TIP758: CURRENT MARKET CONDITIONS & INVESTMENT OPPORTUNITIES

W/ DEREK PILECKI

TIP758: CURRENT MARKET CONDITIONS & INVESTMENT OPPORTUNITIES W/ DEREK PILECKI

02 October 2025

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.

SUBSCRIBE

IN THIS EPISODE, YOU’LL LEARN:

  • Derek’s process of looking for a potential 26% IRR on new investments.
  • How value investing has evolved over the tenure of running his fund.
  • The moves he made during the tariff tantrum earlier this year.
  • How Buffett has influenced him as an investor.
  • The opportunities he’s finding in the market today.
  • How he expects the Fed’s interest rate cuts to impact the economy, the banking sector, and the real estate market.
  • What Derek saw in Robinhood’s stock before it increased by over 10x.
  • Derek’s investment thesis in WEX Inc.
  • And so much more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

[00:00:00] Clay Finck: On today’s episode, we welcome back Derek Palecki. Derek is our favorite guest to discuss all things financials as he’s the portfolio manager at Gator Capital Management. He launched Gator Capital Weeks before the collapse of Lehman Brothers in 2008, and he has one of the best investment track records I’ve ever come across.

[00:00:18] Clay Finck: Since the fund’s inception in July of 2008, Gator Capital has compounded at 21.8% per year versus just 11.9% for the S&P 500 over that same time period. During this conversation, we discussed Derek’s process of looking for a potential 26% internal rate of return on new investments in the fund, the moves he made during the tariff tantrum earlier this year.

[00:00:41] Clay Finck: How Warren Buffett influenced his own investment process, the opportunities he’s finding in today’s market, how he expects the Fed’s interest rate, cuts to impact the economy, the banking sector, and the real estate market. What Derek saw in Robinhood stock in November of 2023 before it increased by over 13 times.

[00:00:59] Clay Finck: Derrick’s investment thesis in WEX, Inc. And so much more. Also, Derrick will be joining our mastermind community for Q&A a few weeks after this episode goes live. If you’re interested in sitting in on that discussion, you can join the wait list for the group using the link in the description. It’s always a treat to bring Derrick on the show as he knows the financial sector as well as anyone.

[00:01:19] Clay Finck: So with that, I hope you enjoy today’s discussion with Derek Palecki.

[00:01:27] Intro: Since 2014, and through more than 180 million downloads, we’ve studied the financial markets and read the books that influenced self-made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host, Clay Finck.

[00:01:51] Clay Finck: Welcome to The Investor’s Podcast. I’m your host, Clay Finck, and today I am happy to welcome back, Derek Pelecki. Derek, welcome back to the show.

[00:01:59] Derek Pilecki: Hey, Clay, good to see you. Thanks for having me back.

[00:02:03] Clay Finck: So I’ve really been looking forward to this conversation as I definitely enjoyed our last discussion about a year ago where you shared your humble beginnings of launching a fund all the way back in 2008, just weeks before the collapse of Lehman Brothers.

[00:02:17] Clay Finck: Since we last spoke, you rounded out 2024 with a 41% return net of fees, and through July of this year, you are up another 21%. So it’s looking like you’re well positioned to have three years in a row of really strong performance and. You know, that can even tend to be bad news for all of us because usually after a few good years, you tend to see a down year across the entire market.

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