone understands that control is more important than ownership. Onassis found ways to control valuable assets without owning them. He created leverage without traditional ownership. Instead, he used mortgages, long-term charters, and complex financing arrangements. That’s how he was able to build his empire with minimal personal capital investment.
“Never ask for small loans.”
Many people are risk-averse. Onassis embraced calculated risks as fundamental to his business model. To him they’re opportunities rather than threats.
“My whole life has been a terrific gamble.”
At the time of his death in 1975, Aristotle Onassis had a net worth of approximately $500 million. Which is equivalent to about $2.3 billion when adjusted for inflation as of 2025.
“To be happy make sure you are tanned, live in expensive buildings, even if you have to stay in the cellar, go out to expensive restaurants, even if you can only afford one drink and if you have to borrow, borrow a lot.”
I like you,
– Sean Allen Fenn
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