One Liner: the best teacher for the ass-whuppin’ of leading a startup is experience, and the second-best is this series of shared raw experiences with actionable guidance frameworks and few inspirational/insipid platitudes.
Rockin’ book. This book is probably not interesting enough as a window into startup culture (read “The Social Network” for that), but along with Peter Thiel’s “Zero to One” I would put this on the must read list for seasoned and novice founders.
Leading a startup can be a beatdown. Every positive moment comes with six in the other direction. Ben Horowitz’s “The Hard Thing About Hard Things: Building A Business When There Are No Easy Answers” could just have easily been called “yeah, it’s fucking hard.” It chronicles Ben’s work at Loudcloud with Marc Andreesen and the incredibly turbulent path that did have an eventual happy ending. It covers a lot that CEOs wrestle with – how to lay off people, poaching employees from friends companies – but it also touches a lot on the self-mental-management of startup lead. We should all have psychiatrists, and I’m in a roundtable breakfast group with a pack of other CEO/Founders and our monthly sessions are one part group problem solving and five parts group therapy.
I felt some kind of relief after I finished it. I don’t know if it was more “ok, I’m not crazy” or “this is how it is, handle it or quit”, but it was a psychological shot in the melon.