Dr. Aleksandr Yampolskiy is the co-founder and CEO of SecurityScorecard, one of the world's most trusted cybersecurity brands with tens of thousands of customers, including half of the Fortune 100 and nine of the top 10 U.S. banks. Before founding SecurityScorecard in 2014, Alex earned a Ph.D. in cryptography from Yale, built authentication infrastructure for Goldman Sachs and Oracle, and served as CISO at Gilt Groupe, where a near-miss with exposed credit card data became the genesis for an entirely new category of cybersecurity.

In this episode, Alex traces his journey from a 14-year-old immigrant kid whose friend handed him a virus-infected floppy disk with “Prince of Persia” on it, all the way to building a company that now scores the security of every organization on the internet. He breaks down what it takes to create a market category from scratch, why the CISO version of him was more fun to have a beer with, and why North Korea tried to recruit his developers through a fake hedge fund.

Jack Clabby and co-host Kayley Jerrell talk with Alex about the difference between robustness and resilience, why SecurityScorecard banned PowerPoint slides, and the single most dangerous thing a board member can say in a meeting. Alex also argues that companies openly admitting security breaches actually makes the whole ecosystem stronger.

In the lifestyle polygraph segment, Alex reveals he grades restaurants by their health inspection scores, shares what The Inner Game of Tennis taught him about trusting his gut, and tells us how chess got him a date with his future wife even though she had never played chess.

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