One character from Super Pumped is David Plouffe who was the governmental ambassador for Uber. He was their plan B.
Plan A during the licensed-drivers-black-car-only-days (2010-2012) was to enter a city quietly, scale quickly, and enlist the happy customers if the government tried to stop them. If that didn’t work, as was the case in Portland, Plouffe would try to work with the local governments toward a solution. Plan A and Plan B.
Plouffe was a good candidate for this because he’s credited with helping candidate Barack Obama become president. In a Talk at Google in 2009, Plouffe talks about all the things they did to get Obama elected. The most important was a connection between the macro (strategy, numerical targets, messages) and the micro (how many houses to visit, text message updates).
Plouffe and his team figured out that winning the presidency wasn’t about creating the best ads (Daisy, Bear, Read my lips, etc.) but manufacturing enough votes. The real puzzle was getting to 270.
Working backward from that goal, the Obama team developed a strategy. If they were to win a certain state they’d need to register a certain number of voters. Like a doctor might manage a patient’s diabetes, the Obama team was precise with evaluations, measurements, and deadlines.
This clarity of strategy led to what Plouffe calls “uneventful decision making.” He said, "We tried to educate people in the campaign, from senior staff down to the volunteer, what our theory of success was, so that decision making became uneventful. Actions either support your strategy or they don't and 98% of things that cross your desk are an easy Yes or No."
With the right culture and strategy, Plouffe won the votes and Obama won the campaign. This story is a bit of selection bias but the attitude is admirable. Is my strategy clear enough that decisions are easy?
Business is easier, though still not easy, when competition is minimal (ideally non-existent). This means being different, something not-so-easy in itself, but easier when decision making is uneventful.