Managing Company-Level Leverage Risk

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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