Page 62:

And then it hit me. I’d been looking at it all wrong. The right thought wasn’t, Holy shit, the governor is totally MIA.

The right thought was, Holy shit, this guy is totally checked out. Someone’s gotta run the place. And if no one’s going to tell us what we can and can’t do, we might as well do as much as we can.

Page 82:

Howard understood something both intellectually and intuitively that most people in politics and communications just don’t get. The best spin is no spin. Rather than triaging and obfuscating and boasting and attacking, just answer the question honestly, thoughtfully, and simply. Reporters have built-in bullshit detectors. The more you try to spin them, the more you just convince them that there’s something more to the story than you’re telling them. You’re just digging your own grave. Whatever it is, own it. Explain why you did whatever you did. Why you decided whatever you decided. Assuming you were logical in how you went about whatever it was, whether you got it right or wrong, people can at least understand what happened and that’s all most reporters want: for things to make sense.

Page 110:

If you’re a startup trying to decide whether to ask for permission or beg for forgiveness:

  • What’s the jurisdiction? Are the regulators and electeds corrupt or can you work with them?
  • Can you count on grassroots support from customers?
  • How compelling is your narrative?
  • What are the existing laws on the books?
  • Whom are you begging for forgiveness? (3 years in jail is a lot different than a $300 fine)
  • What are the political strengths of your opponents?
  • How important is this? (Do you have to win no matter what?)

Page 110:

If you’re a startup facing inaction from regulators who don’t know how to interpret what you do under current law (or refuse to do so):

  • Why are they stalled? Confusion, regulatory capture, or intransigence?
  • Is pay-to-play inolved?
  • Do they hae a valid reason to delay? Does it open up a can of regulatory/legistlative worms?
  • What will it take to move them? Do you need a big public fight?
  • If you succeed in moving them, how does it impact other jurisdictions?