When and how much risk to take? In October 2020, Ken Sweder, CEO of Individual FoodService ("IFS"), contemplated this question as he evaluated a proposal to acquire Brady Industries, a distributor of janitorial and sanitation products. Sweder and his private equity partners at Kelso & Company had been working hard to grow IFS, and now they had a unique opportunity to make a transformative acquisition. The deal had great potential and risks; it was unclear if this was the right time to make such a large, complex acquisition amid disruptions from the COVID-19 pandemic. Sweder needed to decide if he should recommend the transaction and, if so, how to set the right value creation plan for the combined company.