Anthony Pompliano — investor, entrepreneur, and media powerhouse — returns four years and 228 episodes later to discuss his new book, How To Live an Extraordinary Life, a collection of 65 heartfelt letters to his two children.

At just 36, Anthony has already invested in circa 200 companies, served in Iraq with the U.S. Army, built and sold multiple businesses, and created one of the world's largest independent media platforms. You don't accomplish all that without learning a thing or two, and in this episode we dig into his hard-earned insights — from the uniting traits of the world's smartest people, to the luxury of pessimism, to why luck isn't real.

I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, "Hmm, that's interesting!", check out our Substack.

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Show Notes:

The hidden power of "I don't know"
Why Anthony started writing letters to his children
Today is practice for tomorrow
Carve your ethics in stone, but your opinions in sand
How bad positioning poisons decision-making
Are there any parts of the book Anthony no longer believes in?
What unites the smartest people in the world
Why luck isn't real
The luxury of pessimism
Power laws everywhere!
Anthony as Emperor of the World
MORE!

Books, Articles & Podcasts Mentioned:

Adventures of a Bystander; by Peter F. Drucker
The Art of Learning: An Inner Journey to Optimal Performance; by Josh Waitzkin
How Will You Measure Your Life?: A thought-provoking approach to measuring life's success; by Clayton M. Christensen, James Allworth and Karren Dillon
Rules for a Knight; by Ethan Hawke
The Rise and Fall of American Growth: The U.S. Standard of Living since the Civil War; by Robert J. Gordon
Why Writing Letters to Your Kids Is the Best Gift You Can Give Them as Adults; by Polina Pompliano
Shane Parrish on the Clear Thinking podcast
Lucky vs, Repeatable; by Morgan Housel
What Kind of Lucky Are You?; by Jim O'Shaughnessy

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