We Study Billionaires - The Investor’s Podcast Network TIP758: Current Market Conditions & Investment Opportunities w/ Derek Pilecki
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Oct 3, 2025 
Join Derek Pilecki, a seasoned portfolio manager at Gator Capital Management, as he delves into the intricacies of today's investment landscape. He shares his strategy for targeting a potential 26% IRR and the impact of recent financial turmoil, including the 2023 bank failures. Discover his insights on evolving value investing, opportunities in regional banks and fintech, and how interest rate cuts could shape the economy. Derek also discusses his view on Robinhood's turnaround and offers a compelling investment thesis for WEX Inc.
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Target Double-In-Three-Years
- Derek targets ideas that can double in ~3 years to focus capital where asymmetric returns exist.
- He avoids tying up capital in positions expected to only earn small returns.
Combine Fundamentals With Momentum
- Use both fundamental analysis and technicals by waiting for a chart base before adding to positions.
- Let winners run instead of selling fully at initial price targets to capture momentum gains.
Tariff Tantrum Active Moves
- During the tariff scare Derek quickly covered many regional-bank shorts and increased long exposure as valuations plunged.
- He called the two-day regional bank selloff a stressful opportunity where quick decisions materially affected performance.
