Accepted by Orie Barron. We thank Tillinghast-Towers Perrin for providing the insurance data. We would like to thank several industry participants who have shared their valuable time with us. In particular, we thank Elissa Sirovatka of Tillinghast, David Allan of General Reinsurance Corporation, Dan Bailey of Bailey Cavalieri LLC, Michael Early and Frank Kastelic of the Chicago Underwriting Group, Lori Fuchs of Honeywell, Phil Norton of Arthur J. Gallagher and Co., and Paul Van Zuiden of Risk Management & Insurance Consulting LLC. We are grateful to Heowk Kiat Koh for assistance with the data collection. We acknowledge helpful suggestions from Orie Barron (associate editor), two anonymous referees, Ana Albuquerque, Romana Autrey, Paul Beck, Foong-Song Cheong, Daniel Cohen, Dain Donelson, Brian Mittendorf, Partha Mohanram, Shyam Sunder, Jake Thomas and Frank Zhang. We also thank workshop participants at the University of Texas at Dallas, Southern Methodist University, Boston University, University of Minnesota, George Mason University and University of Illinois at Urbana-Champaign for valuable comments. Any errors are our own.