"Positions Can Be LESS Risky at Higher Prices" - Derek Pilecki on Finding Edge in Financials

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Apr 2, 2026

Derek Pilecki, founder of Gator Capital Management and specialist investor in financials, shares how he finds edge in regional banks, brokerages, insurance and info-services. He explains spotting real business change vs market noise. Topics include position sizing and adding to winners, post‑GFC underwriting dynamics, private credit tail risks, AI’s impact on valuation, and scaling concentrated portfolios.

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ANECDOTE

How Three Big Calls Fueled A 20%+ Track Record

Derek Pilecki turned big gains from several concentrated financial calls into +21% annualized returns over five years.
He cites big wins in Robinhood, Anywhere Real Estate and Societe Generale plus timely regional bank positioning after First Republic and Silicon Valley failures.

ADVICE

Add To Winners Not Losers

Avoid averaging down and prefer adding to winners; new positions typically start ~4% of the portfolio.
Pilecki buys more as the market confirms his thesis, saying positions often become less risky at higher prices.

INSIGHT

Repetition And The Post‑GFC Shift In Banking

Repetition and high volume engagement build sector-specific edge: Pilecki meets ~100–120 companies a year and attends conferences.
He argues post-GFC regulation and scarred management teams have fundamentally altered bank underwriting cycles.

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In this episode of Odds on Open, Ethan Kho sits down with Derek Pilecki, founder of Gator Capital Management, to deconstruct his 20%+ annualized track record in the financial sector. While many generalist PMs view financials as a "sleepy backwater" or overly complex, Derek explains how he extracts alpha from regional banks, brokerages, and insurance companies by identifying fundamental business changes before they are reflected in the tape.The conversation moves from the microstructure of bank underwriting in a post-Dodd-Frank regime to the practicalities of portfolio construction, including why Derek has expanded his concentration from 25 to 40 names and his strict discipline against "averaging down" on losers. We also dive into the private credit narrative, the actual risk of systemic leverage in non-bank financials, and how generative AI is shifting the valuation multiples of moaty info-service businesses like Morningstar and FactSet.00:00 Intro01:06 Derek's +21% annualized return track record02:50 Fundamental business change vs market noise in Robinhood05:25 Portfolio construction: Concentration limits and adding to winners09:09 Sourcing alpha and identifying three-year doubles in financials12:44 Developing edge through repetition and management team cycles14:16 Why the post-GFC regime fundamentally changed bank underwriting17:07 Assessing tail risk and leverage in the private credit market21:23 AI-driven market dispersion and identifying moaty businesses24:11 Why shareholder base turnover matters for timing broken charts25:57 AI disruption vs trust-based moats in financial services29:37 Integrating AI into fundamental research and SEC filing analysis32:31 Scaling regional bank positions and managing liquidity constraints35:39 Risk management: Permanent capital loss vs mark-to-market volatility37:12 Capacity constraints: Optimizing for returns over AUM scale44:14 Behavioral edge and avoiding the "degree of difficulty" trap50:39 Career risk and the reality of active money management54:18 Breaking into the industry via public stock write-ups