Cluelessness and red tape are the symptoms of the dysfunctional relationships he's talking about. If the relationships were working properly, it'd be easier to

Cluelessness and red tape are the symptoms of the dysfunctional relationships he's talking about. If the relationships were working properly, it'd be easier to get your 15-minute procurement job done, and nobody would be trying to standardize you on a crappy tool. Don't worry about missing any boats. If you like a job take it, if not, don't. If you want to start a business, start it, and focus on making money rather than chasing techcrunch headlines and VCs. If you're evaluating work at a startup, look at it like you're your agent: 1) What's the comp package? Equity, unless very significant, is basically a deferred bonus that you can't count on. Don't overrate it. 2) What skills will you get to develop? It's usually not worth taking a lower salary for X,000 shares of "i don't know". But it can absolutely be worth taking a lower salary now in exchange for higher skills later.