TIP669: Quietly Compounding at 20%+ Per Year w/ Derek Pilecki

On today’s episode, Clay is joined by Derek Pilecki.

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 21.0% per annum versus 11.8% for the S&P 500 over the same time period.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro

01:48 - Derek’s experience of launching a financials-focused fund 10 weeks before the collapse of Lehman Brothers.

12:13 - Derek’s advice to aspiring hedge fund managers.

14:30 - How Derek achieved a return of 186% in 2009.

14:30 - What led Derek to purchase General Growth Properties, whose stock increased by 20x in less than one year.

23:25 - Why Warren Buffett likes financial companies, especially the big banks.

27:38 - Why Derek puts his focus on financial companies.

33:36 - How banks can create a sustainable competitive advantage in their market.

36:08 - Why First Citizens Bancshares is Derek’s top position in his fund.

46:44 - An update on the current market conditions for banks.

50:21 - How a high inflation environment would impact banks.

52:53 - Why Derek is long Robinhood.

And so much more!

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: Listen to TIP634: Value Investing Fundametals w/ John Huber, or watch the video.
• Follow Derek on Twitter.
• Follow Clay on Twitter.
• Check out all the books mentioned and discussed in our podcast episodes here.
• Enjoy ad-free episodes when you subscribe to our Premium Feed.

NEW TO THE SHOW?

• Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok.
• Check out our We Study Billionaires Starter Packs.
• Browse through all our episodes (complete with transcripts) here.
• Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool.
• Enjoy exclusive perks from our favorite Apps and Services.
• Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets.
• Learn how to better start, manage, and grow your business with the best business podcasts.

SPONSORS

Support our free podcast by supporting our sponsors:

• River
• Toyota
• Connect Invest
• TastyTrade
• The Bitcoin Way
• P...