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.
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.