IN THIS EPISODE, YOU’LL LEARN:

• What sparked Ian’s obsession with investor greatness.
• The two metrics that reveal actual investing skill.
• The track records that define good, great, and GOAT investors.
• What a jiu-jitsu legend taught Ian about mastery.
• Five core skills every top investor must develop.
• Why staying the same means falling behind.
• Hidden skills that give GOATs an unfair edge.
• Why radical self-honesty drives long-term improvement.
• The rare skill Ian leverages for outperformance.
• Offense vs. defense: applying it to your portfolio.
• And so much more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.  

[00:00:00] Kyle Grieve: Today’s guest is Ian Cassel, whose fund has outperformed the S&P 500 after fees since its inception in 2019. Now, what sets Ian apart is his position in the investing community as someone who truly wants to elevate other investors. One trait that I’ve always admired in Ian is just how broad of a thinker he is and how good he is at connecting disparate ideas.

[00:00:21] Kyle Grieve: In today’s episode, we’re going to see how Ian links golf and jiu-jitsu with one big idea, which is what separates good, great, and goat investors. Ian’s been journaling and reflecting on a variety of topics based around this theme now for years. And in this conversation, he’ll lay out his detailed thoughts.

[00:00:39] Kyle Grieve: We’ll look at the two performance metrics that every investor is judged upon, which is time and return, and why they’re the most potent performance indicators to assess skill. We’ll look at what track record qualifies you as a good, great, or goat investor as well. The initial idea for this concept was bred out of Ian’s thinking on the skills of investing.

[00:00:58] Kyle Grieve: Ian has distilled stock investing into five key skills that must be sharpened in order to succeed. The big difference between being great and being world class is just a few degrees of differences in these skills. We’ll go over some of the unique and underappreciated talents that Ian has observed from some of the goats that he’s researched, and along the way, Ian’s going to share some of the real world traps that he’s fallen through in his decades of experience in the markets.

[00:01:22] Kyle Grieve: We’ll also cover some of the unique shifts in investing strategy that he’s personally used to maintain his ability to outperform the market. Additionally, he’ll outline his thoughts on how investors need to balance both being offensive and defensive. So whether you’re a fund manager or a solo investor, whether you’re a long-term investor or a trader, this episode will push you to think harder and harder about your strengths and weaknesses and what it really takes to compound for decades.

[00:01:48] Kyle Grieve: Now let’s get into this week’s chat with Ian Cassel.

[00:01:56] Intro: Since 2014 and through more than 180 million downloads, we’ve studied the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host, Kyle Grieve.

[00:02:20] Kyle Grieve: Welcome to The Investor’s Podcast. I’m your host, Kyle Grieve, and today we welcome Ian Cassel, friend of TIP onto the show. Ian, welcome to the podcast.

[00:02:28] Ian Cassel: Hey, thanks for having me on. It’s always a pleasure.

[00:02:30] Kyle Grieve: So you’ve been a friend here of the podcast and been on multiple times, and every time you’re on here I’m always amazed at how much I get to learn from you.

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