There's a subtle, rather meta feeling I can't shake when I read "cautionary" blog posts like these. It's the feeling that maybe the author isn't writing it for anyone else's benefit as much as their own. Like the author writes to reinforce that, unlike said "friend" who's making all these cautionary mistakes, they themselves are in it for all the right reasons. Every time the author makes a, "he" statement, you can j…
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.
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.