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 7-Eleven Toyota Connect Invest Miro TastyTrade Daloopa The Bitcoin Way Facet Public Fidelity Fundrise Onramp SimpleMining Bluehost ReMarkable Vanta Shopify HELP US OUT! Help us reach new listeners by leaving us a rating and review on Spotify! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm