a piece on failure

I wrote a piece on failure for my monthly Mainebiz articles. It tackles the issue from perspectives of the entrepreneur, me as an investor and me as a human (if I can classify myself that way). Here's a piece of that piece

It is said that a venture capitalist spends more time bemoaning his failures than celebrating his wins. In part, I suspect, it’s because there are statistically more of the former. But it’s not really the loss of capital that is so agonizing to an investor — it’s the human drama. Watching an entrepreneur wind down her company and seeing the look in her eye as she fights and claws only to watch it all go. It’s tough to watch.
It’s tough to experience, as well. After all, a company’s failure is my failure. Whether it’s an entrepreneur I overestimated, a plan I signed off on, a technology that didn’t pan out, I own it. I’m the one who believed and put my chips down. I’m the one who watched and advised from the board, who worked outside the board to co-develop teams and plans. And like entrepreneurs, I have backers who depend on me to be a good ballplayer, to make my wins large enough to make up for my losses. I take my responsibility seriously and spend most of my waking hours thinking about what I could have done differently and what I can do better. Managing 10 or more company investments feels, sometimes, like I can never really do enough.
For the most part, I’ve learned to live with failure. You can do a great job as an investor — pick a winning concept, assemble a competent team and board, pull together enough capital to take a run at it — and, well, nothing. Too late, too early, product glitches, management glitches, acts of God, it’s all there as the great teacher.