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.

Important Links:

• How To Live an Extraordinary Life
• Website
• Twitter
• The Pomp Letter
• Anthony's Previous Episode

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