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We follow the careers of habitual and novice entrepreneurs to investigate whether entrepreneurial experience matters for performance. Specifically, we compare the ability of serial, portfolio, and novice entrepreneurs to create and sustain jobs by looking at the cumulative variation in total employment across all firms held by those entrepreneurs over time. We find that portfolio entrepreneurs outperform both serial and novice entrepreneurs, displaying a greater ability to add and sustain jobs across all their firms, while serial entrepreneurs outperform novice entrepreneurs. We also find that longer periods spent away from business ownership weaken the future performance of habitual entrepreneurs. [ABSTRACT FROM AUTHOR]