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
<ul>
 <li>Join Clay and a select group of passionate value investors for a retreat in Big Sky, Montana. Learn more <a href="https://www.theinvestorspodcast.com/summit/">⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠</a>.
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 <li>Join the exclusive <a href="https://www.theinvestorspodcast.com/mastermind-2/">⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Mastermind Community⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠</a> to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.</li>
 <li>Derek’s fund: <a href="https://www.gatorcapital.com/">Gator Capital</a>.</li>
 <li>Derek’s <a href="https://www.gatorcapital.com/research-request-access">letters</a>.</li>
 <li>Related Episode: <a href="https://link.chtbl.com/WSB669">TIP669: Quietly Compounding at 20%+ Per Year w/ Derek Pilecki</a>.</li>
 <li>Follow Derek on <a href="https://x.com/gatorcapital?lang=en">X</a>.</li>
 <li>Follow Clay on <a href="https://www.linkedin.com/in/clay-finck-8073a8a7/">⁠LinkedIn⁠</a> & <a href="https://twitter.com/Clay_Finck">⁠X⁠</a>.</li>
 <li>Related <a href="https://prodcast.io/collections/we-study-billionaires-the-investor-s-podcast-network">⁠books⁠</a> mentioned in the podcast.</li>
 <li>Ad-free episodes on our <a href="https://premium.theinvestorspodcast.com/">⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Premium Feed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠</a>.
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