For those young companies that have spent the last eighteen months fundraising, we should start a support group. Successfully raising money in the wake of the financial apocalypse is a test of will, mettle, but above all our sense of humor. We were one of the few that have been fortunate enough to raise successfully while other, equally worthy, start-ups were shutting their doors. The question that I often wrestle with is: What makes us so special?

In the spirit of helping others, I thought I would post on what has worked for us and things we need to do better.

Keep it real. When there is bad news to tell, just state the facts. For a driven over-achiever like me, admitting my failings requires a good bit of courage. However, I have found that excuses make me look and feel weak. Trying to explain away poor performance by blaming the market is just, as my mother would say, putting lipstick on the pig. What happened? What do we intend to do about it? Those are the questions we need to answer when any of our best laid plans get derailed. The question “why?” is best left to a group post-mortem – a place to reflect and learn. Leading with the “why” or leveraging the “why” as an excuse for poor performance is a quick way to lose team and investor trust.

Stay positive, but be realistic. My best strength and greatest liability is my enduring positivity. It allows me to will things into existence. The liability side of this is overestimating my abilities. Looking back on 2009, several of my key assumptions required that we have near flawless execution. We’re good, but we’re not superhuman. George Dalton, my long time friend and mentor, has reminded me often that I need a “dark cloud”– someone willing to tell me my most cherished assumptions are flawed. I always have to take a hard look at our key assumptions. What if one or more of these assumptions proves false? How will we adjust?

Laugh at yourself, often. When the going gets tough, the tough find the humor in the situation. I cannot tell you how many times I have been saved from despair by a good belly laugh. Although we may expect perfection from yourself (another support group I’d like to start), we are all (as far as I know) human. If we aren’t failing, we aren’t progressing. The key is to learn from our missteps rather than heed the siren call of self-flagellation. The only way I have found to lash myself to the mast of learning rather than dive in and start swimming towards self-loathing is to laugh. Thankfully, my team has a brilliant collective sense of humor and has helped me stay on course here.

Keep the endgame in mind. There are days as an entrepreneur when I think… I knew how hard this would be and I did it again. What was I thinking?! My enduring love of the endgame is what keeps me going. I love Sudoku and often think business is a bit like the magic box. So often things are obscured, don’t line up, and just seem like total chaos. And then, I find an answer which leads to another and another… Before I know it, the puzzle is solved. The great satisfaction I feel bringing Ordo ab Chao is what keeps me going.* Now if I can only do this nifty trick with my three and two year old, I’d really be onto something!

* Order out of Chaos – and yes, I just finished Dan Brown’s The Lost Symbol at 1am last night.