He was the son of a Toronto barber, still broke at 40 after failing at business after business. Then he bought a small-town radio station and a small-town newspaper with $200 down.

By the time he died at 82, he owned more than 200 newspapers, including The Times of London, and held the Scottish TV franchise he famously called "a license to print your own money." Today, the Thomson family is the richest family in Canada.

This is the story of Roy Thomson, and we have a lot to learn from him.

Source for this episode:

• Roy Thomson of Fleet Street by Russell Braddon

Links:

• Ambition website
• Ambition Summit on September 24th, 2026
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The greatness of Zemurray lies in the fact that he never lost faith in his ability to salvage a situation. Bad things happened to him, as bad things happen to everyone, but unlike so many, he was never tempted by failure. He never felt powerless or trapped.

He was an optimist. He stood in constant defiance. When the Secretary of State teamed up with J.P. Morgan and the Honduran government in a way contrary to Zemurray's interests, he simply changed the Honduran government. When United Fruit drew a line at the Utila River and said, "You shall not cross," he crossed anyway. When he was forbidden to build a bridge, he built a bridge but called it something else.

For every move, there is a countermove. For every disaster, there is a recovery. He never lost faith in his own agency. With his fortune fast diminishing, it was time to act.

This is the story of Sam Zemurray, and we have a lot to learn from him.

Source for this episode:

• The Fish That Ate the Whale: The Life and Times of America's Banana King by Rich Cohen

Links:

• Ambition website
• Ambition Summit
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The company she started in 1946 is today worth more than $30 billion. Her story? It's one of obsession and persistence, and one I thoroughly enjoyed reading about.

This is the story of Estée Lauder, and we have a lot to learn from her.

Source for this episode:

• Estēe: A Success Story by Estēe Lauder

Links:

• Ambition website
• Ambition Summit
• Follow Justin on Twitter
• Connect with Justin on LinkedIn