This takes a bit of ruthless judgment — is your first hired salesperson really the right fit for head of sales, especially if/when you hire several hundred salespeople? Wilson says that inexperienced founders can often become emotionally attached to their first team; serial entrepreneurs, on the other hand, have a better grasp of when to hire, when to fire, and when to just shed their entire company skin and recruit brand-new personnel.
Stay honest and transparent, of course, but make sure you keep the company’s focus. To this end, Wilson suggests reading the Steve Jobs biography by Walter Isaacson, and learning from Jobs’ brutal cutting of development projects when he re-entered Apple in the late ’90s.
If you’re trying to learn how to be a loyal friend, don’t follow Jobs example. If you want to be a stellar founder, you could probably take some notes.