When Positive EV Goes Wrong

In business, leaders make decisions every day under uncertainty. But what if the biggest risk isn’t the one you see — it’s the one you misunderstand?

In this episode of the Strategy and Leadership Podcast, host Anthony Taylor sits down with Dr. Michael Orkin, Professor Emeritus of Statistics and author of The Story of Chance: Beyond the Margin of Error, to explore how probability, randomness, and cognitive bias shape executive decision-making.

Drawing from decades of experience in statistics, gambling mathematics, and data science, Dr. Orkin explains why leaders often confuse correlation with causation, overestimate their odds of success, and underestimate the role of scale and opportunity in rare events. From lottery math to prediction markets, casino risk models to executive strategy, this conversation reframes how organizations should think about expected value and long-term advantage.

Dr. Orkin breaks down why even “positive EV” opportunities can fail if risk is mismanaged, introduces the Kelly Criterion as a disciplined approach to capital allocation, and highlights how cognitive traps can distort judgment at every level of leadership.

Anthony and Dr. Orkin explore what it means to increase your “house edge” in business — not through luck, but through disciplined probability thinking, structured decision-making, and clear risk allocation.

The episode closes with a powerful reminder: strategy is not about eliminating uncertainty — it’s about making smarter bets under uncertainty.

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In this episode, you will learn:

• Why rare events happen more often than you think

• The difference between correlation and causation in business data

• How expected value applies to strategic decisions

• Why risk mismanagement destroys even strong opportunities

• How the Kelly Criterion informs smarter capital allocation

• How leaders can avoid cognitive traps when interpreting data

Connect with Dr. Michael Orkin

Website: https://drmikeorkin.com

LinkedIn: https://www.linkedin.com/in/dr-mike-orkin-5600584/

About the Host

Anthony Taylor is the CEO and Founder of SME Strategy and a trusted expert in organizational alignment and strategy execution. With over 15 years of experience facilitating strategic planning and leadership development, he helps organizations align their people, accelerate execution, and achieve their biggest goals.

Connect with Anthony: linkedin.com/in/anthonyctaylor604

About SME Strategy

SME Strategy is a management consulting firm specializing in strategic planning and implementation. We help organizations align their teams around a shared vision so they can focus on what truly drives results.

Learn more: www.smestrategy.net

Podcast produced by: www.rednyne.com