Author here. Your thinking is equally weird to me. I value my time for sure, but isn't there a cost in not persuing what I'm genuinely curious about? What if a successful startup had come out of it?
By the way, this took place in 2011-2012, when Google Flights didn't exist.
You're absolutely right - the good old trial and error applies when it comes to innovation. There's just no way someone could come up with a breakthrough technology or product on their very first try. You absolutely need to be relentless at trying and testing out new things.
And yes, diversity of thought isn't nearly as valued as it should be these days. A team of people who all think the same about everything probably won't innovate as much as a team whose members can think for themselves. Just think about the early Paypal days (Peter Thiel, Max Levchin, Elon Musk, etc.)!