I really enjoyed Mark Suster's post earlier this week, What's it Like Being a VC?, in which he details the pluses (many) and minuses (few) of "crossing over to the dark side" from entrepreneur to VC. Having made the same switch - albeit on a <cough> somewhat smaller scale* - his description of both the positives and negatives rang true.
One thing Mark didn't mention in his piece - but that I've been appreciating about my new role - is that the emotional tone of the investor position is almost the complete opposite of my experience as an entrepreneur. As a startup founder you're often in "ask" mode - whether you're raising money or selling or recruiting or managing, it's most often from a position of scarcity, and (as much as you may seek to position otherwise), you typically need the win more than the prospective customer or employee or journalist needs you.
In contrast, as an investor I'm find myself emotionally in "give" mode much more often - whether it's spending time with portfolio companies or entrepreneurs seeking funding, writing checks to help companies grow, or sharing deals and ideas with other investors, my focus now is much less about meeting my own needs, and much more about helping other people meet theirs.
Maybe it's just the way I'm wired, but I get huge satisfaction by being on the "give" side more often than the "ask" - it's one of the (many) unexpected benefits I've found in my own switch to the dark side.
* Founder's Co-op is currently investing from a $2.5MM pool vs. GRP's $1B+ under management