Ben Horowitz recently published his book The Hard Things about Hard Things. It’s no exaggeration to say I love it. As a third-time founder having experienced many of the challenges firsthand, I wish that book had been written 15 years ago, when I was trying to build my first company (although I’m not sure I would have read it back then; learning seems to be easier in hindsight). One of the great things about Ben’s book is that it focuses on sharing the hard lessons when it’s not all smooth sailing.

Inspired by this, I thought I would add some of the lessons from Tradeshift. Just like Opsware, Tradeshift is a company in wartime, as are most B2B companies try- ing to break into highly entrenched software markets controlled by incumbents with ...