[lusr]

I completely agree. It feels like intellectualization - a subconscious defence of personal choices made out to look like fact. I see this in everyday life all the time, and I daresay the root of it is an irrational subconscious fear that the person being criticized (here, the friend) may succeed, and what that potential success implies about the speaker.

In this case, if the friend follows their "me too" path and "succeeds", the author's beliefs about the "right" path would be shown to be unfounded. Of course at this point the author has invested, as stated in the post, five years of time and energy on this path and is unsurprisingly going to be reluctant to admit there may have been another path that could have taken him to the same destination with a lower time and energy investment. Instead, the author intellectualizes and rationalizes his choices to prevent acknowledging the uncomfortable truth.

There's a mentally healthier way of dealing with this: acknowledge there are multiple paths, and acknowledge that destinations are multi-variate. For example, what does the friend want as a destination, just money? Maybe the author wants something more - experience, satisfaction of starting their own business, etc. It's dysfunctional to suggest the friend should choose the same destination as the author; once this is accepted, you can happily get on with your choice of path and not worry that others have made different choices. Occasionally, of course, you will find somebody has arrived at the same destination you desire with less time and energy -- at that point, set aside your ego and learn from them!

[jack-r-abbit]

The OP says: That’s not what I meant. I know YC is a great place. But why do YOU want to get in?

I don't think he was being as critical of the path chosen but more so of why the friend decided to start the journey to begin with. I might be misinterpreting things though.

[lusr]

The friend answered the question:

"Listen. It’s never been easier to start a company. And right now, money is thrown left and right. In the past year alone, six of my colleagues left my company to start their own startups. I figured if they can do it, I can too."

OP didn't like that answer and skipped past it, and I'm playing psychoanalyst by wondering why.

[steventruong]

That answer was a "me too" answer isn't it (not arguing the merits of a response regardless of whether it is or isn't). I think the author (I'm guessing) was hoping for a deeper answer than "I'm doing this because everyone else is and it appears easy" rather than simply skipping over it.

Just playing devils advocate here.