One time I lost a large deal because the buyer's boss came across a controversial piece I'd written, and didn't think I was a good fit with their buttoned-down

One time I lost a large deal because the buyer's boss came across a controversial piece I'd written, and didn't think I was a good fit with their buttoned-down formal organization. Later, I made a very similar deal for about 30% more money, that wouldn't have happened without losing the first one. I reckon, better to lose by boldness than lose by tameness. Either one can bite you, but at least you get some satisfaction out of losing for being too bold.