"He hesitates when it comes to sales because he does not see himself as a sales person". "... is holding back a bit" "he would work one day a week + weekends

"He hesitates when it comes to sales because he does not see himself as a sales person". "... is holding back a bit" "he would work one day a week + weekends (his work situation is flexible) and eventually go full-time" HUGE red flags right there. Do not give him equity.