Ben Gilbert: evaluation

Transcript context

…I think I always tell people that the most common mistake that I see in young people is that they overplan their career. Like, oh, I want to do X, I want to be vice-president, or I want to make so much money by a certain time. When you overplan your career, there's this human bias, which is to look for a signal that agrees with the plan that you have and ignore everything else that doesn't agree with it. My advice for young people is don't overplan. You never know what opportunities are going to come up. I plan to stay down at a company my whole life, It was my place. My brother wound up being there. Being open to possibilities, being open to opportunities, and then when you get that opportunity, going all in. It's just, don't hedge. If you're going to be in something, go all in, do what's required of you and then 50% more, like blow people away. Tomorrow, maybe something else comes up and you'll get there. While you're in, you go all in. But at the same time, keep your eyes open because you never know. All right, we're going to catch back up to that Expedia era. Thirteen years, you have pretty wild competition with booking. com. I think you learn a lot of lessons from watching Booking just crushed it. Top line, profit margins, rate of expansion, everything about it, Booking built a hell of a company. When you're on the Expedia side of things, and then you get a fresh start at Uber, how do you take those lessons with you? And what did you learn? God, I learned so much. Booking was an execution machine. Their focus when we talked about focus was hotels, hotels, hotels. Expedia started with Air. Hotels was, to some extent, secondary. I think one of the lessons is like, hey, go off to the larger market. If you're a marketplace business, go after fragmentation of supply, which is if you think about hotels, there are so many more hotels in the world that there are airlines. I think they focused completely in the right area, built a global business first, and just were an absolute execution machine. The other area was that Expedia was probably more focused on building demand, consumer demand, brand, et cetera. Booking was more supply-led.…

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