Leading a startup has always been challenging, even under the best conditions. Founders need to quickly master a tremendous range of skills, from building a fantastic product and nailing go-to-market efforts to raising money and managing a board, all while figuring out hiring, culture and compensation. Starting a company is also a lonely endeavor, one that forces founders to make difficult decisions every day with imperfect information. While triaging these challenges, eventually every founder runs headfirst into a problem they haven’t seen before, the kind that leaves them unsure of where to start.