How I Invest with David Weisburd

E303: What Blackjack Taught Me About Investing w/Ari Levy

Feb 12, 2026
Guest
Ari Levy
Ari Levy, Founder and CIO of Lakeview Investment Group, applies card‑counting lessons and probability theory to public equity investing. He talks about disciplined position sizing, why small‑cap markets stay inefficient, the tradeoffs between arbitrage and activist approaches, and how friendly board engagement and access can create asymmetric outcomes.
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ANECDOTE

Early Games Sparked Investing Philosophy

  • Ari Levy learned probability and game theory early by simulating baseball seasons and studying cards on an Apple IIe as a child.
  • Those experiments led him to card counting at Stanford and shaped his approach to risk and strategy in investing.
ANECDOTE

Blackjack Team Taught Risk Sizing

  • Ari describes running a blackjack team at Stanford under a professor who taught game theory and probability.
  • He applied card-counting lessons like the Kelly criterion to inform position sizing and risk management in markets.
INSIGHT

Arb Can Break From Idiosyncratic Events

  • Even seemingly 'risk-free' arbitrage can fail from second-order, idiosyncratic events like registration errors or counterparty misconduct.
  • Ari warns that structural assumptions (e.g., create/redeem mechanisms) can break and cause large premia or losses.
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