This week’s conversation is with Paul Assaiante, one of the most decorated coaches in college sports history.

For those unfamiliar, Paul is a legend – he is a two-time Olympic coach of the year, the “winningest coach in college sports history”, an inductee of the U.S. Squash Hall of Fame, and has won 17 NCAA championship titles at Trinity College where he is still the head coach of the Men’s Squash team today.

You might also recognize Paul’s name from his first appearance on Finding Mastery back in 2016 – that’s episode #47 if you want to check it out.

Paul has spent more than four decades coaching, motivating, and mentoring top athletes from around the world – and with how rapidly our culture is shifting, I was excited to have him back on to explore some of the changes he has observed over the last several years.

The wisdom Paul displays is abundant, and I hope you’ll find as much value in this conversation as I did. We discuss how to prepare our children to succeed in a competitive world, the importance of failure, what it really means to win, and so much more.

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Bonus: A Decade of Lies, Coverups, and Disasters at Boeing