Ryan O'Connor founded Crossroads Capital in 2016, bringing expertise in asymmetric idea generation focused on emerging franchises and catalyst-driven special situations. His investment approach is deeply influenced by his grandfather Bill O'Connor, who was an early investor in Warren Buffett's original partnership. Ryan's research has been featured in Bloomberg and The Wall Street Journal, and he maintains active membership in prestigious investment communities including Joel Greenblatt's Value Investors Club and MOI Global. The team has expanded to include Managing Partner Cole Lysaught (2023), who brings operational expertise from successfully founding and selling Bloom Health Partners, along with experienced professionals Adam Brass CFA, Justin Weiss CFA JD, George Thornton, and Ed Harelik as Director of Client Services.

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Crossroads Capital operates on the principle that securities represent ownership in businesses whose intrinsic value equals the discounted sum of expected future cash flows. Despite generally efficient markets, they identify significant mispricings caused by non-economic selling, career risk, psychological biases, and informational inefficiencies. Their strategy focuses on purchasing securities at substantial discounts to intrinsic value, particularly those with clear catalysts driving price convergence within definable timeframes. They target securities prone to mispricing including value plays, special situations, event-driven investments, emerging franchises, and catalyst-driven shorts. The firm emphasizes concentration in 10-15 superior ideas, leveraging patience and discipline while considering volatility as opportunity rather than risk.

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