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

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

23:28 Feb 12, 2026
About this episode
Where does real edge still exist in public markets and how do you size risk when certainty doesn’t exist? In this episode, I talk with Ari Levy, Founder and CIO of Lakeview Investment Group, about applying probability theory, arbitrage, and disciplined position sizing to public equity investing. Ari explains how early lessons from card counting and game theory shaped his approach to risk, why small-cap markets remain structurally inefficient, and how activism, arbitrage, and management access can create asymmetric outcomes—without blowing up the portfolio. Highlights: Probability theory as the foundation of investing Why position sizing matters more than prediction Hidden risks in “risk-free” arbitrage trades Structural inefficiency in small-cap equities Passive flows as a tailwind for active small-cap investors Friendly activism and aligning boards with shareholders When public companies should be private Arbitrage vs. fundamental stock picking—and when each works Avoiding value traps in a tech-driven world Guest Bio: Ari Levy is the Founder, President, and Chief Investment Officer of Lakeview Investment Group, where he oversees portfolio construction, risk management, and investment decision-making across public equity strategies. A long-term, engaged owner, Ari frequently works with management teams and boards on strategy, capital allocation, and governance. Earlier in his career, he served as a Vice President and Share Partner at Advisory Research and was President of Levy Acquisition Corp., later serving on the board of Del Taco until its acquisition by Jack in the Box. Ari holds a B.A. in International Relations from Stanford University. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com. We’d like to thank AlphaSense for sponsoring this episode! Sponsor: AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more. Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ Stay Connected with Ari Le
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