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You fall into three groups. Some of you already have all kinds of ambitious plans. You're already admitted to med school for the fall, or whatever. Others of you have no ambitious plans and no desire to have any. You just want to have a happy life, and that's cool. But in the middle, there's a group who wish they had ambitious plans, but don't. This speech is for you. I'm going to tell you how to get ambitious plans.
The first step is to realize that the subway stops here. Up to this point in life, most of you have been rolling on train tracks. Elementary school, middle school, high school, college—it was always clear what the next stop was. In the process you've been trained to believe something that’s not true: that all of life is train tracks. And there are some jobs where you can make it stay like train tracks if you want, but really today is the last stop.
Ok, then what? How do you search through thousands of options? To be honest, you can’t. You have to use some kind of trick for narrowing them down. My favorite trick is people. Talk to people. Get introduced to new people. Find the people that you think are interesting, and then ask what they're working on. And if you find yourself working at a place where you don't like the people, get out.
If you have ambitious plans, a lot of people will be skeptical. You'll seem like you're getting above yourself, except perhaps to your parents. And even they will usually be too conservative. Plus, most ambitious ideas seem wrong at first. If a new idea was obviously good, someone else would have already done it. 
When we started Y Combinator, everyone treated it as a joke. We were funding kids right out of college and only giving them small amounts of money. How could these startups ever succeed? Now everyone knows it's a good idea to fund young founders, but twenty years ago, it just seemed lame. But we didn't care what people thought of us. We knew we were onto something. In fact it was good that we seemed lame, because that meant it took several years before people started to copy us.
most ambitious ideas seem wrong at first
Amen.
And this "We don't care what other people think because we know we're on to something" energy she's talking about, I can feel it in the bitcoin space.
However, I do wonder how you should talk to someone with ambitious dreams, but that your honest assessment is that they're too much of a dreamer and not enough of a doer.
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However, I do wonder how you should talk to someone with ambitious dreams, but that your honest assessment is that they're too much of a dreamer and not enough of a doer.
I'll usually advise these people to take more risk that'll be data-yielding (like talking to people). You have to flank them because no one wants to be told who they are, yet if they're going to be successful they shouldn't mind discovering it for themselves.
More generally, it's hard to know whether you're talking the exceptions or the people for whom the rule exists. The best solution I've seen is to bury your advice in the right places where only the intended audience will find it.
She does a good job dealing with this by explicitly addressing a group that most people wouldn't publicly admit they belong to.
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