Anyone who has been through an incubator has probably heard this line:

"Most of your companies will fail. And now that I've said that, you're all feeling sorry for everyone else in the room."

Honestly, I encourage my friends to take risks and try new things, even if I have inner doubts about their ability to pull it off. I do so because I think that trying something really, really hard improves you skill set -- even if you end up failing.

If a friend said, "I'm going to try and get into the Olympics!" would you tell them all the ways they're likely to fail? Or would you encourage them to try and achieve a dream? The key is not understating the risks; be both encouraging and honest.

I have never heard the line "most of your companies will fail" from anyone I know of in Y Combinator. Mostly because "fail" isn't really well defined -- even a mediocre startup is usually more interesting than a boring job. Even founding the next Instagram might be a failure for someone who really cares about medicine or space.

I agree with you that it's not for anyone, other than the man in the arena, to determine whether someone belongs in a startup or not. At the same time, I strongly agree with the observations made by OP. The social pressure is strong in the valley: all people talk about are startups. Its perceived to be easy to work for a year or two with a couple smart friends and get bought by Facebook or Google. Zuck bragged at SUS two years ago that (a) every CEO they'd acquired was still working at Facebook and (b) they'd shut down every product they'd acquired. Many people aren't "in it" to build great companies. That's just how Silicon Valley works. On the other hand, many of the best companies are highly product focused and driven by a desire to do something more. Most people on both ends of the spectrum will fail. Perhaps this is correlated to the underlying motivations, but I don't think anyone has data on that (probably because it's ill-defined). It may be wrong to moralize about this dichotomy, but it's certainly there.

Of course it's there. We're human - we're all subject to circumstance and surroundings. We can't say with certainty that we would be doing tech startups if we were born in another time or another place (ie your lack of data - I agree). So where do you draw the line?

The issue I take with this type of writing is that, at best, it's pointless. And at its worst, it's desctuctive.

Pointless - It's not fact based. It presents no new, compelling ideas. It's not helpful for practical purposes, or optimistic for inspirational ones. What's the point? Why was it written? (For the authors sake, I think.)

Destructive - It draws lines and separates classes, the higher of which the author subtly places himself in while condescending the hopeless "friend". Where would we be on our own startup journeys if our "friends" were so (not) supportive?

And this, by the way, is where someone gets to call me and my comments out for being super hypocritical ;) </irony>

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!

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.

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.

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.

1. I can certainly see how it can be interpreted in the context you've pointed out but that's not how I would have interpreted it.

2. I disagree that it presents no new compelling idea. What is not new to you and me maybe new to someone else. Helpful or not is very much in the eye of the reader and what they end up doing with that information and how they interpret and manage it. There are merits to the post whether or not you agree with them or whether you think there are any to begin with.

3. While I totally agree that at the end of the day, the decision to do something resides with the decision maker, I also acknowledge that what the author points out as "me too" syndrome do exist to an extent and in many ways that can in fact be harmful as well.

4. I do agree its never good to be condescending but I don't believe that was the intention here. You asked where would we on our own startup journey if our friends were not so supportive. While I do agree as a whole, I also believe that a great friend doesn't always blindly support their friend. Sometimes being a friend simply means having the courage to point out where your concerns are and why you are concerned. In the end, the support is to allow your friend to take that information and go about making the choices he or she needs to make. While the author didn't dive into this (what he did or didn't discuss with his friend beyond what was posted), I have a hard time believing they made this post with a condescending tone over trying to help others (the readers) see what may be obvious to you and me but may not be to many.

I think the word you're looking for is "patronizing," with the implied title actually being "Them (or You) too?"

Exactly. Also, the idea that you have to have higher ideals to become an entrepreneur is laughable at best. It's about business, not self realization. If anything, this piece made me sympathize with the friend who approaches YC with irreverence and gusto instead of fear and angst of not doing a startup for the "right" reasons.

Exactly. Good way to put it.

I didn't think that when I read it but I can see where one could think that. I do think he's got a point about the "me, too" start up bandwagon that appears to be growing. I would not try to discourage anyone from giving it a go as long as they are being smart about it. I would if/when the time was right.

"I would not try to discourage anyone from giving it a go"

That's the ticket right there.

When friends and friends-of-friends have expressed a curiosity into startups, I treat them with the same respect I would hope for. Very clear - forceful even - about the risks and challenges of entrepreneurship, and very, very critical about ideas (but always with the "...but who am I?" disclaimer). But overall, I try and default to being supportive and encouraging.

It's not charity either. There are absolutely selfish benefits behind being supportive. Like Guy Kawasaki or Keith Ferrazzi would point out - the more helpful you are, the more valuable your network. It's impossible to quantify, but being supportive early on is just the best thing for everyone involved.

yes... which is why I also had the part about being smart about it. sometimes a bad idea really is just a bad idea. ;)

The main over-arching point is perfectly palatable, but the probing element ("That’s not what I meant. I know YC is a great place. But why do YOU want to get in?") in the post comes off as passive-agressive.