We emphasize the role of appraisal—how individuals think—and develop dynamic theory to test entrepreneurial stress over a 20-day period. In so doing, we reintroduce and demonstrate the notion that stress is an individual level process that can unfold differently for different individuals. We test our model with 286 appraisals made by 29 entrepreneurs. We find support for a synergistic appraisal of stressors and for within individual variation in appraisal, coping, and strain over time. Additionally, we find that daily level active coping increases same day strain. Our results provide strong support for more dynamic theorizing and testing in entrepreneurial stress research.