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I think he's saying that a failed startup is like the end of your first serious high school relationship. It was your whole world for a while and when it comes crashing down it feels like nothing will ever be right again. But life goes on and if you're lucky you eventually look back and realized that you learned a lot and grew as a person and you've moved forward to other things that are now important to you.

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It doesn't really help to comfort a broken hearted teenager by saying, "don't worry, you'll find love again! Just look at me and my beautiful wife!"

Except that, in your analogy, my wife is now married to someone else.

The point of the analogy is merely this: You are telling someone going through a potentially awful experience that you were in an entirely different situation where the outcome for you was far far better.

So if you really want to stick with the analogy, it's like an amicably-divorced-and-remarried man telling a widower to just cheer up.

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