Targeting a 26% IRR: Examples of Big Wins and Misses

On today’s episode, Clay is joined by Derek Pilecki to discuss the current market conditions and the investment opportunities he’s finding in today’s chaotic environment.

Derek is a managing member and portfolio manager at Gator Capital Management, which manages Financials sector long/short portfolios for private partnerships and mutual funds. Since its inception in July 2008, Gator Capital has compounded capital at 21.8% per annum versus 11.9% for the S&P 500 over the same time period.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro 04:33 - Derek’s process of looking for a potential 26% IRR on new investments. 07:43 - How value investing has evolved over the tenure of running his fund. 12:23 - The moves he made during the tariff tantrum earlier this year. 15:14 - How Buffett has influenced him as an investor. 19:51 - The opportunities he’s finding in the market today. 23:00 - How he expects the Fed’s interest rate cuts to impact the economy, the banking sector, and the real estate market. 45:25 - What Derek saw in Robinhood’s stock before it increased by over 10x. 58:24 - Derek’s investment thesis in WEX Inc.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

• Join the exclusive ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
• Derek’s fund: Gator Capital.
• Derek’s letters.
• Related Episode: TIP669: Quietly Compounding at 20%+ Per Year w/ Derek Pilecki.
• Follow Derek on X.
• Follow Clay on ⁠LinkedIn⁠ & ⁠X⁠.
• Related ⁠books⁠ mentioned in the podcast.
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